MX2008015662A - Nuevos receptores antagonistas de la hormona concentradora de melanina (mch). - Google Patents
Nuevos receptores antagonistas de la hormona concentradora de melanina (mch).Info
- Publication number
- MX2008015662A MX2008015662A MX2008015662A MX2008015662A MX2008015662A MX 2008015662 A MX2008015662 A MX 2008015662A MX 2008015662 A MX2008015662 A MX 2008015662A MX 2008015662 A MX2008015662 A MX 2008015662A MX 2008015662 A MX2008015662 A MX 2008015662A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- methoxy
- chloro
- thieno
- pyridin
- Prior art date
Links
- 102000029828 Melanin-concentrating hormone receptor Human genes 0.000 title description 2
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 2
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 243
- 239000000203 mixture Substances 0.000 claims abstract description 149
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 208000008589 Obesity Diseases 0.000 claims abstract description 16
- 235000020824 obesity Nutrition 0.000 claims abstract description 16
- -1 -OR6 Chemical group 0.000 claims description 225
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 145
- 229910052757 nitrogen Inorganic materials 0.000 claims description 91
- 239000001257 hydrogen Substances 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 86
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 83
- 125000000623 heterocyclic group Chemical group 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 60
- 125000001153 fluoro group Chemical group F* 0.000 claims description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 40
- 150000002431 hydrogen Chemical group 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 33
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 31
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 27
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 14
- 125000004193 piperazinyl group Chemical group 0.000 claims description 14
- 229910052701 rubidium Inorganic materials 0.000 claims description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002393 azetidinyl group Chemical group 0.000 claims description 11
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 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 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000005959 diazepanyl group Chemical group 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- BZZWVAIHDUQQFR-UHFFFAOYSA-N COC1=C(C(C(N)=O)N2CCCC2)C=CC(N(CCC2=C3SC(C(C=C4)=CC=C4Cl)=C2)C3=O)=C1 Chemical compound COC1=C(C(C(N)=O)N2CCCC2)C=CC(N(CCC2=C3SC(C(C=C4)=CC=C4Cl)=C2)C3=O)=C1 BZZWVAIHDUQQFR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002830 appetite depressant Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 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
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 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
- QGZSTDQCFJYIOI-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-(3-fluoro-4-piperazin-1-ylphenyl)thieno[2,3-c]pyridin-7-one hydrochloride Chemical compound Cl.FC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1N1CCNCC1 QGZSTDQCFJYIOI-UHFFFAOYSA-N 0.000 claims 1
- JJKPBTAVSUKHIZ-ZMBIFBSDSA-N 2-(4-chlorophenyl)-6-[3-methoxy-4-[(3r)-1-methylpiperidin-3-yl]oxyphenyl]thieno[2,3-c]pyridin-7-one;hydrochloride Chemical compound Cl.COC1=CC(N2C(C=3SC(=CC=3C=C2)C=2C=CC(Cl)=CC=2)=O)=CC=C1O[C@@H]1CCCN(C)C1 JJKPBTAVSUKHIZ-ZMBIFBSDSA-N 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- LLMKLOUFMKLTIZ-UHFFFAOYSA-N 4h-thieno[2,3-c]pyridin-7-one Chemical compound O=C1N=CCC2=C1SC=C2 LLMKLOUFMKLTIZ-UHFFFAOYSA-N 0.000 claims 1
- YBBIWGPWUVGUFK-UHFFFAOYSA-N COC1=C(C=CC(=C1)N2C=CC3=C(C2=O)SC(=C3)C4=CC=C(C=C4)Cl)C(C(=O)N)N5CCCC5 Chemical compound COC1=C(C=CC(=C1)N2C=CC3=C(C2=O)SC(=C3)C4=CC=C(C=C4)Cl)C(C(=O)N)N5CCCC5 YBBIWGPWUVGUFK-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 13
- 101800002739 Melanin-concentrating hormone Proteins 0.000 abstract description 2
- 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 abstract description 2
- 102000047659 melanin-concentrating hormone Human genes 0.000 abstract description 2
- 239000003667 hormone antagonist Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 229
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 225
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 176
- 238000002360 preparation method Methods 0.000 description 127
