DE2457309A1 - 2-phenylhydrazinothiazolin- beziehungsweise 2-phenylhydrazinothiazininderivate sowie ihre verwendung und verfahren zur herstellung derselben - Google Patents
2-phenylhydrazinothiazolin- beziehungsweise 2-phenylhydrazinothiazininderivate sowie ihre verwendung und verfahren zur herstellung derselbenInfo
- Publication number
- DE2457309A1 DE2457309A1 DE19742457309 DE2457309A DE2457309A1 DE 2457309 A1 DE2457309 A1 DE 2457309A1 DE 19742457309 DE19742457309 DE 19742457309 DE 2457309 A DE2457309 A DE 2457309A DE 2457309 A1 DE2457309 A1 DE 2457309A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dichlorophenyl
- hydrochloride
- phenylhydrazinothiazoline
- melting point
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 22
- KTOMRFWBRXKQDH-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-thiazol-2-yl)-2-phenylhydrazine Chemical compound S1CCN=C1NNC1=CC=CC=C1 KTOMRFWBRXKQDH-UHFFFAOYSA-N 0.000 title claims description 8
- MWCGIADNWXTPDC-UHFFFAOYSA-N C(C=C1)=CC=C1NNC1=CC=CSN1 Chemical class C(C=C1)=CC=C1NNC1=CC=CSN1 MWCGIADNWXTPDC-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 trifluoromethyl radicals Chemical class 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000000460 chlorine Substances 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 239000000047 product Substances 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 229910052717 sulfur Inorganic materials 0.000 description 25
- 239000007858 starting material Substances 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 238000001990 intravenous administration Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- NUHUWXDACLFSBT-UHFFFAOYSA-N (2,6-dichloroanilino)thiourea Chemical compound NC(=S)NNC1=C(Cl)C=CC=C1Cl NUHUWXDACLFSBT-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000000147 hypnotic effect Effects 0.000 description 8
- 206010002091 Anaesthesia Diseases 0.000 description 7
- 230000037005 anaesthesia Effects 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- IDTWYHVEGJBGPT-UHFFFAOYSA-N (2,6-dichlorophenyl)hydrazine Chemical compound NNC1=C(Cl)C=CC=C1Cl IDTWYHVEGJBGPT-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 230000003444 anaesthetic effect Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- BOXZWUJAPDRPKD-UHFFFAOYSA-N Cl.ClC1=C(C(=CC=C1)Cl)NNC=1SCCN1 Chemical compound Cl.ClC1=C(C(=CC=C1)Cl)NNC=1SCCN1 BOXZWUJAPDRPKD-UHFFFAOYSA-N 0.000 description 4
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- SFMYSMQFPJEHHK-UHFFFAOYSA-N (2,4,6-trimethylanilino)thiourea Chemical compound CC1=C(C(=CC(=C1)C)C)NNC(=S)N SFMYSMQFPJEHHK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 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 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 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
- 238000003756 stirring Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XFGPCULNJGZRTH-UHFFFAOYSA-N (2,4,6-trimethylanilino)azanium;chloride Chemical compound [Cl-].CC1=CC(C)=C(N[NH3+])C(C)=C1 XFGPCULNJGZRTH-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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010048610 Cardiotoxicity Diseases 0.000 description 2
- 235000016720 allyl isothiocyanate Nutrition 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 231100000259 cardiotoxicity Toxicity 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229960003299 ketamine Drugs 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000004081 narcotic agent Substances 0.000 description 2
- 230000003533 narcotic effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- AKMOMQJDVWEYEZ-UHFFFAOYSA-N (2,3-dimethylanilino)thiourea Chemical compound CC1=CC=CC(NNC(N)=S)=C1C AKMOMQJDVWEYEZ-UHFFFAOYSA-N 0.000 description 1
- 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
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- ATZXKYDKUIVEMG-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-2-(5-methyl-4,5-dihydro-1,3-thiazol-2-yl)hydrazine hydrochloride Chemical compound Cl.ClC1=C(C(=CC=C1)Cl)NNC=1SC(CN1)C ATZXKYDKUIVEMG-UHFFFAOYSA-N 0.000 description 1
- NDRUAYSROGJQSR-UHFFFAOYSA-N 1-(4,5-dihydro-1,3-thiazol-2-yl)-2-(2,6-dimethylphenyl)hydrazine Chemical compound CC1=CC=CC(C)=C1NNC1=NCCS1 NDRUAYSROGJQSR-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- RDULGUSYAHJBCN-UHFFFAOYSA-N 2-aminoethanol;3-aminopropan-1-ol Chemical compound NCCO.NCCCO RDULGUSYAHJBCN-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- HKBSZTBLZGVDRI-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-ylhydrazine;hydrochloride Chemical compound Cl.NNC1=NCCS1 HKBSZTBLZGVDRI-UHFFFAOYSA-N 0.000 description 1
- YCVSFCXUHPVAFH-UHFFFAOYSA-N 4-bromopyridin-3-ol Chemical compound OC1=CN=CC=C1Br YCVSFCXUHPVAFH-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- KMVPXBDOWDXXEN-UHFFFAOYSA-N 4-nitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1 KMVPXBDOWDXXEN-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- XSTGRDVMROKAQV-UHFFFAOYSA-N N(N)C=1SC(CN=1)C Chemical compound N(N)C=1SC(CN=1)C XSTGRDVMROKAQV-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- JUELISASXOMDTL-UHFFFAOYSA-N [3-(trifluoromethyl)anilino]thiourea Chemical compound NC(=S)NNC1=CC=CC(C(F)(F)F)=C1 JUELISASXOMDTL-UHFFFAOYSA-N 0.000 description 1
- WLALKDPQNNRAHI-UHFFFAOYSA-N [N-(trifluoromethyl)anilino]thiourea Chemical compound FC(F)(F)N(NC(=S)N)C1=CC=CC=C1 WLALKDPQNNRAHI-UHFFFAOYSA-N 0.000 description 1
- MCWVBHMAUQBLGX-UHFFFAOYSA-N [Na].CC1C(=O)NC(=O)NC1=O Chemical compound [Na].CC1C(=O)NC(=O)NC1=O MCWVBHMAUQBLGX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- JDXKTOBMLZLCSB-UHFFFAOYSA-N anilinothiourea Chemical compound NC(=S)NNC1=CC=CC=C1 JDXKTOBMLZLCSB-UHFFFAOYSA-N 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
- 210000000133 brain stem Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000000537 electroencephalography Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 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
- 230000026781 habituation Effects 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-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
- 239000003326 hypnotic agent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 description 1
- 230000004776 neurological deficiency Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- SQMCFUSVGSBKFK-UHFFFAOYSA-M sodium;5-(cyclohexen-1-yl)-1,5-dimethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].O=C1N(C)C(=O)[N-]C(=O)C1(C)C1=CCCCC1 SQMCFUSVGSBKFK-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 230000002618 waking effect Effects 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUGO1255A HU168777B (en, 2012) | 1973-12-04 | 1973-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2457309A1 true DE2457309A1 (de) | 1975-06-05 |
Family
ID=10996758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742457309 Withdrawn DE2457309A1 (de) | 1973-12-04 | 1974-12-04 | 2-phenylhydrazinothiazolin- beziehungsweise 2-phenylhydrazinothiazininderivate sowie ihre verwendung und verfahren zur herstellung derselben |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5350160A (en) * | 1976-10-19 | 1978-05-08 | Mitsui Toatsu Chem Inc | 2-thiazolin-2-ylhydrazine derivatives |
| EP0073393A1 (de) * | 1981-08-27 | 1983-03-09 | Bayer Ag | 2-Arylhydrazino-2-thiazoline, Acylderivate derselben, 2-Arylazo-2-thiazoline, Herstellungsverfahren und ihre Verwendung zur Bekämpfung von Ekto- und Endoparasiten |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5350160A (en) * | 1976-10-19 | 1978-05-08 | Mitsui Toatsu Chem Inc | 2-thiazolin-2-ylhydrazine derivatives |
| EP0073393A1 (de) * | 1981-08-27 | 1983-03-09 | Bayer Ag | 2-Arylhydrazino-2-thiazoline, Acylderivate derselben, 2-Arylazo-2-thiazoline, Herstellungsverfahren und ihre Verwendung zur Bekämpfung von Ekto- und Endoparasiten |
| US4575501A (en) * | 1981-08-27 | 1986-03-11 | Bayer Aktiengesellschaft | 2-Arylhydrazino-2-thiazolines, acyl derivatives of these compounds, 2-arylazo-2-thiazolines, preparation processes, and their use for combating ectoparasites and endoparasites |
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 |
| FI57942C (fi) | 1980-11-10 |
| PL92564B1 (en, 2012) | 1977-04-30 |
| HU168777B (en, 2012) | 1976-07-28 |
| FR2253515B1 (en, 2012) | 1978-06-30 |
| 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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Legal Events
| Date | Code | Title | Description |
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| 8141 | Disposal/no request for examination |