AU2007257922A1 - Novel MCH receptor antagonists - Google Patents
Novel MCH receptor antagonists Download PDFInfo
- Publication number
- AU2007257922A1 AU2007257922A1 AU2007257922A AU2007257922A AU2007257922A1 AU 2007257922 A1 AU2007257922 A1 AU 2007257922A1 AU 2007257922 A AU2007257922 A AU 2007257922A AU 2007257922 A AU2007257922 A AU 2007257922A AU 2007257922 A1 AU2007257922 A1 AU 2007257922A1
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- methoxy
- chloro
- thieno
- pyridin
- 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
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 2
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 244
- 239000000203 mixture Substances 0.000 claims description 149
- -1 -OR 6 Chemical group 0.000 claims description 89
- 239000001257 hydrogen Substances 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 83
- 125000000623 heterocyclic group Chemical group 0.000 claims description 68
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 49
- 125000001153 fluoro group Chemical group F* 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 150000002431 hydrogen Chemical class 0.000 claims description 42
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 32
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 208000008589 Obesity Diseases 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 235000020824 obesity Nutrition 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 125000004193 piperazinyl group Chemical group 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000002393 azetidinyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 229910052701 rubidium Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000005959 diazepanyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- CZRGFNLUHBYQMI-DENIHFKCSA-N 2-(4-chlorophenyl)-6-[4-[(3r,4r)-4-hydroxy-1-methylpyrrolidin-3-yl]oxy-3-methoxyphenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1O[C@@H]1CN(C)C[C@H]1O CZRGFNLUHBYQMI-DENIHFKCSA-N 0.000 claims description 5
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- DANNXIYTSPUKNZ-HXUWFJFHSA-N 2-(4-chlorophenyl)-6-[3-methoxy-4-[(3r)-piperidin-3-yl]oxyphenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1O[C@@H]1CCCNC1 DANNXIYTSPUKNZ-HXUWFJFHSA-N 0.000 claims description 4
- RIYCFWXOWRQFFK-UHFFFAOYSA-N 6h-thieno[2,3-c]pyridin-7-one Chemical compound O=C1NC=CC2=C1SC=C2 RIYCFWXOWRQFFK-UHFFFAOYSA-N 0.000 claims description 4
- NRPHIGGEADJUSS-LJQANCHMSA-N 2-(4-chlorophenyl)-6-[4-[(3r)-3-hydroxypyrrolidin-1-yl]-3-methoxyphenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CC[C@@H](O)C1 NRPHIGGEADJUSS-LJQANCHMSA-N 0.000 claims description 3
- 239000002830 appetite depressant Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- GVZOAZDOGPCEIG-UHFFFAOYSA-N n-[4-[2-(4-chlorophenyl)-7-oxothieno[2,3-c]pyridin-6-yl]-2-methoxyphenyl]-2-pyrrolidin-1-ylacetamide Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1NC(=O)CN1CCCC1 GVZOAZDOGPCEIG-UHFFFAOYSA-N 0.000 claims description 3
