CH507966A - Verfahren zur Herstellung von Benzodiazepinderivaten - Google Patents
Verfahren zur Herstellung von BenzodiazepinderivatenInfo
- Publication number
- CH507966A CH507966A CH694268A CH694268A CH507966A CH 507966 A CH507966 A CH 507966A CH 694268 A CH694268 A CH 694268A CH 694268 A CH694268 A CH 694268A CH 507966 A CH507966 A CH 507966A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- indole
- chloro
- methyl
- cyclopropylmethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 47
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 11
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 27
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 21
- RNAODKZCUVVPEN-UHFFFAOYSA-N 1h-indol-2-ylmethanamine Chemical class C1=CC=C2NC(CN)=CC2=C1 RNAODKZCUVVPEN-UHFFFAOYSA-N 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 10
- 239000011707 mineral Substances 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 6
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 150000004967 organic peroxy acids Chemical class 0.000 claims 1
- -1 cycloalkylmethyl radical Chemical class 0.000 description 244
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 78
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 55
- 239000000203 mixture Substances 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 50
- 238000002844 melting Methods 0.000 description 48
- 230000008018 melting Effects 0.000 description 48
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical class C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 32
- 238000001914 filtration Methods 0.000 description 29
- 239000002244 precipitate Substances 0.000 description 29
- 238000001953 recrystallisation Methods 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000001816 cooling Methods 0.000 description 21
- 239000013078 crystal Substances 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 238000004821 distillation Methods 0.000 description 20
- 239000010410 layer Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 150000001557 benzodiazepines Chemical class 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 229910052783 alkali metal Inorganic materials 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 238000006722 reduction reaction Methods 0.000 description 10
- CBTITARLOCZPDU-UHFFFAOYSA-N 1h-indole-2-carbonitrile Chemical class C1=CC=C2NC(C#N)=CC2=C1 CBTITARLOCZPDU-UHFFFAOYSA-N 0.000 description 9
- WVSRCIODJRBJNB-UHFFFAOYSA-N 5-chloro-1-methyl-3-phenylindole-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2N(C)C(C(N)=O)=C1C1=CC=CC=C1 WVSRCIODJRBJNB-UHFFFAOYSA-N 0.000 description 9
- WQRNPWUZAVBEBC-UHFFFAOYSA-N 5-chloro-3-phenyl-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 WQRNPWUZAVBEBC-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 9
- 235000010755 mineral Nutrition 0.000 description 9
- UPGJWSVGWWVJCU-UHFFFAOYSA-N (5-chloro-1-methyl-3-phenylindol-2-yl)methanamine Chemical compound CN1C(=C(C2=CC(=CC=C12)Cl)C1=CC=CC=C1)CN UPGJWSVGWWVJCU-UHFFFAOYSA-N 0.000 description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 8
- FSLOLRKVZPTMHC-UHFFFAOYSA-N ethyl 5-chloro-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 FSLOLRKVZPTMHC-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- GCPVYQBWPZODCB-UHFFFAOYSA-N (5-chloro-3-phenyl-1h-indol-2-yl)methanamine Chemical compound NCC=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 GCPVYQBWPZODCB-UHFFFAOYSA-N 0.000 description 7
- IMUZPCJSWNBMLL-UHFFFAOYSA-N 5-chloro-3-phenyl-1h-indole-2-carbonitrile Chemical compound C12=CC(Cl)=CC=C2NC(C#N)=C1C1=CC=CC=C1 IMUZPCJSWNBMLL-UHFFFAOYSA-N 0.000 description 7
- ASGAHGHLFFGPBN-UHFFFAOYSA-N 5-chloro-3-phenyl-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ASGAHGHLFFGPBN-UHFFFAOYSA-N 0.000 description 7
- JMWSFMSTZWHBCS-UHFFFAOYSA-N ethyl 5-chloro-1-(cyclopropylmethyl)-3-phenylindole-2-carboxylate Chemical compound C1(CC1)CN1C(=C(C2=CC(=CC=C12)Cl)C1=CC=CC=C1)C(=O)OCC JMWSFMSTZWHBCS-UHFFFAOYSA-N 0.000 description 7
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- GMHKIKWLDDUDHU-UHFFFAOYSA-N 5-chloro-1-(cyclopropylmethyl)-3-phenylindole-2-carboxylic acid Chemical compound C1(CC1)CN1C(=C(C2=CC(=CC=C12)Cl)C1=CC=CC=C1)C(=O)O GMHKIKWLDDUDHU-UHFFFAOYSA-N 0.000 description 6
- SKBHXXZKKLDGER-UHFFFAOYSA-N 5-chloro-1-methyl-3-phenylindole-2-carboxylic acid Chemical compound C12=CC(Cl)=CC=C2N(C)C(C(O)=O)=C1C1=CC=CC=C1 SKBHXXZKKLDGER-UHFFFAOYSA-N 0.000 description 6
- JKJVRWMBTYPCGL-UHFFFAOYSA-N CCC(C(C(O)=O)=NNC(C=C1)=CC=C1Cl)C1=CC=CC=C1 Chemical compound CCC(C(C(O)=O)=NNC(C=C1)=CC=C1Cl)C1=CC=CC=C1 JKJVRWMBTYPCGL-UHFFFAOYSA-N 0.000 description 6
- 150000001340 alkali metals Chemical class 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ARHAUAHAFMYQCN-UHFFFAOYSA-N (3-phenyl-1h-indol-2-yl)methanamine Chemical compound NCC=1NC2=CC=CC=C2C=1C1=CC=CC=C1 ARHAUAHAFMYQCN-UHFFFAOYSA-N 0.000 description 5
- SYNUAKGMHUUTLT-UHFFFAOYSA-N 5-chloro-1-(cyclopropylmethyl)-3-phenylindole-2-carboxamide Chemical compound NC(=O)C1=C(C2=CC(Cl)=CC=C2N1CC1CC1)C1=CC=CC=C1 SYNUAKGMHUUTLT-UHFFFAOYSA-N 0.000 description 5
- YVZLRMZSZPZZSS-UHFFFAOYSA-N 5-chloro-3-phenyl-1h-indole-2-carbonyl chloride Chemical compound ClC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 YVZLRMZSZPZZSS-UHFFFAOYSA-N 0.000 description 5
- NBUVMSJYCBLBOZ-UHFFFAOYSA-N [5-chloro-1-(cyclopropylmethyl)-3-phenylindol-2-yl]methanamine Chemical compound C1(CC1)CN1C(=C(C2=CC(=CC=C12)Cl)C1=CC=CC=C1)CN NBUVMSJYCBLBOZ-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 5
- FGSTWOPWGJKFEP-UHFFFAOYSA-N (5-bromo-3-phenyl-1H-indol-2-yl)methanamine Chemical compound NCC=1NC2=CC=C(C=C2C1C1=CC=CC=C1)Br FGSTWOPWGJKFEP-UHFFFAOYSA-N 0.000 description 4
- OPOPQCWLMKWPCJ-UHFFFAOYSA-N (5-chloro-1-methyl-3-phenylindol-2-yl)methanamine hydrochloride Chemical compound Cl.CN1C(=C(C2=CC(=CC=C12)Cl)C1=CC=CC=C1)CN OPOPQCWLMKWPCJ-UHFFFAOYSA-N 0.000 description 4
- CJQZTTVZYYROLH-UHFFFAOYSA-N (7-chloro-3-phenyl-1H-indol-2-yl)methanamine Chemical compound NCC=1NC2=C(C=CC=C2C1C1=CC=CC=C1)Cl CJQZTTVZYYROLH-UHFFFAOYSA-N 0.000 description 4
