FI57942C - Foerfarande foer framstaellning av nya 2-fenylhydrazinotiazoliner eller -tiaziner foer anvaendning saosom hypnotiska eller narkotiska medel - Google Patents
Foerfarande foer framstaellning av nya 2-fenylhydrazinotiazoliner eller -tiaziner foer anvaendning saosom hypnotiska eller narkotiska medel Download PDFInfo
- Publication number
- FI57942C FI57942C FI3503/74A FI350374A FI57942C FI 57942 C FI57942 C FI 57942C FI 3503/74 A FI3503/74 A FI 3503/74A FI 350374 A FI350374 A FI 350374A FI 57942 C FI57942 C FI 57942C
- Authority
- FI
- Finland
- Prior art keywords
- general formula
- methyl group
- eller
- hypnotic
- mixture
- Prior art date
Links
- 230000000147 hypnotic effect Effects 0.000 title claims description 13
- 230000003533 narcotic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- -1 2-hydroxypropyl Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 230000003444 anaesthetic effect Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003623 enhancer Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims 3
- 235000019698 starch Nutrition 0.000 claims 3
- 239000008107 starch Substances 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- 239000000047 product Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000007858 starting material Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000000155 melt Substances 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 8
- NUHUWXDACLFSBT-UHFFFAOYSA-N (2,6-dichloroanilino)thiourea Chemical compound NC(=S)NNC1=C(Cl)C=CC=C1Cl NUHUWXDACLFSBT-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IDTWYHVEGJBGPT-UHFFFAOYSA-N (2,6-dichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=CC=C1Cl IDTWYHVEGJBGPT-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000003326 hypnotic agent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 206010002091 Anaesthesia Diseases 0.000 description 4
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 4
- 230000037005 anaesthesia Effects 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 3
- PRANFOKMVYJELX-UHFFFAOYSA-N Cl.CC1CN=CS1.ClC1=C(C(=CC=C1)Cl)NN Chemical compound Cl.CC1CN=CS1.ClC1=C(C(=CC=C1)Cl)NN PRANFOKMVYJELX-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HKQHRFPIFFCFDD-UHFFFAOYSA-N S1C=NCC1.C1(=CC=CC=C1)NN Chemical class S1C=NCC1.C1(=CC=CC=C1)NN HKQHRFPIFFCFDD-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 150000004897 thiazines Chemical class 0.000 description 3
- AKMOMQJDVWEYEZ-UHFFFAOYSA-N (2,3-dimethylanilino)thiourea Chemical compound CC1=CC=CC(NNC(N)=S)=C1C AKMOMQJDVWEYEZ-UHFFFAOYSA-N 0.000 description 2
- OMOFMSZLYCEIAF-UHFFFAOYSA-N (2,5-dimethylanilino)azanium;chloride Chemical compound Cl.CC1=CC=C(C)C(NN)=C1 OMOFMSZLYCEIAF-UHFFFAOYSA-N 0.000 description 2
- IXOJKRFUDRHUCH-UHFFFAOYSA-N (2,5-dimethylanilino)thiourea Chemical compound CC1=CC=C(C)C(NNC(N)=S)=C1 IXOJKRFUDRHUCH-UHFFFAOYSA-N 0.000 description 2
- NANJFPWWJDGDMQ-UHFFFAOYSA-N (2-chloro-6-methylanilino)thiourea Chemical compound CC1=C(C(=CC=C1)Cl)NNC(=S)N NANJFPWWJDGDMQ-UHFFFAOYSA-N 0.000 description 2
- ZSOZJSVVKIOCCT-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazole (2,6-dimethylphenyl)hydrazine hydrochloride Chemical compound Cl.S1C=NCC1.CC1=C(C(=CC=C1)C)NN ZSOZJSVVKIOCCT-UHFFFAOYSA-N 0.000 description 2
- YCVSFCXUHPVAFH-UHFFFAOYSA-N 4-bromopyridin-3-ol Chemical compound OC1=CN=CC=C1Br YCVSFCXUHPVAFH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000537 electroencephalography Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- GMRQGSQUIWFFHG-UHFFFAOYSA-N methyl N-amino-N-(2,6-dichlorophenyl)carbamodithioate Chemical compound ClC1=C(C(=CC=C1)Cl)N(C(=S)SC)N GMRQGSQUIWFFHG-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ZTPAUBJZUBGGEY-UHFFFAOYSA-N (2,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C=C1Cl ZTPAUBJZUBGGEY-UHFFFAOYSA-N 0.000 description 1
- GQKQMDUOOZVZFD-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine;hydron;chloride Chemical compound [Cl-].CC1=CC=CC(C)=C1N[NH3+] GQKQMDUOOZVZFD-UHFFFAOYSA-N 0.000 description 1
- NKOMRBQXOMJFAH-UHFFFAOYSA-N (2-chloro-6-methylphenyl)hydrazine;hydrochloride Chemical compound Cl.CC1=CC=CC(Cl)=C1NN NKOMRBQXOMJFAH-UHFFFAOYSA-N 0.000 description 1
- JVAUIWWGNRYJQY-UHFFFAOYSA-N 1-(2,6-dichloroanilino)-3-(2-hydroxyethyl)thiourea Chemical compound ClC1=C(C(=CC=C1)Cl)NNC(=S)NCCO JVAUIWWGNRYJQY-UHFFFAOYSA-N 0.000 description 1
- DNHNJIKYTXSWFO-UHFFFAOYSA-N 1-(2,6-dichloroanilino)-3-(2-hydroxypropyl)thiourea Chemical compound ClC1=C(C(=CC=C1)Cl)NNC(=S)NCC(C)O DNHNJIKYTXSWFO-UHFFFAOYSA-N 0.000 description 1
- KTOMRFWBRXKQDH-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-thiazol-2-yl)-2-phenylhydrazine Chemical class S1CCN=C1NNC1=CC=CC=C1 KTOMRFWBRXKQDH-UHFFFAOYSA-N 0.000 description 1
- VXSWKOPKXDOTAQ-UHFFFAOYSA-N 1-amino-3-[3-(trifluoromethyl)anilino]thiourea Chemical compound FC(C=1C=C(C=CC1)NNC(=S)NN)(F)F VXSWKOPKXDOTAQ-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- ZUWFBQUHBOUPFK-UHFFFAOYSA-N 1-chloro-2-isothiocyanatoethane Chemical compound ClCCN=C=S ZUWFBQUHBOUPFK-UHFFFAOYSA-N 0.000 description 1
- QURBTAPQPXENJD-UHFFFAOYSA-N 2,5-dimethyl-4,5-dihydro-1,3-thiazole Chemical compound CC1CN=C(C)S1 QURBTAPQPXENJD-UHFFFAOYSA-N 0.000 description 1
- JUIQOABNSLTJSW-UHFFFAOYSA-N 2-Methyl-4,5-dihydro-1,3-thiazole Chemical compound CC1=NCCS1 JUIQOABNSLTJSW-UHFFFAOYSA-N 0.000 description 1
- WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 description 1
- DFZOBZFZZOKXSM-UHFFFAOYSA-N 2-oxo-N-phenyl-1,3-oxazolidine-3-carbothioamide Chemical compound C1(=CC=CC=C1)NC(=S)N1C(OCC1)=O DFZOBZFZZOKXSM-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- NCXJDTZWTQLSMS-UHFFFAOYSA-N C(=O)(O)C(O)C(O)C(=O)O.CC1CN=CS1.ClC1=C(C(=CC=C1)Cl)NN Chemical compound C(=O)(O)C(O)C(O)C(=O)O.CC1CN=CS1.ClC1=C(C(=CC=C1)Cl)NN NCXJDTZWTQLSMS-UHFFFAOYSA-N 0.000 description 1
- NHIJEESCWFKYFG-UHFFFAOYSA-N CC1=C(C=C(C=C1)C)N(N)S Chemical compound CC1=C(C=C(C=C1)C)N(N)S NHIJEESCWFKYFG-UHFFFAOYSA-N 0.000 description 1
- VXPJVJNRISERQX-UHFFFAOYSA-N CC1CN=CS1.ClC1=C(C(=CC=C1)Cl)NN Chemical compound CC1CN=CS1.ClC1=C(C(=CC=C1)Cl)NN VXPJVJNRISERQX-UHFFFAOYSA-N 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- MVQKXUCXPQDLMU-UHFFFAOYSA-N Cl.S1C=NCC1.CC1=C(C(=CC=C1)Cl)NN Chemical compound Cl.S1C=NCC1.CC1=C(C(=CC=C1)Cl)NN MVQKXUCXPQDLMU-UHFFFAOYSA-N 0.000 description 1
