JP2009534414A5 - - Google Patents
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- Publication number
- JP2009534414A5 JP2009534414A5 JP2009506764A JP2009506764A JP2009534414A5 JP 2009534414 A5 JP2009534414 A5 JP 2009534414A5 JP 2009506764 A JP2009506764 A JP 2009506764A JP 2009506764 A JP2009506764 A JP 2009506764A JP 2009534414 A5 JP2009534414 A5 JP 2009534414A5
- Authority
- JP
- Japan
- Prior art keywords
- biphenyl
- ylmethyl
- pyrrolidin
- cyclohexyl
- dichloro
- 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.)
- Granted
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- 229910052736 halogen Inorganic materials 0.000 claims 33
- 150000002367 halogens Chemical class 0.000 claims 33
- 229910052739 hydrogen Inorganic materials 0.000 claims 23
- 239000001257 hydrogen Substances 0.000 claims 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- FTGQOITVPAREEZ-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 FTGQOITVPAREEZ-UHFFFAOYSA-N 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- -1 4-hydroxy-cyclohexyl Chemical group 0.000 claims 3
- FQZKEXXNYOFXKH-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-(4-methylpiperazine-1-carbonyl)phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 FQZKEXXNYOFXKH-UHFFFAOYSA-N 0.000 claims 2
- OBWQQCUPEXHOGD-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-[4-(2-fluoroethyl)piperazine-1-carbonyl]phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(CCF)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 OBWQQCUPEXHOGD-UHFFFAOYSA-N 0.000 claims 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- FFCJYOPAPGHIFA-UHFFFAOYSA-N 3-[[4-[4-(3,4,6,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazine-2-carbonyl)phenyl]-2,6-dichlorophenyl]methyl]-1-cyclohexylpyrrolidin-2-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CC3CCCN3CC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 FFCJYOPAPGHIFA-UHFFFAOYSA-N 0.000 claims 2
- LLQMVSUUORPKIN-VCUSLETLSA-N (2r)-2-[[4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]amino]-3-hydroxypropanoic acid Chemical compound C1=CC(C(=O)N[C@H](CO)C(O)=O)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 LLQMVSUUORPKIN-VCUSLETLSA-N 0.000 claims 1
- LLQMVSUUORPKIN-LUTIACGYSA-N (2s)-2-[[4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]amino]-3-hydroxypropanoic acid Chemical compound C1=CC(C(=O)N[C@@H](CO)C(O)=O)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 LLQMVSUUORPKIN-LUTIACGYSA-N 0.000 claims 1
- PUIPNGPLURLFDK-XEGCMXMBSA-N (3r)-1-cyclohex-3-en-1-yl-3-[[2,6-dichloro-4-[4-[4-(trifluoromethyl)piperidine-1-carbonyl]phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1CC(C(F)(F)F)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(C[C@H]3C(N(C4CC=CCC4)CC3)=O)=C(Cl)C=2)C=C1 PUIPNGPLURLFDK-XEGCMXMBSA-N 0.000 claims 1
- PBLGOGKBJMAIRP-FQEVSTJZSA-N (3r)-3-[[2,6-dichloro-4-[4-(morpholine-4-carbonyl)phenyl]phenyl]methyl]-1-(oxan-4-yl)pyrrolidin-2-one Chemical compound C([C@H](C1=O)CC2=C(Cl)C=C(C=C2Cl)C=2C=CC(=CC=2)C(=O)N2CCOCC2)CN1C1CCOCC1 PBLGOGKBJMAIRP-FQEVSTJZSA-N 0.000 claims 1
