# US 7,612,059 B2 · Pyrrolidine bicyclic compounds and its derivatives, compositions and methods of use > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,612,059 B2 - Document ID: US7612059B2 - Status: Granted - Kind: B2 - Application number: 11/151,131 - Filed: 2005-06-13 - Published: 2005-12-15 - Granted: 2009-11-03 - Earliest claimed: 2001-06-15 - Assignees: Vicuron Pharmaceuticals Inc. - Inventors: Jeffrey Jacobs; Rakesh K Patel; Jason G Lewis; Dinesh V Patel; Zhengyu Yuan - Web page: https://patentgrep.com/patent/US7612059B2 ## CPC - C07D 207/08: with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms - A61P 31/04: Antibacterial agents - A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 - C07D 401/04: directly linked by a ring-member-to-ring-member bond - C07D 403/04: directly linked by a ring-member-to-ring-member bond - C07D 413/04: directly linked by a ring-member-to-ring-member bond - C07D 417/04: directly linked by a ring-member-to-ring-member bond - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract N-[1-oxo-(optionally 2-aza)-2-alkyl-3-(carboxyl or thiol or hydroxyaminocarbonyl or N-hydroxyformamido)-propyl]-(aryl or heteroaryl)-azacyclo4-7alkanes or thiazacyclo4-7alkanes, salts or prodrugs thereof have interesting properties, e.g., in the treatment or prevention of disorders amenable to treatment by PDF inhibitors, such as treatment of bacterial infections. ## Claims ### Claim 1 A compound according to formula (I): Wherein: R1 is an aryl or heteroaryl which is linked to either the α-or β-position to the ring nitrogen; R2 is hydrogen, halogen or hydroxy; R3 is hydrogen, halogen, C1-10 alkyl, C1-10 heteroalkyl or (R2 and R3) collectively form a C4-7 cycloalkyl, provided that when R3 is halogen, R2 is not hydroxy; X is S; W is NR5 or CR4R5, wherein R4 is hydrogen, halogen, C1-10 alkyl, or C1-10 heteroalkyl and R5 is C1-10 alkyl or (R4 and R5) collectively form a C4-7 cycloalkyl, provided that when W is NR5, R2 and R3 are hydrogen, C1-10 alkyl or heteroalkyl; Y is —COOH, —SH, —N(OH)—CHO or —CO—NH(OH), provided that when Y is —N(OH)CHO or —SH, R2 is hydrogen and R3 is hydrogen, C1-10 alkyl or C1-0 heteroalkyl; n is 1; or a pharmaceutically acceptable salt thereof. ### Claim 2 (depends on 1) The compound of formula (I) according to claim 1, wherein Y is —CO—NH(OH). ### Claim 3 (depends on 1) The compound of formula (I) according to claim 1, wherein X is S, R3 and R4 are hydrogen, R5 is lower alkyl and n is 1. ### Claim 4 (depends on 1) The compound of formula (I) according to claim 1, wherein R1 is hydroxy. ### Claim 5 (depends on 1) The compound of formula (I) according to claim 1, wherein R5 is n-butyl. ### Claim 6 (depends on 1) The compound of formula (I) according to claim 1, wherein R1 is heteroaryl. ### Claim 7 (depends on 1) The compound of formula (I) according to claim 1, wherein the heteroaryl is oxazolyl, thiazolyl, pyridinyl and benzimidazolyl. ### Claim 8 (depends on 1) The compound of formula (I) according to claim 1, wherein the heteroaryl is linked to the α-position to the nitrogen of the azacycloalkane represented in formula (I). ### Claim 9 (depends on 1) The compound of formula (I) according to claim 1, wherein the heteroaryl is oxazolyl. ### Claim 10 (depends on 1) The compound of formula (I) according to claim 1, wherein oxazolyl is substituted by one or two lower alkyl. ### Claim 11 (depends on 1) The compound of formula (I) according to claim 1, wherein the heteroaryl is thiazolyl. ### Claim 12 (depends on 11) The compound of formula (I) according to claim 11, wherein the thiazolyl is substituted by one or two substituents selected from the group consisting of lower alkyl and phenyl. ### Claim 13 (depends on 1) The compound of formula (I) according to claim 1, wherein the heteroaryl is pyridinyl. ### Claim 14 (depends on 1) The compound of formula (I) according to claim 1, wherein the heteroaryl is benzimidazolyl. ### Claim 15 (depends on 1) The compound of formula (I) according to claim 1, wherein R2 is hydrogen and W is N. ### Claim 16 (depends on 15) The compound of formula (I) according to claim 15, wherein R5 is a substituted lower alkyl. ### Claim 17 (depends on 15) The compound of formula (I) according to claim 15, wherein R1 is a heteroaryl. ### Claim 18 (depends on 15) The compound of formula (I) according to claim 15, wherein the heteroaryl is oxazolyl and thiaazolyl. ### Claim 19 (depends on 15) The compound of formula (I) according to claim 15, wherein the heteroaryl is linked to the α-position of the azacycloalkane represented in formula (I). ### Claim 20 (depends on 15) The compound of formula (I) according to claim 15, wherein the heteroaryl is oxazolyl. ### Claim 21 (depends on 15) The compound of formula (I) according to claim 15, wherein the heteroaryl is thiazolyl. ### Claim 22 (depends on 21) The compound of formula (I) according to claim 21, wherein the thiazolyl is substituted with phenyl. ### Claim 23 (depends on 1) The compound of formula (I) according to claim 1, wherein R1 is an aryl. ### Claim 24 (depends on 23) The compound of formula (I) according to claim 23, wherein the aryl is a phenyl. ### Claim 25 (depends on 1) The compound of formula (I) according to claim 1, wherein R2 is halogen. ### Claim 26 (depends on 25) The compound of formula (I) according to claim 25, wherein the halogen is fluorine. ### Claim 27 (depends on 1) The compound of formula (I) according to claim 1 wherein the compound is selected from the group consisting of 2 (S)-hydroxy-3 (R)-[2 (S)-oxazol-2-yl-pyrrolidine-1-carbonyl)-heptanoic acid hydroxamide, N-hydroxy-N-[2-(2-oxazol-2-yl-pyrrolidine-1-carbonyl)-hexyl]-formamide, 2 (S)-hydroxy-3 (R)-[2 (S)-(5-methyl-oxazol-2-yl-pyrrolidine-1-carbonyl)-heptanoic acid hydroxamide, and 2 (S)-fluoro-3-(R)-[2-S-(5-methyloxazol-2-yl-pyrrolidine-1-carbonyl)-heptanoic acid hydroxamide. ### Claim 28 (depends on 1) A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier. ### Claim 29 (depends on 1) A method for inhibiting bacteria comprising contacting said bacteria with a bacteria inhibiting amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.