SK1142003A3 - Carboxamide compounds and their use as antagonists of a human 11CBY receptor - Google Patents
Carboxamide compounds and their use as antagonists of a human 11CBY receptor Download PDFInfo
- Publication number
- SK1142003A3 SK1142003A3 SK114-2003A SK1142003A SK1142003A3 SK 1142003 A3 SK1142003 A3 SK 1142003A3 SK 1142003 A SK1142003 A SK 1142003A SK 1142003 A3 SK1142003 A3 SK 1142003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- phenyl
- ethoxy
- benzamide
- formula
- diisopropylamino
- Prior art date
Links
- -1 Carboxamide compounds Chemical class 0.000 title claims description 67
- 239000005557 antagonist Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims description 82
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000012453 solvate Substances 0.000 claims description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000002464 receptor antagonist Substances 0.000 claims description 12
- 229940044551 receptor antagonist Drugs 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 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
- 239000003814 drug Substances 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 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 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000020925 Bipolar disease Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 208000028683 bipolar I disease Diseases 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 5
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- LTRZRYVXUAKOOL-UHFFFAOYSA-N 4-benzyl-n-[4-[2-(diethylamino)ethoxy]phenyl]benzamide Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 LTRZRYVXUAKOOL-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 208000035143 Bacterial infection Diseases 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 206010007556 Cardiac failure acute Diseases 0.000 claims description 3
- 206010012218 Delirium Diseases 0.000 claims description 3
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- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 3
- 208000031886 HIV Infections Diseases 0.000 claims description 3
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- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
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- 208000002193 Pain Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 208000010362 Protozoan Infections Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 208000036623 Severe mental retardation Diseases 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 208000025865 Ulcer Diseases 0.000 claims description 3
- 206010046555 Urinary retention Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 230000005856 abnormality Effects 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 208000022531 anorexia Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 206010061428 decreased appetite Diseases 0.000 claims description 3
- 230000035622 drinking Effects 0.000 claims description 3
- 230000002538 fungal effect Effects 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 208000012866 low blood pressure Diseases 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 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 3
- 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 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 231100000397 ulcer Toxicity 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- 150000001555 benzenes 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
- 230000000069 prophylactic effect Effects 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 229940124597 therapeutic agent Drugs 0.000 claims description 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims 2
- 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 1
- NJQFCUOSICXEIH-UHFFFAOYSA-N n-[4-[2-[di(propan-2-yl)amino]ethoxy]phenyl]-4-(4-ethylphenyl)benzamide Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C(=O)NC=2C=CC(OCCN(C(C)C)C(C)C)=CC=2)C=C1 NJQFCUOSICXEIH-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
- VBPMITJBSXBGOI-UHFFFAOYSA-N 3-methoxy-4-(2-pyrrolidin-1-ylethoxy)aniline Chemical compound COC1=CC(N)=CC=C1OCCN1CCCC1 VBPMITJBSXBGOI-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 32
- 239000000243 solution Substances 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- HKFPSPLYKODQFE-UHFFFAOYSA-N 4-bromo-n-[3-methoxy-4-(2-pyrrolidin-1-ylethoxy)phenyl]benzamide Chemical compound C=1C=C(OCCN2CCCC2)C(OC)=CC=1NC(=O)C1=CC=C(Br)C=C1 HKFPSPLYKODQFE-UHFFFAOYSA-N 0.000 description 13
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 13
- 238000003818 flash chromatography Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 7
- 239000003981 vehicle Substances 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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- XOLDVQNALWGUGS-UHFFFAOYSA-N n-[3-acetyl-4-[2-(diethylamino)ethoxy]phenyl]-4-phenylbenzamide Chemical compound C1=C(C(C)=O)C(OCCN(CC)CC)=CC=C1NC(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 XOLDVQNALWGUGS-UHFFFAOYSA-N 0.000 description 6
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 5
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- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 4
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 4
- KTIJUKNOEVHADG-UHFFFAOYSA-N 4-[2-[di(propan-2-yl)amino]ethoxy]-3-methylaniline Chemical compound CC(C)N(C(C)C)CCOC1=CC=C(N)C=C1C KTIJUKNOEVHADG-UHFFFAOYSA-N 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
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- JMZFEHDNIAQMNB-UHFFFAOYSA-N m-aminophenylboronic acid Chemical compound NC1=CC=CC(B(O)O)=C1 JMZFEHDNIAQMNB-UHFFFAOYSA-N 0.000 description 3
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- 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 description 3
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
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| 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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| SK1142003A3 true SK1142003A3 (en) | 2003-06-03 |
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| SK114-2003A SK1142003A3 (en) | 2000-07-31 | 2001-07-26 | Carboxamide compounds and their use as antagonists of a human 11CBY receptor |
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| EP (1) | EP1305304A1 (fr) |
| JP (1) | JP2004505070A (fr) |
| KR (1) | KR20030059084A (fr) |
| CN (1) | CN1444573A (fr) |
| AP (1) | AP2003002720A0 (fr) |
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| US7229987B2 (en) | 2002-05-13 | 2007-06-12 | Eli Lilly And Company | Multicyclic compounds for use as melanin concentrating hormone antagonists in the treatment of obesity and diabetes |
| US7141561B2 (en) | 2002-07-25 | 2006-11-28 | Sanofi-Aventis Deutschland Gmbh | Substituted diaryl heterocycles, process for their preparation and their use as medicaments |
| 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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| 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 |
| US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
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| US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
| AR056155A1 (es) | 2005-10-26 | 2007-09-19 | Bristol Myers Squibb Co | Antagonistas del receptor 1 de la hormona de concentracion de melanina no basica |
| US7553836B2 (en) | 2006-02-06 | 2009-06-30 | Bristol-Myers Squibb Company | Melanin concentrating hormone receptor-1 antagonists |
| KR20080094699A (ko) | 2006-02-15 | 2008-10-23 | 사노피-아벤티스 | 신규 아미노알콜-치환된 아릴디하이드로이소퀴놀리논, 이의제조 방법 및 이의 약물로서의 용도 |
| 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. |
| CA2739488A1 (fr) | 2008-10-15 | 2010-04-22 | Boehringer Ingelheim International Gmbh | Composes de diamide d'heteroaryle fusionnes utilises comme inhibiteurs de mmp-13 |
| CA2738929A1 (fr) | 2008-10-17 | 2010-04-22 | Boehringer Ingelheim International Gmbh | Composes indole a substitution heteroaryle utilises comme inhibiteurs de mmp-13 |
| AR075401A1 (es) | 2009-02-13 | 2011-03-30 | Sanofi Aventis | Indanos sustituidos, procesos para su preparacion y uso de los mismos como un medicamento |
| 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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| FI4225753T3 (fi) * | 2020-10-08 | 2024-08-29 | Leukos Biotech S L | Voimakkaita ja selektiivisiä yhdisteitä serotoniini 1b -reseptorin modulaattoreina |
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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 |
| JP2002521436A (ja) * | 1998-07-28 | 2002-07-16 | スミスクライン・ビーチャム・コーポレイション | 置換アニリド化合物および方法 |
| MXPA01008142A (es) * | 1999-02-10 | 2003-07-21 | Welfide Corp | Compuestos de amida, y uso medicinal de los mismos. |
-
2001
- 2001-07-26 BR BR0112856-6A patent/BR0112856A/pt not_active IP Right Cessation
- 2001-07-26 WO PCT/EP2001/008637 patent/WO2002010146A1/fr not_active Ceased
- 2001-07-26 CN CN01813601A patent/CN1444573A/zh active Pending
- 2001-07-26 JP JP2002515877A patent/JP2004505070A/ja active Pending
- 2001-07-26 EP EP01956562A patent/EP1305304A1/fr not_active Withdrawn
- 2001-07-26 PL PL01365183A patent/PL365183A1/xx unknown
- 2001-07-26 OA OA1200300018A patent/OA12346A/en unknown
- 2001-07-26 EA EA200300064A patent/EA200300064A1/ru unknown
- 2001-07-26 AU AU2001278508A patent/AU2001278508A1/en not_active Abandoned
- 2001-07-26 HU HU0302966A patent/HUP0302966A2/hu unknown
- 2001-07-26 KR KR10-2003-7001409A patent/KR20030059084A/ko not_active Withdrawn
- 2001-07-26 CZ CZ2003297A patent/CZ2003297A3/cs unknown
- 2001-07-26 CA CA002417638A patent/CA2417638A1/fr not_active Abandoned
- 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 IL IL15364501A patent/IL153645A0/xx unknown
- 2001-07-26 MX MXPA03000923A patent/MXPA03000923A/es not_active Application Discontinuation
-
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 |
|---|---|
| WO2002010146A1 (fr) | 2002-02-07 |
| IL153645A0 (en) | 2003-07-06 |
| PL365183A1 (en) | 2004-12-27 |
| MA25829A1 (fr) | 2003-07-01 |
| BR0112856A (pt) | 2003-07-01 |
| HUP0302966A2 (hu) | 2003-12-29 |
| NO20030471D0 (no) | 2003-01-30 |
| BG107510A (bg) | 2003-09-30 |
| EA200300064A1 (ru) | 2003-06-26 |
| AP2003002720A0 (en) | 2003-06-30 |
| OA12346A (en) | 2004-04-13 |
| CZ2003297A3 (cs) | 2003-05-14 |
| MXPA03000923A (es) | 2003-06-09 |
| CA2417638A1 (fr) | 2002-02-07 |
| CN1444573A (zh) | 2003-09-24 |
| JP2004505070A (ja) | 2004-02-19 |
| NO20030471L (no) | 2003-03-28 |
| KR20030059084A (ko) | 2003-07-07 |
| AU2001278508A1 (en) | 2002-02-13 |
| EP1305304A1 (fr) | 2003-05-02 |
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