JP2005504100A5 - - Google Patents
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- Publication number
- JP2005504100A5 JP2005504100A5 JP2003530702A JP2003530702A JP2005504100A5 JP 2005504100 A5 JP2005504100 A5 JP 2005504100A5 JP 2003530702 A JP2003530702 A JP 2003530702A JP 2003530702 A JP2003530702 A JP 2003530702A JP 2005504100 A5 JP2005504100 A5 JP 2005504100A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- trifluoromethyl
- phenyl
- 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.)
- Withdrawn
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 145
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 106
- 229910052736 halogen Inorganic materials 0.000 claims 103
- 150000002367 halogens Chemical class 0.000 claims 103
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 92
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 91
- 125000004093 cyano group Chemical group *C#N 0.000 claims 63
- -1 trifluoro Methoxy, Carboxyl Chemical group 0.000 claims 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 46
- 150000001875 compounds Chemical class 0.000 claims 45
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 43
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 239000001257 hydrogen Substances 0.000 claims 34
- 239000008194 pharmaceutical composition Substances 0.000 claims 34
- 235000019000 fluorine Nutrition 0.000 claims 31
- 229910052731 fluorine Inorganic materials 0.000 claims 28
- 239000011737 fluorine Chemical group 0.000 claims 28
- 150000002148 esters Chemical class 0.000 claims 27
- 150000003839 salts Chemical class 0.000 claims 27
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 239000003795 chemical substances by application Substances 0.000 claims 22
- 208000008589 Obesity Diseases 0.000 claims 18
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 18
- 235000020824 obesity Nutrition 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 17
- 239000004480 active ingredient Substances 0.000 claims 16
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 14
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 13
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 150000002431 hydrogen Chemical group 0.000 claims 12
- 208000035475 disorder Diseases 0.000 claims 10
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 239000003937 drug carrier Substances 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 229920006395 saturated elastomer Polymers 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 7
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 206010020772 Hypertension Diseases 0.000 claims 6
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims 6
- 239000003472 antidiabetic agent Substances 0.000 claims 6
- 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 6
- 230000029087 digestion Effects 0.000 claims 6
- 229940126904 hypoglycaemic agent Drugs 0.000 claims 6
- 230000004060 metabolic process Effects 0.000 claims 6
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 5
- 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
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
- 125000006528 (C2-C6) alkyl group Chemical group 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
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 4
- 206010037660 Pyrexia Diseases 0.000 claims 4
- 238000010521 absorption reaction Methods 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
- 125000002541 furyl group Chemical group 0.000 claims 4
- 230000005176 gastrointestinal motility Effects 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 230000036186 satiety Effects 0.000 claims 4
- 235000019627 satiety Nutrition 0.000 claims 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 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
- 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 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 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 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims 2
- ZILVNHNSYBNLSZ-UHFFFAOYSA-N 2-(diaminomethylideneamino)guanidine Chemical compound NC(N)=NNC(N)=N ZILVNHNSYBNLSZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 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
- 239000000048 adrenergic agonist Substances 0.000 claims 2
- 229940126157 adrenergic receptor agonist Drugs 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 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
- 201000011510 cancer Diseases 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 235000012631 food intake Nutrition 0.000 claims 2
- 230000037406 food intake Effects 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
- 239000000203 mixture Substances 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 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
- LPFDBVBMAURGGI-CWAVIJBDSA-N (1s,2s)-2-[1-(2-chlorophenyl)-2-(4-chlorophenyl)-6,7-dihydro-4h-pyrrolo[3,2-c]pyridin-5-yl]cyclohexan-1-ol;hydrochloride Chemical compound Cl.O[C@H]1CCCC[C@@H]1N1CC(C=C(C=2C=CC(Cl)=CC=2)N2C=3C(=CC=CC=3)Cl)=C2CC1 LPFDBVBMAURGGI-CWAVIJBDSA-N 0.000 claims 1
- BECIIBHKCYPJCG-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-(4-chlorophenyl)-5-cyclohexyl-3-methyl-6,7-dihydro-4h-pyrrolo[3,2-c]pyridine;hydrochloride Chemical compound Cl.CC=1C=2CN(C3CCCCC3)CCC=2N(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 BECIIBHKCYPJCG-UHFFFAOYSA-N 0.000 claims 1
- XHQPNKFTUAHLTD-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-(4-chlorophenyl)-5-cyclohexyl-6,7-dihydro-4h-pyrrolo[3,2-c]pyridine;hydrochloride Chemical compound Cl.C1=CC(Cl)=CC=C1C(N1C=2C(=CC=CC=2)Cl)=CC2=C1CCN(C1CCCCC1)C2 XHQPNKFTUAHLTD-UHFFFAOYSA-N 0.000 claims 1
- VMNFCTDOMRUEJN-UHFFFAOYSA-N 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-3-methyl-5-piperidin-1-yl-6,7-dihydropyrrolo[3,2-c]pyridin-4-one;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(N1C=2C(=CC=CC=2)Cl)=C(C)C(C2=O)=C1CCN2N1CCCCC1 VMNFCTDOMRUEJN-UHFFFAOYSA-N 0.000 claims 1
- VUKVNADZVKHDGS-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-[(4-fluorophenyl)methyl]-2-(4-methoxyphenyl)-6,7-dihydro-4h-pyrrolo[3,2-c]pyridine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C(N1C=2C(=CC=CC=2)Cl)=CC2=C1CCN(CC=1C=CC(F)=CC=1)C2 VUKVNADZVKHDGS-UHFFFAOYSA-N 0.000 claims 1
- JRVWFHJARYIPGM-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-cyclohexyl-2-(4-methoxyphenyl)-3-methyl-6,7-dihydropyrrolo[3,2-c]pyridin-4-one Chemical compound C1=CC(OC)=CC=C1C(N1C=2C(=CC=CC=2)Cl)=C(C)C(C2=O)=C1CCN2C1CCCCC1 JRVWFHJARYIPGM-UHFFFAOYSA-N 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- XIIMXAMBOJRASL-UHFFFAOYSA-N [1-(2-chlorophenyl)-2-(4-methoxyphenyl)-6,7-dihydro-4h-pyrrolo[3,2-c]pyridin-5-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(N1C=2C(=CC=CC=2)Cl)=CC2=C1CCN(C(=O)C=1C=CC(=CC=1)C(F)(F)F)C2 XIIMXAMBOJRASL-UHFFFAOYSA-N 0.000 claims 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 1
- HFNCOTSLOKKPHU-UHFFFAOYSA-N cyclohexanol;hydrochloride Chemical compound Cl.OC1CCCCC1 HFNCOTSLOKKPHU-UHFFFAOYSA-N 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 239000003316 glycosidase inhibitor Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32444301P | 2001-09-24 | 2001-09-24 | |
| PCT/US2002/030541 WO2003027114A1 (en) | 2001-09-24 | 2002-09-24 | Preparation and use of 1,5,6,7-tetrahydropyrrolo[3,2-c]pyridine derivatives for treatment of obesity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005504100A JP2005504100A (ja) | 2005-02-10 |
| JP2005504100A5 true JP2005504100A5 (enExample) | 2006-01-05 |
Family
ID=23263607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003530702A Withdrawn JP2005504100A (ja) | 2001-09-24 | 2002-09-24 | 肥満の治療のための１，５，６，７−テトラヒドロピロロ［３，２−ｃ］ピリジン誘導体の製造法および使用 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7071207B2 (enExample) |
| EP (1) | EP1432708B1 (enExample) |
| JP (1) | JP2005504100A (enExample) |
| AT (1) | ATE311386T1 (enExample) |
| CA (1) | CA2461142A1 (enExample) |
| DE (1) | DE60207744T2 (enExample) |
| ES (1) | ES2252524T3 (enExample) |
| MX (1) | MXPA04002249A (enExample) |
| WO (1) | WO2003027114A1 (enExample) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60334787D1 (de) | 2002-03-12 | 2010-12-16 | Merck Sharp & Dohme | Substituierte amide |
| EP1558252B1 (en) | 2002-08-02 | 2007-10-10 | Merck & Co., Inc. | Substituted furo [2,3-b]pyridine derivatives |
| 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 |
| MXPA05007114A (es) | 2003-01-02 | 2005-08-26 | Hoffmann La Roche | Nuevos agonistas inversos del receptor cb1. |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7329658B2 (en) | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid 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 |
| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands 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 |
| US20050043346A1 (en) * | 2003-08-08 | 2005-02-24 | Pharmacia Italia S.P.A. | Pyridylpyrrole derivatives active as kinase inhibitors |
| EP1660475B1 (en) * | 2003-08-08 | 2008-05-28 | Pfizer Italia S.r.l. | Pyrimidylpyrrole derivatives active as kinase inhibitors |
| US7326706B2 (en) | 2003-08-15 | 2008-02-05 | Bristol-Myers Squibb Company | Pyrazine modulators of cannabinoid receptors |
| US7151097B2 (en) | 2003-11-07 | 2006-12-19 | Pfizer Inc. | Bicyclic pyrazolyl and imidazolyl compounds and uses thereof |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| TW200602314A (en) | 2004-05-28 | 2006-01-16 | Tanabe Seiyaku Co | A novel pyrrolidine compound and a process for preparing the same |
| EP1902034B1 (en) | 2005-06-02 | 2011-03-30 | Glenmark Pharmaceuticals S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| AR056560A1 (es) | 2005-10-06 | 2007-10-10 | Astrazeneca Ab | Pirrolopiridinonas como moduladores cb1 |
| US7618982B2 (en) | 2005-12-19 | 2009-11-17 | Nerviano Medical Sciences S.R.L. | Heteroarylpyrrolopyridinones active as kinase inhibitors |
| EP1973910B1 (en) * | 2006-01-27 | 2013-06-26 | Shanghai Hengrui Pharmaceutical Co. Ltd. | Pyrrolo[3,2-c]pyridine-4-one 2-indolinone protein kinase inhibitors |
| CN101007815B (zh) * | 2006-01-27 | 2010-06-23 | 江苏恒瑞医药股份有限公司 | 吡咯并六元杂环化合物及其在医药上的用途 |
| WO2008104475A1 (en) | 2007-02-27 | 2008-09-04 | Nerviano Medical Sciences S.R.L. | Isoquinolinopyrrolopyridinones active as kinase inhibitors |
| AR065909A1 (es) * | 2007-04-03 | 2009-07-08 | Astrazeneca Ab | Agentes terapeuticos 685 |
| AR066207A1 (es) * | 2007-04-03 | 2009-08-05 | Astrazeneca Ab | Agentes terapeuticos 684 |
| WO2008134354A1 (en) * | 2007-04-27 | 2008-11-06 | Array Biopharma, Inc. | TNF-α PRODUCTION INHIBITOR |
| CN101772513B (zh) | 2007-06-04 | 2013-11-13 | 协同医药品公司 | 有效用于胃肠功能紊乱、炎症、癌症和其他疾病治疗的鸟苷酸环化酶激动剂 |
| 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 |
| EP2003129B1 (en) | 2007-06-11 | 2017-08-09 | Nerviano Medical Sciences S.r.l. | 1H-Pyrido[3,4-B]indol-1-one and 2,3,4,9-Tetrahydro-1H-Beta-Carbolin-1-one Derivatives |
| CA2726917C (en) | 2008-06-04 | 2018-06-26 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| WO2010009319A2 (en) | 2008-07-16 | 2010-01-21 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| EP2362731B1 (en) | 2008-10-31 | 2016-04-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| EP2538784B1 (en) | 2010-02-25 | 2015-09-09 | Merck Sharp & Dohme Corp. | Benzimidazole derivatives useful anti-diabetic agents |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| CA2826649C (en) | 2011-02-25 | 2016-07-26 | Merck Sharp & Dohme Corp. | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agents |
| CA2880901A1 (en) | 2012-08-02 | 2014-02-06 | 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 |
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| HK1220611A1 (zh) | 2013-03-15 | 2017-05-12 | Bausch Health Ireland Limited | 用於治疗胃肠道病症的组成物 |
| HRP20240805T1 (hr) | 2013-06-05 | 2024-09-27 | Bausch Health Ireland Limited | Ultra-pročišćeni agonisti guanilat-ciklaze c, postupak njihove pripreme i uporabe |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1484140A (en) | 1974-04-24 | 1977-08-24 | Wyeth John & Brother Ltd | Pyrrolopyridine derivatives |
| US4897390A (en) * | 1987-07-21 | 1990-01-30 | Ruhe Rodney C | Novel anti-obesity compounds and method of use |
| AU7949694A (en) * | 1993-10-20 | 1995-05-08 | Tokyo Tanabe Company Limited | Indole derivative |
| KR100251522B1 (ko) * | 1997-08-13 | 2000-08-01 | 김충섭 | 할로알콕시기를 함유하는 피롤[3,2-c]퀴놀린 유도체 및 약학적으로 허용되는 그의 염 |
| JP2002535334A (ja) | 1999-01-19 | 2002-10-22 | ニューロサーチ、アクティーゼルスカブ | 縮合ヘテロ環状化合物及びこれを神経変性疾患の治療に使用する方法 |
| MX270786B (es) * | 1999-07-06 | 2009-10-08 | Endorech Inc | Metodos de tratamiento y/o supresion del incremento de peso. |
-
2002
- 2002-09-24 ES ES02780364T patent/ES2252524T3/es not_active Expired - Lifetime
- 2002-09-24 CA CA002461142A patent/CA2461142A1/en not_active Abandoned
- 2002-09-24 JP JP2003530702A patent/JP2005504100A/ja not_active Withdrawn
- 2002-09-24 DE DE60207744T patent/DE60207744T2/de not_active Expired - Fee Related
- 2002-09-24 WO PCT/US2002/030541 patent/WO2003027114A1/en not_active Ceased
- 2002-09-24 EP EP02780364A patent/EP1432708B1/en not_active Expired - Lifetime
- 2002-09-24 AT AT02780364T patent/ATE311386T1/de not_active IP Right Cessation
- 2002-09-24 US US10/487,976 patent/US7071207B2/en not_active Expired - Fee Related
- 2002-09-24 MX MXPA04002249A patent/MXPA04002249A/es active IP Right Grant
-
2006
- 2006-01-18 US US11/335,349 patent/US20060122215A1/en not_active Abandoned
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