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 124
- 238000006243 chemical reaction Methods 0.000 description 118
- 239000000243 solution Substances 0.000 description 115
- 235000019439 ethyl acetate Nutrition 0.000 description 103
- 229910001868 water Inorganic materials 0.000 description 95
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 80
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 49
- 239000007787 solid Substances 0.000 description 49
- 238000004587 chromatography analysis Methods 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000013058 crude material Substances 0.000 description 40
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- 239000012044 organic layer Substances 0.000 description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- 239000012267 brine Substances 0.000 description 29
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 29
- 235000011152 sodium sulphate Nutrition 0.000 description 29
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- 239000000725 suspension Substances 0.000 description 29
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 29
- 239000002904 solvent Substances 0.000 description 27
- 239000007832 Na2SO4 Substances 0.000 description 26
- 239000011734 sodium Substances 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
- 239000002253 acid Substances 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
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- 239000000463 material Substances 0.000 description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
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- 238000005481 NMR spectroscopy Methods 0.000 description 12
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- 239000000284 extract Substances 0.000 description 11
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
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- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 6
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 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
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 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
- ADPQWEGXWVSSKZ-UHFFFAOYSA-N pyrrolidine-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCN(C(O)=O)C1 ADPQWEGXWVSSKZ-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000001373 regressive effect Effects 0.000 description 1
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- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000007790 solid phase Substances 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
- 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
- NUYWPLSBEHXOHO-UHFFFAOYSA-N tert-butyl 2-hydroxypyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1O NUYWPLSBEHXOHO-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
- 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
- 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
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-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
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 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
- 238000004448 titration Methods 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
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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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81184106P | 2006-06-08 | 2006-06-08 | |
| PCT/US2007/070662 WO2007146758A2 (en) | 2006-06-08 | 2007-06-08 | Novel mch receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2008015662A true MX2008015662A (es) | 2009-01-12 |
Family
ID=38651254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2008015662A MX2008015662A (es) | 2006-06-08 | 2007-06-08 | Nuevos receptores antagonistas de la hormona concentradora de melanina (mch). |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US8263772B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2029609A2 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5198439B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN101454328A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2007257922A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BRPI0712680A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2652385A1 (cg-RX-API-DMAC7.html) |
| EA (1) | EA015127B1 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2008015662A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2007146758A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8546405B2 (en) | 2008-12-23 | 2013-10-01 | Abbott Laboratories | Anti-viral compounds |
| SG172352A1 (en) | 2008-12-23 | 2011-07-28 | Abbott Lab | Anti-viral compounds |
| US8637678B2 (en) | 2008-12-24 | 2014-01-28 | Syngenta Limited | Methods for the preparation of aryl amides |
| US9278922B2 (en) * | 2009-04-15 | 2016-03-08 | Abbvie Inc. | Anti-viral compounds |
| EA020031B1 (ru) * | 2009-06-11 | 2014-08-29 | Эббви Бахамаз Лтд. | Противовирусные соединения |
| US9394279B2 (en) | 2009-06-11 | 2016-07-19 | Abbvie Inc. | Anti-viral compounds |
| US8937150B2 (en) | 2009-06-11 | 2015-01-20 | Abbvie Inc. | Anti-viral compounds |
| 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 |
| WO2013149940A1 (en) | 2012-04-02 | 2013-10-10 | Basf Se | Acrylamide compounds for combating invertebrate pests |
| WO2013167633A1 (en) | 2012-05-09 | 2013-11-14 | Basf Se | Acrylamide compounds for combating invertebrate pests |
| US11484534B2 (en) | 2013-03-14 | 2022-11-01 | Abbvie Inc. | Methods for treating HCV |
| MX394360B (es) | 2013-03-14 | 2025-03-24 | Sumitomo Pharma Oncology Inc | Inhibidores de jak2 y alk2 y metodos para su uso. |
| WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
| AR102849A1 (es) * | 2015-03-09 | 2017-03-29 | Astellas Pharma Inc | Compuesto de piridina bicíclica |
| WO2016205590A1 (en) * | 2015-06-18 | 2016-12-22 | Cephalon, Inc. | Substituted 4-benzyl and 4-benzoyl piperidine derivatives |
| KR20180026459A (ko) | 2015-06-18 | 2018-03-12 | 세파론, 인코포레이티드 | 1,4-치환된 피페리딘 유도체 |
| AU2019310590A1 (en) | 2018-07-26 | 2021-01-14 | Sumitomo Pharma Oncology, Inc. | Methods for treating diseases associated with abnormal acvr1 expression and acvr1 inhibitors for use in the same |
| US11192900B2 (en) | 2018-10-30 | 2021-12-07 | Nuvation Bio Inc. | Substituted 1,6-dihydropyridinones and 1,2-dihydroisoquinolinones as bet inhibitors |
| KR102677015B1 (ko) | 2019-07-02 | 2024-06-19 | 누베이션 바이오 인크. | Bet 억제제로서의 헤테로시클릭 화합물 |
| EP4558501A1 (en) * | 2022-07-20 | 2025-05-28 | 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 |
| JP2007509158A (ja) * | 2003-10-23 | 2007-04-12 | グラクソ グループ リミテッド | 肥満、糖尿病、うつ病及び不安を治療するためのｍｃｈｒ１アンタゴニストとしての３−（４−アミノフェニル）チエノピリミド−４−オン誘導体 |
| US20050176738A1 (en) * | 2003-11-07 | 2005-08-11 | Neurocrine Biosciences, Inc. | Melanin-concentrating hormone receptor antagonists and compositions and methods related thereto |
| RU2358969C2 (ru) * | 2004-02-13 | 2009-06-20 | Баниу Фармасьютикал Ко., Лтд. | Конденсированное 4-оксопиримидиновое производное |
| WO2005103039A1 (en) * | 2004-04-15 | 2005-11-03 | Neurocrine Biosciences, Inc. | 2- (3-aminopyrrolidin-1-yl) pyridines as melanin-concentrating hormone receptor an tagonists |
| ES2315877T3 (es) | 2004-06-18 | 2009-04-01 | Biolipox Ab | Indoles utiles en el tratamiento de inflamaciones. |
| WO2006066174A1 (en) * | 2004-12-17 | 2006-06-22 | Eli Lilly And Company | Thiazolopyridinone derivates as mch receptor antagonists |
| WO2007093364A1 (en) * | 2006-02-15 | 2007-08-23 | Sanofi-Aventis | 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 EA EA200870517A patent/EA015127B1/ru not_active IP Right Cessation
- 2007-06-08 WO PCT/US2007/070662 patent/WO2007146758A2/en not_active Ceased
- 2007-06-08 AU AU2007257922A patent/AU2007257922A1/en not_active Abandoned
- 2007-06-08 CN CNA2007800195489A patent/CN101454328A/zh active Pending
- 2007-06-08 EP EP07798258A patent/EP2029609A2/en not_active Withdrawn
- 2007-06-08 JP JP2009514544A patent/JP5198439B2/ja not_active Expired - Fee Related
- 2007-06-08 CA CA002652385A patent/CA2652385A1/en not_active Abandoned
- 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
- 2007-06-08 MX MX2008015662A patent/MX2008015662A/es unknown
-
2012
- 2012-08-08 US US13/569,899 patent/US20120302547A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007146758A3 (en) | 2008-02-07 |
| CN101454328A (zh) | 2009-06-10 |
| US20090093456A1 (en) | 2009-04-09 |
| BRPI0712680A2 (pt) | 2012-11-20 |
| JP5198439B2 (ja) | 2013-05-15 |
| EA200870517A1 (ru) | 2009-04-28 |
| US8263772B2 (en) | 2012-09-11 |
| EA015127B1 (ru) | 2011-06-30 |
| JP2009539875A (ja) | 2009-11-19 |
| US20120302547A1 (en) | 2012-11-29 |
| AU2007257922A1 (en) | 2007-12-21 |
| EP2029609A2 (en) | 2009-03-04 |
| CA2652385A1 (en) | 2007-12-21 |
| WO2007146758A2 (en) | 2007-12-21 |
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