- FDSPPNDSKWFJRC-NRFANRHFSA-N (3r)-3-[[2,6-dichloro-4-[4-[4-(2,2,2-trifluoroethyl)piperazine-1-carbonyl]phenyl]phenyl]methyl]-1-(oxan-4-yl)pyrrolidin-2-one Chemical compound C1CN(CC(F)(F)F)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(C[C@H]3C(N(C4CCOCC4)CC3)=O)=C(Cl)C=2)C=C1 FDSPPNDSKWFJRC-NRFANRHFSA-N 0.000 claims 1
- RHSDTNUTYQHFCY-XOYNAWAESA-N (3r)-3-[[2,6-dichloro-4-[4-[4-(trifluoromethyl)piperidine-1-carbonyl]phenyl]phenyl]methyl]-1-(4-hydroxycyclohexyl)pyrrolidin-2-one Chemical compound C1CC(O)CCC1N1C(=O)[C@H](CC=2C(=CC(=CC=2Cl)C=2C=CC(=CC=2)C(=O)N2CCC(CC2)C(F)(F)F)Cl)CC1 RHSDTNUTYQHFCY-XOYNAWAESA-N 0.000 claims 1
- ASZWFMGYWQWAND-BUXCFDRUSA-N (3r)-3-[[4-[4-[4-(2-adamantyl)piperazine-1-carbonyl]phenyl]-2,6-dichlorophenyl]methyl]-1-(oxan-4-yl)pyrrolidin-2-one Chemical compound C([C@H](C1=O)CC2=C(Cl)C=C(C=C2Cl)C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C2C3CC4CC(C3)CC2C4)CN1C1CCOCC1 ASZWFMGYWQWAND-BUXCFDRUSA-N 0.000 claims 1
- MJJAMUJZDPFYQR-UHFFFAOYSA-N 1-[4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]piperidin-4-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CCC(=O)CC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 MJJAMUJZDPFYQR-UHFFFAOYSA-N 0.000 claims 1
- HFIKQAUQAUWWAP-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridine-5-carbonyl)phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CC=3N=CNC=3CC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 HFIKQAUQAUWWAP-UHFFFAOYSA-N 0.000 claims 1
- FGHASNMJBNWRFY-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-(morpholine-4-carbonyl)phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CCOCC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 FGHASNMJBNWRFY-UHFFFAOYSA-N 0.000 claims 1
- ZGJLBUQCWVWBHE-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-(piperazine-1-carbonyl)phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CCNCC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 ZGJLBUQCWVWBHE-UHFFFAOYSA-N 0.000 claims 1
- CRPMTNOYUAPVNC-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-(pyrrolidine-1-carbonyl)phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CCCC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 CRPMTNOYUAPVNC-UHFFFAOYSA-N 0.000 claims 1
- LJANFMRUJVYPKW-ZROWWJAZSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-[(1s,4s)-5-propan-2-yl-2,5-diazabicyclo[2.2.1]heptane-2-carbonyl]phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C([C@]1(N(C[C@]2([H])C1)C(C)C)[H])N2C(=O)C(C=C1)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 LJANFMRUJVYPKW-ZROWWJAZSA-N 0.000 claims 1
- XJZNJTHZTSGZCQ-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-[3-(trifluoromethyl)-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-7-carbonyl]phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN2C(C(F)(F)F)=NN=C2CN1C(=O)C(C=C1)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 XJZNJTHZTSGZCQ-UHFFFAOYSA-N 0.000 claims 1
- HGOPULSKNSIYGU-UHFFFAOYSA-N 1-cyclohexyl-3-[[2,6-dichloro-4-[4-[4-(2,2,2-trifluoroethyl)piperazine-1-carbonyl]phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(CC(F)(F)F)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 HGOPULSKNSIYGU-UHFFFAOYSA-N 0.000 claims 1
- OMTPKGONTMSFIU-UHFFFAOYSA-N 1-cyclohexyl-3-[[2-(trifluoromethyl)-4-[4-[4-(trifluoromethyl)piperidine-1-carbonyl]phenyl]phenyl]methyl]pyrrolidin-2-one Chemical compound C1CC(C(F)(F)F)CCN1C(=O)C1=CC=C(C=2C=C(C(CC3C(N(C4CCCCC4)CC3)=O)=CC=2)C(F)(F)F)C=C1 OMTPKGONTMSFIU-UHFFFAOYSA-N 0.000 claims 1
- SFNPEXIGBMOTHN-UHFFFAOYSA-N 1-cyclohexyl-3-[[4-[4-(4,4-difluoropiperidine-1-carbonyl)phenyl]-2-(trifluoromethoxy)phenyl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)OC1=CC(C=2C=CC(=CC=2)C(=O)N2CCC(F)(F)CC2)=CC=C1CC(C1=O)CCN1C1CCCCC1 SFNPEXIGBMOTHN-UHFFFAOYSA-N 0.000 claims 1
- RVZHEPWRPXLAGR-UHFFFAOYSA-N 1-cyclohexyl-3-[[4-[4-(4-methylpiperazine-1-carbonyl)phenyl]-2-(trifluoromethyl)phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(C)CCN1C(=O)C1=CC=C(C=2C=C(C(CC3C(N(C4CCCCC4)CC3)=O)=CC=2)C(F)(F)F)C=C1 RVZHEPWRPXLAGR-UHFFFAOYSA-N 0.000 claims 1
- PSKGCKURKYDZGN-UHFFFAOYSA-N 1-cyclohexyl-3-[[4-[4-(4-propan-2-ylpiperazine-1-carbonyl)phenyl]-2-(trifluoromethoxy)phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=C(C=2C=C(OC(F)(F)F)C(CC3C(N(C4CCCCC4)CC3)=O)=CC=2)C=C1 PSKGCKURKYDZGN-UHFFFAOYSA-N 0.000 claims 1
- ODLHJOUEWNEAOL-UHFFFAOYSA-N 1-cyclohexyl-3-[[4-[4-(morpholine-4-carbonyl)phenyl]-2-(trifluoromethoxy)phenyl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)OC1=CC(C=2C=CC(=CC=2)C(=O)N2CCOCC2)=CC=C1CC(C1=O)CCN1C1CCCCC1 ODLHJOUEWNEAOL-UHFFFAOYSA-N 0.000 claims 1
- PJPIAAKZBOKSCB-UHFFFAOYSA-N 1-cyclohexyl-3-[[4-[4-(piperazine-1-carbonyl)phenyl]-2-(trifluoromethyl)phenyl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C1=CC(C=2C=CC(=CC=2)C(=O)N2CCNCC2)=CC=C1CC(C1=O)CCN1C1CCCCC1 PJPIAAKZBOKSCB-UHFFFAOYSA-N 0.000 claims 1
- CDPKCVLZUGXCJB-UHFFFAOYSA-N 1-cyclohexyl-3-[[4-[4-[4-(2,2,2-trifluoroethyl)piperazine-1-carbonyl]phenyl]-2-(trifluoromethoxy)phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(CC(F)(F)F)CCN1C(=O)C1=CC=C(C=2C=C(OC(F)(F)F)C(CC3C(N(C4CCCCC4)CC3)=O)=CC=2)C=C1 CDPKCVLZUGXCJB-UHFFFAOYSA-N 0.000 claims 1
- UOMLDXJGFLWSGM-UHFFFAOYSA-N 1-cyclohexyl-3-[[4-[4-[4-(2-fluoroethyl)piperazine-1-carbonyl]phenyl]-2-(trifluoromethyl)phenyl]methyl]pyrrolidin-2-one Chemical compound C1CN(CCF)CCN1C(=O)C1=CC=C(C=2C=C(C(CC3C(N(C4CCCCC4)CC3)=O)=CC=2)C(F)(F)F)C=C1 UOMLDXJGFLWSGM-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- TXTOIAOHAACBSD-UHFFFAOYSA-N 2-[[4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]amino]-3-(dimethylamino)propanoic acid Chemical compound C1=CC(C(=O)NC(CN(C)C)C(O)=O)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 TXTOIAOHAACBSD-UHFFFAOYSA-N 0.000 claims 1
- LQZDOHOLYVRZNY-UHFFFAOYSA-N 2-[[4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]amino]acetic acid Chemical compound C1=CC(C(=O)NCC(=O)O)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 LQZDOHOLYVRZNY-UHFFFAOYSA-N 0.000 claims 1
- ZKMUVDFNWGJQSB-UHFFFAOYSA-N 2-[[4-[3-chloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]amino]acetic acid Chemical compound C1=CC(C(=O)NCC(=O)O)=CC=C1C(C=C1Cl)=CC=C1CC1C(=O)N(C2CCCCC2)CC1 ZKMUVDFNWGJQSB-UHFFFAOYSA-N 0.000 claims 1
- QGQFAOLKVXUALL-UHFFFAOYSA-N 3-[[4-[4-(3,4,6,7,9,9a-hexahydro-1h-pyrazino[2,1-c][1,4]oxazine-8-carbonyl)phenyl]-2,6-dichlorophenyl]methyl]-1-cyclohexylpyrrolidin-2-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CC3COCCN3CC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 QGQFAOLKVXUALL-UHFFFAOYSA-N 0.000 claims 1
- BKWBOXYYSJAZAI-UHFFFAOYSA-N 3-[[4-[4-(4-acetylpiperazine-1-carbonyl)phenyl]-2,6-dichlorophenyl]methyl]-1-cyclohexylpyrrolidin-2-one Chemical compound C1CN(C(=O)C)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 BKWBOXYYSJAZAI-UHFFFAOYSA-N 0.000 claims 1
- TZDXUWHQNZLUML-UHFFFAOYSA-N 3-[[4-[4-(4-tert-butylpiperazine-1-carbonyl)phenyl]-2,6-dichlorophenyl]methyl]-1-cyclohexylpyrrolidin-2-one Chemical compound C1CN(C(C)(C)C)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 TZDXUWHQNZLUML-UHFFFAOYSA-N 0.000 claims 1
- ATDYXYVCWQRKGU-UHFFFAOYSA-N 3-[[4-[4-(4-tert-butylpiperazine-1-carbonyl)phenyl]-2-(trifluoromethoxy)phenyl]methyl]-1-cyclohexylpyrrolidin-2-one Chemical compound C1CN(C(C)(C)C)CCN1C(=O)C1=CC=C(C=2C=C(OC(F)(F)F)C(CC3C(N(C4CCCCC4)CC3)=O)=CC=2)C=C1 ATDYXYVCWQRKGU-UHFFFAOYSA-N 0.000 claims 1
- LYDIBBTZDSYELV-UHFFFAOYSA-N 3-[[4-[4-(azetidine-1-carbonyl)phenyl]-2,6-dichlorophenyl]methyl]-1-cyclohexylpyrrolidin-2-one Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)N2CCC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 LYDIBBTZDSYELV-UHFFFAOYSA-N 0.000 claims 1
- HSBMZZXFGMQDKF-UHFFFAOYSA-N 3-[[4-[4-[4-(2-adamantyl)piperazine-1-carbonyl]phenyl]-2-(trifluoromethoxy)phenyl]methyl]-1-cyclohexylpyrrolidin-2-one Chemical compound FC(F)(F)OC1=CC(C=2C=CC(=CC=2)C(=O)N2CCN(CC2)C2C3CC4CC(C3)CC2C4)=CC=C1CC(C1=O)CCN1C1CCCCC1 HSBMZZXFGMQDKF-UHFFFAOYSA-N 0.000 claims 1
- LAMFWGSPDJDIQU-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-2-fluorobenzamide Chemical compound C1=C(F)C(C(=O)N)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 LAMFWGSPDJDIQU-UHFFFAOYSA-N 0.000 claims 1
- DGHWFRIIZVVYRZ-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 DGHWFRIIZVVYRZ-UHFFFAOYSA-N 0.000 claims 1
- JQONRDCZIMXIGK-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 JQONRDCZIMXIGK-UHFFFAOYSA-N 0.000 claims 1
- CEDYWXJIRUWDTR-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-n-methyl-n-(2h-tetrazol-5-yl)benzamide Chemical compound N=1N=NNC=1N(C)C(=O)C(C=C1)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 CEDYWXJIRUWDTR-UHFFFAOYSA-N 0.000 claims 1
- ZGVZABOWTRSRKZ-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 ZGVZABOWTRSRKZ-UHFFFAOYSA-N 0.000 claims 1
- QKDMPWYAUDNJQX-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-n-piperidin-4-ylbenzamide Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)NC2CCNCC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 QKDMPWYAUDNJQX-UHFFFAOYSA-N 0.000 claims 1
- FFNBZBGDGKXKTL-UHFFFAOYSA-N 4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-n-propan-2-ylbenzamide Chemical compound C1=CC(C(=O)NC(C)C)=CC=C1C(C=C1Cl)=CC(Cl)=C1CC1C(=O)N(C2CCCCC2)CC1 FFNBZBGDGKXKTL-UHFFFAOYSA-N 0.000 claims 1
- SKHARKFXKIPPKT-UHFFFAOYSA-N 4-[3-chloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]-n-piperidin-4-ylbenzamide Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)NC2CCNCC2)=CC=C1CC(C1=O)CCN1C1CCCCC1 SKHARKFXKIPPKT-UHFFFAOYSA-N 0.000 claims 1
- VOUJSQMZVLDAAG-UHFFFAOYSA-N 4-[4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1C(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 VOUJSQMZVLDAAG-UHFFFAOYSA-N 0.000 claims 1
