CA2471620A1 - Pyrrolidone carboxamides - Google Patents
Pyrrolidone carboxamides Download PDFInfo
- Publication number
- CA2471620A1 CA2471620A1 CA002471620A CA2471620A CA2471620A1 CA 2471620 A1 CA2471620 A1 CA 2471620A1 CA 002471620 A CA002471620 A CA 002471620A CA 2471620 A CA2471620 A CA 2471620A CA 2471620 A1 CA2471620 A1 CA 2471620A1
- Authority
- CA
- Canada
- Prior art keywords
- rac
- phenyl
- carboxamide
- oxopyrrolidine
- ethyl
- 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.)
- Abandoned
Links
- XYVMBSCIEDOIJQ-UHFFFAOYSA-N Squamolone Chemical class NC(=O)N1CCCC1=O XYVMBSCIEDOIJQ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 208000008589 Obesity Diseases 0.000 claims abstract description 7
- 235000020824 obesity Nutrition 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 206010003246 arthritis Diseases 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 150000007514 bases Chemical class 0.000 claims abstract description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 3
- 150000004677 hydrates Chemical class 0.000 claims abstract description 3
- 239000012453 solvate Substances 0.000 claims abstract description 3
- -1 2,5-dimethylphenyl Chemical group 0.000 claims description 184
- 150000001412 amines Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- GBDDQLTTZULAOS-UHFFFAOYSA-N ethyl 2-(n-(4-aminophenyl)anilino)acetate Chemical compound C=1C=C(N)C=CC=1N(CC(=O)OCC)C1=CC=CC=C1 GBDDQLTTZULAOS-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- LHZRPAXAZZEHPC-UHFFFAOYSA-N 1-(5-methoxy-2-methylphenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound COC1=CC=C(C)C(N2C(CC(C2)C(O)=O)=O)=C1 LHZRPAXAZZEHPC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- RDZZYCFISJESTF-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1C1CC2=CC=CC=C2C1 RDZZYCFISJESTF-UHFFFAOYSA-N 0.000 claims description 4
- MQFHIILUDRLADC-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-5-oxo-n-[4-(n-propan-2-ylanilino)phenyl]pyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=C(C)C=2)C)C=CC=1N(C(C)C)C1=CC=CC=C1 MQFHIILUDRLADC-UHFFFAOYSA-N 0.000 claims description 4
- ORDWVWCHFJXNJU-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-(n-ethylanilino)phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=C(C)C=2)C)C=CC=1N(CC)C1=CC=CC=C1 ORDWVWCHFJXNJU-UHFFFAOYSA-N 0.000 claims description 4
- PWWLVURNNBTQNS-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-(n-methylanilino)phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=C(C)C=2)C)C=CC=1N(C)C1=CC=CC=C1 PWWLVURNNBTQNS-UHFFFAOYSA-N 0.000 claims description 4
- UANQFAFGDWVBIP-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-[(2-methoxybenzoyl)amino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound COC1=CC=CC=C1C(=O)NC(C=C1)=CC=C1NC(=O)C1CC(=O)N(C=2C(=CC=C(C)C=2)C)C1 UANQFAFGDWVBIP-UHFFFAOYSA-N 0.000 claims description 4
- UJJQERLXSMNGDD-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC=C(C)C(N2C(CC(C2)C(=O)NC=2C=CC(NCC=3N=C(C)C=C(C)N=3)=CC=2)=O)=C1 UJJQERLXSMNGDD-UHFFFAOYSA-N 0.000 claims description 4
- QQJCAJBDOPNICF-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-[ethyl(2-hydroxyethyl)amino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(N(CCO)CC)=CC=C1NC(=O)C1CC(=O)N(C=2C(=CC=C(C)C=2)C)C1 QQJCAJBDOPNICF-UHFFFAOYSA-N 0.000 claims description 4
- NBUHNVZCLZZWCM-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-[ethyl(propan-2-yl)amino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(N(C(C)C)CC)=CC=C1NC(=O)C1CC(=O)N(C=2C(=CC=C(C)C=2)C)C1 NBUHNVZCLZZWCM-UHFFFAOYSA-N 0.000 claims description 4
- MIRPNVFOUKDBEF-UHFFFAOYSA-N 1-(3-fluorophenyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1C1=CC=CC(F)=C1 MIRPNVFOUKDBEF-UHFFFAOYSA-N 0.000 claims description 4
- JCFURRFIHPXTAX-UHFFFAOYSA-N 1-[(2,4-dimethoxyphenyl)methyl]-n-(9-ethylcarbazol-3-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CC1=CC=C(OC)C=C1OC JCFURRFIHPXTAX-UHFFFAOYSA-N 0.000 claims description 4
- PKCVGJGLFSIAFY-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-n-(9-ethylcarbazol-3-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CC1=CC=CC=C1Cl PKCVGJGLFSIAFY-UHFFFAOYSA-N 0.000 claims description 4
- DMWSIFMEUPPWNG-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-n-(9-ethylcarbazol-3-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CC1=CC=C(Cl)C=C1 DMWSIFMEUPPWNG-UHFFFAOYSA-N 0.000 claims description 4
- SXPHAFCDHTZKGJ-UHFFFAOYSA-N 1-[2-(1-methylpyrrolidin-2-yl)ethyl]-5-oxopyrrolidine-3-carboxylic acid Chemical compound CN1CCCC1CCN1C(=O)CC(C(O)=O)C1 SXPHAFCDHTZKGJ-UHFFFAOYSA-N 0.000 claims description 4
- UDEPGEORTVFKKY-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-n-[4-[(4,6-dimethylpyrimidin-2-yl)amino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(NC=3N=C(C)C=C(C)N=3)=CC=2)C1 UDEPGEORTVFKKY-UHFFFAOYSA-N 0.000 claims description 4
- DSIJZEFRTBQDCQ-UHFFFAOYSA-N 1-cycloheptyl-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1C1CCCCCC1 DSIJZEFRTBQDCQ-UHFFFAOYSA-N 0.000 claims description 4
- IZALGPXWNQXDRV-UHFFFAOYSA-N 1-cycloheptyl-n-(9-ethylcarbazol-3-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1C1CCCCCC1 IZALGPXWNQXDRV-UHFFFAOYSA-N 0.000 claims description 4
- FVBSOAINVQLYHJ-UHFFFAOYSA-N 1-naphthalen-2-yl-5-oxopyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1C1=CC=C(C=CC=C2)C2=C1 FVBSOAINVQLYHJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- MUQFAIZQOQXVMX-UHFFFAOYSA-N 5-oxo-1-(2-pyridin-2-ylethyl)pyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1CCC1=CC=CC=N1 MUQFAIZQOQXVMX-UHFFFAOYSA-N 0.000 claims description 4
- FMPRHAJDAAZPAS-UHFFFAOYSA-N 5-oxo-1-(2-pyrrolidin-1-ylethyl)pyrrolidine-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)CN1CCN1CCCC1 FMPRHAJDAAZPAS-UHFFFAOYSA-N 0.000 claims description 4
- GAZTXROKNIHSRY-UHFFFAOYSA-N 5-oxo-n-[4-(n-propan-2-ylanilino)phenyl]-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=CC=2)C(C)C)C=CC=1N(C(C)C)C1=CC=CC=C1 GAZTXROKNIHSRY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 235000005686 eating Nutrition 0.000 claims description 4
- LXNZXQYFYFEBPK-UHFFFAOYSA-N ethyl 2-(n-(4-nitrophenyl)anilino)acetate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(CC(=O)OCC)C1=CC=CC=C1 LXNZXQYFYFEBPK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- FHRUHJMHXYMPMS-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-1-(3-fluorophenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1C1=CC=CC(F)=C1 FHRUHJMHXYMPMS-UHFFFAOYSA-N 0.000 claims description 4
- NJXOAHXVTCAHNP-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-1-(3-methoxyphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1C1=CC=CC(OC)=C1 NJXOAHXVTCAHNP-UHFFFAOYSA-N 0.000 claims description 4
- ZCNQQHNHLQDKSH-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-1-(furan-2-ylmethyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CC1=CC=CO1 ZCNQQHNHLQDKSH-UHFFFAOYSA-N 0.000 claims description 4
- ZUOGOMATEORWQP-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1C1=CC=CC=C1C(C)C ZUOGOMATEORWQP-UHFFFAOYSA-N 0.000 claims description 4
- ULRRIHNUZQIBKD-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-5-oxo-1-(2-pyridin-2-ylethyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CCC1=CC=CC=N1 ULRRIHNUZQIBKD-UHFFFAOYSA-N 0.000 claims description 4
- YIPMICHTLUYPTJ-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-5-oxo-1-(2-thiophen-2-ylethyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CCC1=CC=CS1 YIPMICHTLUYPTJ-UHFFFAOYSA-N 0.000 claims description 4
- ZHHQKDANPFTHME-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-5-oxo-1-(4-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1C1=CC=C(C(C)C)C=C1 ZHHQKDANPFTHME-UHFFFAOYSA-N 0.000 claims description 4
- ZZVBAJXEDCJVTK-UHFFFAOYSA-N n-(9-ethylcarbazol-3-yl)-5-oxo-1-(thiophen-2-ylmethyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(CC1=O)CN1CC1=CC=CS1 ZZVBAJXEDCJVTK-UHFFFAOYSA-N 0.000 claims description 4
- DDXGRHRXHSMDBJ-UHFFFAOYSA-N n-[4-(diethylamino)phenyl]-1-(2,5-dimethylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(N(CC)CC)=CC=C1NC(=O)C1CC(=O)N(C=2C(=CC=C(C)C=2)C)C1 DDXGRHRXHSMDBJ-UHFFFAOYSA-N 0.000 claims description 4
- LYZIXKAENGEEIA-UHFFFAOYSA-N n-[4-(n-ethylanilino)phenyl]-1-(5-methoxy-2-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=C(OC)C=2)C)C=CC=1N(CC)C1=CC=CC=C1 LYZIXKAENGEEIA-UHFFFAOYSA-N 0.000 claims description 4
- RPFYSLPELZPRSE-UHFFFAOYSA-N n-[4-(n-ethylanilino)phenyl]-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=CC=2)C(C)C)C=CC=1N(CC)C1=CC=CC=C1 RPFYSLPELZPRSE-UHFFFAOYSA-N 0.000 claims description 4
- QWRHEVZABGJAHU-UHFFFAOYSA-N n-[4-(n-methylanilino)phenyl]-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(=CC=2)N(C)C=2C=CC=CC=2)C1 QWRHEVZABGJAHU-UHFFFAOYSA-N 0.000 claims description 4
- YPDHOZOLYFHZDE-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)-ethylamino]phenyl]-1-(2-hydroxy-2-phenylethyl)-5-oxopyrrolidine-3-carboxamide Chemical compound N=1C(C)=CC(C)=NC=1N(CC)C(C=C1)=CC=C1NC(=O)C(CC1=O)CN1CC(O)C1=CC=CC=C1 YPDHOZOLYFHZDE-UHFFFAOYSA-N 0.000 claims description 4
- JWIROYJXCYLDQM-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)-ethylamino]phenyl]-1-(3-methoxyphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound N=1C(C)=CC(C)=NC=1N(CC)C(C=C1)=CC=C1NC(=O)C(CC1=O)CN1C1=CC=CC(OC)=C1 JWIROYJXCYLDQM-UHFFFAOYSA-N 0.000 claims description 4
- PMKYIMLKAUVVCR-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)-ethylamino]phenyl]-1-(5-methoxy-2-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound N=1C(C)=CC(C)=NC=1N(CC)C(C=C1)=CC=C1NC(=O)C(CC1=O)CN1C1=CC(OC)=CC=C1C PMKYIMLKAUVVCR-UHFFFAOYSA-N 0.000 claims description 4
- LHTWNVVZFJDULH-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)-ethylamino]phenyl]-5-oxo-1-(2-pyridin-2-ylethyl)pyrrolidine-3-carboxamide Chemical compound N=1C(C)=CC(C)=NC=1N(CC)C(C=C1)=CC=C1NC(=O)C(CC1=O)CN1CCC1=CC=CC=N1 LHTWNVVZFJDULH-UHFFFAOYSA-N 0.000 claims description 4
- LSYBYCKYJFXFQI-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)amino]phenyl]-1-(4-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(NC=3N=C(C)C=C(C)N=3)=CC=2)C1 LSYBYCKYJFXFQI-UHFFFAOYSA-N 0.000 claims description 4
- XFXQDMKEDIQDRP-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-1-(3-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC=CC(N2C(CC(C2)C(=O)NC=2C=CC(NCC=3N=C(C)C=C(C)N=3)=CC=2)=O)=C1 XFXQDMKEDIQDRP-UHFFFAOYSA-N 0.000 claims description 4
- BMXAXERIPUJLQO-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-1-(4-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(NCC=3N=C(C)C=C(C)N=3)=CC=2)C1 BMXAXERIPUJLQO-UHFFFAOYSA-N 0.000 claims description 4
- ACZBKBSDMQQODL-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(NCC=3N=C(C)C=C(C)N=3)=CC=2)C1 ACZBKBSDMQQODL-UHFFFAOYSA-N 0.000 claims description 4
- SYBVSKOIZFQNGP-UHFFFAOYSA-N n-[4-[2-(4,6-dimethylpyrimidin-2-yl)ethylamino]phenyl]-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound CC(C)C1=CC=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(NCCC=3N=C(C)C=C(C)N=3)=CC=2)C1 SYBVSKOIZFQNGP-UHFFFAOYSA-N 0.000 claims description 4
- NYOXBYUDBJDCNV-UHFFFAOYSA-N n-[4-[n-(2-methylpropyl)anilino]phenyl]-5-oxo-1-(2-propan-2-ylphenyl)pyrrolidine-3-carboxamide Chemical compound C=1C=C(NC(=O)C2CC(=O)N(C2)C=2C(=CC=CC=2)C(C)C)C=CC=1N(CC(C)C)C1=CC=CC=C1 NYOXBYUDBJDCNV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- LNBJEVSBTXABJJ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-n-(9-ethylcarbazol-3-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C1C2=CC=CC=C2CC1N(C(=O)C1)CC1C(=O)NC1=CC=C2N(CC)C3=CC=CC=C3C2=C1 LNBJEVSBTXABJJ-UHFFFAOYSA-N 0.000 claims description 3
- FQXMRJVAPNUZGC-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-n-[4-[(4,6-dimethylpyrimidin-2-yl)amino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(NC=2C=CC(NC(=O)C3CC(=O)N(C4CC5=CC=CC=C5C4)C3)=CC=2)=N1 FQXMRJVAPNUZGC-UHFFFAOYSA-N 0.000 claims description 3
- SZERAESXDZPLHH-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-(2,2-dimethylpropanoylamino)phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC=C(C)C(N2C(CC(C2)C(=O)NC=2C=CC(NC(=O)C(C)(C)C)=CC=2)=O)=C1 SZERAESXDZPLHH-UHFFFAOYSA-N 0.000 claims description 3
- HCUPWRGIGQHPSJ-UHFFFAOYSA-N 1-(2,5-dimethylphenyl)-n-[4-[(4,6-dimethylpyrimidin-2-yl)amino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC=C(C)C(N2C(CC(C2)C(=O)NC=2C=CC(NC=3N=C(C)C=C(C)N=3)=CC=2)=O)=C1 HCUPWRGIGQHPSJ-UHFFFAOYSA-N 0.000 claims description 3
- QDJSFUBPNPTMMG-UHFFFAOYSA-N 1-(2-hydroxy-2-phenylethyl)-5-oxopyrrolidine-3-carboxylic acid Chemical compound C=1C=CC=CC=1C(O)CN1CC(C(O)=O)CC1=O QDJSFUBPNPTMMG-UHFFFAOYSA-N 0.000 claims description 3
- YVDVOIKKHTZQJJ-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(NCC=3N=C(C)C=C(C)N=3)=CC=2)C1 YVDVOIKKHTZQJJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
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- FLIXNRDLSKVWIC-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)amino]phenyl]-5-oxo-1-phenylpyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(NC=2C=CC(NC(=O)C3CC(=O)N(C3)C=3C=CC=CC=3)=CC=2)=N1 FLIXNRDLSKVWIC-UHFFFAOYSA-N 0.000 description 1
- FELCAFLYFMGFQK-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-1-(2-hydroxy-2-phenylethyl)-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(CNC=2C=CC(NC(=O)C3CC(=O)N(CC(O)C=4C=CC=CC=4)C3)=CC=2)=N1 FELCAFLYFMGFQK-UHFFFAOYSA-N 0.000 description 1
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- LVBRDGQTZFJVJR-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-5-oxo-1-(2-pyridin-2-ylethyl)pyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(CNC=2C=CC(NC(=O)C3CC(=O)N(CCC=4N=CC=CC=4)C3)=CC=2)=N1 LVBRDGQTZFJVJR-UHFFFAOYSA-N 0.000 description 1
- LOMBSTXGTRPZMC-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-5-oxo-1-(2-thiophen-2-ylethyl)pyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(CNC=2C=CC(NC(=O)C3CC(=O)N(CCC=4SC=CC=4)C3)=CC=2)=N1 LOMBSTXGTRPZMC-UHFFFAOYSA-N 0.000 description 1
- PEMBPXQBLWJXDD-UHFFFAOYSA-N n-[4-[(4,6-dimethylpyrimidin-2-yl)methylamino]phenyl]-5-oxo-1-phenylpyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(CNC=2C=CC(NC(=O)C3CC(=O)N(C3)C=3C=CC=CC=3)=CC=2)=N1 PEMBPXQBLWJXDD-UHFFFAOYSA-N 0.000 description 1
- ODOGHORAERTEAC-UHFFFAOYSA-N n-[4-[2-(4,6-dimethylpyrimidin-2-yl)ethylamino]phenyl]-1-(3-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC=CC(N2C(CC(C2)C(=O)NC=2C=CC(NCCC=3N=C(C)C=C(C)N=3)=CC=2)=O)=C1 ODOGHORAERTEAC-UHFFFAOYSA-N 0.000 description 1
- SBIVPYPZDNFOCT-UHFFFAOYSA-N n-[4-[2-(4,6-dimethylpyrimidin-2-yl)ethylamino]phenyl]-1-(4-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound C1=CC(C)=CC=C1N1C(=O)CC(C(=O)NC=2C=CC(NCCC=3N=C(C)C=C(C)N=3)=CC=2)C1 SBIVPYPZDNFOCT-UHFFFAOYSA-N 0.000 description 1
- VVFLFUMNIRKWPP-UHFFFAOYSA-N n-[4-[2-(4,6-dimethylpyrimidin-2-yl)ethylamino]phenyl]-1-(naphthalen-1-ylmethyl)-5-oxopyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(CCNC=2C=CC(NC(=O)C3CC(=O)N(CC=4C5=CC=CC=C5C=CC=4)C3)=CC=2)=N1 VVFLFUMNIRKWPP-UHFFFAOYSA-N 0.000 description 1
- XMKRWFGPLZUFJB-UHFFFAOYSA-N n-[4-[2-(4,6-dimethylpyrimidin-2-yl)ethylamino]phenyl]-5-oxo-1-(2-pyrrolidin-1-ylethyl)pyrrolidine-3-carboxamide Chemical compound CC1=CC(C)=NC(CCNC=2C=CC(NC(=O)C3CC(=O)N(CCN4CCCC4)C3)=CC=2)=N1 XMKRWFGPLZUFJB-UHFFFAOYSA-N 0.000 description 1
- YWQTUYKCVLZHPV-UHFFFAOYSA-N n-[4-[n-(cyclopropylmethyl)anilino]phenyl]-1-(2,3-dihydro-1h-inden-2-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C1N(C2CC3=CC=CC=C3C2)C(=O)CC1C(=O)NC(C=C1)=CC=C1N(C=1C=CC=CC=1)CC1CC1 YWQTUYKCVLZHPV-UHFFFAOYSA-N 0.000 description 1
- JDLCJURJTRZQGP-UHFFFAOYSA-N n-[4-[n-(cyclopropylmethyl)anilino]phenyl]-1-(5-methoxy-2-methylphenyl)-5-oxopyrrolidine-3-carboxamide Chemical compound COC1=CC=C(C)C(N2C(CC(C2)C(=O)NC=2C=CC(=CC=2)N(CC2CC2)C=2C=CC=CC=2)=O)=C1 JDLCJURJTRZQGP-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- JBKYEFPEDCZWGQ-UHFFFAOYSA-N n-ethyl-4-nitro-n-phenylaniline Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(CC)C1=CC=CC=C1 JBKYEFPEDCZWGQ-UHFFFAOYSA-N 0.000 description 1
- FVFQVUSECGNYPG-UHFFFAOYSA-N n-methyl-4-nitro-n-phenylaniline Chemical compound C=1C=C([N+]([O-])=O)C=CC=1N(C)C1=CC=CC=C1 FVFQVUSECGNYPG-UHFFFAOYSA-N 0.000 description 1
- NVSYANRBXPURRQ-UHFFFAOYSA-N naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=CC2=C1 NVSYANRBXPURRQ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036299 sexual function Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 208000022925 sleep disturbance Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000003153 stable transfection Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH23812001 | 2001-12-31 | ||
| CH2381/01 | 2001-12-31 | ||
| CH0200429 | 2002-08-05 | ||
| CHPCT/CH02/00429 | 2002-08-05 | ||
| PCT/CH2002/000725 WO2003059905A1 (de) | 2001-12-31 | 2002-12-27 | Pyrrolidon-carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2471620A1 true CA2471620A1 (en) | 2003-07-24 |
Family
ID=25705687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002471620A Abandoned CA2471620A1 (en) | 2001-12-31 | 2002-12-27 | Pyrrolidone carboxamides |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1463724A1 (https=) |
| JP (1) | JP2005521651A (https=) |
| KR (1) | KR20040072697A (https=) |
| CN (1) | CN100534990C (https=) |
| AU (1) | AU2002350366A1 (https=) |
| CA (1) | CA2471620A1 (https=) |
| MX (1) | MXPA04006458A (https=) |
| WO (1) | WO2003059905A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0319151D0 (en) * | 2003-08-14 | 2003-09-17 | Glaxo Group Ltd | Novel compounds |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| US7880001B2 (en) | 2004-04-29 | 2011-02-01 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| US20100222316A1 (en) | 2004-04-29 | 2010-09-02 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US8415354B2 (en) | 2004-04-29 | 2013-04-09 | Abbott Laboratories | Methods of use of inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US8198331B2 (en) | 2005-01-05 | 2012-06-12 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| WO2006074244A2 (en) | 2005-01-05 | 2006-07-13 | Abbott Laboratories | Adamantyl derivatives as inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US20090192198A1 (en) | 2005-01-05 | 2009-07-30 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US20090264650A1 (en) * | 2005-03-31 | 2009-10-22 | Nobuo Cho | Prophylactic/Therapeutic Agent for Diabetes |
| JP4726243B2 (ja) * | 2005-08-09 | 2011-07-20 | 第一三共株式会社 | 新規セルコスポラミド誘導体 |
| WO2007018193A1 (ja) * | 2005-08-09 | 2007-02-15 | Daiichi Sankyo Company, Limited | 新規セルコスポラミド誘導体 |
| US7435833B2 (en) | 2006-04-07 | 2008-10-14 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| JP5736098B2 (ja) | 2007-08-21 | 2015-06-17 | アッヴィ・インコーポレイテッド | 中枢神経系障害を治療するための医薬組成物 |
| GB0815781D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| EP2480531B1 (en) * | 2009-09-21 | 2014-11-05 | ChemoCentryx, Inc. | Pyrrolidinone carboxamide derivatives as chemerin-r (chemr23) modulators |
| CN102827056B (zh) * | 2012-09-03 | 2014-07-23 | 华东理工大学 | N-芳基取代吡咯烷酮衍生物及其用途 |
| EP3126346B1 (en) * | 2014-04-04 | 2018-07-11 | Sanofi | Substituted indanone compounds as gpr119 modulators for the treatment of diabetes, obesity, dyslipidemia and related disorders |
| US10968176B2 (en) | 2014-09-14 | 2021-04-06 | Nanosynthons Llc | Pyrrolidone derivatives, oligomers and polymers |
| EP3194365A4 (en) * | 2014-09-14 | 2018-04-25 | Nanosynthons LLC | Pyrrolidone derivatives, oligomers and polymers |
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| GB856452A (en) * | 1957-06-27 | 1960-12-14 | Bayer Ag | Protective agents against textile pests, mould and bacteria |
| US5281612A (en) * | 1982-09-09 | 1994-01-25 | Warner-Lambert Company | Naphthyridine antibacterial agents |
| DE69025418T2 (de) * | 1989-04-19 | 1996-11-14 | Otsuka Pharma Co Ltd | Phenylcarbonsäurederivate mit einem Heterocyclus |
| US6387932B1 (en) * | 1999-06-25 | 2002-05-14 | Merck & Co., Inc. | Somatostatin agonists |
| AU6000900A (en) * | 1999-07-23 | 2001-02-13 | Astrazeneca Uk Limited | Carbazole derivatives and their use as neuropeptide y5 receptor ligands |
| GB0010757D0 (en) * | 2000-05-05 | 2000-06-28 | Astrazeneca Ab | Chemical compounds |
-
2002
- 2002-12-27 CA CA002471620A patent/CA2471620A1/en not_active Abandoned
- 2002-12-27 JP JP2003560008A patent/JP2005521651A/ja active Pending
- 2002-12-27 EP EP02785006A patent/EP1463724A1/de not_active Withdrawn
- 2002-12-27 KR KR10-2004-7010431A patent/KR20040072697A/ko not_active Withdrawn
- 2002-12-27 WO PCT/CH2002/000725 patent/WO2003059905A1/de not_active Ceased
- 2002-12-27 CN CNB028265483A patent/CN100534990C/zh not_active Expired - Fee Related
- 2002-12-27 MX MXPA04006458A patent/MXPA04006458A/es unknown
- 2002-12-27 AU AU2002350366A patent/AU2002350366A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005521651A (ja) | 2005-07-21 |
| WO2003059905A1 (de) | 2003-07-24 |
| EP1463724A1 (de) | 2004-10-06 |
| CN100534990C (zh) | 2009-09-02 |
| CN1610678A (zh) | 2005-04-27 |
| AU2002350366A1 (en) | 2003-07-30 |
| MXPA04006458A (es) | 2004-10-04 |
| KR20040072697A (ko) | 2004-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |