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Details for Patent: 9,284,314

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Details for Patent: 9,284,314

Title:Processes for preparing heterocyclic compounds including trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide and salts thereof
Abstract: The present invention relates to compounds and processes for preparing compounds of Formula (I), ##STR00001## including compounds such as trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide and salts thereof (e.g., NXL-104).
Inventor(s): Ronsheim; Melanie Simone (Port Jefferson, NY), Racha; Saibaba (Smithtown, NY), Lawton; Graham Richard (Smithtown, NY), Zhou; Shao Hong (Commack, NY), Kalyan; Yuriy B. (Staten Island, NY), Golden; Michael (Macclesfield, GB), Milne; David (Macclesfield, GB), Telford; Alexander (Macclesfield, GB), Cherryman; Janette (Macclesfield, GB), Boyd; Alistair (Cheshire, GB), Phillips; Andrew (Macclesfield, GB), Dedhiya; Mahendra G. (Pomona, NY)
Assignee: Forest Laboratories Holdings Ltd. (Hamilton, BM)
Filing Date:Jan 05, 2015
Application Number:14/589,194
Claims:1. A process for preparing a compound of Formula (I): ##STR00067## or a pharmaceutically acceptable salt, solvate, hydrate, enantiomer or diastereomer thereof; comprising (a) treating a compound of Formula (II): ##STR00068## with a source of nitrogen or an amine to prepare a compound of Formula (III): ##STR00069## and (b) treating the compound of Formula (III) with a protecting group and a carbonylation agent; wherein R1, R2, R3, R4, R5, R6 and R7 are identical or different and are independently selected from the group consisting of hydrogen, oxygen, nitrogen, amino, carbonyl, carbamoyl, alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, aryl, aralkyl, trialkylsilyl and heterocycle; wherein each of R1 R2, R3, R4, R5, R6 and R7 is optionally substituted by one or more halogen, oxygen, hydroxy, cyano, nitro, amino, alkyl amino, dialkylamino, arylamino, diarylamino, amido, alkylamido, carbamoyl, ureido, dimethyl amino, carboxyl, alkyl, allyl, halogenated alkyl, trialkylsilyl, alkenyl, alkynyl, cyclo alkyl, cycloalkylalkyl, aryl, arylalkyl, hetero aryl, heteroarylalkyl, heterocycle, hetero cycle alkyl, aroyl, acyl, alkoxy, aryloxy, heteroaryloxy, cycloalkyloxy, cycloalkylalkyloxy, arylalkyloxy, heteroarylalkyloxy, alkylthio, arylthio, alkylsulfinyl, alkylsulfonyl, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl, heteroarylsulfonyl, alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl or a combination thereof; or R1 and R2 together form a heterocycle; optionally substituted by one or more halogen, hydroxy, cyano, nitro, amino, alkyl amino, dialkylamino, arylamino, diarylamino, amido, alkylamido, carbamoyl, ureido, dimethylamino, carboxyl, alkyl, halogenated alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hetero aryl, heteroarylalkyl, heterocycle, heterocyclealkyl, aroyl, acyl, alkoxy, aryloxy, heteroaryloxy, cycloalkyloxy, cycloalkylalkyloxy, arylalkyloxy, heteroarylalkyloxy, alkythio, arylthio, alkylsulfinyl, alkylsulfonyl, arylsulfinyl, arylsulfonyl, heteroarylsulfinyl, heteroarylsulfonyl alkoxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl or a combination thereof; or R3, R5 and R6 are independently COH, COB', COOB', CONH.sub.2, CONHB', CONHOH, CONHSO.sub.2B', CH.sub.2COOH, CH.sub.2COOB', CH.sub.2CONHOH, CH.sub.2CONHCN, CH.sub.2tetrazole, protected CH.sub.2tetrazole, CH.sub.2SO.sub.3H, CH.sub.2SO.sub.2B', CH.sub.2PO(OB').sub.2, CH.sub.2PO(OB')(OH), CH.sub.2PO(B')(OH) and CH.sub.2PO(OH).sub.2; wherein B' is selected from the group consisting of 25 alkyl containing 1 to 6 carbon atoms optionally substituted by a pyridyl or carbamoyl radical, --CHz-alkenyl containing 3 to 9 carbon atoms, aryl containing 6 to 10 carbon atoms and aralkyl containing 7 to 11 carbon atoms, wherein the nucleus of said aryl or aralkyl is optionally substituted by OH, NH.sub.2, NO.sub.2, alkyl containing 1 to 6 carbon atoms, alkoxy containing 1 to 6 carbon atoms or by one or more halogen atoms; or R3, R5 and R6 are independently OR' or OP'; wherein R' is selected from the group consisting of SO.sub.3, SO.sub.2, SO.sub.2NHCOH, SO.sub.2NHCO, SO.sub.2NHCOO, SO.sub.2NHCONH and SO.sub.2NHCONH.sub.2; and R' is optionally substituted by hydrogen or alkyl group optionally substituted by a pyridyl or carbamoyl radical, --CH.sub.2-alkenyl containing 3 to 9 carbon atoms, aryl containing 6 to 10 carbon atoms and aralkyl containing 7 to 11 carbon atoms, wherein the nucleus of said aryl or aralkyl is optionally substituted by OH, NH.sub.2, NO.sub.2, alkyl containing 1 to 6 carbon atoms, alkoxy containing 1 to 6 carbon atoms or by one or more halogen atoms; and P' is selected from the group consisting of PO(OH).sub.2, PO.sub.3, PO.sub.2, PO, PO(OH)(O--), PO.sub.2NHCOH, PO.sub.2NHCO, PO.sub.2NHCOO, PO.sub.2NHCONH and PO.sub.2NHCONH.sub.2; and P' is optionally substituted by hydrogen or alkyl group optionally substituted by a pyridyl or carbamoyl radical, --CH.sub.2-alkenyl containing 3 to 9 carbon atoms, aryl containing 6 to 10 carbon atoms and aralkyl containing 7 to 11 carbon atoms, wherein the nucleus of said aryl or aralkyl is optionally substituted by OH, NH.sub.2, NO.sub.2, alkyl containing 1 to 6 carbon atoms, alkoxy containing 1 to 6 carbon atoms or by one or more halogen atoms.

2. The process of claim 1, wherein R1, R2 and R7 are hydrogen and R3 is OSO.sub.3H.

3. The process of claim 1, wherein R1 is piperidinyl, R2 and R7 are hydrogen and R3 is OSO.sub.3H.

4. The process of claim 1, wherein R4 is benzyloxy.

5. The process of claim 1, wherein R5 is benzyloxy and R6 and R7 are hydrogen.

6. The process of claim 1, wherein R5 is allyl or trialkylsilyl and R6 is hydrogen.

7. The process of claim 1, comprising treating the compound of Formula (III) with 9-fluorenylmethoxycarbonyl.

8. The process of claim 1, comprising treating the compound of Formula (III) with N,N-carbonyl diimidazole.

9. The process of claim 1, further comprising treating the compound formed after treatment of compound of Formula (III) with a SO.sub.3 complex.

10. The process of claim 1, wherein the compound of Formula (I) is trans-7-oxo-6-(sulphooxy)-1,6-diazabicyclo[3,2,1]octane-2-carboxamide or a pharmaceutically acceptable salt thereof.

11. The process of claim 1, wherein the compound of Formula (I) is sodium ({[(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl]oxy}sulphony- l)oxidanide.

12. The process of claim 1, wherein the compound of Formula (II) is benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate.

13. The process of claim 1, wherein the compound of Formula (III) is (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide.

14. The process of claim 13, comprising treating (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide to prepare (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1 octane-2-carboxamide.

15. ({[(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl]oxy}sulp- honyl)oxidanide prepared according to the process of claim 1.
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