- NGSRPWCECXHPGY-NRFANRHFSA-N 2-(4-chlorophenyl)-6-[4-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]-3-methoxyphenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CC[C@H](N(C)C)C1 NGSRPWCECXHPGY-NRFANRHFSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- ACVJLNZNERVECQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(3-fluoro-4-piperazin-1-ylphenyl)thieno[2,3-c]pyridin-7-one Chemical compound FC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CCNCC1 ACVJLNZNERVECQ-UHFFFAOYSA-N 0.000 claims 1
- PKLDHRJOXRBRNR-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[3-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydrothieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CCN(C)CC1 PKLDHRJOXRBRNR-UHFFFAOYSA-N 0.000 claims 1
- BYWIKAYNGOZCQR-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-[3-methoxy-4-[(3-methylimidazol-4-yl)methoxy]phenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OCC1=CN=CN1C BYWIKAYNGOZCQR-UHFFFAOYSA-N 0.000 claims 1
- AGDPDWYQZACUSZ-NRFANRHFSA-N 2-(4-chlorophenyl)-6-[3-methoxy-4-[(3s)-1-methylpiperidin-3-yl]oxyphenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1O[C@H]1CCCN(C)C1 AGDPDWYQZACUSZ-NRFANRHFSA-N 0.000 claims 1
- QXSOSEXLDZKZSG-IBGZPJMESA-N 2-(4-chlorophenyl)-6-[3-methoxy-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]phenyl]thieno[2,3-c]pyridin-7-one Chemical compound C1[C@@H](NC)CCN1C1=CC=C(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)C=C1OC QXSOSEXLDZKZSG-IBGZPJMESA-N 0.000 claims 1
- DANNXIYTSPUKNZ-FQEVSTJZSA-N 2-(4-chlorophenyl)-6-[3-methoxy-4-[(3s)-piperidin-3-yl]oxyphenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1O[C@H]1CCCNC1 DANNXIYTSPUKNZ-FQEVSTJZSA-N 0.000 claims 1
- NGSRPWCECXHPGY-OAQYLSRUSA-N 2-(4-chlorophenyl)-6-[4-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]-3-methoxyphenyl]thieno[2,3-c]pyridin-7-one Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CC[C@@H](N(C)C)C1 NGSRPWCECXHPGY-OAQYLSRUSA-N 0.000 claims 1
- XCEICWWFGPUZHI-UHFFFAOYSA-N 6-(4-aminophenyl)-2-(4-chlorophenyl)thieno[2,3-c]pyridin-7-one Chemical compound C1=CC(N)=CC=C1N1C(=O)C(SC(=C2)C=3C=CC(Cl)=CC=3)=C2C=C1 XCEICWWFGPUZHI-UHFFFAOYSA-N 0.000 claims 1
- LCIHRXSOFXUFGE-UHFFFAOYSA-N n-[4-[2-(4-chlorophenyl)-7-oxo-4,5-dihydrothieno[2,3-c]pyridin-6-yl]-2-methoxyphenyl]-2-pyrrolidin-1-ylacetamide Chemical compound COC1=CC(N2C(C=3SC(=CC=3CC2)C=2C=CC(Cl)=CC=2)=O)=CC=C1NC(=O)CN1CCCC1 LCIHRXSOFXUFGE-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 229
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 153
- 238000002360 preparation method Methods 0.000 description 126
- 238000003756 stirring Methods 0.000 description 126
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 124
- 239000012141 concentrate Substances 0.000 description 120
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- 238000006243 chemical reaction Methods 0.000 description 86
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- 239000011734 sodium Substances 0.000 description 79
- 239000000284 extract Substances 0.000 description 70
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
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- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RHFDLMVXCXVPBB-CYBMUJFWSA-N tert-butyl (3r)-3-(2-methoxy-4-nitrophenoxy)piperidine-1-carboxylate Chemical compound COC1=CC([N+]([O-])=O)=CC=C1O[C@H]1CN(C(=O)OC(C)(C)C)CCC1 RHFDLMVXCXVPBB-CYBMUJFWSA-N 0.000 description 1
