MX2008012617A - Compuestos organicos. - Google Patents
Compuestos organicos.Info
- Publication number
- MX2008012617A MX2008012617A MX2008012617A MX2008012617A MX2008012617A MX 2008012617 A MX2008012617 A MX 2008012617A MX 2008012617 A MX2008012617 A MX 2008012617A MX 2008012617 A MX2008012617 A MX 2008012617A MX 2008012617 A MX2008012617 A MX 2008012617A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- alkyl
- compound according
- optionally substituted
- heterocyclyl
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 339
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 530
- 125000000217 alkyl group Chemical group 0.000 claims description 317
- -1 cyano, amino, hydroxyl Chemical group 0.000 claims description 180
- 229910052739 hydrogen Inorganic materials 0.000 claims description 136
- 239000001257 hydrogen Substances 0.000 claims description 136
- 125000003545 alkoxy group Chemical group 0.000 claims description 114
- 229910052736 halogen Inorganic materials 0.000 claims description 112
- 150000002367 halogens Chemical group 0.000 claims description 112
- 125000000623 heterocyclic group Chemical group 0.000 claims description 106
- 239000000203 mixture Substances 0.000 claims description 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 85
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 83
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 150000003839 salts Chemical class 0.000 claims description 72
- 239000000651 prodrug Substances 0.000 claims description 61
- 229940002612 prodrug Drugs 0.000 claims description 61
- 125000004043 oxo group Chemical group O=* 0.000 claims description 58
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 238000002360 preparation method Methods 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000003003 spiro group Chemical group 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 31
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000003386 piperidinyl group Chemical group 0.000 claims description 28
- 125000002757 morpholinyl group Chemical group 0.000 claims description 27
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 20
- 239000003112 inhibitor Substances 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 125000002541 furyl group Chemical group 0.000 claims description 16
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 15
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 15
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 14
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 14
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 14
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000006579 5 or 6-membered monocyclic heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000006581 9 or 10-membered bicyclic heterocycloalkyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
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- 230000001419 dependent effect Effects 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 238000009472 formulation Methods 0.000 claims description 6
- 229940125396 insulin Drugs 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
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- 239000003446 ligand Substances 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 4
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 4
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- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims description 3
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- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 claims description 3
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical class O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 claims description 2
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- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical compound N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims description 2
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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| US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| PE20080403A1 (es) | 2006-07-14 | 2008-04-25 | Amgen Inc | Derivados heterociclicos fusionados y metodos de uso |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| EP2591675A1 (en) | 2006-11-27 | 2013-05-15 | H. Lundbeck A/S | Heteroaryl amide derivatives |
| WO2008124153A1 (en) | 2007-04-10 | 2008-10-16 | H. Lundbeck A/S | Heteroaryl amide analogues as p2x7 antagonists |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US8338450B2 (en) | 2007-09-21 | 2012-12-25 | Lupin Limited | Compounds as dipeptidyl peptidase IV (DPP IV) inhibitors |
| US8394823B2 (en) | 2008-04-11 | 2013-03-12 | Bristol-Myers Squibb Company | Triazolopyridine compounds useful as DGAT1 inhibitors |
| US8324241B2 (en) | 2008-04-11 | 2012-12-04 | Bristol-Myers Squibb Company | Triazolo compounds useful as DGAT1 inhibitors |
| BRPI0917540A2 (pt) | 2008-08-05 | 2015-11-17 | Daiichi Sankyo Co Ltd | composto, sal farmacologicamente aceitavél, composição farmacêutica, e, uso de um composto ou sal farmacologicamente aceitável |
| US8685967B2 (en) * | 2009-04-07 | 2014-04-01 | Merck Sharp & Dohme Corp. | Substituted triazolopyridines and analogs thereof |
| MY153913A (en) * | 2009-05-12 | 2015-04-15 | Janssen Pharmaceuticals Inc | 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors |
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| WO2011071730A1 (en) * | 2009-12-08 | 2011-06-16 | Boehringer Ingelheim International Gmbh | Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| EP2588197B1 (en) | 2010-07-02 | 2014-11-05 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| CA2822357A1 (en) | 2010-12-22 | 2012-06-28 | Abbvie Inc. | Hepatitis c inhibitors and uses thereof |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte 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 |
| 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 |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2691392A1 (en) * | 2011-03-31 | 2014-02-05 | EMBLEM Technology Transfer GmbH | Imidazo [1,2-a]pyridine compounds for use in therapy |
| KR20140033377A (ko) | 2011-05-10 | 2014-03-18 | 길리애드 사이언시즈, 인코포레이티드 | 나트륨 채널 조절제로서의 융합된 헤테로시클릭 화합물 |
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| US5559158A (en) | 1993-10-01 | 1996-09-24 | Abbott Laboratories | Pharmaceutical composition |
| SE9500051D0 (sv) * | 1995-01-09 | 1995-01-09 | Frode Rise | Antioxidants, tissue- and/or neuroprotectants |
| GB2351081A (en) * | 1999-06-18 | 2000-12-20 | Lilly Forschung Gmbh | Pharmaceutically active imidazoline compounds and analogues thereof |
| ES2316546T3 (es) * | 2001-02-20 | 2009-04-16 | Astrazeneca Ab | 2-arilamino-pirimidinas para el tratamiento de trastornos asociados a gsk3. |
| SE0100567D0 (sv) * | 2001-02-20 | 2001-02-20 | Astrazeneca Ab | Compounds |
| SI1419163T1 (sl) * | 2001-08-10 | 2005-12-31 | Altana Pharma Ag | Triciklicni imidazopiridini |
| ES2252656T3 (es) | 2002-02-13 | 2006-05-16 | F. Hoffmann-La Roche Ag | Nuevos derivados de piridina y quinolina. |
| JP4359146B2 (ja) | 2002-02-13 | 2009-11-04 | エフ．ホフマン−ラ ロシュ アーゲー | 新規なピリジン−およびピリミジン−誘導体 |
| MY139563A (en) * | 2002-09-04 | 2009-10-30 | Bristol Myers Squibb Co | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
| US7687638B2 (en) * | 2004-06-04 | 2010-03-30 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
| GB0413605D0 (en) * | 2004-06-17 | 2004-07-21 | Addex Pharmaceuticals Sa | Novel compounds |
| WO2006019965A2 (en) | 2004-07-16 | 2006-02-23 | Takeda San Diego, Inc. | Dipeptidyl peptidase inhibitors |
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- 2007-03-29 BR BRPI0710110-4A patent/BRPI0710110A2/pt not_active IP Right Cessation
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- 2007-03-29 AU AU2007233709A patent/AU2007233709A1/en not_active Abandoned
- 2007-03-29 CN CNA2007800112382A patent/CN101410397A/zh active Pending
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| KR20080104351A (ko) | 2008-12-02 |
| WO2007113226A1 (en) | 2007-10-11 |
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| BRPI0710110A2 (pt) | 2011-08-02 |
| US20120077787A1 (en) | 2012-03-29 |
| RU2008143179A (ru) | 2010-05-10 |
| US20090253689A1 (en) | 2009-10-08 |
| EP2004643A1 (en) | 2008-12-24 |
| US8097617B2 (en) | 2012-01-17 |
| CN101410397A (zh) | 2009-04-15 |
| CA2644963A1 (en) | 2007-10-11 |
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