SK281052B6 - Derivát arylalkyltiadiazinónu, spôsob jeho prípravy, farmaceutický prostriedok, ktorý ho obsahuje a použitie - Google Patents

Info

Publication number

SK281052B6

SK281052B6 SK123-96A SK12396A SK281052B6 SK 281052 B6 SK281052 B6 SK 281052B6 SK 12396 A SK12396 A SK 12396A SK 281052 B6 SK281052 B6 SK 281052B6

Authority

SK

Slovakia

Prior art keywords

dihydro

thiadiazin

ethyl

chloride

dimethoxyphenyl

Prior art date

1995-01-28

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
• 238000002360 preparation method Methods 0.000 title abstract description 6
• 238000000034 method Methods 0.000 title description 10
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
• -1 -OA Chemical group 0.000 claims description 145
• 150000001875 compounds Chemical class 0.000 claims description 45
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 239000002253 acid Substances 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 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
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
• 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 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
• 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 2
• 125000002252 acyl group Chemical group 0.000 claims description 2
• 230000002152 alkylating effect Effects 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 230000003301 hydrolyzing effect Effects 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 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
• 239000003814 drug Substances 0.000 abstract description 7
• 208000006673 asthma Diseases 0.000 abstract description 5
• 239000000543 intermediate Substances 0.000 abstract description 4
• 230000005764 inhibitory process Effects 0.000 abstract description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
• 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
• 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
• 125000001153 fluoro group Chemical group F* 0.000 abstract 1
• 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 23
• 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 description 19
• 239000000243 solution Substances 0.000 description 19
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 18
• 239000012346 acetyl chloride Substances 0.000 description 18
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 18
• PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 17
• SHMNLEQWIMKCQA-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl chloride Chemical compound FC(F)(F)C(F)(F)C(Cl)=O SHMNLEQWIMKCQA-UHFFFAOYSA-N 0.000 description 16
• JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 16
• YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 16
• DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 16
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 16
• DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 16
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 16
• YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 16
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 16
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 16
• XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• ZXUQEPZWVQIOJE-UHFFFAOYSA-N methyl 2-chloro-2-oxoacetate Chemical compound COC(=O)C(Cl)=O ZXUQEPZWVQIOJE-UHFFFAOYSA-N 0.000 description 14
• WEPUZBYKXNKSDH-UHFFFAOYSA-N cyclopentanecarbonyl chloride Chemical compound ClC(=O)C1CCCC1 WEPUZBYKXNKSDH-UHFFFAOYSA-N 0.000 description 13
• LPVPITJSBXSDHT-UHFFFAOYSA-N 3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound O=C1NN=CCS1 LPVPITJSBXSDHT-UHFFFAOYSA-N 0.000 description 9
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 5
• 229940077388 benzenesulfonate Drugs 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 239000002775 capsule Substances 0.000 description 4
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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• 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 3
• 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 3
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• DARDYTBLZQDXBK-UHFFFAOYSA-N 1-(chloromethyl)-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CCl)C([N+]([O-])=O)=C1 DARDYTBLZQDXBK-UHFFFAOYSA-N 0.000 description 2
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• DNONNJVQPCLZAY-UHFFFAOYSA-N [4-[[5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(N)=O)C=C1 DNONNJVQPCLZAY-UHFFFAOYSA-N 0.000 description 1
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• OEMFTCSZEXJLGZ-UHFFFAOYSA-N [4-[[6-ethyl-5-[4-methoxy-3-(trifluoromethoxy)phenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]urea Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(N)=O)C=C1 OEMFTCSZEXJLGZ-UHFFFAOYSA-N 0.000 description 1
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• PDVCNWNGYMTHSB-UHFFFAOYSA-N ethyl n-[4-[2-[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CCN1C(=O)SCC(C=2C=C(OC)C(OC)=CC=2)=N1 PDVCNWNGYMTHSB-UHFFFAOYSA-N 0.000 description 1
• IYNRZHRZKOAMJK-UHFFFAOYSA-N ethyl n-[4-[2-[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CCN1C(=O)SC(CC)C(C=2C=C(OC)C(OC)=CC=2)=N1 IYNRZHRZKOAMJK-UHFFFAOYSA-N 0.000 description 1
• NQNKDBYPTRTJKQ-UHFFFAOYSA-N ethyl n-[4-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SC(CC)C(C=2C=C(OC)C(OC)=CC=2)=N1 NQNKDBYPTRTJKQ-UHFFFAOYSA-N 0.000 description 1
• KKGDLLVJFZGJSX-UHFFFAOYSA-N ethyl n-[4-[[5-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SCC(C=2C=C(OC3CCCC3)C(OC)=CC=2)=N1 KKGDLLVJFZGJSX-UHFFFAOYSA-N 0.000 description 1
• LOCFYGNGBHHAII-UHFFFAOYSA-N ethyl n-[4-[[5-(3-ethoxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SCC(C=2C=C(OCC)C(OC)=CC=2)=N1 LOCFYGNGBHHAII-UHFFFAOYSA-N 0.000 description 1
• SBDGKFSPXWZJFR-UHFFFAOYSA-N ethyl n-[4-[[5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SC(CC)C(C=2C=C(OCC)C(OC)=CC=2)=N1 SBDGKFSPXWZJFR-UHFFFAOYSA-N 0.000 description 1
• BUGWSQKURORCIK-UHFFFAOYSA-N ethyl n-[4-[[5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SC(CC)C(C=2C=C(OC(F)F)C(OC)=CC=2)=N1 BUGWSQKURORCIK-UHFFFAOYSA-N 0.000 description 1
• QXRJGFCQPOUJHC-UHFFFAOYSA-N ethyl n-[4-[[5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SC(CC)C(C=2C=C(OC)C(OC(F)F)=CC=2)=N1 QXRJGFCQPOUJHC-UHFFFAOYSA-N 0.000 description 1
• ZXYMHFPNTLIZNZ-UHFFFAOYSA-N ethyl n-[4-[[6-ethyl-5-[3-(fluoromethoxy)-4-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SC(CC)C(C=2C=C(OCF)C(OC)=CC=2)=N1 ZXYMHFPNTLIZNZ-UHFFFAOYSA-N 0.000 description 1
• CKLMYPUTZWPVGP-UHFFFAOYSA-N ethyl n-[4-[[6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SC(CC)C(C=2C=C(OC)C(OCF)=CC=2)=N1 CKLMYPUTZWPVGP-UHFFFAOYSA-N 0.000 description 1
• PLLYTPACXDSARN-UHFFFAOYSA-N ethyl n-[4-[[6-ethyl-5-[4-methoxy-3-(trifluoromethoxy)phenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1CN1C(=O)SC(CC)C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)=N1 PLLYTPACXDSARN-UHFFFAOYSA-N 0.000 description 1
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• CIEOMWUGKBLMKY-UHFFFAOYSA-N hydrazinylmethyl formate Chemical compound NNCOC=O CIEOMWUGKBLMKY-UHFFFAOYSA-N 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
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• 208000027866 inflammatory disease Diseases 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
• AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
• 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
• GDMYAMPNMKKFAL-UHFFFAOYSA-N methyl 2-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]anilino]-2-oxoacetate Chemical compound COC(=O)C(=O)NC1=CC=CC(CN2C(SCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 GDMYAMPNMKKFAL-UHFFFAOYSA-N 0.000 description 1
• PSBVIBNYQUGGLF-UHFFFAOYSA-N methyl 2-[4-[2-[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]ethyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CCN1C(=O)SCC(C=2C=C(OC)C(OC)=CC=2)=N1 PSBVIBNYQUGGLF-UHFFFAOYSA-N 0.000 description 1
• ZQYITZRYMWJZSW-UHFFFAOYSA-N methyl 2-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]anilino]-2-oxoacetate Chemical compound C1=CC(NC(=O)C(=O)OC)=CC=C1CN1C(=O)SCC(C=2C=C(OC)C(OC)=CC=2)=N1 ZQYITZRYMWJZSW-UHFFFAOYSA-N 0.000 description 1
• WJXCJNWRNHTRKE-UHFFFAOYSA-N methyl 2-[4-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 WJXCJNWRNHTRKE-UHFFFAOYSA-N 0.000 description 1
• IPZLYSZQBOCTKB-UHFFFAOYSA-N methyl 2-[4-[[6-ethyl-5-[4-methoxy-3-(trifluoromethoxy)phenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]anilino]-2-oxoacetate Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)C(=O)OC)C=C1 IPZLYSZQBOCTKB-UHFFFAOYSA-N 0.000 description 1
• ZHRAHPSTKXDMGH-UHFFFAOYSA-N methyl n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(CN2C(SCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 ZHRAHPSTKXDMGH-UHFFFAOYSA-N 0.000 description 1
• WOOZPBIBIZOJPG-UHFFFAOYSA-N methyl n-[3-[[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)N1CC1=CC=CC(NC(=O)OC)=C1 WOOZPBIBIZOJPG-UHFFFAOYSA-N 0.000 description 1
• DXGNHPZDEQJFQH-UHFFFAOYSA-N methyl n-[4-[2-[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]ethyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1CCN1C(=O)SCC(C=2C=C(OC)C(OC)=CC=2)=N1 DXGNHPZDEQJFQH-UHFFFAOYSA-N 0.000 description 1
• QGZWXQQZLRXVDV-UHFFFAOYSA-N methyl n-[4-[2-[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]ethyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CCC1=CC=C(NC(=O)OC)C=C1 QGZWXQQZLRXVDV-UHFFFAOYSA-N 0.000 description 1
• BKAFSTNVIFNMMW-UHFFFAOYSA-N methyl n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1CN1C(=O)SCC(C=2C=C(OC)C(OC)=CC=2)=N1 BKAFSTNVIFNMMW-UHFFFAOYSA-N 0.000 description 1
• YTSVRBAJMKYHGK-UHFFFAOYSA-N methyl 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)N1CC1=CC=C(NC(=O)OC)C=C1 YTSVRBAJMKYHGK-UHFFFAOYSA-N 0.000 description 1
• DMKNFEJZRJLTTQ-UHFFFAOYSA-N methyl n-[4-[[5-(3-cyclopentyloxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OC)=CC=C1CN1C(=O)SCC(C=2C=C(OC3CCCC3)C(OC)=CC=2)=N1 DMKNFEJZRJLTTQ-UHFFFAOYSA-N 0.000 description 1
• MOYIKIPPRYZVIX-UHFFFAOYSA-N methyl n-[4-[[5-(3-cyclopentyloxy-4-methoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC3CCCC3)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 MOYIKIPPRYZVIX-UHFFFAOYSA-N 0.000 description 1
• IULVIBRHFBNUFN-UHFFFAOYSA-N methyl 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)=CC=3)N=2)=C1 IULVIBRHFBNUFN-UHFFFAOYSA-N 0.000 description 1
• ZOUDIIJDAUJBEJ-UHFFFAOYSA-N methyl 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)OC)=CC=3)N=2)CC)=C1 ZOUDIIJDAUJBEJ-UHFFFAOYSA-N 0.000 description 1
• RETGQPBNKNPXIN-UHFFFAOYSA-N methyl n-[4-[[5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 RETGQPBNKNPXIN-UHFFFAOYSA-N 0.000 description 1
• XBEPCSVZMZNYHP-UHFFFAOYSA-N methyl n-[4-[[6-ethyl-5-[3-(fluoromethoxy)-4-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 XBEPCSVZMZNYHP-UHFFFAOYSA-N 0.000 description 1
• OCFNFLKVIITLDM-UHFFFAOYSA-N methyl n-[4-[[6-ethyl-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OC(F)(F)F)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 OCFNFLKVIITLDM-UHFFFAOYSA-N 0.000 description 1
• GSLTVEGDURRESY-UHFFFAOYSA-N methyl n-[4-[[6-ethyl-5-[4-methoxy-3-(trifluoromethoxy)phenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 GSLTVEGDURRESY-UHFFFAOYSA-N 0.000 description 1
• 150000007522 mineralic acids Chemical class 0.000 description 1
• LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
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