JP2007509118A5 - - Google Patents
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- 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
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- 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
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-
2003
- 2003-10-24 GB GBGB0324790.5A patent/GB0324790D0/en not_active Ceased
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2004
- 2004-10-21 TW TW093132022A patent/TWI343378B/zh not_active IP Right Cessation
- 2004-10-22 BR BRPI0415746-0A patent/BRPI0415746A/pt not_active IP Right Cessation
- 2004-10-22 ES ES04768990T patent/ES2359409T3/es not_active Expired - Lifetime
- 2004-10-22 SG SG200807338-9A patent/SG147409A1/en unknown
- 2004-10-22 NZ NZ547095A patent/NZ547095A/en not_active IP Right Cessation
- 2004-10-22 DE DE602004031543T patent/DE602004031543D1/de not_active Expired - Lifetime
- 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 CN CNA2004800390365A patent/CN1898216A/zh active Pending
- 2004-10-22 UA UAA200604496A patent/UA83867C2/ru unknown
- 2004-10-22 AT AT04768990T patent/ATE499347T1/de not_active IP Right Cessation
- 2004-10-22 AU AU2004285749A patent/AU2004285749B2/en not_active Ceased
- 2004-10-22 MY MYPI20044370A patent/MY140729A/en unknown
- 2004-10-22 AR ARP040103862A patent/AR046308A1/es not_active Application Discontinuation
- 2004-10-22 CN CN2012103938753A patent/CN103012376A/zh active Pending
- 2004-10-22 CA CA2543351A patent/CA2543351C/en not_active Expired - Fee Related
- 2004-10-22 WO PCT/GB2004/004474 patent/WO2005042502A1/en not_active Ceased
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- 2004-10-22 UY UY28578A patent/UY28578A1/es not_active Application Discontinuation
- 2004-10-22 JP JP2006536171A patent/JP4987478B2/ja not_active Expired - Fee Related
- 2004-10-22 US US10/576,808 patent/US7750154B2/en not_active Expired - Fee Related
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