DE10150517A1 - Verwendung von Phosphodiesterase IV-Inhibitoren - Google Patents

Info

Publication number

DE10150517A1

DE10150517A1 DE10150517A DE10150517A DE10150517A1 DE 10150517 A1 DE10150517 A1 DE 10150517A1 DE 10150517 A DE10150517 A DE 10150517A DE 10150517 A DE10150517 A DE 10150517A DE 10150517 A1 DE10150517 A1 DE 10150517A1

Authority

DE

Germany

Prior art keywords

ethyl

dihydro

benzyl

dimethoxyphenyl

methoxyphenyl

Prior art date

2001-10-12

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.)

Withdrawn

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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 25
• 238000011282 treatment Methods 0.000 title claims abstract description 21
• 201000006417 multiple sclerosis Diseases 0.000 title claims abstract description 14
• 206010039073 rheumatoid arthritis Diseases 0.000 title claims abstract description 14
• 208000001132 Osteoporosis Diseases 0.000 title claims abstract description 13
• 201000001320 Atherosclerosis Diseases 0.000 title claims abstract description 9
• 239000003814 drug Substances 0.000 title claims description 16
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title 1
• QQSGDKKFXBGYON-UHFFFAOYSA-N ethoxy-methylperoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane Chemical class CCOP(=S)(OOC)OC1=CC(C)=NC(C(C)C)=N1 QQSGDKKFXBGYON-UHFFFAOYSA-N 0.000 title 1
• -1 phenyl-substituted 2,3,4,5-tetrahydro-pyridazin-3-one Chemical class 0.000 claims abstract description 317
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
• 150000003839 salts Chemical class 0.000 claims abstract description 14
• 208000030507 AIDS Diseases 0.000 claims abstract description 13
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 12
• 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 11
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 11
• 206010027476 Metastases Diseases 0.000 claims abstract description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 9
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
• 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 8
• 125000002252 acyl group Chemical group 0.000 claims abstract description 7
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
• 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 3
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 52
• 150000001875 compounds Chemical class 0.000 claims description 49
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 18
• 238000004519 manufacturing process Methods 0.000 claims description 15
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• LEURGHMXWSUXTF-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC(F)F)C(OC)=CC(C=2CSC(=O)NN=2)=C1 LEURGHMXWSUXTF-UHFFFAOYSA-N 0.000 claims description 5
• KQUGNOYYBNPZBP-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC(F)F)C(OC)=C1 KQUGNOYYBNPZBP-UHFFFAOYSA-N 0.000 claims description 5
• NIHJXZMNNAHEEV-UHFFFAOYSA-N ethyl n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OC)=CC=2)=N1 NIHJXZMNNAHEEV-UHFFFAOYSA-N 0.000 claims description 5
• VZVHHKYHUMMCRW-UHFFFAOYSA-N methyl n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 VZVHHKYHUMMCRW-UHFFFAOYSA-N 0.000 claims description 5
• YYLMPPQOOUHPPJ-UHFFFAOYSA-N n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC(NC(C)=O)=C1 YYLMPPQOOUHPPJ-UHFFFAOYSA-N 0.000 claims description 5
• FCEFLSGAPFCWGS-UHFFFAOYSA-N n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC(NS(C)(=O)=O)=C1 FCEFLSGAPFCWGS-UHFFFAOYSA-N 0.000 claims description 5
• XDGXAZPROPKMKW-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2,2-trifluoroacetamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(F)(F)F)C=C1 XDGXAZPROPKMKW-UHFFFAOYSA-N 0.000 claims description 5
• YMAJLELSVNAWDQ-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OC)=CC=2)=N1 YMAJLELSVNAWDQ-UHFFFAOYSA-N 0.000 claims description 5
• ZUIQPDPVTCODLP-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 ZUIQPDPVTCODLP-UHFFFAOYSA-N 0.000 claims description 5
• NZUBMTQQNISIDZ-UHFFFAOYSA-N n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 NZUBMTQQNISIDZ-UHFFFAOYSA-N 0.000 claims description 5
• UZFKGQZERPKMQX-UHFFFAOYSA-N n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)C1=CC=NC=C1 UZFKGQZERPKMQX-UHFFFAOYSA-N 0.000 claims description 5
• BCINSFUJSPEZRI-UHFFFAOYSA-N n-[4-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)OC(=O)N1CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 BCINSFUJSPEZRI-UHFFFAOYSA-N 0.000 claims description 5
• JEHXGPPOGAKEIP-UHFFFAOYSA-N n-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]-phenylmethyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1C(C=1C=CC=CC=1)NC(=O)C1=CC=NC=C1 JEHXGPPOGAKEIP-UHFFFAOYSA-N 0.000 claims description 5
• MWJLPJRBACIIEQ-UHFFFAOYSA-N n-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]-phenylmethyl]pyridine-4-carboxamide Chemical compound CCC1SC(=O)N(C(NC(=O)C=2C=CN=CC=2)C=2C=CC=CC=2)N=C1C1=CC=C(OC)C(OC)=C1 MWJLPJRBACIIEQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
• 230000006907 apoptotic process Effects 0.000 claims description 4
• RQPOEGOXCVKURG-UHFFFAOYSA-N ethyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 RQPOEGOXCVKURG-UHFFFAOYSA-N 0.000 claims description 4
• 229940126601 medicinal product Drugs 0.000 claims description 4
• FGQYYCHKYIREFI-UHFFFAOYSA-N 3-[(2,6-dichlorophenyl)methyl]-5-(3,4-dimethoxyphenyl)-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=C(Cl)C=CC=C1Cl FGQYYCHKYIREFI-UHFFFAOYSA-N 0.000 claims description 3
• RCWFQIICHNGYHS-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-5-(3,4-dimethoxyphenyl)-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(N)C=C1 RCWFQIICHNGYHS-UHFFFAOYSA-N 0.000 claims description 3
• JPJFJTANAMGIFE-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-[(4-methoxyphenyl)methyl]-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(OC)C=C1 JPJFJTANAMGIFE-UHFFFAOYSA-N 0.000 claims description 3
• GWVPBGLOGIVWER-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-[(4-nitrophenyl)methyl]-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C([N+]([O-])=O)C=C1 GWVPBGLOGIVWER-UHFFFAOYSA-N 0.000 claims description 3
• BSZQDFRBNZBYMQ-UHFFFAOYSA-N n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2-(4-methylpiperazin-1-yl)acetamide Chemical compound COC1=CC=C(C=2CCC(=O)N(CC=3C=CC(NC(=O)CN4CCN(C)CC4)=CC=3)N=2)C=C1OC1CCCC1 BSZQDFRBNZBYMQ-UHFFFAOYSA-N 0.000 claims description 3
• OHPMMTQUBIIBQX-UHFFFAOYSA-N n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)CN4CCN(C)CC4)=CC=3)N=2)=C1 OHPMMTQUBIIBQX-UHFFFAOYSA-N 0.000 claims description 3
• VULAEEDZQSJNRT-UHFFFAOYSA-N n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=C(NC(C)=O)C=C1 VULAEEDZQSJNRT-UHFFFAOYSA-N 0.000 claims description 3
• HTZVRAPOLYURTG-UHFFFAOYSA-N n-[4-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2,2,2-trifluoroacetamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)C(F)(F)F)C=C1 HTZVRAPOLYURTG-UHFFFAOYSA-N 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• 210000005260 human cell Anatomy 0.000 claims description 2
• 230000001613 neoplastic effect Effects 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 229920006395 saturated elastomer Polymers 0.000 claims 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 69
• 125000005843 halogen group Chemical group 0.000 abstract 6
• 125000006237 oxymethylenoxy group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 4
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 3
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
• 125000005842 heteroatom Chemical group 0.000 abstract 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
• 150000002148 esters Chemical class 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• CXGADTMFRPJNRF-UHFFFAOYSA-N [4-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6H-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamic acid Chemical compound COC=1C=C(C=CC=1OC)C1=NN(C(SC1CC)=O)CC1=CC=C(C=C1)NC(O)=O CXGADTMFRPJNRF-UHFFFAOYSA-N 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 5
• 239000012453 solvate Substances 0.000 description 5
• GUTBSANSYUYRAN-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-2-[(4-nitrophenyl)methyl]-4,5-dihydropyridazin-3-one Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=C([N+]([O-])=O)C=C1 GUTBSANSYUYRAN-UHFFFAOYSA-N 0.000 description 4
• XMIJMMGMQCHZLA-UHFFFAOYSA-N 6-chloro-n-[4-[2-[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]phenyl]pyridazine-3-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CCC(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)N=N1 XMIJMMGMQCHZLA-UHFFFAOYSA-N 0.000 description 4
• VRUMPENLSSRPKS-UHFFFAOYSA-N [4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamic acid Chemical compound C1(CCCC1)OC=1C=C(C=CC=1OC)C=1CCC(N(N=1)CC1=CC=C(C=C1)NC(O)=O)=O VRUMPENLSSRPKS-UHFFFAOYSA-N 0.000 description 4
• 201000011510 cancer Diseases 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 4
• MHQLCHXVPJLEKO-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC(NC(=O)C=2N=CNC=2)=C1 MHQLCHXVPJLEKO-UHFFFAOYSA-N 0.000 description 4
• HNKIVFWNYCJMMO-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 HNKIVFWNYCJMMO-UHFFFAOYSA-N 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 206010003210 Arteriosclerosis Diseases 0.000 description 3
• 208000023275 Autoimmune disease Diseases 0.000 description 3
• 206010012438 Dermatitis atopic Diseases 0.000 description 3
• PSSQIJNVFYKCKK-UHFFFAOYSA-N [4-[[5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-2-oxo-6H-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamic acid Chemical compound C(C)OC=1C=C(C=CC=1OC)C1=NN(C(SC1CC)=O)CC1=CC=C(C=C1)NC(O)=O PSSQIJNVFYKCKK-UHFFFAOYSA-N 0.000 description 3
• 208000006673 asthma Diseases 0.000 description 3
• 201000008937 atopic dermatitis Diseases 0.000 description 3
• 210000004027 cell Anatomy 0.000 description 3
• 201000010099 disease Diseases 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 125000004494 ethyl ester group Chemical group 0.000 description 3
• 230000002401 inhibitory effect Effects 0.000 description 3
• 238000000034 method Methods 0.000 description 3
• DSZXEXAFDZVTGT-UHFFFAOYSA-N n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2-dimethylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC(NC(=O)C(C)(C)C)=C1 DSZXEXAFDZVTGT-UHFFFAOYSA-N 0.000 description 3
• YCHIWCIRMQIQIQ-UHFFFAOYSA-N n-[3-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2-dimethylpropanamide Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC(NC(=O)C(C)(C)C)=C1 YCHIWCIRMQIQIQ-UHFFFAOYSA-N 0.000 description 3
• OJCARHSRJBWXPK-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2-dimethylpropanamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(C)(C)C)C=C1 OJCARHSRJBWXPK-UHFFFAOYSA-N 0.000 description 3
• DJFNEVLEQCTYRC-UHFFFAOYSA-N n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2-dimethylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=C(NC(=O)C(C)(C)C)C=C1 DJFNEVLEQCTYRC-UHFFFAOYSA-N 0.000 description 3
• NGBGHDLHCVJZGA-UHFFFAOYSA-N n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2-dimethylpropanamide Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(C)(C)C)C=C1 NGBGHDLHCVJZGA-UHFFFAOYSA-N 0.000 description 3
• JSINYLALQWCWRZ-UHFFFAOYSA-N n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,2-dimethylpropanamide Chemical compound COC1=CC=C(C=2CCC(=O)N(CC=3C=CC(NC(=O)C(C)(C)C)=CC=3)N=2)C=C1OC1CCCC1 JSINYLALQWCWRZ-UHFFFAOYSA-N 0.000 description 3
• NEXRJPBVDDLSLY-UHFFFAOYSA-N n-[4-[[6-ethyl-5-[3-(fluoromethoxy)-4-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)SC(=O)N1CC(C=C1)=CC=C1NC(=O)C1=CC=CN=C1 NEXRJPBVDDLSLY-UHFFFAOYSA-N 0.000 description 3
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 3
• ZDUJYDRBEZPFIM-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-n-[4-[[3-(4-methoxy-3-propan-2-yloxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]acetamide Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)CN1CCC(O)CC1 ZDUJYDRBEZPFIM-UHFFFAOYSA-N 0.000 description 2
• RCSOHJKSSBLBTL-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)-n-[4-[[3-(4-methoxy-3-propoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]acetamide Chemical compound C1=C(OC)C(OCCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)CN4CCC(O)CC4)=CC=3)N=2)=C1 RCSOHJKSSBLBTL-UHFFFAOYSA-N 0.000 description 2
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• CIZREEGOCQWNPD-UHFFFAOYSA-N [4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=C(NC(N)=O)C=C1 CIZREEGOCQWNPD-UHFFFAOYSA-N 0.000 description 2
• BVBMAKLIRDSMBS-UHFFFAOYSA-N [4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(N)=O)C=C1 BVBMAKLIRDSMBS-UHFFFAOYSA-N 0.000 description 2
• YOLXFGYYSSUXTQ-UHFFFAOYSA-N [4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound COC1=CC=C(C=2CCC(=O)N(CC=3C=CC(NC(N)=O)=CC=3)N=2)C=C1OC1CCCC1 YOLXFGYYSSUXTQ-UHFFFAOYSA-N 0.000 description 2
• ZJLPKCNSDCYJFI-UHFFFAOYSA-N [4-[[3-(3-ethoxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamic acid Chemical compound C(C)OC=1C=C(C=CC=1OC)C=1C(CC(N(N=1)CC1=CC=C(C=C1)NC(O)=O)=O)CC ZJLPKCNSDCYJFI-UHFFFAOYSA-N 0.000 description 2
• ONFVLRWCUFULEW-UHFFFAOYSA-N [4-[[3-(3-ethoxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound C1=C(OC)C(OCC)=CC(C=2C(CC(=O)N(CC=3C=CC(NC(N)=O)=CC=3)N=2)CC)=C1 ONFVLRWCUFULEW-UHFFFAOYSA-N 0.000 description 2
• YMFFBPIOIXNHKJ-UHFFFAOYSA-N [4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(N)=O)=CC=3)N=2)=C1 YMFFBPIOIXNHKJ-UHFFFAOYSA-N 0.000 description 2
• GXIJWQYTEMJDJB-UHFFFAOYSA-N [4-[[3-[3-(difluoromethoxy)-4-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(N)=O)C=C1 GXIJWQYTEMJDJB-UHFFFAOYSA-N 0.000 description 2
• FXNIOZTXWRGXKV-UHFFFAOYSA-N [4-[[3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamic acid Chemical compound FCOC=1C=C(C=CC=1OC)C=1CCC(N(N=1)CC1=CC=C(C=C1)NC(O)=O)=O FXNIOZTXWRGXKV-UHFFFAOYSA-N 0.000 description 2
• MUYYUWXZOICQLT-UHFFFAOYSA-N [4-[[3-[4-(difluoromethoxy)-3-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(N)=O)C=C1 MUYYUWXZOICQLT-UHFFFAOYSA-N 0.000 description 2
• COJHOKXVQOBJIF-UHFFFAOYSA-N [4-[[4-ethyl-3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(N)=O)C=C1 COJHOKXVQOBJIF-UHFFFAOYSA-N 0.000 description 2
• LPLQYKYLYGJNAL-UHFFFAOYSA-N [4-[[4-ethyl-3-[3-methoxy-4-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC)C(OC(F)(F)F)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(N)=O)C=C1 LPLQYKYLYGJNAL-UHFFFAOYSA-N 0.000 description 2
• CDVLZUINIYBNKE-UHFFFAOYSA-N [4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(N)=O)C=C1 CDVLZUINIYBNKE-UHFFFAOYSA-N 0.000 description 2
• ZCDJAPCKHRMEMK-UHFFFAOYSA-N [4-[[4-ethyl-3-[4-methoxy-3-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(N)=O)C=C1 ZCDJAPCKHRMEMK-UHFFFAOYSA-N 0.000 description 2
• XVQAIPBAXIMBHB-UHFFFAOYSA-N [4-[[5-(3-ethoxy-4-methoxyphenyl)-2-oxo-6H-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamic acid Chemical compound C(C)OC=1C=C(C=CC=1OC)C1=NN(C(SC1)=O)CC1=CC=C(C=C1)NC(O)=O XVQAIPBAXIMBHB-UHFFFAOYSA-N 0.000 description 2
• 239000008186 active pharmaceutical agent Substances 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
• URBLGKZUXYOKEX-UHFFFAOYSA-N ethyl n-[3-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(CN2C(CC(CC)C(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 URBLGKZUXYOKEX-UHFFFAOYSA-N 0.000 description 2
• SFZRRCZVQQMRJY-UHFFFAOYSA-N ethyl n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(CN2C(CCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 SFZRRCZVQQMRJY-UHFFFAOYSA-N 0.000 description 2
• XVAVKPRGWLAJPM-UHFFFAOYSA-N ethyl n-[3-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(CN2C(CC(CC)C(=N2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=O)=C1 XVAVKPRGWLAJPM-UHFFFAOYSA-N 0.000 description 2
• GCTGMPXZEYVMKM-UHFFFAOYSA-N ethyl n-[4-[2-[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CCN1C(=O)CC(CC)C(C=2C=C(OC)C(OC)=CC=2)=N1 GCTGMPXZEYVMKM-UHFFFAOYSA-N 0.000 description 2
• ARSIANLVWYUQBF-UHFFFAOYSA-N ethyl n-[4-[2-[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CCN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 ARSIANLVWYUQBF-UHFFFAOYSA-N 0.000 description 2
• SSIBZUDDTFSNAO-UHFFFAOYSA-N ethyl n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC3CCCC3)C(OC)=CC=2)=N1 SSIBZUDDTFSNAO-UHFFFAOYSA-N 0.000 description 2
• ZQIUHVHFDUIYQD-UHFFFAOYSA-N ethyl n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CCC(C=2C=C(OC3CCCC3)C(OC)=CC=2)=N1 ZQIUHVHFDUIYQD-UHFFFAOYSA-N 0.000 description 2
• QVWKBVPRCSKSIE-UHFFFAOYSA-N ethyl n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OCC)C(OC)=CC=2)=N1 QVWKBVPRCSKSIE-UHFFFAOYSA-N 0.000 description 2
• SDKPDXHJQJYWBK-UHFFFAOYSA-N ethyl n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CCC(C=2C=C(OCC)C(OC)=CC=2)=N1 SDKPDXHJQJYWBK-UHFFFAOYSA-N 0.000 description 2
• BDMQCZIGYDYBBE-UHFFFAOYSA-N ethyl n-[4-[[3-[3-(difluoromethoxy)-4-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC(F)F)C(OC)=CC=2)=N1 BDMQCZIGYDYBBE-UHFFFAOYSA-N 0.000 description 2
• LIUJINWHPPBRJU-UHFFFAOYSA-N ethyl n-[4-[[3-[4-(difluoromethoxy)-3-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OC(F)F)=CC=2)=N1 LIUJINWHPPBRJU-UHFFFAOYSA-N 0.000 description 2
• WABGJDMYOUPEKJ-UHFFFAOYSA-N ethyl n-[4-[[4-ethyl-3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OCF)C(OC)=CC=2)=N1 WABGJDMYOUPEKJ-UHFFFAOYSA-N 0.000 description 2
• DOKWENINAQJBTQ-UHFFFAOYSA-N ethyl n-[4-[[4-ethyl-3-[3-methoxy-4-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OC(F)(F)F)=CC=2)=N1 DOKWENINAQJBTQ-UHFFFAOYSA-N 0.000 description 2
• QHAWILCTEYTIAR-UHFFFAOYSA-N ethyl n-[4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC)C(OCF)=CC=2)=N1 QHAWILCTEYTIAR-UHFFFAOYSA-N 0.000 description 2
• RDQXPJUVTBTRER-UHFFFAOYSA-N ethyl n-[4-[[4-ethyl-3-[4-methoxy-3-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)CC(CC)C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)=N1 RDQXPJUVTBTRER-UHFFFAOYSA-N 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• 208000027866 inflammatory disease Diseases 0.000 description 2
• 230000005764 inhibitory process Effects 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• YWPDKNOLKSLTLB-UHFFFAOYSA-N methyl 2-[3-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC(NC(=O)C(=O)OC)=C1 YWPDKNOLKSLTLB-UHFFFAOYSA-N 0.000 description 2
• KXSOQZRWQCSFJG-UHFFFAOYSA-N methyl 2-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound COC(=O)C(=O)NC1=CC=CC(CN2C(CCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 KXSOQZRWQCSFJG-UHFFFAOYSA-N 0.000 description 2
• QXMPDRNZOKHCDA-UHFFFAOYSA-N methyl 2-[3-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC(NC(=O)C(=O)OC)=C1 QXMPDRNZOKHCDA-UHFFFAOYSA-N 0.000 description 2
• OUPGIHQDRGFOQM-UHFFFAOYSA-N methyl 2-[4-[2-[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CCC1=CC=C(NC(=O)C(=O)OC)C=C1 OUPGIHQDRGFOQM-UHFFFAOYSA-N 0.000 description 2
• GVAAJIYLDBOALI-UHFFFAOYSA-N methyl 2-[4-[2-[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CCN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 GVAAJIYLDBOALI-UHFFFAOYSA-N 0.000 description 2
• WNXOKRJNHQBTDQ-UHFFFAOYSA-N methyl 2-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 WNXOKRJNHQBTDQ-UHFFFAOYSA-N 0.000 description 2
• HVQLONHFPXVKGM-UHFFFAOYSA-N methyl 2-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 HVQLONHFPXVKGM-UHFFFAOYSA-N 0.000 description 2
• PZZOMTVBAIJTSM-UHFFFAOYSA-N methyl 2-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 PZZOMTVBAIJTSM-UHFFFAOYSA-N 0.000 description 2
• PNAAXTXDAXPPCR-UHFFFAOYSA-N methyl 2-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CN1C(=O)CCC(C=2C=C(OC3CCCC3)C(OC)=CC=2)=N1 PNAAXTXDAXPPCR-UHFFFAOYSA-N 0.000 description 2
• ZUTDQPMRVIUTPA-UHFFFAOYSA-N methyl 2-[4-[[3-(3-ethoxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=C(OC)C(OCC)=CC(C=2C(CC(=O)N(CC=3C=CC(NC(=O)C(=O)OC)=CC=3)N=2)CC)=C1 ZUTDQPMRVIUTPA-UHFFFAOYSA-N 0.000 description 2
• MTACDBARDPRQMY-UHFFFAOYSA-N methyl 2-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)C(=O)OC)=CC=3)N=2)=C1 MTACDBARDPRQMY-UHFFFAOYSA-N 0.000 description 2
• DRNAKASZNADFQV-UHFFFAOYSA-N methyl 2-[4-[[3-[3-(difluoromethoxy)-4-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 DRNAKASZNADFQV-UHFFFAOYSA-N 0.000 description 2
• UQHNVTCKSFRTDI-UHFFFAOYSA-N methyl 2-[4-[[3-[4-(difluoromethoxy)-3-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 UQHNVTCKSFRTDI-UHFFFAOYSA-N 0.000 description 2
• ZUIHGOLCNVKKKR-UHFFFAOYSA-N methyl 2-[4-[[4-ethyl-3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 ZUIHGOLCNVKKKR-UHFFFAOYSA-N 0.000 description 2
• POAZMKKVOWSGND-UHFFFAOYSA-N methyl 2-[4-[[4-ethyl-3-[3-methoxy-4-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC)C(OC(F)(F)F)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 POAZMKKVOWSGND-UHFFFAOYSA-N 0.000 description 2
• IWVUUKXMZFMIRB-UHFFFAOYSA-N methyl 2-[4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 IWVUUKXMZFMIRB-UHFFFAOYSA-N 0.000 description 2
• ZKWVJXUKPDWNJJ-UHFFFAOYSA-N methyl 2-[4-[[4-ethyl-3-[4-methoxy-3-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 ZKWVJXUKPDWNJJ-UHFFFAOYSA-N 0.000 description 2
• AAVSBRVGOGNZDK-UHFFFAOYSA-N methyl n-[3-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC(NC(=O)OC)=C1 AAVSBRVGOGNZDK-UHFFFAOYSA-N 0.000 description 2
• QVGFXSAKMWSHSR-UHFFFAOYSA-N methyl n-[3-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(CN2C(CCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 QVGFXSAKMWSHSR-UHFFFAOYSA-N 0.000 description 2
• WOHSIJFDZKWNRL-UHFFFAOYSA-N methyl n-[3-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC(NC(=O)OC)=C1 WOHSIJFDZKWNRL-UHFFFAOYSA-N 0.000 description 2
• IGVUZYDRMGFKFD-UHFFFAOYSA-N methyl n-[4-[2-[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CCC1=CC=C(NC(=O)OC)C=C1 IGVUZYDRMGFKFD-UHFFFAOYSA-N 0.000 description 2
• FONCJTUPQGDYCT-UHFFFAOYSA-N methyl n-[4-[2-[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1CCN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 FONCJTUPQGDYCT-UHFFFAOYSA-N 0.000 description 2
• HSEWOFPHGBRPMD-UHFFFAOYSA-N methyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 HSEWOFPHGBRPMD-UHFFFAOYSA-N 0.000 description 2
• QOMQZZYHFYONCG-UHFFFAOYSA-N methyl n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 QOMQZZYHFYONCG-UHFFFAOYSA-N 0.000 description 2
• JCNUKBBYWVDZTM-UHFFFAOYSA-N methyl n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1CN1C(=O)CCC(C=2C=C(OC3CCCC3)C(OC)=CC=2)=N1 JCNUKBBYWVDZTM-UHFFFAOYSA-N 0.000 description 2
• GNIQXHKTYKZEEI-UHFFFAOYSA-N methyl n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2C(CC(=O)N(CC=3C=CC(NC(=O)OC)=CC=3)N=2)CC)=C1 GNIQXHKTYKZEEI-UHFFFAOYSA-N 0.000 description 2
• NDOUMDUYIWPXOX-UHFFFAOYSA-N methyl n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)OC)=CC=3)N=2)=C1 NDOUMDUYIWPXOX-UHFFFAOYSA-N 0.000 description 2
• FNFJFNYSSGZYGV-UHFFFAOYSA-N methyl n-[4-[[3-[3-(difluoromethoxy)-4-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 FNFJFNYSSGZYGV-UHFFFAOYSA-N 0.000 description 2
• OCCVKBRWWJHYBW-UHFFFAOYSA-N methyl n-[4-[[3-[4-(difluoromethoxy)-3-methoxyphenyl]-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 OCCVKBRWWJHYBW-UHFFFAOYSA-N 0.000 description 2
• WGCOJCYYPSQGGN-UHFFFAOYSA-N methyl n-[4-[[4-ethyl-3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 WGCOJCYYPSQGGN-UHFFFAOYSA-N 0.000 description 2
• UXPKUOTZZJNOBG-UHFFFAOYSA-N methyl n-[4-[[4-ethyl-3-[3-methoxy-4-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC(F)(F)F)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 UXPKUOTZZJNOBG-UHFFFAOYSA-N 0.000 description 2
• SVKHSLUYEANZCF-UHFFFAOYSA-N methyl n-[4-[[4-ethyl-3-[4-(fluoromethoxy)-3-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 SVKHSLUYEANZCF-UHFFFAOYSA-N 0.000 description 2
• WSWIJVFPBWPGLH-UHFFFAOYSA-N methyl n-[4-[[4-ethyl-3-[4-methoxy-3-(trifluoromethoxy)phenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 WSWIJVFPBWPGLH-UHFFFAOYSA-N 0.000 description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• PKWYHHBCGBVQQT-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CC=NO1 PKWYHHBCGBVQQT-UHFFFAOYSA-N 0.000 description 2
• KFMYVLMJISCKNM-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1,3-oxazole-5-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CN=CO1 KFMYVLMJISCKNM-UHFFFAOYSA-N 0.000 description 2
• UIIGGQCDCOFTMC-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CNC=N1 UIIGGQCDCOFTMC-UHFFFAOYSA-N 0.000 description 2
• OTIXJVDUVJCHIM-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1h-pyrazole-5-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C=1C=CNN=1 OTIXJVDUVJCHIM-UHFFFAOYSA-N 0.000 description 2
• KPEZGGNLLNZMQM-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1h-pyrrole-2-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CC=CN1 KPEZGGNLLNZMQM-UHFFFAOYSA-N 0.000 description 2
• DPDQGSZMEJXVGV-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C=1SC(C)=NC=1C DPDQGSZMEJXVGV-UHFFFAOYSA-N 0.000 description 2
• CGVROIUYQJFQFB-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]furan-2-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CC=CO1 CGVROIUYQJFQFB-UHFFFAOYSA-N 0.000 description 2
• WXBXENDYUZBAQF-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyrazine-2-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CN=CC=N1 WXBXENDYUZBAQF-UHFFFAOYSA-N 0.000 description 2
• BNSCCCSCMKTSTI-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CC=CN=C1 BNSCCCSCMKTSTI-UHFFFAOYSA-N 0.000 description 2
• ZNHBGFZBALEVPZ-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyridine-4-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=CC=NC=C1 ZNHBGFZBALEVPZ-UHFFFAOYSA-N 0.000 description 2
• UKHYXPBUHKEBTE-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyrimidine-2-carboxamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=CC=C1NC(=O)C1=NC=CC=N1 UKHYXPBUHKEBTE-UHFFFAOYSA-N 0.000 description 2
• JNEVLEUKNUVSGY-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=NO1 JNEVLEUKNUVSGY-UHFFFAOYSA-N 0.000 description 2
• ZHLSDPJNUPVQSH-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1,3-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CN=CO1 ZHLSDPJNUPVQSH-UHFFFAOYSA-N 0.000 description 2
• LXPLZSNSOHWPEJ-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CNC=N1 LXPLZSNSOHWPEJ-UHFFFAOYSA-N 0.000 description 2
• RWMSJJZJJWTXQO-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1h-pyrazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=NNC=C1 RWMSJJZJJWTXQO-UHFFFAOYSA-N 0.000 description 2
• IEGMIKIJXYKRMK-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-1h-pyrrole-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CN1 IEGMIKIJXYKRMK-UHFFFAOYSA-N 0.000 description 2
• RAVOWHFURQATIO-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=C(C)N=C(C)S1 RAVOWHFURQATIO-UHFFFAOYSA-N 0.000 description 2
• KNUWNCARQUDUSF-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CN=CC=N1 KNUWNCARQUDUSF-UHFFFAOYSA-N 0.000 description 2
• CELNHASYKXCXKP-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CN=C1 CELNHASYKXCXKP-UHFFFAOYSA-N 0.000 description 2
• JQHWYZJURZMSOU-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=NC=C1 JQHWYZJURZMSOU-UHFFFAOYSA-N 0.000 description 2
• DQDNKBXVHLYWLV-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=NC=CC=N1 DQDNKBXVHLYWLV-UHFFFAOYSA-N 0.000 description 2
• NUPLGGQAVYINCT-UHFFFAOYSA-N n-[2-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CS1 NUPLGGQAVYINCT-UHFFFAOYSA-N 0.000 description 2
• XQMIZNNNMJMDAA-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=NO1 XQMIZNNNMJMDAA-UHFFFAOYSA-N 0.000 description 2
• YOOXXZHJWDELIH-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]-1,3-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CN=CO1 YOOXXZHJWDELIH-UHFFFAOYSA-N 0.000 description 2
• WQMIGCSMOIEWDT-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CNC=N1 WQMIGCSMOIEWDT-UHFFFAOYSA-N 0.000 description 2
• GXQMBBGDPAFHKI-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]-1h-pyrazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=NNC=C1 GXQMBBGDPAFHKI-UHFFFAOYSA-N 0.000 description 2
• BNPJBDCOGRBFIK-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]-1h-pyrrole-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CN1 BNPJBDCOGRBFIK-UHFFFAOYSA-N 0.000 description 2
• VLZUNGZBTVRMFF-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=C(C)N=C(C)S1 VLZUNGZBTVRMFF-UHFFFAOYSA-N 0.000 description 2
• FYVOGAWSQZDUOF-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CO1 FYVOGAWSQZDUOF-UHFFFAOYSA-N 0.000 description 2
• ODVFUBRBUJKWIR-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]pyrazine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CN=CC=N1 ODVFUBRBUJKWIR-UHFFFAOYSA-N 0.000 description 2
• DXMISARGCHGSGA-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]pyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CN=C1 DXMISARGCHGSGA-UHFFFAOYSA-N 0.000 description 2
• WCYBOQPXIPPKBR-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]pyridine-4-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=NC=C1 WCYBOQPXIPPKBR-UHFFFAOYSA-N 0.000 description 2
• QBBXRMFWQOYQPL-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]pyrimidine-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=NC=CC=N1 QBBXRMFWQOYQPL-UHFFFAOYSA-N 0.000 description 2
• RZGBLNMMHKOPMF-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-oxadiazin-3-yl]methyl]phenyl]thiophene-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(COC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CS1 RZGBLNMMHKOPMF-UHFFFAOYSA-N 0.000 description 2
• MAGMCYQGBISBIH-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=NO1 MAGMCYQGBISBIH-UHFFFAOYSA-N 0.000 description 2
• YDMZUQAYNNFPCY-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-1,3-oxazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CN=CO1 YDMZUQAYNNFPCY-UHFFFAOYSA-N 0.000 description 2
• CTQIVWZACHOFOH-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-1h-imidazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CNC=N1 CTQIVWZACHOFOH-UHFFFAOYSA-N 0.000 description 2
• JUZWSKOCRMKYIV-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-1h-pyrazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=NNC=C1 JUZWSKOCRMKYIV-UHFFFAOYSA-N 0.000 description 2
• YUNBPAIKCYBBLS-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-1h-pyrrole-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CN1 YUNBPAIKCYBBLS-UHFFFAOYSA-N 0.000 description 2
• NAQTUAIBAHFIKL-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=C(C)N=C(C)S1 NAQTUAIBAHFIKL-UHFFFAOYSA-N 0.000 description 2
• KQLJNTWTQHAONW-UHFFFAOYSA-N n-[2-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]furan-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC=C1NC(=O)C1=CC=CO1 KQLJNTWTQHAONW-UHFFFAOYSA-N 0.000 description 2
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• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
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• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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• JSBPMNLLDMYAHR-UHFFFAOYSA-N 2-piperazin-1-ylethyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCNCC1 JSBPMNLLDMYAHR-UHFFFAOYSA-N 0.000 description 1
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• NVCVZPKFQQXCEV-UHFFFAOYSA-N 2-piperazin-1-ylethyl n-[4-[[5-(3-ethoxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CSC(=O)N(CC=3C=CC(NC(=O)OCCN4CCNCC4)=CC=3)N=2)=C1 NVCVZPKFQQXCEV-UHFFFAOYSA-N 0.000 description 1
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• RMUBXQFMFWGKCT-UHFFFAOYSA-N 2-piperazin-1-ylethyl n-[4-[[5-(4-methoxy-3-propan-2-yloxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCNCC1 RMUBXQFMFWGKCT-UHFFFAOYSA-N 0.000 description 1
• MAOVERXALZBYLP-UHFFFAOYSA-N 2-piperazin-1-ylethyl n-[4-[[5-(4-methoxy-3-propoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCCC)=CC(C=2CSC(=O)N(CC=3C=CC(NC(=O)OCCN4CCNCC4)=CC=3)N=2)=C1 MAOVERXALZBYLP-UHFFFAOYSA-N 0.000 description 1
• ZFZSBQCQBRHPBP-UHFFFAOYSA-N 2-piperazin-1-ylethyl n-[4-[[5-[3-(fluoromethoxy)-4-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OCF)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCNCC1 ZFZSBQCQBRHPBP-UHFFFAOYSA-N 0.000 description 1
• BDUVPKPFEFBMQD-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl carbamate Chemical compound NC(=O)OCCN1CCCC1 BDUVPKPFEFBMQD-UHFFFAOYSA-N 0.000 description 1
• IMSDIMQLQSVHTE-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC(NC(=O)OCCN2CCCC2)=C1 IMSDIMQLQSVHTE-UHFFFAOYSA-N 0.000 description 1
• NGPYHZHZLVFONV-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC(C=C1)=CC=C1NC(=O)OCCN1CCCC1 NGPYHZHZLVFONV-UHFFFAOYSA-N 0.000 description 1
• WHAMIXVHSWUIDR-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCCC1 WHAMIXVHSWUIDR-UHFFFAOYSA-N 0.000 description 1
• HOYNLXWHTIYQSC-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound COC1=CC=C(C=2CCC(=O)N(CC=3C=CC(NC(=O)OCCN4CCCC4)=CC=3)N=2)C=C1OC1CCCC1 HOYNLXWHTIYQSC-UHFFFAOYSA-N 0.000 description 1
• DKDBYXIIXCMSTJ-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)OCCN4CCCC4)=CC=3)N=2)=C1 DKDBYXIIXCMSTJ-UHFFFAOYSA-N 0.000 description 1
• UPWMETQWHWEXPP-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[3-(4-methoxy-3-propan-2-yloxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCCC1 UPWMETQWHWEXPP-UHFFFAOYSA-N 0.000 description 1
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• QWKOJRKDNSMTBB-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCCC1 QWKOJRKDNSMTBB-UHFFFAOYSA-N 0.000 description 1
• LNDFBFMDRHPAJY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC(C=C1)=CC=C1NC(=O)OCCN1CCCC1 LNDFBFMDRHPAJY-UHFFFAOYSA-N 0.000 description 1
• DKDPHSHWHSHOHM-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[5-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound COC1=CC=C(C=2CSC(=O)N(CC=3C=CC(NC(=O)OCCN4CCCC4)=CC=3)N=2)C=C1OC1CCCC1 DKDPHSHWHSHOHM-UHFFFAOYSA-N 0.000 description 1
• BOMXHVCIJCNWMO-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[5-(3-ethoxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CSC(=O)N(CC=3C=CC(NC(=O)OCCN4CCCC4)=CC=3)N=2)=C1 BOMXHVCIJCNWMO-UHFFFAOYSA-N 0.000 description 1
• VESRLQPYXNZQQM-UHFFFAOYSA-N 2-pyrrolidin-1-ylethyl n-[4-[[5-(4-methoxy-3-propan-2-yloxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCCC1 VESRLQPYXNZQQM-UHFFFAOYSA-N 0.000 description 1
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• FSXQGGWBDWTVKV-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 FSXQGGWBDWTVKV-UHFFFAOYSA-N 0.000 description 1
• YOQPXPJHXQFXCW-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 YOQPXPJHXQFXCW-UHFFFAOYSA-N 0.000 description 1
• PEJAKJIJVKYKDF-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound COC1=CC=C(C=2CCC(=O)N(CC=3C=CC(NC(=O)OCCN4CCSCC4)=CC=3)N=2)C=C1OC1CCCC1 PEJAKJIJVKYKDF-UHFFFAOYSA-N 0.000 description 1
• DZZNBQPHVHISAC-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)OCCN4CCSCC4)=CC=3)N=2)=C1 DZZNBQPHVHISAC-UHFFFAOYSA-N 0.000 description 1
• XJMBBFWFTVNPFR-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[3-(4-methoxy-3-propan-2-yloxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 XJMBBFWFTVNPFR-UHFFFAOYSA-N 0.000 description 1
• QAOCVIHAHBGRPE-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[3-(4-methoxy-3-propoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)OCCN4CCSCC4)=CC=3)N=2)=C1 QAOCVIHAHBGRPE-UHFFFAOYSA-N 0.000 description 1
• FZJFJMSNPDKJMH-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OCF)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 FZJFJMSNPDKJMH-UHFFFAOYSA-N 0.000 description 1
• RARVQIIJYQGERR-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 RARVQIIJYQGERR-UHFFFAOYSA-N 0.000 description 1
• SOJOECZSPXWFGW-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 SOJOECZSPXWFGW-UHFFFAOYSA-N 0.000 description 1
• GUCWJUXSDPZUCM-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound COC1=CC=C(C=2CSC(=O)N(CC=3C=CC(NC(=O)OCCN4CCSCC4)=CC=3)N=2)C=C1OC1CCCC1 GUCWJUXSDPZUCM-UHFFFAOYSA-N 0.000 description 1
• SSOWTOBVZHXTHU-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-(3-ethoxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2CSC(=O)N(CC=3C=CC(NC(=O)OCCN4CCSCC4)=CC=3)N=2)=C1 SSOWTOBVZHXTHU-UHFFFAOYSA-N 0.000 description 1
• KFVJCGUCUNJRPP-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCC)=CC(C=2C(SC(=O)N(CC=3C=CC(NC(=O)OCCN4CCSCC4)=CC=3)N=2)CC)=C1 KFVJCGUCUNJRPP-UHFFFAOYSA-N 0.000 description 1
• LVEFSWSZMSNRJU-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-(4-methoxy-3-propan-2-yloxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 LVEFSWSZMSNRJU-UHFFFAOYSA-N 0.000 description 1
• IUCPDKXEIDRWEP-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-(4-methoxy-3-propoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCCC)=CC(C=2CSC(=O)N(CC=3C=CC(NC(=O)OCCN4CCSCC4)=CC=3)N=2)=C1 IUCPDKXEIDRWEP-UHFFFAOYSA-N 0.000 description 1
• DXQFJMQSXUUAOB-UHFFFAOYSA-N 2-thiomorpholin-4-ylethyl n-[4-[[5-[3-(fluoromethoxy)-4-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=C(OCF)C(OC)=CC=C1C(CSC1=O)=NN1CC(C=C1)=CC=C1NC(=O)OCCN1CCSCC1 DXQFJMQSXUUAOB-UHFFFAOYSA-N 0.000 description 1
• LPVPITJSBXSDHT-UHFFFAOYSA-N 3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound O=C1NN=CCS1 LPVPITJSBXSDHT-UHFFFAOYSA-N 0.000 description 1
• WBOYNTJOPSFCAM-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-6H-1,3,4-thiadiazin-2-one Chemical compound COC=1C=C(C=CC1OC)N1C(SCC=N1)=O WBOYNTJOPSFCAM-UHFFFAOYSA-N 0.000 description 1
• YYUHVYIQWMPNGV-UHFFFAOYSA-N 3-(4-hydroxypiperidin-1-yl)-n-[4-[[3-(4-methoxy-3-propan-2-yloxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CCC1=O)=NN1CC(C=C1)=CC=C1NC(=O)CCN1CCC(O)CC1 YYUHVYIQWMPNGV-UHFFFAOYSA-N 0.000 description 1
• LOJGTMJPXPTJNG-UHFFFAOYSA-N 3-(4-hydroxypiperidin-1-yl)-n-[4-[[3-(4-methoxy-3-propoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=C(OC)C(OCCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)CCN4CCC(O)CC4)=CC=3)N=2)=C1 LOJGTMJPXPTJNG-UHFFFAOYSA-N 0.000 description 1
• OKONQTXUMFAFIW-UHFFFAOYSA-N 3-(diethylamino)-n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CCN(CC)CC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 OKONQTXUMFAFIW-UHFFFAOYSA-N 0.000 description 1
• RTYMIQFVKOMXFF-UHFFFAOYSA-N 3-(diethylamino)-n-[4-[[3-(4-methoxy-3-propan-2-yloxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=CC(NC(=O)CCN(CC)CC)=CC=C1CN1C(=O)CCC(C=2C=C(OC(C)C)C(OC)=CC=2)=N1 RTYMIQFVKOMXFF-UHFFFAOYSA-N 0.000 description 1
• PHHLGTFDVKZBDX-UHFFFAOYSA-N 3-(diethylamino)-n-[4-[[3-(4-methoxy-3-propoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=C(OC)C(OCCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)CCN(CC)CC)=CC=3)N=2)=C1 PHHLGTFDVKZBDX-UHFFFAOYSA-N 0.000 description 1
• AAWXRLLMTHQRJQ-UHFFFAOYSA-N 3-(diethylamino)propyl n-[4-[[3-(3,4-dimethoxyphenyl)-4-ethyl-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)CC(=O)N1CC1=CC=C(NC(=O)OCCCN(CC)CC)C=C1 AAWXRLLMTHQRJQ-UHFFFAOYSA-N 0.000 description 1
• WFNKSKHELDIREW-UHFFFAOYSA-N 3-(diethylamino)propyl n-[4-[[3-(3,4-dimethoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCN(CC)CC)=CC=C1CN1C(=O)CCC(C=2C=C(OC)C(OC)=CC=2)=N1 WFNKSKHELDIREW-UHFFFAOYSA-N 0.000 description 1
• OEACQCBKMHUOFZ-UHFFFAOYSA-N 3-(diethylamino)propyl n-[4-[[3-(4-methoxy-3-propan-2-yloxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCN(CC)CC)=CC=C1CN1C(=O)CCC(C=2C=C(OC(C)C)C(OC)=CC=2)=N1 OEACQCBKMHUOFZ-UHFFFAOYSA-N 0.000 description 1
• JDJAPECEESXCCQ-UHFFFAOYSA-N 3-(diethylamino)propyl n-[4-[[3-(4-methoxy-3-propoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=C(OC)C(OCCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)OCCCN(CC)CC)=CC=3)N=2)=C1 JDJAPECEESXCCQ-UHFFFAOYSA-N 0.000 description 1
• NOESHBZFWGYJRO-UHFFFAOYSA-N 3-(diethylamino)propyl n-[4-[[3-[3-(fluoromethoxy)-4-methoxyphenyl]-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCN(CC)CC)=CC=C1CN1C(=O)CCC(C=2C=C(OCF)C(OC)=CC=2)=N1 NOESHBZFWGYJRO-UHFFFAOYSA-N 0.000 description 1
• MISUAAMOAOEREL-UHFFFAOYSA-N 3-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-6H-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(N=C1)c1ccc(OC(F)F)c(OC)c1 MISUAAMOAOEREL-UHFFFAOYSA-N 0.000 description 1
• LBZOVRPNHSDSSN-UHFFFAOYSA-N 3-[di(propan-2-yl)amino]-n-[4-[[3-(3-ethoxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)CCN(C(C)C)C(C)C)=CC=3)N=2)=C1 LBZOVRPNHSDSSN-UHFFFAOYSA-N 0.000 description 1
• AVZBRMOJQZSKCG-UHFFFAOYSA-N 3-[di(propan-2-yl)amino]-n-[4-[[3-(4-methoxy-3-propan-2-yloxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=C(OC(C)C)C(OC)=CC=C1C(CCC1=O)=NN1CC1=CC=C(NC(=O)CCN(C(C)C)C(C)C)C=C1 AVZBRMOJQZSKCG-UHFFFAOYSA-N 0.000 description 1
• MMEMVPWMNMEICE-UHFFFAOYSA-N 3-[di(propan-2-yl)amino]-n-[4-[[3-(4-methoxy-3-propoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]propanamide Chemical compound C1=C(OC)C(OCCC)=CC(C=2CCC(=O)N(CC=3C=CC(NC(=O)CCN(C(C)C)C(C)C)=CC=3)N=2)=C1 MMEMVPWMNMEICE-UHFFFAOYSA-N 0.000 description 1
• HMPNECFFDWDHNX-UHFFFAOYSA-N 3-morpholin-4-ylpropyl carbamate Chemical compound NC(=O)OCCCN1CCOCC1 HMPNECFFDWDHNX-UHFFFAOYSA-N 0.000 description 1
• ZAJBGVFQWPXLTR-UHFFFAOYSA-N 3-morpholin-4-ylpropyl n-[4-[[3-(3-cyclopentyloxy-4-methoxyphenyl)-6-oxo-4,5-dihydropyridazin-1-yl]methyl]phenyl]carbamate Chemical compound COC1=CC=C(C=2CCC(=O)N(CC=3C=CC(NC(=O)OCCCN4CCOCC4)=CC=3)N=2)C=C1OC1CCCC1 ZAJBGVFQWPXLTR-UHFFFAOYSA-N 0.000 description 1
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