DE1643325B2 - 3-aminoacylaminothiophene und verfahren zu ihrer herstellung - Google Patents
3-aminoacylaminothiophene und verfahren zu ihrer herstellungInfo
- Publication number
- DE1643325B2 DE1643325B2 DE1967F0052885 DEF0052885A DE1643325B2 DE 1643325 B2 DE1643325 B2 DE 1643325B2 DE 1967F0052885 DE1967F0052885 DE 1967F0052885 DE F0052885 A DEF0052885 A DE F0052885A DE 1643325 B2 DE1643325 B2 DE 1643325B2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- hydrochloride
- general formula
- carbomethoxy
- acid
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 22
- -1 pyrrolidino, morpholino Chemical group 0.000 claims description 38
- 150000001412 amines Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 229930192474 thiophene Natural products 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical class NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 239000004744 fabric Substances 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000002253 acid Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 206010002091 Anaesthesia Diseases 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 230000037005 anaesthesia Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- OEJHVWAMVGGICN-UHFFFAOYSA-N 2-methylthiophene;hydrochloride Chemical compound Cl.CC1=CC=CS1 OEJHVWAMVGGICN-UHFFFAOYSA-N 0.000 description 6
- CEEIJOOHMCRBMH-UHFFFAOYSA-N 4-methylthiophene Chemical compound CC1=[C]SC=C1 CEEIJOOHMCRBMH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000006114 decarboxylation reaction Methods 0.000 description 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical class NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- WROUIBGUWODUPA-UHFFFAOYSA-N 2-(butylamino)-n-(2-chloro-6-methylphenyl)acetamide;hydrochloride Chemical compound [Cl-].CCCC[NH2+]CC(=O)NC1=C(C)C=CC=C1Cl WROUIBGUWODUPA-UHFFFAOYSA-N 0.000 description 4
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000008595 infiltration Effects 0.000 description 4
- 238000001764 infiltration Methods 0.000 description 4
- 238000007127 saponification reaction Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical class NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 description 3
- HFOFPDGUBCVRIQ-UHFFFAOYSA-N 4-methylthiophen-3-amine Chemical compound CC1=CSC=C1N HFOFPDGUBCVRIQ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 3
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229960001290 butanilicaine Drugs 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 229960004194 lidocaine Drugs 0.000 description 3
- 239000003589 local anesthetic agent Substances 0.000 description 3
- 229960005015 local anesthetics Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPXDKQBBJCTNOY-UHFFFAOYSA-N 1,10-phenanthrolin-10-ium;chloride Chemical compound Cl.C1=CN=C2C3=NC=CC=C3C=CC2=C1 QPXDKQBBJCTNOY-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- JCCCMAAJYSNBPR-UHFFFAOYSA-N 2-ethylthiophene Chemical compound CCC1=CC=CS1 JCCCMAAJYSNBPR-UHFFFAOYSA-N 0.000 description 2
- KYWKTFLJPYLPFB-UHFFFAOYSA-N 3-methylthiophene;hydrochloride Chemical compound Cl.CC=1C=CSC=1 KYWKTFLJPYLPFB-UHFFFAOYSA-N 0.000 description 2
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 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
- 239000005457 ice water Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical class C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
- DOPROHTZKDRGFX-UHFFFAOYSA-N 2,3-dihydrothiophen-2-amine Chemical class NC1CC=CS1 DOPROHTZKDRGFX-UHFFFAOYSA-N 0.000 description 1
