BG107510A - Карбоксамидни съединения и тяхното използване като антагонисти на човешки 11 cby рецептор - Google Patents
Карбоксамидни съединения и тяхното използване като антагонисти на човешки 11 cby рецептор Download PDFInfo
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- BG107510A BG107510A BG107510A BG10751003A BG107510A BG 107510 A BG107510 A BG 107510A BG 107510 A BG107510 A BG 107510A BG 10751003 A BG10751003 A BG 10751003A BG 107510 A BG107510 A BG 107510A
- Authority
- BG
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- Prior art keywords
- phenyl
- ethoxy
- formula
- benzamide
- compound
- Prior art date
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- -1 CARBOXAMIDE COMPOUNDS Chemical class 0.000 title claims abstract description 39
- 239000005557 antagonist Substances 0.000 title abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 119
- 150000003839 salts Chemical class 0.000 claims abstract description 41
- 239000012453 solvate Substances 0.000 claims abstract description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 5
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 93
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002464 receptor antagonist Substances 0.000 claims description 7
- 229940044551 receptor antagonist Drugs 0.000 claims description 7
- QPTCSDKORSUWFG-UHFFFAOYSA-N n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-4-phenylbenzamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 QPTCSDKORSUWFG-UHFFFAOYSA-N 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 5
- JQXVNQZQHZMKQH-UHFFFAOYSA-N 4-benzyl-n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]benzamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 JQXVNQZQHZMKQH-UHFFFAOYSA-N 0.000 claims description 5
- MTXOITXWFSWMER-UHFFFAOYSA-N 4-cyclohexyl-n-[4-[2-(diethylamino)ethoxy]phenyl]benzamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC(=O)C1=CC=C(C2CCCCC2)C=C1 MTXOITXWFSWMER-UHFFFAOYSA-N 0.000 claims description 5
- ZFBLUSUFXWIAIQ-UHFFFAOYSA-N 4-cyclohexyl-n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]benzamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C1=CC=C(C2CCCCC2)C=C1 ZFBLUSUFXWIAIQ-UHFFFAOYSA-N 0.000 claims description 5
- BZALKVRGDXMCFN-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]phenyl]-4-phenoxybenzamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 BZALKVRGDXMCFN-UHFFFAOYSA-N 0.000 claims description 5
- OJVPDOZEWDWHQC-UHFFFAOYSA-N n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-4-phenoxybenzamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 OJVPDOZEWDWHQC-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- SCEBDBNGUCNRCE-UHFFFAOYSA-N 4-(4-ethylphenyl)benzoic acid Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C(O)=O)C=C1 SCEBDBNGUCNRCE-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- QSSJKXMVTYSDBI-UHFFFAOYSA-N C(C1=CC=CC=C1)C1=CC=C(C(=O)NC2=CC=C(C=C2)OCCN(CC)CC)C=C1.C(C)(C)N(CCOC1=CC=C(C=C1)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC)C(C)C Chemical compound C(C1=CC=CC=C1)C1=CC=C(C(=O)NC2=CC=C(C=C2)OCCN(CC)CC)C=C1.C(C)(C)N(CCOC1=CC=C(C=C1)NC(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CC)C(C)C QSSJKXMVTYSDBI-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
- RIWGURHNDVMOIO-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]phenyl]-3-phenoxybenzamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 RIWGURHNDVMOIO-UHFFFAOYSA-N 0.000 claims description 4
- HUDPEMVLPBMFRV-UHFFFAOYSA-N n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-3-phenoxybenzamide Chemical compound C1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 HUDPEMVLPBMFRV-UHFFFAOYSA-N 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 208000024714 major depressive disease Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- FRGOIWVLARRWPC-UHFFFAOYSA-N n-[4-[2-[di(propan-2-yl)amino]ethoxy]-2-fluorophenyl]-4-phenylbenzamide Chemical compound FC1=CC(OCCN(C(C)C)C(C)C)=CC=C1NC(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 FRGOIWVLARRWPC-UHFFFAOYSA-N 0.000 claims description 2
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- 229910052705 radium Inorganic materials 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
- 239000000203 mixture Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000000243 solution Substances 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 125000001424 substituent group Chemical group 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 230000008878 coupling Effects 0.000 description 11
- 238000010168 coupling process Methods 0.000 description 11
- 238000005859 coupling reaction Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- JXIJUAWSDBACEB-UHFFFAOYSA-N 1-chloro-2-methoxy-4-nitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=CC=C1Cl JXIJUAWSDBACEB-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 241000282412 Homo Species 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- NDNIPPKLIDCYGD-UHFFFAOYSA-N 4-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 NDNIPPKLIDCYGD-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
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- VBPMITJBSXBGOI-UHFFFAOYSA-N 3-methoxy-4-(2-pyrrolidin-1-ylethoxy)aniline Chemical compound COC1=CC(N)=CC=C1OCCN1CCCC1 VBPMITJBSXBGOI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 125000004432 carbon atom Chemical group C* 0.000 description 4
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- OBPFHJKEIFNNHY-UHFFFAOYSA-N 1-[2-(2-methoxy-4-nitrophenoxy)ethyl]pyrrolidine Chemical compound COC1=CC([N+]([O-])=O)=CC=C1OCCN1CCCC1 OBPFHJKEIFNNHY-UHFFFAOYSA-N 0.000 description 3
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0018758.3A GB0018758D0 (en) | 2000-07-31 | 2000-07-31 | Novel use and compunds |
| GB0112544A GB0112544D0 (en) | 2001-05-23 | 2001-05-23 | Novel use and compounds |
| PCT/EP2001/008637 WO2002010146A1 (fr) | 2000-07-31 | 2001-07-26 | Composes du carboxamide et leur utilisation comme antagonistes d'un recepteur 11cby humain |
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| BG107510A true BG107510A (bg) | 2003-09-30 |
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| BG107510A BG107510A (bg) | 2000-07-31 | 2003-01-30 | Карбоксамидни съединения и тяхното използване като антагонисти на човешки 11 cby рецептор |
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| JP (1) | JP2004505070A (fr) |
| KR (1) | KR20030059084A (fr) |
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|---|---|---|---|---|
| JP2005529923A (ja) * | 2002-05-13 | 2005-10-06 | イーライ・リリー・アンド・カンパニー | 肥満および糖尿病の治療におけるメラニン凝集ホルモンアンタゴニストとして使用するための多環式化合物 |
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| DE10233817A1 (de) * | 2002-07-25 | 2004-02-12 | Aventis Pharma Deutschland Gmbh | Substituierte Diarylheterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE10306250A1 (de) * | 2003-02-14 | 2004-09-09 | Aventis Pharma Deutschland Gmbh | Substituierte N-Arylheterozyklen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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| ES2350837T3 (es) * | 2003-05-01 | 2011-01-27 | Bristol-Myers Squibb Company | Compuestos de pirazol-amida sustituidos con arilo útiles como inhibidores de quinasas. |
| WO2005012256A1 (fr) | 2003-07-22 | 2005-02-10 | Astex Therapeutics Limited | Composes 1h-pyrazole 3,4-disubstitues et leur utilisation en tant que kinases dependant des cyclines (cdk) et modulateurs de la glycogene synthase kinase-3 (gsk-3) |
| US7037927B2 (en) | 2003-10-16 | 2006-05-02 | Abbott Laboratories | Amides that inhibit vanilloid receptor subtype 1 (VR1) receptor |
| US7241787B2 (en) | 2004-01-25 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Substituted N-cycloexylimidazolinones, process for their preparation and their use as medicaments |
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| EP1720826A4 (fr) * | 2004-03-02 | 2007-10-31 | Neurogen Corp | Analogues arylamide d'acide biphenyl-4-carboxylique heteroalkyle substitue |
| US7605176B2 (en) | 2004-03-06 | 2009-10-20 | Boehringer Ingelheim International Gmbh | β-ketoamide compounds with MCH antagonistic activity |
| DE102004010893A1 (de) * | 2004-03-06 | 2005-09-22 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue ß-Ketoamid-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
| TW200613272A (en) | 2004-08-13 | 2006-05-01 | Astrazeneca Ab | Isoindolone compounds and their use as metabotropic glutamate receptor potentiators |
| DE102004039789A1 (de) | 2004-08-16 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Arylsubstituierte polycyclische Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| AR054425A1 (es) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
| US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
| US8618115B2 (en) | 2005-10-26 | 2013-12-31 | Bristol-Myers Squibb Company | Substituted thieno[3,2-d]pyrimidinones as MCHR1 antagonists and methods for using them |
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| DE602007011897D1 (de) | 2006-02-15 | 2011-02-24 | Sanofi Aventis | Neue aminoalkohol-substituierte aryldihydroisochinolinone, herstellungsverfahren und ihre verwendung als medikamente |
| GB0625523D0 (en) * | 2006-12-21 | 2007-01-31 | Ge Healthcare Ltd | In vivo imaging agents |
| TWI417100B (zh) | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-842之用途 |
| EP2025674A1 (fr) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Tetrahydronaphthaline substituée, son procédé de fabrication et son utilisation en tant que médicament |
| PE20091928A1 (es) | 2008-05-29 | 2009-12-31 | Bristol Myers Squibb Co | Tienopirimidinas hidroxisustituidas como antagonistas de receptor-1 de hormona concentradora de melanina no basicos |
| US7790760B2 (en) | 2008-06-06 | 2010-09-07 | Astrazeneca Ab | Metabotropic glutamate receptor isoxazole ligands and their use as potentiators 286 |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
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| TW201040154A (en) | 2009-02-13 | 2010-11-16 | Sanofi Aventis | Novel substituted indanes, process for preparation thereof and use thereof as a medicament |
| UY32443A (es) | 2009-02-13 | 2010-09-30 | Sanofi Aventis | Nuevos tetrahidronaftalenos, procesos para su preparación y uso de los mismos como medicamento. |
| WO2013130968A1 (fr) * | 2012-03-01 | 2013-09-06 | University Of Cincinnati | Composés activés par dro en tant que thérapies anti-cancer sélectives |
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| HRP20241184T1 (hr) * | 2020-10-08 | 2024-11-22 | Leukos Biotech, S.L. | Moćni i selektivni spojevi kao modulatori serotonin 1b receptora |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA985542B (en) * | 1997-07-03 | 1999-04-07 | Smithkline Beecham Corp | Substituted benzanilides as CCR5 receptor ligands antiinflammatory agents and antiviral agents |
| HUP0102752A3 (en) * | 1998-07-28 | 2002-11-28 | Smithkline Beecham Corp | Substituted anilide compounds |
| KR100659007B1 (ko) * | 1999-02-10 | 2007-02-28 | 미츠비시 웰파마 가부시키가이샤 | 아미드 화합물 및 그 의약으로서의 용도 |
-
2001
- 2001-07-26 MX MXPA03000923A patent/MXPA03000923A/es not_active Application Discontinuation
- 2001-07-26 KR KR10-2003-7001409A patent/KR20030059084A/ko not_active Withdrawn
- 2001-07-26 JP JP2002515877A patent/JP2004505070A/ja active Pending
- 2001-07-26 OA OA1200300018A patent/OA12346A/en unknown
- 2001-07-26 WO PCT/EP2001/008637 patent/WO2002010146A1/fr not_active Ceased
- 2001-07-26 CA CA002417638A patent/CA2417638A1/fr not_active Abandoned
- 2001-07-26 CZ CZ2003297A patent/CZ2003297A3/cs unknown
- 2001-07-26 EA EA200300064A patent/EA200300064A1/ru unknown
- 2001-07-26 BR BR0112856-6A patent/BR0112856A/pt not_active IP Right Cessation
- 2001-07-26 HU HU0302966A patent/HUP0302966A2/hu unknown
- 2001-07-26 IL IL15364501A patent/IL153645A0/xx unknown
- 2001-07-26 PL PL01365183A patent/PL365183A1/xx unknown
- 2001-07-26 SK SK114-2003A patent/SK1142003A3/sk not_active Application Discontinuation
- 2001-07-26 AP APAP/P/2003/002720A patent/AP2003002720A0/en unknown
- 2001-07-26 CN CN01813601A patent/CN1444573A/zh active Pending
- 2001-07-26 AU AU2001278508A patent/AU2001278508A1/en not_active Abandoned
- 2001-07-26 EP EP01956562A patent/EP1305304A1/fr not_active Withdrawn
-
2003
- 2003-01-24 MA MA27012A patent/MA25829A1/fr unknown
- 2003-01-30 NO NO20030471A patent/NO20030471L/no not_active Application Discontinuation
- 2003-01-30 BG BG107510A patent/BG107510A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EA200300064A1 (ru) | 2003-06-26 |
| MXPA03000923A (es) | 2003-06-09 |
| BR0112856A (pt) | 2003-07-01 |
| PL365183A1 (en) | 2004-12-27 |
| CA2417638A1 (fr) | 2002-02-07 |
| MA25829A1 (fr) | 2003-07-01 |
| WO2002010146A1 (fr) | 2002-02-07 |
| HUP0302966A2 (hu) | 2003-12-29 |
| OA12346A (en) | 2004-04-13 |
| CN1444573A (zh) | 2003-09-24 |
| IL153645A0 (en) | 2003-07-06 |
| EP1305304A1 (fr) | 2003-05-02 |
| AU2001278508A1 (en) | 2002-02-13 |
| JP2004505070A (ja) | 2004-02-19 |
| AP2003002720A0 (en) | 2003-06-30 |
| KR20030059084A (ko) | 2003-07-07 |
| CZ2003297A3 (cs) | 2003-05-14 |
| NO20030471D0 (no) | 2003-01-30 |
| NO20030471L (no) | 2003-03-28 |
| SK1142003A3 (en) | 2003-06-03 |
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