CH599202A5 - Thiophene derivs - Google Patents

Thiophene derivs

Info

Publication number: CH599202A5
Authority: CH; Switzerland
Prior art keywords: sep; oxalate; ethyl; thienyl; methyl
Prior art date: 1972-09-13

Application number

CH1138273A

Other languages

English (en)

French (fr)

Inventor

Tetsuya Tahara

Hideo Matsuki

Kazuhiko Araki

Masami Shiroki

Original Assignee

Yoshitomi Pharmaceutical

Priority date (The priority date 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 date listed.)

1972-09-13

Filing date

1973-08-02

Publication date

1978-05-12

1972-09-13 Priority claimed from JP9253472A external-priority patent/JPS5516431B2/ja

1972-09-16 Priority claimed from JP9333772A external-priority patent/JPS5521750B2/ja

1973-08-02 Application filed by Yoshitomi Pharmaceutical filed Critical Yoshitomi Pharmaceutical

1978-05-12 Publication of CH599202A5 publication Critical patent/CH599202A5/fr

Links

YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title abstract 4
229930192474 thiophene Natural products 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims description 17
-1 piperidino, 4-methyl-1-piperazinyl Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003577 thiophenes Chemical class 0.000 claims description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
206010021143 Hypoxia Diseases 0.000 abstract description 4
206010002660 Anoxia Diseases 0.000 abstract description 2
241000976983 Anoxia Species 0.000 abstract description 2
230000007953 anoxia Effects 0.000 abstract description 2
229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
239000001961 anticonvulsive agent Substances 0.000 abstract description 2
239000002249 anxiolytic agent Substances 0.000 abstract description 2
230000000949 anxiolytic effect Effects 0.000 abstract description 2
229940005530 anxiolytics Drugs 0.000 abstract description 2
230000007954 hypoxia Effects 0.000 abstract description 2
229940125723 sedative agent Drugs 0.000 abstract description 2
239000000932 sedative agent Substances 0.000 abstract description 2
230000001012 protector Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
239000002904 solvent Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000003921 oil Substances 0.000 description 8
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
125000006519 CCH3 Chemical group 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
IMUMZOOEMVOHBF-UHFFFAOYSA-N [2-[2-(chloromethyl)imidazol-1-yl]-5-ethylthiophen-3-yl]-(2-chlorophenyl)methanone Chemical compound C1=CN=C(CCl)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1Cl IMUMZOOEMVOHBF-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
235000011181 potassium carbonates Nutrition 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
235000010288 sodium nitrite Nutrition 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
VWNUCFNZAFGPCK-UHFFFAOYSA-N (2-chlorophenyl)-[5-ethyl-2-[3-(hydroxymethyl)-5-methyl-1,2,4-triazol-4-yl]thiophen-3-yl]methanone Chemical compound CC1=NN=C(CO)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1Cl VWNUCFNZAFGPCK-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
LCPKWCKYILFQQQ-UHFFFAOYSA-N [2-[3-(chloromethyl)-5-methyl-1,2,4-triazol-4-yl]-5-ethylthiophen-3-yl]-(2-chlorophenyl)methanone Chemical compound CC1=NN=C(CCl)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1Cl LCPKWCKYILFQQQ-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
UUZXROTVGPQZON-UHFFFAOYSA-N (2-chlorophenyl)-[5-ethyl-2-[3-methyl-5-[(4-methylpiperazin-1-yl)methyl]-1,2,4-triazol-4-yl]thiophen-3-yl]methanone;oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O.CC1=NN=C(CN2CCN(C)CC2)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1Cl UUZXROTVGPQZON-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
GPUZWNNASIXLTQ-UHFFFAOYSA-N 1h-imidazole;oxalic acid Chemical compound C1=CNC=N1.OC(=O)C(O)=O GPUZWNNASIXLTQ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
CJDTVJSOAKLFIB-UHFFFAOYSA-N [2-[2-(chloromethyl)imidazol-1-yl]-4,5-dimethylthiophen-3-yl]-(2-chlorophenyl)methanone Chemical compound CC1=C(C)SC(N2C(=NC=C2)CCl)=C1C(=O)C1=CC=CC=C1Cl CJDTVJSOAKLFIB-UHFFFAOYSA-N 0.000 description 1
SEBFICDPRUKHQP-UHFFFAOYSA-N [2-[2-(chloromethyl)imidazol-1-yl]-5-ethylthiophen-3-yl]-phenylmethanone Chemical compound C1=CN=C(CCl)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1 SEBFICDPRUKHQP-UHFFFAOYSA-N 0.000 description 1
WUKLOJYRXZLVRT-UHFFFAOYSA-N [2-[3-(chloromethyl)-1,2,4-triazol-4-yl]-5-ethylthiophen-3-yl]-(2-chlorophenyl)methanone Chemical compound C1=NN=C(CCl)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1Cl WUKLOJYRXZLVRT-UHFFFAOYSA-N 0.000 description 1
KKHQHXAZRSNYDG-UHFFFAOYSA-N [2-[3-(chloromethyl)-5-methyl-1,2,4-triazol-4-yl]-4,5-dimethylthiophen-3-yl]-(2-chlorophenyl)methanone Chemical compound CC1=C(C)SC(N2C(=NN=C2C)CCl)=C1C(=O)C1=CC=CC=C1Cl KKHQHXAZRSNYDG-UHFFFAOYSA-N 0.000 description 1
YVTRHRKPUSYUJR-UHFFFAOYSA-N [2-[3-(chloromethyl)-5-methyl-1,2,4-triazol-4-yl]-5-ethylthiophen-3-yl]-(2-fluorophenyl)methanone Chemical compound CC1=NN=C(CCl)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1F YVTRHRKPUSYUJR-UHFFFAOYSA-N 0.000 description 1
ZMLFCMOEJPIMBO-UHFFFAOYSA-N [2-[3-(chloromethyl)-5-methyl-1,2,4-triazol-4-yl]-5-methylthiophen-3-yl]-(2-chlorophenyl)methanone Chemical compound CC1=NN=C(CCl)N1C=1SC(C)=CC=1C(=O)C1=CC=CC=C1Cl ZMLFCMOEJPIMBO-UHFFFAOYSA-N 0.000 description 1
ZYACYDMPZRYBBH-UHFFFAOYSA-N [4-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-5-methyl-1,2,4-triazol-3-yl]methyl 4-methylbenzenesulfonate Chemical compound CC1=NN=C(COS(=O)(=O)C=2C=CC(C)=CC=2)N1C=1SC(CC)=CC=1C(=O)C1=CC=CC=C1Cl ZYACYDMPZRYBBH-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1
CRUISIDZTHMGJT-UHFFFAOYSA-L zinc;dichloride;hydrochloride Chemical compound Cl.[Cl-].[Cl-].[Zn+2] CRUISIDZTHMGJT-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1138273A 1972-09-13 1973-08-02 Thiophene derivs CH599202A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP9253472A JPS5516431B2 (de)	1972-09-13	1972-09-13
JP9333772A JPS5521750B2 (de)	1972-09-16	1972-09-16

Publications (1)

Publication Number	Publication Date
CH599202A5 true CH599202A5 (en)	1978-05-12

Family

ID=26433944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1138273A CH599202A5 (en)	1972-09-13	1973-08-02	Thiophene derivs

Country Status (2)

Country	Link
AT (1)	AT330762B (de)
CH (1)	CH599202A5 (de)

1973
- 1973-08-02 CH CH1138273A patent/CH599202A5/fr not_active IP Right Cessation
- 1973-08-08 AT AT694573A patent/AT330762B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
AT330762B (de)	1976-07-26
ATA694573A (de)	1975-10-15

Legal Events

Date	Code	Title	Description
1983-04-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH665417A5 (fr)	1988-05-13	Derives du benzimidazole, procede pour leur preparation et agents anti-ulceres contenant ces derives.
CH646969A5 (fr)	1984-12-28	Derives du beta-amino-3 nor-tropane.
CH618699A5 (de)	1980-08-15
FI93835C (fi)	1995-06-12	Menetelmä 3-(bentsotiatsol-2-yylimetyyli)-4-okso-3-H-ftaaliatsin-1-yylietikkahappojohdannaisten valmistamiseksi
US5182389A (en)	1993-01-26	Process for the preparation of 2-(2',4'-dihydroxyphenyl)-4,6-diaryl-s-triazines
EP0511074A1 (de)	1992-10-28	Heterocyclische Derivate mit Anti-Serotonin-Aktivität, ihre Herstellung und sie enthaltende Arzneimitteln
FR2472564A1 (fr)	1981-07-03	Nouveaux aryl-1 arylsulfonyl-4 1h-pyrazolols-3, et procede pour les preparer
CH616161A5 (de)	1980-03-14
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HU214822B (hu)	1998-06-29	Javított eljárás szubsztituált indolonszármazékok előállítására
EP0086678B1 (de)	1985-07-03	Verfahren zur Herstellung von 2-Acyl-1,3,4,6,7,11b-2H-hexahydro-4-pyrazino(2,1-a)isochinolinonen und Zwischenprodukte
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EP0002978A2 (de)	1979-07-11	Thiazolidindion-2,4 Derivate, deren Herstellung und Verwendung als Arzneimittel
HU208533B (en)	1993-11-29	Process for selective etherification of ascorbinic acid derivatives
CH599202A5 (en)	1978-05-12	Thiophene derivs
RU2248974C2 (ru)	2005-03-27	Способ получения {2-[4-(альфа-фенил-п-хлорбензил)пиперазин-1-ил]-этокси}-уксусной кислоты и новые промежуточные соединения
US4894457A (en)	1990-01-16	7-bromo-beta-carboline compound and method for producing same
CH616418A5 (de)	1980-03-31
US4925944A (en)	1990-05-15	Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones
FR2481280A1 (fr)	1981-10-30	Procede de preparation de derives de 2-guanidinothiazole, nouveaux produits ainsi obtenus et leur utilisation comme agents contre les ulceres d'estomac
US4172141A (en)	1979-10-23	N-(naphthylethyl)imidazole derivatives
CH616659A5 (de)	1980-04-15
FR2495157A1 (fr)	1982-06-04	Procede nouveau de preparation des tetrahydro-5, 6, 7, 7a 4h-thieno (3, 2-c) pyridinones-2
EP0454871B1 (de)	1995-04-12	Alpha, beta-ungesättigte ketone und ketoximderivat
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