NZ547095A - Amide derivatives - Google Patents
Amide derivativesInfo
- Publication number
- NZ547095A NZ547095A NZ547095A NZ54709504A NZ547095A NZ 547095 A NZ547095 A NZ 547095A NZ 547095 A NZ547095 A NZ 547095A NZ 54709504 A NZ54709504 A NZ 54709504A NZ 547095 A NZ547095 A NZ 547095A
- Authority
- NZ
- New Zealand
- Prior art keywords
- cyclopropyl
- alkyl
- oxoquinazolin
- methyl
- methylbenzamide
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 448
- 238000000034 method Methods 0.000 claims abstract description 133
- 125000005843 halogen group Chemical group 0.000 claims abstract description 69
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 37
- 102000004127 Cytokines Human genes 0.000 claims abstract description 36
- 108090000695 Cytokines Proteins 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 201000010099 disease Diseases 0.000 claims abstract description 28
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 230000001404 mediated effect Effects 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- -1 hydroxy, amino Chemical group 0.000 claims description 495
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 203
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 202
- 150000001875 compounds Chemical class 0.000 claims description 198
- 125000003545 alkoxy group Chemical group 0.000 claims description 177
- 125000001424 substituent group Chemical group 0.000 claims description 151
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 133
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 104
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 100
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 96
- 125000000623 heterocyclic group Chemical group 0.000 claims description 74
- 125000003282 alkyl amino group Chemical group 0.000 claims description 73
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 125000000304 alkynyl group Chemical group 0.000 claims description 48
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 48
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 30
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000001589 carboacyl group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
- 241001465754 Metazoa Species 0.000 claims description 24
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 23
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 23
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 21
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 19
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 18
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims description 17
- 241000282414 Homo sapiens Species 0.000 claims description 17
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 12
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- UHBGYFCCKRAEHA-UHFFFAOYSA-N p-methylbenzamide Natural products CC1=CC=C(C(N)=O)C=C1 UHBGYFCCKRAEHA-UHFFFAOYSA-N 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 8
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 206010040070 Septic Shock Diseases 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 6
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 6
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
- 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 6
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 6
- 208000030507 AIDS Diseases 0.000 claims description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 125000005997 bromomethyl group Chemical group 0.000 claims description 6
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 6
- 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 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 208000031225 myocardial ischemia Diseases 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- DBEHLIUEWIOLPL-UHFFFAOYSA-N 3-[6-(2-aminoethoxy)-4-oxoquinazolin-3-yl]-n-cyclopropyl-4-methylbenzamide Chemical compound C1=C(N2C(C3=CC(OCCN)=CC=C3N=C2)=O)C(C)=CC=C1C(=O)NC1CC1 DBEHLIUEWIOLPL-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- DLNIYYYDSDSZEI-UHFFFAOYSA-N 3-[6-[2-(dimethylamino)ethoxy]-4-oxoquinazolin-3-yl]-4-methyl-n-(1-methylcyclopropyl)benzamide Chemical compound O=C1C2=CC(OCCN(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1(C)CC1 DLNIYYYDSDSZEI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- DVALNBRRKYLKFD-UHFFFAOYSA-N 4-methyl-n-(1-methylcyclopropyl)-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)NC2(C)CC2)C)C2=O)C2=C1 DVALNBRRKYLKFD-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 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 description 2
- HCPMOUXUWOUFKH-UHFFFAOYSA-N n-cyclobutyl-4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3-yl]benzamide Chemical compound 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
- OIGAZBWYYOZDQO-UHFFFAOYSA-N n-cyclopentyl-4-methyl-3-[6-(4-methylpiperazin-1-yl)-4-oxoquinazolin-3-yl]benzamide Chemical compound C1CN(C)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CCCC2)C)C2=O)C2=C1 OIGAZBWYYOZDQO-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- XHFABWPTYFWNFH-UHFFFAOYSA-N n-cyclopropyl-3-[6-(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=C2N1CCCNCC1 XHFABWPTYFWNFH-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- QEFHZJKGTOSAJE-UHFFFAOYSA-N n-cyclopropyl-3-[6-(1-ethylpiperidin-4-yl)oxy-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(CC)CCC1OC1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 QEFHZJKGTOSAJE-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- XNWNDXYGRNNCLL-UHFFFAOYSA-N n-cyclopropyl-3-[6-(4-ethylpiperazin-1-yl)-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound C1CN(CC)CCN1C1=CC=C(N=CN(C=2C(=CC=C(C=2)C(=O)NC2CC2)C)C2=O)C2=C1 XNWNDXYGRNNCLL-UHFFFAOYSA-N 0.000 claims description 2
- PNEXVVGLXCTFKG-JOCHJYFZSA-N n-cyclopropyl-3-[6-[(3r)-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-JOCHJYFZSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- AASYFHMMZAMLBQ-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-(4,4-difluoropiperidin-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(F)(F)CC1 AASYFHMMZAMLBQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- KWTUGOJIMMRZGR-UHFFFAOYSA-N n-cyclopropyl-3-[6-[2-(dimethylamino)ethylsulfanyl]-4-oxoquinazolin-3-yl]-4-methylbenzamide Chemical compound O=C1C2=CC(SCCN(C)C)=CC=C2N=CN1C(C(=CC=1)C)=CC=1C(=O)NC1CC1 KWTUGOJIMMRZGR-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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| KR20180053408A (ko) | 2015-09-24 | 2018-05-21 | 에프. 호프만-라 로슈 아게 | 이중 오토탁신(atx)/탄산 무수화효소(ca) 억제제로서의 신규한 이환형 화합물 |
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2003
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