JP2005532982A5 - - Google Patents
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- JP2005532982A5 JP2005532982A5 JP2003530660A JP2003530660A JP2005532982A5 JP 2005532982 A5 JP2005532982 A5 JP 2005532982A5 JP 2003530660 A JP2003530660 A JP 2003530660A JP 2003530660 A JP2003530660 A JP 2003530660A JP 2005532982 A5 JP2005532982 A5 JP 2005532982A5
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- hydroxy
- alkoxy
- optionally
- 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.)
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 55
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 39
- -1 hydroxy, benzyloxy Chemical group 0.000 claims 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 30
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 26
- 150000002148 esters Chemical class 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 21
- 150000002367 halogens Chemical group 0.000 claims 20
- 229910052731 fluorine Chemical group 0.000 claims 19
- 239000011737 fluorine Chemical group 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 208000008589 Obesity Diseases 0.000 claims 18
- 239000004480 active ingredient Substances 0.000 claims 18
- 239000003795 chemical substances by application Substances 0.000 claims 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 18
- 235000020824 obesity Nutrition 0.000 claims 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 16
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 239000003814 drug Substances 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 238000011282 treatment Methods 0.000 claims 11
- 208000035475 disorder Diseases 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 239000003937 drug carrier Substances 0.000 claims 8
- 229940124597 therapeutic agent Drugs 0.000 claims 7
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 6
- 206010020772 Hypertension Diseases 0.000 claims 6
- 239000003472 antidiabetic agent Substances 0.000 claims 6
- 230000029087 digestion Effects 0.000 claims 6
- 229940079593 drug Drugs 0.000 claims 6
- 229940126904 hypoglycaemic agent Drugs 0.000 claims 6
- 230000004060 metabolic process Effects 0.000 claims 6
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 4
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims 4
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- 238000010521 absorption reaction Methods 0.000 claims 4
- 239000000048 adrenergic agonist Substances 0.000 claims 4
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 4
- 239000003613 bile acid Substances 0.000 claims 4
- 239000011230 binding agent Substances 0.000 claims 4
- 229940125753 fibrate Drugs 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 4
- 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 4
- 230000004130 lipolysis Effects 0.000 claims 4
- 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 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 230000036186 satiety Effects 0.000 claims 4
- 235000019627 satiety Nutrition 0.000 claims 4
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 3
- 230000008991 intestinal motility Effects 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 229940122199 Insulin secretagogue Drugs 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000018262 Peripheral vascular disease Diseases 0.000 claims 2
- 206010036049 Polycystic ovaries Diseases 0.000 claims 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 2
- 235000019789 appetite Nutrition 0.000 claims 2
- 230000036528 appetite Effects 0.000 claims 2
- 230000003143 atherosclerotic effect Effects 0.000 claims 2
- 230000003542 behavioural effect Effects 0.000 claims 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 201000001883 cholelithiasis Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000001149 cognitive effect Effects 0.000 claims 2
- 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 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000027950 fever generation Effects 0.000 claims 2
- 235000012631 food intake Nutrition 0.000 claims 2
- 230000037406 food intake Effects 0.000 claims 2
- 239000003316 glycosidase inhibitor Substances 0.000 claims 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 2
- 231100000535 infertility Toxicity 0.000 claims 2
- 208000000509 infertility Diseases 0.000 claims 2
- 230000036512 infertility Effects 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 231100000551 menstrual abnormality Toxicity 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 201000002859 sleep apnea Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 230000035924 thermogenesis Effects 0.000 claims 2
- GATYVSWNUQBZOD-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-2-methyl-n'-[2-(trifluoromethyl)phenyl]pyrrole-3-carbohydrazide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(C)=C(C(=O)NNC=2C(=CC=CC=2)C(F)(F)F)C=C1C1=CC=C(Cl)C=C1 GATYVSWNUQBZOD-UHFFFAOYSA-N 0.000 claims 1
- BLARRMGRSJWTAH-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-2-methyl-n-piperidin-1-ylpyrrole-3-carboxamide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(C)=C(C(=O)NN2CCCCC2)C=C1C1=CC=C(Cl)C=C1 BLARRMGRSJWTAH-UHFFFAOYSA-N 0.000 claims 1
- NTHSSZABQKWIRH-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-2,4-dimethyl-n'-[4-(trifluoromethyl)phenyl]pyrrole-3-carbohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=C(C)C(C(=O)NNC=2C=CC(=CC=2)C(F)(F)F)=C(C)N1C1=CC=CC=C1Cl NTHSSZABQKWIRH-UHFFFAOYSA-N 0.000 claims 1
- WGXPKLSREJJEQA-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-2-methyl-n'-[2-(trifluoromethyl)phenyl]pyrrole-3-carbohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC(C(=O)NNC=2C(=CC=CC=2)C(F)(F)F)=C(C)N1C1=CC=CC=C1Cl WGXPKLSREJJEQA-UHFFFAOYSA-N 0.000 claims 1
- GMLVYNLULIEDNB-UHFFFAOYSA-N 2-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-n-cyclohexylpyrrole-3-carboxamide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(N)=C(C(=O)NC2CCCCC2)C=C1C1=CC=C(Cl)C=C1 GMLVYNLULIEDNB-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- HJNXURHVMIPLQX-OFNKIYASSA-N 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n-[(1r,2s)-2-hydroxycyclohexyl]-2-methylpyrrole-3-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(C)=C(C(=O)N[C@H]2[C@H](CCCC2)O)C=C1C1=CC=C(Cl)C=C1 HJNXURHVMIPLQX-OFNKIYASSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 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 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 230000010243 gut motility Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32444101P | 2001-09-24 | 2001-09-24 | |
| PCT/US2002/030543 WO2003027069A1 (en) | 2001-09-24 | 2002-09-24 | Preparation and use of pyrrole derivatives for treating obesity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005532982A JP2005532982A (ja) | 2005-11-04 |
| JP2005532982A5 true JP2005532982A5 (enExample) | 2006-01-05 |
Family
ID=23263599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003530660A Withdrawn JP2005532982A (ja) | 2001-09-24 | 2002-09-24 | 肥満の処置のためのピロール誘導体の製造及び使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20040267028A1 (enExample) |
| EP (1) | EP1432679A1 (enExample) |
| JP (1) | JP2005532982A (enExample) |
| CA (1) | CA2461144A1 (enExample) |
| MX (1) | MXPA04002438A (enExample) |
| WO (1) | WO2003027069A1 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003077847A2 (en) | 2002-03-12 | 2003-09-25 | Merck & Co., Inc. | Substituted amides |
| US7129239B2 (en) | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US7247628B2 (en) | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| GB0230088D0 (en) * | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| GB0230087D0 (en) * | 2002-12-24 | 2003-01-29 | Astrazeneca Ab | Therapeutic agents |
| CN101012193A (zh) | 2003-01-02 | 2007-08-08 | 霍夫曼-拉罗奇有限公司 | 新cb 1受体反激动剂 |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| GB0302671D0 (en) * | 2003-02-06 | 2003-03-12 | Astrazeneca Ab | Pharmaceutical formulations |
| US7329658B2 (en) | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| GB0302672D0 (en) * | 2003-02-06 | 2003-03-12 | Astrazeneca Ab | Pharmaceutical formulations |
| US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7268133B2 (en) | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
| CA2523808A1 (en) | 2003-05-16 | 2004-12-23 | Ambit Biosciences Corporation | Pyrrole compounds and uses thereof |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| US7276608B2 (en) | 2003-07-11 | 2007-10-02 | Bristol-Myers Squibb Company | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
| US7326706B2 (en) | 2003-08-15 | 2008-02-05 | Bristol-Myers Squibb Company | Pyrazine modulators of cannabinoid receptors |
| MXPA06004642A (es) | 2003-11-05 | 2006-06-27 | Hoffmann La Roche | Derivados de heteroaril como activadores de los receptores activados de proliferadores de peroxisoma (ppar). |
| GB0403780D0 (en) * | 2004-02-20 | 2004-03-24 | Astrazeneca Ab | Therapeutic agents |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| ES2324720T3 (es) | 2004-05-10 | 2009-08-13 | F. Hoffmann-La Roche Ag | Pirrol o imidazol amidas para tratar la obesidad. |
| TW200602314A (en) | 2004-05-28 | 2006-01-16 | Tanabe Seiyaku Co | A novel pyrrolidine compound and a process for preparing the same |
| JP4703649B2 (ja) * | 2004-07-30 | 2011-06-15 | エグゼリクシス， インコーポレイテッド | 薬学的因子としてのピロール誘導体 |
| PL1902034T3 (pl) | 2005-06-02 | 2011-09-30 | Glenmark Pharmaceuticals Sa | Nowe ligandy receptorów kanabinoidowych, kompozycja farmaceutyczna je zawierająca oraz proces ich wytwarzania |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| WO2007020502A2 (en) * | 2005-08-16 | 2007-02-22 | Pharmacia & Upjohn Company Llc | Cannabinoid receptor ligands and uses thereof |
| BRPI0715160A2 (pt) | 2006-08-08 | 2013-06-11 | Sanofi Aventis | imidazolidina-2,4-dionas substituÍdas por arilamimoaril-alquil-, processo para preparÁ-las, medicamentos compeendendo estes compostos, e seu uso |
| WO2008126831A1 (ja) * | 2007-04-09 | 2008-10-23 | Daiichi Sankyo Company, Limited | ピロール誘導体のアトロプ異性体 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2393885T7 (es) | 2007-06-04 | 2014-01-30 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2009131814A2 (en) * | 2008-04-22 | 2009-10-29 | Eli Lilly And Company | 1,5-diphenyl-pyrrolidin-2-one compounds as cb-1 ligands |
| FR2930939B1 (fr) * | 2008-05-09 | 2010-07-30 | Sanofi Aventis | Derives de pyrrole, leur preparation et leur application en therapeutique |
| WO2009149279A2 (en) | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| CA2741125A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| CN102271509A (zh) | 2008-10-31 | 2011-12-07 | 默沙东公司 | 用于抗糖尿病药的新型环苯并咪唑衍生物 |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| ES2443016T3 (es) | 2009-08-26 | 2014-02-17 | Sanofi | Nuevos hidratos cristalinos de fluoroglicósidos heteroaromáticos, productos farmacéuticos que comprenden estos compuestos, y su empleo |
| AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| KR101668514B1 (ko) | 2011-02-25 | 2016-10-21 | 머크 샤프 앤드 돔 코포레이션 | 항당뇨병제로서 유용한 신규 시클릭 아자벤즈이미다졸 유도체 |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012120055A1 (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 |
| WO2012120053A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-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 |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte 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 |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| KR101404185B1 (ko) | 2012-03-09 | 2014-06-11 | 연세대학교 산학협력단 | Ｗｎｔ／β-카테닌 신호전달계와 관련된 질병의 예방 및 치료용 약학 조성물 |
| EP2880028B1 (en) | 2012-08-02 | 2020-09-30 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| CN104994848A (zh) | 2013-02-22 | 2015-10-21 | 默沙东公司 | 抗糖尿病二环化合物 |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| US9486494B2 (en) | 2013-03-15 | 2016-11-08 | Synergy Pharmaceuticals, Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| EP3004138B1 (en) | 2013-06-05 | 2024-03-13 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI94339C (fi) * | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| WO2002010158A2 (en) * | 2000-07-27 | 2002-02-07 | F. Hoffmann-La Roche Ag | 3-indolyl-4-phenyl-1h-pyrrole-2,5-dione derivatives as inhibitors of glycogen synthase kinase-3beta |
-
2002
- 2002-09-24 US US10/489,031 patent/US20040267028A1/en not_active Abandoned
- 2002-09-24 CA CA002461144A patent/CA2461144A1/en not_active Abandoned
- 2002-09-24 JP JP2003530660A patent/JP2005532982A/ja not_active Withdrawn
- 2002-09-24 EP EP02799637A patent/EP1432679A1/en not_active Withdrawn
- 2002-09-24 MX MXPA04002438A patent/MXPA04002438A/es unknown
- 2002-09-24 WO PCT/US2002/030543 patent/WO2003027069A1/en not_active Ceased
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