- NKYZMZNNAWWQCF-UHFFFAOYSA-N 2,4-dimethylthiophen-3-amine Chemical compound CC1=CSC(C)=C1N NKYZMZNNAWWQCF-UHFFFAOYSA-N 0.000 description 1
- RRWZZMHRVSMLCT-UHFFFAOYSA-N 2-(butylazaniumyl)acetate Chemical compound CCCCNCC(O)=O RRWZZMHRVSMLCT-UHFFFAOYSA-N 0.000 description 1
- OQMYZVWIXPPDDE-UHFFFAOYSA-N 2-(cyclohexylazaniumyl)acetate Chemical compound OC(=O)CNC1CCCCC1 OQMYZVWIXPPDDE-UHFFFAOYSA-N 0.000 description 1
- WQZPOUYTFXPKFF-UHFFFAOYSA-N 2-(diethylamino)acetyl chloride Chemical compound CCN(CC)CC(Cl)=O WQZPOUYTFXPKFF-UHFFFAOYSA-N 0.000 description 1
- PRSWALMQXKFZFA-UHFFFAOYSA-N 2-(piperidin-1-ylamino)acetic acid Chemical compound OC(=O)CNN1CCCCC1 PRSWALMQXKFZFA-UHFFFAOYSA-N 0.000 description 1
- BHUGZIJOVAVBOQ-UHFFFAOYSA-N 2-(propylazaniumyl)acetate Chemical group CCCNCC(O)=O BHUGZIJOVAVBOQ-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-M 2-Methyl-2-butenoic acid Natural products C\C=C(\C)C([O-])=O UIERETOOQGIECD-ARJAWSKDSA-M 0.000 description 1
- RTZFKQORWVHODG-UHFFFAOYSA-N 2-[butyl(phenylmethoxycarbonyl)amino]acetic acid Chemical compound CCCCN(CC(O)=O)C(=O)OCC1=CC=CC=C1 RTZFKQORWVHODG-UHFFFAOYSA-N 0.000 description 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical class CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
- FIMCOWPZXBVBIB-UHFFFAOYSA-N 2-chloro-N-(4-methylthiophen-3-yl)acetamide Chemical compound ClCC(=O)NC1=CSC=C1C FIMCOWPZXBVBIB-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-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
- DMGYMQMLXUHTDQ-UHFFFAOYSA-N 3-methyl-2,3-dihydrothiophene Chemical compound CC1CSC=C1 DMGYMQMLXUHTDQ-UHFFFAOYSA-N 0.000 description 1
- DLABLFPCTXRQMY-UHFFFAOYSA-N 3-methylthiolane Chemical compound CC1CCSC1 DLABLFPCTXRQMY-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
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- CNDKEPQJHLNOTH-UHFFFAOYSA-N C(CCC)NC1=C(SC=C1)NC(C)=O Chemical compound C(CCC)NC1=C(SC=C1)NC(C)=O CNDKEPQJHLNOTH-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- POHGVLJVCVHDRH-UHFFFAOYSA-N N-[3-(butylamino)-4-methylthiophen-2-yl]acetamide Chemical compound C(CCC)NC1=C(SC=C1C)NC(C)=O POHGVLJVCVHDRH-UHFFFAOYSA-N 0.000 description 1
- VFNUTUQTELVMGI-UHFFFAOYSA-N N-[3-(diethylamino)-4-methylthiophen-2-yl]acetamide Chemical compound C(C)N(C1=C(SC=C1C)NC(C)=O)CC VFNUTUQTELVMGI-UHFFFAOYSA-N 0.000 description 1
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 1
- YPIGGYHFMKJNKV-UHFFFAOYSA-N N-ethylglycine Chemical group CC[NH2+]CC([O-])=O YPIGGYHFMKJNKV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical group 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- KQDJZZWCYTXUDE-UHFFFAOYSA-N hydron;thiophene;chloride Chemical compound Cl.C=1C=CSC=1 KQDJZZWCYTXUDE-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YICRPERKKBDRSP-UHFFFAOYSA-N methyl 3-amino-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1N YICRPERKKBDRSP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 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
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
-
- 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (45)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0052885 DE1643325B2 (de) | 1967-07-07 | 1967-07-07 | 3-aminoacylaminothiophene und verfahren zu ihrer herstellung |
| YU155668A YU33871B (en) | 1967-07-07 | 1968-07-02 | Process for preparing novel, substituted 3-aminoacyl-amino-thiophenes |
| CH1196570A CH498851A (de) | 1967-07-07 | 1968-07-04 | Verfahren zur Herstellung von neuen 3-Aminoacylamino-thiophenen |
| CH1196770A CH505128A (de) | 1967-07-07 | 1968-07-04 | Verfahren zur Herstellung von neuen 3-Aminoacylaminothiophenen |
| CH1196870A CH498852A (de) | 1967-07-07 | 1968-07-04 | Verfahren zur Herstellung von neuen 3-Aminoacylamino-thiophenen |
| CH1196670A CH507971A (de) | 1967-07-07 | 1968-07-04 | Verfahren zur Herstellung von neuen 3-Aminoacylaminothiophenen |
| CH1196470A CH498850A (de) | 1967-07-07 | 1968-07-04 | Verfahren zur Herstellung von neuen 3-Aminoacylamino-thiophenen |
| CH1196970A CH506546A (de) | 1967-07-07 | 1968-07-04 | Verfahren zur Herstellung von neuen 3-Aminoacylaminothiophenen |
| CH1001468A CH504451A (de) | 1967-07-07 | 1968-07-04 | Verfahren zur Herstellung von neuen 3-Aminoacylaminothiophenen |
| AT615769A AT282612B (de) | 1967-07-07 | 1968-07-05 | Verfahren zur Herstellung von neuen substituierten 3-Aminoacylamino-thiophenen und ihren Salzen |
| CS498368A CS150583B2 (cs) | 1967-07-07 | 1968-07-05 | |
| AT06161/69A AT282615B (de) | 1967-07-07 | 1968-07-05 | Verfahren zur herstellung von neuen substituierten 3-aminoacylamino-thiphenen und ihren salzen |
| AT615669A AT281810B (de) | 1967-07-07 | 1968-07-05 | Verfahren zur Herstellung von neuen substituierten 3-Aminoacylamino-thiophenen und ihren Salzen |
| CS527968A CS150588B2 (cs) | 1967-07-07 | 1968-07-05 | |
| CS527768A CS150586B2 (cs) | 1967-07-07 | 1968-07-05 | |
| AT615869A AT282613B (de) | 1967-07-07 | 1968-07-05 | Verfahren zur Herstellung von neuen substituierten 3-Aminoacylamino-thiophenen und ihren Salzen |
| AT616069A AT284833B (de) | 1967-07-07 | 1968-07-05 | Verfahren zur Herstellung von neuen substituierten 3-Aminoacylamino-thiophenen und ihren Salzen |
| FI194668A FI50879C (fi) | 1967-07-07 | 1968-07-05 | Menetelmä terapeuttisesti vaikuttavien substituoitujen 3-aminoasyyliam ino-tiofeenien valmistamiseksi. |
| AT648968A AT281809B (de) | 1967-07-07 | 1968-07-05 | Verfahren zur Herstellung von neuen substituierten 3-Aminoacacylamino-thiophenen und ihren Salzen |
| CS527568A CS150584B2 (cs) | 1967-07-07 | 1968-07-05 | |
| CS527868A CS150587B2 (cs) | 1967-07-07 | 1968-07-05 | |
| AT615969A AT282614B (de) | 1967-07-07 | 1968-07-05 | Verfahren zur Herstellung von neuen substituierten 3-Aminoacylaminothiophenen und ihren Salzen |
| DK330768A DK120029B (da) | 1967-07-07 | 1968-07-05 | Analogifremgangsmåde til fremstilling af substituerede 3-aminoacylaminothiophener eller salte deraf. |
| CS528071A CS150589B2 (cs) | 1967-07-07 | 1968-07-05 | |
| CS527668A CS150585B2 (cs) | 1967-07-07 | 1968-07-05 | |
| NL6809539A NL156405B (nl) | 1967-07-07 | 1968-07-05 | Werkwijze voor het bereiden van een geneesmiddel met lokaal-anesthetische werking, aldus verkregen gevormde geneesmiddelen, alsmede werkwijze voor het bereiden van daarvoor geschikte actieve verbindingen. |
| ES355858A ES355858A1 (es) | 1967-07-07 | 1968-07-06 | Procedimiento para la preparacion de 3 - amino acilamino- tiofenos sustituidos. |
| GB3243868A GB1234833A (en) | 1967-07-07 | 1968-07-08 | 3-aminoacylamino-thiophens and process for preparing them |
| FR1584764D FR1584764A (cs) | 1967-07-07 | 1968-07-08 | |
| SE937268A SE352639B (cs) | 1967-07-07 | 1968-07-08 | |
| BE717788D BE717788A (cs) | 1967-07-07 | 1968-07-08 | |
| NO271568A NO122432B (cs) | 1967-07-07 | 1968-07-08 | |
| FR168764A FR8214M (cs) | 1967-07-07 | 1968-10-04 | |
| YU256373A YU34043B (en) | 1967-07-07 | 1973-09-27 | Process for preparing novel 3-amino-acylamino-thiophens |
| YU256173A YU33962B (en) | 1967-07-07 | 1973-09-27 | Process for preparing novel 3-amino-acylamino thiophenes |
| YU256073A YU33961B (en) | 1967-07-07 | 1973-09-27 | Process for preparing novel 3-amino-acylamino thiophenes |
| YU256473A YU33964B (en) | 1967-07-07 | 1973-09-27 | Process for preparing novel 3-amino-acylamino thiophenes |
| YU256273A YU33963B (en) | 1967-07-07 | 1973-09-27 | Process for preparing novel 3-amino-acylamino thiophenes |
| YU256573A YU33965B (en) | 1967-07-07 | 1973-09-27 | Process for preparing novel 3-amino-acylamino thiophenes |
| IN1730/CAL/75A IN141963B (cs) | 1967-07-07 | 1975-09-10 | |
| IN1728/CAL/1975A IN141961B (cs) | 1967-07-07 | 1975-09-10 | |
| IN1733/CAL/1975A IN141966B (cs) | 1967-07-07 | 1975-09-10 | |
| IN1732/CAL/1975A IN141965B (cs) | 1967-07-07 | 1975-09-10 | |
| IN1731/CAL/75A IN141964B (cs) | 1967-07-07 | 1975-09-10 | |
| IN1729/CAL/75A IN141962B (cs) | 1967-07-07 | 1975-09-10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0052885 DE1643325B2 (de) | 1967-07-07 | 1967-07-07 | 3-aminoacylaminothiophene und verfahren zu ihrer herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1643325A1 DE1643325A1 (de) | 1971-03-25 |
| DE1643325B2 true DE1643325B2 (de) | 1976-05-06 |
Family
ID=7105818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967F0052885 Granted DE1643325B2 (de) | 1967-07-07 | 1967-07-07 | 3-aminoacylaminothiophene und verfahren zu ihrer herstellung |
Country Status (14)
| Country | Link |
|---|---|
| AT (7) | AT284833B (cs) |
| BE (1) | BE717788A (cs) |
| CH (1) | CH504451A (cs) |
| CS (7) | CS150588B2 (cs) |
| DE (1) | DE1643325B2 (cs) |
| DK (1) | DK120029B (cs) |
| ES (1) | ES355858A1 (cs) |
| FI (1) | FI50879C (cs) |
| FR (2) | FR1584764A (cs) |
| GB (1) | GB1234833A (cs) |
| NL (1) | NL156405B (cs) |
| NO (1) | NO122432B (cs) |
| SE (1) | SE352639B (cs) |
| YU (7) | YU33871B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166346A (en) * | 1987-12-11 | 1992-11-24 | Hoechst Aktiengesellschaft | Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxides |
| CA62573S (en) | 1989-02-20 | 1989-02-28 | Raymond Rodenburgh | Double unit for retaining wall |
| DE4244069A1 (de) * | 1992-12-24 | 1994-06-30 | Hoechst Ag | Cephalosporinsalze und Verfahren zu deren Herstellung |
-
1967
- 1967-07-07 DE DE1967F0052885 patent/DE1643325B2/de active Granted
-
1968
- 1968-07-02 YU YU155668A patent/YU33871B/xx unknown
- 1968-07-04 CH CH1001468A patent/CH504451A/de not_active IP Right Cessation
- 1968-07-05 CS CS527968A patent/CS150588B2/cs unknown
- 1968-07-05 AT AT616069A patent/AT284833B/de not_active IP Right Cessation
- 1968-07-05 AT AT615869A patent/AT282613B/de not_active IP Right Cessation
- 1968-07-05 AT AT615969A patent/AT282614B/de not_active IP Right Cessation
- 1968-07-05 NL NL6809539A patent/NL156405B/xx not_active IP Right Cessation
- 1968-07-05 FI FI194668A patent/FI50879C/fi active
- 1968-07-05 CS CS498368A patent/CS150583B2/cs unknown
- 1968-07-05 CS CS527568A patent/CS150584B2/cs unknown
- 1968-07-05 CS CS527868A patent/CS150587B2/cs unknown
- 1968-07-05 CS CS528071A patent/CS150589B2/cs unknown
- 1968-07-05 CS CS527668A patent/CS150585B2/cs unknown
- 1968-07-05 AT AT615769A patent/AT282612B/de not_active IP Right Cessation
- 1968-07-05 AT AT06161/69A patent/AT282615B/de not_active IP Right Cessation
- 1968-07-05 AT AT648968A patent/AT281809B/de not_active IP Right Cessation
