SK12396A3 - Arylalkylthiadiazinone derivative, preparation method thereof and pharmaceutical composition containing its - Google Patents
Arylalkylthiadiazinone derivative, preparation method thereof and pharmaceutical composition containing its Download PDFInfo
- Publication number
- SK12396A3 SK12396A3 SK123-96A SK12396A SK12396A3 SK 12396 A3 SK12396 A3 SK 12396A3 SK 12396 A SK12396 A SK 12396A SK 12396 A3 SK12396 A3 SK 12396A3
- Authority
- SK
- Slovakia
- Prior art keywords
- dihydro
- thiadiazin
- ethyl
- chloride
- dimethoxyphenyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 methylenedioxy Chemical group 0.000 claims abstract description 122
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 229910052801 chlorine Inorganic materials 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
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 239000007788 liquid 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 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
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 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 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 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
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 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 24
- 238000006243 chemical reaction Methods 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
- 239000000243 solution Substances 0.000 description 18
- PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 18
- 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 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
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-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
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 16
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 15
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 description 14
- 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 10
- 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
- 239000004480 active ingredient Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- WTGUUGJZRZUIAU-UHFFFAOYSA-N 1,3,4-thiadiazin-2-one Chemical compound O=C1N=NC=CS1 WTGUUGJZRZUIAU-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000003814 drug Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 208000006673 asthma Diseases 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 3
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 description 2
- 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
- APGGSERFJKEWFG-UHFFFAOYSA-N 1-(chloromethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CCl)=C1 APGGSERFJKEWFG-UHFFFAOYSA-N 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
- BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 2
- MQNJWTBFKHTICB-UHFFFAOYSA-N 3-[(3-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=CC(N)=C1 MQNJWTBFKHTICB-UHFFFAOYSA-N 0.000 description 2
- FCBPEUPAGNMWLQ-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-5-(3-ethoxy-4-methoxyphenyl)-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC(C=2CSC(=O)N(CC=3C=CC(N)=CC=3)N=2)=C1 FCBPEUPAGNMWLQ-UHFFFAOYSA-N 0.000 description 2
- MGJVXWVNZRSIQB-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(N)C=C1 MGJVXWVNZRSIQB-UHFFFAOYSA-N 0.000 description 2
- DONSTYLVNJVPEI-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)SC(=O)N1CC1=CC=C(N)C=C1 DONSTYLVNJVPEI-UHFFFAOYSA-N 0.000 description 2
- HNLAQXFYJRKUSS-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-6-ethyl-5-(3-hydroxy-4-methoxyphenyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(O)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(N)C=C1 HNLAQXFYJRKUSS-UHFFFAOYSA-N 0.000 description 2
- BONSNNHUYAFNBV-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-6-ethyl-5-[3-(fluoromethoxy)-4-methoxyphenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(N)C=C1 BONSNNHUYAFNBV-UHFFFAOYSA-N 0.000 description 2
- ADLVOAVOXFWSCA-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]-6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)SC(=O)N1CC1=CC=C(N)C=C1 ADLVOAVOXFWSCA-UHFFFAOYSA-N 0.000 description 2
- LOQLDQJTSMKBJU-UHFFFAOYSA-N 4-(chloromethyl)benzonitrile Chemical compound ClCC1=CC=C(C#N)C=C1 LOQLDQJTSMKBJU-UHFFFAOYSA-N 0.000 description 2
- GLMBEMGHBMGVNI-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-[(2-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=CC=C1[N+]([O-])=O GLMBEMGHBMGVNI-UHFFFAOYSA-N 0.000 description 2
- NKWMXKPYTPCPIW-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-[(3-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=CC([N+]([O-])=O)=C1 NKWMXKPYTPCPIW-UHFFFAOYSA-N 0.000 description 2
- GEKZZVLYHPQXSP-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3-[(4-nitrophenyl)methyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C(C(SC1=O)CC)=NN1CC1=CC=C([N+]([O-])=O)C=C1 GEKZZVLYHPQXSP-UHFFFAOYSA-N 0.000 description 2
- XNJCMYSJGZVPFE-UHFFFAOYSA-N 5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-3-[(4-nitrophenyl)methyl]-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C([N+]([O-])=O)C=C1 XNJCMYSJGZVPFE-UHFFFAOYSA-N 0.000 description 2
- XYCDAUHBAWWRRP-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3-[(4-nitrophenyl)methyl]-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)SC(=O)N1CC1=CC=C([N+]([O-])=O)C=C1 XYCDAUHBAWWRRP-UHFFFAOYSA-N 0.000 description 2
- WIVMBQZZIYHVCZ-UHFFFAOYSA-N 6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1 WIVMBQZZIYHVCZ-UHFFFAOYSA-N 0.000 description 2
- UMZZOCUGXLIFKP-UHFFFAOYSA-N 6-ethyl-5-(3-hydroxy-4-methoxyphenyl)-3-[(4-nitrophenyl)methyl]-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(O)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C([N+]([O-])=O)C=C1 UMZZOCUGXLIFKP-UHFFFAOYSA-N 0.000 description 2
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- 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
- QKVDOKFVRJNPAQ-UHFFFAOYSA-N methyl n-[4-[[5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 QKVDOKFVRJNPAQ-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
- FTKAZBAIRRJHPR-UHFFFAOYSA-N methyl n-[4-[[6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]carbamate Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)SC(=O)N1CC1=CC=C(NC(=O)OC)C=C1 FTKAZBAIRRJHPR-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
- ROHRSXLSHGNGBA-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2,2,3,3,3-pentafluoropropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC(NC(=O)C(F)(F)C(F)(F)F)=C1 ROHRSXLSHGNGBA-UHFFFAOYSA-N 0.000 description 1
- HNDOKRZZHHSMLB-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2,2-dimethylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC(NC(=O)C(C)(C)C)=C1 HNDOKRZZHHSMLB-UHFFFAOYSA-N 0.000 description 1
- JAPCNYPDOIAKRL-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2-methylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=CC(NC(=O)C(C)C)=C1 JAPCNYPDOIAKRL-UHFFFAOYSA-N 0.000 description 1
- TWBRWLLXFPEHDI-UHFFFAOYSA-N n-[3-[[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=CC(NC(C)=O)=C1 TWBRWLLXFPEHDI-UHFFFAOYSA-N 0.000 description 1
- ZQUOFEXQMMAKMC-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]butanamide Chemical compound CCCC(=O)NC1=CC=CC(CN2C(SCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 ZQUOFEXQMMAKMC-UHFFFAOYSA-N 0.000 description 1
- VUXYQJBENVEBGP-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]hexanamide Chemical compound CCCCCC(=O)NC1=CC=CC(CN2C(SCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 VUXYQJBENVEBGP-UHFFFAOYSA-N 0.000 description 1
- YOSIMISJHGZFPR-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]pentanamide Chemical compound CCCCC(=O)NC1=CC=CC(CN2C(SCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 YOSIMISJHGZFPR-UHFFFAOYSA-N 0.000 description 1
- BXHHFDYEWGQEEC-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]propanamide Chemical compound CCC(=O)NC1=CC=CC(CN2C(SCC(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 BXHHFDYEWGQEEC-UHFFFAOYSA-N 0.000 description 1
- GUWMFPUVIFHGTH-UHFFFAOYSA-N n-[3-[[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=CC(NC(=O)C(F)(F)F)=C1 GUWMFPUVIFHGTH-UHFFFAOYSA-N 0.000 description 1
- DUPVRSDQVPLQPS-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2,2,3,3,3-pentafluoropropanamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=CC(NC(=O)C(F)(F)C(F)(F)F)=C1 DUPVRSDQVPLQPS-UHFFFAOYSA-N 0.000 description 1
- GMOSEJOJHLJVIX-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]-2-methylpropanamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=CC(NC(=O)C(C)C)=C1 GMOSEJOJHLJVIX-UHFFFAOYSA-N 0.000 description 1
- VLFJBUUXXWLKJZ-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]acetamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=CC(NC(C)=O)=C1 VLFJBUUXXWLKJZ-UHFFFAOYSA-N 0.000 description 1
- QNBNCEKMPISAQT-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]butanamide Chemical compound CCCC(=O)NC1=CC=CC(CN2C(SC(CC)C(=N2)C=2C=C(OC)C(OC)=CC=2)=O)=C1 QNBNCEKMPISAQT-UHFFFAOYSA-N 0.000 description 1
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- ZDZBZBXPZBHYFY-UHFFFAOYSA-N n-[3-[[5-(3,4-dimethoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]methanesulfonamide Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CC1=CC=CC(NS(C)(=O)=O)=C1 ZDZBZBXPZBHYFY-UHFFFAOYSA-N 0.000 description 1
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- BITIMRLOKSMRFB-UHFFFAOYSA-N n-[4-[2-[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]ethyl]phenyl]-2,2,2-trifluoroacetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CCC1=CC=C(NC(=O)C(F)(F)F)C=C1 BITIMRLOKSMRFB-UHFFFAOYSA-N 0.000 description 1
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- PYZYAURWIGOZEB-UHFFFAOYSA-N n-[4-[2-[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]ethyl]phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CCC1=CC=C(NC(C)=O)C=C1 PYZYAURWIGOZEB-UHFFFAOYSA-N 0.000 description 1
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- USVVSKUBOOWHPN-UHFFFAOYSA-N n-[4-[[5-(3,4-dimethoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]phenyl]methanesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1C(CSC1=O)=NN1CC1=CC=C(NS(C)(=O)=O)C=C1 USVVSKUBOOWHPN-UHFFFAOYSA-N 0.000 description 1
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- ARZFBYIAGOVOTF-UHFFFAOYSA-N n-cyclopentyl-4-[[5-(3-ethoxy-4-methoxyphenyl)-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2CSC(=O)N(CC=3C=CC(=CC=3)C(=O)NC3CCCC3)N=2)=C1 ARZFBYIAGOVOTF-UHFFFAOYSA-N 0.000 description 1
- KEINRRDVSVBHIB-UHFFFAOYSA-N n-cyclopentyl-4-[[5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]benzamide Chemical compound C1=C(OC)C(OCC)=CC(C=2C(SC(=O)N(CC=3C=CC(=CC=3)C(=O)NC3CCCC3)N=2)CC)=C1 KEINRRDVSVBHIB-UHFFFAOYSA-N 0.000 description 1
- NTLVGKIGBBRTFN-UHFFFAOYSA-N n-cyclopentyl-4-[[5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(OC(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC(C=C1)=CC=C1C(=O)NC1CCCC1 NTLVGKIGBBRTFN-UHFFFAOYSA-N 0.000 description 1
- XJVVCRGMATXERK-UHFFFAOYSA-N n-cyclopentyl-4-[[5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(OC)C(OC(F)F)=CC=2)C(CC)SC(=O)N1CC(C=C1)=CC=C1C(=O)NC1CCCC1 XJVVCRGMATXERK-UHFFFAOYSA-N 0.000 description 1
- AYQWMWUSPICEPZ-UHFFFAOYSA-N n-cyclopentyl-4-[[6-ethyl-5-[3-(fluoromethoxy)-4-methoxyphenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(OCF)C(OC)=CC=2)C(CC)SC(=O)N1CC(C=C1)=CC=C1C(=O)NC1CCCC1 AYQWMWUSPICEPZ-UHFFFAOYSA-N 0.000 description 1
- SBDGECZYYXIJTQ-UHFFFAOYSA-N n-cyclopentyl-4-[[6-ethyl-5-[4-methoxy-3-(trifluoromethoxy)phenyl]-2-oxo-6h-1,3,4-thiadiazin-3-yl]methyl]benzamide Chemical compound N1=C(C=2C=C(OC(F)(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CC(C=C1)=CC=C1C(=O)NC1CCCC1 SBDGECZYYXIJTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Oblasť techniky
Vynález sa týka derivátu arylalkyltiadiazinónu, spôsobu jeho prípravy a farmaceutického prostriedku, ktorý ho obsahuje. De. riváty arylalkyltiadiazinónu podlá vynálezu vykazujú brzdiace pôo sobenie na fosfodiesterázu IV a môžu sa preto používať na ošetro- vanie astmatických ochorení. Môžu sa tiež používať ako medziprodukty pre výrobu ďalších liečiv.
Doterajší stav techniky
Podobné tiadiazinóny ako podlá vynálezu sú známe z nemeckého patentového spisu číslo 37 19 031 A1 a číslo 41 34 893. Úlohou vynálezu je vyvinúť ďalšie zlúčeniny s hodnotnými vlastnosťami, ktoré by boli najmä použiteľné pre výrobu farmaceutických prostriedkov.
. Podstata vynálezu •Λ « Podstatou vynálezu je derivát arylalkyltiadiazinónu všeobecného vzorca I
kde znamená
R1 a R2 na sebe nezávisle atóm vodíka alebo skupinu symbolu A,
R3 a R4 na sebe nezávisle hydroxylovú skupinu, skupinu vzorca
-OR10, -S-R10, -SO-R10, -SO2_R10, Hal, metyléndioxyskupinu, nitroskupinu, skupinu -NH2, -NHR10 alebo -NR^R11,
R5 fenylovú skupinu nesubstituovanú alebo substituovanú jedným alebo dvoma substituentmi symbolu R a/alebo R ,
Q chýba alebo znamená alkylénovú skupinu s 1 až 6 atómami • uhlíka, < R6 a R7 vždy na sebe nezávisle skupinu -NH2, -NR8R9, -NHR10,
Ί Π 11
-NRR, nitroskupinu, Hal, kyanoskupinu, skupinu -0A, -COOH alebo -COOA, q q
R a R vždy na sebe nezávisle atóm vodíka, acylovú skupinu s 1 až 8 atómami uhlíka, prípadne substituovanú jedným až piatimi atómami fluóru a/alebo chlóru, skupinu -COOA, -S-A, -so2-a, -soa, conh2, -CONHA, -cona2, -CO-COOH, -CO-COOA, -CO- CONH2, -CO-CONHA alebo -CO-CONA2,
A alkylovú skupinu s 1 až 6 atómami uhlíka prípadne substituovanú jedným až piatimi atómami fluóru a/alebo ’ chlóru, t R10 a R11vždy na sebe nezávisle A, cykloalkylovú skupinu s 3 až 7 atómami uhlíka, metyléncykloalkylovú skupinu s 4 až 8 atómami uhlíka, alebo alkenylovú skupinu s 2 až 8 atómami uhlíka a
Hal atóm fluóru, chlóru, brómu alebo jódu a jeho fyziologicky vhodná sol.
Zistilo sa, že zlúčeniny všeobecného vzorca I majú hodnotné farmakologické vlastnosti a okrem toho sú dobre znášané.
Tieto zlúčeniny najmä vykazujú brzdiace pôsobenie na fosfodiesterázu IV a môžu sa preto používať na ošetrovanie astmatic3 kých ochorení. Antiastmatické pôsobenie sa zisťuje testom,/ktorý opísal T. Olsson (Acta allergologica, 26, str. 438 až 447, 1971).
Zlúčeniny všeobecného vzorca I vykazujú okrem toho brzdiace pôsobenia na väzbu TNF (= tumor necrose factor) a hodia sa preto na ošetrovanie alergických a zápalových ochorení, autoimunitných ochorení a reakcií odmietania transplantátov. Môžu sa rovnako používať na ošetrovanie porúch pamäti.
Zlúčeniny všeobecného vzorca I podlá vynálezu sa preto môžu používať ako účinné látky pre výrobu farmaceutických prostriedkov pre humánnu i veterinárnu medicínu. Môžu sa tiež používať ako medziprodukty pre výrobu ďalších liečiv.
Spôsob prípravy zlúčeniny všeobecného vzorca I spočíva podlá vynálezu v tom, že sa zlúčenina všeobecného vzorca II
so zlúčeninou všeobecného vzorca III
R5 - Q - X (III) kde R5 a Q má hore uvedený význam a kde znamená X atóm chlóru, brómu, hydroxylovú skupinu alebo reaktívnu esterifikovanú hydroxylovú skupinu, alebo sa v zlúčenine všeobecného vzorca I zvyšok symbolu premiena na iný zvyšok symbolu R tým, ze sa redukuje nitroskupina, alkyluje alebo acyluje sa primárna alebo sekundárna aminoskupina alebo sa hydrolyzuje kyanoskupina, a/alebo sa zlúčenina zodpovedajúca všeobecnému vzorci I, ktorá má však miesto skupiny symbolu R3 a/alebo R4 jednu alebo dve volné hydroxylové skupiny necháva reagovať so zlúčeninou všeobecného vzorca R3-X prípadne R4-X, kde R3, R4 a X majú hore uvedený význam, a/alebo sa zásada všeobecného vzorca I premieňa pôsobením kyseliny na zodpovedajúcu soľ.
Symboly R3·, R^, R3, R4, R$, Q a X majú vždy význam, uvedený pri všeobecnom vzorci I, II a III, pokial to výslovne nie je uvedené inak.
Vo všeobecných vzorcoch je alkylová skupina s výhodou nerozvetvená s 1, 2, 3 alebo 4 atómami uhlíka, s výhodou je to skupina metylová ďalej s výhodou skupina etylová a propylová, ďalej s výhodou skupina izopropylová, butylová, izobutylová, ďalej s výhodou sek.-butylová, terc.-butylová skupina avšak tiež skupina n-pentylová alebo izopentylová skupina.
Cykloalkylová skupina má s výhodou 3 až 7 atómov uhlíka a s výhodou je to skupina cyklopropylová a cyklobutylová ďalej s výhodou skupina cyklopentylová a cyklohexylová a ďalej tiež skupina cykloheptylová.
Metyléncykloalkylová skupina má s výhodou 4 až 8 atómov uhlíka a s výhodou je to skupina metyléncyklopropylová a metyléncyklobutylová ďalej s výhodou skupina metyléncyklopentylová a metyléncyklohexylová a ďalej tiež skupina metyléncykloheptylová.
Alkenylovou skupinou je s výhodou skupina vinylová, propenylová, izopropenylová, butenylová, izobutenylová, sek.-butenylová, ďalej s výhodou skupina pentenylová a izopentenylová.
Alkylénová skupina je s výhodou nerozvetvená a je to s výhodou skupina metylénová alebo etylénová, ďalej s výhodou skupina propylénová alebo butylénová.
Zo symbolov R1 a R2 znamená prvý s výhodou atóm vodíká, zatiaľ čo druhý s výhodou propylovú alebo butylovú skupinu, najmä však etylovú alebo metylovú skupinu. Okrem toho znamenajú obidva symboly R1 a R2 dohromady s výhodou vždy atóm vodíka.
Skupiny symbolu R3 a R4 môžu byt rovnaké alebo rôzne a sú s výhodou v polohe 3 alebo 4 fenylového jadra. Znamenajú napríklad na sebe nezávisle hydroxyskupinu, skupinu -S-CH3, -SO-CH3, -SO2“CH3, atóm fluóru, chlóru, brómu alebo jódu alebo spolu dohromady metyléndioxyskupinu. Najmä však s výhodou znamenajú metoxyskupinu, etoxyskupinu, propoxyskupinu alebo tiež fluórmetoxyskupinu, difluórmetoxyskupinu, trifluórmetoxyskupinu, 1-fluóretoxyskupinu, 2-fluóretoxyskupinu, 1,2-difluóretoxyskupinu, 2,2difluóretoxyskupinu, 1,2,2-trifluóretoxyskupinu alebo 2,2,2-trifluóretoxyskupinu.
Symbol R5 znamená s výhodou fenylovú skupinu. Fenylová skupina má s výhodou jeden alebo dva substituenty. Ako výhodné substituenty sa uvádzajú kyanoskupina, nitroskupina, aminoskupina, acetamidoskupina, trifluóracetamidoskupina, metoxyskupina a/alebo atóm chlóru, dalej sú výhodné metylsulfonamidoskupina, propionylaminoskupina, 2-metylpropionylaminoskupina, izobutyrylaminoskupina a/alebo pivalylaminoskupina, dalej sú výhodné metoxykarbonylaminoskupina, metoxalylaminoskupina, ureidoskupina a/alebo karboxyskupina.
Symbol Q-R3 znamená s výhodou skupinu benzylovú, 2-, 3- alebo 4-nitrobenzylovú, 2, 3-, alebo 4-kyánbenzylovú, 2-, 3-, alebo 4-aminobenzylovú, 2-, 3-, alebo 4-acetamidobenzylovú, 2-,3-, alebo 4-trifluóracetamidobenzylovú, 2, 3-, alebo 4-metoxybenzylovú, 2, 3-, alebo 4-chlórbenzylovú, dalej s výhodou skupinu 2, 3-, alebo 4-metylsulfonamidobenzylovú, 2, 3-, alebo 4-propionylaminobenzylovú, 2, 3-, alebo 4-(2-metylpropionylamino)benzylovú,
2— , 3—, alebo 4-izobutyrylaminobenzylovú, 2-, 3- alebo 4-pivalylaminobenzylovú, 2-, 3- alebo 4-metoxykarbonylaminobenzylovú, 2-,
3- alebo 4-ureidobenzylovú, 2-, 3- alebo 4-karboxybenzylovú, 2-,
3- alebo 4-metoxalylaminobenzylovú, ďalej s výhodou skupinií 2,3-,
2.4- , 2,5-, 2,6-, 3,4- alebo 3,5-dinitrobenzylovú, 2,3-, 2,4-,
2.5- , 2,6-, 3,4- alebo 3,5-diaminobenzylovú, 2,3-, 2,4-, 2,5-,
2.6- , 3,4- alebo 3,5-diacetamidobenzylovú, 2,3-, 2,4-, 2,5-,
2,6, 3,4- alebo 3,5-bis-(trifluóracetamido)benzylovú, 2,3-, 2,4-,
2.5- , 2,6-, 3,4- alebo 3,5-dimetoxybenzylovú, 2,3-, 2,4-, 2,5-,
2.6- , 3,4- alebo 3,5-dichlórbenzylovú, 2,3-, 2,4-, 2,5-, 2,6-,
3.4- alebo 3,5-dimetylsulfonamidobenzylovú, 2,3-, 2,4-, 2,5-,
2,6-, 3,4- alebo 3,5-dipropionylaminobenzylovú, 2,3-, 2,4-, 2,5-,
2,6-, 3,4- alebo 3,5-bis-(2-metylpropionylamino)benzylovú, 2,3-,
2.4- , 2,5-, 2,6-, 3,4- alebo 3,5-diizobutyrylaminobenzylovú,
2,3-, 2,4-, 2,5-, 2,6-, 3,4- alebo 3,5-dipivalylaminobenzylovú, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- alebo 3,5-dimetoxykarbonylaminobenzylovú, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- alebo 3,5-dimetoxalylaminobenzylovú, 2,3-, 2,4-, 2,5- 2,6-, 3,4- alebo 3,5-diureidobenzylovú, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- alebo 3,5-dikarboxybenzylovú skupinu.
Vynález sa teda týka najmä derivátov arylalkyltiadiazinónu všeobecného vzorca I, v ktorých aspoň jeden zo symbolov má hore uvedený výhodný význam. Niektorými výhodnými skupinami zlúčenín všeobecného vzorca I sú nasledujúce zlúčeniny čiastkových vzorcov la až Ie, kde osobitne neuvedené symboly majú význam uvedený pri všeobecnom vzorci I:
v la znamená R1 atóm vodíka, o
R atóm vodíka alebo skupinu symbolu A,
O
R skupinu symbolu OA, v Ib znamená
RJ atóm vodíka, o
R skupinu metylovu alebo etylovu,
R3 a R4 vždy skupinu symbolu OA, v Ic znamená R1 atóm vodíka,
R2 skupinu metylovú alebo etylovú,
R3 skupinu symbolu OA, a v Id znamená R mono-, di- alebo trisubstituovanú alkylovú skupinu s 1 až 6 atómami uhlíka, atóm vodíka,
Rz skupinu metylovú alebo etylovú,
R3 a R4 vždy skupinu symbolu OR10,
R5 fenylovú skupinu s jedným alebo sa dvoma substituentmi ' 1 ?
v Ie znamena R a R
R3 a R4
R' atóm vodíka, vždy skupinu symbolu OA, fenylovú skupinu s jedným alebo sa dvoma substituentmi.
Zlúčeniny všeobecného vzorca I sa pripravujú známymi spôsobmi, ktoré sú opísané v literatúre (napríklad v štandardných publikáciách ako Houben-Weyl, Methoden der organischen Chemie, Georg-Thieme Verlag, Stuttgart), a to v reakčných podmienkach, ktoré sú pre menované reakcie známe a vhodné. Pritom sa môžu tiež používať známe, tu bližšie neopisované varianty.
V zlúčeninách všeobecného vzorca II majú R1, R2, R3, R4 hore uvedený význam, najmä hore uvedený výhodný význam.
V zlúčeninách všeobecného vzorca III znamená Q s výhodou metylénovú alebo etylénovú skupinu, ďalej s výhodou propylénovú alebo butylénovú skupinu.
Symbol R5 v zlúčeninách všeobecného vzorca III má hore uvedený význam, najmä hore uvedený výhodný význam, pričom X znamená atóm chlóru, brómu, hydroxyskupinu alebo reaktívnu esterifikovanú hydroxyskupinu. Pokial znamená X reaktívnu esterifikovanú hydroxyskupinu, ide s výhodou o alkylsulfonyloxyskupinu s 1 až 6 atómami uhlíka, napríklad o metánsulfonyloxyskupinu alebo o arylsulfonyloxyskupinu s 6 až 10 atómami uhlíka, ako sú napríklad benzénsulfonyloxyskupina, toluénsulfonyloxyskupina, alebo 1-naftalénsulfonyloxyskupina, alebo 2-naftalénsulfonyloxyskupina.
Východiskové látky sa môžu prípadne vytvárať tiež in situ tak, že sa z reakčnej zmesi neizolujú, ale sa ihneď nechávajú ďalej reagovat na zlúčeniny všeobecného vzorca I. Je však tiež možné uskutočňovať reakciu postupne.
Východiskové látky všeobecného vzorca II a III sú sčasti známe. Pokial nie sú známe, môžu sa pripravovať známymi spôsobmi.
Tiadiazinóny všeobecného vzorca II a spôsob ich prípravy sú opísané napríklad v nemeckej zverejnenej prihláške vynálezu P 41 34 893.
Zlúčeniny všeobecného vzorca III sa ostatne môžu pripravovať známymi spôsobmi, ktoré sú opísané v literatúre (napríklad v štandardných publikáciách ako je Houben-Weyl, Methoden der organischen Chemie, Georg-Thieme Verlag, Stuttgart), a to v reakčných podmienkach, ktoré sú pre menované reakcie známe a vhodné. Pritom sa môžu tiež používať známe, tu bližšie neopisované varianty.
Reakcia tiadiazinónov všeobecného vzorca II so zlúčeninami všeobecného vzorca III sa môže uskutočňovať v prítomnosti alebo v neprítomnosti rozpúšťadla pri teplotách -20 až približne +150°C, s výhodou pri teplote 20 až 100C. Ako rozpúšťadla sú vhodné uhľovodíky, ako napríklad benzén, toluén, xylény alebo mezitylén; halogénované uhľovodíky, ako dichlórmetán, trichlóretylén alebo chlórbenzén; alkoholy ako metanol, etanol alebo izopropanol; glykoly a glykolétery ako etylénglykol, dietylénglykol alebo metoxyetanol); nitrily ako acetonitril; étery ako tetrahydrofurán (THF) alebo dioxán; amidy ako dimetylformamid (DMF); sulfoxidy ako dimetylsulfoxid (DMSO). Okrem toho sú tiež vhodné zmesi týchto rozpúšťadiel.
Je tiež možné v zlúčenine všeobecného vzorca I zvyšok R pre meniť na iný zvyšok R5 tým, že sa nitroskupina redukuje, primárna alebo sekundárna aminoskupina sa alkyluje alebo acyluje alebo sa kyanoskupina hydrolyzuje.
Je tiež možné zlúčeninu, ktorá inak zodpovedá všeobecnému vzorci I má však miesto R3 a/alebo R4 jednu alebo dve volné hydroxylové skupiny, nechávať reagovať so zlúčeninou všeobecného vzorca R3-X prípadne R4-X, kde R3, R4 a X majú hore uvedený význam. Éterifikácia hydroxylových skupín sa vykonáva známymi spôsobmi, ktoré sú opísané v literatúre (napríklad v štandardných publikáciách ako Houben-Weyl, Methoden der organischen Chemie, Georg-Thieme Verlag, Stuttgart; Organic Reactions, John Wiley & Sons, Inc. New York), a to v reakčných podmienkach, ktoré sú pre menované reakcie známe a vhodné. Pritom sa môžu tiež používať známe, tu bližšie neopisované varianty.
Zásada všeobecného vzorca I sa môže kyselinou premieňať na príslušnú adičnú sol s kyselinou. Pre túto reakciu prichádzajú do úvahy najmä kyseliny, ktoré poskytujú fyziologicky nezávadné soli Môžu sa používať anorganické kyseliny, ako sú kyselina sírová, dusičná, halogenovodíkové kyseliny, ako chlorovodíková alebo bromovodíková, fosforečné kyseliny, ako kyselina ortofosforečná, sulfamínová kyselina a organické kyseliny, najmä alifatické, alicyklické, aralifatické, aromatické alebo heterocyklické jednosýtne alebo niekolkosýtne karboxylové, sulfónové alebo sírové kyseliny, ako sú kyselina mravčia, octová, propiónová, pivalová, dietyloctová, malónová, jantárová, pimelová, fumarová, maleínová, mliečna, vínna, jablčná, benzoová, salicylová, 2-fenylpropiónová, alebo 3-fenylpropiónová, citrónová, glukónová, askorbová, nikotínová, izonikotínová, metánsulfónová, etánsulfónová, etándisulfónová, 2-hydroxyetánsulfónová, benzénsulfónová, p-toluénsulfónová, naftalénmonosulfónová a naftaléndisulfónová a laurylsírová kyselina .
Voíné zásady sa môžu prípadne uvoíňovať zo svojich solí spra covaním silnou zásadou, ako hydroxidom sodným alebo draselným.
Zlúčeniny všeobecného vzorca I môžu mať jedno alebo niekolko center asymetrie. V takom prípade sú spravidla v racemickej forme. Prípadne sa získané racemáty môžu známymi spôsobmi mechanicky alebo chemicky deliť na svoje enantioméry. S výhodou sa vytvárajú diastereoizoméry z racemátu reakciou s opticky aktívnym deliacim činidlom.
Prirodzene je tiež možné získať opticky aktívne zlúčeniny všeobecného vzorca I hore opísanými spôsobmi pri použití opticky aktívnych východiskových látok.
Všeobecný vzorec I zahŕňa všetky stereoizoméry a ich zmesi, napríklad racemáty.
Vynález sa tiež týka použitia derivátu arylalkyltiadiazinónu všeobecného vzorca I a jeho fyziologicky nezávadných solí na výrobu farmaceutických prostriedkov, najmä nechemickou cestou. Za týmto účelom sa môžu premieňať na vhodnú dávkovaciu formu s aspoň jedným pevným alebo kvapalným a/alebo polokvapalným nosičom alebo pomocnou látkou a prípadne v zmesi s jednou alebo s niekolkými inými účinnými látkami.
Vynález sa preto tiež týka prostriedkov, farmaceutických prostriedkov, obsahujúcich aspoň jednu zlúčeninu všeobecného vzorca I, a/alebo jej fyziologicky vhodnú soí.
Tieto prostriedky podía vynálezu sa môžu používať ako liečivá v humánnej a vo veterinárnej medicíne. Ako nosiče prichádzajú do úvahy anorganické alebo organické látky, ktoré sú vhodné pre enterálne (napríklad orálne) alebo pre parenterálne alebo topické podávanie a ktoré nereagujú so zlúčeninami všeobecného vzorca I, ako sú napríklad voda, rastlinné oleje, benzylalkoholy, polyetylénglykoly, glyceríntriacetát, želatína, uhľohydráty, ako laktóza alebo škroby, stearan horečnatý, mastenec a vazelína. Pre orálne použitie sa hodia najmä tablety, dražé, kapsuly, sirupy, šťavy alebo kvapky, pre rektálne použitie čapíky, pre parenterálne použitie roztoky, najmä olejové alebo vodné roztoky, dalej suspenzie, emulzie alebo implantáty, pre topické použití masti, krémy, alebo púdre. Zlúčeniny podlá vynálezu sa tiež môžu lyofilizovať a získané lyofilizáty sa môže napríklad používať na prípravu vstrekovatelných prostriedkov. Prostriedky sa môžu sterilizovať a/alebo môžu obsahovať pomocné látky, ako sú lubrikačné činidlá, konzervačné, stabilizačné činidlá a/alebo namáčadlá, emulgátory, soli na ovplyvnenie osmotického tlaku, tlmivé roztoky, farbivá, chuťové prísady a/alebo aromatické látky. Prípadne, môžu obsahovať ešte jednu dalšiu alebo ešte niekoľko dalších účinných látok, ako sú napríklad vitamíny.
Zlúčeniny všeobecného vzorca I a ich fyziologicky nezávadné soli sa môžu používať na liečbu chorôb najmä astmatických ochorení ako tiež na terapeutické ošetrovanie ľudských a zvieracích tiel.
Zlúčeniny všeobecného vzorca I podlá vynálezu sa spravidla používajú v dávkach podobných ako známe antiastmatiká, napríklad p
Atrovent , s výhodou v dávke približne 1 až 100 mg, najmä 2 až 20 mg na dávkovaciu jednotku. Denná dávka je približne 0,02 až 2 mg/kg telesnej hmotnosti. Určitá dávka pre každého jednotlivého pacienta závisí od najrôznejších faktorov, napríklad od účinnosti určitej použitej zlúčeniny, od veku, telesnej hmotnosti, všeobecného zdravotného stavu, pohlavia, stravy, od okamihu a cesty podania, od rýchlosti vylučovania, od kombinácie liečiv a od závažnosti určitého ochorenia. Výhodné je orálne podávanie. V porovnaní s doterajšou terapiou majú zlúčeniny všeobecného vzorca I podlá vynálezu zlepšenú terapeutickú šírku a znížené zaťažovanie organizmu.
Výraz spracovanie obvyklým spôsobom v nasledujúcich príkladoch praktického rozpracovania znamená:
Prípadne sa pridáva voda, alebo zriedený sodný lúh, reakčná zmes sa extrahuje organickým rozpúšťadlom, ako etylacetátom, chloroformom alebo dichlórmetánom, uskutočňuje sa oddelenie, vysušenie organickej fázy síranom sodným, filtrácia, odparenie a čistenie chromatografiou a/alebo kryštalizáciou.
Vynález objasňujú, žiadnym spôsobom však neobmedzujú nasledujúce príklady praktického rozpracovania.
Príklady rozpracovania vynálezu
Príklad 1 hodín sa varí roztok 2,8 g 5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-onu (A) [získatelného reakciou 1 (3,4-dimetoxyfenyl)-2-brómbután-l-onu s hydrazíntiometylesterom kyseliny mravčej] v 150 ml acetónu s 3 g 4-nitrobenzylchloridu v prítomnosti 4 g uhličitanu draselného. Nerozpustný zvyšok sa odfiltruje a roztok sa zahustí. Po spracovaní obvyklým spôsobom sa získa 3-(4-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on v podobe bezfarbého oleja.
Obdobne sa získa reakciou A s 3-nitrobenzylchloridom:
3-(3-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s 2-nitrobenzylchloridom:
3-(2-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s 2,3-dinitrobenzylchloridom:
3-(2,3-dinitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihýdro1,3,4-tiadiazín-2-on, s 2,4-dinitrobenzylchloridom:
3-(2,4-dinitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s 2-metoxybenzylchloridom:
3-(2-metoxybenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s 4-metoxybenzylchloridom:
3-(4-metoxybenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s teplotou topenia 120°C s 2-chlórbenzylchloridom:
3-(2-chlórbenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s teplotou topenia 77°C s 2,6-dichlórbenzylchloridom:
3-(2,6-dichlórbenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s teplotou topenia 187°C sa 4-kyánbezylchloridom:
3-(4-kyánbezyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s 4-karboxybenzylchloridom:
3-(4-karboxybenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s teplotou topenia 106C.
Príklad 2
Obdobne ako podlá príkladu 1 sa získa reakciou 5-(3,4-dimet oxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-onu (B) s 4-nitroben14 zylchloridom 3-(4-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-díhydro-1,3,4-tiadiazín-2-on, s teplotou topenia 155°C.
Obdobne sa získa reakciou B s 3-nitrobenzylchloridom:
3-(3-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on, s 2,4-dinitrobenzylchloridom:
3-(2,4-dinitrobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on, s 4-metoxybenzylchloridom:
3-(4-metoxybenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on, s 2-chlórbenzylchloridom:
3-(2-chlobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l ,3,4tiadiazín-2-on, s 2,6-dichlórbenzylchloridom:
3-(2,6-dichlórbenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on, s 4-kyánbezylchloridom:
3-(4-kyánbezyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on.
Príklad 3
Obdobne ako podía príkladu 1 sa získa reakciou 5-(3-metoxy 4-trifluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s 4-nitrobenzylchloridom (C) 3-(4-nitrobenzyl)-5-(3-metoxy-4trifluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou (C) s 5- ( 3-metoxy-4-difluórmetoyfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3-(4-nitrobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6-etyl-3,6 dihydro-1,3,4-tiadiazín-2-on, s 5-( 3-metoxy-4-fluórmetoxyfenyl) -6-etyl-3,6-dihydro-l ,3,4tiadiazín-2-onom:
3- (4-nitrobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s 5-( 3-difluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3-(4-nitrobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl-3,6 dihydro-1,3,4-tiadiazín-2-on, s 5- (3-trifluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3-(4-nitrobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6-etyl-3, dihydro-1,3,4-tiadiazín-2-on, s 5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3-(4-nitrobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s 5-(3-metoxy-4-etoxyfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3-(4-nitrobenzyl)-5-(3-metoxy-4-etoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s 5-(3-etoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3-( 4-nitrobenzyl )-5- (3-etoxy-4-metoxyfenyl) -6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s 5- ( 3-hydroxy-4-metoxyfenyl) -6-etyl-3,6-dihydro-l ,3,4tiadiazín-2-onom:
3- ( 4-nitrobenzyl) -5- ( 3-hydroxy-4-metoxyfenyl) -6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s 5-(4-metylsulfonylfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3- (4-nitrobenzyl) -5- (4-metylsulf onylf enyl) -6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s 5-(3,4-metylénoxyfenyl)-6-etyl-3,6-dihydro-l,3,4tiadiazín-2-onom:
3-(4-nitrobenzyl)-5-(3,4-metylénoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on.
Príklad 4
V prítomnosti Ranney-niklu ako katalyzátoru sa hydrogenuje roztok 3,9 g 3-(4-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-6- etyl3,6-dihydro-l,3,4-tiadiazín-2-onu v 40 ml tetrahydrofuráne. Katalyzátor sa odfiltruje a roztok sa zahustí. Po prekryštalizovaní sa získa 3-(4-aminobenzyl)-5-(3,4-dimetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 105°C
Obdobne sa získa reakciou:
3- ( 3-nitrobenzyl) -5- ( 3,4-dimetoxyf enyl) -6-etyl-3,6-dihydro1.3.4- tiadiazín-2-onu
3- (3-aminobenzyl) -5- (3,4-dimetoxyf enyl) -6-etyl-3,6-dihydro1.3.4- tiadiazín-2-on, s teplotou topenia 112’C.
3-(2-nitrobenzyl)-5-(3,4-dimetoxyfenyl) -6-etyl-3,6-dihydro1.3.4- tiadiazín-2-onu:
3-(2-aminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1.3.4- tiadiazín-2-on,
3-(2,3-dinitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro
1.3.4- tiadiazín-2-onu:
3-(2,3-diaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro
1.3.4- tiadiazín-2-on,
3-(2,4-dinitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro
1.3.4- tiadiazín-2-onu:
3-(2,4-diaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro
1.3.4- tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro
1.3.4- tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro
1.3.4- tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6-etyí
3.6- dihydro-l,3,4-tiadiazín-2-onu;
3-(4-aminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6-etyl
3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-metoxy-4-etoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-metoxy-4-etoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-hydroxy-4-metoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-hydroxy-4-metoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(4-metylsulfonylfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(4-metylsulfonylfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3,4-metylénoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3,4-metylénoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl
3.6- dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl
3.6- dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 132°C,
3-(4-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on,
3-(3-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-onu:
3-(3-aminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6-dihydro-l,3,4 tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-etoxy-4-metoxyfenyl) — 3,6-dihydro-l,3,4 tiadiazín-2-on, s teplotou topenia 176°C,
3-(4-nitrobenzyl)-5-(4-etoxy-3-metoxyfenyl)-3,6-dihydro-l,3,4 tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(4-etoxy-3-metoxyfenyl)-3,6-dihydro-l,3,4 tiadiazín-2-on,
3-( 4-nitrofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-onu:
3-(4-aminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-οη,
3-(4-nitrobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-3,6dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-3,6-dihydro
1.3.4- tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-3,6-dihydro
1.3.4- tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-onu:
3- (4-aminobenzyl) -5- (3-metoxy-4-trif luórmetoxyf enyl )-3,6dihydro-1,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-3,6dihydro-l,3,4-tiadiazín-2-on,
3-(4-nitrobenzyl )-5-( 3-trif luórmetoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-onu:
3- (4-aminobenzyl) -5- (3-trif luórmetoxy-4-metoxyf enyl )-3,6dihydro-1,3,4-tiadiazín-2-on.
Príklad 5
Do chladeného roztoku 1,3 g hydroxidu sodného v 100 ml vody sa za miešania pridá 10 g 3-(4-kyánbenzyl)-5-(3,4-dihydroxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu a roztok sa potom mieša ďalších 10 hodín.
Zahrieva sa a opatrne sa roztokom nechá prebublávat vzduch. Nakoniec sa pridá chladená kyselina sírová a voda. Roztok sa spracuje obvyklým spôsobom a získa sa 3-(4-karboxybenzyl)-5-(3,
4- dihydroxyf enyl) -6-etyl-3,6-dihydro-l, 3,4-tiadiazín-2-on, s teplotou topenia 106°C.
Príklad 6
Za chladenia ľadom a za miešania sa nechá reagovať roztok 1,4 g 3-(4-aminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3-4-tiadiazín-2-onu (D) v 60 ml dichlórmetánu a v 1 ml trietylamínu s 0,80 ml trifluóracetylchloridu a 3 hodiny sa ďalej mieša. Rozpúšťadlo sa odstráni a reakčná zmes sa spracuje obvyklým spôsobom. Po prekryštalizovaní zo systému izopropanol/petrol éter sa získa 1,9 g 3-(4-trifluórcetamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu, s teplotou topenia 124°C.
Obdobne sa získa reakciou D” s acetylchloridom:
3- (4-acetamidobenzyl) -5- (3,4-dimetoxyf enyl) -6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on v podobe oleja, MS (E1)M+ 427, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, amorfný, MS (E1)M+ 463, s propionylchloridom:
3-(4-propionylamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, amorfný, MS (El)M+ 441, s izobutyrylchloridom:
3- (4-izobutyrylamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, amorfný, MS (E1)M+ 455, s metylesterom kyseliny chlórmravčej:
3-(4-metoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on,s teplotou topenia 141°C, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s teplotou topenia 155°C, s chloridom cyklopentánkarboxylovej kyseliny:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 115°C, s etylesterom kyseliny chlórmravčej:
3-(4-etoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, amorfný, MS (El) M+457, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, amorfný, MS (El) M+472, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s teplotou topenia 140°C, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-1,3,4-tiadiazín-2-on, s teplotou topenia 77°C, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-1,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-1,3,4-tiadiazín-2-on, amorfný, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 113°C
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-etoxy4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3- (4-trifluóracetamidobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl
3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 155’C, s chloridom kyseliny cyklopentánkarboxylovej :
3- (4-cyklopentylkarbamoylbenzyl )-5-( 3-etoxy-4-metoxyf enyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3- (4-metylsulfomylamidobenzyl) -5- ( 3-etoxy-4-metoxyfenyl) -6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 136°C, s izobutyrylchloridom:
3- (4-izobutyrylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom kyseliny chlórmravčej:
3- (4-metoxykabonylaminobenzyl) -5- (3-etoxy-4-metoxyf enyl) -6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom kyseliny chlórmravčej:
3-(4-etoxykabonylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl
3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 160°C, s metoxalylchloridom:
3- ( 4-metoxalylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformaitiidom:
3-(4-ureidobenzyl) -5-(3-etoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l ,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3- (4-pivalylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s hexanoylchloridom:
3- ( 4-hexanolylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3- ( 4-pentafluórpropionylaminobenzyl) -5- (3-étoxy-4-metoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-cyklopentyl oxy-4-metoxyfenyl) -6-etyl-3,6-dihydro-l, 3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, amorfný, MS (EI)M+481, s metylsulfonylchloridom:
3-(4-metylsulfonylamidobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom kyseliny chlórmravčej:
3-(4-metoxykabonylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom kyseliny cyklopentakarboxylovej:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom kyseliny chlórmravčej:
3-(4-etoxykarbonylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazin-2-on, s teplotou topenia 146°C, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-cyklopentvloxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiaζίη-2-οη, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6-etyl3.6- dihydro-l, 3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl) -6 etyl-3,6-dihydro-l, 3,4-tiadiazírt-2~on, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3-cyklopentyloxy-4metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou 3-(4-aminofénetyl)-5-(3,4-dimet oxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl3.6- dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-l ,3,4-tiadiazin-2-on, j topení A. ΉΖ s metylsulfonylchloridom:
3-(4-metylsulfonamidofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s metylesterom kyseliny chlórmravčej:
3-(4-metoxykarbonylaminofénetyl)-5-(3,4-dimetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom kyseliny chlórmravčej:
3-(4-etoxykarbonylaminofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminofénetyl)-5-(3,4- dimetoxyfenyl)-6-etyl-3,6dihydro-l,3,4-tiadiazín-2-on, s chloridom kyseliny cyklopentakarboxylovej:
3-(4-cyklopentylkarbamoylfenetyl)-5-(3,4-dimetoxyfenyl)-6-etyl
3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminofénetyl) -5-(3,4- dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexaanoylaminofénetyl)-5-(3,4- dimetoxyfenyl)-6-etyl-3,6dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom;
3-(4-pentafluórpropionylaminofénetyl)-5-(3,4- dimetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3-(4-pivalyaminofénetyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-l,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou 3-(3-aminobenzyl)-5-(3,4-dimetoxy fenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(3-trifluóracetamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-l,3,4-tiadiazín-2-on, amorfný, MS (E1)M+ 481, s acetylchloridom:
3-(3-acetamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3-(3-metylsulfonamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazin-2-on, s propionylchloridom:
3-(3-propionylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s teplotou topenia 159°C, s chloridom kyseliny cyklopentakarboxylovej:
3- ( 3-cyklopentylkarbamoylbenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl
3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3- (3-izobutyrylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s metylesterom kyseliny chlórmravčej:
3-(3-metoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom kyseliny chlórmravčej:
3-(3-etoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, amorfný, s metoxalylchoridom:
3-(3-metoxalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s chlórformamidom:
3-(3-ureidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(3-butyrylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-l ,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(3-pentanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(3-hexanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(3-pentafluórpropionylaminobenzyl)-5-(3,4-dimetoxyfenyl) -6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3-(3-pivalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-fluórmet oxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl) -5-(3-fluórmetoxy-4-metoxyfenyl)-6 etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl) etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3—(4—hexanoylaminobenzyl)-5—(3—fluórmetoxy—4—metoxyfenyl)— etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3-fluórmetoxy-4metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazin-2-on, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3-fluórmetoxy-4-metoxyfenyl)-6 etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3-fluórmetoxy-4-metoxy fenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on,
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3-difluórmetoxy-4-metoxyfenyl)-6-etyl33
3,6-dihydro-l,3,4-tiadiazín-2-on, s butyrylchloridom:
3- (4-butyrylaminobenzyl) -5- (3-difluórmetoxy-4-metoxyfenyl) -6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3- (4-pentanoylaminobenzyl) -5- (3-difluórmetoxy-4-metoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazin-2-on, s hexanoylchloridom:
3- ( 4-hexanoylaminobenzyl) -5- ( 3-dif luórmetoxy-4-metoxyf enyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3- (4-pentaf luórpropionylaminobenzyl) -5- (3-difluórmetoxy-4-metoxyf enyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazin-2-on, s pivalylchloridom:
3-(4-pivalylaminobenzyl )-5-( 3-dif luórmetoxy-4-metoxyf enyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3- (4-cyklopentylkarbamoylbenzyl )-5-( 3-difluórmetoxy-4-metoxyf enyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazin-2-on,
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-trifluór metoxy-4-metoxyfenyl) -6-etyl-3,6-dihydro-l, 3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3- (4-trif luóracetamidobenzyl) -5- (3-trifluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3- ( 4-acetamidobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3- (4-propionylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3- (4-etoxykarbonylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl) 35
6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3-trifluórmetoxy-4metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3-trifluórmetoxy-4-metoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3- (4-cyklopentylkarbamoylbenzyl)-5-(3-trifluórmetoxy-4-metoxy fenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on,
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-metoxy4- fluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6-etyl3,6-dihydro-l, 3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6-etyl-3,6dihydro-1,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyf enyl )-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3-metoxy-4-fluórmetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3-metoxy-4-fluórmetoxy37 fenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on,
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-metoxy-4 difluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylsulfonylchloridom;
3-(4-metylsulfonamidobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3- (4-izobutyrylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3—(4-ureidobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, s butyrylchloridom:
3- (4-butyrylaminobenzyl )-5-( 3-metoxy-4-dif luórmetoxyf enyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3- (4-pentafluórpropionylaminobenzyl)-5-(3-metoxy-4-difluór metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3- (4-pivalylaminobenzyl)-5-(3-metoxy-4-difluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazin-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3-metoxy-4-difluórmetoxyf enyl )-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-metoxy-4 trifluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3- (4-trifluóracetamidobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)39
6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3- (4-metylsulfonamidobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-( 4-metoxykarbonylaminobenzyl )-5- (3-metoxy-4-trif luórmetoxyf enyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3- (4-etoxykarbonylaminobenzyl) -5- (3-metoxy-4-trif luórmetoxyf enyl) 6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3- ( 4-ureidobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyf enyl )-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3-metoxy-4-trifluórmetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on,
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3,4-dimetoxy fenyl)-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro
1,3,4-tiadiazín-2-on, s teplotou topenia 176°C, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l ,3,4tiadiazín-2-on, s teplotou topenia 186°C, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s teplotou topenia 186°C, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro41
1,3,4-tiadiazín-2-on, s teplotou topenia 137°C, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl) -3 ,6-dihydro-1,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l ,3,4-tiadiazín-2-on, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6 dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3,4-dimetoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on,
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-etoxy-4metoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on, s teplotou topenia 188°C, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6-dihydro-1,3,4-tiadiazín-2-on, s teplotou topenia 184°c, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on, s teplotou topenia 95°C, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6-dihydro
1,3,4-tiadiazín-2-on, s metoxalylchloridom:
3- (4-metoxalylaminobenzyl) -5- (3-etoxy-4-metoxyfenyl) -3,6-dihydro-1,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidobenzyl)-5-( 3-etoxy-4-metoxyfenyl )-3,6-dihydro-l ,3,4tiadiazín-2-on, s butyrylchloridom:
3- (4-butyrylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-etoxy-4-metoxyfenyl)-3,6-dihydro-l ,3,4-tiadiazin-2-on, s hexanoylchloridom:
3- (4-hexanoylaminobenzyl) -5- (3-etoxy-4-metoxyfenyl) -3,6-dihydro-l ,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3- (4-pentaf luórpropionylaminobenzyl) -5- (3-etoxy-4-metoxyf enyl) 3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3- (4-cyklopentylkarbamoylbenzyl) -5- ( 3-etoxy-4-metoxyfenyl )-3,6dihydro-1,3,4-tiadiazín-2-on,
Obdobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-cyklopentyl oxy-4-metoxyf enyl) -3,6-dihydro-l, 3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-( 4-trif luóracetamidobenzyl )-5-( 3-cyklopentyloxy-4-metoxyfenyl)3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 196°C, s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-3,6dihydro-1,3,4-tiadiazín-2-on, s metylsulfonylchloridom:
3-(4-metylsulfonamidobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 103°C, s izobutyrylchloridom:
3-(4-izobutyrylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)
3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 72°C, s pivalylchloridom:
3-(4-pivalylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)3,6-dihydro-l,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)3,6-dihydro-l,3,4-tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)3.6- dihydro-l,3,4-tiadiazin-2-on, s pentanoylchloridom:
3-(4-pentanoylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)3.6- dihydro-l,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminobenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)3,6-dihydro-l,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(4-pentafluórpropionylaminobenzyl)-5-(3-cyklopentyloxy-4-met oxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3-(4-cyklopentylkarbamoylbenzyl)-5-(3-cyklopentyloxy-4-metoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou 3-(4-aminofénetyl)-5-(3,4-dimet oxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(4-trifluóracetamidofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-1,3,4-tiadiazín-2-on, s acetylchloridom:
3-(4-acetamidofénetyl)-5-(3,4-dimetoxyfenyl) -3,6-dihydro-l,3,4 tiadiazín-2-on, s metylsulfonylchloridom:
3-(4-metylsulfonamidofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-on, s propionylchloridom:
3-( 4-propionylaminofénetyl )-5- (3,4-dimetoxyfenyl) -3,6-dihyd'ro1,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(4-izobutyrylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro
1,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(4-metoxykarbonylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l ,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3-(4-etoxykarbonylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-1,3,4-tiadiazxn-2-on, s pivalylchloridom:
3-(4-pivalylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(4-metoxalylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s chlórformamidom:
3-(4-ureidofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l ,3,4tiadiazín-2-on, s butyrylchloridom:
3-(4-butyrylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(4-pentanoylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(4-hexanoylaminofénetyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro- 47 1,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3- (4-pentaf luórpropionylaminof énetyl) -5- ( 3,4-dimetoxyf enyl) 3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3- (4-cyklopentylkarbamoylf enetyl) -5- (3,4-dimetoxyf enyl )-3,6dihydro-1,3,4-tiadiazín-2-on.
Obdobne sa získa reakciou 3-(3-aminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4-tiadiazín-2-onu s trifluóracetylchloridom:
3-(3-trifluóracetamidobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro
1,3,4-tiadiazín-2-on, s teplotou topenia 196°C, s acetylchloridom:
3- (3-acetamidobenzyl )-5-(3,4-dimetoxyf enyl) -3,6-dihydro-l ,3,4tiadiazín-2-on, s metylsulfonylchloridom:
3- ( 3-metylsulf onamidobenzyl) -5- ( 3,4-dimetoxyf enyl) -3,6-dihydro1,3,4-tiadiazín-2-on, s propionylchloridom:
3- ( 3-propionylaminobenzyl )-5-(3,4-dimetoxyf enyl) -3,6-dihydro1,3,4-tiadiazín-2-on, s izobutyrylchloridom:
3-(3-izobutyrylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s metylesterom chlórmravčej kyseliny:
3-(3-metoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6dihydro-l,3,4-tiadiazín-2-on, s etylesterom chlórmravčej kyseliny:
3- (3-etoxykarbonylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-1,3,4-tiadiazín-2-on, s pivalylchloridom:
3- ( 3-pivalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s metoxalylchloridom:
3-(3-metoxalylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s chlórformamidom:
3-(3-ureidobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4-tia diazín-2-on, s butyrylchloridom:
3- (3-butyrylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s pentanoylchloridom:
3-(3-pentanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s hexanoylchloridom:
3-(3-hexanoylaminobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro1,3,4-tiadiazín-2-on, s pentafluórpropionylchloridom:
3-(3-pentafluórpropionylaminobenzyl)-5-(3,4-dimetoxyfenyl)3,6-dihydro-l,3,4-tiadiazín-2-on, s chloridom cyklopentánkarboxylovej kyseliny:
3-(3-cyklopentylkarbamoylbenzyl)-5-(3,4-dimetoxyfenyl)-3,6dihydro-l,3,4-tiadiazín-2-on.
Príklad 7
Roztok 1,4 g 3-(4-aminobenzyl)-5-(3,4-dimetoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu v 60 ml dichlórmetánu a 1 ml trietylamínu sa zmieša za chladenia a miešania s 1,5 ml butylbromidu, rozpusteného v 20 ml dichlórmetánu a mieša sa počas troch hodín. Rozpúšťadlo sa odstráni a spracuje sa obvyklým spôsobom. Získa sa 3-(4-N,N-dibutylaminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-on.
Príklad 8
Roztok 1,4 g 3-(4-propionylaminobenzyl)-5-(3-hydroxy-4metoxyfenyl)-6-etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu [získatelného reakciou 3-(4-aminobenzyl)-5-(3-hydroxy-4-metoxyfenyl)-6etyl-3,6-dihydro-l,3,4-tiadiazín-2-onu s propionylchloridom] v tetrahydrofuráne sa po pridaní jedného ekvivalentu trifluórmetyljodídu udržuje na teplote varu počas dvoch hodín. Rozpúšťadlo sa odstráni a spracuje sa obvyklým spôsobom. Získa sa 3-(4-propionyl aminobenzyl)-5-(3-trifluór-metoxy-4-metoxyfenyl)-6-etyl-3,6-dihydro-1,3,4-tiadiazín-2-on.
Príklad 9
Podobne ako podlá príkladu 4 sa získa reakciou
3-(2-nitrobenzyl)-5-(3,4-dimetoxy)-3,6-dihydro-l,3,4-tiadiazín2- onu:
3- (2-aminobenzyl)-5-(3,4-dimetoxy)-3,6-dihydro-l,3,4-tiadiazín2- on (E), s teplotou topenia 127°C,
3- (4-nitrobenzyl)-5-(3-propoxy-4-metoxy)-3,6-dihydro-l,3,4-tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-propoxy-4-metoxy)-3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 125°C,
3-(4-nitrobenzyl)-5-(3-cyklopentyloxy-4-metoxy)-3,6-dihydro1.3.4- tiadiazín-2-onu:
3-(4-aminobenzyl)-5-(3-cyklopentyloxy-4-metoxy)-3,6-dihydro1.3.4- tiadiazín-2-on, s teplotou topenia 123°C.
Príklad 10
Podobne ako podlá príkladu 6 sa získa reakciou E * s acetylchloridom:
3-(2-acetamidobenzyl)-5-(3,4-dimetoxy)-3,6-dihydro-l,3,4-tiadiazín-2-on, s teplotou topenia 210°C, s trifluóracetylchloridom:
3-(2-trifluóracetamidobenzyl)-5-(3,4-dimetoxy)-3,6-dihydro1.3.4- tiadiazín-2-on, s teplotou topenia 200“C.
Podobne sa získa reakciou 3-(4-aminobenzyl)-5-(3-propoxy-4metoxy)-3,6-dihydro-l,3,4-tiadiazín-2-onu • s acetylchloridom:
3-(4-acetamidobenzyl)-5-(3-propoxy-4-metoxy)-3,6-dihydro-l,3,4e tiadiazín-2-on, bez definovanej teploty topenia, amorfný, s propionylchloridom:
3-(4-propionylaminobenzyl)-5-(3-propoxy-4-metoxy)-3,6-dihydro1.3.4- tiadiazín-2-on, s teplotou topenia 150°C, s trifluóracetylchloridom:
3-(4-trifluóracetamidobenzyl)-5-(3-propoxy-4-metoxy)-3,6-dihydro
1,3,4-tiadiazín-2-on, s teplotou topenia 167°C.
Nasledujúce príklady objasňujú farmaceutické prostriedky podlá vynálezu.
Príklad A Injekčné fioly
Roztok 100 g účinnej zlúčeniny všeobecného vzorca I a 5 g dinátriumhydrogenfosfátu v 3 litroch dvakrát destilovanej vody sa nastaví na hodnotu pH 6,5 2N kyselinou chlorovodíkovou, sterilné sa sfiltruje a plní sa do injekčných fiol a lyofilizuje sa za sterilných podmienok, fioly sa uzatvoria sterilným spôsobom. Každá injekčná fiola obsahuje 5 mg účinnej látky.
Príklad B Čapíky
Roztopí sa 20 g účinnej zlúčeniny všeobecného vzorca I so 100 g sójového lecitínu a s 1400 g kakaového masla, zmes sa leje do foriem a nechá sa schladnút. Každý čapík obsahuje 20 mg účinnej látky.
Príklad C Roztok
Pripraví sa roztok 1 g účinnej zlúčeniny všeobecného vzorca I, 9,38 g dihydrátu nátriumdihydrogenfosfátu, 28,48 g dinátriumhydrogenfosfátu s 12 molekulami vody a 0,1 g benzalkóniumchloridu v 940 ml dvakrát destilovanej vody. Hodnota pH roztoku sa upraví na 6,8, doplní sa na jeden liter a sterilizuje sa ožiarením. Roztok sa používa ako očné kvapky.
Príklad D Masť
Zmieša sa 500 mg účinnej zlúčeniny všeobecného vzorca I s 99,5 g vazelíny za aseptických podmienok.
Príklad E Tablety
Zmes 1 kg účinnej zlúčeniny všeobecného vzorca I, 4 kg laktózy, 1,2 kg zemiakového škrobu, 0,2 kg mastenca a 0,1 kg stearanu horečnatého sa známy spôsobom lisovaním spracuje na tablety, pričom každá tableta obsahuje 10 mg účinnej látky.
Príklad F Dražé
Podobne ako podlá príkladu E sa lisujú tablety, ktoré sa potom známym spôsobom opatria povlakom zo sacharózy, zemiakového škrobu, mastenca, tragantu a farbiva.
Príklad G Kapsuly kg účinnej látky všeobecného vzorca I sa plní známym spôsobom do tvrdých želatínových kapsúl tak, aby každá kapsula obsahovala 20 mg účinnej látky.
Príklad H Ampulky
Roztok 1 kg účinnej látky všeobecného vzorca I v 60 litroch dvakrát destilovanej vody sa sterilné filtruje, plní sa do ampuliek, za sterilných podmienok sa lyofilizuje a za sterilných podmienok sa uzavrie. Každá ampulka obsahuje 10 mg účinnej látky.
Priemyslová využiteínosť
Derivát arylalkyltiadiazinónu brzdí fosfodiesterázu IV a je preto použitelný na výrobu farmaceutických prostriedkov pre ošetrovanie astmatických ochorení a je tiež použitelný ako medziprodukt na výrobu ďalších liečiv.
Claims (7)
- , PATENTOVÉ NÁROKY1. Derivát arylalkyltíadiazinónu všeobecného vzorca I kde znamenáR1 a R2 na sebe nezávisle atóm vodíka alebo skupinu symbolu A,R3 a R4 na sebe nezávisle hydroxylovú. skupinu, skupinu vzorca-OR10, -S-R10, -SO-R10, —S02—R10, Hal, metyléndioxyskupinu, nitroskupinu, skupinu -NH
- 2, -NHR10 alebo -NR10R11, r5 fenylovú skupinu nesubstituovanú alebo substituovanú jedným alebo dvoma substituentmi symbolu R6 a/alebo R7,.Q chýba alebo žnamená alkylénovú skupinu s 1 až 6 atómami uhlíka,R6 a R7 vždy na sebe nezávisle skupinu -nh2, -NR8R9, -NHR10,-NR1^11, nitroskupinu, Hal, kyanoskupinu, skupinu -0A, -COOH alebo -COOA, & a R9 vždy na sebe nezávisle atóm vodíka, acylovú skupinu s i až 8 atómami uhlíka, prípadne substituovanú jedným až piatimi' atómami fluóru a/alebo chlóru, skupinu -COOA,-S-A, -S02-A, -SOA, CONH2, -CONHA, -CONA2, -CO-COOH,-CO-COOA, -CO- CONH2, -CO-CONHA alebo -CO-CONA2,Á alkylovú skupinu s 1 až 6 atómami uhlíka prípadne substituovanú jedným až piatimi atómami fluóru a/alebo chlóru, r10 a R11vždy na sebe nezávisle A, cykloalkylovú skupinu s 3 až 7 atómami uhlíka, metyléncykloalkylovú skupinu s 4 až 8 atómami uhlíka, alebo alkenylovú skupinu s 2 až 8 atómami uhlíka aHal atóm fluóru, chlóru, brómu alebo jódu • a jeho fyziologicky vhodná sol.» 2. Derivát arylalkyltiadiazinónu podlá nároku 1 všeobecného vzorca I vo forme enantioméru.
- 3. Derivát arylalkyltiadiazinónu podlá nároku 1 všeobecného vzorca I, ktorým jea) 3-(4-nitrobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on,b) 3-(4-aminobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on, * c) 3-(4-trifluóracetamidobenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl3,6-dihydro-l,3,4-tiadiazín-2-on, »d) 3-(4-acetamidobenzyl)-5-(3,4-dimetoxyfenyl)-3,6-dihydro-l,3,4 tiadiazín-2-on,e) 3-(4-metoxybenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro1,3,4-tiadiazín-2-on,f) 3-(2,6-dichlórbenzyl)-5-(3,4-dimetoxyfenyl)-6-etyl-3,6-dihydro-l ,3,4-tiadiazín-2-on.
- 4. Spôsob prípravy derivátu arylalkyltiadiazinónu podlá nároku 1 všeobecného vzorca I a jeho solí, vyznačuj úci sa t ý m , že sa zlúčenina všeobecného vzorca II kde R , R , R a R majú v nároku 1 uvedený význam, nechava reagovať so zlúčeninou všeobecného vzorca IIIR5 - Q - X *(III) kde R5 a Q má v nároku 1 uvedený význam a kde znamená X atóm chlóru, brómu, hydroxylovú skupinu alebo reaktívnu esterifikovanú hydroxylovú skupinu, alebo sa v zlúčenine všeobecného vzorca I zvyšok symbolu R5 premieňa na iný zvyšok symbolu R5 tým, že sa redukuje nitroskupina, alkyluje alebo acyluje sa primárna alebo sekundárna aminoskupina alebo sa hydrolyzuje kyanoskupina, a/alebo sa zlúčenina zodpovedajúca všeobecnému vzorci I, ktorá má však miesto skupiny symbolu R3 a/alebo R4 jednu alebo dve volné hydroxylové skupiny, necháva reagovať so zlúčeninou všeobecného vzorca R3-X prípadne R4-X, kde R3, R4 a X majú v nároku 1 uvedený význam, a/alebo sa zásada všeobecného vzorca I premieňa pôsobením kyseliny na zodpovedajúcu soľ.
- 5. Spôsob prípravy farmaceutického prostriedku, vyznačujúci sa t ý m, že sa derivát arylalkyltiadiazinónu podľa nároku 1 všeobecného vzorca I a/alebo jeho fyziologicky vhodná soľ spracováva na vhodnú dávkovaciu formu spolu s aspoň jedným pevným kvapalným alebo polokvapalným nosičom alebo s pomocnou látkou.
- 6. Farmaceutický prostriedok, vyznačujúci ,s a tým, že obsahuje ako účinnú látku aspoň jeden derivát arylalkyltiadiazinónu podía nároku 1 všeobecného vzorca I a/alebo jeho fyziologicky vhodnú sol.
- 7. Použitie derivátu arylalkyltiadiazinónu podlá nároku 1 všeobecného vzorca I a/alebo jeho fyziologicky vhodnej soli na výrobu Ä farmaceutického prostriedku pre liečbu chorôb.* Použitie derivátu arylalkyltiadiazinónu podlá nároku 1 všeobecného vzorca I a/alebo jeho fyziologicky vhodnej soli na liečbu chorôb.
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CN1235589C (zh) * | 2001-02-12 | 2006-01-11 | 默克专利股份公司 | 4型磷酸二酯酶抑制剂在制备治疗心肌疾病药物中的应用 |
DE10150517A1 (de) * | 2001-10-12 | 2003-04-17 | Merck Patent Gmbh | Verwendung von Phosphodiesterase IV-Inhibitoren |
CZ2004516A3 (cs) * | 2001-10-31 | 2004-08-18 | Merckápatentágmbh | Inhibitor fosfodiesterázy typu @Ź jeho kombinace s jinými drogami a jeho použití |
WO2005075437A1 (en) * | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Pyridazinone derivatives and their use as pde4 inhibitors |
WO2005075456A1 (en) | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | 2-(piperidin-4-yl) -4, 5-dihydro-2h-pyridazin-3-one derivatives as pde4 inhibitors |
DE102005055355A1 (de) * | 2005-11-21 | 2007-10-31 | Merck Patent Gmbh | 3,6-Dihydro-2-oxo-6H-[1,3,4]thiadiazinderivate |
DE102005055354A1 (de) * | 2005-11-21 | 2007-10-31 | Merck Patent Gmbh | Substituierte 5-Phenyl-3,6-dihydro-2-oxo-6H-[1,3,4]thiadiazine |
US8418387B2 (en) * | 2009-11-13 | 2013-04-16 | Manufacturing Resources International, Inc. | Isolated access assembly for back-to-back electronic display and static display |
RU2597764C2 (ru) * | 2014-12-16 | 2016-09-20 | Федеральное государственное автономное образовательное учреждение высшего образования "Уральский федеральный университет имени первого Президента России Б.Н. Ельцина" | Применение соединений класса 1,3,4-тиадиазина в качестве средства коррекции экспериментального аллоксанового сахарного диабета |
RU2659574C2 (ru) * | 2016-12-27 | 2018-07-05 | федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургская государственная химико-фармацевтическая академия" Министерства здравоохранения Российской Федерации (ФГБОУ ВО СПХФА Минздрава России) | 6-(3,5-Дифенил-1,3,4-тиадиазол-2(3Н)-илиден)-2,4-дифенил-4Н-1,3,4-тиадиазин-5-он и способ его получения |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU614965B2 (en) * | 1987-06-06 | 1991-09-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Thiadiazinones |
DE3719031A1 (de) * | 1987-06-06 | 1988-12-22 | Merck Patent Gmbh | 5-(1,2,3,4-tetrahydrochinolyl)-3,6-dihydro-1,3,4-thiadiazin-2-one |
GB8816944D0 (en) * | 1988-07-15 | 1988-08-17 | Sobio Lab | Compounds |
DE4134893A1 (de) * | 1991-10-23 | 1993-04-29 | Merck Patent Gmbh | Thiadiazinone |
DE4310699A1 (de) * | 1993-04-01 | 1994-10-06 | Merck Patent Gmbh | Thiadiazinone |
DE19533975A1 (de) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
-
1995
- 1995-01-28 DE DE19502699A patent/DE19502699A1/de not_active Withdrawn
- 1995-12-29 HU HU9503933A patent/HU219361B/hu not_active IP Right Cessation
-
1996
- 1996-01-15 ES ES96100468T patent/ES2160184T3/es not_active Expired - Lifetime
- 1996-01-15 AT AT96100468T patent/ATE202775T1/de not_active IP Right Cessation
- 1996-01-15 EP EP96100468A patent/EP0723962B1/de not_active Expired - Lifetime
- 1996-01-15 SI SI9630339T patent/SI0723962T1/xx unknown
- 1996-01-15 DE DE59607188T patent/DE59607188D1/de not_active Expired - Fee Related
- 1996-01-15 DK DK96100468T patent/DK0723962T3/da active
- 1996-01-15 PT PT96100468T patent/PT723962E/pt unknown
- 1996-01-17 UA UA96010217A patent/UA42731C2/uk unknown
- 1996-01-22 AU AU42111/96A patent/AU705639B2/en not_active Ceased
- 1996-01-25 TW TW085100850A patent/TW342389B/zh active
- 1996-01-26 JP JP03122296A patent/JP3878237B2/ja not_active Expired - Fee Related
- 1996-01-26 KR KR1019960001653A patent/KR100384726B1/ko not_active IP Right Cessation
- 1996-01-26 ZA ZA96630A patent/ZA96630B/xx unknown
- 1996-01-26 PL PL96312489A patent/PL184486B1/pl unknown
- 1996-01-26 RU RU96101802/04A patent/RU2161613C2/ru not_active IP Right Cessation
- 1996-01-26 US US08/592,659 patent/US5747489A/en not_active Expired - Fee Related
- 1996-01-26 CA CA002168193A patent/CA2168193C/en not_active Expired - Fee Related
- 1996-01-26 SK SK123-96A patent/SK281052B6/sk unknown
- 1996-01-26 NO NO960352A patent/NO305835B1/no unknown
- 1996-01-26 CZ CZ1996251A patent/CZ286635B6/cs not_active IP Right Cessation
-
1998
- 1998-01-20 US US09/008,812 patent/US6025354A/en not_active Expired - Fee Related
-
2001
- 2001-08-07 GR GR20010401195T patent/GR3036343T3/el not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CZ286635B6 (cs) | 2000-05-17 |
NO960352L (no) | 1996-07-29 |
CZ25196A3 (en) | 1996-08-14 |
PT723962E (pt) | 2001-10-31 |
CA2168193A1 (en) | 1996-07-29 |
PL184486B1 (pl) | 2002-11-29 |
JPH08231522A (ja) | 1996-09-10 |
ZA96630B (en) | 1996-08-15 |
HU9503933D0 (en) | 1996-03-28 |
US6025354A (en) | 2000-02-15 |
NO305835B1 (no) | 1999-08-02 |
AU705639B2 (en) | 1999-05-27 |
KR100384726B1 (ko) | 2003-08-25 |
CA2168193C (en) | 2006-08-15 |
SI0723962T1 (sk) | 2001-12-31 |
EP0723962A1 (de) | 1996-07-31 |
GR3036343T3 (en) | 2001-11-30 |
JP3878237B2 (ja) | 2007-02-07 |
HUT73981A (en) | 1996-10-28 |
KR960029327A (ko) | 1996-08-17 |
RU2161613C2 (ru) | 2001-01-10 |
HU219361B (en) | 2001-03-28 |
DK0723962T3 (da) | 2001-10-29 |
SK281052B6 (sk) | 2000-11-07 |
TW342389B (en) | 1998-10-11 |
DE59607188D1 (de) | 2001-08-09 |
ES2160184T3 (es) | 2001-11-01 |
DE19502699A1 (de) | 1996-08-01 |
PL312489A1 (en) | 1996-08-05 |
AU4211196A (en) | 1996-08-08 |
US5747489A (en) | 1998-05-05 |
EP0723962B1 (de) | 2001-07-04 |
ATE202775T1 (de) | 2001-07-15 |
UA42731C2 (uk) | 2001-11-15 |
NO960352D0 (no) | 1996-01-26 |
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