- UIJXHKXIOCDSEB-MRVPVSSYSA-N tert-butyl (3r)-3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H](O)C1 UIJXHKXIOCDSEB-MRVPVSSYSA-N 0.000 description 1
- JLWKZCMTAAEEHO-LBPRGKRZSA-N tert-butyl (3s)-3-(4-amino-2-methoxyphenoxy)pyrrolidine-1-carboxylate Chemical compound COC1=CC(N)=CC=C1O[C@@H]1CN(C(=O)OC(C)(C)C)CC1 JLWKZCMTAAEEHO-LBPRGKRZSA-N 0.000 description 1
- NUYWPLSBEHXOHO-UHFFFAOYSA-N tert-butyl 2-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1O NUYWPLSBEHXOHO-UHFFFAOYSA-N 0.000 description 1
- GEGYXNNTJRXWKF-UHFFFAOYSA-N tert-butyl 3-(2-methoxy-4-nitrophenoxy)azetidine-1-carboxylate Chemical compound COC1=CC([N+]([O-])=O)=CC=C1OC1CN(C(=O)OC(C)(C)C)C1 GEGYXNNTJRXWKF-UHFFFAOYSA-N 0.000 description 1
- AWPBKPMUHXEWRV-UHFFFAOYSA-N tert-butyl 3-(4-amino-2-fluorophenoxy)azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1OC1=CC=C(N)C=C1F AWPBKPMUHXEWRV-UHFFFAOYSA-N 0.000 description 1
- CYWSZTNZWXEFHG-UHFFFAOYSA-N tert-butyl 3-(4-amino-2-methoxyphenoxy)azetidine-1-carboxylate Chemical compound COC1=CC(N)=CC=C1OC1CN(C(=O)OC(C)(C)C)C1 CYWSZTNZWXEFHG-UHFFFAOYSA-N 0.000 description 1
- OHOAOVRBMXIHLS-UHFFFAOYSA-N tert-butyl 3-(4-bromobenzoyl)azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1C(=O)C1=CC=C(Br)C=C1 OHOAOVRBMXIHLS-UHFFFAOYSA-N 0.000 description 1
- CDFYNOOXQDBKKV-UHFFFAOYSA-N tert-butyl 3-(4-bromobenzoyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C(=O)C1=CC=C(Br)C=C1 CDFYNOOXQDBKKV-UHFFFAOYSA-N 0.000 description 1
- NBSUQHNPRXCCEP-UHFFFAOYSA-N tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1OC1=CC=C(Br)C=C1 NBSUQHNPRXCCEP-UHFFFAOYSA-N 0.000 description 1
- MQJRWDPLYITQQC-UHFFFAOYSA-N tert-butyl 3-[4-[2-(4-chlorophenyl)-7-oxothieno[2,3-c]pyridin-6-yl]-2-methoxyphenoxy]-4-hydroxypyrrolidine-1-carboxylate Chemical compound COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1OC1CN(C(=O)OC(C)(C)C)CC1O MQJRWDPLYITQQC-UHFFFAOYSA-N 0.000 description 1
- OXFWAVQYUXISNK-UHFFFAOYSA-N tert-butyl 3-[4-[[5-(4-chlorophenyl)-3-(2-trimethylsilylethynyl)thiophene-2-carbonyl]amino]-2-methoxyphenoxy]azetidine-1-carboxylate Chemical compound C=1C=C(OC2CN(C2)C(=O)OC(C)(C)C)C(OC)=CC=1NC(=O)C(=C(C=1)C#C[Si](C)(C)C)SC=1C1=CC=C(Cl)C=C1 OXFWAVQYUXISNK-UHFFFAOYSA-N 0.000 description 1
- SZHVHYKDWGKZSO-UHFFFAOYSA-N tert-butyl 3-[[4-[2-(4-chlorophenyl)-7-oxothieno[2,3-c]pyridin-6-yl]phenyl]carbamoyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C(=O)NC1=CC=C(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)C=C1 SZHVHYKDWGKZSO-UHFFFAOYSA-N 0.000 description 1
- NHDGOVOBEZPXMY-UHFFFAOYSA-N tert-butyl 3-carbamoylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C(N)=O)C1 NHDGOVOBEZPXMY-UHFFFAOYSA-N 0.000 description 1
- XRRXRQJQQKMFBC-UHFFFAOYSA-N tert-butyl 3-hydroxyazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC(O)C1 XRRXRQJQQKMFBC-UHFFFAOYSA-N 0.000 description 1
- YOLVWCABLVHASL-UHFFFAOYSA-N tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C([N+]([O-])=O)C=C1F YOLVWCABLVHASL-UHFFFAOYSA-N 0.000 description 1
- NXZIGGBPLGAPTI-UHFFFAOYSA-N tert-butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC2OC21 NXZIGGBPLGAPTI-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- RSHWAIKUWOCZHD-UHFFFAOYSA-N thieno[2,3-c]pyran-7-one Chemical compound O=C1OC=CC2=C1SC=C2 RSHWAIKUWOCZHD-UHFFFAOYSA-N 0.000 description 1
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81184106P | 2006-06-08 | 2006-06-08 | |
| US60/811,841 | 2006-06-08 | ||
| PCT/US2007/070662 WO2007146758A2 (en) | 2006-06-08 | 2007-06-08 | Novel mch receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2007257922A1 true AU2007257922A1 (en) | 2007-12-21 |
Family
ID=38651254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007257922A Abandoned AU2007257922A1 (en) | 2006-06-08 | 2007-06-08 | Novel MCH receptor antagonists |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8263772B2 (https=) |
| EP (1) | EP2029609A2 (https=) |
| JP (1) | JP5198439B2 (https=) |
| CN (1) | CN101454328A (https=) |
| AU (1) | AU2007257922A1 (https=) |
| BR (1) | BRPI0712680A2 (https=) |
| CA (1) | CA2652385A1 (https=) |
| EA (1) | EA015127B1 (https=) |
| MX (1) | MX2008015662A (https=) |
| WO (1) | WO2007146758A2 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2740193A1 (en) | 2008-12-23 | 2010-07-01 | Abbott Laboratories | Anti-viral compounds |
| EP2367823A1 (en) | 2008-12-23 | 2011-09-28 | Abbott Laboratories | Anti-viral compounds |
| BRPI0923527A2 (pt) * | 2008-12-24 | 2016-08-09 | Syngenta Ltd | métodos de preparo de fungicidas |
| CN102459165B (zh) * | 2009-04-15 | 2015-09-02 | Abbvie公司 | 抗病毒化合物 |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| UA118080C2 (uk) | 2009-06-11 | 2018-11-26 | Еббві Айрленд Анлімітед Компані | Противірусні сполуки |
| US8716454B2 (en) | 2009-06-11 | 2014-05-06 | Abbvie Inc. | Solid compositions |
| NZ605440A (en) | 2010-06-10 | 2014-05-30 | Abbvie Bahamas Ltd | Solid compositions comprising an hcv inhibitor |
| US10201584B1 (en) | 2011-05-17 | 2019-02-12 | Abbvie Inc. | Compositions and methods for treating HCV |
| US9034832B2 (en) | 2011-12-29 | 2015-05-19 | Abbvie Inc. | Solid compositions |
| US20150065343A1 (en) | 2012-04-02 | 2015-03-05 | Basf Se | Acrylamide compounds for combating invertebrate pests |
| BR112014027133A2 (pt) | 2012-05-09 | 2017-06-27 | Basf Se | compostos, composição agrícola ou veterinária, método para o controle das pragas de invertebrados, material de propagação dos vegetais e método para o tratamento ou proteção de um animal. |
| MX394360B (es) | 2013-03-14 | 2025-03-24 | Sumitomo Pharma Oncology Inc | Inhibidores de jak2 y alk2 y metodos para su uso. |
| US11484534B2 (en) | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
| EP3089757A1 (en) | 2014-01-03 | 2016-11-09 | AbbVie Inc. | Solid antiviral dosage forms |
| AR102849A1 (es) * | 2015-03-09 | 2017-03-29 | Astellas Pharma Inc | Compuesto de piridina bicíclica |
| ES2849951T3 (es) | 2015-06-18 | 2021-08-24 | 89Bio Ltd | Derivados de piperidina 4-bencil y 4-benzoil sustituidos |
| EA201890086A1 (ru) | 2015-06-18 | 2018-06-29 | Сефалон, Инк. | 1,4-замещенные производные пиперидина |
| MX2021000977A (es) | 2018-07-26 | 2021-04-12 | Sumitomo Pharma Oncology Inc | Metodos para tratar enfermedades asociadas con expresion anormal de receptor de activina a tipo 1 (acvr1) e inhibidores de acvr1 para uso en los mismos. |
| CN113226322A (zh) | 2018-10-30 | 2021-08-06 | 诺维逊生物股份有限公司 | 作为bet抑制剂的杂环化合物 |
| EP3997070A4 (en) | 2019-07-02 | 2023-07-26 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AS BET INHIBITORS |
| US20260028336A1 (en) * | 2022-07-20 | 2026-01-29 | Arcus Biosciences, Inc. | Cbl-b inhibitors and methods of use thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2002003370A (ja) * | 1999-09-20 | 2002-01-09 | Takeda Chem Ind Ltd | メラニン凝集ホルモン拮抗剤 |
| US20020099073A1 (en) * | 2000-07-07 | 2002-07-25 | Andersen Henrik Sune | Modulators of protein tyrosine phosphatases (PTPases) |
| GB0124627D0 (en) * | 2001-10-15 | 2001-12-05 | Smithkline Beecham Plc | Novel compounds |
| US20060194871A1 (en) * | 2003-04-11 | 2006-08-31 | Barvian Kevin K | Heterocyclic mchr1 antagoists |
| US20070078125A1 (en) * | 2003-10-23 | 2007-04-05 | Glaxo Group Limited | Arylamine mch r1 antagonists |
| WO2005047293A1 (en) * | 2003-11-07 | 2005-05-26 | Neurocrine Biosciences, Inc. | Melanin-concentrating hormone receptor antagonists and compositions and methods related thereto |
| UA83416C2 (en) * | 2004-02-13 | 2008-07-10 | Баниу Фармасьютикал Ко., Лтд. | Fused ring 4-oxopyrimidine derivative |
| US20050256124A1 (en) * | 2004-04-15 | 2005-11-17 | Neurocrine Biosciences, Inc. | Melanin-concentrating hormone receptor antagonists and compositions and methods related thereto |
| MXPA06014535A (es) | 2004-06-18 | 2007-06-05 | Biolipox Ab | Indoles utiles en el tratamiento de la inflamacion. |
| US7902356B2 (en) * | 2004-12-17 | 2011-03-08 | Eli Lilly And Company | Thiazolopyridinone derivates as MCH receptor antagonists |
| EP1987020B1 (en) * | 2006-02-15 | 2012-10-03 | Sanofi | Azacyclyl-substituted aryldihydroisoquinolinones, process for their preparation and their use as medicaments |
| KR20080094699A (ko) * | 2006-02-15 | 2008-10-23 | 사노피-아벤티스 | 신규 아미노알콜-치환된 아릴디하이드로이소퀴놀리논, 이의제조 방법 및 이의 약물로서의 용도 |
-
2007
- 2007-06-08 MX MX2008015662A patent/MX2008015662A/es unknown
- 2007-06-08 WO PCT/US2007/070662 patent/WO2007146758A2/en not_active Ceased
- 2007-06-08 EA EA200870517A patent/EA015127B1/ru not_active IP Right Cessation
- 2007-06-08 EP EP07798258A patent/EP2029609A2/en not_active Withdrawn
- 2007-06-08 CN CNA2007800195489A patent/CN101454328A/zh active Pending
- 2007-06-08 CA CA002652385A patent/CA2652385A1/en not_active Abandoned
- 2007-06-08 AU AU2007257922A patent/AU2007257922A1/en not_active Abandoned
- 2007-06-08 JP JP2009514544A patent/JP5198439B2/ja not_active Expired - Fee Related
- 2007-06-08 US US12/298,792 patent/US8263772B2/en not_active Expired - Fee Related
- 2007-06-08 BR BRPI0712680-8A patent/BRPI0712680A2/pt not_active IP Right Cessation
-
2012
- 2012-08-08 US US13/569,899 patent/US20120302547A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20090093456A1 (en) | 2009-04-09 |
| JP5198439B2 (ja) | 2013-05-15 |
| BRPI0712680A2 (pt) | 2012-11-20 |
| EP2029609A2 (en) | 2009-03-04 |
| WO2007146758A3 (en) | 2008-02-07 |
| EA200870517A1 (ru) | 2009-04-28 |
| WO2007146758A2 (en) | 2007-12-21 |
| CA2652385A1 (en) | 2007-12-21 |
| US8263772B2 (en) | 2012-09-11 |
| EA015127B1 (ru) | 2011-06-30 |
| JP2009539875A (ja) | 2009-11-19 |
| MX2008015662A (es) | 2009-01-12 |
| CN101454328A (zh) | 2009-06-10 |
| US20120302547A1 (en) | 2012-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |