JP2006504673A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006504673A5 JP2006504673A5 JP2004529541A JP2004529541A JP2006504673A5 JP 2006504673 A5 JP2006504673 A5 JP 2006504673A5 JP 2004529541 A JP2004529541 A JP 2004529541A JP 2004529541 A JP2004529541 A JP 2004529541A JP 2006504673 A5 JP2006504673 A5 JP 2006504673A5
- Authority
- JP
- Japan
- Prior art keywords
- propyl
- methyl
- methylsulfanyl
- trihydroxy
- pyran
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims 21
- -1 monofluorophenyl Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 18
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 239000000651 prodrug Substances 0.000 claims 5
- 229940002612 prodrug Drugs 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 150000002926 oxygen Chemical class 0.000 claims 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical class 0.000 claims 2
- 125000000623 heterocyclic group Chemical class 0.000 claims 2
- OEHLKONVBIPIML-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound C1C(CCCCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 OEHLKONVBIPIML-UHFFFAOYSA-N 0.000 claims 2
- CXEJVQVBPBUOMW-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpiperidine-2-carboxamide Chemical compound C1C(CCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 CXEJVQVBPBUOMW-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- IZQRFFKFVRLRSR-UHFFFAOYSA-N 1,4-diethyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CC)CCN(CC)C1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 IZQRFFKFVRLRSR-UHFFFAOYSA-N 0.000 claims 1
- PETCMJIKXREIBP-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-(3-methylbutyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1N(CCO)CC(CCC(C)C)C1 PETCMJIKXREIBP-UHFFFAOYSA-N 0.000 claims 1
- VIRFLZJPIAUCQJ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpiperidine-2-carboxamide Chemical compound C1C(CCCCC)CCN(CCO)C1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 VIRFLZJPIAUCQJ-UHFFFAOYSA-N 0.000 claims 1
- FYECSVGQFBINCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound OCCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 FYECSVGQFBINCZ-UHFFFAOYSA-N 0.000 claims 1
- IHORUIJIDJRPCF-UHFFFAOYSA-N 1-(2-hydroxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpiperidine-2-carboxamide Chemical compound C1C(CCC)CCN(CCO)C1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 IHORUIJIDJRPCF-UHFFFAOYSA-N 0.000 claims 1
- QSEHNWXYIRRWPT-UHFFFAOYSA-N 1-(2-hydroxypropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound CC(O)CN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 QSEHNWXYIRRWPT-UHFFFAOYSA-N 0.000 claims 1
- YYOLWMVXPPQURS-UHFFFAOYSA-N 1-(3-hydroxypropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound OCCCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 YYOLWMVXPPQURS-UHFFFAOYSA-N 0.000 claims 1
- MAWGMRQFCUEYCT-UHFFFAOYSA-N 1-methyl-4-propylpyrrolidine-2-carboxylic acid Chemical compound CCCC1CC(C(O)=O)N(C)C1 MAWGMRQFCUEYCT-UHFFFAOYSA-N 0.000 claims 1
- OCZRBRKRQWYHDF-UHFFFAOYSA-N 1-methyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound CN1CC(CCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 OCZRBRKRQWYHDF-UHFFFAOYSA-N 0.000 claims 1
- FYEFLEUMNQBKHG-UHFFFAOYSA-N 2-(1-amino-2-methylpropyl)-6-methylsulfanyloxane-3,4,5-triol Chemical compound CSC1OC(C(N)C(C)C)C(O)C(O)C1O FYEFLEUMNQBKHG-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- SWIMQJKHERFDTI-UHFFFAOYSA-N 4-(2,2-difluoroethyl)-N-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound CC(C(C1OC(C(C(C1O)O)O)SC)NC(=O)C1NCCC(C1)CC(F)F)C SWIMQJKHERFDTI-UHFFFAOYSA-N 0.000 claims 1
- ANZRZTWFDJJFFJ-UHFFFAOYSA-N 4-(2,2-difluoropentyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound C1C(CC(F)(F)CCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 ANZRZTWFDJJFFJ-UHFFFAOYSA-N 0.000 claims 1
- UXSHJWCSFIKOKQ-UHFFFAOYSA-N 4-(2-methylpropyl)piperidine-2-carboxylic acid Chemical compound CC(C)CC1CCNC(C(O)=O)C1 UXSHJWCSFIKOKQ-UHFFFAOYSA-N 0.000 claims 1
- VOXSGVFWNUSDNQ-UHFFFAOYSA-N 4-(3,3-difluorobutyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCC(CCC(C)(F)F)C1 VOXSGVFWNUSDNQ-UHFFFAOYSA-N 0.000 claims 1
- KOKCYWKNDOXBOF-UHFFFAOYSA-N 4-(3,3-difluoropentyl)-1-(2-hydroxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OCCN1CC(CCC(F)(F)CC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 KOKCYWKNDOXBOF-UHFFFAOYSA-N 0.000 claims 1
- SGMPJKZLKVLTPJ-UHFFFAOYSA-N 4-(3,3-difluoropentyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound C1C(CCC(F)(F)CC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 SGMPJKZLKVLTPJ-UHFFFAOYSA-N 0.000 claims 1
- MEWAKMMPJGCDCV-UHFFFAOYSA-N 4-(3,3-difluoropropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCC(F)F)C1 MEWAKMMPJGCDCV-UHFFFAOYSA-N 0.000 claims 1
- QACPDRCQBLJLKD-UHFFFAOYSA-N 4-(3,3-difluoropropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCC(CCC(F)F)C1 QACPDRCQBLJLKD-UHFFFAOYSA-N 0.000 claims 1
- HMAUOONIYWUJOJ-UHFFFAOYSA-N 4-(3-ethyl-3-hydroxypentyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CCC(O)(CC)CC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 HMAUOONIYWUJOJ-UHFFFAOYSA-N 0.000 claims 1
- INWIUDFKJNUSAV-UHFFFAOYSA-N 4-(3-fluoropropoxy)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(OCCCF)CCN1 INWIUDFKJNUSAV-UHFFFAOYSA-N 0.000 claims 1
- MUVCYXZFOSRRBU-UHFFFAOYSA-N 4-(3-methylbutyl)pyrrolidine-2-carboxylic acid Chemical compound CC(C)CCC1CNC(C(O)=O)C1 MUVCYXZFOSRRBU-UHFFFAOYSA-N 0.000 claims 1
- JPGDJWQEAYQZIQ-UHFFFAOYSA-N 4-(4,4-difluorobutyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCC(F)F)C1 JPGDJWQEAYQZIQ-UHFFFAOYSA-N 0.000 claims 1
- PHNLWUOHMQIXNG-UHFFFAOYSA-N 4-(4,4-difluoropentyl)pyrrolidine-2-carboxylic acid Chemical compound CC(F)(F)CCCC1CNC(C(O)=O)C1 PHNLWUOHMQIXNG-UHFFFAOYSA-N 0.000 claims 1
- NHDBLKFYEFBQCW-UHFFFAOYSA-N 4-(4-fluorobutoxy)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(OCCCCF)CCN1 NHDBLKFYEFBQCW-UHFFFAOYSA-N 0.000 claims 1
- WQXFUDJPHDVMJK-UHFFFAOYSA-N 4-(4-fluorobutyl)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(CCCCF)CCN1 WQXFUDJPHDVMJK-UHFFFAOYSA-N 0.000 claims 1
- DKOUTMDQGACRNY-UHFFFAOYSA-N 4-(5,5-difluoropentyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCCC(F)F)C1 DKOUTMDQGACRNY-UHFFFAOYSA-N 0.000 claims 1
- KQAUWOWBMSTFEA-UHFFFAOYSA-N 4-(5-fluoropentyl)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(CCCCCF)CCN1 KQAUWOWBMSTFEA-UHFFFAOYSA-N 0.000 claims 1
- IQPXIMLYBHERPF-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)propyl]pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1CCCC1=CC=C(Cl)C=C1 IQPXIMLYBHERPF-UHFFFAOYSA-N 0.000 claims 1
- FEMWYGGPMJCDPF-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)propyl]pyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1CCCC1=CC=C(F)C=C1 FEMWYGGPMJCDPF-UHFFFAOYSA-N 0.000 claims 1
- YPPFOXPVFKYERL-UHFFFAOYSA-N 4-butoxy-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(OCCCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 YPPFOXPVFKYERL-UHFFFAOYSA-N 0.000 claims 1
- HXKQQDMDSRNRJP-UHFFFAOYSA-N 4-butyl-4-fluoro-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound C1C(CCCC)(F)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 HXKQQDMDSRNRJP-UHFFFAOYSA-N 0.000 claims 1
- YRMDEVIUSAKDKK-UHFFFAOYSA-N 4-butyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CCCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 YRMDEVIUSAKDKK-UHFFFAOYSA-N 0.000 claims 1
- SMZHNCMPICENER-UHFFFAOYSA-N 4-butylpyrrolidine-2-carboxylic acid Chemical compound CCCCC1CNC(C(O)=O)C1 SMZHNCMPICENER-UHFFFAOYSA-N 0.000 claims 1
- XIMAALORQNYIKD-UHFFFAOYSA-N 4-cyclohexyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(C2CCCCC2)C1 XIMAALORQNYIKD-UHFFFAOYSA-N 0.000 claims 1
- QHKALQVBKFZCGF-UHFFFAOYSA-N 4-ethyl-1-(2-hydroxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CC)CCN(CCO)C1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 QHKALQVBKFZCGF-UHFFFAOYSA-N 0.000 claims 1
- HOFQFGGCTRQYCC-UHFFFAOYSA-N 4-ethyl-n-[2-hydroxy-2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CC)CCNC1C(=O)NC(C(C)(C)O)C1C(O)C(O)C(O)C(SC)O1 HOFQFGGCTRQYCC-UHFFFAOYSA-N 0.000 claims 1
- MSDKVRFNKINTES-UHFFFAOYSA-N 4-ethyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 MSDKVRFNKINTES-UHFFFAOYSA-N 0.000 claims 1
- KJQAZPSDPJLGHW-UHFFFAOYSA-N 4-fluoro-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)(F)CNC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 KJQAZPSDPJLGHW-UHFFFAOYSA-N 0.000 claims 1
- QSWMXBBKOQVGOX-UHFFFAOYSA-N 4-fluoro-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)(F)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 QSWMXBBKOQVGOX-UHFFFAOYSA-N 0.000 claims 1
- NBMVWQHQFUVLIB-UHFFFAOYSA-N 4-methoxy-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(OC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 NBMVWQHQFUVLIB-UHFFFAOYSA-N 0.000 claims 1
- IEAKSTUANNJKKK-UHFFFAOYSA-N 4-pentan-3-ylpiperidine-2-carboxylic acid Chemical compound CCC(CC)C1CCNC(C(O)=O)C1 IEAKSTUANNJKKK-UHFFFAOYSA-N 0.000 claims 1
- ILVPWZLDRXLVJF-UHFFFAOYSA-N 4-pentoxypiperidine-2-carboxylic acid Chemical compound CCCCCOC1CCNC(C(O)=O)C1 ILVPWZLDRXLVJF-UHFFFAOYSA-N 0.000 claims 1
- CKQKNXARWQGERL-UHFFFAOYSA-N 5-butyl-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound N1CC(CCCC)CCC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 CKQKNXARWQGERL-UHFFFAOYSA-N 0.000 claims 1
- UZRDREPVAWXHDU-UHFFFAOYSA-N ethyl 2-[[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-4-propylpiperidine-1-carboxylate Chemical compound C1C(CCC)CCN(C(=O)OCC)C1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 UZRDREPVAWXHDU-UHFFFAOYSA-N 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000000813 microbial effect Effects 0.000 claims 1
- NBBHLAMYOMPJAY-UHFFFAOYSA-N n-[2,2-difluoro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-1-(2-hydroxyethyl)-4-pentylpyrrolidine-2-carboxamide Chemical compound OCCN1CC(CCCCC)CC1C(=O)NC(C(C)(F)F)C1C(O)C(O)C(O)C(SC)O1 NBBHLAMYOMPJAY-UHFFFAOYSA-N 0.000 claims 1
- MMOIEPSPQSMDDV-UHFFFAOYSA-N n-[2,2-difluoro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound C1C(CCCCC)CNC1C(=O)NC(C(C)(F)F)C1C(O)C(O)C(O)C(SC)O1 MMOIEPSPQSMDDV-UHFFFAOYSA-N 0.000 claims 1
- WDOHRNQAFLCBHT-UHFFFAOYSA-N n-[2,2-difluoro-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpiperidine-2-carboxamide Chemical compound C1C(CCC)CCNC1C(=O)NC(C(C)(F)F)C1C(O)C(O)C(O)C(SC)O1 WDOHRNQAFLCBHT-UHFFFAOYSA-N 0.000 claims 1
- HQZYUICJBZBJPY-UHFFFAOYSA-N n-[2-hydroxyimino-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide Chemical compound CN1CC(CCC)CC1C(=O)NC(C(C)=NO)C1C(O)C(O)C(O)C(SC)O1 HQZYUICJBZBJPY-UHFFFAOYSA-N 0.000 claims 1
- WUOROAVHTCTLOJ-UHFFFAOYSA-N n-[2-methoxyimino-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide Chemical compound CN1CC(CCC)CC1C(=O)NC(C(C)=NOC)C1C(O)C(O)C(O)C(SC)O1 WUOROAVHTCTLOJ-UHFFFAOYSA-N 0.000 claims 1
- FGLQDRDRUYAVAR-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-(3,3,3-trifluoropropoxy)piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(OCCC(F)(F)F)C1 FGLQDRDRUYAVAR-UHFFFAOYSA-N 0.000 claims 1
- CFWULWXWPMQGGK-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpiperidine-2-carboxamide Chemical compound C1C(CCCCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 CFWULWXWPMQGGK-UHFFFAOYSA-N 0.000 claims 1
- IJNQZHSSMJEYAY-UHFFFAOYSA-N n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propan-2-ylpiperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(C(C)C)C1 IJNQZHSSMJEYAY-UHFFFAOYSA-N 0.000 claims 1
- PVVQBVFMSWLISV-UHFFFAOYSA-N n-[3-cyano-2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide Chemical compound CN1CC(CCC)CC1C(=O)NC(C(C)CC#N)C1C(O)C(O)C(O)C(SC)O1 PVVQBVFMSWLISV-UHFFFAOYSA-N 0.000 claims 1
- KOGLZVRPQJRCHE-UHFFFAOYSA-N phenyl 2-[[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]carbamoyl]-4-propylpiperidine-1-carboxylate Chemical compound C1C(CCC)CCN(C(=O)OC=2C=CC=CC=2)C1C(=O)NC(C(C)C)C1OC(SC)C(O)C(O)C1O KOGLZVRPQJRCHE-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40377002P | 2002-08-15 | 2002-08-15 | |
| PCT/US2003/025820 WO2004016632A2 (en) | 2002-08-15 | 2003-08-15 | Lincomycin derivatives possessing antibacterial activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006504673A JP2006504673A (ja) | 2006-02-09 |
| JP2006504673A5 true JP2006504673A5 (enExample) | 2006-10-05 |
Family
ID=31888275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004529541A Pending JP2006504673A (ja) | 2002-08-15 | 2003-08-15 | 抗菌活性を有するリンコマイシン誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7164011B2 (enExample) |
| EP (1) | EP1529052A2 (enExample) |
| JP (1) | JP2006504673A (enExample) |
| KR (1) | KR20050056195A (enExample) |
| CN (1) | CN1315859C (enExample) |
| AU (1) | AU2003265475B2 (enExample) |
| BR (1) | BR0313725A (enExample) |
| CA (1) | CA2493799A1 (enExample) |
| EA (1) | EA200500353A1 (enExample) |
| IL (1) | IL166476A (enExample) |
| MX (1) | MXPA05001689A (enExample) |
| NO (1) | NO20051289L (enExample) |
| NZ (1) | NZ538141A (enExample) |
| WO (1) | WO2004016632A2 (enExample) |
| ZA (1) | ZA200501012B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7199105B2 (en) | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| WO2004016632A2 (en) | 2002-08-15 | 2004-02-26 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7256177B2 (en) | 2003-06-17 | 2007-08-14 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| CA2528596A1 (en) * | 2003-06-17 | 2005-01-27 | Vicuron Pharmaceuticals Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7199106B2 (en) | 2003-06-17 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antimicrobial activity |
| AU2004261550A1 (en) * | 2003-06-17 | 2005-02-10 | Vicuron Pharmaceuticals, Inc. | Novel lincomycin derivatives possessing antimicrobial activity |
| US7361743B2 (en) | 2004-02-11 | 2008-04-22 | Pfizer Inc | Lincomycin derivatives possessing antibacterial activity |
| JP5064237B2 (ja) * | 2005-12-09 | 2012-10-31 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | リンコマイシン誘導体およびこれを有効成分とする抗菌剤 |
| JP5356223B2 (ja) * | 2007-05-31 | 2013-12-04 | Ｍｅｉｊｉ Ｓｅｉｋａファルマ株式会社 | リンコマイシン誘導体及びこれを有効成分とする抗菌剤 |
| US7867980B2 (en) * | 2007-05-31 | 2011-01-11 | Meiji Seika Kaisha, Ltd. | Lincosamide derivatives and antimicrobial agents comprising the same as active ingredient |
| CN101555223B (zh) * | 2009-04-17 | 2011-06-01 | 北京化工大学 | 一种吡利霉素中间体及其制备方法 |
| US9533973B2 (en) | 2011-12-08 | 2017-01-03 | The Board Of Regents Of The University Of Texas System | Allosteric modulators of 5-hydroxytryptamine 2C receptor (5-HT2CR) |
| CN105566411B (zh) * | 2014-11-07 | 2020-11-13 | 中国科学院上海有机化学研究所 | 林可霉素生物合成中间产物及其制法和用途 |
Family Cites Families (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US29558A (en) * | 1860-08-14 | Bread-slicer | ||
| US2851463A (en) | 1956-04-09 | 1958-09-09 | Upjohn Co | Desalicetin and salts, and hydrocarbon carboxylic acid esters |
| US2928844A (en) | 1958-02-24 | 1960-03-15 | Upjohn Co | Celesticetin, its salts and method of preparation |
| US3086912A (en) | 1961-07-03 | 1963-04-23 | Upjohn Co | Antibiotic lincolnensin and method of production |
| US3268556A (en) | 1964-04-13 | 1966-08-23 | Upjohn Co | Novel lincomycin derivatives |
| US3255174A (en) | 1964-04-13 | 1966-06-07 | Upjohn Co | 7-0-methyl-n-acyl-3, 4-o-isopropylidene-1-deoxy-lincosamines |
| NL128232C (enExample) | 1964-04-13 | |||
| NL146501C (enExample) | 1964-07-01 | |||
| US3764672A (en) | 1964-08-05 | 1973-10-09 | Upjohn Co | Composition and process of treatment using lincomycin derivatives |
| US3380992A (en) | 1965-06-14 | 1968-04-30 | Upjohn Co | Lincomycin derivatives and process for preparing same |
| US3282917A (en) | 1964-08-17 | 1966-11-01 | Upjohn Co | Methyl n-(1-alkyl-4-alkoxy-prolyl)-alpha-thiolincosaminide compounds and process therefor |
| US3502648A (en) | 1965-02-08 | 1970-03-24 | Upjohn Co | 7-halo-7-deoxythiolincosaminides and process for preparing the same |
| NL140527B (nl) | 1965-02-08 | 1973-12-17 | Upjohn Co | Werkwijze ter bereiding van aan lincomycine verwante verbindingen. |
| US3496163A (en) | 1965-02-08 | 1970-02-17 | Upjohn Co | 7-halo-7-deoxylincomycins and process for preparing the same |
| US3435025A (en) | 1966-03-18 | 1969-03-25 | Upjohn Co | 7-deoxylincomycin and analogs and isomers thereof and process for making the same |
| US3475407A (en) | 1967-12-22 | 1969-10-28 | Upjohn Co | Process for preparing 7(r)- and 7(s)-halolincomycins |
| US3509127A (en) | 1968-04-30 | 1970-04-28 | Upjohn Co | Isologs of lincomycins and process for preparing the same |
| US3544551A (en) | 1968-04-30 | 1970-12-01 | Upjohn Co | 7-mercapto-7-deoxylincomycins and process for preparing the same |
| US3555007A (en) | 1968-07-22 | 1971-01-12 | Upjohn Co | 7-deoxy-7-halo lincomycin d derivatives |
| US3549615A (en) * | 1968-10-17 | 1970-12-22 | Upjohn Co | Lincomycin derivatives and process for producing the same |
| US3702322A (en) * | 1970-04-06 | 1972-11-07 | Upjohn Co | Derivatives of lincomycin and its analogs and process |
| DE2118636A1 (de) | 1970-04-20 | 1971-11-04 | The Upjohn Co., Kalamazoo, Mich. (V.StA.) | 3-Nucleotide von Lincomycin und deren Analogen, Verfahren zu ihrer Herstellung und ihre Verwendung in therapeutischen Präparaten |
| US3692767A (en) | 1970-05-06 | 1972-09-19 | Upjohn Co | Process for making lincomycin and analogs thereof and novel compounds obtained thereby |
| US3714141A (en) | 1970-05-26 | 1973-01-30 | Upjohn Co | Process for making 7-halolincomycins |
| US3674647A (en) | 1970-10-07 | 1972-07-04 | Upjohn Co | Preparation of lincomycin analogues |
| US3715346A (en) | 1970-11-18 | 1973-02-06 | Upjohn Co | Process for the preparation of lincomycin compounds |
| US3671647A (en) | 1971-03-24 | 1972-06-20 | Upjohn Co | Lincomycin 3-nucleotides and the salts thereof |
| US3892730A (en) | 1971-06-23 | 1975-07-01 | Upjohn Co | 1{40 -({62 -hydroxyethyl)-1{40 -demethyl clindamycin 2-acylates |
| US3892729A (en) | 1971-06-23 | 1975-07-01 | Upjohn Co | 1{40 (Beta-hydroxyethyl)-1{40 -demethyl clindamycin 2-phosphates |
| US3856943A (en) | 1971-06-23 | 1974-12-24 | Upjohn Co | Compositions and process |
| US3787390A (en) | 1971-06-23 | 1974-01-22 | Upjohn Co | Analogs of lincomycin and process |
| US3915954A (en) | 1971-11-15 | 1975-10-28 | Upjohn Co | Derivatives of lincomycin and its analogs and process |
| BE793630A (fr) | 1972-01-03 | 1973-07-03 | Upjohn Co | Nouvel antibiotique de la classe des celesticetines et son procede de preparation |
| US3853843A (en) | 1972-12-13 | 1974-12-10 | Upjohn Co | Derivatives of thiolincosaminide compounds |
| US3849396A (en) | 1973-01-08 | 1974-11-19 | Upjohn Co | Lincomycin and clindamycin 1-o-ethers |
| US3870699A (en) | 1973-03-06 | 1975-03-11 | Upjohn Co | Lincomycin analogs |
| US3833475A (en) | 1973-04-23 | 1974-09-03 | Upjohn Co | Process for preparing lincomycin |
| US4271266A (en) | 1974-06-10 | 1981-06-02 | The Upjohn Manufacturing Company | Process for preparing lincomycin |
| US4031304A (en) | 1976-01-30 | 1977-06-21 | The Upjohn Company | Process for preparing lincomycin derivatives |
| US4278789A (en) | 1979-11-23 | 1981-07-14 | The Upjohn Company | Lincomycin compounds |
| US4309533A (en) | 1980-05-19 | 1982-01-05 | The Upjohn Company | Lincomycin compounds |
| US4310660A (en) | 1980-05-19 | 1982-01-12 | The Upjohn Company | Lincomycin compounds |
| US4293547A (en) | 1980-08-25 | 1981-10-06 | The Upjohn Company | Method of treating malaria |
| US4317903A (en) | 1981-01-26 | 1982-03-02 | The Upjohn Company | Process for the purification of lincomycin |
| US4383109A (en) | 1981-04-20 | 1983-05-10 | The Upjohn Company | Lincomycin nucleotides |
| US4464466A (en) | 1981-04-20 | 1984-08-07 | The Upjohn Company | Process of producing lincomycin nucleotides |
| US4430495A (en) | 1982-09-17 | 1984-02-07 | The Upjohn Company | Process for preparing lincomycin and clindamycin ribonucleotides |
| US4568741A (en) | 1984-05-15 | 1986-02-04 | The Upjohn Company | Synthesis of 7-halo-7-deoxylincomycins |
| CN1004002B (zh) | 1984-11-29 | 1989-04-26 | 厄普约翰公司 | 制备7-卤-7-去氧林可霉素及其类似化合物的改进方法 |
| WO1989004672A1 (en) | 1987-11-20 | 1989-06-01 | The Upjohn Company | Derivatives of lincosaminide antibiotics |
| AU4543899A (en) | 1998-06-08 | 1999-12-30 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
| WO2004016632A2 (en) | 2002-08-15 | 2004-02-26 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7199105B2 (en) | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| AU2004261550A1 (en) | 2003-06-17 | 2005-02-10 | Vicuron Pharmaceuticals, Inc. | Novel lincomycin derivatives possessing antimicrobial activity |
| CA2528596A1 (en) | 2003-06-17 | 2005-01-27 | Vicuron Pharmaceuticals Inc. | Lincomycin derivatives possessing antibacterial activity |
-
2003
- 2003-08-15 WO PCT/US2003/025820 patent/WO2004016632A2/en not_active Ceased
- 2003-08-15 US US10/642,807 patent/US7164011B2/en not_active Expired - Fee Related
- 2003-08-15 EA EA200500353A patent/EA200500353A1/ru unknown
- 2003-08-15 CN CNB038212935A patent/CN1315859C/zh not_active Expired - Fee Related
- 2003-08-15 BR BRPI0313725-2A patent/BR0313725A/pt not_active IP Right Cessation
- 2003-08-15 CA CA002493799A patent/CA2493799A1/en not_active Abandoned
- 2003-08-15 NZ NZ538141A patent/NZ538141A/en unknown
- 2003-08-15 JP JP2004529541A patent/JP2006504673A/ja active Pending
- 2003-08-15 ZA ZA200501012A patent/ZA200501012B/en unknown
- 2003-08-15 KR KR1020057002309A patent/KR20050056195A/ko not_active Ceased
- 2003-08-15 EP EP03788609A patent/EP1529052A2/en not_active Withdrawn
- 2003-08-15 MX MXPA05001689A patent/MXPA05001689A/es active IP Right Grant
- 2003-08-15 AU AU2003265475A patent/AU2003265475B2/en not_active Ceased
-
2005
- 2005-01-25 IL IL166476A patent/IL166476A/en not_active IP Right Cessation
- 2005-03-14 NO NO20051289A patent/NO20051289L/no unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006504673A5 (enExample) | ||
| IL205420A (en) | Immunogoldular and Derivative Compounds, Pharmaceutical Compounds in the Treatment of Inflammatory Stomach and Gastrointestinal Disorders | |
| TNSN04246A1 (fr) | Derives d'heteroarylamides benzocondenses de thienopyridines utiles comme agents therapeutiques, compositions pharmaceutiques les contenant et methodes pour leur utilisation | |
| KR880005092A (ko) | 항궤양제로서 유효한 벤즈이미다졸의 신규 유도체 | |
| ATE283266T1 (de) | 1,5-benzothiazepine und ihre verwendungs als hypolipidämika | |
| JP2002502874A5 (enExample) | ||
| JP2818299B2 (ja) | ウイルス感染の治療におけるジデオキシヌクレオシドアナローグの使用 | |
| JP2019515884A5 (enExample) | ||
| JP2004506740A5 (enExample) | ||
| IL184116A0 (en) | Use of thiazolidinone derivatives as antiangiogenic agents | |
| JP2002537258A5 (enExample) | ||
| KR930004296A (ko) | 신규(2-알킬-3-피리딜)메틸피페라진 유도체 | |
| JP2004529928A5 (enExample) | ||
| JP2007501270A5 (enExample) | ||
| RU2003134629A (ru) | Соединения цефема | |
| JP2004521150A5 (enExample) | ||
| CA2441309A1 (en) | Biguanide derivatives | |
| JP2004518639A5 (enExample) | ||
| AU763111B2 (en) | Polycyclic 2-amino-thiazole systems, method for the production thereof and medicament containing said compounds | |
| JPH1036365A5 (enExample) | ||
| JP2007507472A5 (enExample) | ||
| ITMI20011744A1 (it) | Farmaci per le vasculopatie | |
| HUP0203790A2 (hu) | (6-Metoxi-2-naftil)-ecetsav prodrugokat tartalmazó gyógyszerkészítmények alkalmazása gyulladás kezelésére | |
| KR910002818A (ko) | 4,5,6,7-사치환된 벤즈옥사졸론 | |
| RU2001131557A (ru) | Аналоги витамина D и их фармацевтическое использование |