- PMEYGNLXZWUKMC-UHFFFAOYSA-N 5-chloro-1-(cyclopropylmethyl)-3-phenylindole-2-carbonitrile Chemical compound C1(CC1)CN1C(=C(C2=CC(=CC=C12)Cl)C1=CC=CC=C1)C#N PMEYGNLXZWUKMC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- KKBSHIBLPBTLFI-UHFFFAOYSA-N [1-(cyclopropylmethyl)-3-phenylindol-2-yl]methanamine Chemical compound C1(CC1)CN1C(=C(C2=CC=CC=C12)C1=CC=CC=C1)CN KKBSHIBLPBTLFI-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 150000002475 indoles Chemical class 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- 150000004031 phenylhydrazines Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- LTBPLKWCVVRBLU-UHFFFAOYSA-N (5-chloro-3-phenyl-1H-indol-2-yl)methanamine hydrochloride Chemical compound Cl.NCC=1NC2=CC=C(C=C2C1C1=CC=CC=C1)Cl LTBPLKWCVVRBLU-UHFFFAOYSA-N 0.000 description 3
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- ZKWXSURXHYGEIP-UHFFFAOYSA-N 5-chloro-1-methyl-3-phenylindole-2-carbonyl chloride Chemical compound C12=CC(Cl)=CC=C2N(C)C(C(Cl)=O)=C1C1=CC=CC=C1 ZKWXSURXHYGEIP-UHFFFAOYSA-N 0.000 description 3
- BRNGMDSSGGMXHS-UHFFFAOYSA-N 7-chloro-3-phenyl-1H-indole-2-carboxylic acid Chemical compound C1(=CC=CC=C1)C1=C(NC2=C(C=CC=C12)Cl)C(=O)O BRNGMDSSGGMXHS-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 3
- JEMPFWWWYINBES-UHFFFAOYSA-N benzyl 5-chloro-3-phenyl-1H-indole-2-carboxylate Chemical compound C1(=CC=CC=C1)C1=C(NC2=CC=C(C=C12)Cl)C(=O)OCC1=CC=CC=C1 JEMPFWWWYINBES-UHFFFAOYSA-N 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- CLRHEGMAWYPMJF-UHFFFAOYSA-N ethyl 2-oxo-3-phenylpropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=CC=C1 CLRHEGMAWYPMJF-UHFFFAOYSA-N 0.000 description 3
- 230000002140 halogenating effect Effects 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LLVSGQKDNVAAGY-UHFFFAOYSA-N methyl 5-chloro-3-phenyl-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 LLVSGQKDNVAAGY-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LNUGDYIWUZSCIX-UHFFFAOYSA-N (5-bromo-1-methyl-3-phenylindol-2-yl)methanamine Chemical compound CN1C(=C(C2=CC(=CC=C12)Br)C1=CC=CC=C1)CN LNUGDYIWUZSCIX-UHFFFAOYSA-N 0.000 description 2
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- WRPMREPGSFVNAQ-UHFFFAOYSA-N cyclopropylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CC1 WRPMREPGSFVNAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- OLNZCYBOYVBQDT-UHFFFAOYSA-N ethyl 5-chloro-1-methyl-3-phenylindole-2-carboxylate Chemical compound C12=CC(Cl)=CC=C2N(C)C(C(=O)OCC)=C1C1=CC=CC=C1 OLNZCYBOYVBQDT-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960001269 glycine hydrochloride Drugs 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 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
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- HIMNRRQRDQNAEN-UHFFFAOYSA-N n-(2-benzoylphenyl)-2-chloroacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 HIMNRRQRDQNAEN-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- A Measuring Device Byusing Mechanical Method (AREA)
Applications Claiming Priority (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6095267 | 1967-09-22 | ||
| JP6242667 | 1967-09-27 | ||
| JP6242967 | 1967-09-27 | ||
| JP6242567 | 1967-09-27 | ||
| JP6242467 | 1967-09-27 | ||
| JP6242867 | 1967-09-27 | ||
| JP6242767 | 1967-09-27 | ||
| JP6243067 | 1967-09-27 | ||
| JP6510467 | 1967-10-09 | ||
| JP6510267 | 1967-10-09 | ||
| JP6735467 | 1967-10-18 | ||
| JP7079467 | 1967-11-02 | ||
| JP7079667 | 1967-11-02 | ||
| JP7079867 | 1967-11-02 | ||
| JP7159867 | 1967-11-06 | ||
| JP7207867 | 1967-11-08 | ||
| JP7916667 | 1967-12-09 | ||
| JP8051467 | 1967-12-15 | ||
| JP8227367 | 1967-12-21 | ||
| JP150168 | 1968-01-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507966A true CH507966A (de) | 1971-05-31 |
Family
ID=27586360
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH694268A CH507966A (de) | 1967-09-22 | 1968-05-09 | Verfahren zur Herstellung von Benzodiazepinderivaten |
| CH1402168A CH537394A (de) | 1967-09-22 | 1968-09-19 | Verfahren zur Herstellung von Benzodiazepinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1402168A CH537394A (de) | 1967-09-22 | 1968-09-19 | Verfahren zur Herstellung von Benzodiazepinen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3828027A (en, 2012) |
| BE (1) | BE714914A (en, 2012) |
| CH (2) | CH507966A (en, 2012) |
| DE (1) | DE1795531A1 (en, 2012) |
| DK (2) | DK138740B (en, 2012) |
| FI (2) | FI48091C (en, 2012) |
| GB (2) | GB1210568A (en, 2012) |
| IL (1) | IL29993A (en, 2012) |
| NO (2) | NO122309B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3106400A1 (de) * | 1981-02-20 | 1982-10-21 | Fritz 7118 Ingelfingen Müller | Verfahren zur herstellung eines ventilgehaeuses |
| DE4405089A1 (de) * | 1994-02-17 | 1995-08-31 | Walter Egon Kraus | Absperrvorrichtung für Fluids, insbesondere für eine Flüssigkeit |
| DE19701213C1 (de) | 1997-01-16 | 1998-10-01 | Goldsweer Karl W | Absperrventil für Rohrleitungen |
| US6787651B2 (en) | 2000-10-10 | 2004-09-07 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compounds containing such indoles and their use as PPAR-γ binding agents |
| CN114276304B (zh) * | 2021-10-09 | 2024-07-02 | 南京苏亦欣医药科技有限公司 | 一种含有稠环的医药中间体1，5-苯并二氮杂䓬衍生物的制备方法 |
-
1968
- 1968-04-11 GB GB07646/68A patent/GB1210568A/en not_active Expired
- 1968-05-08 NO NO1782/68A patent/NO122309B/no unknown
- 1968-05-09 BE BE714914D patent/BE714914A/xx not_active IP Right Cessation
- 1968-05-09 CH CH694268A patent/CH507966A/de not_active IP Right Cessation
- 1968-05-09 DK DK219868AA patent/DK138740B/da not_active IP Right Cessation
- 1968-05-09 FI FI681308A patent/FI48091C/fi active
- 1968-05-14 IL IL29993A patent/IL29993A/xx unknown
- 1968-09-16 US US00762341A patent/US3828027A/en not_active Expired - Lifetime
- 1968-09-17 NO NO3664/68A patent/NO123759B/no unknown
- 1968-09-19 GB GB44540/68A patent/GB1253368A/en not_active Expired
- 1968-09-19 CH CH1402168A patent/CH537394A/de not_active IP Right Cessation
- 1968-09-20 DE DE19681795531 patent/DE1795531A1/de active Pending
- 1968-09-20 DK DK454768A patent/DK140893C/da active
- 1968-09-20 FI FI682673A patent/FI48837C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| IL29993A (en) | 1972-08-30 |
| DK140893C (da) | 1980-05-12 |
| FI48837C (fi) | 1975-01-10 |
| DE1795531A1 (de) | 1972-01-13 |
| GB1210568A (en) | 1970-10-28 |
| US3828027A (en) | 1974-08-06 |
| FI48837B (en, 2012) | 1974-09-30 |
| BE714914A (en, 2012) | 1968-09-30 |
| FI48091C (fi) | 1974-06-10 |
| DK140893B (da) | 1979-12-03 |
| NO122309B (en, 2012) | 1971-06-14 |
| DK138740B (da) | 1978-10-23 |
| CH537394A (de) | 1973-07-13 |
| DE1795372A1 (de) | 1972-02-03 |
| DK138740C (en, 2012) | 1979-05-21 |
| NO123759B (en, 2012) | 1972-01-10 |
| FI48091B (en, 2012) | 1974-02-28 |
| GB1253368A (en) | 1971-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |