AU2009225441B2 - Novel piperidine derivatives as inhibitors of stearoyl-CoA desaturase - Google Patents
Novel piperidine derivatives as inhibitors of stearoyl-CoA desaturase Download PDFInfo
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- AU2009225441B2 AU2009225441B2 AU2009225441A AU2009225441A AU2009225441B2 AU 2009225441 B2 AU2009225441 B2 AU 2009225441B2 AU 2009225441 A AU2009225441 A AU 2009225441A AU 2009225441 A AU2009225441 A AU 2009225441A AU 2009225441 B2 AU2009225441 B2 AU 2009225441B2
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- Prior art keywords
- compound
- piperidin
- phenyl
- oxo
- ethyl
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- 108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 11
- 239000003112 inhibitor Substances 0.000 title claims abstract description 9
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims abstract 5
- 150000003053 piperidines Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 229
- 238000000034 method Methods 0.000 claims abstract description 43
- -1 cyano, nitro, amino Chemical group 0.000 claims description 171
- 150000003839 salts Chemical class 0.000 claims description 94
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 125000001072 heteroaryl group Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 58
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 239000012453 solvate Substances 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
- 208000008589 Obesity Diseases 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000003368 amide group Chemical group 0.000 claims description 11
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 8
- XJYOBHXWBRKOQO-UHFFFAOYSA-N 5-phenyl-1,2-oxazole-3-carboxylic acid Chemical compound O1N=C(C(=O)O)C=C1C1=CC=CC=C1 XJYOBHXWBRKOQO-UHFFFAOYSA-N 0.000 claims description 8
- 150000004677 hydrates Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- DBYLAWFMMVZTRR-UHFFFAOYSA-N 1-phenylimidazole-4-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN1C1=CC=CC=C1 DBYLAWFMMVZTRR-UHFFFAOYSA-N 0.000 claims description 5
- BVXVSCNTHVGDRU-UHFFFAOYSA-N N-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-5-(2-hydroxyphenyl)-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C(=CC=CC=2)Cl)=NO1 BVXVSCNTHVGDRU-UHFFFAOYSA-N 0.000 claims description 4
- WFAALKOUHKWGCA-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-3-(3-hydroxyphenyl)-1h-pyrazole-5-carboxamide Chemical compound OC1=CC=CC(C=2NN=C(C=2)C(=O)NCC(=O)N2CCC(CC2)NC=2C(=CC=CC=2)Cl)=C1 WFAALKOUHKWGCA-UHFFFAOYSA-N 0.000 claims description 4
- NCKQFZBBVWTDSR-UHFFFAOYSA-N n-[2-oxo-2-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-4-phenylbenzamide Chemical compound FC(F)(F)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 NCKQFZBBVWTDSR-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- AMBDRXRCOGOEHY-UHFFFAOYSA-N 6-anilino-n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]pyridine-3-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=NC(NC=3C=CC=CC=3)=CC=2)CC1 AMBDRXRCOGOEHY-UHFFFAOYSA-N 0.000 claims description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- YXWTVUAGHOZUIC-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 YXWTVUAGHOZUIC-UHFFFAOYSA-N 0.000 claims description 3
- YVDSFJVIPJIDDM-UHFFFAOYSA-N 1-(3-methylphenyl)-n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]triazole-4-carboxamide Chemical compound CC1=CC=CC(N2N=NC(=C2)C(=O)NCC(=O)N2CCC(CC2)OC=2C=C(C=CC=2)C(F)(F)F)=C1 YVDSFJVIPJIDDM-UHFFFAOYSA-N 0.000 claims description 2
- FUQVEOXNFSKAFB-UHFFFAOYSA-N 2-[1-[2-[(3-phenyl-1h-pyrazole-5-carbonyl)amino]acetyl]piperidin-4-yl]oxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 FUQVEOXNFSKAFB-UHFFFAOYSA-N 0.000 claims description 2
- BBFVYPZHDREFSP-UHFFFAOYSA-N 3-[2-(trifluoromethyl)phenyl]-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C(=CC=CC=2)C(F)(F)F)=N1 BBFVYPZHDREFSP-UHFFFAOYSA-N 0.000 claims description 2
- GFQYKYPGSBTSII-HHHXNRCGSA-N 4-[[(2r)-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl]methoxy]-n-[2-oxo-2-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]ethyl]benzamide Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1C(=O)NCC(=O)N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 GFQYKYPGSBTSII-HHHXNRCGSA-N 0.000 claims description 2
- BPKQAZUPMXCHJJ-UHFFFAOYSA-N 5-(3-hydroxyphenyl)-n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC(C=2ON=C(C=2)C(=O)NCC(=O)N2CCC(CC2)OC=2C=C(C=CC=2)C(F)(F)F)=C1 BPKQAZUPMXCHJJ-UHFFFAOYSA-N 0.000 claims description 2
- ZYFRBEJYRHBUSJ-UHFFFAOYSA-N C1CN(C(=O)CN)CCC1OC1=CC=CC=C1Cl Chemical compound C1CN(C(=O)CN)CCC1OC1=CC=CC=C1Cl ZYFRBEJYRHBUSJ-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- DNSOZZOLYMPPRJ-UHFFFAOYSA-N n-[2-[3-(2-chlorophenoxy)pyrrolidin-1-yl]-2-oxoethyl]-1-pyridin-3-yltriazole-4-carboxamide Chemical compound ClC1=CC=CC=C1OC1CN(C(=O)CNC(=O)C=2N=NN(C=2)C=2C=NC=CC=2)CC1 DNSOZZOLYMPPRJ-UHFFFAOYSA-N 0.000 claims description 2
- BZDPLIAACVTKNV-UHFFFAOYSA-N n-[2-[3-[3-fluoro-5-(trifluoromethyl)phenoxy]azetidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC(OC2CN(C2)C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)=C1 BZDPLIAACVTKNV-UHFFFAOYSA-N 0.000 claims description 2
- DBGFNCYANRRSIL-UHFFFAOYSA-N n-[2-[4-(2,5-dimethylanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=CC=C(C)C(NC2CCN(CC2)C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)=C1 DBGFNCYANRRSIL-UHFFFAOYSA-N 0.000 claims description 2
- IMNSGCAUWONPEE-UHFFFAOYSA-N n-[2-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-2-oxoethyl]-2-phenyl-4h-thieno[3,2-b]pyrrole-5-carboxamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CNC(=O)C=2NC=3C=C(SC=3C=2)C=2C=CC=CC=2)=C1 IMNSGCAUWONPEE-UHFFFAOYSA-N 0.000 claims description 2
- QFLWLFPNIDECHE-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-1-(3,5-difluorophenyl)triazole-4-carboxamide Chemical compound FC1=CC(F)=CC(N2N=NC(=C2)C(=O)NCC(=O)N2CCC(CC2)OC=2C(=CC=CC=2)Cl)=C1 QFLWLFPNIDECHE-UHFFFAOYSA-N 0.000 claims description 2
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- MCTHOEYUMWNULO-UHFFFAOYSA-N n-[2-[4-(2-hydroxyphenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound OC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 MCTHOEYUMWNULO-UHFFFAOYSA-N 0.000 claims description 2
- USXJGPACGOUYCA-UHFFFAOYSA-N n-[2-[4-(2-methylpyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=NC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 USXJGPACGOUYCA-UHFFFAOYSA-N 0.000 claims description 2
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- OBYSXHARNGLINB-UHFFFAOYSA-N n-[2-[4-(3-cyanoanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound C1CC(NC=2C=C(C=CC=2)C#N)CCN1C(=O)CNC(=O)C(=NN1)C=C1C1=CC=CC=C1 OBYSXHARNGLINB-UHFFFAOYSA-N 0.000 claims description 2
- TYBVKIPMLUSAOJ-UHFFFAOYSA-N n-[2-[4-(3-cyanophenoxy)piperidin-1-yl]-2-oxoethyl]-1-phenyltriazole-4-carboxamide Chemical compound C1CC(OC=2C=C(C=CC=2)C#N)CCN1C(=O)CNC(=O)C(N=N1)=CN1C1=CC=CC=C1 TYBVKIPMLUSAOJ-UHFFFAOYSA-N 0.000 claims description 2
- RTNRLPYMJXGTBZ-UHFFFAOYSA-N n-[2-[4-(4-methylpyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=CC=NC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 RTNRLPYMJXGTBZ-UHFFFAOYSA-N 0.000 claims description 2
- GQEVORZFWKDZJE-UHFFFAOYSA-N n-[2-[4-(5-chloropyridin-3-yl)oxypiperidin-1-yl]-2-oxoethyl]-3-(4-fluorophenyl)-1h-pyrazole-5-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C=C(Cl)C=NC=2)=NN1 GQEVORZFWKDZJE-UHFFFAOYSA-N 0.000 claims description 2
- PEUIQJVBBWBMSQ-UHFFFAOYSA-N n-[2-[4-(5-cyano-2-methylphenoxy)piperidin-1-yl]-2-oxoethyl]-1-pyridin-3-yltriazole-4-carboxamide Chemical compound CC1=CC=C(C#N)C=C1OC1CCN(C(=O)CNC(=O)C=2N=NN(C=2)C=2C=NC=CC=2)CC1 PEUIQJVBBWBMSQ-UHFFFAOYSA-N 0.000 claims description 2
- LKWPGLCZVNYLPL-UHFFFAOYSA-N n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-4-(pyrrolidine-1-carbonyl)benzamide Chemical compound FC(F)(F)C1=CC=CC(OC2CCN(CC2)C(=O)CNC(=O)C=2C=CC(=CC=2)C(=O)N2CCCC2)=C1 LKWPGLCZVNYLPL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 229940123980 Desaturase inhibitor Drugs 0.000 claims 2
- RWKMMQRQJJXJNX-UHFFFAOYSA-N N-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-5-(2-hydroxyphenyl)-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)NC=2C(=CC=CC=2)Cl)=NO1 RWKMMQRQJJXJNX-UHFFFAOYSA-N 0.000 claims 1
- OGWBHUYCALEIPO-UHFFFAOYSA-N n-[2-[4-(2-acetylphenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC(=O)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 OGWBHUYCALEIPO-UHFFFAOYSA-N 0.000 claims 1
- GNSCZTQFUZQSLY-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-1-phenylpyrazole-4-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=CN(N=C2)C=2C=CC=CC=2)CC1 GNSCZTQFUZQSLY-UHFFFAOYSA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN575/KOL/2008 | 2008-03-20 | ||
| IN575KO2008 | 2008-03-20 | ||
| US4948008P | 2008-05-01 | 2008-05-01 | |
| US61/049,480 | 2008-05-01 | ||
| PCT/US2009/037835 WO2009117676A2 (en) | 2008-03-20 | 2009-03-20 | Novel piperidine derivatives as inhibitors of stearoyl-coa desaturase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2009225441A1 AU2009225441A1 (en) | 2009-09-24 |
| AU2009225441B2 true AU2009225441B2 (en) | 2012-12-13 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009225441A Expired - Fee Related AU2009225441B2 (en) | 2008-03-20 | 2009-03-20 | Novel piperidine derivatives as inhibitors of stearoyl-CoA desaturase |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8129376B2 (OSRAM) |
| EP (1) | EP2268143A4 (OSRAM) |
| JP (1) | JP2011518774A (OSRAM) |
| KR (1) | KR20100134680A (OSRAM) |
| CN (1) | CN102036558A (OSRAM) |
| AU (1) | AU2009225441B2 (OSRAM) |
| BR (1) | BRPI0909183A2 (OSRAM) |
| CA (1) | CA2719000A1 (OSRAM) |
| IL (1) | IL208232A0 (OSRAM) |
| MX (1) | MX2010010241A (OSRAM) |
| NZ (1) | NZ588633A (OSRAM) |
| RU (1) | RU2010142937A (OSRAM) |
| WO (1) | WO2009117676A2 (OSRAM) |
| ZA (1) | ZA201007252B (OSRAM) |
Families Citing this family (30)
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|---|---|---|---|---|
| WO2009051244A1 (ja) | 2007-10-18 | 2009-04-23 | Takeda Pharmaceutical Company Limited | 複素環化合物 |
| US8642583B2 (en) | 2008-10-30 | 2014-02-04 | Janssen Pharmaceutica Nv | Serotonin receptor modulators |
| SG182662A1 (en) | 2010-01-28 | 2012-08-30 | Harvard College | Compositions and methods for enhancing proteasome activity |
| JP5996532B2 (ja) | 2010-07-15 | 2016-09-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 有害生物防除剤としての新規複素環式化合物 |
| WO2012154967A1 (en) | 2011-05-12 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| NO2686520T3 (OSRAM) | 2011-06-06 | 2018-03-17 | ||
| FR3000491B1 (fr) * | 2012-09-27 | 2015-08-28 | Univ Lille Ii Droit & Sante | Composes utilisables dans le traitement des infections mycobacteriennes |
| CN103772267A (zh) * | 2012-10-24 | 2014-05-07 | 常州化学研究所 | 一种二苯胺制备咔唑的方法 |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| UA118034C2 (uk) * | 2013-11-14 | 2018-11-12 | Елі Ліллі Енд Компані | Заміщений піперидилетилпіримідин як інгібітор грелін-o-ацилтрансферази |
| SG11201607920RA (en) | 2014-04-04 | 2016-10-28 | X Rx Inc | Substituted spirocyclic inhibitors of autotaxin |
| BR112016024473A2 (pt) * | 2014-04-23 | 2018-01-23 | X Rx Inc | composto, composição farmacêutica, e, método para tratamento de uma doença e/ou condição |
| US20160047307A1 (en) * | 2014-08-15 | 2016-02-18 | General Electric Company | Power train architectures with low-loss lubricant bearings and low-density materials |
| WO2016054560A1 (en) | 2014-10-02 | 2016-04-07 | Flatley Discovery Lab | Isoxazole compounds and methods for the treatment of cystic fibrosis |
| CN106432232A (zh) * | 2016-09-18 | 2017-02-22 | 苏州汉德创宏生化科技有限公司 | 1‑哌啶‑4‑基‑1,3‑二氢‑咪唑[4,5‑b]吡啶‑2‑酮的合成方法 |
| US11384081B2 (en) | 2016-09-20 | 2022-07-12 | Centre Leon Berard | Benzoimidazole derivatives as anticancer agents |
| US11970486B2 (en) | 2016-10-24 | 2024-04-30 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
| JP2020514293A (ja) | 2017-01-06 | 2020-05-21 | ユマニティ セラピューティクス,インコーポレーテッド | 神経障害を治療する方法 |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| CN107663184A (zh) * | 2017-11-15 | 2018-02-06 | 上海皓伯化工科技有限公司 | 一种N‑Boc‑4‑羟基哌啶的合成方法 |
| EP3768269B1 (en) | 2018-03-23 | 2025-08-20 | Janssen Pharmaceutica NV | Compounds and uses thereof |
| US10919885B2 (en) | 2018-04-25 | 2021-02-16 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| MX2020011845A (es) | 2018-05-09 | 2021-01-15 | Akebia Therapeutics Inc | Proceso para preparar acido 2-[[5-(3-clorofenil)-3-hidroxipiridina -2-carbonil]amino]acetico. |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| MX2021008903A (es) * | 2019-01-24 | 2021-11-04 | Yumanity Therapeutics Inc | Compuestos y usos de los mismos. |
| CA3148310A1 (en) * | 2019-09-13 | 2021-03-18 | Jun Qi | Kdm inhibitors and uses thereof |
| CN110845396B (zh) * | 2019-11-07 | 2023-01-20 | 宿迁联盛科技股份有限公司 | 一种2,2,6,6-四甲基-4-哌啶胺类化合物的制备方法 |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004074283A1 (en) * | 2003-02-21 | 2004-09-02 | Pfizer Inc. | N-heterocyclyl-substituted amino-thiazole derivatives as protein kinase inhibitors |
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|---|---|---|---|---|
| AU6659090A (en) | 1989-11-16 | 1991-06-13 | Warner-Lambert Company | Acat inhibitors |
| US5459151A (en) | 1993-04-30 | 1995-10-17 | American Home Products Corporation | N-acyl substituted phenyl piperidines as bronchodilators and antiinflammatory agents |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| CA2186371A1 (en) | 1994-03-25 | 1995-10-05 | Robert T. Foster | Enhancement of the efficacy of dihydropyridines by deuteration |
| CA2398940C (en) | 2000-02-24 | 2012-02-21 | Xenon Genetics, Inc. | Methods and compositions using stearoyl-coa desaturase to identify triglyceride reducing therapeutic agents |
| DE60134995D1 (de) | 2000-09-26 | 2008-09-04 | Xenon Pharmaceuticals Inc | Verfahren und zusammensetzungen, die eine stearoyl-coa desuturase-hscd5 verwenden |
| KR20050045927A (ko) | 2003-11-12 | 2005-05-17 | 주식회사 엘지생명과학 | 멜라노코틴 수용체의 항진제 |
| JP4787529B2 (ja) * | 2004-04-09 | 2011-10-05 | 大塚製薬株式会社 | 医薬組成物 |
| MX2007003319A (es) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| CN101084212A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途 |
| CN101090724A (zh) * | 2004-09-20 | 2007-12-19 | 泽农医药公司 | 用于抑制人硬脂酰CoA去饱和酶的吡啶衍生物 |
| WO2008157844A1 (en) * | 2007-06-21 | 2008-12-24 | Forest Laboratories Holdings Limited | Novel piperazine derivatives as inhibitors of stearoyl-coa desaturase |
| JPWO2009119537A1 (ja) * | 2008-03-26 | 2011-07-21 | 第一三共株式会社 | ヒドロキシキノキサリンカルボキサミド誘導体 |
-
2009
- 2009-03-20 RU RU2010142937/04A patent/RU2010142937A/ru unknown
- 2009-03-20 US US12/408,486 patent/US8129376B2/en not_active Expired - Fee Related
- 2009-03-20 EP EP09721822A patent/EP2268143A4/en not_active Withdrawn
- 2009-03-20 WO PCT/US2009/037835 patent/WO2009117676A2/en not_active Ceased
- 2009-03-20 NZ NZ588633A patent/NZ588633A/en not_active IP Right Cessation
- 2009-03-20 CN CN2009801176982A patent/CN102036558A/zh active Pending
- 2009-03-20 KR KR1020107023415A patent/KR20100134680A/ko not_active Ceased
- 2009-03-20 AU AU2009225441A patent/AU2009225441B2/en not_active Expired - Fee Related
- 2009-03-20 BR BRPI0909183-1A patent/BRPI0909183A2/pt not_active IP Right Cessation
- 2009-03-20 MX MX2010010241A patent/MX2010010241A/es active IP Right Grant
- 2009-03-20 JP JP2011500989A patent/JP2011518774A/ja active Pending
- 2009-03-20 CA CA2719000A patent/CA2719000A1/en not_active Abandoned
-
2010
- 2010-09-19 IL IL208232A patent/IL208232A0/en unknown
- 2010-10-11 ZA ZA2010/07252A patent/ZA201007252B/en unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004074283A1 (en) * | 2003-02-21 | 2004-09-02 | Pfizer Inc. | N-heterocyclyl-substituted amino-thiazole derivatives as protein kinase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201007252B (en) | 2011-12-28 |
| US20090239810A1 (en) | 2009-09-24 |
| KR20100134680A (ko) | 2010-12-23 |
| EP2268143A4 (en) | 2012-06-27 |
| AU2009225441A1 (en) | 2009-09-24 |
| RU2010142937A (ru) | 2012-04-27 |
| MX2010010241A (es) | 2010-12-06 |
| NZ588633A (en) | 2012-03-30 |
| BRPI0909183A2 (pt) | 2015-08-25 |
| IL208232A0 (en) | 2010-12-30 |
| EP2268143A2 (en) | 2011-01-05 |
| US8129376B2 (en) | 2012-03-06 |
| CN102036558A (zh) | 2011-04-27 |
| WO2009117676A3 (en) | 2010-01-07 |
| WO2009117676A2 (en) | 2009-09-24 |
| JP2011518774A (ja) | 2011-06-30 |
| CA2719000A1 (en) | 2009-09-24 |
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| Date | Code | Title | Description |
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| MK25 | Application lapsed reg. 22.2i(2) - failure to pay acceptance fee |