CA2454613A1 - Substituted anilinic piperidines as mch selective antagonists - Google Patents
Substituted anilinic piperidines as mch selective antagonists Download PDFInfo
- Publication number
- CA2454613A1 CA2454613A1 CA002454613A CA2454613A CA2454613A1 CA 2454613 A1 CA2454613 A1 CA 2454613A1 CA 002454613 A CA002454613 A CA 002454613A CA 2454613 A CA2454613 A CA 2454613A CA 2454613 A1 CA2454613 A1 CA 2454613A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- phenyl
- branched
- alkyl
- mmol
- 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
- 239000005557 antagonist Substances 0.000 title claims abstract description 34
- 150000003053 piperidines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 359
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
- 239000003937 drug carrier Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 304
- 239000000203 mixture Substances 0.000 claims description 154
- -1 cyclopentanyl Chemical group 0.000 claims description 131
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 125000003118 aryl group Chemical group 0.000 claims description 91
- 125000001072 heteroaryl group Chemical group 0.000 claims description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 60
- 208000019901 Anxiety disease Diseases 0.000 claims description 40
- 230000036506 anxiety Effects 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 27
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- 208000008589 Obesity Diseases 0.000 claims description 25
- 235000020824 obesity Nutrition 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 206010020853 Hypertonic bladder Diseases 0.000 claims description 20
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 20
- 208000020629 overactive bladder Diseases 0.000 claims description 20
- 208000000921 Urge Urinary Incontinence Diseases 0.000 claims description 19
- 208000024891 symptom Diseases 0.000 claims description 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 230000004580 weight loss Effects 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 206010046494 urge incontinence Diseases 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 239000000829 suppository Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 claims description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 101150104680 MCH1 gene Proteins 0.000 claims 4
- 101100382379 Rattus norvegicus Cap1 gene Proteins 0.000 claims 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 abstract description 4
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 345
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 256
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 224
- 239000000047 product Substances 0.000 description 188
- 238000005160 1H NMR spectroscopy Methods 0.000 description 179
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 176
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 153
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 152
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 140
- 239000000243 solution Substances 0.000 description 115
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 112
- 239000011541 reaction mixture Substances 0.000 description 98
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 92
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 86
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 84
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 72
- 238000012746 preparative thin layer chromatography Methods 0.000 description 72
- 101800002739 Melanin-concentrating hormone Proteins 0.000 description 64
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 63
- 102000047659 melanin-concentrating hormone Human genes 0.000 description 62
- 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 description 61
- 239000003921 oil Substances 0.000 description 60
- 235000019198 oils Nutrition 0.000 description 60
- 239000000377 silicon dioxide Substances 0.000 description 58
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 54
- 208000035475 disorder Diseases 0.000 description 52
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 50
- 239000002904 solvent Substances 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 238000004587 chromatography analysis Methods 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- JETGTGYZDUEQTF-UHFFFAOYSA-N 2-methyl-n-(3-piperidin-4-ylphenyl)propanamide Chemical compound CC(C)C(=O)NC1=CC=CC(C2CCNCC2)=C1 JETGTGYZDUEQTF-UHFFFAOYSA-N 0.000 description 43
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 41
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 41
- 239000012267 brine Substances 0.000 description 39
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
- 239000010410 layer Substances 0.000 description 38
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 38
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000012043 crude product Substances 0.000 description 33
- 238000010992 reflux Methods 0.000 description 33
- 239000000284 extract Substances 0.000 description 32
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- 125000000753 cycloalkyl group Chemical group 0.000 description 30
- 239000012044 organic layer Substances 0.000 description 30
- 229920005989 resin Polymers 0.000 description 30
- 239000011347 resin Substances 0.000 description 30
- 239000000725 suspension Substances 0.000 description 28
- 125000003342 alkenyl group Chemical group 0.000 description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 description 27
- 125000000304 alkynyl group Chemical group 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 24
- 229910000104 sodium hydride Inorganic materials 0.000 description 23
- 238000004440 column chromatography Methods 0.000 description 22
- 238000004809 thin layer chromatography Methods 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 235000009518 sodium iodide Nutrition 0.000 description 18
- 208000019906 panic disease Diseases 0.000 description 17
- 108020003175 receptors Proteins 0.000 description 17
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
- 150000001412 amines Chemical class 0.000 description 16
- 102000005962 receptors Human genes 0.000 description 16
- 241000700159 Rattus Species 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000002485 urinary effect Effects 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
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- 238000000746 purification Methods 0.000 description 14
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
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- 239000000706 filtrate Substances 0.000 description 13
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 13
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- DHHKPEUQJIEKOA-UHFFFAOYSA-N tert-butyl 2-[6-(nitromethyl)-6-bicyclo[3.2.0]hept-3-enyl]acetate Chemical class C1C=CC2C(CC(=O)OC(C)(C)C)(C[N+]([O-])=O)CC21 DHHKPEUQJIEKOA-UHFFFAOYSA-N 0.000 description 10
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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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
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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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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US89979401A | 2001-07-05 | 2001-07-05 | |
| US09/899,794 | 2001-07-05 | ||
| US4258202A | 2002-01-09 | 2002-01-09 | |
| US10/042,582 | 2002-01-09 | ||
| PCT/US2002/021063 WO2003004027A1 (en) | 2001-07-05 | 2002-07-03 | Substituted anilinic piperidines as mch selective antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2454613A1 true CA2454613A1 (en) | 2003-01-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002454613A Abandoned CA2454613A1 (en) | 2001-07-05 | 2002-07-03 | Substituted anilinic piperidines as mch selective antagonists |
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| EP (1) | EP1411942A4 (https=) |
| JP (1) | JP2004536104A (https=) |
| KR (1) | KR20040027870A (https=) |
| CN (1) | CN1671386A (https=) |
| CA (1) | CA2454613A1 (https=) |
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| NZ (1) | NZ530221A (https=) |
| PL (1) | PL366624A1 (https=) |
| WO (1) | WO2003004027A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
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| US6727264B1 (en) | 2001-07-05 | 2004-04-27 | Synaptic Pharmaceutical Corporation | Substituted anilinic piperidines as MCH selective antagonists |
| US7105544B2 (en) * | 2001-07-05 | 2006-09-12 | Synaptic Pharmaceutical Corporation | Substituted alkyl amido piperidines |
| US7199135B2 (en) | 2001-07-05 | 2007-04-03 | H. Lundbeck A/S | Substituted alkyl amido piperidines |
| CA2468015A1 (en) | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 2-aminoquinoline compounds |
| EP1465888A2 (en) | 2002-01-10 | 2004-10-13 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted benzoimidazole analogues |
| CA2473236A1 (en) | 2002-01-10 | 2003-07-24 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted 2-(4-benzyl-piperazin-1-ylmethyl)- and 2-(4-benzyl-diazepan-1-ylmethyl)-1h-benzoimidazole analogues |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| UA77536C2 (en) | 2002-07-03 | 2006-12-15 | Lundbeck & Co As H | Secondary aminoaniline piperidines as mch1 antagonists and their use |
| UA77814C2 (en) | 2002-07-03 | 2007-01-15 | Lundbeck & Co As H | Spirocyclic piperidines as antagonists of mch1 and use thereof |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| BRPI0407088A (pt) * | 2003-01-28 | 2006-01-24 | Aventis Pharma Sa | Produtos n-aril-heteroaromáticos, composições contendo os mesmos e seu uso |
| FR2850379B1 (fr) * | 2003-01-28 | 2006-11-17 | Aventis Pharma Sa | Produits n-aryl-heteroaromatiques, compositions les contenant et utilisation |
| US7727998B2 (en) * | 2003-02-10 | 2010-06-01 | Banyu Pharmaceutical Co., Ltd. | Melanin-concentrating hormone receptor antagonists containing piperidine derivatives as the active ingredient |
| CN100448870C (zh) * | 2003-05-21 | 2009-01-07 | 万有制药株式会社 | 2-氨基喹啉衍生物 |
| AU2004274309B2 (en) | 2003-09-22 | 2010-04-08 | Msd K.K. | Novel piperidine derivative |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| GB0416728D0 (en) * | 2004-07-27 | 2004-09-01 | 7Tm Pharma As | Medicinal use of receptor ligands |
| US7329656B2 (en) | 2004-10-08 | 2008-02-12 | H. Lundbeck A/S | Arylthiobenzylpiperidine derivatives |
| EP2308839B1 (en) * | 2005-04-20 | 2017-03-01 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| CA2609388C (en) | 2005-05-30 | 2013-08-06 | Banyu Pharmaceutical Co., Ltd. | Novel piperidine derivative |
| JPWO2007018248A1 (ja) | 2005-08-10 | 2009-02-19 | 萬有製薬株式会社 | ピリドン化合物 |
| EP1921065B1 (en) | 2005-08-24 | 2010-10-20 | Banyu Pharmaceutical Co., Ltd. | Phenylpyridone derivative |
| WO2007029847A1 (ja) | 2005-09-07 | 2007-03-15 | Banyu Pharmaceutical Co., Ltd. | 二環性芳香族置換ピリドン誘導体 |
| BRPI0616463A2 (pt) | 2005-09-29 | 2011-06-21 | Merck & Co Inc | composto, composição farmacêutica, e, uso de um composto |
| AU2006301376A1 (en) | 2005-10-11 | 2007-04-19 | F. Hoffmann-La Roche Ag | Isoxazole derivatives |
| AU2006307046A1 (en) | 2005-10-27 | 2007-05-03 | Msd K.K. | Novel benzoxathiin derivative |
| ES2341131T3 (es) | 2005-11-09 | 2010-06-15 | F.Hoffmann-La Roche Ag | Derivados de 3-aril-isoxazol-4-carbonil-benzofurano. |
| US8158791B2 (en) | 2005-11-10 | 2012-04-17 | Msd K.K. | Aza-substituted spiro derivatives |
| JP5015172B2 (ja) | 2005-12-23 | 2012-08-29 | エフ.ホフマン−ラ ロシュ アーゲー | アリール−イソオキサゾロ−4−イル−オキサジアゾール誘導体 |
| ATE527255T1 (de) | 2005-12-27 | 2011-10-15 | Hoffmann La Roche | Aryl-isoxazol-4-yl-imidazol-derivate |
| WO2007082806A1 (en) | 2006-01-17 | 2007-07-26 | F. Hoffmann-La Roche Ag | Aryl-isoxazol-4-yl-imidazo[1,2-a]pyridine useful for the treatment of alzheimer’s disease via gaba receptors |
| CN101484424B (zh) * | 2006-02-28 | 2014-05-14 | 达特神经科学(开曼)有限公司 | 治疗化合物 |
| AU2007267183B2 (en) | 2006-05-31 | 2011-10-20 | F. Hoffmann-La Roche Ag | Aryl-4-ethynyl-isoxazole derivatives |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−2,4−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| JP5489333B2 (ja) | 2006-09-22 | 2014-05-14 | メルク・シャープ・アンド・ドーム・コーポレーション | 脂肪酸合成阻害剤を用いた治療の方法 |
| AU2007301126A1 (en) | 2006-09-28 | 2008-04-03 | Banyu Pharmaceutical Co., Ltd. | Diaryl ketimine derivative |
| CA2682727C (en) | 2007-04-02 | 2016-03-22 | Banyu Pharmaceutical Co., Ltd. | Indoledione derivative |
| US8198307B2 (en) * | 2007-05-11 | 2012-06-12 | Korea Research Institute Of Chemical Technology | Imidazole derivatives having aryl piperidine substituent, method for preparation thereof and pharmaceutical compositions containing same |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| EP2527360B1 (en) | 2007-06-04 | 2015-10-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9810671D0 (en) * | 1998-05-18 | 1998-07-15 | Pfizer Ltd | Anti-pruritic agents |
| GB9912413D0 (en) * | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| JP2004502423A (ja) * | 2000-07-05 | 2004-01-29 | シナプティック・ファーマスーティカル・コーポレーション | ヒトメラニン濃縮ホルモン受容体(mch1)をコードするdna及びその使用 |
-
2002
- 2002-07-03 EP EP02746843A patent/EP1411942A4/en not_active Withdrawn
- 2002-07-03 MX MXPA03011886A patent/MXPA03011886A/es not_active Application Discontinuation
- 2002-07-03 EA EA200400146A patent/EA005934B1/ru not_active IP Right Cessation
- 2002-07-03 JP JP2003510038A patent/JP2004536104A/ja not_active Withdrawn
- 2002-07-03 HU HU0401880A patent/HUP0401880A2/hu unknown
- 2002-07-03 WO PCT/US2002/021063 patent/WO2003004027A1/en not_active Ceased
- 2002-07-03 PL PL02366624A patent/PL366624A1/xx not_active Application Discontinuation
- 2002-07-03 CN CNA028172124A patent/CN1671386A/zh active Pending
- 2002-07-03 NZ NZ530221A patent/NZ530221A/xx unknown
- 2002-07-03 CA CA002454613A patent/CA2454613A1/en not_active Abandoned
- 2002-07-03 KR KR10-2004-7000087A patent/KR20040027870A/ko not_active Ceased
- 2002-07-03 IL IL15969702A patent/IL159697A0/xx unknown
-
2003
- 2003-12-18 IS IS7085A patent/IS7085A/is unknown
-
2004
- 2004-01-05 NO NO20040028A patent/NO20040028L/no not_active Application Discontinuation
- 2004-02-02 CO CO04007748A patent/CO5670352A2/es not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
Also Published As
| Publication number | Publication date |
|---|---|
| EA005934B1 (ru) | 2005-08-25 |
| EP1411942A4 (en) | 2005-01-26 |
| EP1411942A1 (en) | 2004-04-28 |
| AU2002316531B2 (en) | 2007-09-13 |
| CN1671386A (zh) | 2005-09-21 |
| CO5670352A2 (es) | 2006-08-31 |
| JP2004536104A (ja) | 2004-12-02 |
| NZ530221A (en) | 2006-03-31 |
| NO20040028L (no) | 2004-03-04 |
| MXPA03011886A (es) | 2005-03-07 |
| HUP0401880A2 (hu) | 2005-01-28 |
| WO2003004027A1 (en) | 2003-01-16 |
| IS7085A (is) | 2003-12-18 |
| EA200400146A1 (ru) | 2004-08-26 |
| PL366624A1 (en) | 2005-02-07 |
| KR20040027870A (ko) | 2004-04-01 |
| IL159697A0 (en) | 2004-06-20 |
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