- KKGHFWXENABPBU-UHFFFAOYSA-N 4-[[4-[3-chloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzoyl]amino]butanoic acid Chemical compound C1=CC(C(=O)NCCCC(=O)O)=CC=C1C(C=C1Cl)=CC=C1CC1C(=O)N(C2CCCCC2)CC1 KKGHFWXENABPBU-UHFFFAOYSA-N 0.000 claims 1
- URWADQYKVACKHR-XSTDGIKWSA-N C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(C=2C=C(Cl)C(C[C@H]3C(N([C@H]4CC[C@@H](O)CC4)CC3)=O)=C(Cl)C=2)C=C1 Chemical compound C1[C@@H](C)O[C@@H](C)CN1C(=O)C1=CC=C(C=2C=C(Cl)C(C[C@H]3C(N([C@H]4CC[C@@H](O)CC4)CC3)=O)=C(Cl)C=2)C=C1 URWADQYKVACKHR-XSTDGIKWSA-N 0.000 claims 1
- NABFRYNENPONIX-RNXOBYDBSA-N CC(C)(C)N1CCN(CC1)C(=O)c1ccc(cc1)-c1cc(Cl)c(C[C@@H]2CCN([C@H]3CC[C@H](O)CC3)C2=O)c(Cl)c1 Chemical compound CC(C)(C)N1CCN(CC1)C(=O)c1ccc(cc1)-c1cc(Cl)c(C[C@@H]2CCN([C@H]3CC[C@H](O)CC3)C2=O)c(Cl)c1 NABFRYNENPONIX-RNXOBYDBSA-N 0.000 claims 1
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- KQKAKIHSTSNMEU-JBACZVJFSA-N CNC(=O)CNC(=O)C1=CC=C(C=C1)C1=CC(=C(C(=C1)Cl)C[C@H]1C(N(CC1)[C@@H]1CC[C@H](CC1)O)=O)Cl Chemical compound CNC(=O)CNC(=O)C1=CC=C(C=C1)C1=CC(=C(C(=C1)Cl)C[C@H]1C(N(CC1)[C@@H]1CC[C@H](CC1)O)=O)Cl KQKAKIHSTSNMEU-JBACZVJFSA-N 0.000 claims 1
- KAOTUIQYINWAHI-OEMFJLHTSA-N COC1CCN(CC1)C(=O)c1ccc(cc1)-c1cc(Cl)c(C[C@@H]2CCN([C@@H]3CC[C@H](O)CC3)C2=O)c(Cl)c1 Chemical compound COC1CCN(CC1)C(=O)c1ccc(cc1)-c1cc(Cl)c(C[C@@H]2CCN([C@@H]3CC[C@H](O)CC3)C2=O)c(Cl)c1 KAOTUIQYINWAHI-OEMFJLHTSA-N 0.000 claims 1
- HGSQMKYLVNMDPU-TUSQITKMSA-N CO[C@H]1CC[C@@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCC(CC2)C(F)(F)F)C1=O Chemical compound CO[C@H]1CC[C@@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCC(CC2)C(F)(F)F)C1=O HGSQMKYLVNMDPU-TUSQITKMSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
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- RQVJAXSLRNJIDP-OEMFJLHTSA-N O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCN(CC(F)(F)F)CC2)C1=O Chemical compound O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCN(CC(F)(F)F)CC2)C1=O RQVJAXSLRNJIDP-OEMFJLHTSA-N 0.000 claims 1
- QFKAUVRLRVHIKK-ZKMPZPQNSA-N O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCN(CCF)CC2)C1=O Chemical compound O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCN(CCF)CC2)C1=O QFKAUVRLRVHIKK-ZKMPZPQNSA-N 0.000 claims 1
- YTSPBDQWRNRFSX-ACIOBRDBSA-N O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCNCC2)C1=O Chemical compound O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCNCC2)C1=O YTSPBDQWRNRFSX-ACIOBRDBSA-N 0.000 claims 1
- LXQRPRMBLPVFJI-ACIOBRDBSA-N O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCOCC2)C1=O Chemical compound O[C@H]1CC[C@H](CC1)N1CC[C@@H](Cc2c(Cl)cc(cc2Cl)-c2ccc(cc2)C(=O)N2CCOCC2)C1=O LXQRPRMBLPVFJI-ACIOBRDBSA-N 0.000 claims 1
- UBVFFJTXUGQPTN-IBGZPJMESA-N [4-[3,5-dichloro-4-[[(3R)-1-(oxan-4-yl)pyrrolidin-3-yl]methyl]phenyl]phenyl]-[4-(trifluoromethyl)piperidin-1-yl]methanone Chemical compound ClC=1C=C(C=C(C1C[C@H]1CN(CC1)C1CCOCC1)Cl)C1=CC=C(C=C1)C(=O)N1CCC(CC1)C(F)(F)F UBVFFJTXUGQPTN-IBGZPJMESA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 claims 1
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- HPQSZZUSWFNQNL-UHFFFAOYSA-N n-(3-aminocyclohexyl)-4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzamide Chemical compound C1C(N)CCCC1NC(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 HPQSZZUSWFNQNL-UHFFFAOYSA-N 0.000 claims 1
- ZKTDNWLOSPWHBC-UHFFFAOYSA-N n-(4-aminocyclohexyl)-4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzamide Chemical compound C1CC(N)CCC1NC(=O)C1=CC=C(C=2C=C(Cl)C(CC3C(N(C4CCCCC4)CC3)=O)=C(Cl)C=2)C=C1 ZKTDNWLOSPWHBC-UHFFFAOYSA-N 0.000 claims 1
- LIUPKZLVZYZPKZ-UHFFFAOYSA-N n-(azetidin-3-yl)-4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzamide Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)NC2CNC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 LIUPKZLVZYZPKZ-UHFFFAOYSA-N 0.000 claims 1
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 claims 1
- BDBBAGUVWXXDLR-UHFFFAOYSA-N n-cyclopropyl-4-[3,5-dichloro-4-[(1-cyclohexyl-2-oxopyrrolidin-3-yl)methyl]phenyl]benzamide Chemical compound ClC1=CC(C=2C=CC(=CC=2)C(=O)NC2CC2)=CC(Cl)=C1CC(C1=O)CCN1C1CCCCC1 BDBBAGUVWXXDLR-UHFFFAOYSA-N 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
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- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 claims 1
- LPSJKZWOLKMCCA-UHFFFAOYSA-N tert-butyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OC(C)(C)C LPSJKZWOLKMCCA-UHFFFAOYSA-N 0.000 claims 1
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| MX2008013484A (es) * | 2006-04-21 | 2008-10-30 | Lilly Co Eli | Derivados de lactamas de ciclohexilpirazol como inhibidores de 11-beta-hidroxiesteroide deshidrogenasa 1. |
| JP5236628B2 (ja) | 2006-04-21 | 2013-07-17 | イーライ リリー アンド カンパニー | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１阻害剤としての、シクロヘキシルイミダゾールラクタム誘導体 |
| AU2007244971B2 (en) | 2006-04-24 | 2012-01-19 | Eli Lilly And Company | Cyclohexyl substituted pyrrolidinones as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| JP5189078B2 (ja) | 2006-04-24 | 2013-04-24 | イーライ リリー アンド カンパニー | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１の阻害剤 |
| MY148079A (en) | 2006-04-24 | 2013-02-28 | Lilly Co Eli | Inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| US7968585B2 (en) | 2006-04-25 | 2011-06-28 | Eli Lilly And Company | Inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| ES2336849T3 (es) | 2006-04-25 | 2010-04-16 | Eli Lilly And Company | Inhibidores de 11-beta-hidroxiesteroide dehidrogenasa 1. |
| MX2008013656A (es) * | 2006-04-25 | 2008-11-10 | Lilly Co Eli | Inhibidores de 11-beta-hidroxiesteroide deshidrogenasa. |
| CN101448816B (zh) * | 2006-04-28 | 2013-08-07 | 伊莱利利公司 | 作为11-β-羟类固醇脱氢酶1的抑制剂的哌啶基取代的吡咯烷酮类 |
| CN101460470B (zh) | 2006-05-30 | 2011-05-18 | 阿斯利康(瑞典)有限公司 | 作为dgat1抑制剂的1,3,4-二唑衍生物 |
| EP2125750B1 (en) | 2007-02-26 | 2014-05-21 | Vitae Pharmaceuticals, Inc. | Cyclic urea and carbamate inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2009017671A1 (en) | 2007-07-26 | 2009-02-05 | Vitae Pharmaceuticals, Inc. | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AR069207A1 (es) | 2007-11-07 | 2010-01-06 | Vitae Pharmaceuticals Inc | Ureas ciclicas como inhibidores de la 11 beta - hidroxi-esteroide deshidrogenasa 1 |
| EP2220048B1 (en) | 2007-11-16 | 2017-01-25 | Boehringer Ingelheim International GmbH | Aryl- and heteroarylcarbonyl derivatives of benzomorphanes and related scaffolds, medicaments containing such compounds and their use |
| US8440658B2 (en) | 2007-12-11 | 2013-05-14 | Vitae Pharmaceuticals, Inc. | Cyclic urea inhibitors of 11β-hydroxysteroid dehydrogenase 1 |
| JP5662803B2 (ja) | 2007-12-20 | 2015-02-04 | アストラゼネカ アクチボラグ | Ｄｇａｔ１阻害剤としてのカルバモイル化合物１９０ |
| JP5301563B2 (ja) | 2008-05-01 | 2013-09-25 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状インヒビター |
| EP2288596B1 (en) | 2008-05-13 | 2016-11-30 | Boehringer Ingelheim International GmbH | Alicyclic carboxylic acid derivatives of benzomorphans and related scaffolds, medicaments containing such compounds and their use |
| PL2324018T3 (pl) | 2008-07-25 | 2014-02-28 | Boehringer Ingelheim Int | Cykliczne inhibitory dehydrogenazy 11 beta-hydroksysteroidowej typu 1 |
| WO2010010150A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Synthesis of inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 |
| CA2729998A1 (en) | 2008-07-25 | 2010-01-28 | Boehringer Ingelheim International Gmbh | Inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| JP5679997B2 (ja) * | 2009-02-04 | 2015-03-04 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | １１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状阻害剤 |
| EP2243479A3 (en) | 2009-04-20 | 2011-01-19 | Abbott Laboratories | Novel amide and amidine derivates and uses thereof |
| MA33216B1 (fr) | 2009-04-30 | 2012-04-02 | Boehringer Ingelheim Int | Inhibiteurs cycliques de la 11béta-hydroxysteroïde déshydrogénase 1 |
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| EP2448928B1 (en) | 2009-07-01 | 2014-08-13 | Vitae Pharmaceuticals, Inc. | Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1 |
| WO2011056737A1 (en) | 2009-11-05 | 2011-05-12 | Boehringer Ingelheim International Gmbh | Novel chiral phosphorus ligands |
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| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| JP2013531636A (ja) | 2010-05-26 | 2013-08-08 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ２−オキソ−１，２−ジヒドロピリジン−４−イルボロン酸誘導体 |
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| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2744783A1 (en) | 2011-08-17 | 2014-06-25 | Boehringer Ingelheim International GmbH | Indenopyridine derivatives |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CN110498774A (zh) * | 2018-05-18 | 2019-11-26 | 上海医药工业研究院 | 一种艾沙康唑中间体的制备方法 |
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| WO2004056744A1 (en) | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| WO2005108361A1 (en) | 2004-05-07 | 2005-11-17 | Janssen Pharmaceutica N.V. | Adamantyl pyrrolidin-2-one derivatives as 11-beta hydroxysteroid dehydrogenase inhibitors |
| MXPA06012932A (es) | 2004-05-07 | 2007-01-26 | Janssen Pharmaceutica Nv | Derivados de pirrolidin-2-ona y piperidin-2-ona como inhibidores de 11-beta hidroxiesteroide deshidrogenasa. |
| JP2008515956A (ja) | 2004-10-12 | 2008-05-15 | ノボ ノルディスク アクティーゼルスカブ | １１β−ヒドロキシステロイドデヒドロゲナーゼ１型活性スピロ化合物 |
| EP1807072B1 (en) | 2004-10-29 | 2009-01-07 | Eli Lilly And Company | Cycloalkyl lactam derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| CN102731499B (zh) | 2004-11-10 | 2016-01-13 | 因塞特控股公司 | 内酰胺化合物及其作为药物的应用 |
| DK1830841T3 (da) | 2004-12-20 | 2008-10-13 | Lilly Co Eli | Cycloalkyllactamderivater som inhibitorer af 11-beta-hydroxysteroid-dehydrogenase 1 |
| EP1830840B1 (en) | 2004-12-21 | 2008-07-16 | Eli Lilly And Company | Cycloalkyl lactam derivatives as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| US20090264650A1 (en) | 2005-03-31 | 2009-10-22 | Nobuo Cho | Prophylactic/Therapeutic Agent for Diabetes |
| US7998959B2 (en) | 2006-01-12 | 2011-08-16 | Incyte Corporation | Modulators of 11-β hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| JP5236628B2 (ja) | 2006-04-21 | 2013-07-17 | イーライ リリー アンド カンパニー | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１阻害剤としての、シクロヘキシルイミダゾールラクタム誘導体 |
| MX2008013484A (es) | 2006-04-21 | 2008-10-30 | Lilly Co Eli | Derivados de lactamas de ciclohexilpirazol como inhibidores de 11-beta-hidroxiesteroide deshidrogenasa 1. |
| AU2007244971B2 (en) | 2006-04-24 | 2012-01-19 | Eli Lilly And Company | Cyclohexyl substituted pyrrolidinones as inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| JP5189078B2 (ja) | 2006-04-24 | 2013-04-24 | イーライ リリー アンド カンパニー | １１−β−ヒドロキシステロイドデヒドロゲナーゼ１の阻害剤 |
| MY148079A (en) | 2006-04-24 | 2013-02-28 | Lilly Co Eli | Inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| ES2336849T3 (es) | 2006-04-25 | 2010-04-16 | Eli Lilly And Company | Inhibidores de 11-beta-hidroxiesteroide dehidrogenasa 1. |
| MX2008013656A (es) | 2006-04-25 | 2008-11-10 | Lilly Co Eli | Inhibidores de 11-beta-hidroxiesteroide deshidrogenasa. |
| US7968585B2 (en) | 2006-04-25 | 2011-06-28 | Eli Lilly And Company | Inhibitors of 11-beta-hydroxysteroid dehydrogenase 1 |
| CN101448816B (zh) | 2006-04-28 | 2013-08-07 | 伊莱利利公司 | 作为11-β-羟类固醇脱氢酶1的抑制剂的哌啶基取代的吡咯烷酮类 |
| CL2008001839A1 (es) | 2007-06-21 | 2009-01-16 | Incyte Holdings Corp | Compuestos derivados de 2,7-diazaespirociclos, inhibidores de 11-beta hidroxil esteroide deshidrogenasa tipo 1; composicion farmaceutica que comprende a dichos compuestos; utiles para tratar la obesidad, diabetes, intolerancia a la glucosa, diabetes tipo ii, entre otras enfermedades. |
-
2007
- 2007-04-19 WO PCT/US2007/066921 patent/WO2007124337A1/en not_active Ceased
- 2007-04-19 AU AU2007240458A patent/AU2007240458B2/en not_active Ceased
- 2007-04-19 BR BRPI0710246-1A patent/BRPI0710246A2/pt not_active IP Right Cessation
- 2007-04-19 CN CN2007800143164A patent/CN101541747B/zh not_active Expired - Fee Related
- 2007-04-19 EP EP07760877.6A patent/EP2016047B1/en not_active Not-in-force
- 2007-04-19 MX MX2008013485A patent/MX2008013485A/es active IP Right Grant
- 2007-04-19 EA EA200870462A patent/EA014718B1/ru not_active IP Right Cessation
- 2007-04-19 US US12/297,349 patent/US8088776B2/en not_active Expired - Fee Related
- 2007-04-19 ES ES07760877T patent/ES2435115T3/es active Active
- 2007-04-19 JP JP2009506764A patent/JP5265521B2/ja not_active Expired - Fee Related
- 2007-04-19 CA CA2649741A patent/CA2649741C/en not_active Expired - Fee Related
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