CZ70594A3 - Thiadiazinones - Google Patents
Thiadiazinones Download PDFInfo
- Publication number
- CZ70594A3 CZ70594A3 CZ94705A CZ70594A CZ70594A3 CZ 70594 A3 CZ70594 A3 CZ 70594A3 CZ 94705 A CZ94705 A CZ 94705A CZ 70594 A CZ70594 A CZ 70594A CZ 70594 A3 CZ70594 A3 CZ 70594A3
- Authority
- CZ
- Czechia
- Prior art keywords
- dihydro
- ethyl
- thiadiazin
- formula
- compound
- Prior art date
Links
- -1 methylenedioxy Chemical group 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- KFJJKQPQLLMDIQ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-[3-(dimethylamino)propyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=NN(CCCN(C)C)C(=O)SC1 KFJJKQPQLLMDIQ-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- BMGFMYTZEXBTEJ-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-6-ethyl-6H-1,3,4-thiadiazin-2-one Chemical compound COC=1C=C(C=CC=1OC)N1C(SC(C=N1)CC)=O BMGFMYTZEXBTEJ-UHFFFAOYSA-N 0.000 claims 1
- HIZIMUCPUGDGLO-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-(dimethylamino)-6,6-diethyl-1,3,4-thiadiazin-2-one Chemical compound CCC1(CC)SC(=O)N(N(C)C)N=C1C1=CC=C(OC)C(OC)=C1 HIZIMUCPUGDGLO-UHFFFAOYSA-N 0.000 claims 1
- MTVLYWXDQXLLQF-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3-(3-morpholin-4-ylpropyl)-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)N1CCCN1CCOCC1 MTVLYWXDQXLLQF-UHFFFAOYSA-N 0.000 claims 1
- YSODXONESAHCBL-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3-(3-piperidin-1-ylpropyl)-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)N1CCCN1CCCCC1 YSODXONESAHCBL-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 abstract description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- PIAZYBLGBSMNLX-UHFFFAOYSA-N 4-(3-chloropropyl)morpholine Chemical compound ClCCCN1CCOCC1 PIAZYBLGBSMNLX-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 description 7
- MLGXDYNVEUDWHZ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC)C(OC)=C1 MLGXDYNVEUDWHZ-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 6
- KQUGNOYYBNPZBP-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC(F)F)C(OC)=C1 KQUGNOYYBNPZBP-UHFFFAOYSA-N 0.000 description 6
- SQXAROYMYJEJTP-UHFFFAOYSA-N 6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OCF)C(OC)=C1 SQXAROYMYJEJTP-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- WTGUUGJZRZUIAU-UHFFFAOYSA-N 1,3,4-thiadiazin-2-one Chemical compound O=C1N=NC=CS1 WTGUUGJZRZUIAU-UHFFFAOYSA-N 0.000 description 5
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 5
- LPVPITJSBXSDHT-UHFFFAOYSA-N 3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound O=C1NN=CCS1 LPVPITJSBXSDHT-UHFFFAOYSA-N 0.000 description 5
- LVKFSJWCSIBHMY-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C1=NNC(=O)SC1CC LVKFSJWCSIBHMY-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 4
- LELNKYUZHIIYJL-UHFFFAOYSA-N 5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC(C=2C(SC(=O)NN=2)CC)=C1 LELNKYUZHIIYJL-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002775 capsule Substances 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
- 239000002904 solvent Substances 0.000 description 4
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CRVAECICDQAMRA-UHFFFAOYSA-N 6-ethyl-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC(F)(F)F)C(OC)=C1 CRVAECICDQAMRA-UHFFFAOYSA-N 0.000 description 3
- QYRSKTNORZKLKH-UHFFFAOYSA-N 6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-3-(3-pyrrolidin-1-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)SC(=O)N1CCCN1CCCC1 QYRSKTNORZKLKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 239000013543 active substance Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012154 double-distilled water Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- SPRTXTPFQKHSBG-UHFFFAOYSA-N 1-(3-chloropropyl)pyrrolidine Chemical compound ClCCCN1CCCC1 SPRTXTPFQKHSBG-UHFFFAOYSA-N 0.000 description 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 2
- 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 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 235000011007 phosphoric acid Nutrition 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- GFNCKWVXDTZLDU-UHFFFAOYSA-N 2-bromo-1-(3,4-dimethoxyphenyl)butan-1-one Chemical compound CCC(Br)C(=O)C1=CC=C(OC)C(OC)=C1 GFNCKWVXDTZLDU-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- UWMSQWJUWUFTFQ-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-5-(3-ethoxy-4-methoxyphenyl)-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC(C=2C(SC(=O)N(CCN(C)C)N=2)CC)=C1 UWMSQWJUWUFTFQ-UHFFFAOYSA-N 0.000 description 1
- WVENUNNSYGZSCX-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C1=NN(CCN(C)C)C(=O)SC1CC WVENUNNSYGZSCX-UHFFFAOYSA-N 0.000 description 1
- DDZJWAMNIXJXOT-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-6-ethyl-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCN(C)C)N=C1C1=CC=C(OC(F)(F)F)C(OC)=C1 DDZJWAMNIXJXOT-UHFFFAOYSA-N 0.000 description 1
- AXCBBCDRIZPVBW-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCN(C)C)N=C1C1=CC=C(OCF)C(OC)=C1 AXCBBCDRIZPVBW-UHFFFAOYSA-N 0.000 description 1
- DYQZKUNREPHHEE-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C1=NN(CCCN(C)C)C(=O)SC1CC DYQZKUNREPHHEE-UHFFFAOYSA-N 0.000 description 1
- BIJUKXDAJSUOME-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-5-[3-methoxy-4-(1,1,2-trifluoroethoxy)phenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC(F)(F)CF)C(OC)=CC(C=2CSC(=O)N(CCCN(C)C)N=2)=C1 BIJUKXDAJSUOME-UHFFFAOYSA-N 0.000 description 1
- VUQLCNWGPUYVGN-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC(F)(F)F)C(OC)=CC(C=2CSC(=O)N(CCCN(C)C)N=2)=C1 VUQLCNWGPUYVGN-UHFFFAOYSA-N 0.000 description 1
- HUHMZTBJOITPGG-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-5-[4-(trifluoromethoxy)phenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1SC(=O)N(CCCN(C)C)N=C1C1=CC=C(OC(F)(F)F)C=C1 HUHMZTBJOITPGG-UHFFFAOYSA-N 0.000 description 1
- BIGOISUWSBDWHQ-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-6-ethyl-5-(4-hydroxy-3-methoxyphenyl)-6H-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCCN(C)C)N=C1C1=CC=C(O)C(OC)=C1 BIGOISUWSBDWHQ-UHFFFAOYSA-N 0.000 description 1
- MTSZSWCBAPZPDC-UHFFFAOYSA-N 3-[3-(dimethylamino)propyl]-6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCCN(C)C)N=C1C1=CC=C(OCF)C(OC)=C1 MTSZSWCBAPZPDC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LLUMPPXMWXLWFP-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=NNC(=O)SC1 LLUMPPXMWXLWFP-UHFFFAOYSA-N 0.000 description 1
- FYXVFOSDEZAHNQ-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-3-[2-(dimethylamino)ethyl]-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCN(C)C)N=C1C1=CC=C(OC)C(OC)=C1 FYXVFOSDEZAHNQ-UHFFFAOYSA-N 0.000 description 1
- IWFIRSLAUSHTOT-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-(2-morpholin-4-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CCN1CCOCC1 IWFIRSLAUSHTOT-UHFFFAOYSA-N 0.000 description 1
- OTBDRVXSAMCBJS-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-(2-piperidin-1-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CCN1CCCCC1 OTBDRVXSAMCBJS-UHFFFAOYSA-N 0.000 description 1
- MCGLEVJQMVXHEY-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-(2-pyrrolidin-1-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CCN1CCCC1 MCGLEVJQMVXHEY-UHFFFAOYSA-N 0.000 description 1
- MLNKJLQIBLQDRR-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-(3-morpholin-4-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CCCN1CCOCC1 MLNKJLQIBLQDRR-UHFFFAOYSA-N 0.000 description 1
- GTPMUWUIBOOOMG-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-6-ethyl-3-(3-piperidin-1-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC)=CC=2)C(CC)SC(=O)N1CCCN1CCCCC1 GTPMUWUIBOOOMG-UHFFFAOYSA-N 0.000 description 1
- XEEBKGKUBYBKPP-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3-(2-morpholin-4-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C(C(SC1=O)CC)=NN1CCN1CCOCC1 XEEBKGKUBYBKPP-UHFFFAOYSA-N 0.000 description 1
- GKPREBGIOSQFJV-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3-(2-piperidin-1-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C(C(SC1=O)CC)=NN1CCN1CCCCC1 GKPREBGIOSQFJV-UHFFFAOYSA-N 0.000 description 1
- SYMSUJREFJCDQX-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3-(2-pyrrolidin-1-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C(C(SC1=O)CC)=NN1CCN1CCCC1 SYMSUJREFJCDQX-UHFFFAOYSA-N 0.000 description 1
- XZMIAOKRPDZCPK-UHFFFAOYSA-N 5-(4-ethoxy-3-methoxyphenyl)-6-ethyl-3-(3-piperidin-1-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound C1=C(OC)C(OCC)=CC=C1C(C(SC1=O)CC)=NN1CCCN1CCCCC1 XZMIAOKRPDZCPK-UHFFFAOYSA-N 0.000 description 1
- CNLLVSMNUGPYIS-UHFFFAOYSA-N 5-[3,4-bis(chloromethoxy)phenyl]-3-[3-(dimethylamino)propyl]-6h-1,3,4-thiadiazin-2-one Chemical compound C1SC(=O)N(CCCN(C)C)N=C1C1=CC=C(OCCl)C(OCCl)=C1 CNLLVSMNUGPYIS-UHFFFAOYSA-N 0.000 description 1
- WQCICYCTQZYBGO-UHFFFAOYSA-N 5-[3-(difluoromethoxy)-4-methoxyphenyl]-3-[2-(dimethylamino)ethyl]-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCN(C)C)N=C1C1=CC=C(OC)C(OC(F)F)=C1 WQCICYCTQZYBGO-UHFFFAOYSA-N 0.000 description 1
- KYTOLIPSUUEDHP-UHFFFAOYSA-N 5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC)C(OC(F)F)=C1 KYTOLIPSUUEDHP-UHFFFAOYSA-N 0.000 description 1
- GQATTXAZLMOTDG-UHFFFAOYSA-N 5-[3-(difluoromethoxy)-4-methoxyphenyl]-6-ethyl-3-(3-piperidin-1-ylpropyl)-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)N1CCCN1CCCCC1 GQATTXAZLMOTDG-UHFFFAOYSA-N 0.000 description 1
- RUSIENVHDRWPAF-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-3-[2-(dimethylamino)ethyl]-6-ethyl-6h-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)N(CCN(C)C)N=C1C1=CC=C(OC(F)F)C(OC)=C1 RUSIENVHDRWPAF-UHFFFAOYSA-N 0.000 description 1
- XDKKOIONGCTABW-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3-(2-morpholin-4-ylethyl)-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)N1CCN1CCOCC1 XDKKOIONGCTABW-UHFFFAOYSA-N 0.000 description 1
- SKAWQOAVPHBAAS-UHFFFAOYSA-N 5-[4-(difluoromethoxy)-3-methoxyphenyl]-6-ethyl-3-(2-pyrrolidin-1-ylethyl)-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)N1CCN1CCCC1 SKAWQOAVPHBAAS-UHFFFAOYSA-N 0.000 description 1
- IAULXWITGWPKOG-UHFFFAOYSA-N 6-ethyl-3-(3-hydroxy-4-methoxyphenyl)-6H-1,3,4-thiadiazin-2-one Chemical compound OC=1C=C(C=CC=1OC)N1C(SC(C=N1)CC)=O IAULXWITGWPKOG-UHFFFAOYSA-N 0.000 description 1
- IBTYWTCFTPMDKH-UHFFFAOYSA-N 6-ethyl-5-(3-hydroxy-4-methoxyphenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC)C(O)=C1 IBTYWTCFTPMDKH-UHFFFAOYSA-N 0.000 description 1
- ZNWZLWCYXKWUAZ-UHFFFAOYSA-N 6-ethyl-5-(4-hydroxy-3-methoxyphenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(O)C(OC)=C1 ZNWZLWCYXKWUAZ-UHFFFAOYSA-N 0.000 description 1
- CPXUUFNSUYLFFJ-UHFFFAOYSA-N 6-ethyl-5-[3-(fluoromethoxy)-4-methoxyphenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC)C(OCF)=C1 CPXUUFNSUYLFFJ-UHFFFAOYSA-N 0.000 description 1
- NVNFACMSIXSMSM-UHFFFAOYSA-N 6-ethyl-5-[3-methoxy-4-(trifluoromethoxy)phenyl]-3-(2-morpholin-4-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OC(F)(F)F)=CC=2)C(CC)SC(=O)N1CCN1CCOCC1 NVNFACMSIXSMSM-UHFFFAOYSA-N 0.000 description 1
- NEPKGKLHSRJGKE-UHFFFAOYSA-N 6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-3-(2-piperidin-1-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)SC(=O)N1CCN1CCCCC1 NEPKGKLHSRJGKE-UHFFFAOYSA-N 0.000 description 1
- QVIIJXUZZLDTTJ-UHFFFAOYSA-N 6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-3-(2-pyrrolidin-1-ylethyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)SC(=O)N1CCN1CCCC1 QVIIJXUZZLDTTJ-UHFFFAOYSA-N 0.000 description 1
- YFVIWNGGQUVEDP-UHFFFAOYSA-N 6-ethyl-5-[4-(fluoromethoxy)-3-methoxyphenyl]-3-(3-piperidin-1-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OC)C(OCF)=CC=2)C(CC)SC(=O)N1CCCN1CCCCC1 YFVIWNGGQUVEDP-UHFFFAOYSA-N 0.000 description 1
- UVQWYEWSXFPRMW-UHFFFAOYSA-N 6-ethyl-5-[4-methoxy-3-(2,2,2-trifluoroethoxy)phenyl]-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound CCC1SC(=O)NN=C1C1=CC=C(OC)C(OCC(F)(F)F)=C1 UVQWYEWSXFPRMW-UHFFFAOYSA-N 0.000 description 1
- YLOHDGVWSHTDOW-UHFFFAOYSA-N 6-ethyl-5-[4-methoxy-3-(2,2,2-trifluoroethoxy)phenyl]-3-(3-morpholin-4-ylpropyl)-6h-1,3,4-thiadiazin-2-one Chemical compound N1=C(C=2C=C(OCC(F)(F)F)C(OC)=CC=2)C(CC)SC(=O)N1CCCN1CCOCC1 YLOHDGVWSHTDOW-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XFRUEQQXPHUJNC-UHFFFAOYSA-N N1(CCCCC1)CCN1C(SC(C(=N1)C1=CC(=C(C=C1)OC(F)F)OC)CC)=O.ClCCN1CCCCC1 Chemical compound N1(CCCCC1)CCN1C(SC(C(=N1)C1=CC(=C(C=C1)OC(F)F)OC)CC)=O.ClCCN1CCCCC1 XFRUEQQXPHUJNC-UHFFFAOYSA-N 0.000 description 1
- FIWGXUKTOXIPFY-UHFFFAOYSA-N N1=NC(O)=C(O)S(=O)C1C1=CC=CC=C1 Chemical class N1=NC(O)=C(O)S(=O)C1C1=CC=CC=C1 FIWGXUKTOXIPFY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 1
- 229960002105 amrinone Drugs 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 229940098165 atrovent Drugs 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001966 cerebroprotective effect Effects 0.000 description 1
- KEWHKYJURDBRMN-XSAPEOHZSA-M chembl2134724 Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-XSAPEOHZSA-M 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 229940082657 digitalis glycosides Drugs 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 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
- 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
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LNWHCOPMPXKPNZ-UHFFFAOYSA-N o-methyl n-aminocarbamothioate Chemical compound COC(=S)NN LNWHCOPMPXKPNZ-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 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
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 210000003540 papillary muscle Anatomy 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001629 suppression Effects 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
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 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 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005490 tosylate group Chemical group 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
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000008096 xylene Substances 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Pulmonology (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4310699A DE4310699A1 (de) | 1993-04-01 | 1993-04-01 | Thiadiazinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ70594A3 true CZ70594A3 (en) | 1994-12-15 |
Family
ID=6484473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ94705A CZ70594A3 (en) | 1993-04-01 | 1994-03-25 | Thiadiazinones |
Country Status (12)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19500558A1 (de) * | 1995-01-11 | 1996-07-18 | Merck Patent Gmbh | 3-Alkoxycarbonyl-thiadiazinone |
| DE19502699A1 (de) * | 1995-01-28 | 1996-08-01 | Merck Patent Gmbh | Arylalkyl-thiadiazinone |
| DE19533975A1 (de) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| US8153646B2 (en) * | 2000-08-10 | 2012-04-10 | Dart Neuroscience (Cayman) Ltd. | Phosphodiesterase 4 inhibitors for cognitive and motor rehabilitation |
| DK1355669T3 (da) * | 2000-08-10 | 2011-11-21 | Cold Spring Harbor Lab | Forbedret kognitiv træning |
| WO2002072103A1 (en) * | 2001-02-12 | 2002-09-19 | Merck Patent Gmbh | Use of type 4 phosphodiesterase inhibitors in myocardial diseases |
| DE10150517A1 (de) * | 2001-10-12 | 2003-04-17 | Merck Patent Gmbh | Verwendung von Phosphodiesterase IV-Inhibitoren |
| CN1578665A (zh) * | 2001-10-31 | 2005-02-09 | 默克专利股份公司 | 4型磷酸二脂酶抑制剂及其应用 |
| EP1716123A1 (en) * | 2004-02-04 | 2006-11-02 | Altana Pharma AG | Pyridazinone derivatives and their use as pde4 inhibitors |
| CA2554797C (en) | 2004-02-04 | 2012-09-04 | Altana Pharma Ag | 2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-one derivatives as pde4 inhibitors |
| DE102007041115A1 (de) * | 2007-08-30 | 2009-03-05 | Merck Patent Gmbh | Thiadiazinonderivate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4413713Y1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-04-26 | 1969-06-09 | ||
| JPS54135785A (en) * | 1978-04-12 | 1979-10-22 | Yoshitomi Pharmaceut Ind Ltd | Pyridazinone derivative and its preparation |
| US4495185A (en) * | 1981-11-12 | 1985-01-22 | Imperial Chemical Industries, Plc | 1,2,4-Triazin-3(2H) ones |
| US4489074A (en) * | 1982-11-12 | 1984-12-18 | Imperial Chemical Industries, Plc | 1,3,4-Thiadiazin-2-ones |
| EP0478195B1 (en) * | 1990-09-21 | 1999-05-26 | Rohm And Haas Company | Dihydropyridazinones and pyridazinones as fungicides |
-
1993
- 1993-04-01 DE DE4310699A patent/DE4310699A1/de not_active Withdrawn
-
1994
- 1994-03-19 EP EP94104349A patent/EP0618201A1/de not_active Withdrawn
- 1994-03-23 AU AU57983/94A patent/AU675488B2/en not_active Expired - Fee Related
- 1994-03-25 CZ CZ94705A patent/CZ70594A3/cs unknown
- 1994-03-28 JP JP6057099A patent/JPH072812A/ja active Pending
- 1994-03-29 NO NO941150A patent/NO941150L/no unknown
- 1994-03-30 CA CA002120301A patent/CA2120301A1/en not_active Abandoned
- 1994-03-30 CN CN94104074A patent/CN1101644A/zh active Pending
- 1994-03-30 TW TW083102744A patent/TW310326B/zh active
- 1994-03-31 US US08/220,657 patent/US5434149A/en not_active Expired - Fee Related
- 1994-03-31 SK SK385-94A patent/SK38594A3/sk unknown
- 1994-03-31 HU HU9400934A patent/HUT70543A/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5798394A (en) | 1994-10-06 |
| CA2120301A1 (en) | 1994-10-02 |
| NO941150L (no) | 1994-10-03 |
| TW310326B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1997-07-11 |
| AU675488B2 (en) | 1997-02-06 |
| HU9400934D0 (en) | 1994-06-28 |
| HUT70543A (en) | 1995-10-30 |
| US5434149A (en) | 1995-07-18 |
| SK38594A3 (en) | 1994-12-07 |
| CN1101644A (zh) | 1995-04-19 |
| NO941150D0 (no) | 1994-03-29 |
| EP0618201A1 (de) | 1994-10-05 |
| DE4310699A1 (de) | 1994-10-06 |
| JPH072812A (ja) | 1995-01-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2020343671B2 (en) | RIP1 inhibitory compounds and methods for making and using the same | |
| TWI791511B (zh) | 細胞凋亡誘導劑 | |
| KR101454936B1 (ko) | Ｂｃｌ 단백질과 결합 파트너의 상호작용을 억제하기 위한 화합물 및 방법 | |
| EP4188383A1 (en) | Sos1 inhibitors | |
| EP1277738A1 (en) | Condensed heteroaryl derivatives | |
| UA45325C2 (uk) | Бензонітрили та бензофториди, спосіб їх одержання, фармацевтична композиція, спосіб її отримання, спосіб боротьби з захворюваннями | |
| WO2008038175A2 (en) | Dithiolopyrrolones compounds and their therapeutic applications | |
| JP2010095550A (ja) | キノリン誘導体 | |
| CZ70594A3 (en) | Thiadiazinones | |
| MX2008007687A (es) | Compuestos y métodos para inhibir la interacción de proteínas bcl con compañeros enlazantes. | |
| WO2002016369A2 (en) | Novel macrocycles and uses thereof | |
| EP1507534A2 (en) | Compounds, compositions and methods | |
| KR100384726B1 (ko) | 아릴알킬-티아디아지논유도체 | |
| KR20150060610A (ko) | 다이하이드로피리미딘 유도체의 결정질 형태 | |
| CN114644634A (zh) | 一种吡咯衍生物及其制备方法和用途 | |
| US20090275650A1 (en) | 3-Acyl coumarins, thiochromones and quinolones and therapeutic uses thereof | |
| CZ321095A3 (en) | Heterocyclic compounds | |
| JPH04330078A (ja) | 抗緑内障剤としての置換チエノ［２，３−ｂ］［１，４］チアジン−６−スルホンアミド類 | |
| CA1207774A (en) | 1-phenylindazol-3-one compounds, a method of preparing them and pharmaceutical compositions containing these compounds | |
| CZ263692A3 (en) | Thiadiazinones, process of their preparation and pharmaceutical compositions based thereon | |
| HU205931B (en) | Process for producing pyrrolo-pyrimidine derivatives and pharmaceutically acceptable salts thereof and pharmaceutical compositions containing them as active components | |
| US3729477A (en) | Certain 4-(3-amino-2-hydroxypropoxy)-1,2,5-thiadiazole-3-carboxamides | |
| IL96168A (en) | History of 4-amidino as novel and 4-amidino pirano (C-3,2), preparation and pharmaceutical preparations containing them | |
| UA44249C2 (uk) | 3-алкоксикарбонілтіадіазинони, спосіб їх одержання, фармацевтична композиція, спосіб одержання фармацевтичних композицій | |
| US5504087A (en) | 1-phenoxy-2-propanol derivatives useful in treating hypertension and glaucoma |