- YXBITJLHSNSBSK-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)N(N)S Chemical compound ClC1=C(C(=CC=C1)Cl)N(N)S YXBITJLHSNSBSK-UHFFFAOYSA-N 0.000 description 1
- BNQLTOYYXVHONN-UHFFFAOYSA-N ClC1=C(C(=CC=C1)Cl)N(NC(=S)N)CCO Chemical compound ClC1=C(C(=CC=C1)Cl)N(NC(=S)N)CCO BNQLTOYYXVHONN-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- RZDQPYOCMXYYKC-UHFFFAOYSA-N S1C=NCC1.ClC1=C(C(=CC=C1)Cl)NN Chemical compound S1C=NCC1.ClC1=C(C(=CC=C1)Cl)NN RZDQPYOCMXYYKC-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- LJTFFORYSFGNCT-UHFFFAOYSA-N Thiocarbohydrazide Chemical compound NNC(=S)NN LJTFFORYSFGNCT-UHFFFAOYSA-N 0.000 description 1
- RMWWXGHTAISEAK-UHFFFAOYSA-N [3-(2,2,2-trifluoroethyl)anilino]thiourea Chemical compound FC(CC=1C=C(C=CC1)NNC(=S)N)(F)F RMWWXGHTAISEAK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- QBNPBMKYUHMQTK-UHFFFAOYSA-N amino-(2,6-dichlorophenyl)carbamodithioic acid Chemical compound C1=CC(=C(C(=C1)Cl)N(C(=S)S)N)Cl QBNPBMKYUHMQTK-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XVVBLYYGZHLQDX-UHFFFAOYSA-N hydron;[3-(trifluoromethyl)phenyl]hydrazine;chloride Chemical compound Cl.NNC1=CC=CC(C(F)(F)F)=C1 XVVBLYYGZHLQDX-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000002869 intravenous anesthetic agent Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PCGUVSMZEIQKDI-UHFFFAOYSA-N n-(4,5-dihydro-1,3-thiazol-2-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=NCCS1 PCGUVSMZEIQKDI-UHFFFAOYSA-N 0.000 description 1
- GANOLKRMSPPWQJ-UHFFFAOYSA-N n-benzyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1CNC1=NCCS1 GANOLKRMSPPWQJ-UHFFFAOYSA-N 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000002981 neuropathic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- ZCRJGWZXXCALFG-UHFFFAOYSA-M potassium N-amino-N-(2,6-dichlorophenyl)carbamodithioate Chemical compound ClC1=C(C(=CC=C1)Cl)N(C(=S)[S-])N.[K+] ZCRJGWZXXCALFG-UHFFFAOYSA-M 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 231100000828 respiratory toxicity Toxicity 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO001255 | 1973-12-04 | ||
| HUGO1255A HU168777B (en, 2012) | 1973-12-04 | 1973-12-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI350374A7 FI350374A7 (en, 2012) | 1975-06-05 |
| FI57942B FI57942B (fi) | 1980-07-31 |
| FI57942C true FI57942C (fi) | 1980-11-10 |
Family
ID=10996758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3503/74A FI57942C (fi) | 1973-12-04 | 1974-12-03 | Foerfarande foer framstaellning av nya 2-fenylhydrazinotiazoliner eller -tiaziner foer anvaendning saosom hypnotiska eller narkotiska medel |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS50121268A (en, 2012) |
| AT (1) | AT340413B (en, 2012) |
| BE (1) | BE822696A (en, 2012) |
| CS (1) | CS188210B2 (en, 2012) |
| DE (1) | DE2457309A1 (en, 2012) |
| DK (1) | DK628074A (en, 2012) |
| FI (1) | FI57942C (en, 2012) |
| FR (1) | FR2253515B1 (en, 2012) |
| GB (1) | GB1469006A (en, 2012) |
| HU (1) | HU168777B (en, 2012) |
| NL (1) | NL7415739A (en, 2012) |
| PL (2) | PL92564B1 (en, 2012) |
| SE (1) | SE7415015L (en, 2012) |
| SU (1) | SU576936A3 (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5826752B2 (ja) * | 1976-10-19 | 1983-06-04 | 三井東圧化学株式会社 | ２−チアゾリン−２−イルヒドラジン誘導体 |
| DE3133918A1 (de) * | 1981-08-27 | 1983-03-17 | Bayer Ag, 5090 Leverkusen | 2-arylhydrazino-2-thiazoline, acylderivate derselben, 2-arylazo-2-thiazoline, herstellungsverfahren und ihre verwendung zur bekaempfung von ekto- und endoparasiten |
| US4550169A (en) * | 1983-11-21 | 1985-10-29 | American Cyanamid Company | Platinum chelates of 2-hydrazino-azoles |
| JPH07121923B2 (ja) * | 1988-02-04 | 1995-12-25 | 富士写真フイルム株式会社 | ２―アリールヒドラジノ―１，３―チアゾール化合物 |
| DE3933092A1 (de) * | 1989-10-04 | 1991-04-11 | Bayer Ag | Substituierte 1,3,4-thiadiazolinone verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von endoparasiten |
| GB2248314B (en) * | 1990-07-31 | 1994-03-16 | Ilford Ltd | A photographic processing tank |
| DE4121209A1 (de) * | 1991-06-27 | 1993-01-14 | Bayer Ag | 2-(3-substituierte phenylhydrazino)-2-thiazoline und 2-(3-substituierte phenylazo)-2-thiazoline, ihre herstellung und ihre verwendung zur bekaempfung von ektoparasiten |
| DE4121208A1 (de) * | 1991-06-27 | 1993-01-14 | Bayer Ag | 2-(4-substituierte phenylhydrazino)-2-thiazoline und 2-(4-substituierte phenylazo)-2-thiazoline, ihre herstellung und ihre verwendung zur bekaempfung von ektoparasiten |
-
1973
- 1973-12-04 HU HUGO1255A patent/HU168777B/hu unknown
-
1974
- 1974-11-28 BE BE150938A patent/BE822696A/xx unknown
- 1974-11-29 SE SE7415015A patent/SE7415015L/xx not_active Application Discontinuation
- 1974-12-02 CS CS748212A patent/CS188210B2/cs unknown
- 1974-12-03 FR FR7439472A patent/FR2253515B1/fr not_active Expired
- 1974-12-03 DK DK628074A patent/DK628074A/da not_active Application Discontinuation
- 1974-12-03 FI FI3503/74A patent/FI57942C/fi active
- 1974-12-03 NL NL7415739A patent/NL7415739A/xx not_active Application Discontinuation
- 1974-12-04 PL PL1974176168A patent/PL92564B1/pl unknown
- 1974-12-04 GB GB5249974A patent/GB1469006A/en not_active Expired
- 1974-12-04 DE DE19742457309 patent/DE2457309A1/de not_active Withdrawn
- 1974-12-04 JP JP49139379A patent/JPS50121268A/ja active Pending
- 1974-12-04 AT AT971774A patent/AT340413B/de not_active IP Right Cessation
- 1974-12-04 PL PL1974191334A patent/PL97347B1/pl unknown
-
1975
- 1975-12-29 SU SU7502302059A patent/SU576936A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CS188210B2 (en) | 1979-02-28 |
| ATA971774A (de) | 1977-04-15 |
| BE822696A (fr) | 1975-03-14 |
| AU7594174A (en) | 1976-06-03 |
| PL92564B1 (en, 2012) | 1977-04-30 |
| HU168777B (en, 2012) | 1976-07-28 |
| FR2253515B1 (en, 2012) | 1978-06-30 |
| DE2457309A1 (de) | 1975-06-05 |
| FI57942B (fi) | 1980-07-31 |
| SE7415015L (sv) | 1975-06-05 |
| PL97347B1 (pl) | 1978-02-28 |
| GB1469006A (en) | 1977-03-30 |
| JPS50121268A (en, 2012) | 1975-09-23 |
| AT340413B (de) | 1977-12-12 |
| DK628074A (en, 2012) | 1975-07-28 |
| FR2253515A1 (en, 2012) | 1975-07-04 |
| SU576936A3 (ru) | 1977-10-15 |
| FI350374A7 (en, 2012) | 1975-06-05 |
| NL7415739A (nl) | 1975-06-06 |
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