JP2007509118A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2007509118A5 JP2007509118A5 JP2006536171A JP2006536171A JP2007509118A5 JP 2007509118 A5 JP2007509118 A5 JP 2007509118A5 JP 2006536171 A JP2006536171 A JP 2006536171A JP 2006536171 A JP2006536171 A JP 2006536171A JP 2007509118 A5 JP2007509118 A5 JP 2007509118A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- alkyl
- oxoquinazolin
- methyl
- methylbenzamide
- 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.)
- Granted
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 412
- -1 hydroxy, amino Chemical group 0.000 claims description 248
- 125000003545 alkoxy group Chemical group 0.000 claims description 166
- 125000001424 substituent group Chemical group 0.000 claims description 120
- 125000000623 heterocyclic group Chemical group 0.000 claims description 68
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
- 125000003282 alkyl amino group Chemical group 0.000 claims description 60
- 125000005843 halogen group Chemical group 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 44
- 125000000304 alkynyl group Chemical group 0.000 claims description 44
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 26
- 125000001589 carboacyl group Chemical group 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000001721 carbon Chemical group 0.000 claims description 12
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 108090000695 Cytokines Proteins 0.000 claims description 7
- 102000004127 Cytokines Human genes 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 5
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 5
- 125000005997 bromomethyl group Chemical group 0.000 claims description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 5
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- FDPVTENMNDHFNK-UHFFFAOYSA-N 2-amino-n-phenylbenzamide Chemical compound NC1=CC=CC=C1C(=O)NC1=CC=CC=C1 FDPVTENMNDHFNK-UHFFFAOYSA-N 0.000 claims description 3
- 208000030507 AIDS Diseases 0.000 claims description 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- 238000010976 amide bond formation reaction Methods 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 208000031225 myocardial ischemia Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- HCPMOUXUWOUFKH-UHFFFAOYSA-N n-cyclobutyl-4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3-yl]benzamide Chemical group C1CN(C)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CCC2)C)C2=O)C2=C1 HCPMOUXUWOUFKH-UHFFFAOYSA-N 0.000 claims description 2
- XHFABWPTYFWNFH-UHFFFAOYSA-N n-cyclopropyl-3-[6-(1,4-diazepan-1-yl)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical group CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CCCNCC1 XHFABWPTYFWNFH-UHFFFAOYSA-N 0.000 claims description 2
- HUDRXSXKLYHUBS-UHFFFAOYSA-N n-cyclopropyl-3-[6-[1-(cyclopropylmethyl)piperidin-4-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical group CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC(CC1)CCN1CC1CC1 HUDRXSXKLYHUBS-UHFFFAOYSA-N 0.000 claims description 2
- JZLORZUOLUEHEM-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(4-oxo-6-piperazin-1-ylquinazolin-3-yl)benzamide Chemical group CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CCNCC1 JZLORZUOLUEHEM-UHFFFAOYSA-N 0.000 claims description 2
- MATLJYUMZLLGDA-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(4-oxo-6-piperidin-4-yloxyquinazolin-3-yl)benzamide Chemical group CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC1CCNCC1 MATLJYUMZLLGDA-UHFFFAOYSA-N 0.000 claims description 2
- QCRGVBHYRARZNG-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(4-propan-2-ylpiperazin-1-yl)quinazolin-3-yl]benzamide Chemical compound C1CN(C(C)C)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 QCRGVBHYRARZNG-UHFFFAOYSA-N 0.000 claims description 2
- SSBANYVKJLMCBN-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(4-propylpiperazin-1-yl)quinazolin-3-yl]benzamide Chemical compound C1CN(CCC)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 SSBANYVKJLMCBN-UHFFFAOYSA-N 0.000 claims description 2
- ZMAZXHICVRYLQN-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3-yl]benzamide Chemical group C1CN(C)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 ZMAZXHICVRYLQN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 230000001404 mediated effect Effects 0.000 claims 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- DVXQJRHVCWLHHO-UHFFFAOYSA-N 2-[4-[3-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-4-oxoquinazolin-6-yl]piperazin-1-yl]acetic acid Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CCN(CC(O)=O)CC1 DVXQJRHVCWLHHO-UHFFFAOYSA-N 0.000 claims 1
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 1
- WJAJSHFYWOTWBJ-UHFFFAOYSA-N 3-[6-(2-acetamidoethoxy)-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound O=C1C2=CC(OCCNC(=O)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 WJAJSHFYWOTWBJ-UHFFFAOYSA-N 0.000 claims 1
- FICYFFIZSUQGHH-UHFFFAOYSA-N 3-[6-(4-acetylpiperazin-1-yl)-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound C1CN(C(=O)C)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 FICYFFIZSUQGHH-UHFFFAOYSA-N 0.000 claims 1
- RHDNMCREZVZWHW-UHFFFAOYSA-N 3-[6-(4-cyclobutylpiperazin-1-yl)-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N(CC1)CCN1C1CCC1 RHDNMCREZVZWHW-UHFFFAOYSA-N 0.000 claims 1
- UKEPZCHVAWBLRH-UHFFFAOYSA-N 3-[6-[2-(azetidin-1-yl)ethoxy]-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1CCC1 UKEPZCHVAWBLRH-UHFFFAOYSA-N 0.000 claims 1
- UIWWFGOEPSHIBK-UHFFFAOYSA-N 3-[6-[2-(tert-butylamino)ethoxy]-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC(OCCNC(C)(C)C)=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 UIWWFGOEPSHIBK-UHFFFAOYSA-N 0.000 claims 1
- UHRLTJJGLOTWIG-UHFFFAOYSA-N 3-[6-[2-[cyclobutylmethyl(methyl)amino]ethoxy]-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound C1CCC1CN(C)CCOC(C=C1C2=O)=CC=C1N=CN2C(C(=CC=1)C)=CC=1C(=O)NC1CC1 UHRLTJJGLOTWIG-UHFFFAOYSA-N 0.000 claims 1
- CSQOYWGLIIYRSM-UHFFFAOYSA-N 3-[6-[3-[cyclobutylmethyl(methyl)amino]propoxy]-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound C1CCC1CN(C)CCCOC(C=C1C2=O)=CC=C1N=CN2C(C(=CC=1)C)=CC=1C(=O)NC1CC1 CSQOYWGLIIYRSM-UHFFFAOYSA-N 0.000 claims 1
- GPRFBOGOKHUAOT-UHFFFAOYSA-N 3-[6-[4-(cyanomethyl)piperazin-1-yl]-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CCN(CC#N)CC1 GPRFBOGOKHUAOT-UHFFFAOYSA-N 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- HLUINUXJZPPVQK-UHFFFAOYSA-N 4-methyl-n-(1-methylcyclopropyl)-3-[4-oxo-6-(2-piperidin-1-ylethoxy)quinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2(C)CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1CCCCC1 HLUINUXJZPPVQK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 206010010356 Congenital anomaly Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 206010061876 Obstruction Diseases 0.000 claims 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000016396 cytokine production Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
- OUDISZOHUHEWBI-UHFFFAOYSA-N n-cyclobutyl-4-methyl-3-[4-oxo-6-(4-propan-2-ylpiperazin-1-yl)quinazolin-3-yl]benzamide Chemical compound C1CN(C(C)C)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CCC2)C)C2=O)C2=C1 OUDISZOHUHEWBI-UHFFFAOYSA-N 0.000 claims 1
- IVHSVYVJVSFWFF-UHFFFAOYSA-N n-cyclopropyl-3-(6-hydroxy-4-oxoquinazolin-3-yl)-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC(O)=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 IVHSVYVJVSFWFF-UHFFFAOYSA-N 0.000 claims 1
- CSCSGDAFXRVYLU-UHFFFAOYSA-N n-cyclopropyl-3-(6-iodo-4-oxoquinazolin-3-yl)-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC(I)=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 CSCSGDAFXRVYLU-UHFFFAOYSA-N 0.000 claims 1
- MIHWXBMNRZJFOR-UHFFFAOYSA-N n-cyclopropyl-3-(6-methoxy-4-oxoquinazolin-3-yl)-4-methylbenzamide Chemical compound O=C1C2=CC(OC)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 MIHWXBMNRZJFOR-UHFFFAOYSA-N 0.000 claims 1
- VQWNYJDUIDCODQ-UHFFFAOYSA-N n-cyclopropyl-3-(7-fluoro-4-oxoquinazolin-3-yl)-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC=C(F)C=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 VQWNYJDUIDCODQ-UHFFFAOYSA-N 0.000 claims 1
- IPBMVBGFSVPCKG-UHFFFAOYSA-N n-cyclopropyl-3-(7-methoxy-4-oxoquinazolin-3-yl)-4-methylbenzamide Chemical compound C=1C(OC)=CC=C(C2=O)C=1N=CN2C(C(=CC=1)C)=CC=1C(=O)NC1CC1 IPBMVBGFSVPCKG-UHFFFAOYSA-N 0.000 claims 1
- HSGAOPFYDBVZHU-UHFFFAOYSA-N n-cyclopropyl-3-(8-methoxy-4-oxoquinazolin-3-yl)-4-methylbenzamide Chemical compound COC1=CC=CC(C2=O)=C1N=CN2C(C(=CC=1)C)=CC=1C(=O)NC1CC1 HSGAOPFYDBVZHU-UHFFFAOYSA-N 0.000 claims 1
- YKXCKBZVEVRGNU-UHFFFAOYSA-N n-cyclopropyl-3-[6-(1-cyclopropylpiperidin-4-yl)oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC(CC1)CCN1C1CC1 YKXCKBZVEVRGNU-UHFFFAOYSA-N 0.000 claims 1
- PBQVNJVCYLEJIP-UHFFFAOYSA-N n-cyclopropyl-3-[6-(1-ethylpyrrolidin-3-yl)oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1N(CC)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 PBQVNJVCYLEJIP-UHFFFAOYSA-N 0.000 claims 1
- LGUCHTJZQMIJFE-UHFFFAOYSA-N n-cyclopropyl-3-[6-(2,3-dihydroxy-2-methylpropoxy)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC(OCC(C)(O)CO)=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 LGUCHTJZQMIJFE-UHFFFAOYSA-N 0.000 claims 1
- PTBIULMNOAVJQF-UHFFFAOYSA-N n-cyclopropyl-3-[6-(2-hydroxy-2-methyl-3-pyrrolidin-1-ylpropoxy)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCC(C)(O)CN1CCCC1 PTBIULMNOAVJQF-UHFFFAOYSA-N 0.000 claims 1
- PFHZOXWQGGWOCC-UHFFFAOYSA-N n-cyclopropyl-3-[6-(2-imidazol-1-ylethoxy)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1C=CN=C1 PFHZOXWQGGWOCC-UHFFFAOYSA-N 0.000 claims 1
- PFBMSZRTCQZXIN-UHFFFAOYSA-N n-cyclopropyl-3-[6-(3-hydroxyazetidin-1-yl)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CC(O)C1 PFBMSZRTCQZXIN-UHFFFAOYSA-N 0.000 claims 1
- XKZDKVJGPJFVRK-UHFFFAOYSA-N n-cyclopropyl-3-[6-(4-ethyl-1,4-diazepan-1-yl)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(CC)CCCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 XKZDKVJGPJFVRK-UHFFFAOYSA-N 0.000 claims 1
- HRONGNIWVAVTFC-UHFFFAOYSA-N n-cyclopropyl-3-[6-(4-hydroxypiperidin-1-yl)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CCC(O)CC1 HRONGNIWVAVTFC-UHFFFAOYSA-N 0.000 claims 1
- LXWSPBJSHTYHKN-UHFFFAOYSA-N n-cyclopropyl-3-[6-[(3-hydroxy-2,2-dimethylpropyl)amino]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC(NCC(C)(C)CO)=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 LXWSPBJSHTYHKN-UHFFFAOYSA-N 0.000 claims 1
- PBQVNJVCYLEJIP-HXUWFJFHSA-N n-cyclopropyl-3-[6-[(3r)-1-ethylpyrrolidin-3-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1N(CC)CC[C@H]1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 PBQVNJVCYLEJIP-HXUWFJFHSA-N 0.000 claims 1
- GSJAQNVOUNAGFD-LJQANCHMSA-N n-cyclopropyl-3-[6-[(3r)-4-(cyclopropylmethyl)-3-methylpiperazin-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C([C@H]1C)N(C=2C=C3C(=O)N(C=4C(=CC=C(C=4)C(=O)NC4CC4)C)C=NC3=CC=2)CCN1CC1CC1 GSJAQNVOUNAGFD-LJQANCHMSA-N 0.000 claims 1
- IGYUYYXMKCXLLQ-GOSISDBHSA-N n-cyclopropyl-3-[6-[(3r)-4-ethyl-3-methylpiperazin-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1[C@@H](C)N(CC)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 IGYUYYXMKCXLLQ-GOSISDBHSA-N 0.000 claims 1
- NYDZOAQNQUWWAU-CALCHBBNSA-N n-cyclopropyl-3-[6-[(3r,5s)-3,5-dimethylpiperazin-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 NYDZOAQNQUWWAU-CALCHBBNSA-N 0.000 claims 1
- PNEXVVGLXCTFKG-QFIPXVFZSA-N n-cyclopropyl-3-[6-[(3s)-1-(cyclopropylmethyl)pyrrolidin-3-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C([C@@H](C1)OC2=CC=C3N=CN(C(C3=C2)=O)C2=CC(=CC=C2C)C(=O)NC2CC2)CN1CC1CC1 PNEXVVGLXCTFKG-QFIPXVFZSA-N 0.000 claims 1
- PBQVNJVCYLEJIP-FQEVSTJZSA-N n-cyclopropyl-3-[6-[(3s)-1-ethylpyrrolidin-3-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1N(CC)CC[C@@H]1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 PBQVNJVCYLEJIP-FQEVSTJZSA-N 0.000 claims 1
- UFECOQXRSYPWRA-CALCHBBNSA-N n-cyclopropyl-3-[6-[(3s,5r)-3,5-dimethylpiperazin-1-yl]-2-methyl-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=CC=C(N=C(C)N(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 UFECOQXRSYPWRA-CALCHBBNSA-N 0.000 claims 1
- NZZMNDSXNLRGBA-UHFFFAOYSA-N n-cyclopropyl-3-[6-[1-(2-fluoroethyl)piperidin-4-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC1CCN(CCF)CC1 NZZMNDSXNLRGBA-UHFFFAOYSA-N 0.000 claims 1
- GUUJNSXSHCOSIN-UHFFFAOYSA-N n-cyclopropyl-3-[6-[1-(2-hydroxy-2-methylpropyl)piperidin-4-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC1CCN(CC(C)(C)O)CC1 GUUJNSXSHCOSIN-UHFFFAOYSA-N 0.000 claims 1
- MBEYHBZHNWESBD-UHFFFAOYSA-N n-cyclopropyl-3-[6-[1-(2-hydroxyethyl)piperidin-4-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC1CCN(CCO)CC1 MBEYHBZHNWESBD-UHFFFAOYSA-N 0.000 claims 1
- MHHJHGCPMKRMEL-UHFFFAOYSA-N n-cyclopropyl-3-[6-[1-(2-methoxyethyl)piperidin-4-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(CCOC)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 MHHJHGCPMKRMEL-UHFFFAOYSA-N 0.000 claims 1
- PNEXVVGLXCTFKG-UHFFFAOYSA-N n-cyclopropyl-3-[6-[1-(cyclopropylmethyl)pyrrolidin-3-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC(C1)CCN1CC1CC1 PNEXVVGLXCTFKG-UHFFFAOYSA-N 0.000 claims 1
- LNAVQPIOKWMYGV-GOSISDBHSA-N n-cyclopropyl-3-[6-[1-[(2r)-2-hydroxypropyl]piperidin-4-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(C[C@H](O)C)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 LNAVQPIOKWMYGV-GOSISDBHSA-N 0.000 claims 1
- LNAVQPIOKWMYGV-SFHVURJKSA-N n-cyclopropyl-3-[6-[1-[(2s)-2-hydroxypropyl]piperidin-4-yl]oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(C[C@@H](O)C)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 LNAVQPIOKWMYGV-SFHVURJKSA-N 0.000 claims 1
- YILVWNABBHMIST-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-(4-hydroxypiperidin-1-yl)ethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1CCC(O)CC1 YILVWNABBHMIST-UHFFFAOYSA-N 0.000 claims 1
- UNJJXYGJEIHFHT-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-(dimethylamino)-2-methylpropoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCC(C)(C)N(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 UNJJXYGJEIHFHT-UHFFFAOYSA-N 0.000 claims 1
- VLTCTDVFMHDSMX-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-(dimethylamino)-2-oxoethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCC(=O)N(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 VLTCTDVFMHDSMX-UHFFFAOYSA-N 0.000 claims 1
- WZMLJWAUXHYMRE-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-(dimethylamino)ethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCCN(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 WZMLJWAUXHYMRE-UHFFFAOYSA-N 0.000 claims 1
- BVEHSYQNIRZTDN-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-(methanesulfonamido)ethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC(OCCNS(C)(=O)=O)=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 BVEHSYQNIRZTDN-UHFFFAOYSA-N 0.000 claims 1
- NALFVCKYTFAUMJ-FQEVSTJZSA-N n-cyclopropyl-3-[6-[2-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]ethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1CCC[C@H]1CO NALFVCKYTFAUMJ-FQEVSTJZSA-N 0.000 claims 1
- BULRNDVFABOUKN-GOSISDBHSA-N n-cyclopropyl-3-[6-[2-[(3r)-3-fluoropyrrolidin-1-yl]ethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1CC[C@@H](F)C1 BULRNDVFABOUKN-GOSISDBHSA-N 0.000 claims 1
- GCCCHFAPYLFBIP-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-[2-methoxyethyl(methyl)amino]ethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCCN(C)CCOC)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 GCCCHFAPYLFBIP-UHFFFAOYSA-N 0.000 claims 1
- FQAWJBPEQOKZKV-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-[2-methoxyethyl(propan-2-yl)amino]ethoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCCN(CCOC)C(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 FQAWJBPEQOKZKV-UHFFFAOYSA-N 0.000 claims 1
- YRPFIINFPFURQB-UHFFFAOYSA-N n-cyclopropyl-3-[6-[3-(4-hydroxypiperidin-1-yl)propoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCCN1CCC(O)CC1 YRPFIINFPFURQB-UHFFFAOYSA-N 0.000 claims 1
- AIEXXVAQFFNMSW-UHFFFAOYSA-N n-cyclopropyl-3-[6-[3-(dimethylamino)-2-methylpropoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCC(C)CN(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 AIEXXVAQFFNMSW-UHFFFAOYSA-N 0.000 claims 1
- PTHMAPUKXHBKAQ-UHFFFAOYSA-N n-cyclopropyl-3-[6-[3-(dimethylamino)prop-1-ynyl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(C#CCN(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 PTHMAPUKXHBKAQ-UHFFFAOYSA-N 0.000 claims 1
- HUPOHVVZLQCIHD-UHFFFAOYSA-N n-cyclopropyl-3-[6-[3-(dimethylamino)propoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCCCN(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 HUPOHVVZLQCIHD-UHFFFAOYSA-N 0.000 claims 1
- MOOJSSXTRRYSSV-UHFFFAOYSA-N n-cyclopropyl-3-[6-[3-(dimethylamino)propyl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(CCCN(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 MOOJSSXTRRYSSV-UHFFFAOYSA-N 0.000 claims 1
- NAPWLNDHTWMGDU-HXUWFJFHSA-N n-cyclopropyl-3-[6-[3-[(3r)-3-hydroxypyrrolidin-1-yl]propoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCCN1CC[C@@H](O)C1 NAPWLNDHTWMGDU-HXUWFJFHSA-N 0.000 claims 1
- DCTLMKOJXVEGLY-UHFFFAOYSA-N n-cyclopropyl-3-[6-[3-[2-methoxyethyl(methyl)amino]propoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(OCCCN(C)CCOC)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 DCTLMKOJXVEGLY-UHFFFAOYSA-N 0.000 claims 1
- LZBUHCGCJAQJSK-UHFFFAOYSA-N n-cyclopropyl-3-[6-[3-[furan-3-ylmethyl(methyl)amino]propoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1=COC=C1CN(C)CCCOC(C=C1C2=O)=CC=C1N=CN2C(C(=CC=1)C)=CC=1C(=O)NC1CC1 LZBUHCGCJAQJSK-UHFFFAOYSA-N 0.000 claims 1
- UYAJLWQZRUSGFX-UHFFFAOYSA-N n-cyclopropyl-3-[6-[4-(2,2-difluoroethyl)piperazin-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CCN(CC(F)F)CC1 UYAJLWQZRUSGFX-UHFFFAOYSA-N 0.000 claims 1
- BZJHTYFLENHXOG-UHFFFAOYSA-N n-cyclopropyl-3-[6-[4-(2-ethoxyethyl)piperazin-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(CCOCC)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 BZJHTYFLENHXOG-UHFFFAOYSA-N 0.000 claims 1
- MWTWUHRLTPWZKJ-UHFFFAOYSA-N n-cyclopropyl-3-[6-[4-(2-fluoroethyl)piperazin-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N1CCN(CCF)CC1 MWTWUHRLTPWZKJ-UHFFFAOYSA-N 0.000 claims 1
- UHYQZJQHXRIRLA-UHFFFAOYSA-N n-cyclopropyl-3-[6-[4-(2-methoxyethyl)-1,4-diazepan-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(CCOC)CCCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 UHYQZJQHXRIRLA-UHFFFAOYSA-N 0.000 claims 1
- LPSJUPVADXIZEL-UHFFFAOYSA-N n-cyclopropyl-3-[6-[4-(cyclopropylmethyl)-1,4-diazepan-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N(CC1)CCCN1CC1CC1 LPSJUPVADXIZEL-UHFFFAOYSA-N 0.000 claims 1
- RDBLFXLOUSXOMI-UHFFFAOYSA-N n-cyclopropyl-3-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2N(CC1)CCN1CC1CC1 RDBLFXLOUSXOMI-UHFFFAOYSA-N 0.000 claims 1
- XQWFURUWHYNGHP-IBGZPJMESA-N n-cyclopropyl-3-[6-[[(2s)-1-(2-hydroxyacetyl)pyrrolidin-2-yl]methoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC[C@@H]1CCCN1C(=O)CO XQWFURUWHYNGHP-IBGZPJMESA-N 0.000 claims 1
- QPEFSEABPBXXRC-UHFFFAOYSA-N n-cyclopropyl-3-[7-[3-(dimethylamino)propoxy]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C=1C(OCCCN(C)C)=CC=C(C2=O)C=1N=CN2C(C(=CC=1)C)=CC=1C(=O)NC1CC1 QPEFSEABPBXXRC-UHFFFAOYSA-N 0.000 claims 1
- IJHTWCMNEATOKW-UHFFFAOYSA-N n-cyclopropyl-3-[7-fluoro-6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(C)CCN1C1=CC(C(N(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=N2)=O)=C2C=C1F IJHTWCMNEATOKW-UHFFFAOYSA-N 0.000 claims 1
- MCOWZHSLKWSKEH-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(4-oxopyrido[2,3-d]pyrimidin-3-yl)benzamide Chemical compound C1=C(N2C(C3=CC=CN=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 MCOWZHSLKWSKEH-UHFFFAOYSA-N 0.000 claims 1
- SOAHBBABXLMJLH-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-(4-oxoquinazolin-3-yl)benzamide Chemical compound C1=C(N2C(C3=CC=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 SOAHBBABXLMJLH-UHFFFAOYSA-N 0.000 claims 1
- OTDUFFFEGBCDJS-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(1,2,3,6-tetrahydropyridin-4-yl)quinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2C1=CCNCC1 OTDUFFFEGBCDJS-UHFFFAOYSA-N 0.000 claims 1
- XCYYMGHNWCHXJP-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(1-propan-2-ylpiperidin-4-yl)oxyquinazolin-3-yl]benzamide Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 XCYYMGHNWCHXJP-UHFFFAOYSA-N 0.000 claims 1
- VLGXXQVHZLRUHZ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(1-propan-2-ylpyrrolidin-3-yl)oxyquinazolin-3-yl]benzamide Chemical compound C1N(C(C)C)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 VLGXXQVHZLRUHZ-UHFFFAOYSA-N 0.000 claims 1
- BPJSFEFKWJGWQZ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(2-piperidin-1-ylethoxy)quinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1CCCCC1 BPJSFEFKWJGWQZ-UHFFFAOYSA-N 0.000 claims 1
- YFNXUYXKQNOZHH-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(3-thiomorpholin-4-ylpropoxy)quinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCCN1CCSCC1 YFNXUYXKQNOZHH-UHFFFAOYSA-N 0.000 claims 1
- LTEZBUKUKJFLGM-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-(4-propyl-1,4-diazepan-1-yl)quinazolin-3-yl]benzamide Chemical compound C1CN(CCC)CCCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 LTEZBUKUKJFLGM-UHFFFAOYSA-N 0.000 claims 1
- VLGXXQVHZLRUHZ-OAQYLSRUSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-[(3r)-1-propan-2-ylpyrrolidin-3-yl]oxyquinazolin-3-yl]benzamide Chemical compound C1N(C(C)C)CC[C@H]1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 VLGXXQVHZLRUHZ-OAQYLSRUSA-N 0.000 claims 1
- HBCJIPTVFWQTKZ-GOSISDBHSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-[(3r)-pyrrolidin-3-yl]oxyquinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2O[C@@H]1CCNC1 HBCJIPTVFWQTKZ-GOSISDBHSA-N 0.000 claims 1
- VLGXXQVHZLRUHZ-NRFANRHFSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-[(3s)-1-propan-2-ylpyrrolidin-3-yl]oxyquinazolin-3-yl]benzamide Chemical compound C1N(C(C)C)CC[C@@H]1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 VLGXXQVHZLRUHZ-NRFANRHFSA-N 0.000 claims 1
- HBCJIPTVFWQTKZ-SFHVURJKSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-[(3s)-pyrrolidin-3-yl]oxyquinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2O[C@H]1CCNC1 HBCJIPTVFWQTKZ-SFHVURJKSA-N 0.000 claims 1
- LLRVCGMBTPAADF-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-[2-(4-propan-2-ylpiperazin-1-yl)ethoxy]quinazolin-3-yl]benzamide Chemical compound C1CN(C(C)C)CCN1CCOC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 LLRVCGMBTPAADF-UHFFFAOYSA-N 0.000 claims 1
- SYOFKBZUDVYPMI-GOSISDBHSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-[[(2r)-pyrrolidin-2-yl]methoxy]quinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC[C@H]1CCCN1 SYOFKBZUDVYPMI-GOSISDBHSA-N 0.000 claims 1
- SYOFKBZUDVYPMI-SFHVURJKSA-N n-cyclopropyl-4-methyl-3-[4-oxo-6-[[(2s)-pyrrolidin-2-yl]methoxy]quinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OC[C@@H]1CCCN1 SYOFKBZUDVYPMI-SFHVURJKSA-N 0.000 claims 1
- JKJWTTZRIOTRFG-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[6-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-4-oxoquinazolin-3-yl]benzamide Chemical compound C1N(C)CCC(C=2C=C3C(=O)N(C=4C(=CC=C(C=4)C(=O)NC4CC4)C)C=NC3=CC=2)=C1 JKJWTTZRIOTRFG-UHFFFAOYSA-N 0.000 claims 1
- FBMVCNHYMNJXAY-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[6-(1-methylpiperidin-4-yl)-4-oxoquinazolin-3-yl]benzamide Chemical compound C1CN(C)CCC1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 FBMVCNHYMNJXAY-UHFFFAOYSA-N 0.000 claims 1
- ABUCQWIMRCIACF-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[6-(1-methylpyrrolidin-3-yl)oxy-4-oxoquinazolin-3-yl]benzamide Chemical compound C1N(C)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 ABUCQWIMRCIACF-UHFFFAOYSA-N 0.000 claims 1
- VFLHHNVMMXWEIN-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[6-(2-methylpropoxy)-4-oxoquinazolin-3-yl]benzamide Chemical compound O=C1C2=CC(OCC(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 VFLHHNVMMXWEIN-UHFFFAOYSA-N 0.000 claims 1
- GBJMTGFASGSXMF-LJQANCHMSA-N n-cyclopropyl-4-methyl-3-[6-[(3r)-3-methyl-4-propan-2-ylpiperazin-1-yl]-4-oxoquinazolin-3-yl]benzamide Chemical compound C1[C@@H](C)N(C(C)C)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 GBJMTGFASGSXMF-LJQANCHMSA-N 0.000 claims 1
- YCEUSQOBFTYJBM-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[6-[2-(1,4-oxazepan-4-yl)ethoxy]-4-oxoquinazolin-3-yl]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1N(C(C1=C2)=O)C=NC1=CC=C2OCCN1CCCOCC1 YCEUSQOBFTYJBM-UHFFFAOYSA-N 0.000 claims 1
- LSDZMJLGZRWFCP-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[6-[2-[methyl(propan-2-yl)amino]ethoxy]-4-oxoquinazolin-3-yl]benzamide Chemical compound O=C1C2=CC(OCCN(C)C(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 LSDZMJLGZRWFCP-UHFFFAOYSA-N 0.000 claims 1
- NBEPQTPCNUXMLE-LJQANCHMSA-N n-cyclopropyl-4-methyl-3-[6-[[(2r)-1-methylpyrrolidin-2-yl]methoxy]-4-oxoquinazolin-3-yl]benzamide Chemical compound CN1CCC[C@@H]1COC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 NBEPQTPCNUXMLE-LJQANCHMSA-N 0.000 claims 1
- NBEPQTPCNUXMLE-IBGZPJMESA-N n-cyclopropyl-4-methyl-3-[6-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]-4-oxoquinazolin-3-yl]benzamide Chemical compound CN1CCC[C@H]1COC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 NBEPQTPCNUXMLE-IBGZPJMESA-N 0.000 claims 1
- RTQVLYIEJIWJSW-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[7-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3-yl]benzamide Chemical compound C1CN(C)CCN1C1=CC=C2C(=O)N(C=3C(=CC=C(C=3)C(=O)NC3CC3)C)C=NC2=C1 RTQVLYIEJIWJSW-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- FQJRZOYTUCCBQR-UHFFFAOYSA-N tert-butyl 2-methylheptanoate Chemical compound CCCCCC(C)C(=O)OC(C)(C)C FQJRZOYTUCCBQR-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 125000002757 morpholinyl group Chemical group 0.000 description 5
- 125000004193 piperazinyl group Chemical group 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 4
- 125000005053 dihydropyrimidinyl group Chemical group N1(CN=CC=C1)* 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000003701 inert diluent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 2
- 240000001812 Hyssopus officinalis Species 0.000 description 2
- 241001024304 Mino Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0324790.5A GB0324790D0 (en) | 2003-10-24 | 2003-10-24 | Amide derivatives |
| GB0324790.5 | 2003-10-24 | ||
| PCT/GB2004/004474 WO2005042502A1 (en) | 2003-10-24 | 2004-10-22 | Amide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007509118A JP2007509118A (ja) | 2007-04-12 |
| JP2007509118A5 true JP2007509118A5 (https=) | 2007-11-29 |
| JP4987478B2 JP4987478B2 (ja) | 2012-07-25 |
Family
ID=29595715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006536171A Expired - Fee Related JP4987478B2 (ja) | 2003-10-24 | 2004-10-22 | アミド誘導体 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US7750154B2 (https=) |
| EP (1) | EP1682520B1 (https=) |
| JP (1) | JP4987478B2 (https=) |
| KR (1) | KR101127697B1 (https=) |
| CN (2) | CN103012376A (https=) |
| AR (1) | AR046308A1 (https=) |
| AT (1) | ATE499347T1 (https=) |
| AU (1) | AU2004285749B2 (https=) |
| BR (1) | BRPI0415746A (https=) |
| CA (1) | CA2543351C (https=) |
| DE (1) | DE602004031543D1 (https=) |
| ES (1) | ES2359409T3 (https=) |
| GB (1) | GB0324790D0 (https=) |
| IL (1) | IL175065A (https=) |
| IS (1) | IS8450A (https=) |
| MX (1) | MXPA06004465A (https=) |
| MY (1) | MY140729A (https=) |
| NO (1) | NO20062370L (https=) |
| NZ (1) | NZ547095A (https=) |
| RU (1) | RU2375352C2 (https=) |
| SA (1) | SA04250351B1 (https=) |
| SG (1) | SG147409A1 (https=) |
| TW (1) | TWI343378B (https=) |
| UA (1) | UA83867C2 (https=) |
| UY (1) | UY28578A1 (https=) |
| WO (1) | WO2005042502A1 (https=) |
| ZA (1) | ZA200603226B (https=) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2260007C2 (ru) | 1999-03-17 | 2005-09-10 | Астразенека Аб | Производные амида, способ их получения (варианты), фармацевтическая композиция, способ ингибирования |
| GB0329572D0 (en) | 2003-12-20 | 2004-01-28 | Astrazeneca Ab | Amide derivatives |
| US20050261278A1 (en) | 2004-05-21 | 2005-11-24 | Weiner David M | Selective serotonin receptor inverse agonists as therapeutics for disease |
| NZ555974A (en) * | 2005-01-10 | 2010-11-26 | Acadia Pharm Inc | Aminophenyl derivatives as selective androgen receptor modulators |
| GB0504019D0 (en) * | 2005-02-26 | 2005-04-06 | Astrazeneca Ab | Amide derivatives |
| GB0516570D0 (en) * | 2005-08-12 | 2005-09-21 | Astrazeneca Ab | Amide derivatives |
| JP2009541310A (ja) * | 2006-06-19 | 2009-11-26 | アストラゼネカ・アクチエボラーグ | イソキノリン誘導体およびサイトカイン仲介疾患の阻害剤としてのそれらの使用 |
| GB0702456D0 (en) | 2007-02-08 | 2007-03-21 | Astrazeneca Ab | New combination |
| KR101791757B1 (ko) * | 2007-03-20 | 2017-10-30 | 셀진 코포레이션 | 4'-ｏ-치환된 아이소인돌린 유도체 및 이를 포함하는 조성물 및 이의 사용 방법 |
| US8354417B2 (en) * | 2007-09-26 | 2013-01-15 | Celgene Corporation | Solid forms comprising 3-(2,5-dimethyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione, compositions comprising the same, and methods of using the same |
| AU2008305581C1 (en) * | 2007-09-26 | 2014-12-11 | Celgene Corporation | 6-, 7-, or 8-substituted quinazolinone derivatives and compositions comprising and methods of using the same |
| JP2011503232A (ja) | 2007-11-20 | 2011-01-27 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッド | 免疫応答の調節 |
| WO2009138778A1 (en) * | 2008-05-12 | 2009-11-19 | Astrazeneca Ab | Cyclopropyl benzamide derivatives as intermediates for cytokine inhibitors |
| WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
| WO2011010131A1 (en) | 2009-07-21 | 2011-01-27 | Astrazeneca Ab | Compositions comprising an oxoisoquinoline methylbenzamide and a polymer |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| WO2011073662A1 (en) | 2009-12-17 | 2011-06-23 | Astrazeneca Ab | Combination of a benzoxazinone and a further agent for treating respiratory diseases |
| WO2011150198A1 (en) | 2010-05-27 | 2011-12-01 | Ambit Biosciences Corporation | Azolyl urea compounds and methods of use thereof |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| IN2014DN09346A (https=) | 2012-06-13 | 2015-07-17 | Hoffmann La Roche | |
| KR102179599B1 (ko) | 2012-09-25 | 2020-11-19 | 에프. 호프만-라 로슈 아게 | 이환형 유도체 |
| AR095079A1 (es) | 2013-03-12 | 2015-09-16 | Hoffmann La Roche | Derivados de octahidro-pirrolo[3,4-c]-pirrol y piridina-fenilo |
| CN105764905B (zh) | 2013-11-26 | 2019-06-07 | 豪夫迈·罗氏有限公司 | 新的八氢-环丁二烯并[1，2-c；3，4-c’]二吡咯-2基 |
| CN106103446B (zh) | 2014-03-26 | 2019-07-30 | 豪夫迈·罗氏有限公司 | 作为自分泌运动因子(atx)和溶血磷脂酸(lpa)生产抑制剂的二环化合物 |
| WO2015144609A1 (en) | 2014-03-26 | 2015-10-01 | F. Hoffmann-La Roche Ag | Condensed [1,4]diazepine compounds as autotaxin (atx) and lysophosphatidic acid (lpa) production inhibitors |
| JP6038212B2 (ja) * | 2015-03-18 | 2016-12-07 | ザ ガバメント オブ ザ ユナイテッド ステイツ オブ アメリカ アズ リプレゼンテッド バイ ザ セクレタリー オブ ザ デパートメント オブ ヘルス アンド ヒューマン サービシーズ | 甲状腺刺激ホルモン受容体（ｔｓｈｒ）の低分子量アゴニスト |
| CA2980730A1 (en) | 2015-03-23 | 2016-09-29 | The Brigham And Women's Hospital, Inc. | Tolerogenic nanoparticles for treating diabetes mellitus |
| MA41898A (fr) | 2015-04-10 | 2018-02-13 | Hoffmann La Roche | Dérivés de quinazolinone bicyclique |
| WO2017003723A1 (en) | 2015-07-01 | 2017-01-05 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| CA2992889A1 (en) | 2015-09-04 | 2017-03-09 | F. Hoffmann-La Roche Ag | Phenoxymethyl derivatives |
| KR20180054830A (ko) | 2015-09-24 | 2018-05-24 | 에프. 호프만-라 로슈 아게 | 오토탁신(atx) 억제제로서의 이환형 화합물 |
| AU2016328365B2 (en) | 2015-09-24 | 2020-04-23 | F. Hoffmann-La Roche Ag | New bicyclic compounds as dual ATX/CA inhibitors |
| CR20180057A (es) | 2015-09-24 | 2018-04-02 | Hoffmann La Roche | Nuevos compuestos biciclicos como inhibidores duales de atx/ca. |
| RU2018112230A (ru) | 2015-09-24 | 2019-10-30 | Ф. Хоффманн-Ля Рош Аг | Бициклические соединения в качестве ингибиторов atx |
| WO2018167113A1 (en) | 2017-03-16 | 2018-09-20 | F. Hoffmann-La Roche Ag | New bicyclic compounds as atx inhibitors |
| SG11201908560SA (en) | 2017-03-16 | 2019-10-30 | Hoffmann La Roche | Heterocyclic compounds useful as dual atx/ca inhibitors |
| CN106977500A (zh) * | 2017-04-17 | 2017-07-25 | 牡丹江医学院 | 一种用于治疗脑梗塞的药物及其制备方法 |
| US11028068B2 (en) | 2017-07-25 | 2021-06-08 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| MX2022012678A (es) * | 2020-04-08 | 2023-01-11 | Remix Therapeutics Inc | Compuestos y metodos para modular el corte y empalme. |
| JP7834721B2 (ja) | 2020-08-28 | 2026-03-24 | アルビナス・オペレーションズ・インコーポレイテッド | 急速進行性線維肉腫タンパク質分解化合物及び関連する使用方法 |
| EP4584258A1 (en) | 2022-09-07 | 2025-07-16 | Arvinas Operations, Inc. | Rapidly accelerated fibrosarcoma (raf) degrading compounds and associated methods of use |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1903899A (en) | 1933-04-18 | Cabboxylic acid abylides oe the benzene sebies and process oe making | ||
| DE522788C (de) | 1928-11-01 | 1931-04-15 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Carbonsaeurearyliden der Benzolreihe |
| US1909960A (en) | 1929-08-06 | 1933-05-23 | Du Pont | Intermediate for azo dyes |
| NL272900A (https=) | 1960-12-23 | |||
| US3755332A (en) | 1971-07-01 | 1973-08-28 | Ciba Geigy Corp | Substituted 4 indazolaminoquinolines |
| DE2812252A1 (de) | 1978-03-21 | 1979-10-04 | Bayer Ag | 1,2,4-triazol-blockierte polyisocyanate als vernetzer fuer lackbindemittel |
| US4367328A (en) | 1981-03-05 | 1983-01-04 | The Dow Chemical Company | Epoxy resins from hydroxy benzamides |
| US4524168A (en) | 1981-11-18 | 1985-06-18 | Ciba-Geigy Corporation | Process for the mass coloration of polymers |
| SU1396964A3 (ru) * | 1984-01-09 | 1988-05-15 | Жансен Фармасетика Н.В. (Фирма) | Способ получени 4-(бициклогетероциклилметил)пиперидинов или их фармацевтически приемлемых солей присоединени кислот |
| US4749729A (en) | 1984-06-21 | 1988-06-07 | American Cyanamid Company | Epoxy resin compositions curable above 160 F. and below 250 F. |
| JPS61204221A (ja) | 1985-03-07 | 1986-09-10 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物 |
| US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| WO1993004170A1 (en) | 1991-08-23 | 1993-03-04 | The United States Of America Represented By The Secretary, Department Of Health And Human Services | Raf protein kinase therapeutics |
| GB9816837D0 (en) | 1998-08-04 | 1998-09-30 | Zeneca Ltd | Amide derivatives |
| US7772432B2 (en) | 1991-09-19 | 2010-08-10 | Astrazeneca Ab | Amidobenzamide derivatives which are useful as cytokine inhibitors |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| GB9314884D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Tricyclic derivatives |
| IL112249A (en) | 1994-01-25 | 2001-11-25 | Warner Lambert Co | Pharmaceutical compositions containing di and tricyclic pyrimidine derivatives for inhibiting tyrosine kinases of the epidermal growth factor receptor family and some new such compounds |
| US5550132A (en) | 1994-06-22 | 1996-08-27 | University Of North Carolina | Hydroxyalkylammonium-pyrimidines or purines and nucleoside derivatives, useful as inhibitors of inflammatory cytokines |
| WO1997005878A1 (en) | 1995-08-10 | 1997-02-20 | Merck & Co., Inc. | 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use |
| DE69634822T2 (de) | 1995-08-22 | 2006-04-27 | Japan Tobacco Inc. | Amid-verbindungen und ihre anwendung |
| AR004010A1 (es) | 1995-10-11 | 1998-09-30 | Glaxo Group Ltd | Compuestos heterociclicos |
| GB9604926D0 (en) | 1996-03-08 | 1996-05-08 | Sandoz Ltd | Organic compounds |
| US6096748A (en) | 1996-03-13 | 2000-08-01 | Smithkline Beecham Corporation | Pyrimidine compounds useful in treating cytokine mediated diseases |
| EP0922042A1 (en) | 1996-08-09 | 1999-06-16 | Smithkline Beecham Corporation | Novel piperazine containing compounds |
| GB9623833D0 (en) | 1996-11-16 | 1997-01-08 | Zeneca Ltd | Chemical compound |
| WO1999001439A1 (en) | 1997-07-03 | 1999-01-14 | Du Pont Pharmaceuticals Company | Aryl-and arylamino-substituted heterocycles as corticotropin releasing hormone antagonists |
| ZA986732B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitiors of tyrosine kinases |
| AU739066B2 (en) | 1997-09-23 | 2001-10-04 | Astrazeneca Ab | Amide derivatives for the treatment of diseases mediated by cytokines |
| CZ299380B6 (cs) | 1998-03-27 | 2008-07-09 | Janssen Pharmaceutica N. V. | Pyrimidinová sloucenina, použití této slouceniny pro prípravu léciva, farmaceutický prostredek tutoslouceninu obsahující, zpusob prípravy tohoto prostredku a uvedené slouceniny a kombinace a produktuvedenou slouceninu obsahující |
| CA2328927C (en) | 1998-05-15 | 2008-02-19 | Astrazeneca Ab | Benzamide derivatives for the treatment of diseases mediated by cytokines |
| PT1077930E (pt) | 1998-05-15 | 2005-03-31 | Astrazeneca Ab | Derivados de benzamida para o tratamento de doencas mediadas por citocinas |
| CA2338121A1 (en) | 1998-08-04 | 2000-02-17 | Astrazeneca Ab | Amide derivatives useful as inhibitors of the production of cytokines |
| ES2221414T3 (es) | 1998-08-27 | 2004-12-16 | Sumitomo Pharmaceuticals Company, Limited | Derivados de pirimidina. |
| ES2274634T3 (es) | 1998-08-29 | 2007-05-16 | Astrazeneca Ab | Compuestos de pirimidina. |
| US6632820B1 (en) | 1998-08-29 | 2003-10-14 | Astrazeneca Ab | Pyrimidine compounds |
| EP1115707B1 (en) | 1998-09-25 | 2003-11-12 | AstraZeneca AB | Benzamide derivatives and ther use as cytokine inhibitors |
| ATE232205T1 (de) * | 1998-10-01 | 2003-02-15 | Astrazeneca Ab | Chinolin- und chinazolin derivate und ihre verwendung als inhibitoren von krankheiten, bei denen cytokine beteiligt wird |
| RU2260007C2 (ru) | 1999-03-17 | 2005-09-10 | Астразенека Аб | Производные амида, способ их получения (варианты), фармацевтическая композиция, способ ингибирования |
| AU761291B2 (en) | 1999-03-17 | 2003-05-29 | Astrazeneca Ab | Amide derivatives |
| GB9906566D0 (en) | 1999-03-23 | 1999-05-19 | Zeneca Ltd | Chemical compounds |
| GB9924092D0 (en) | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
| MXPA03005152A (es) * | 2000-12-11 | 2004-10-14 | Tularik Inc | Antogonista de cxcr3. |
| GB0124931D0 (en) * | 2001-10-17 | 2001-12-05 | Glaxo Group Ltd | Chemical compounds |
| TW200306839A (en) * | 2002-02-06 | 2003-12-01 | Novartis Ag | Quinazolinone derivatives and their use as CB agonists |
| EP2258687B1 (en) * | 2002-02-12 | 2012-12-26 | Glaxosmithkline LLC | Nicotinamide derivates useful as P38 inhibitors |
| US20060158474A1 (en) * | 2003-07-10 | 2006-07-20 | Van Dam Dirkjan B | Method and device for accurately positioning a pattern on a substrate |
| ATE482205T1 (de) * | 2003-07-25 | 2010-10-15 | Novartis Ag | P-38-kinasehemmer |
| GB0329572D0 (en) | 2003-12-20 | 2004-01-28 | Astrazeneca Ab | Amide derivatives |
| NZ555768A (en) | 2004-12-24 | 2009-12-24 | Astrazeneca Ab | Benzamide derivatives as inhibitors of cytokine mediated disease |
| GB0504019D0 (en) | 2005-02-26 | 2005-04-06 | Astrazeneca Ab | Amide derivatives |
| GB0516570D0 (en) | 2005-08-12 | 2005-09-21 | Astrazeneca Ab | Amide derivatives |
-
2003
- 2003-10-24 GB GBGB0324790.5A patent/GB0324790D0/en not_active Ceased
-
2004
- 2004-10-21 TW TW093132022A patent/TWI343378B/zh not_active IP Right Cessation
- 2004-10-22 UY UY28578A patent/UY28578A1/es not_active Application Discontinuation
- 2004-10-22 US US10/576,808 patent/US7750154B2/en not_active Expired - Fee Related
- 2004-10-22 EP EP04768990A patent/EP1682520B1/en not_active Expired - Lifetime
- 2004-10-22 CN CN2012103938753A patent/CN103012376A/zh active Pending
- 2004-10-22 AU AU2004285749A patent/AU2004285749B2/en not_active Ceased
- 2004-10-22 JP JP2006536171A patent/JP4987478B2/ja not_active Expired - Fee Related
- 2004-10-22 RU RU2006117326/04A patent/RU2375352C2/ru not_active IP Right Cessation
- 2004-10-22 KR KR1020067010003A patent/KR101127697B1/ko not_active Expired - Fee Related
- 2004-10-22 CA CA2543351A patent/CA2543351C/en not_active Expired - Fee Related
- 2004-10-22 DE DE602004031543T patent/DE602004031543D1/de not_active Expired - Lifetime
- 2004-10-22 ES ES04768990T patent/ES2359409T3/es not_active Expired - Lifetime
- 2004-10-22 AR ARP040103862A patent/AR046308A1/es not_active Application Discontinuation
- 2004-10-22 MX MXPA06004465A patent/MXPA06004465A/es active IP Right Grant
- 2004-10-22 CN CNA2004800390365A patent/CN1898216A/zh active Pending
- 2004-10-22 BR BRPI0415746-0A patent/BRPI0415746A/pt not_active IP Right Cessation
- 2004-10-22 MY MYPI20044370A patent/MY140729A/en unknown
- 2004-10-22 UA UAA200604496A patent/UA83867C2/ru unknown
- 2004-10-22 NZ NZ547095A patent/NZ547095A/en not_active IP Right Cessation
- 2004-10-22 SG SG200807338-9A patent/SG147409A1/en unknown
- 2004-10-22 WO PCT/GB2004/004474 patent/WO2005042502A1/en not_active Ceased
- 2004-10-22 AT AT04768990T patent/ATE499347T1/de not_active IP Right Cessation
- 2004-10-23 SA SA04250351A patent/SA04250351B1/ar unknown
-
2006
- 2006-04-20 IL IL175065A patent/IL175065A/en not_active IP Right Cessation
- 2006-04-21 ZA ZA200603226A patent/ZA200603226B/en unknown
- 2006-05-11 IS IS8450A patent/IS8450A/is unknown
- 2006-05-24 NO NO20062370A patent/NO20062370L/no not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2007509118A5 (https=) | ||
| RU2006117326A (ru) | Амидные производные | |
| US7442704B2 (en) | Amide derivatives | |
| US6432949B1 (en) | Amide derivatives useful as inhibitors of the production of cytokines | |
| KR101985050B1 (ko) | 피라진카르복사미드 화합물 | |
| US20030186966A1 (en) | Amide derivatives | |
| SK285520B6 (sk) | Amidové deriváty, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie na prípravu liečiva na liečbu stavov sprostredkovaných cytokínmi | |
| CA2382605A1 (en) | Pyrimidine derivatives | |
| WO2005082865A1 (ja) | 縮合二環性ピリミジン誘導体 | |
| JP2008501675A (ja) | Ｅｒｂｂ受容体型チロシンキナーゼとしてのキナゾリン誘導体 | |
| US20090036474A1 (en) | Quinazoline derivatives for use against cancer | |
| HK1041885B (en) | Amide derivatives | |
| ZA200106857B (en) | Amide derivatives. | |
| MXPA01009308A (en) | Amide derivatives | |
| CZ20011093A3 (cs) | Amidové deriváty, které jsou užitečné jako inhibitory produkce cytokinů, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje |