RU2358974C2 - Производные имидазо-пиридина, обладающие сродством к рецептору меланокортина - Google Patents
Производные имидазо-пиридина, обладающие сродством к рецептору меланокортина Download PDFInfo
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- RU2358974C2 RU2358974C2 RU2005133441/04A RU2005133441A RU2358974C2 RU 2358974 C2 RU2358974 C2 RU 2358974C2 RU 2005133441/04 A RU2005133441/04 A RU 2005133441/04A RU 2005133441 A RU2005133441 A RU 2005133441A RU 2358974 C2 RU2358974 C2 RU 2358974C2
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- Prior art keywords
- alkyl
- compound
- substituted
- hydrogen atom
- formula
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- 102000004378 Melanocortin Receptors Human genes 0.000 title claims abstract description 14
- 108090000950 Melanocortin Receptors Proteins 0.000 title claims abstract description 14
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 208000035475 disorder Diseases 0.000 claims abstract description 10
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- 230000036407 pain Effects 0.000 claims abstract description 6
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 6
- 230000037396 body weight Effects 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 150000002367 halogens Chemical class 0.000 claims description 55
- -1 moreover Chemical group 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 39
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 28
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
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- 206010006895 Cachexia Diseases 0.000 claims description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 239000000010 aprotic solvent Substances 0.000 claims description 16
- 150000002540 isothiocyanates Chemical class 0.000 claims description 13
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 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 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
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- 230000036506 anxiety Effects 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
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- 206010061428 decreased appetite Diseases 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims description 4
- 208000004296 neuralgia Diseases 0.000 claims description 4
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- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 3
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- 239000000126 substance Substances 0.000 abstract 1
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- 150000003254 radicals Chemical class 0.000 description 59
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- 239000000203 mixture Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 230000002829 reductive effect Effects 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 21
- 239000003480 eluent Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 238000003818 flash chromatography Methods 0.000 description 18
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- 238000000746 purification Methods 0.000 description 17
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- 239000012267 brine Substances 0.000 description 15
- 238000010908 decantation Methods 0.000 description 15
- 238000000605 extraction Methods 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
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- 239000000706 filtrate Substances 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
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- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 description 12
- 102000008316 Type 4 Melanocortin Receptor Human genes 0.000 description 12
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 12
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- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 6
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- 239000002865 melanocortin Substances 0.000 description 6
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- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 5
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- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 4
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- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
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- UNZYWGIXVVCSAX-UHFFFAOYSA-N tert-butyl n-[4-(methoxycarbamoylamino)phenyl]carbamate Chemical compound CONC(=O)NC1=CC=C(NC(=O)OC(C)(C)C)C=C1 UNZYWGIXVVCSAX-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D471/02—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 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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| FR0303924A FR2852957B1 (fr) | 2003-03-31 | 2003-03-31 | Nouveaux derives d'imidazo-pyridine et leur utilisation en tant que medicament |
| FR03/03924 | 2003-03-31 |
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| RU2005133441A RU2005133441A (ru) | 2006-05-10 |
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| MX (1) | MXPA05010278A (enExample) |
| NZ (1) | NZ542763A (enExample) |
| RU (1) | RU2358974C2 (enExample) |
| WO (1) | WO2004089951A1 (enExample) |
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| FR2862971B1 (fr) * | 2003-11-28 | 2006-03-24 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et d'imidazo-pyridine et leur utilisation en tant que medicament |
| TW200911803A (en) * | 2007-07-16 | 2009-03-16 | Organon Nv | 6-phenyl-1H-imidazo [4,5-c] pyridine-4-carbonitrile derivatives |
| EP2072516A1 (en) * | 2007-12-21 | 2009-06-24 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine derivates as Melancortin-4 receptor antagonists |
| EP2072050A1 (en) | 2007-12-21 | 2009-06-24 | Santhera Pharmaceuticals (Schweiz) AG | Compounds with anti-emetic effect |
| EP2168965A1 (en) * | 2008-09-25 | 2010-03-31 | Santhera Pharmaceuticals (Schweiz) AG | Substituted imidazopyridine, imidazopyrazine, imidazopyridazine and imidazopyrimidine derivatives as melanocortin-4 receptor antagonists |
| UY32138A (es) * | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| 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 |
| UY32470A (es) * | 2009-03-05 | 2010-10-29 | Boehringer Ingelheim Int | Derivados de 2-{2-cloro-5-[(sustituido) metil]fenilamino} -1-metil]fenilamino}-1-metilbencimidazol-5-carboxamidas-n-(sustituidas) y sus sales fisiológicamente aceptables, composiciones conteniéndolos y aplicaciones |
| AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| RU2013109143A (ru) | 2010-08-05 | 2014-09-10 | Амджен Инк. | Бензимидазол- и азабензимидазолсодержащие соединения, которые ингибируют киназу анапластической лимфомы |
| US8759537B2 (en) | 2010-08-20 | 2014-06-24 | Boehringer Ingelheim International Gmbh | 3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents |
| US8586604B2 (en) | 2010-08-20 | 2013-11-19 | Boehringer Ingelheim International Gmbh | Inhibitors of the microsomal prostaglandin E2 synthase-1 |
| US8486968B2 (en) | 2010-12-10 | 2013-07-16 | Boehringer Ingelheim International Gmbh | Compounds |
| US8674113B2 (en) | 2010-12-10 | 2014-03-18 | Boehringer Ingelheim International Gmbh | Compounds |
| US8466186B2 (en) | 2010-12-10 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Compounds |
| CA2825098C (en) | 2011-01-27 | 2020-03-10 | Universite De Montreal | Pyrazolopyridine and pyrazolopyrimidine derivatives as melanocortin-4 receptor modulators |
| KR101668514B1 (ko) | 2011-02-25 | 2016-10-21 | 머크 샤프 앤드 돔 코포레이션 | 항당뇨병제로서 유용한 신규 시클릭 아자벤즈이미다졸 유도체 |
| LT3539551T (lt) | 2011-12-29 | 2022-01-10 | Rhythm Pharmaceuticals, Inc. | Su melanokortino-4 receptoriumi susijusių sutrikimų gydymo būdas heterozigotiniuose nešiotojuose |
| HK1206735A1 (en) * | 2012-04-06 | 2016-01-15 | 辉瑞公司 | Diacylglycerol acyltransferase 2 inhibitors |
| 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 |
| US10196425B2 (en) | 2013-03-15 | 2019-02-05 | Rhythm Pharmaceuticals, Inc. | Peptide compositions |
| EP2970389B1 (en) | 2013-03-15 | 2020-08-19 | Rhythm Pharmaceuticals, Inc. | Pharmaceutical compositions |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| TWI663159B (zh) | 2013-12-10 | 2019-06-21 | 美商健臻公司 | 原肌球蛋白相關之激酶（ｔｒｋ）抑制劑 |
| SG11201704872RA (en) | 2014-12-18 | 2017-07-28 | Genzyme Corp | Pharmaceutical formulations of tropomyosin related kinase (trk) inhibitors |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| EP3558298A4 (en) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | ANTIDIABETIC SPIROCHROMAN COMPOUNDS |
| KR20200121823A (ko) * | 2018-02-16 | 2020-10-26 | 유씨비 바이오파마 에스알엘 | 약학적 6,5 헤테로비시클릭 고리 유도체 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2140416C1 (ru) * | 1994-05-10 | 1999-10-27 | Хехст АГ | Производные циклогексанкарбоновой кислоты, смесь их изомеров или отдельные изомеры и физиологически переносимые соли, фармацевтическая композиция |
| RU2158261C2 (ru) * | 1995-02-01 | 2000-10-27 | Байер Аг | Производные амида фенилциклогексилкарбоновой кислоты, смесь их изомеров или отдельные изомеры и их соли, фармацевтическая композиция с антиартериосклеротической и антирестенозной активностью |
| US6350760B1 (en) * | 1999-06-04 | 2002-02-26 | Merck & Co., Inc. | Substituted piperidines as melanocortin-4 receptor agonists |
| RU2201929C2 (ru) * | 1997-07-03 | 2003-04-10 | Дюпон Фармасьютикалз Компани | Имидазопиримидины и имидазопиридины, фармацевтическая композиция на их основе, способ лечения неврологических нарушений |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003528810A (ja) * | 1999-08-04 | 2003-09-30 | ミレニアム ファーマスーティカルズ インク | メラノコルチン−４受容体結合化合物及びその使用方法 |
| AU2001236919A1 (en) | 2000-02-09 | 2001-08-20 | The Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | Premeiotic and postmeiotic origin of teratomas: isolated teratoma stem cells for therapeutic uses |
| JP2003534377A (ja) * | 2000-05-30 | 2003-11-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作働薬 |
| IL156031A0 (en) * | 2000-12-15 | 2003-12-23 | Vertex Pharma | Fused heterocyclic derivatives and pharmaceutical compositions containing the same |
| EP1465888A2 (en) * | 2002-01-10 | 2004-10-13 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
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2003
- 2003-03-31 FR FR0303924A patent/FR2852957B1/fr not_active Expired - Fee Related
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2004
- 2004-03-29 NZ NZ542763A patent/NZ542763A/en not_active IP Right Cessation
- 2004-03-29 WO PCT/FR2004/000785 patent/WO2004089951A1/fr not_active Ceased
- 2004-03-29 RU RU2005133441/04A patent/RU2358974C2/ru not_active IP Right Cessation
- 2004-03-29 KR KR1020057018420A patent/KR101102742B1/ko not_active Expired - Fee Related
- 2004-03-29 MX MXPA05010278A patent/MXPA05010278A/es active IP Right Grant
- 2004-03-29 DE DE602004021247T patent/DE602004021247D1/de not_active Expired - Lifetime
- 2004-03-29 ES ES04742386T patent/ES2327929T3/es not_active Expired - Lifetime
- 2004-03-29 BR BRPI0408817-4A patent/BRPI0408817A/pt not_active IP Right Cessation
- 2004-03-29 EP EP04742386A patent/EP1615925B1/fr not_active Expired - Lifetime
- 2004-03-29 AU AU2004228416A patent/AU2004228416B9/en not_active Ceased
- 2004-03-29 CA CA2520855A patent/CA2520855C/fr not_active Expired - Fee Related
- 2004-03-29 CN CNB2004800084919A patent/CN100455581C/zh not_active Expired - Fee Related
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2140416C1 (ru) * | 1994-05-10 | 1999-10-27 | Хехст АГ | Производные циклогексанкарбоновой кислоты, смесь их изомеров или отдельные изомеры и физиологически переносимые соли, фармацевтическая композиция |
| RU2158261C2 (ru) * | 1995-02-01 | 2000-10-27 | Байер Аг | Производные амида фенилциклогексилкарбоновой кислоты, смесь их изомеров или отдельные изомеры и их соли, фармацевтическая композиция с антиартериосклеротической и антирестенозной активностью |
| RU2201929C2 (ru) * | 1997-07-03 | 2003-04-10 | Дюпон Фармасьютикалз Компани | Имидазопиримидины и имидазопиридины, фармацевтическая композиция на их основе, способ лечения неврологических нарушений |
| US6350760B1 (en) * | 1999-06-04 | 2002-02-26 | Merck & Co., Inc. | Substituted piperidines as melanocortin-4 receptor agonists |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ542763A (en) | 2007-11-30 |
| CA2520855A1 (fr) | 2004-10-21 |
| EP1615925B1 (fr) | 2009-05-27 |
| US20060173036A1 (en) | 2006-08-03 |
| CN1768058A (zh) | 2006-05-03 |
| AU2004228416B2 (en) | 2010-02-11 |
| CN100455581C (zh) | 2009-01-28 |
| JP4711948B2 (ja) | 2011-06-29 |
| AU2004228416B8 (en) | 2010-03-04 |
| CA2520855C (fr) | 2014-05-13 |
| US7495009B2 (en) | 2009-02-24 |
| HK1090640A1 (zh) | 2006-12-29 |
| KR101102742B1 (ko) | 2012-01-05 |
| FR2852957B1 (fr) | 2005-06-10 |
| JP2006522076A (ja) | 2006-09-28 |
| ATE432280T1 (de) | 2009-06-15 |
| AU2004228416B9 (en) | 2010-03-11 |
| AU2004228416A1 (en) | 2004-10-21 |
| WO2004089951A1 (fr) | 2004-10-21 |
| MXPA05010278A (es) | 2005-11-17 |
| IL170834A (en) | 2010-12-30 |
| BRPI0408817A (pt) | 2006-04-04 |
| ES2327929T3 (es) | 2009-11-05 |
| DE602004021247D1 (de) | 2009-07-09 |
| RU2005133441A (ru) | 2006-05-10 |
| WO2004089951A8 (fr) | 2006-01-12 |
| KR20060002893A (ko) | 2006-01-09 |
| EP1615925A1 (fr) | 2006-01-18 |
| FR2852957A1 (fr) | 2004-10-01 |
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