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Details for Patent: 7,915,236

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Details for Patent: 7,915,236

Title:Proteasome inhibitors and methods of using the same
Abstract: The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly of indirectly with proteasome activity.
Inventor(s): Bernardini; Raffaella (Calci, IT), Bernareggi; Alberto (Concorezzo, IT), Cassara; Paolo G. (Monza, IT), Chatterjee; Sankar (Wynnewood, PA), D'Arasmo; Germano (Novate Milanese, IT), De Munari; Sergio (Milan, IT), Ferretti; Edmondo (Ravenna, IT), Iqbal; Mohamed (Malvern, PA), Menta; Ernesto (Cernusco sul Naviglio, IT), Messina McLaughlin; Patricia A. (Glen Mills, PA), Oliva; Ambrogio (Saronno, IT)
Assignee: Cephalon, Inc. (Frazer, PA)
Filing Date:Jul 01, 2009
Application Number:12/496,359
Claims:1. A compound of Formula (I) ##STR00682## or pharmaceutically acceptable salt, stereoisomeric or tautomeric form thereof, wherein: R.sup.1 is C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, or C.sub.3-C.sub.7 cycloalkyl; R.sup.2 is --(CH.sub.2).sub.aCH.sub.2NHC(.dbd.NR.sup.4)NH--Y, --(CH.sub.2).sub.bCH.sub.2CONR.sup.5R.sup.6, --(CH.sub.2).sub.cCH.sub.2N(R.sup.4)CONH.sub.2, --(CH.sub.2).sub.dCH(R.sup.7)NR.sup.9R.sup.10, or --(CH.sub.2).sub.eCH(R.sup.7)ZR.sup.8; a, b, and c are each, independently, 0, 1, 2, 3, 4, 5, or 6; d and e are each, independently, 0, 1, 2, 3, or 4; R.sup.4 is H or C.sub.1-C.sub.10 alkyl; R.sup.5 and R.sup.6 are each, independently, H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, or an amino protecting group; alternatively, R.sup.5 and R.sup.6 together with the N atom to which they are attached form a heterocarbocyclyl group; R.sup.7 is H or C.sub.1-C.sub.10 alkyl; R.sup.8 is H, C.sub.1-C.sub.10 alkyl, alkyl-S(.dbd.O).sub.2--, aryl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O).sub.2--, --SO.sub.3H, or a protecting group; R.sup.9 is H, C.sub.1-C.sub.10 alkyl, carbocyclyl, or heterocarbocyclyl; R.sup.10 is H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, C.sub.1-C.sub.10 alkyl-C(.dbd.O)--, C.sub.2-C.sub.10 alkenyl-C(.dbd.O)--, C.sub.2-C.sub.10 alkynyl-C(.dbd.O)--, carbocyclyl-C(.dbd.O)--, heterocarbocyclyl-C(.dbd.O)--, carbocyclylalkyl-C(.dbd.O)--, heterocarbocyclylalkyl-C(.dbd.O)--, C.sub.1-C.sub.10 alkyl-S(.dbd.O).sub.2--, carbocyclyl-S(.dbd.O).sub.2--, heterocarbocyclyl-S(.dbd.O).sub.2--, carbocyclylalkyl-S(.dbd.O).sub.2--, heterocarbocyclylalkyl-S(.dbd.O).sub.2--, C.sub.1-C.sub.10 alkyl-NHC(.dbd.O)--, carbocyclyl-NHC(.dbd.O)--, heterocarbocyclyl-NHC(.dbd.O)--, carbocyclylalkyl-NHC(.dbd.O)--, heterocarbocyclylalkyl-NHC(.dbd.O)--, C.sub.1-C.sub.10 alkyl-OC(.dbd.O)--, carbocyclyl-OC(.dbd.O)--, heterocarbocyclyl-OC(.dbd.O)--, carbocyclylalkyl-OC(.dbd.O)--, heterocarbocyclylalkyl-OC(.dbd.O)--, C.sub.1-C.sub.10 alkyl-NH--C(.dbd.O)--NHS(.dbd.O).sub.2--, carbocyclyl-NH--C(.dbd.O)--NHS(.dbd.O).sub.2--, heterocarbocyclyl-NH--C(.dbd.O)--NHS(.dbd.O).sub.2--, alkyl-S(.dbd.O).sub.2--NH--C(.dbd.O)--, carbocyclyl-S(.dbd.O).sub.2--NH--C(.dbd.O)--, heterocarbocyclyl-S(.dbd.O).sub.2--NH--C(.dbd.O)--, or an amino protecting group; wherein R.sup.10 is optionally substituted with 1, 2 or 3, R.sup.23; alternatively, R.sup.9 and R.sup.10 together with the N atom to which they are attached form a heterocarbocyclyl group optionally substituted with 1, 2 or 3 R.sup.23; Y is H, --CN, --NO.sub.2, --S(.dbd.O).sub.2R.sup.11, or a guanidino protecting group; R.sup.11 is C.sub.1-C.sub.6 alkyl, aryl, or NR.sup.12R.sup.13; R.sup.12 and R.sup.13 are, independently, H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, or an amino protecting group; alternatively, R.sup.12 and R.sup.13 together with the N atom to which they are attached form a heterocarbocyclyl group; Z is O, S, Se, or Te; Q is --B(OH).sub.2, --B(OR.sup.14).sub.2, or a cyclic boronic ester wherein said cyclic boronic ester contains from 2 to 20 carbon atoms, and, optionally, a heteroatom which can be N, S, or O; R.sup.14 is H, C.sub.1-C.sub.4 alkyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl; X is R.sup.AC(.dbd.O)--, R.sup.ANHC(.dbd.O)--, R.sup.AS(.dbd.O).sub.2--, R.sup.AC(.dbd.O)--, R.sup.ASC(.dbd.O)--, or R.sup.A; morpholino, thiomorpholino, piperazinyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, 1,2,4-thiadiazolyl, isothiazolyl, or purinyl, each optionally substituted with 1-5 R.sup.21; R.sup.20 is selected from the group consisting of: --CN, halo, haloalkyl-, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, --CO.sub.2H, --C(.dbd.O)CO.sub.2H, --C(.dbd.O)NH.sub.2, --C(.dbd.O)H, --S(.dbd.O)NH.sub.2, --S(.dbd.O).sub.2NH.sub.2, --OH, --SH, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)NH.sub.2, --NHC(.dbd.O)R.sup.20a, --NHC(.dbd.O)OR.sup.20a, --OR.sup.20a, --SR.sup.20a, --S(.dbd.O)R.sup.20a, --S(.dbd.O).sub.2R.sup.20a, --S(.dbd.O).sub.2--NHR.sup.20a, --SC(.dbd.O)R.sup.20a, --C(.dbd.O)R.sup.20a, --C(.dbd.O)NHR.sup.20a, --C(.dbd.O)O--R.sup.20a, --NHS(.dbd.O).sub.2R.sup.20a, --NHR.sup.20b, phthalimido, --(O-alkyl).sub.r-OH, --(O-alkyl).sub.r-(O-alkyl), --OR.sup.20c, --SR.sup.20c, --O-alkyl-R.sup.20c, --S-alkyl-R.sup.20c, --S(.dbd.O)--R.sup.20c, --S(.dbd.O).sub.2--R.sup.20c, --S(.dbd.O).sub.2--NHR.sup.20c, --SC(.dbd.O)R.sup.20c, --C(.dbd.O)R.sup.20c, --C(.dbd.O)OR.sup.20c, --C(.dbd.O)NHR.sup.20c, carbocyclyl optionally substituted with 1-5 R.sup.21; and heterocarbocyclyl optionally substituted with 1-5 R.sup.21; R.sup.20a C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, or C.sub.2-C.sub.20 alkynyl; wherein said alkyl, alkenyl, or alkynyl is optionally substituted by one or more halo, OH, CN, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.2-C.sub.8 alkoxyalkoxy, aryl, heteroaryl or --NHR.sup.20b; R.sup.20b is an amino protecting group; R.sup.20c is carbocyclyl optionally substituted with 1-5 R.sup.22; or heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.21 is selected from the group consisting of: C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, C.sub.2-C.sub.20 alkynyl, --OR.sup.21a, --SR.sup.21a, --CN, halo, haloalkyl, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)O-alkyl, --NHC(.dbd.O)alkyl, --COOH, --C(.dbd.O)O-alkyl, --C(.dbd.O)alkyl, --C(O)H, --S(.dbd.O)-alkyl, --S(.dbd.O).sub.2-alkyl, --S(.dbd.O)-aryl, --S(.dbd.O).sub.2-aryl, carbocyclyl optionally substituted with 1-5 R.sup.22, and heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.21a is H, C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, C.sub.2-C.sub.20 alkynyl, carbocyclyl or heterocarbocyclyl; R.sup.22 is selected from the group consisting of: C.sub.1-C.sub.10 alkyl, C.sub.2-C.sub.10 alkenyl, C.sub.2-C.sub.10-alkynyl, phenyl, halo, haloalkyl, alkoxy, thialkoxy, amino, alkylamino, dialkylamino, carboxyl, alkyl-OC(.dbd.O)--, alkyl-C(.dbd.O)--, aryl-OC(.dbd.O)--, alkyl-OC(.dbd.O)NH--, aryl-OC(.dbd.O)NH--, alkyl-C(.dbd.O)NH--, alkyl-C(.dbd.O)O--, (alkyl-O).sub.r-alkyl, HO-(alkyl-O).sub.r-alkyl-, --OH, --SH, --CN, --N.sub.3, --CNO, --CNS, alkyl-S(.dbd.O)--, alkyl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O)--, and H.sub.2NS(.dbd.O).sub.2--; R.sup.23 is selected from the group consisting of: C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, F, Cl, Br, I, haloalkyl, --NH.sub.2, --NHR.sup.23a, --N(R.sup.23a).sub.2, N.sub.3, --NO.sub.2, --CN, --CNO, --CNS, --C(.dbd.O)OR.sup.23a, --C(.dbd.O)R.sup.23a, --OC(.dbd.O)R.sup.23a, --N(R.sup.23a)C(.dbd.O)R.sup.23a, --N(R.sup.23a)C(.dbd.O)OR.sup.23a, --C(.dbd.O)N(R.sup.23a).sub.2, ureido, --OR.sup.23a, --SR.sup.23a, --S(.dbd.O)--(C.sub.1-C.sub.6 alkyl), --S(.dbd.O).sub.2--(C.sub.1-C.sub.6 alkyl), --S(.dbd.O)-aryl, --S(.dbd.O).sub.2-aryl, --S(.dbd.O).sub.2--N(R.sup.23a).sub.2; carbocyclyl optionally substituted with 1-5 R.sup.24; and heterocarbocyclyl optionally substituted with 1-5 R.sup.24; R.sup.23a is H or C.sub.1-C.sub.6 alkyl; alternatively, two R.sup.23a may be combined, together with the N atom to which they are attached, to form a 5 to 7 membered heterocyclic group; and R.sup.24 is selected from the group consisting of: C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, phenyl, halo, haloalkyl, alkoxy, thialkoxy, amino, alkylamino, dialkylamino, carboxyl, alkyl-OC(.dbd.O)--, alkyl-C(.dbd.O)--, aryl-OC(.dbd.O)--, alkyl-OC(.dbd.O)NH--, aryl-OC(.dbd.O)NH--, alkyl-C(.dbd.O)NH--, alkyl-C(.dbd.O)O--, (alkyl-O).sub.r-alkyl, HO-(alkyl-O).sub.r-alkyl-, --OH, --SH, --CN, --N.sub.3, --CNO, --CNS, alkyl-S(.dbd.O)--, alkyl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O)--, and H.sub.2NS(.dbd.O).sub.2--; and r is 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; with the proviso that when Q is a 1,1,2,2-tetramethylethanediol boronic ester, then X is not aralkyloxycarbonyl; and with the proviso that when Q is a 1,1,2,2-tetramethylethanediol boronic ester, and R.sup.1 is cycloalkyl, then R.sup.2 is not --CH.sub.2CONH.sub.2.

2. The compound of claim 1 wherein R.sup.1 is C.sub.1-C.sub.4 alkyl.

3. The compound of claim 1 wherein R.sup.1 is 2-propyl.

4. The compound of claim 1 wherein R.sup.2 is --(CH.sub.2).sub.aCH.sub.2NHC(.dbd.NR.sup.4)NH--Y, --(CH.sub.2).sub.bCH.sub.2CONR.sup.5R.sup.6, --(CH.sub.2).sub.cCH.sub.2N(R.sup.4)CONH.sub.2, --(CH.sub.2).sub.dCH(R.sup.7)NR.sup.9R.sup.10, or --(CH.sub.2).sub.eCH(R.sup.7)ZR.sup.8.

5. The compound of claim 1 wherein R.sup.2 is --(CH.sub.2).sub.aCH.sub.2NHC(.dbd.NR.sup.4)NH--Y.

6. The compound of claim 5 wherein a is 1, 2, 3, or 4.

7. The compound of claim 5 wherein a is 2.

8. The compound of claim 1 wherein R.sup.2 is --(CH.sub.2).sub.dCH(R.sup.7)NR.sup.9R.sup.10.

9. The compound of claim 8 wherein d is 0, 1, or 2.

10. The compound of claim 8 wherein d is 0.

11. The compound of claim 8 wherein R.sup.9 is H.

12. The compound of claim 1 wherein R.sup.2 is --(CH.sub.2).sub.eCH(R.sup.7)ZR.sup.8.

13. The compound of claim 12 wherein Z is O.

14. The compound of claim 13 wherein e is 0, 1, or 2.

15. The compound of claim 13 wherein e is 0.

16. The compound of claim 1 wherein Q is B(OH).sub.2 or a cyclic boronic ester wherein said cyclic boronic ester contains from 6 to 10 carbon atoms and contains at least one cycloalkyl moiety.

17. The compound of claim 16 wherein Q is pinanediol boronic ester.

18. The compound of claim 16 wherein Q is bicyclohexyl-1,1'-diol boronic ester.

19. The compound of claim 16 wherein Q is 1,2-dicyclohexyl-ethane-1,2-diol boronic ester.

20. The compound of claim 1 wherein X is R.sup.AC(.dbd.O)--.

21. The compound of claim 1 wherein X is R.sup.ANHC(.dbd.O)--.

22. The compound of claim 1 wherein X is R.sup.AS(.dbd.O).sub.2--.

23. The compound of claim 1 wherein R.sup.2 is --CH.sub.2NH--C(.dbd.O)OCH.sub.2(C.sub.6H.sub.5).

24. A compound of claim 1 of Formula (I): ##STR00683## or pharmaceutically acceptable salt, stereoisomeric or tautomeric form thereof, wherein: R.sup.1 is C.sub.1-C.sub.8 alkyl, C.sub.2-C.sub.8 alkenyl, C.sub.2-C.sub.8 alkynyl, or C.sub.3-C.sub.7 cycloalkyl; R.sup.2 is --(CH.sub.2).sub.aCH.sub.2NHC(.dbd.NR.sup.4)NH--Y, --(CH.sub.2).sub.bCH.sub.2CONR.sup.5R.sup.6, --(CH.sub.2).sub.cCH.sub.2N(R.sup.4)CONH.sub.2, --(CH.sub.2).sub.dCH(R.sup.7)NR.sup.9R.sup.10, or --(CH.sub.2).sub.eCH(R.sup.7)ZR.sup.8; a, b, and c are each, independently, 0, 1, 2, 3, 4, 5, or 6; d and e are each, independently, 0, 1, 2, 3, or 4; R.sup.4 is H or C.sub.1-C.sub.10 alkyl; R.sup.5 and R.sup.6 are each, independently, H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, or an amino protecting group; alternatively, R.sup.5 and R.sup.6 together with the N atom to which they are attached form a heterocarbocyclyl group; R.sup.7 is H or C.sub.1-C.sub.10 alkyl; R.sup.8 is H, C.sub.1-C.sub.10 alkyl, alkyl-S(.dbd.O).sub.2--, aryl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O).sub.2--, --SO.sub.3H, or a protecting group; R.sup.9 is H, C.sub.1-C.sub.10 alkyl, carbocyclyl, or heterocarbocyclyl; R.sup.10 is H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, C.sub.1-C.sub.10 alkyl-C(.dbd.O)--, carbocyclyl-C(.dbd.O)--, heterocarbocyclyl-C(.dbd.O)--, carbocyclylalkyl-C(.dbd.O)--, heterocarbocyclylalkyl-C(.dbd.O)--, C.sub.1-C.sub.10 alkyl-S(.dbd.O).sub.2--, carbocyclyl-S(.dbd.O).sub.2--, heterocarbocyclyl-S(.dbd.O).sub.2--, carbocyclylalkyl-S(.dbd.O).sub.2--, heterocarbocyclylalkyl-S(.dbd.O).sub.2--, C.sub.1-C.sub.10 alkyl-NHC(.dbd.O)--, carbocyclyl-NHC(.dbd.O)--, heterocarbocyclyl-NHC(.dbd.O)--, carbocyclylalkyl-NHC(.dbd.O)--, heterocarbocyclylalkyl-NHC(.dbd.O)--, C.sub.1-C.sub.10 alkyl-OC(.dbd.O)--, carbocyclyl-OC(.dbd.O)--, heterocarbocyclyl-OC(.dbd.O)--, carbocyclylalkyl-OC(.dbd.O)--, heterocarbocyclylalkyl-OC(.dbd.O)--, or an amino protecting group; wherein R.sup.10 is optionally substituted with 1, 2, or 3 R.sup.23; alternatively, R.sup.9 and R.sup.10 together with the N atom to which they are attached form a heterocarbocyclyl group; Y is --H, --CN, --NO.sub.2, --S(.dbd.O).sub.2R.sup.11, or a guanidino protecting group; R.sup.11 is C.sub.1-C.sub.6 alkyl, aryl, or NR.sup.12R.sup.13; R.sup.12 and R.sup.13 are, independently, H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, or an amino protecting group; alternatively, R.sup.12 and R.sup.13 together with the N atom to which they are attached form a heterocarbocyclyl group; Z is O, S, Se, or Te; Q is --B(OH).sub.2, --B(OR.sup.14).sub.2, or a cyclic boronic ester wherein said cyclic boronic ester contains from 2 to 20 carbon atoms, and, optionally, a heteroatom which can be N, S, or O; R.sup.14 is H, C.sub.1-C.sub.4 alkyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl; X is R.sup.AC(.dbd.O)--, R.sup.ANHC(.dbd.O)--, R.sup.AS(.dbd.O).sub.2--, R.sup.AC(.dbd.O)--, R.sup.ASC(.dbd.O)--, or R.sup.A; R.sup.A is morpholino, thiomorpholino, piperazinyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, 1,2,4-thiadiazolyl, isothiazolyl, or purinyl, each optionally substituted with 1-2 R.sup.21; R.sup.20 is selected from the group consisting of: --CN, halo, haloalkyl-, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, --CO.sub.2H, --C(.dbd.O)CO.sub.2H, --C(.dbd.O)NH.sub.2, --C(.dbd.O)H, --S(.dbd.O)NH.sub.2, --S(.dbd.O).sub.2NH.sub.2, --OH, --SH, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)NH.sub.2, --NHC(.dbd.O)R.sup.20a, --NHC(.dbd.O)OR.sup.20a, --OR.sup.20a, --SR.sup.20a, --S(.dbd.O)R.sup.20a, --S(.dbd.O).sub.2R.sup.20a, --S(.dbd.O).sub.2--NHR.sup.20a, --SC(.dbd.O)R.sup.20a, --C(.dbd.O)R.sup.20a, --C(.dbd.O)NHR.sup.20a, --C(.dbd.O)O--R.sup.20a, --NHS(.dbd.O).sub.2R.sup.20a, --NHR.sup.20b, phthalimido, --(--O-alkyl).sub.r, --O-alkyl-OH, --(O-alkyl).sub.r-OH, --OR.sup.20c, --SR.sup.20c, --S(.dbd.O)--R.sup.20c, --S(.dbd.O).sub.2--R.sup.20c, --S(.dbd.O).sub.2--NHR.sup.20c, --SC(.dbd.O)R.sup.20c, --C(.dbd.O)R.sup.20c, --C(.dbd.O)OR.sup.20c, --C(.dbd.O)NHR.sup.20c, carbocyclyl optionally substituted with 1-5 R.sup.21; and heterocarbocyclyl optionally substituted with 1-5 R.sup.21; R.sup.20a is C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, or C.sub.2-C.sub.20 alkynyl; wherein said alkyl, alkenyl, or alkynyl is optionally substituted by one or more halo, C.sub.1-C.sub.4 alkyl, aryl, heteroaryl or --NHR.sup.20b; R.sup.20b is an amino protecting group; R.sup.20c is carbocyclyl optionally substituted with 1-5 R.sup.22; or heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.21 is selected from the group consisting of: C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, C.sub.2-C.sub.20 alkynyl, C.sub.1-C.sub.20 alkoxy, C.sub.1-C.sub.20 thialkoxy, --OH, --CN, halo, haloalkyl, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)O-alkyl, --NHC(.dbd.O)alkyl, --C(.dbd.O)O-alkyl, --C(.dbd.O)alkyl, --S(.dbd.O)-alkyl, --S(.dbd.O).sub.2-alkyl, --S(.dbd.O)-aryl, --S(.dbd.O).sub.2-aryl, carbocyclyl optionally substituted with 1-5 R.sup.22; and heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.22 is selected from the group consisting of: C.sub.1-C.sub.10 alkyl, C.sub.2-C.sub.10 alkenyl, C.sub.2-C.sub.10 alkynyl, phenyl, halo, haloalkyl, alkoxy, thialkoxy, amino, alkylamino, dialkylamino, carboxyl, alkyl-OC(.dbd.O)--, alkyl-C(.dbd.O)--, aryl-OC(.dbd.O)--, alkyl-OC(.dbd.O)NH--, aryl-OC(.dbd.O)NH--, alkyl-C(.dbd.O)NH--, alkyl-C(.dbd.O)O--, (alkyl-O).sub.r-alkyl, HO-(alkyl-O).sub.r-alkyl-, --OH, --SH, --CN, --N.sub.3, --CNO, --CNS, alkyl-S(.dbd.O)--, alkyl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O)--, and H.sub.2NS(.dbd.O).sub.2--; R.sup.23 is selected from the group consisting of: C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, F, Cl, Br, I, haloalkyl, --NH.sub.2, --NHR.sup.23a, --N(R.sup.23a).sub.2, --N.sub.3, --NO.sub.2, --CN, --CNO, --CNS, --C(.dbd.O)OR.sup.23a, --C(.dbd.O)R.sup.23a, --OC(.dbd.O)R.sup.23a, --N(R.sup.23a)C(.dbd.O)R.sup.23a, --C(.dbd.O)N(R.sup.23a).sub.2, ureido, --OR.sup.23a, --SR.sup.23a, --S(.dbd.O).sub.2--(C.sub.1-C.sub.6 alkyl), --S(.dbd.O).sub.2-aryl, and --S(.dbd.O).sub.2--N(R.sup.23a).sub.2; R.sup.23a is H or C.sub.1-C.sub.6 alkyl; alternatively, two R.sup.23a may be combined, together with the N atom to which they are attached, to form a 5 to 7 membered heterocyclic group; and r is 2, 3, 4, 5, 6, 7, 8, 9, or 10; and with the proviso that when Q is a 1,1,2,2-tetramethylethanediol boronic ester, then X is not aralkyloxycarbonyl; and with the proviso that when Q is a 1,1,2,2-tetramethylethanediol boronic ester, and R.sup.1 is cycloalkyl, then R.sup.2 is not --CH.sub.2CONH.sub.2.

25. The compound of claim 24 wherein R.sup.1 is 2-propyl.

26. The compound of claim 24 wherein Q is --B(OH).sub.2.

27. The compound of claim 24 wherein Q is pinanediol boronic ester.

28. The compound of claim 24 wherein X is R.sup.AC(.dbd.O)--.

29. The compound of claim 24 wherein R.sup.2 is --CH.sub.2NH--C(.dbd.O)OCH.sub.2(C.sub.6H.sub.5).

30. A compound of claim 1 having Formula (I): ##STR00684## or pharmaceutically acceptable salt, stereoisomeric or tautomeric form thereof, wherein: R.sup.1 is C.sub.1-C.sub.8 alkyl; R.sup.2 is --(CH.sub.2).sub.aCH.sub.2NHC(.dbd.NH)NH--Y, --(CH.sub.2).sub.cCH.sub.2NHCONH.sub.2, --(CH.sub.2).sub.dCH(R.sup.7)NR.sup.9R.sup.10, or --(CH.sub.2).sub.eCH(R.sup.7)ZR.sup.8; a is 1, 2, 3, 4, or 5; c is 1, 2, 3, 4, or 5; d is 0, 1, or 2; e is 0, 1, or 2; R.sup.7 is H or methyl; R.sup.8 is H, C.sub.1-C.sub.10 alkyl, --S(.dbd.O).sub.2-alkyl, --S(.dbd.O).sub.2-aryl, --S(.dbd.O).sub.2--NH.sub.2, --SO.sub.3H, or a protecting group; Y is --H, --CN, --NO.sub.2, --S(.dbd.O).sub.2R.sup.11, or a guanidino protecting group; R.sup.9 is H, C.sub.1-C.sub.10 alkyl, carbocyclyl, or heterocarbocyclyl; R.sup.10 is H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, C.sub.1-C.sub.10 alkyl-C(.dbd.O)--, carbocyclyl-C(.dbd.O)--, heterocarbocyclyl-C(.dbd.O)--, carbocyclylalkyl-C(.dbd.O)--, heterocarbocyclylalkyl-C(.dbd.O)--, C.sub.1-C.sub.10 alkyl-S(.dbd.O).sub.2--, carbocyclyl-S(.dbd.O).sub.2--, heterocarbocyclyl-S(.dbd.O).sub.2--, carbocyclylalkyl-S(.dbd.O).sub.2--, heterocarbocyclylalkyl-S(.dbd.O).sub.2--, C.sub.1-C.sub.10 alkyl-NHC(.dbd.O)--, carbocyclyl-NHC(.dbd.O)--, heterocarbocyclyl-NHC(.dbd.O)--, carbocyclylalkyl-NHC(.dbd.O)--, heterocarbocyclylalkyl-NHC(.dbd.O)--, C.sub.1-C.sub.10 alkyl-OC(.dbd.O)--, carbocyclyl-OC(.dbd.O)--, heterocarbocyclyl-OC(.dbd.O)--, carbocyclylalkyl-OC(.dbd.O)--, heterocarbocyclylalkyl-OC(.dbd.O)--, or an amino protecting group; wherein R.sup.10 is optionally substituted with 1, 2 or 3 R.sup.23; alternatively, R.sup.9 and R.sup.10 together with the N atom to which they are attached form a heterocarbocyclyl group; R.sup.11 is C.sub.1-C.sub.6 alkyl, aryl, or NR.sup.12R.sup.13; R.sup.12 and R.sup.13 are, independently, H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, or an amino protecting group; alternatively, R.sup.12 and R.sup.13 together with the N atom to which they are attached form a heterocarbocyclyl group; Z is O or S; Q is --B(OH).sub.2, --B(OR.sup.14).sub.2, or a cyclic boronic ester wherein said cyclic boronic ester contains from 6 to 20 carbon atoms and contains at least one cycloalkyl moiety; R.sup.14 is H, C.sub.1-C.sub.4 alkyl, or cycloalkyl; X is R.sup.AC(.dbd.O)--, R.sup.ANHC(.dbd.O)--, R.sup.AS(.dbd.O).sub.2--, R.sup.AC(.dbd.O)--, R.sup.ASC(.dbd.O)--, or R.sup.A; R.sup.A is morpholino, thiomorpholino, piperazinyl, tetrahydrofuranyl, tetrahydrothienyl, piperidinyl, pyrrolidinyl, isoxazolidinyl, isothiazolidinyl, pyrazolidinyl, oxazolidinyl, thiazolidinyl, imidazolidinyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, furyl, thienyl, imidazolyl, thiazolyl, pyrrolyl, oxazolyl, isoxazolyl, pyrazolyl, triazolyl, tetrazolyl, 1,2,4-thiadiazolyl, isothiazolyl, or purinyl, each optionally substituted with 1-2 R.sup.21; R.sup.20 is selected from the group consisting of: --CN, halo, haloalkyl-, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, --CO.sub.2H, --C(.dbd.O)CO.sub.2H, --C(.dbd.O)NH.sub.2, --C(.dbd.O)H, --S(.dbd.O)NH.sub.2, --S(.dbd.O).sub.2NH.sub.2, --OH, --SH, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)NH.sub.2, --NHC(.dbd.O)R.sup.20a, --NHC(.dbd.O)OR.sup.20a, --OR.sup.20a, --SR.sup.20a, --S(.dbd.O)R.sup.20a, --S(.dbd.O).sub.2R.sup.20a, --S(.dbd.O).sub.2--NHR.sup.20a, --SC(.dbd.O)R.sup.20a, --C(.dbd.O)R.sup.20a, --C(.dbd.O)NHR.sup.20a, --C(.dbd.O)O--R.sup.20a, --NHS(.dbd.O).sub.2R.sup.20a, --NHR.sup.20b, phthalimido, --(O-alkyl).sub.r, --O-alkyl-OH, --(O-alkyl).sub.r-OH, --OR.sup.20c, --SR.sup.20c, --S(.dbd.O)--R.sup.20c, --S(.dbd.O).sub.2--R.sup.20c, --S(.dbd.O).sub.2--NHR.sup.20c, --SC(.dbd.O)R.sup.20c, --C(.dbd.O)R.sup.20c, --C(.dbd.O)OR.sup.20c, --C(.dbd.O)NHR.sup.20c, carbocyclyl optionally substituted with 1-5 R.sup.21; and heterocarbocyclyl optionally substituted with 1-5 R.sup.21; R.sup.20a is C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, or C.sub.2-C.sub.20 alkynyl; wherein said alkyl, alkenyl, or alkynyl is optionally substituted by one or more halo, C.sub.1-C.sub.4 alkyl, aryl, heteroaryl or --NHR.sup.20b; R.sup.20b is an amino protecting group; R.sup.20c is carbocyclyl optionally substituted with 1-5 R.sup.22; or heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.21 is selected from the group consisting of: C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, C.sub.2-C.sub.20 alkynyl, C.sub.1-C.sub.20 alkoxy, C.sub.1-C.sub.20 thialkoxy, --OH, --CN, halo, haloalkyl, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)O-alkyl, --NHC(.dbd.O)alkyl, --C(.dbd.O)O-alkyl, --C(.dbd.O)alkyl, --S(.dbd.O)-alkyl, --S(.dbd.O).sub.2-alkyl, --S(.dbd.O)-aryl, --S(.dbd.O).sub.2-aryl, carbocyclyl optionally substituted with 1-5 R.sup.22, and heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.22 is selected from the group consisting of: C.sub.1-C.sub.10 alkyl, C.sub.2-C.sub.10 alkenyl, C.sub.2-C.sub.10alkynyl, phenyl, halo, haloalkyl, alkoxy, thialkoxy, amino, alkylamino, dialkylamino, carboxyl, alkyl-OC(.dbd.O)--, alkyl-C(.dbd.O)--, aryl-OC(.dbd.O)--, alkyl-OC(.dbd.O)NH--, aryl-OC(.dbd.O)NH--, alkyl-C(.dbd.O)NH--, alkyl-C(.dbd.O)O--, (alkyl-O).sub.r-alkyl, HO-(alkyl-O).sub.r-alkyl-, --OH, --SH, --CN, --N.sub.3, --CNO, --CNS, alkyl-S(.dbd.O)--, alkyl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O)--, and H.sub.2NS(.dbd.O).sub.2--; R.sup.23 is selected from the group consisting of: C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, F, Cl, Br, I, haloalkyl, --NH.sub.2, --NHR.sup.23a, --N(R.sup.23a).sub.2, --N.sub.3, --NO.sub.2, --CN, --CNO, --CNS, --C(.dbd.O)OR.sup.23a, --C(.dbd.O)R.sup.23a, --OC(.dbd.O)R.sup.23a, --N(R.sup.23a)C(.dbd.O)R.sup.23a, --C(.dbd.O)N(R.sup.23a).sub.2, ureido, --OR.sup.23a, --SR.sup.23a, --S(.dbd.O).sub.2--(C.sub.1-C.sub.6 alkyl), --S(.dbd.O).sub.2-aryl, and --S(.dbd.O).sub.2--N(R.sup.23a).sub.2; R.sup.23a is H or C.sub.1-C.sub.6 alkyl; alternatively, two R.sup.23a may be combined, together with the N atom to which they are attached, to form a 5 to 7 membered heterocyclic group; and r is 2, 3, 4, 5, 6, 7, 8, 9, or 10.

31. A compound of claim 1 having Formula (I): ##STR00685## or pharmaceutically acceptable salt, stereoisomeric or tautomeric form thereof, wherein: R.sup.1 is C.sub.1-C.sub.4 alkyl; R.sup.2 is --(CH.sub.2).sub.aCH.sub.2NHC(.dbd.NH)NH--Y, --(CH.sub.2).sub.cCH.sub.2NHCONH.sub.2, or --(CH.sub.2).sub.dCH(R.sup.7)NR.sup.9R.sup.10; a is 1, 2, or 3; c is 1, 2, or 3; d is 0 or 1; R.sup.7 is H or methyl; R.sup.9 is H or C.sub.1-C.sub.10alkyl; R.sup.10 is H, C.sub.1-C.sub.10 alkyl, or an amino protecting group; Y is H, CN, or NO.sub.2; Q is --B(OH).sub.2, pinanediol boronic ester, bicyclohexyl-1,1'-diol boronic ester, or 1,2-dicyclohexyl-ethane-1,2-diol boronic ester; X is R.sup.AC(.dbd.O)--, R.sup.ANHC(.dbd.O)--, R.sup.AS(.dbd.O).sub.2--, R.sup.AC(.dbd.O)--, R.sup.ASC(.dbd.O)--, or R.sup.A; R.sup.20 is selected from the group consisting of: --CN, halo, haloalkyl-, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, --CO.sub.2H, --C(.dbd.O)CO.sub.2H, --C(.dbd.O)NH.sub.2, --C(.dbd.O)H, --S(.dbd.O)NH.sub.2, --S(.dbd.O).sub.2NH.sub.2, --OH, --SH, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)NH.sub.2, --NHC(.dbd.O)R.sup.20a, --NHC(.dbd.O)OR.sup.20a, --OR.sup.20a, --SR.sup.20a, --S(.dbd.O)R.sup.20a, --S(.dbd.O).sub.2R.sup.20a, --S(.dbd.O).sub.2--NHR.sup.20a, --SC(.dbd.O)R.sup.20a, --C(.dbd.O)R.sup.20a, --C(.dbd.O)NHR.sup.20a, --C(.dbd.O)O--R.sup.20a, --NHS(.dbd.O).sub.2R.sup.20a, --NHR.sup.20b, phthalimido, --(O-alkyl).sub.r, --O-alkyl-OH, --(O-alkyl).sub.r-OH, --OR.sup.20c, --SR.sup.20c, --S-alkyl-R.sup.20c, --S(.dbd.O)--R.sup.20c, --S(.dbd.O).sub.2--R.sup.20c, --S(.dbd.O).sub.2--NHR.sup.20c, --SC(.dbd.O)R.sup.20c, --C(.dbd.O)R.sup.20c, --C(.dbd.O)OR.sup.20c, --C(.dbd.O)NHR.sup.20c, carbocyclyl optionally substituted with 1-5 R.sup.21; and heterocarbocyclyl optionally substituted with 1-5 R.sup.21; R.sup.20a is C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, or C.sub.2-C.sub.20 alkynyl; wherein said alkyl, alkenyl, or alkynyl is optionally substituted by one or more halo, C.sub.1-C.sub.4 alkyl, aryl, heteroaryl or --NHR.sup.20b; R.sup.20b is an amino protecting group; R.sup.20c is carbocyclyl optionally substituted with 1-5 R.sup.22; or heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.21 is selected from the group consisting of: C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, C.sub.2-C.sub.20 alkynyl, C.sub.1-C.sub.20 alkoxy, C.sub.1-C.sub.20 thialkoxy, --OH--CN, halo, haloalkyl, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)O-alkyl, --NHC(.dbd.O)alkyl, --C(.dbd.O)O-alkyl, --C(.dbd.O)alkyl, --S(.dbd.O)-alkyl, --S(.dbd.O).sub.2-alkyl, --S(.dbd.O)-aryl, --S(.dbd.O).sub.2-aryl, carbocyclyl optionally substituted with 1-5 R.sup.22, and heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.22 is selected from the group consisting of: C.sub.1-C.sub.10 alkyl, C.sub.2-C.sub.10 alkenyl, C.sub.2-C.sub.10 alkynyl, phenyl, halo, haloalkyl, alkoxy, thialkoxy, amino, alkylamino, dialkylamino, carboxyl, alkyl-OC(.dbd.O)--, alkyl-C(.dbd.O)--, aryl-OC(.dbd.O)--, alkyl-OC(.dbd.O)NH--, aryl-OC(.dbd.O)NH--, alkyl-C(.dbd.O)NH--, alkyl-C(.dbd.O)O--, (alkyl-O).sub.r-alkyl, HO-(alkyl-O).sub.r-alkyl-, --OH, --SH, --CN, --N.sub.3, --CNO, --CNS, alkyl-S(.dbd.O)--, alkyl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O)--, and H.sub.2NS(.dbd.O).sub.2--; and r is 2, 3, 4, or 5; with the proviso that when X is R.sup.AC(.dbd.O)--, R.sup.A is a C.sub.4-C.sub.15 straight-chained alkyl substituted with R.sup.20, and R.sup.20 is --CN, --CO.sub.2H, --C(.dbd.O)O--R.sup.20a, --NHS(.dbd.O).sub.2R.sup.20a, --NHC(.dbd.O)R.sup.20a, --NHR.sup.20b, carbocyclyl, or phthalimido; then R.sup.2 is not --(CH.sub.2).sub.aCH.sub.2NHC(.dbd.NR.sup.4)NH--Y, wherein Y is H, --CN, or --NO.sub.2.

32. The compound of claim 31 wherein R.sup.1 is 2-propyl.

33. The compound of claim 31 wherein Q is --B(OH).sub.2.

34. The compound of claim 31 wherein Q is pinanediol boronic ester.

35. The compound of claim 31 wherein X is R.sup.AC(.dbd.O)--.

36. The compound of claim 31 wherein R.sup.2 is --CH.sub.2NH--C(.dbd.O)OCH.sub.2(C.sub.6H.sub.5).

37. A compound of claim 1 having Formula (I): ##STR00686## or pharmaceutically acceptable salt, stereoisomeric or tautomeric form thereof, wherein: R.sup.1 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, or C.sub.3-C.sub.7 cycloalkyl; R.sup.2 is --CH.sub.2NH.sub.2 or --CH.sub.2NR.sup.9R.sup.10; R.sup.9 is H or C.sub.1-C.sub.10alkyl; R.sup.10 is H, C.sub.1-C.sub.10 alkyl, carbocyclyl, heterocarbocyclyl, C.sub.1-C.sub.10 alkyl-C(.dbd.O)--, carbocyclyl-C(.dbd.O)--, heterocarbocyclyl-C(.dbd.O)--, carbocyclylalkyl-C(.dbd.O)--, heterocarbocyclylalkyl-C(.dbd.O)--, C.sub.1-C.sub.10alkyl-S(.dbd.O).sub.2--, carbocyclyl-S(.dbd.O).sub.2--, heterocarbocyclyl-S(.dbd.O).sub.2--, carbocyclylalkyl-S(.dbd.O).sub.2--, heterocarbocyclylalkyl-S(.dbd.O).sub.2--, C.sub.1-C.sub.10 alkyl-NHC(.dbd.O)--, carbocyclyl-NHC(.dbd.O)--, heterocarbocyclyl-NHC(.dbd.O)--, carbocyclylalkyl-NHC(.dbd.O)--, heterocarbocyclylalkyl-NHC(.dbd.O)--, C.sub.1-C.sub.10 alkyl-OC(.dbd.O)--, carbocyclyl-OC(.dbd.O)--, heterocarbocyclyl-OC(.dbd.O)--, carbocyclylalkyl-OC(.dbd.O)--, heterocarbocyclylalkyl-OC(.dbd.O)--, or an amino protecting group; wherein R.sup.10 is optionally substituted with 1, 2 or 3, R.sup.23; alternatively, R.sup.9 and R.sup.10 together with the N atom to which they are attached form a heterocarbocyclyl group; Q is --B(OH).sub.2, --B(OR.sup.14).sub.2, or a cyclic boronic ester wherein said cyclic boronic ester contains from 2 to 20 carbon atoms, and, optionally, a heteroatom which can be N, S, or O; R.sup.14 is H, C.sub.1-C.sub.4 alkyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl; X is R.sup.AC(.dbd.O)--, R.sup.ANHC(.dbd.O)--, R.sup.AS(.dbd.O).sub.2--, R.sup.AC(.dbd.O)--, R.sup.ASC(.dbd.O)--, or R.sup.A; R.sup.20 is selected from the group consisting of: --CN, halo, haloalkyl-, C.sub.1-C.sub.4 alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, --CO.sub.2H, --C(.dbd.O)CO.sub.2H, --C(.dbd.O)NH.sub.2, --C(.dbd.O)H, --S(.dbd.O)NH.sub.2, --S(.dbd.O).sub.2NH.sub.2, --OH, --SH, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)NH.sub.2, --NHC(.dbd.O)R.sup.20a, --NHC(.dbd.O)OR.sup.20a, --OR.sup.20a, --SR.sup.20a, --S(.dbd.O)R.sup.20a, --S(.dbd.O).sub.2R.sup.20a, --S(.dbd.O).sub.2--NHR.sup.20a, --SC(.dbd.O)R.sup.20a, --C(.dbd.O)R.sup.20a, --C(.dbd.O)NHR.sup.20a, --C(.dbd.O)O--R.sup.20a, --NHS(.dbd.O).sub.2R.sup.20a, --NHR.sup.20b, phthalimido, --(O-alkyl).sub.r, --O-alkyl-OH, --(O-alkyl).sub.r-OH, --OR.sup.20c, --SR.sup.20c, --S(.dbd.O)--R.sup.20c, --S(.dbd.O).sub.2--R.sup.20c, --S(.dbd.O).sub.2--NHR.sup.20c, --SC(.dbd.O)R.sup.20c, --C(.dbd.O)R.sup.20c, --C(.dbd.O)OR.sup.20c, --C(.dbd.O)NHR.sup.20c, carbocyclyl optionally substituted with 1-5 R.sup.21; and heterocarbocyclyl optionally substituted with 1-5 R.sup.21; R.sup.20a is C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, or C.sub.2-C.sub.20 alkynyl; wherein said alkyl, alkenyl, or alkynyl is optionally substituted by one or more halo, C.sub.1-C.sub.4 alkyl, aryl, heteroaryl or --NHR.sup.20b; R.sup.20b is an amino protecting group; R.sup.20c is carbocyclyl optionally substituted with 1-5 R.sup.22; or heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.21 is selected from the group consisting of: C.sub.1-C.sub.20 alkyl, C.sub.2-C.sub.20 alkenyl, C.sub.2-C.sub.20 alkynyl, C.sub.1-C.sub.20 alkoxy, C.sub.1-C.sub.20 thialkoxy, --OH--CN, halo, haloalkyl, --NH.sub.2, --NH(alkyl), --N(alkyl).sub.2, --NHC(.dbd.O)O-alkyl, --NHC(.dbd.O)alkyl, --C(.dbd.O)O-alkyl, --C(.dbd.O)alkyl, --S(.dbd.O)-alkyl, --S(.dbd.O).sub.2-alkyl, --S(.dbd.O)-aryl, --S(.dbd.O).sub.2-aryl, carbocyclyl optionally substituted with 1-5 R.sup.22, and heterocarbocyclyl optionally substituted with 1-5 R.sup.22; R.sup.22 is selected from the group consisting of: C.sub.1-C.sub.10 alkyl, C.sub.2-C.sub.10 alkenyl, C.sub.2-C.sub.10alkynyl, phenyl, halo, haloalkyl, alkoxy, thialkoxy, amino, alkylamino, dialkylamino, carboxyl, alkyl-OC(.dbd.O)--, alkyl-C(.dbd.O)--, aryl-OC(.dbd.O)--, alkyl-OC(.dbd.O)NH--, aryl-OC(.dbd.O)NH--, alkyl-C(.dbd.O)NH--, alkyl-C(.dbd.O)O--, (alkyl-O).sub.r-alkyl, HO-(alkyl-O).sub.r-alkyl-, --OH, --SH, --CN, --N.sub.3, --CNO, --CNS, alkyl-S(.dbd.O)--, alkyl-S(.dbd.O).sub.2--, H.sub.2NS(.dbd.O)--, and H.sub.2NS(.dbd.O).sub.2--; R.sup.23 is selected from the group consisting of: C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, F, Cl, Br, I, haloalkyl, --NH.sub.2, --NHR.sup.23a, --N(R.sup.23a).sub.2, --N.sub.3, --NO.sub.2, --CN, --CNO, --CNS, --C(.dbd.O)OR.sup.23a, --C(.dbd.O)R.sup.23a, --OC(.dbd.O)R.sup.23a, --N(R.sup.23a)C(.dbd.O)R.sup.23a, --C(.dbd.O)N(R.sup.23a).sub.2, ureido, --OR.sup.23a, --SR.sup.23a, --S(.dbd.O).sub.2--(C.sub.1-C.sub.6 alkyl), --S(.dbd.O).sub.2-aryl, and --S(.dbd.O).sub.2--N(R.sup.23a).sub.2; R.sup.23a is H or C.sub.1-C.sub.6 alkyl; alternatively, two R.sup.23a may be combined, together with the N atom to which they are attached, to form a 5 to 7 membered heterocyclic group; and r is 2, 3, 4, or 5.

38. The compound of claim 37 wherein R.sup.1 is 2-propyl.

39. The compound of claim 37 wherein Q is --B(OH).sub.2.

40. The compound of claim 37 wherein Q is pinanediol boronic ester.

41. The compound of claim 37 wherein X is R.sup.AC(.dbd.O)--.

42. The compound of claim 37 wherein R.sup.2 is --CH.sub.2NH--C(.dbd.O)OCH.sub.2(C.sub.6H.sub.5).

43. A compound of claim 1 of Formula (I): ##STR00687## or pharmaceutically acceptable salt, stereoisomeric or tautomeric form thereof, wherein: R.sup.1 is 2-propyl; R.sup.2 is --CH.sub.2CH.sub.2CH.sub.2NHC(.dbd.NH)NH--NO.sub.2, --CH.sub.2CH.sub.2CH.sub.2NHC(.dbd.O)NH.sub.2, --CH(CH.sub.3)OH, --CH.sub.2CONH.sub.2, --CH.sub.2NH.sub.2, or --CH.sub.2NR.sup.9R.sup.10; R.sup.9 is H; R.sup.10 is methyl-C(.dbd.O)--, ethyl-C(.dbd.O)--, propyl-C(.dbd.O)--, butyl-C(.dbd.O)--, pentyl-C(.dbd.O)--, 2-(ethoxycarbonyl)ethyl-C(.dbd.O)--, 4-methyl-phenyl-C(.dbd.O)--, cyclopropyl-C(.dbd.O)--, 4-fluoro-phenyl-C(.dbd.O)--, 4-H.sub.2NSO.sub.2-phenyl-C(.dbd.O)--, 4-H.sub.3CSO.sub.2-phenyl-C(.dbd.O)--, 4-phenyl-phenyl-C(.dbd.O)--, 3,4-dimethoxy-benzyl-C(.dbd.O)--, 3-pyridinyl-C(.dbd.O)--, 2-(hydroxy)-pyridin-3-yl-C(.dbd.O)--, 6-(morpholino)-pyridin-3-yl-C(.dbd.O)--, 2-(pyridin-4-yl)thiazol-4-yl-C(.dbd.O)--, 2-pyrazinyl-C(.dbd.O)--, 2,5-dimethyl-pyrazolyl-C(.dbd.O)--, N-methyl-2-pyrrolyl-C(.dbd.O)--, 2-pyrrolidinyl-C(.dbd.O)--, 2-thiophenyl-C(.dbd.O)--, 5-isoxazolyl-C(.dbd.O)--, 4-(tetrazol-5-yl)phenyl-C(.dbd.O)--, (5-tetrazolyl)CH.sub.2--C(.dbd.O)--, N--H.sub.3CSO.sub.2-piperidinyl-C(.dbd.O)--, butyl-OC(.dbd.O)--, (benzyl)-OC(.dbd.O)--, (9-fluorenylmethyl)-OC(.dbd.O)--, pentyl-NHC(.dbd.O)--, propyl-NHC(.dbd.O)--, phenyl-NHC(.dbd.O)--, 4-methyl-phenyl-NHC(.dbd.O)--, methyl-S(.dbd.O).sub.2--, 4-fluoro-phenyl-S(.dbd.O).sub.2--, 4-cyano-phenyl-S(.dbd.O).sub.2--, 1-methyl-imidazol-4-yl-S(.dbd.O).sub.2--, 2-thiophenyl-S(.dbd.O).sub.2--, (4-methyl-phenyl)-NHC(.dbd.O)NH--S(.dbd.O).sub.2--, and (4-methyl-phenyl)-S(.dbd.O).sub.2NHC(.dbd.O)--, alternatively, R.sup.9 and R.sup.10 together with the N atom to which they are attached form pyrrolyl or pyrazolyl; Q is --B(OH).sub.2, pinanediol boronic ester, bicyclohexyl-1,1'-diol boronic ester, or 1,2-dicyclohexyl-ethane-1,2-diol boronic ester; X is R.sup.AC(.dbd.O)--, R.sup.ANHC(.dbd.O)--, R.sup.AS(.dbd.O).sub.2--, or R.sup.AC(.dbd.O)--; R.sup.A is CH.sub.3--, C.sub.2H.sub.5--, C.sub.3H.sub.7--, C.sub.4H.sub.9--, C.sub.5H.sub.11--, C.sub.6H.sub.13--, C.sub.7H.sub.15--, C.sub.8H.sub.17--, C.sub.9H.sub.19--, C.sub.10H.sub.21--, C.sub.11H.sub.23--, C.sub.12H.sub.25--, C.sub.13H.sub.27--, adamantyl-, bicycloheptanyl-, cyclopropyl substituted with 0-3 R.sup.21; cyclopentyl substituted with 0-2 R.sup.21; cyclohexyl substituted with 0-2 R.sup.21; pyrazinyl substituted with 0-1 R.sup.21; imidazolyl substituted with 0-1 R.sup.21; tetrahydrofuranyl substituted with 0-1 R.sup.21; oxothiazolidinyl substituted with 0-1 R.sup.21; thiazolyl substituted with 0-2 R.sup.21; furanyl substituted with 0-2 R.sup.21; pyrrolidinyl substituted with 0-1 R.sup.21; piperidinyl substituted with 0-1 R.sup.21; piperazinyl substituted with 0-1 R.sup.21; or pyridinyl substituted with 0-1 R.sup.21; R.sup.20 is selected from the group consisting of: hydroxy-, methoxy-, ethoxy-, propoxy-, butoxy-, pentoxy-, hexyloxy-, heptyloxy-, octyloxy-, methoxyethoxy-, methoxyethoxyethoxy-, methyl-S--, ethyl-S--, octyl-S--, methyl-C(.dbd.O)S--, (acetylamino)methyl-S--, amino-, methylamino-, dimethylamino-, methyl-C(.dbd.O)--, phenyl-C(.dbd.O)--, (H.sub.3CSO.sub.2)phenyl-C(.dbd.O)--, thiophenyl-C(.dbd.O)--, methyl-OC(.dbd.O)--, ethyl-OC(.dbd.O)--, butyl-OC(.dbd.O)NH--, methyl-C(.dbd.O)NH--, methoxyethoxy-methyl-C(.dbd.O)NH--, H.sub.2NC(.dbd.O)--, methyl-NHC(.dbd.O)--, ethyl-NHC(.dbd.O)--, propyl-NHC(.dbd.O)--, phenyl-NHC(.dbd.O)--, H.sub.2NC(.dbd.O)NH--, H.sub.2NS(.dbd.O).sub.2--, octyl-S(.dbd.O).sub.2--, phenyl-S(.dbd.O).sub.2--, methylphenyl-S(.dbd.O).sub.2--, thiophenyl-S(.dbd.O).sub.2--, cyclopentyl-, cyclohexyl-, cycloheptyl-, adamantyl-, bicycloheptanyl-, cyclopentenyl-, phenyl-, methoxy-phenyl-, methyl-phenyl-, dimethyl-phenyl-, ethyl-phenyl-, propyl-phenyl-, butyl-phenyl-, fluoro-phenyl-, difluoro-phenyl-, chloro-phenyl-, bromo-phenyl-, iodo-phenyl-, dimethylamino-phenyl-, cyclohexyloxy-, 2-isopropyl-5-methyl-cyclohexyloxy-, naphthyl-, methoxynaphthyl-, naphthyloxy-, phenoxy-, (methyl-phenyl)oxy-, (ethyl-phenyl)oxy-, (propyl-phenyl)oxy-, (butyl-phenyl)oxy-, (fluoro-phenyl)oxy-, (chloro-phenyl)oxy-, (bromo-phenyl)oxy-, naphthyl-S--, benzyl-S--, (methyl-phenyl)methyl-S--, pyrimidinyl-S--, piperidinyl-, N-methyl-piperidinyl, N-propyl-piperidinyl-, phthalimido-, thiophenyl-, methyl-thiophenyl-, imidazolyl-, furanyl-, tetrazolyl-, oxopyrrolidinyl-, indolyl-, and methyl-indolyl-; and R.sup.21 is selected from the group consisting of: methyl-, ethyl-, propyl-, butyl-, pentyl-, hexyl-, heptyl-, ethenyl-, propenyl-, butenyl-, methoxy-, ethoxy-, propoxy-, phenoxy-, fluoro-, chloro-, bromo-, methyl-C(.dbd.O)--, butyl-OC(.dbd.O)--, butyl-OC(.dbd.O)NH--, phenyl-, methoxyphenyl-, fluorophenyl-, chlorophenyl-, bromophenyl-, pyrrolyl-, and pyridinyl-.

44. A compound selected from: TABLE-US-00033 Example No Compound Name D.1.1 Naphthalen-2-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.1.2 2-Pyrazinecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl]- D.1.3 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propanamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.1.4 4-Butylbenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.1.5 3-[(1,1-dimethylethoxy)carbonylamino]benzamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl]- D.1.6 2-(2-methoxyethoxy) acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl D.1.7 2-[2-(2-methoxyethoxy)ethoxy]acetamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl D.1.8 (E)-3-(Ethoxycarbonyl)acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.1.9 2-Piperidin-1-yl-acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.1.10 4-(1-Methyl-piperidin-4-yl)-butanamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.1.11 2-Acetylamino-acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.2.1 4-(methoxycarbonyl)butanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.2.2 4-(1-Butyl-piperidin-4-yl)-butanamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.2.3 2-Butoxyacetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.1 Decanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.2 Naphthalen-1-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.3 2-Phenylacetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.4 1-Phenylcyclopentanecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.5 (2R)-2-Phenylbutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.6 (2S)-2-Phenylbutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.7 Dodecanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.8 Octanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.9 Acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.10 4-(1,1-Dimethylethyl)cyclohexanecarboxamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.11 trans-4-Pentylcyclohexanecarboxamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.12 4-Phenylbutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.13 2-(3-Methoxyphenyl)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.14 4-(1,1-Dimethylethyl)benzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.15 Nonanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.16 (RS)-2-Cyclopentylhexanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.17 Thiophene-2-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.18 2,3-Difluorobenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.19 2-(2-Iodophenyl)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl D.3.20 Cyclohexanecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.21 2-(4-Bromophenyl)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.22 Benzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.23 2-Methylbenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.24 4-Bromobenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.25 (2S)-2-Phenylpropanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.26 (E)-2-Methyl-3-phenyl-acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.27 2-[(Naphthalen-2-yl)oxy]acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.28 2,2-Dimethylbutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.29 2-(2-Chlorophenyl)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.30 5-Methylthiophene-2-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.31 cis-3-(2-Methoxyphenyl)acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.32 (2-Methylphenoxy)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.33 2-(2,5-Dimethylphenyl)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.34 trans-3-(2-Bromophenyl)acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.35 4-Isopropylbenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.36 4-(4-methylphenyl)butanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.37 2-(2-Naphthylsulfanyl)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.38 5-Methylhexanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.39 3-Thiophen-2-yl-propanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.40 2,4-Dimethylthiazole-5-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.41 Furan-3-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.42 (2R)-2-Phenylpropanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.43 2-Cycloheptylacetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.44 1-Methylcyclopropanecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.45 1-Methyl-cyclohexanecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.46 2-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyl]oxyacetamide, N-[(1S)-1- [[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.47 (E)-2-Butenamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.48 3-Methylbutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.49 3-Phenylpropanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.50 4-(4-Methoxyphenyl)-butanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.51 Thiophene-3-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.52 2-Thiophen-3-yl-acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl D.3.53 (E)-Penta-2,4-dienoic acid amide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-

hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.54 2-(4-Isopropylphenoxy)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.55 2-(4-Ethylphenoxy)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.56 (E)-2-Methylhex-2-enoic acid amide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.57 3-(3-Methylphenyl)acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.58 2-Adamantan-1-ylacetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.59 (RS)-2-Cyclopent-2-enylacetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl D.3.60 4-Diethylaminobenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.61 (RS)-2-Methylbutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.62 3-(4-Methylphenyl)acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.63 Hexa-2,4-dienoic acid amide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.64 4-Pyrrol-1-yl-benzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.65 (E)-3-Thiophen-3-yl-acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.66 Hept-2-enamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.67 2-(3,4-Dimethylphenoxy)acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.68 Dec-9-enamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.69 (E)-Undec-2-enoic acid amide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.70 (E)-Dec-3-enoic acid amide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.71 2,2-Dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxamide, N-[(1S)-1- [[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.72 2-Methylcyclohexanecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.73 5-Cyclohexylpentanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.74 3-Methoxycyclohexanecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.75 (3R)-3,7-Dimethyl-oct-6-enoic acid amide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl D.3.76 3-[(4-methylbenzyl)sulfanyl]propanamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.77 (3S)-3,7-Dimethyl-oct-6-enoic acid amide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.78 (RS)-4-Ethyloctanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.79 5-Fluoro-2-methoxybenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.80 2-(4-Bromophenoxy)-acetamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.81 2-(1-Methyl-1H-indol-3-yl)acetamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.82 Hexahydro-2,5-methanopentalene-3a(1H)-carboxamide, N-[(1S)-1-[[[(1R)- 1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.83 Bicyclo[2.2.1]heptane-2-carboxamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.84 (RS)-2-(4-Chlorophenyl)propionamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.85 (2S)-2-methylbutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.86 (4RS)-1-[(1,1-dimethylethoxy)carbonyl]-piperidine-4-carboxamide, N-[(1S)- 1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano- 1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.87 (RS)-4-Methyloctanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.88 2-Fluoro-5-methylbenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.89 2-(Bicyclo[2.2.1]hept-2-yl)acetamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.90 Cyclopropanecarboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.91 4-Ethoxybenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.92 (E)-3-(4-Bromophenyl)acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.93 (2S)-2-(6-Methoxynaphthalen-2-yl)-propanamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.94 3-Fluoro-4-methoxybenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.95 4-Fluoro-3-methylbenzamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.96 Non-2-enoic acid amide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.97 (E)-3-(Naphthalen-2-yl)acrylamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.98 Quinoline-2-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.99 1-(4-Methoxyphenyl)-cyclopropanecarboxamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.101 3-Butenamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.102 Tetradecanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5- trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.103 3-(1H-Indol-3-yl)-propanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.104 4-Phenoxybutanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.105 5-Oxo-5-phenyl-pentanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.106 (2RS)-1-((1,1-dimethylethoxy)carbonyl)-piperidine-2-carboxamide, N-[(1S)- 1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano- 1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.107 Pyridine-2-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.108 Pyridine-3-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.109 Pyridine-4-carboxamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.110 (2S)-1-((1,1-dimethylethoxy)carbonyl)-piperidine-2-carboxamide, N-[(1S)- 1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano- 1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.111 (2R)-1-((1,1-dimethylethoxy)carbonyl)-piperidine-2-carboxamide, N-[(1S)- 1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano- 1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.112 3,3-Dimethyl-butanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro- 3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.113 4-[(Phenylamino)carbonyl]butanamide, N-[(1S)-1-[[[(1R)-1- [(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2- benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-4- [[imino(nitroamino)methyl]amino]butyl] D.3.114 2,2-Dimethylpentanamide, N-[(1S)-1-[[[(1R)-1-[(3aS,4S,6S,7aR)- hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3- methylbutyl]amino]carbonyl]-4-[[imino(nitroamino)methyl]amino]butyl] D.3.115 5-Thiophen-2-yl-pentanamide, N-[(1S)-1-
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