CA2533112A1 - Melanin concentrating hormone receptor antagonist - Google Patents
Melanin concentrating hormone receptor antagonist Download PDFInfo
- Publication number
- CA2533112A1 CA2533112A1 CA002533112A CA2533112A CA2533112A1 CA 2533112 A1 CA2533112 A1 CA 2533112A1 CA 002533112 A CA002533112 A CA 002533112A CA 2533112 A CA2533112 A CA 2533112A CA 2533112 A1 CA2533112 A1 CA 2533112A1
- Authority
- CA
- Canada
- Prior art keywords
- och3
- group
- methyl
- tetrazol
- phenylallyl
- 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.)
- Abandoned
Links
- 229940122023 Melanin concentrating hormone receptor antagonist Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 32
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims abstract description 31
- ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000651 prodrug Substances 0.000 claims abstract description 30
- 229940002612 prodrug Drugs 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 230000002265 prevention Effects 0.000 claims abstract description 6
- 230000001404 mediated effect Effects 0.000 claims abstract description 5
- 102000047659 melanin-concentrating hormone Human genes 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 1456
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 759
- -1 heterocyclo Chemical group 0.000 claims description 704
- 125000000217 alkyl group Chemical group 0.000 claims description 187
- 125000003118 aryl group Chemical group 0.000 claims description 131
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 109
- 229910052739 hydrogen Inorganic materials 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 99
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 98
- 125000001424 substituent group Chemical group 0.000 claims description 86
- 125000005843 halogen group Chemical group 0.000 claims description 84
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 83
- 125000001072 heteroaryl group Chemical group 0.000 claims description 78
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 62
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 53
- 125000001041 indolyl group Chemical class 0.000 claims description 53
- 229930194542 Keto Chemical group 0.000 claims description 52
- 125000004429 atom Chemical group 0.000 claims description 52
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 52
- 125000000468 ketone group Chemical group 0.000 claims description 52
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 52
- 125000004104 aryloxy group Chemical group 0.000 claims description 50
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 49
- 239000004305 biphenyl Substances 0.000 claims description 49
- 235000010290 biphenyl Nutrition 0.000 claims description 49
- 125000001624 naphthyl group Chemical group 0.000 claims description 49
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 46
- 125000001544 thienyl group Chemical group 0.000 claims description 46
- 125000002757 morpholinyl group Chemical group 0.000 claims description 43
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 43
- 125000002883 imidazolyl group Chemical group 0.000 claims description 42
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 42
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 42
- 125000002971 oxazolyl group Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 42
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 42
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 42
- 125000000335 thiazolyl group Chemical group 0.000 claims description 42
- 125000001425 triazolyl group Chemical group 0.000 claims description 42
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims description 41
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 41
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 41
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 40
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 37
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 37
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 36
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 36
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 36
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 36
- 125000004193 piperazinyl group Chemical group 0.000 claims description 36
- 125000003386 piperidinyl group Chemical group 0.000 claims description 36
- 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 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 32
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 27
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 25
- 125000001188 haloalkyl group Chemical group 0.000 claims description 25
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 24
- 125000002541 furyl group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 22
- 125000006492 halo alkyl aryl group Chemical group 0.000 claims description 22
- 125000004996 haloaryloxy group Chemical group 0.000 claims description 22
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 19
- 208000008589 Obesity Diseases 0.000 claims description 18
- 235000020824 obesity Nutrition 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 17
- 125000003435 aroyl group Chemical group 0.000 claims description 16
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims description 15
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 14
- 125000003106 haloaryl group Chemical group 0.000 claims description 14
- 125000005936 piperidyl group Chemical group 0.000 claims description 14
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 14
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 13
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 claims description 13
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 claims description 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
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- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002671 adjuvant Substances 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 8
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 7
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 7
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- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 7
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 6
- DEVWEFBXXYMHIL-UHFFFAOYSA-N CCCOP(O)=O Chemical group CCCOP(O)=O DEVWEFBXXYMHIL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004799 bromophenyl group Chemical group 0.000 claims description 6
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 6
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 6
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical group CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004212 difluorophenyl group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical group CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 claims description 6
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- XAKRTGZVYPZHCO-UHFFFAOYSA-O hydroxy-methoxy-oxophosphanium Chemical group CO[P+](O)=O XAKRTGZVYPZHCO-UHFFFAOYSA-O 0.000 claims description 6
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 6
- CHJUOCDSZWMLRU-UHFFFAOYSA-N oxo(dipropoxy)phosphanium Chemical group CCCO[P+](=O)OCCC CHJUOCDSZWMLRU-UHFFFAOYSA-N 0.000 claims description 6
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- RJWOYPDXOULOGD-UHFFFAOYSA-N 4,5-dichloro-2-phenoxy-1H-imidazole Chemical group ClC1=C(N=C(N1)OC1=CC=CC=C1)Cl RJWOYPDXOULOGD-UHFFFAOYSA-N 0.000 claims description 4
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
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- KNTSGQILUQZVMS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)-4-[[1-(2,6-dimethylphenyl)tetrazol-5-yl]-[3-(trifluoromethyl)phenyl]methyl]piperazine Chemical compound CC1=CC=CC(C)=C1N1C(C(N2CCN(CC=3C=C4OCOC4=CC=3)CC2)C=2C=C(C=CC=2)C(F)(F)F)=NN=N1 KNTSGQILUQZVMS-UHFFFAOYSA-N 0.000 claims description 2
- SECHGYBJGVHMSP-UHFFFAOYSA-N 1-[[1-(2,6-dimethylphenyl)tetrazol-5-yl]-[3-(trifluoromethyl)phenyl]methyl]-4-(3-phenylpropyl)piperazine Chemical compound CC1=CC=CC(C)=C1N1C(C(N2CCN(CCCC=3C=CC=CC=3)CC2)C=2C=C(C=CC=2)C(F)(F)F)=NN=N1 SECHGYBJGVHMSP-UHFFFAOYSA-N 0.000 claims description 2
- HKLCZAQNBCNUSK-UHFFFAOYSA-N 1-benzyl-n-[[1-(2,6-dimethylphenyl)tetrazol-5-yl]-[3-(trifluoromethyl)phenyl]methyl]-n-ethylpyrrolidin-3-amine Chemical compound C1CN(CC=2C=CC=CC=2)CC1N(CC)C(C=1C=C(C=CC=1)C(F)(F)F)C1=NN=NN1C1=C(C)C=CC=C1C HKLCZAQNBCNUSK-UHFFFAOYSA-N 0.000 claims description 2
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
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| KR20080058436A (ko) | 2005-10-13 | 2008-06-25 | 와이어쓰 | 글루탐산 유도체의 제조 방법 |
| US20090018142A9 (en) * | 2006-05-02 | 2009-01-15 | Zhengping Zhuang | Use of phosphatases to treat tumors overexpressing N-CoR |
| US8604031B2 (en) | 2006-05-18 | 2013-12-10 | Mannkind Corporation | Intracellular kinase inhibitors |
| TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與５-ｈｔ2ａ血清素受體相關聯病症之作為５-ｈｔ2ａ血清素受體之調節劑的吡唑衍生物 |
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| BRPI0806365B8 (pt) * | 2007-02-06 | 2021-05-25 | Lixte Biotechnology Holdings Inc | composto, uso do composto, composição farmacêutica e uso da composição farmacêutica |
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| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
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| US8673920B2 (en) * | 2009-05-06 | 2014-03-18 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2632465B1 (en) | 2010-10-27 | 2015-12-30 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2012058134A1 (en) | 2010-10-29 | 2012-05-03 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| GB201106817D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compound |
| ES2605164T3 (es) | 2011-08-19 | 2017-03-13 | Merck Sharp & Dohme Corp. | Inhibidores del canal de potasio de la médula renal externa |
| WO2013039802A1 (en) | 2011-09-16 | 2013-03-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2771004B1 (en) | 2011-10-25 | 2016-05-18 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2771005B1 (en) | 2011-10-25 | 2016-05-18 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
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| US9108947B2 (en) | 2011-10-31 | 2015-08-18 | Merck Sharp & Dohme Corp. | Inhibitors of the Renal Outer Medullary Potassium channel |
| EP2773199B1 (en) | 2011-10-31 | 2019-04-10 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9206199B2 (en) | 2011-12-16 | 2015-12-08 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
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| HUP0302582A2 (hu) * | 2000-12-22 | 2003-12-29 | Schering Corp. | Piperidin MCH antagonisták, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk elhízás kezelésére |
| DE10123958A1 (de) * | 2001-05-17 | 2002-11-28 | Aventis Pharma Gmbh | Verfahren zur Identifizierung von Liganden für G protein coupled receptors |
| BR0209932A (pt) | 2001-05-22 | 2004-10-13 | Neurogen Corp | Composto ou sal farmaceuticamente aceitável do mesmo, composição farmacêutica, preparação farmacêutica embalada, métodos para modular ligação de mch a um receptor de mch e de mvc, para alterar a atividade de transdução de sinal de um receptor de mch em uma célula, para tratar uma doença ou distúrbio associado com a ativação de receptor de mch patogênico obesidade e para determinar a presença ou ausência de receptor de mch em uma amostra, e, uso de um composto |
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| DE10139416A1 (de) | 2001-08-17 | 2003-03-06 | Aventis Pharma Gmbh | Aminoalkyl substituierte aromatische Bicyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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| US20040180889A1 (en) * | 2002-03-01 | 2004-09-16 | Pintex Pharmaceuticals, Inc. | Pin1-modulating compounds and methods of use thereof |
| WO2003087046A1 (en) | 2002-04-09 | 2003-10-23 | 7Tm Pharma A/S | Novel aminotetraline compounds for use in mch receptor related disorders |
| WO2003087044A2 (en) | 2002-04-09 | 2003-10-23 | 7Tm Pharma A/S | Novel carboxamide compounds for use in mch receptor related disorders |
| US7078430B2 (en) * | 2002-07-08 | 2006-07-18 | Ranbaxy Laboratories Limited | HMG CoA-reductase inhibitors |
| FR2842524B1 (fr) * | 2002-07-16 | 2005-04-22 | Aventis Pharma Sa | Compositions pharmaceutiques contenant un derive de 3-guanidinocarbonyl-1-heteroaryl-pyrrole, leur procede de preparation a titre de medicaments |
| US7091235B2 (en) * | 2002-10-15 | 2006-08-15 | Signal Pharmaceuticals, Llc | Benzopyranone compounds, compositions thereof, and methods for treating or preventing cancer |
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2004
- 2004-08-11 US US10/916,011 patent/US7514438B2/en not_active Expired - Fee Related
- 2004-08-11 CA CA002533112A patent/CA2533112A1/en not_active Abandoned
- 2004-08-11 AU AU2004266233A patent/AU2004266233A1/en not_active Abandoned
- 2004-08-11 JP JP2006523335A patent/JP2007502287A/ja not_active Withdrawn
- 2004-08-11 EP EP04780799A patent/EP1653960A4/en not_active Withdrawn
- 2004-08-11 MX MXPA06001636A patent/MXPA06001636A/es unknown
- 2004-08-11 WO PCT/US2004/026021 patent/WO2005019167A2/en not_active Ceased
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2009
- 2009-02-06 US US12/367,083 patent/US7659276B2/en not_active Expired - Fee Related
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| US7659276B2 (en) | 2010-02-09 |
| EP1653960A2 (en) | 2006-05-10 |
| WO2005019167A2 (en) | 2005-03-03 |
| US20050215526A1 (en) | 2005-09-29 |
| JP2007502287A (ja) | 2007-02-08 |
| WO2005019167A3 (en) | 2005-12-01 |
| US20090143405A1 (en) | 2009-06-04 |
| US7514438B2 (en) | 2009-04-07 |
| MXPA06001636A (es) | 2006-04-28 |
| EP1653960A4 (en) | 2008-11-26 |
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