CA2460135C - Use of pyridazinone compounds as phosphodiesterase iv inhibitors for treating cancer and other diseases - Google Patents

Info

Publication number

CA2460135C

CA2460135C CA2460135A CA2460135A CA2460135C CA 2460135 C CA2460135 C CA 2460135C CA 2460135 A CA2460135 A CA 2460135A CA 2460135 A CA2460135 A CA 2460135A CA 2460135 C CA2460135 C CA 2460135C

Authority

CA

Canada

Prior art keywords

ethyl

dihydro

phenyl

thiadiazin

tetrahydropyridazin

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.)

Expired - Fee Related

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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 24
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title abstract description 6
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title abstract description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 6
• 201000011510 cancer Diseases 0.000 title description 5
• 201000010099 disease Diseases 0.000 title description 2
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title 1
• 239000003814 drug Substances 0.000 claims abstract description 25
• 238000011282 treatment Methods 0.000 claims abstract description 23
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• 208000030507 AIDS Diseases 0.000 claims abstract description 9
• 206010027476 Metastases Diseases 0.000 claims abstract description 9
• 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 9
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 8
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 6
• -1 methylenedioxy Chemical group 0.000 claims description 209
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 90
• 125000004432 carbon atom Chemical group C* 0.000 claims description 56
• 150000001875 compounds Chemical class 0.000 claims description 53
• 238000002360 preparation method Methods 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 208000025865 Ulcer Diseases 0.000 claims description 4
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• 230000006907 apoptotic process Effects 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
• 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 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 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 2
• 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 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
• 230000000711 cancerogenic effect Effects 0.000 claims description 2
• 231100000315 carcinogenic Toxicity 0.000 claims description 2
• 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 2
• 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 2
• 210000005260 human cell Anatomy 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 230000001613 neoplastic effect Effects 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 229920006395 saturated elastomer Polymers 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims 6
• 125000001153 fluoro group Chemical group F* 0.000 claims 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 2
• 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 2
• 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 claims 1
• LVPAIIZXYHTHPY-UHFFFAOYSA-N 3-(diethylamino)propyl 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)OCCCN(CC)CC)=CC=3)N=2)=C1 LVPAIIZXYHTHPY-UHFFFAOYSA-N 0.000 claims 1
• DTYIPKIMTNWGEC-UHFFFAOYSA-N 3-(diethylamino)propyl n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCN(CC)CC)=CC=C1CN1C(=O)SCC(C=2C=C(OC)C(OC)=CC=2)=N1 DTYIPKIMTNWGEC-UHFFFAOYSA-N 0.000 claims 1
• RMQUGLYTMSMYDN-UHFFFAOYSA-N 3-(diethylamino)propyl 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)OCCCN(CC)CC)=CC=3)N=2)=C1 RMQUGLYTMSMYDN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• BQYXNMFWPXOBHV-UHFFFAOYSA-N n-[4-[[5-(3-ethoxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2-(4-methylpiperazin-1-yl)acetamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CSC(=O)N(CC=3C=CC(NC(=O)CN4CCN(C)CC4)=CC=3)N=2)=C1 BQYXNMFWPXOBHV-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 230000001105 regulatory effect Effects 0.000 claims 1
• 206010009887 colitis Diseases 0.000 abstract 1
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 256
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 192
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 141
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 33
• 229940080818 propionamide Drugs 0.000 description 33
• 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 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• 125000004429 atom Chemical group 0.000 description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 239000012453 solvate Substances 0.000 description 5
• MJTFALHLZWUAGR-UHFFFAOYSA-N 2-ethyl-4,5-dihydropyridazin-3-one Chemical compound CCN1N=CCCC1=O MJTFALHLZWUAGR-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• 238000000034 method Methods 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
• TVPRCLHSULCNLV-UHFFFAOYSA-N pyridazin-3-one Chemical compound O=C1C=CC=N[N]1 TVPRCLHSULCNLV-UHFFFAOYSA-N 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 208000023275 Autoimmune disease Diseases 0.000 description 3
• 206010012438 Dermatitis atopic Diseases 0.000 description 3
• 239000004480 active ingredient Substances 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
• 230000005764 inhibitory process Effects 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 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 2
• 206010009900 Colitis ulcerative Diseases 0.000 description 2
• 201000004681 Psoriasis Diseases 0.000 description 2
• 102000018594 Tumour necrosis factor Human genes 0.000 description 2
• 108050007852 Tumour necrosis factor Proteins 0.000 description 2
• 201000006704 Ulcerative Colitis Diseases 0.000 description 2
• 150000001408 amides Chemical class 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 230000037396 body weight Effects 0.000 description 2
• 238000006243 chemical reaction Methods 0.000 description 2
• LYZCWDIVOAXKQP-UHFFFAOYSA-N diazinan-3-one Chemical compound O=C1CCCNN1 LYZCWDIVOAXKQP-UHFFFAOYSA-N 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 230000002401 inhibitory effect Effects 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 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 2
• 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 2
• 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 2
• 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 2
• 210000005170 neoplastic cell Anatomy 0.000 description 2
• 238000007911 parenteral administration Methods 0.000 description 2
• 239000000843 powder Substances 0.000 description 2
• 238000011321 prophylaxis Methods 0.000 description 2
• 230000025915 regulation of apoptotic process Effects 0.000 description 2
• 239000003826 tablet Substances 0.000 description 2
• URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
• MDLXFTCTDJAZIX-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 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)OC2CCN(C)CC2)=C1 MDLXFTCTDJAZIX-UHFFFAOYSA-N 0.000 description 1
• WTGUUGJZRZUIAU-UHFFFAOYSA-N 1,3,4-thiadiazin-2-one Chemical compound O=C1N=NC=CS1 WTGUUGJZRZUIAU-UHFFFAOYSA-N 0.000 description 1
• WPSXDPCDVIMCRA-UHFFFAOYSA-N 1-(dimethylamino)propan-2-yl 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)OC(C)CN(C)C)=CC=3)N=2)=C1 WPSXDPCDVIMCRA-UHFFFAOYSA-N 0.000 description 1
• CVLZLPUNEZALHN-UHFFFAOYSA-N 2-(4-hydroxypiperidin-1-yl)ethyl 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)OCCN1CCC(O)CC1 CVLZLPUNEZALHN-UHFFFAOYSA-N 0.000 description 1
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• 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 1
• 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 1
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• 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 1
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• 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 1
• 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 1
• 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 1
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical class [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
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• AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 239000011707 mineral Substances 0.000 description 1
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