- 1968-07-05 DK DK330768A patent/DK120029B/da not_active IP Right Cessation
- 1968-07-05 AT AT615669A patent/AT281810B/de not_active IP Right Cessation
- 1968-07-05 CS CS527768A patent/CS150586B2/cs unknown
- 1968-07-06 ES ES355858A patent/ES355858A1/es not_active Expired
- 1968-07-08 BE BE717788D patent/BE717788A/xx not_active IP Right Cessation
- 1968-07-08 FR FR1584764D patent/FR1584764A/fr not_active Expired
- 1968-07-08 SE SE937268A patent/SE352639B/xx unknown
- 1968-07-08 GB GB3243868A patent/GB1234833A/en not_active Expired
- 1968-07-08 NO NO271568A patent/NO122432B/no unknown
- 1968-10-04 FR FR168764A patent/FR8214M/fr not_active Expired
-
1973
- 1973-09-27 YU YU256173A patent/YU33962B/xx unknown
- 1973-09-27 YU YU256373A patent/YU34043B/xx unknown
- 1973-09-27 YU YU256473A patent/YU33964B/xx unknown
- 1973-09-27 YU YU256573A patent/YU33965B/xx unknown
- 1973-09-27 YU YU256273A patent/YU33963B/xx unknown
- 1973-09-27 YU YU256073A patent/YU33961B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2537070C2 (cs) | ||
| DE2426149B2 (de) | 7-Fluor-substituierte Phenothiazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| AT200578B (de) | Verfahren zur Herstellung von neuen N-Aminoalkylderivaten von Azepinen | |
| DE2514673C2 (de) | Benzo[b]bicyclo[3.3.1]nona-3,6a(10a)diene, Verfahren zu ihrer Herstellung und diese enthaltende anorektische Mittel | |
| DE1643325B2 (de) | 3-aminoacylaminothiophene und verfahren zu ihrer herstellung | |
| EP0389425B1 (de) | Neue Benzothiopyranylamine | |
| DE1643325C3 (de) | 3-Aminoacylaminothiophene und Verfahren zu ihrer Herstellung | |
| DE3300522C2 (cs) | ||
| CH630902A5 (en) | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. | |
| DE2653251A1 (de) | Azabicyclo eckige klammer auf 3.1.o eckige klammer zu hexan-derivate, ihre herstellung und verwendung | |
| DE1035150B (de) | Verfahren zur Herstellung von N-monosubstituierten ª‡-(tert.-Aminoalkyl)-ª‡-phenyl-acetamiden | |
| DE1038047B (de) | Verfahren zur Herstellung von N-aminoalkylierten Iminodibenzylen und deren Salzen | |
| DE2202486A1 (de) | Verfahren zur Herstellung von Ketonen des 10,11-Dihydro-dibenzo [b,f] azepins | |
| DE2745280A1 (de) | Tricyclische verbindungen | |
| CH473821A (de) | Verfahren zur Herstellung von Iminodibenzyl-Derivaten | |
| AT273985B (de) | Verfahren zur Herstellung von neuen azabicycloaliphatischen Verbindungen und ihren Salzen | |
| AT320147B (de) | Verfahren zur Herstellung von neuen Penicillinen und Cephalosporinen | |
| AT243268B (de) | Verfahren zur Herstellung von neuen Benzochinolizin-Derivaten | |
| DE1235922B (de) | Verfahren zur Herstellung von neuen N-substituierten 4-Phenyl-piperidin-4-carbon-saeureaethylesterabkoemmlingen | |
| AT235836B (de) | Verfahren zur Herstellung von neuen basisch substituierten Polymethylentetrahydrochinolinen | |
| AT324342B (de) | Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen und ihren salzen | |
| DE1670105A1 (de) | Verfahren zur Herstellung von Benzofuryl (3)-alkylaminen und deren Salzen | |
| AT358042B (de) | Verfahren zur herstellung neuer 1-amino-2- -hydroxy-3-heterocyclyloxy-propane und ihrer salze | |
| DE1670011C3 (de) | Am Kohlenstoff des Heterocyclus alkylierte NJV'-disubstituierte Diazacycloalkane und diese enthaltende Arzneimittel | |
| AT367404B (de) | Verfahren zur herstellung von neuen 1,2,3,4,4a, 10b-hexahydro-benz(f)isochinolinderivaten und ihren saeureadditionssalzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |