NO813850L - Fremgangsmaate for fremstilling av terapeutisk aktive heterocykliske forbindelser - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive heterocykliske forbindelserInfo
- Publication number
- NO813850L NO813850L NO813850A NO813850A NO813850L NO 813850 L NO813850 L NO 813850L NO 813850 A NO813850 A NO 813850A NO 813850 A NO813850 A NO 813850A NO 813850 L NO813850 L NO 813850L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- mixture
- carbon atoms
- substituent
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 38
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 9
- 230000001225 therapeutic effect Effects 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 134
- 150000001875 compounds Chemical class 0.000 claims description 81
- 239000007858 starting material Substances 0.000 claims description 28
- -1 cyano, nitro, amino Chemical group 0.000 claims description 23
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000011593 sulfur Chemical group 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- HSXKYYUIHDFNRA-UHFFFAOYSA-N n,n-dimethyl-4-(5-oxo-4h-1,3,4-thiadiazin-2-yl)benzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C1=NNC(=O)CS1 HSXKYYUIHDFNRA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 89
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 47
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 238000010992 reflux Methods 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 239000012265 solid product Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000002425 crystallisation Methods 0.000 description 16
- 230000008025 crystallization Effects 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000003776 cleavage reaction Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000012258 stirred mixture Substances 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- HVTOBWOJYATYSS-UHFFFAOYSA-N 4-(3-oxo-4,5-dihydro-2h-1,2,4-triazin-6-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NNC(=O)NC1 HVTOBWOJYATYSS-UHFFFAOYSA-N 0.000 description 6
- FAZCRRBZLANAHU-UHFFFAOYSA-N 4-(5-oxo-4h-1,3,4-thiadiazin-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NNC(=O)CS1 FAZCRRBZLANAHU-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- CHPODLGGUNEVME-UHFFFAOYSA-N 3-(3-oxo-4,5-dihydro-2h-1,2,4-triazin-6-yl)benzonitrile Chemical compound N1C(=O)NCC(C=2C=C(C=CC=2)C#N)=N1 CHPODLGGUNEVME-UHFFFAOYSA-N 0.000 description 5
- HTAWAXPFBGGDAO-UHFFFAOYSA-N 3-(4-aminophenyl)-2,5-dihydro-1h-1,2,4-triazin-6-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)CN1 HTAWAXPFBGGDAO-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 4
- PSMVDHLNNKJVIA-UHFFFAOYSA-N 3-(4-nitrophenyl)-2,5-dihydro-1h-1,2,4-triazin-6-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NNC(=O)CN1 PSMVDHLNNKJVIA-UHFFFAOYSA-N 0.000 description 4
- YYSFJIYEWMZIJQ-UHFFFAOYSA-N 5-phenyltriazine-4-carbonitrile Chemical compound N#CC1=NN=NC=C1C1=CC=CC=C1 YYSFJIYEWMZIJQ-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000005077 diacylhydrazine group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- GULMALYPRWHMKP-UHFFFAOYSA-N 2-(4-aminophenyl)-4h-1,3,4-oxadiazin-5-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)CO1 GULMALYPRWHMKP-UHFFFAOYSA-N 0.000 description 3
- BRJHPXYHGOUIIQ-UHFFFAOYSA-N 5-(4-aminophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)SC1 BRJHPXYHGOUIIQ-UHFFFAOYSA-N 0.000 description 3
- KRCFPAIYHKMITR-UHFFFAOYSA-N 6-(4-aminophenyl)-4,5-dihydro-2h-1,2,4-triazin-3-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)NC1 KRCFPAIYHKMITR-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000003177 cardiotonic effect Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- TVZQVIKUAYXCAB-UHFFFAOYSA-N n-[4-(aminocarbamothioyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(=S)NN)C=C1 TVZQVIKUAYXCAB-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DHPLSIGRWHSWSR-UHFFFAOYSA-N 2-(4-aminophenyl)-4h-1,3,4-thiadiazin-5-one Chemical compound C1=CC(N)=CC=C1C1=NNC(=O)CS1 DHPLSIGRWHSWSR-UHFFFAOYSA-N 0.000 description 2
- XWCGNFLHRINYCE-UHFFFAOYSA-N 3-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=CC(C#N)=C1 XWCGNFLHRINYCE-UHFFFAOYSA-N 0.000 description 2
- WOEJMLQUCYKCIQ-UHFFFAOYSA-N 4-(3-oxo-4,5-dihydro-2h-1,2,4-triazin-6-yl)benzonitrile Chemical compound N1C(=O)NCC(C=2C=CC(=CC=2)C#N)=N1 WOEJMLQUCYKCIQ-UHFFFAOYSA-N 0.000 description 2
- DWOSVTZIVHZZOM-UHFFFAOYSA-N 4-(5-oxo-4h-1,3,4-oxadiazin-2-yl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=NNC(=O)CO1 DWOSVTZIVHZZOM-UHFFFAOYSA-N 0.000 description 2
- ADCKYQAANIWGAW-UHFFFAOYSA-N 4-(6-oxo-2,5-dihydro-1h-1,2,4-triazin-3-yl)benzonitrile Chemical compound N1C(=O)CNC(C=2C=CC(=CC=2)C#N)=N1 ADCKYQAANIWGAW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- BRFUJSROKAAPJT-UHFFFAOYSA-N [2-(3-nitrophenyl)-2-oxoethyl]azanium;chloride Chemical compound Cl.NCC(=O)C1=CC=CC([N+]([O-])=O)=C1 BRFUJSROKAAPJT-UHFFFAOYSA-N 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 150000003939 benzylamines Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000496 cardiotonic agent Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- FZIFHLRZVOQASN-UHFFFAOYSA-N ethyl 2-(4-cyanophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(C#N)C=C1 FZIFHLRZVOQASN-UHFFFAOYSA-N 0.000 description 2
- FGQTXDKZTAZFRS-UHFFFAOYSA-N ethyl 2-[(4-nitrobenzoyl)amino]acetate Chemical compound CCOC(=O)CNC(=O)C1=CC=C([N+]([O-])=O)C=C1 FGQTXDKZTAZFRS-UHFFFAOYSA-N 0.000 description 2
- ARHNOQXUZYSHGE-UHFFFAOYSA-N ethyl 2-[4-(6-oxo-2,5-dihydro-1h-1,2,4-triazin-3-yl)phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1C1=NNC(=O)CN1 ARHNOQXUZYSHGE-UHFFFAOYSA-N 0.000 description 2
- ZKXMKMLGUYSGNS-UHFFFAOYSA-N ethyl 3-cyanobenzoate Chemical compound CCOC(=O)C1=CC=CC(C#N)=C1 ZKXMKMLGUYSGNS-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- USMDNNUGLLQDCX-UHFFFAOYSA-N ethyl n-[2-(3-nitrophenyl)-2-oxoethyl]carbamate Chemical compound CCOC(=O)NCC(=O)C1=CC=CC([N+]([O-])=O)=C1 USMDNNUGLLQDCX-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- WVQURDZDTBLLNU-UHFFFAOYSA-N methyl n-[2-(3-cyanophenyl)-2-oxoethyl]carbamate Chemical compound COC(=O)NCC(=O)C1=CC=CC(C#N)=C1 WVQURDZDTBLLNU-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- MGLVJJXNTFMMRJ-UHFFFAOYSA-N propan-2-yl 4-(2-oxo-3,6-dihydro-1,3,4-thiadiazin-5-yl)benzoate Chemical compound C1=CC(C(=O)OC(C)C)=CC=C1C1=NNC(=O)SC1 MGLVJJXNTFMMRJ-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
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- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 229960002474 hydralazine Drugs 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical group C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000006207 intravenous dosage form Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
- 229960000201 isosorbide dinitrate Drugs 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000000936 membranestabilizing effect Effects 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- IEXZTNVDSNCHCK-UHFFFAOYSA-N methyl n-[2-(3-cyanophenyl)-2-hydrazinylethyl]carbamate Chemical compound COC(=O)NCC(NN)C1=CC=CC(C#N)=C1 IEXZTNVDSNCHCK-UHFFFAOYSA-N 0.000 description 1
- SOUOZKQQKQESGN-UHFFFAOYSA-N methyl n-[2-(4-cyanophenyl)-2-oxoethyl]carbamate Chemical compound COC(=O)NCC(=O)C1=CC=C(C#N)C=C1 SOUOZKQQKQESGN-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- JHUPHJIECOGBHR-UHFFFAOYSA-N n,n-dimethyl-2-[4-(6-oxo-2,5-dihydro-1h-1,2,4-triazin-3-yl)phenoxy]acetamide Chemical compound C1=CC(OCC(=O)N(C)C)=CC=C1C1=NCC(=O)NN1 JHUPHJIECOGBHR-UHFFFAOYSA-N 0.000 description 1
- WECHHDJTILFYQT-UHFFFAOYSA-N n-(4-acetylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C(C)=O)C=C1 WECHHDJTILFYQT-UHFFFAOYSA-N 0.000 description 1
- JGCDYYAXNUYBHB-UHFFFAOYSA-N n-(4-propanoylphenyl)acetamide Chemical compound CCC(=O)C1=CC=C(NC(C)=O)C=C1 JGCDYYAXNUYBHB-UHFFFAOYSA-N 0.000 description 1
- GFIJUTLQAPBIIT-UHFFFAOYSA-N n-[4-(2-aminoacetyl)phenyl]acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=C(C(=O)CN)C=C1 GFIJUTLQAPBIIT-UHFFFAOYSA-N 0.000 description 1
- SDKVXRPXRNDYPD-UHFFFAOYSA-N n-[4-(2-azidoacetyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(=O)CN=[N+]=[N-])C=C1 SDKVXRPXRNDYPD-UHFFFAOYSA-N 0.000 description 1
- BDOHURFEYYDIQE-UHFFFAOYSA-N n-[4-(2-bromoacetyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(C(=O)CBr)C=C1 BDOHURFEYYDIQE-UHFFFAOYSA-N 0.000 description 1
- LLZKTKZPJBSEHD-UHFFFAOYSA-N n-[4-(2-bromopropanoyl)phenyl]acetamide Chemical compound CC(Br)C(=O)C1=CC=C(NC(C)=O)C=C1 LLZKTKZPJBSEHD-UHFFFAOYSA-N 0.000 description 1
- YAOIEFFVOYAMEK-UHFFFAOYSA-N n-[4-(2-oxo-3,6-dihydro-1,3,4-thiadiazin-5-yl)phenyl]-2-phenylacetamide Chemical compound C=1C=C(C=2CSC(=O)NN=2)C=CC=1NC(=O)CC1=CC=CC=C1 YAOIEFFVOYAMEK-UHFFFAOYSA-N 0.000 description 1
- XMVDPRRTZRQRED-UHFFFAOYSA-N n-[4-(3-oxo-4,5-dihydro-2h-1,2,4-triazin-6-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC(=O)NC1 XMVDPRRTZRQRED-UHFFFAOYSA-N 0.000 description 1
- ASHPDAJZNUZDQH-UHFFFAOYSA-N n-[4-(5-oxo-4h-1,3,4-thiadiazin-2-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC(=O)CS1 ASHPDAJZNUZDQH-UHFFFAOYSA-N 0.000 description 1
- NIJZKFLFTMYAPB-UHFFFAOYSA-N n-[4-(6-oxo-2,5-dihydro-1h-1,2,4-triazin-3-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC(=O)CN1 NIJZKFLFTMYAPB-UHFFFAOYSA-N 0.000 description 1
- MSVQGCLAPXOABZ-UHFFFAOYSA-N n-[4-(piperidine-1-carbothioyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=S)N1CCCCC1 MSVQGCLAPXOABZ-UHFFFAOYSA-N 0.000 description 1
- YHCMUZFTMLIKIG-UHFFFAOYSA-N n-benzyl-2-[4-(6-oxo-2,5-dihydro-1h-1,2,4-triazin-3-yl)phenoxy]acetamide Chemical compound C=1C=CC=CC=1CNC(=O)COC(C=C1)=CC=C1C1=NNC(=O)CN1 YHCMUZFTMLIKIG-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- SEBZVOQSPRJJDS-UHFFFAOYSA-N n-methyl-2-[3-(5-oxo-4h-1,3,4-thiadiazin-2-yl)phenoxy]acetamide Chemical compound CNC(=O)COC1=CC=CC(C=2SCC(=O)NN=2)=C1 SEBZVOQSPRJJDS-UHFFFAOYSA-N 0.000 description 1
- UIJMYDQSIGQFLF-UHFFFAOYSA-N n-methyl-2-[4-(5-oxo-4h-1,3,4-thiadiazin-2-yl)phenoxy]acetamide Chemical compound C1=CC(OCC(=O)NC)=CC=C1C1=NNC(=O)CS1 UIJMYDQSIGQFLF-UHFFFAOYSA-N 0.000 description 1
- VEOUIQRJXKFCHM-UHFFFAOYSA-N n-methyl-3-(5-oxo-4h-1,3,4-oxadiazin-2-yl)benzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(C=2OCC(=O)NN=2)=C1 VEOUIQRJXKFCHM-UHFFFAOYSA-N 0.000 description 1
- LTYGNZSVLXJALQ-UHFFFAOYSA-N o-ethyl n-aminocarbamothioate Chemical compound CCOC(=S)NN LTYGNZSVLXJALQ-UHFFFAOYSA-N 0.000 description 1
- LNWHCOPMPXKPNZ-UHFFFAOYSA-N o-methyl n-aminocarbamothioate Chemical compound COC(=S)NN LNWHCOPMPXKPNZ-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 1
- 229960004321 pentaerithrityl tetranitrate Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- XNJRQFWFDICQNM-UHFFFAOYSA-N propan-2-yl 4-(5-oxo-4h-1,3,4-thiadiazin-2-yl)benzoate Chemical compound C1=CC(C(=O)OC(C)C)=CC=C1C1=NNC(=O)CS1 XNJRQFWFDICQNM-UHFFFAOYSA-N 0.000 description 1
- GAPZBBWNCJVJMD-UHFFFAOYSA-N propan-2-yl 4-(6-oxo-2,5-dihydro-1h-1,2,4-triazin-3-yl)benzoate Chemical compound C1=CC(C(=O)OC(C)C)=CC=C1C1=NNC(=O)CN1 GAPZBBWNCJVJMD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- PIBLZRBPXNFADW-UHFFFAOYSA-M sodium;4-(5-oxo-4h-1,3,4-thiadiazin-2-yl)benzoate Chemical compound [Na+].C1=CC(C(=O)[O-])=CC=C1C1=NNC(=O)CS1 PIBLZRBPXNFADW-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- MVJKXJPDBTXECY-UHFFFAOYSA-N trifluoroborane;hydrate Chemical compound O.FB(F)F MVJKXJPDBTXECY-UHFFFAOYSA-N 0.000 description 1
- 229960001032 trihexyphenidyl Drugs 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/194—Radicals derived from thio- or thiono carboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8036680 | 1980-11-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO813850L true NO813850L (no) | 1982-05-18 |
Family
ID=10517317
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO813850A NO813850L (no) | 1980-11-14 | 1981-11-13 | Fremgangsmaate for fremstilling av terapeutisk aktive heterocykliske forbindelser |
Country Status (20)
Country | Link |
---|---|
US (4) | US4423045A (ko) |
EP (1) | EP0052442B1 (ko) |
JP (3) | JPS57109771A (ko) |
KR (1) | KR830007624A (ko) |
AU (1) | AU7709181A (ko) |
CA (1) | CA1176250A (ko) |
DD (1) | DD202020A5 (ko) |
DE (1) | DE3172252D1 (ko) |
DK (1) | DK498881A (ko) |
ES (2) | ES507126A0 (ko) |
FI (1) | FI813566L (ko) |
GR (1) | GR79554B (ko) |
HU (1) | HU185979B (ko) |
MW (1) | MW4881A1 (ko) |
NO (1) | NO813850L (ko) |
NZ (1) | NZ198967A (ko) |
PL (2) | PL233809A1 (ko) |
PT (1) | PT73995B (ko) |
ZA (1) | ZA817597B (ko) |
ZW (1) | ZW26381A1 (ko) |
Families Citing this family (36)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4616014A (en) * | 1981-10-22 | 1986-10-07 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
ZA827641B (en) * | 1981-11-12 | 1983-09-28 | Ici Plc | Thiadiazine, oxadiazine and triazine derivatives which possess cardiotonic and/or antihypertensive activity |
US4495185A (en) * | 1981-11-12 | 1985-01-22 | Imperial Chemical Industries, Plc | 1,2,4-Triazin-3(2H) ones |
CA1199027A (en) * | 1981-11-12 | 1986-01-07 | Stuart D. Mills | Heterocyclic derivatives of pyridazinone, thiadiazinone, oxadiazinone and triazinone |
US4657906A (en) * | 1982-06-05 | 1987-04-14 | Smith Kline & French Laboratories Ltd. | Heterocyclic compounds having inotropic activity |
JPS5962578A (ja) * | 1982-10-04 | 1984-04-10 | Mitsui Toatsu Chem Inc | オキサジアジン誘導体およびそれを含有する医薬組成物 |
US4581356A (en) * | 1983-03-22 | 1986-04-08 | Fujisawa Pharmaceutical Co., Ltd. | Triazine derivatives, and pharmaceutical compositions comprising the same |
GB8310435D0 (en) * | 1983-04-18 | 1983-05-25 | Fujisawa Pharmaceutical Co | Triazine derivatives |
JPS59196874A (ja) * | 1983-04-22 | 1984-11-08 | Fujisawa Pharmaceut Co Ltd | トリアジン誘導体 |
GB8328907D0 (en) * | 1983-10-28 | 1983-11-30 | Smith Kline French Lab | Chemical compounds |
GB8329784D0 (en) * | 1983-11-08 | 1983-12-14 | Smith Kline French Lab | Heterocyclic compounds |
GB8332313D0 (en) * | 1983-12-02 | 1984-01-11 | Smith Kline French Lab | Chemical compounds |
US4508718A (en) * | 1984-01-16 | 1985-04-02 | Warner-Lambert Company | Cardiotonic and antihypertensive oxadiazinone compounds |
EP0233287B1 (en) | 1984-10-04 | 1991-01-30 | Zenyaku Kogyo Kabushikikaisha | 1,4-thiazine derivatives, process for their preparation, and cardiotonics containing the same |
JPS61106574A (ja) * | 1984-10-29 | 1986-05-24 | Yoshitomi Pharmaceut Ind Ltd | オキサ(またはチア)ジアジン誘導体 |
DE3531658A1 (de) * | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Heterocyclisch substituierte indole, zwischenprodukte, verfahren zu ihrer herstellung und arzneimittel |
FR2592878B1 (fr) * | 1986-01-16 | 1988-12-16 | Pf Medicament | Monoaryl-5 as triazinones-3 substituees en position 2, leur procede de preparation et leur application en tant que medicaments |
US4898862A (en) * | 1986-03-20 | 1990-02-06 | Sankyo Company Limited | 1,2,4-triazinone derivatives, their preparation and use |
US4861773A (en) * | 1986-04-28 | 1989-08-29 | Smith Kline & French Laboratories Limited | Heterocyclic compounds |
GB8610369D0 (en) * | 1986-04-28 | 1986-06-04 | Smith Kline French Lab | Heterocyclic compounds |
DE3706427A1 (de) * | 1987-02-27 | 1988-09-08 | Boehringer Mannheim Gmbh | Neue substituierte 3h-indole, zwischenprodukte, verfahren zu ihrer herstellung sowie arzneimittel |
AU614965B2 (en) * | 1987-06-06 | 1991-09-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Thiadiazinones |
US5185332A (en) * | 1989-02-11 | 1993-02-09 | Orion-Yhtyma Oy | Thiadiazines and pharmaceutical compositions thereof as well as method of use |
GB8903130D0 (en) * | 1989-02-11 | 1989-03-30 | Orion Yhtymae Oy | Substituted pyridazinones |
DE3913597A1 (de) * | 1989-04-25 | 1990-11-08 | Heumann Pharma Gmbh & Co | Diazinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
DE4239540A1 (de) * | 1992-11-25 | 1994-05-26 | Asta Medica Ag | Neue heterocyclische Verbindungen mit antiasthmatischer/antiallergischer, entzündungshemmender, positiv inotroper und blutdrucksenkender Wirkung |
TW309520B (ko) * | 1994-04-26 | 1997-07-01 | Mitsubishi Chem Corp | |
CN1113875C (zh) | 1994-05-04 | 2003-07-09 | 拜尔公司 | 取代的芳族硫代羧酰胺及其作为除草剂的用途 |
USRE39263E1 (en) * | 1994-05-04 | 2006-09-05 | Bayer Aktiengesellschaft | Substituted aromatic thiocarboxylic acid amides and their use as herbicides |
AU6320998A (en) | 1997-02-21 | 1998-09-09 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
DE19929781A1 (de) * | 1999-06-29 | 2001-01-04 | Bayer Ag | N-[4-(6-Oxotetrahydrotriazinyl)phenyl]amide und ihre Verwendung |
WO2007057395A2 (en) | 2005-11-16 | 2007-05-24 | Novartis Ag | Biomarkers for anti-nogo-a antibody treatment in spinal cord injury |
WO2011093401A1 (ja) * | 2010-01-27 | 2011-08-04 | 三菱レイヨン株式会社 | 新規連鎖移動剤及びそれを用いた乳化重合 |
EP3661917B1 (en) | 2017-08-04 | 2022-05-11 | Bayer Aktiengesellschaft | 6-((3-trifluoromethyl)phenyl)-4,5-dihydropyridazin-3(2h)-one derivatives as pde3a and pde3b inhibitors for treating cancer |
JOP20200024A1 (ar) | 2017-08-04 | 2020-02-02 | Bayer Ag | مركبات ثنائي هيدروكساديازينون |
WO2020157194A1 (en) | 2019-02-01 | 2020-08-06 | Bayer Aktiengesellschaft | 1,2,4-triazin-3(2h)-one compounds for the treatment of hyperproliferative diseases |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3314455A (en) * | 1964-07-24 | 1967-04-18 | Black Clawson Co | Band saw resawing machine |
US3377345A (en) * | 1966-09-23 | 1968-04-09 | Dow Chemical Co | Substituted 3, 4, 5, 6-tetrahydro-2h-1, 3, 4-oxadiazin-2-one compounds and method ofpreparation thereof |
FR8169M (ko) * | 1967-05-17 | 1970-08-31 | ||
US3946010A (en) * | 1975-04-09 | 1976-03-23 | E. R. Squibb & Sons, Inc. | 3-Phenyl-2,5-dihydro-as-triazin-6 (1H)-ones |
US4097671A (en) * | 1975-08-28 | 1978-06-27 | General Electric Company | Dihydrooxadiazinones and method for making |
US4097425A (en) * | 1975-08-28 | 1978-06-27 | General Electric Company | Thermoplastic formable blends, a foaming method and products made thereby |
US4105848A (en) * | 1976-12-27 | 1978-08-08 | General Electric Company | Process for the production of dihydrooxadiazinone compounds |
ZA827641B (en) * | 1981-11-12 | 1983-09-28 | Ici Plc | Thiadiazine, oxadiazine and triazine derivatives which possess cardiotonic and/or antihypertensive activity |
US4489074A (en) * | 1982-11-12 | 1984-12-18 | Imperial Chemical Industries, Plc | 1,3,4-Thiadiazin-2-ones |
JPH072947B2 (ja) * | 1985-06-27 | 1995-01-18 | 松下電子工業株式会社 | 螢光体 |
-
1981
- 1981-10-23 DE DE8181305020T patent/DE3172252D1/de not_active Expired
- 1981-10-23 EP EP81305020A patent/EP0052442B1/en not_active Expired
- 1981-11-02 ZW ZW263/81A patent/ZW26381A1/xx unknown
- 1981-11-03 ZA ZA817597A patent/ZA817597B/xx unknown
- 1981-11-04 AU AU77091/81A patent/AU7709181A/en not_active Abandoned
- 1981-11-04 MW MW48/81A patent/MW4881A1/xx unknown
- 1981-11-11 FI FI813566A patent/FI813566L/fi not_active Application Discontinuation
- 1981-11-11 DK DK498881A patent/DK498881A/da not_active Application Discontinuation
- 1981-11-11 GR GR66494A patent/GR79554B/el unknown
- 1981-11-11 HU HU813367A patent/HU185979B/hu unknown
- 1981-11-13 PL PL23380981A patent/PL233809A1/xx unknown
- 1981-11-13 JP JP56181250A patent/JPS57109771A/ja active Pending
- 1981-11-13 NZ NZ198967A patent/NZ198967A/en unknown
- 1981-11-13 PT PT73995A patent/PT73995B/pt unknown
- 1981-11-13 PL PL23880281A patent/PL238802A1/xx unknown
- 1981-11-13 NO NO813850A patent/NO813850L/no unknown
- 1981-11-13 ES ES507126A patent/ES507126A0/es active Granted
- 1981-11-13 CA CA000390035A patent/CA1176250A/en not_active Expired
- 1981-11-14 KR KR1019810004398A patent/KR830007624A/ko unknown
- 1981-11-16 US US06/321,899 patent/US4423045A/en not_active Expired - Lifetime
- 1981-11-16 DD DD81234877A patent/DD202020A5/de unknown
-
1982
- 1982-10-16 ES ES516588A patent/ES516588A0/es active Granted
-
1983
- 1983-08-31 US US06/528,103 patent/US4503054A/en not_active Expired - Fee Related
-
1984
- 1984-11-28 US US06/675,741 patent/US4587246A/en not_active Expired - Lifetime
-
1986
- 1986-04-24 JP JP61093477A patent/JPS6236370A/ja active Granted
- 1986-04-24 JP JP61093476A patent/JPS6230771A/ja active Pending
- 1986-05-01 US US06/858,126 patent/US4683232A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
PL233809A1 (en) | 1983-09-12 |
CA1176250A (en) | 1984-10-16 |
PT73995B (en) | 1983-06-20 |
US4503054A (en) | 1985-03-05 |
ES8307231A1 (es) | 1983-07-01 |
US4683232A (en) | 1987-07-28 |
HU185979B (en) | 1985-04-28 |
MW4881A1 (en) | 1983-09-14 |
PT73995A (en) | 1981-12-01 |
EP0052442A1 (en) | 1982-05-26 |
JPS57109771A (en) | 1982-07-08 |
JPH0572384B2 (ko) | 1993-10-12 |
FI813566L (fi) | 1982-05-15 |
NZ198967A (en) | 1984-12-14 |
PL238802A1 (en) | 1983-09-12 |
ZW26381A1 (en) | 1983-06-01 |
DD202020A5 (de) | 1983-08-24 |
ES8401044A1 (es) | 1983-11-16 |
ES507126A0 (es) | 1983-07-01 |
AU7709181A (en) | 1982-05-20 |
ES516588A0 (es) | 1983-11-16 |
US4587246A (en) | 1986-05-06 |
ZA817597B (en) | 1982-10-27 |
GR79554B (ko) | 1984-10-30 |
KR830007624A (ko) | 1983-11-04 |
DE3172252D1 (en) | 1985-10-17 |
JPS6236370A (ja) | 1987-02-17 |
US4423045A (en) | 1983-12-27 |
JPS6230771A (ja) | 1987-02-09 |
EP0052442B1 (en) | 1985-09-11 |
DK498881A (da) | 1982-05-15 |
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