Claims for Patent: 10,640,507

Summary for Patent: 10,640,507

Title:	PBD antibacterial agents
Abstract:	The invention relates to pyrrolobenzodiazepines compounds (PBDs) and to pharmaceutically acceptable salts thereof, which are useful as medicaments, in particular, to treat bacterial infections. The PBDs are compounds of formula (I): and salts and solvates thereof; wherein: dotted lines indicates the optional presence of a double bond; X, X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are connecting functional groups; L is C.sub.1-12 alkylene; R.sub.4, R.sub.5 and R.sub.6 are independently selected from phenylene, cyclopentanylene, cyclohexanylene, 5- to 9-membered heteroarylene and 5- to 6-membered hetereocyclylene groups, and these groups are optionally substituted with up to three optional substituent groups; R.sub.7 is selected from N(C.sub.1-6 alkyl)(C.sub.1-6alkyl), 5- to 6-membered nitrogen-containing hetereocyclyl groups, a monosaccharide moiety and an amino monosaccharide moiety wherein these groups are optionally substituted; and R.sub.8 and R.sub.9 either together form a double bond, or are selected from H and OR.sub.14, or R.sub.8 is a prodrug moiety and R.sub.9 is OR.sub.14; m is 0 or 1; with the proviso that when X.sub.4 is C(O)NH then the up to three optional substituents of R.sub.7 are not selected from (CH2).sub.k-CO.sub.2R.sub.12; with the proviso that when X.sub.4 is (CH.sub.2).sub.tO then R.sub.4 is not phenylene, m is 1 and R.sub.6 is not a 5- to 9-membered heteroarylene; and with the proviso that when X.sub.4 is C(O)NH or NHC(O) that R.sub.4 and/or R.sub.6 is not 5- to 9-membered heteroarylene. ##STR00001##
Inventor(s):	Rahman; Khondaker Mirazur (London, GB), Sutton; John Mark (Salisbury, GB), Picconi; Pietro (London, GB)
Assignee:	King\'s College London (GB) Secretary of State for Health and Social Care (GB)
Application Number:	16/061,295
Patent Claims:	1. A compound of formula (I): ##STR00188## and salts and solvates thereof; wherein: the dotted lines indicates the optional presence of a double bond between C1 and C2, or C2 and C3; X is (CR.sub.15R.sub.16).sub.nO, O(CR.sub.15R.sub.16).sub.n, S, NR.sub.15, CR.sub.15R.sub.16, C(O), C(O)NR.sub.15, NR.sub.15C(O), O--C(O) or C(O)--O; X.sub.1 is (CH.sub.2).sub.pO, O(CH.sub.2).sub.p, C(O), NHC(O), C(O)NH or is absent; X.sub.2 is (CH.sub.2).sub.qO, O(CH.sub.2).sub.q, C(O), NHC(O), C(O)NH or is absent; X.sub.3 is (CH.sub.2).sub.sO, O(CH.sub.2).sub.s, C(O), NHC(O), C(O)NH or is absent; X.sub.4 is (CH.sub.2).sub.tO, O(CH.sub.2).sub.v, C(O), NHC(O), or C(O)NH; L is C.sub.1-12 alkylene; R.sub.1 is H, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, OH, CN, .dbd.CHR.sub.17, halogen, CO.sub.2H or CO.sub.2(C.sub.1-6 alkyl); R.sub.2 is H, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, OH, CN, .dbd.CHR.sub.18, halogen, CO.sub.2H or CO.sub.2(C.sub.1-6 alkyl); R.sub.3 is H, F, OH, OC.sub.1-6 alkyl, OCH.sub.2Ph, a monosaccharide moiety or an amino monosaccharide moiety, wherein the monosaccharide and amino monosaccharide moieties may be optionally acetyl substituted; R.sub.4, R.sub.5 and R.sub.6 are independently phenylene, cyclopentanylene, cyclohexanylene, 5- to 9-membered heteroarylene or 5- to 6-membered hetereocyclylene groups, and these groups are optionally substituted with up to three optional substituent groups each independently selected from the group consisting of: OH, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, halogen, (CH.sub.2).sub.j--CO.sub.2R.sub.10 and (CH.sub.2).sub.j--NR.sub.10R.sub.11; R.sub.7 is N(C.sub.1-6 alkyl)(C.sub.1-6 alkyl), 5- to 6-membered nitrogen-containing hetereocyclyl groups, a monosaccharide moiety or an amino monosaccharide moiety, wherein these nitrogen-containing hetereocyclyl groups are optionally substituted with up to three optional substituent groups each independently selected from the group consisting of: OH, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, halogen, (CH.sub.2).sub.k--CO.sub.2R.sub.12, (CH.sub.2).sub.k--NR.sub.12R.sub.13 and a prodrug moiety, and wherein the monosaccharide and amino monosaccharide moieties may be optionally acetyl substituted; R.sub.8 and R.sub.9 either together form a double bond, or are H or OR.sub.14, or R.sub.8 is a prodrug moiety and R.sub.9 is OR.sub.14; m is 0 or 1; j, k, n, p, q, s and t are each independently an integer from 0 to 6; v is an integer from 1 to 6; and each R.sub.10, R.sub.11, R.sub.12, R.sub.13, R.sub.15, R.sub.16, R.sub.17 and R.sub.18 are independently H or C.sub.1-6 alkyl; R.sub.14 is H, C.sub.1-6 alkyl or tetrahydro-2H-pyran-2-yl; with the proviso that when X.sub.4 is C(O)NH then the up to three optional substituents of R.sub.7 are not (CH.sub.2).sub.k--CO.sub.2R.sub.12; with the proviso that when X.sub.4 is (CH.sub.2).sub.tO then R.sub.4 is not phenylene, m is 1 and R.sub.6 is not a 5- to 9-membered heteroarylene; and with the proviso that when X.sub.4 is C(O)NH or NHC(O) that R.sub.4, R.sub.6, or both R.sub.4 and R.sub.6 are not 5- to 9-membered heteroarylene. 2. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein: R.sub.3 is H, OH, OC.sub.1-6 alkyl or OCH.sub.2Ph; R.sub.7 is N(C.sub.1-6 alkyl)(C.sub.1-6 alkyl) or 5- to 6-membered nitrogen-containing hetereocyclyl groups, and these hetereocyclyl groups are optionally substituted with up to three optional substituent groups each independently selected from the group consisting of: OH, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, halogen, (CH.sub.2).sub.k--CO.sub.2R.sub.12 and (CH.sub.2).sub.k--NR.sub.12R.sub.13; R.sub.8 and R.sub.9 either together form a double bond, or are H or OR.sub.14; and R.sub.14 is H or C.sub.1-6 alkyl. 3. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein R.sub.1 is H. 4. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein R.sub.2 is H. 5. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein R.sub.3 is OCH.sub.3 or OCH.sub.2CH.sub.3. 6. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein R.sub.4 is phenylene, cyclopentanylene, cyclohexanylene, pyrrolylene, N-methylpyrrolylene, furanylene, thiophenyenel, N-methylimidazolylene, imidazolylene, triazolylene, oxazolylene, oxadiazolylene, thiazolylene, pyridinylene, indolylene, N-methylindolylene, benzofuranylene, benzothiophenylene, benzimidazolylene, N-methylbenzoimidazolylene, benzoxazolylene, benzothiazolylene, pyrrolidinylene, tetrahydrofuranylene, tetrahydrothiphenylene, imidazolidinylene, pyrazolidinylene, oxazol idinylene, isoxazolidinylene, thiazolidinylene, isothiazolidinylene, piperidinylene, oxanylene, thianylene, pipazinylene, morpholinylene or thiomorpholinylene groups, and these groups are optionally substituted with up to three optional substituent groups each independently selected from the group consisting of: OH, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, halogen, (CH.sub.2).sub.j--CO.sub.2R.sub.10 and (CH.sub.2).sub.j--NR.sub.10R.sub.11. 7. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein R.sub.5 is phenylene, cyclopentanylene, cyclohexanylene, pyrrolylene, N-methylpyrrolylene, furanylene, thiophenyenel, N-methylimidazolylene, imidazolylene, triazolylene, oxazolylene, oxadiazolylene, thiazolylene, pyridinylene, indolylene, N-methylindolylene, benzofuranylene, benzothiophenylene, benzimidazolylene, N-methylbenzoimidazolylene, benzoxazol ylene, benzothiazolylene, pyrrolidinylene, tetrahydrofuranylene, tetrahydrothiphenylene, imidazolidinylene, pyrazolidinylene, oxazolidinylene, isoxazolidinylene, thiazolidinylene, isothiazolidinylene, piperidinylene, oxanylene, thianylene, pipazinylene, morpholinylene or thiomorpholinylene groups, and these groups are optionally substituted with up to three optional substituent groups independently selected from the group consisting of: OH, C.sub.1-6 alkyl, OC.sub.1-6 alkyl, halogen, (CH.sub.2).sub.j--CO.sub.2R.sub.10 and (CH.sub.2).sub.j--NR.sub.10R.sub.11. 8. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein R.sub.7 is N(C.sub.1-6 alkyl)(C.sub.1-6 alkyl) and 5- to 6-membered nitrogen-containing hetereocyclyl groups selected from pyrrolidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, isoxazolidinyl, thiazolidinyl, isothiazolidinyl, piperidinyl, pipazinyl, morpholinyl or thiomorpholinyl, and these hetereocyclyl groups are optionally substituted with up to three optional substituent groups each independently selected from the group consisting of: OH, C.sub.1-6 alkyl, OC.sub.1-6 alkyl halogen, (CH.sub.2).sub.k--CO.sub.2R.sub.12 and (CH.sub.2).sub.k--NR.sub.12R.sub.13. 9. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein X is O, C(O), C(O)NH or NHC(O). 10. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein X.sub.1 is NHC(O). 11. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein X.sub.2 is NHC(O). 12. A compound of formula (I) and salts and solvates thereof according to a claim 1, wherein X.sub.4 is (CH.sub.2).sub.tO or C(O). 13. A compound of formula (I) and salts and solvates thereof according claim 1, wherein the compound is a compound of formula (IX): ##STR00189## wherein: Y.sub.1 is NH, N(C.sub.1-6 alkyl), S or O; Y.sub.2 is CH, N, S or O; Y.sub.3 is NH, N(C.sub.1-6 S or O; and Y.sub.4 is CH, N, S or O. 14. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein the compound is: (aa) (S)--N-(2-(dimethylcarbamoyl)benzo[b]thiophen-5-yl)-4-(4-((7-methoxy-5-ox- o-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]-diazepin-8-yl)oxy)bu- tanamido)-1-methyl-1H-pyrrole-2-carboxamide ##STR00190## (ab) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo-[e]pyrrolo[1,2-a- ][1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(thiomorpholine-4-carbo- nyl)benzo-furan-5-yl)-1H-pyrrole-2-carboxamide ##STR00191## (ac) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(morpholine-4-carbonyl)b- enzofuran-5-yl)-1H-pyrrole-2-carboxamide ##STR00192## (ad) (S)--N-(2-(dimethylcarbamoyl)benzofuran-5-yl)-4-(4-((7-methoxy-5-oxo-2,3,- 5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]-diazepin-8-yl)oxy)butanami- do)-1-methyl-1H-pyrrole-2-carboxamide ##STR00193## (ae) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo-[e]pyrrolo[1,2-a- ][1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(thiomorpholine-4-carbo- nyl)benzo-[b]thiophen-5-yl)-1H-pyrrole-2-carboxamide ##STR00194## (af) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(morpholine-4-carbonyl)b- enzo[b]-thiophen-5-yl)-1H-pyrrole-2-carboxamide ##STR00195## (ag) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo-[e]pyrrolo[1,2-a- ][1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(piperidine-1-carbonyl)- benzo[b]-thiophen-5-yl)-1H-pyrrole-2-carboxamide ##STR00196## (ah) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo-[e]pyrrolo[1,2-a- ][1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(piperidine-1-carbonyl)- benzofuran-5-yl)-1H-pyrrole-2-carboxamide ##STR00197## (ai) (S)--N-(2-(diethylcarbamoyl)benzofuran-5-yl)-4-(4-((7-methoxy-5-oxo-2,3,5- ,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]-diazepin-8-yl)oxy)butanamid- o)-1-methyl-1H-pyrrole-2-carboxamide ##STR00198## (aj) (S)--N-(2-(diethylcarbamoyl)benzo[b]thiophen-5-yl)-4-(4-((7-methoxy-5-oxo- -2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]-diazepin-8-yl)oxy)but- anamido)-1-methyl-1H-pyrrole-2-carboxamide ##STR00199## (ak) (S)-4-(4-47-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo-[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(thio-morpholine-4-carbo- nyl)benzo-furan-5-yl)-1H-imidazole-2-carboxamide ##STR00200## (al) (1S,4R)-4-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrol- o[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)-N-(2-(thio-morpholine-4-carbony- l)benzofuran-6-yl)cyclohexane-1-carboxamide ##STR00201## (am) (1R,4S)-4-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrol- o[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)-N-(2-(thio-morpholine-4-carbony- l)benzofuran-6-yl)cyclohexane-1-carboxamide ##STR00202## (an) (S)-4-(4-47-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][- 1,4]-diazepin-8-yl)oxy)butanamido)-N-(2-(thiomorpholine-4-carbonyl)benzofu- ran-6-yl)-benzamide ##STR00203## (ao) (S)--N-(2-(dimethylcarbamoyl)benzo[b]-thiophen-5-yl)-4-(4-4-((7-methoxy-5- -oxo-2,3,5,11a-tetrahydro-1H-benzo[e]-imidazole[1,2-a][1,4]diazepin-8-yl)o- xy)butan-amido)-1-methyl-1H-pyrrole-2-carboxamide ##STR00204## (ap) (S)-4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2- -a][1,4]diazepin-8-yl)oxy)butanamido)-1-methyl-1H-pyrrole-2-carboxamido)-N- ,N, 1-trimethyl-1H-pyrrole-2-carboxamide ##STR00205## (aq) (S)--N,N-diethyl-4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[- e]-pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)-1-methyl-1H-pyrrole-2-- carbox-amido)-1-methyl-1H-pyrrole-2-carboxamide ##STR00206## (ar) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(1-methyl-5-(pyrrolidine-1-- carbonyl)-1H-pyrrol-3-yl)-1H-pyrrole-2-carboxamide ##STR00207## (as) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(1-methyl-5-(piperidine-1-c- arbonyl)-1H-pyrrol-3-yl)-1H-pyrrole-2-carboxamide ##STR00208## (at) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(1-methyl-5-(morpholine-4-c- arbonyl)-1H-pyrrol-3-yl)-1H-pyrrole-2-carboxamide ##STR00209## (au) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]diazepin-8-yl)oxy)butanamido)-1-methyl-N-(1-methyl-5-(thiomorpholine-- 4-carbonyl)-1H-pyrrol-3-yl)-1H-pyrrole-2-carboxamide ##STR00210## (av) (S)-4-(4-(4-(4-((7-methoxy-5-oxo-2,3,5, 1 1a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)- -1-methyl-1H-pyrrole-2-carboxamido)phenyl)-N,N, 1-trimethyl-1H-pyrrole-2-carboxamide ##STR00211## (aw) (S)--N,N-diethyl-4-(4-(4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-ben- zo[e]-pyrrolo[1,2-a][1,4]diazepin-8-yl)oxy)butanamido)-1-methyl-1H-pyrrole- -2-carbox-amido)phenyl)-1-methyl-1H-pyrrole-2-carboxamide ##STR00212## (ax) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo-[e]pyrrolo[- 1,2-a][1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(4-(1-methyl-5-(pyrro- lidine-1-carbonyl)-1H-pyrrol-3-yl)phenyl)-1H-pyrrole-2-carboxamide ##STR00213## (ay) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(4-(1-methyl-5-(piperidine-- 1-carbonyl)-1H-pyrrol-3-yl)phenyl)-1H-pyrrole-2-carboxamide ##STR00214## (az) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1- ,2-a][1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(4-(1-methyl-5-(morpho- line-4-carbonyl)-1H-pyrrol-3-yl)phenyl)-1H-pyrrole-2-carboxamide ##STR00215## (ba) (S)-4-(4-((7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(4-(1-methyl-5-(thiomorphol- ine-4-carbonyl)-1H-pyrrol-3-yl)phenyl)-1H-pyrrole-2-carboxamide ##STR00216## (bb) (S)--N-(2-(dimethylcarbamoyl)benzo[b]thiophen-5-yl)-4-(4-47-fluoro-5-oxo-- 2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]-diazepin-8-yl)oxy)buta- namido)-1-methyl-1H-pyrrole-2-carboxamide ##STR00217## (bc) (S)-4-(4-((7-fluoro-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][- 1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-(thiomorpholine-4-carbony- l)-benzofuran-5-yl)-1H-pyrrole-2-carboxamide ##STR00218## (bd) 4-(4-(((S)-7-methoxy-5-oxo-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a]- [1,4]-diazepin-8-yl)oxy)butanamido)-1-methyl-N-(2-((2,4,5-trihydroxy-6-(hy- droxymethyl)-tetrahydro-2H-pyran-3-yl)carbamoyl)benzofuran-5-yl)-1H-pyrrol- e-2-carboxamide ##STR00219## (be) 4-(2-aminopropanamido)benzyl 8-(4-((4-((2-(dimethylcarbamoyl)benzo[b]-thiophen-5-yl)carbamoyl)-1-methy- l-1H-pyrrol-2-yl)amino)-4-oxobutoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a- -tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate ##STR00220## (bf) 4-nitrobenzyl 8-(4-((4-((2-(dimethylcarbamoyl)benzo[b]thiophen-5-yl)-carbamoyl)-1-methy- l-1H-pyrrol-2-yl)amino)-4-oxobutoxy)-7-methoxy-5-oxo-11-((tetrahydro-2H-py- ran-2-yl)oxy)-2,3,11,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin- e-10(5H)-carboxylate (76) ##STR00221## or (bg) 4-nitrobenzyl 8-(4-((4-((2-(dimethylcarbamoyl)benzo[b]thiophen-5-yl)-carbamoyl)-1-methy- l-1H-pyrrol-2-yl)amino)-4-oxobutoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a- -tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepine-10(5H)-carboxylate ##STR00222## 15. A pharmaceutical composition comprising a compound of formula (I) and salts and solvates thereof according to claim 1 and a pharmaceutically acceptable carrier or diluent. 16. A pharmaceutical composition according to claim 15, further comprising an efflux pump inhibitor. 17. A pharmaceutical composition according to claim 15, further comprising an agent for increasing the permeability of bacterial membranes. 18. A kit comprising: (i) a compound of formula (I) and salts and solvates thereof according to claim 1; (ii) an agent for increasing the permeability of bacterial membranes; and/or (ii) an efflux pump inhibitor. 19. A method of treating a condition in a subject, the method comprising administering a therapeutically effective amount of a compound of formula (I) and salts and solvates thereof according to claim 1 or a pharmaceutical composition according to claim 15 to the subject, wherein the condition is the group consisting of: a bacterial infection, a skin infection, pneumonia, a urinary tract infection, a soft tissue injury, sepsis and bacteremia. 20. A method according to claim 19, wherein the condition is a bacterial infection caused by at least one bacterium of selected from the genera Enterococcus, Staphylococcus, Streptococcus, Bacillus, Acinetobacter, Burkholderia, Coxiella, Francisella, Yersina, Klebsiella, Escherichia, Enterobacter or Pseudomonas. 21. A method according to claim 20, wherein the bacterial infection is caused by at least one bacterium of the species Enterococcus faeculis, Enterococcus faecium, Staphylococcus aureus, Streptococcus pyogenes, Streptococcus pneumoniae, Streptococcus agalactiae, Bacillus anthracis, Bacillus cereus, Bacillus subtilis, Haemophilus influenzae, Acinetobacter baumannii, Burkholderia multivorans, Burkholderia cenocepacia, Burkholderia cepacia, Burkholderia mallei, Burkholderia pseudomallei, Coxiella burnetii, Citrobacter freundii, Escherichia coli, Enterobacter cloacae, Enterobacter aerogenes, Francisella tularensis, Yersina pestis, Klebsiella pneumoniae, Serratia marcesens, Salmonella typhi, Salmonella typhimurum, Stenotrophomonas maltophilia, Pseudomonas aeruginosa or Neisseria gonorrhoeae. 22. A compound of formula (I) and salts and solvates thereof according to claim 1, wherein, wherein the monosaccharide and amino monosaccharide moiety is ##STR00223##

Details for Patent 10,640,507

Applicant	Tradename	Biologic Ingredient	Dosage Form	BLA	Approval Date	Patent No.	Expiredate
Emergent Biodefense Operations Lansing Llc	BIOTHRAX	anthrax vaccine adsorbed	Injection	103821	November 12, 1998		2036-12-09