NO136092B - - Google Patents
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- Publication number
- NO136092B NO136092B NO3683/72A NO368372A NO136092B NO 136092 B NO136092 B NO 136092B NO 3683/72 A NO3683/72 A NO 3683/72A NO 368372 A NO368372 A NO 368372A NO 136092 B NO136092 B NO 136092B
- Authority
- NO
- Norway
- Prior art keywords
- biphenylyl
- ether
- butanol
- compound
- formula
- Prior art date
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- RHLVAWHROJGHTG-UHFFFAOYSA-N 4-(4-phenylphenyl)butan-1-ol Chemical compound C1=CC(CCCCO)=CC=C1C1=CC=CC=C1 RHLVAWHROJGHTG-UHFFFAOYSA-N 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 43
- -1 hydroxymethylene Chemical group 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- KUOBJVBOCPFTTF-UHFFFAOYSA-N 4-(4-phenylphenyl)but-3-en-1-ol Chemical compound C1=CC(C=CCCO)=CC=C1C1=CC=CC=C1 KUOBJVBOCPFTTF-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- LVMCMBNBTAUNJH-UHFFFAOYSA-N 2-(4-phenylphenyl)oxolane Chemical compound C1CCOC1C1=CC=C(C=2C=CC=CC=2)C=C1 LVMCMBNBTAUNJH-UHFFFAOYSA-N 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 116
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000003208 petroleum Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 206010030113 Oedema Diseases 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 239000012280 lithium aluminium hydride Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XSFAQQLHYUBFKV-UHFFFAOYSA-N 4-(4-phenylphenyl)butanoic acid Chemical compound C1=CC(CCCC(=O)O)=CC=C1C1=CC=CC=C1 XSFAQQLHYUBFKV-UHFFFAOYSA-N 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000001741 anti-phlogistic effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BDMXDQCGJDEQBG-UHFFFAOYSA-N 1-(4-phenylphenyl)butane-1,4-diol Chemical compound C1=CC(C(O)CCCO)=CC=C1C1=CC=CC=C1 BDMXDQCGJDEQBG-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000012448 Lithium borohydride Substances 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- QETIJEGIKGOUJT-UHFFFAOYSA-N ethyl 4-(4-phenylphenyl)butanoate Chemical compound C1=CC(CCCC(=O)OCC)=CC=C1C1=CC=CC=C1 QETIJEGIKGOUJT-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 229960002895 phenylbutazone Drugs 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 230000001562 ulcerogenic effect Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 230000002322 anti-exudative effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- ZKYIDZVHHNPNSZ-UHFFFAOYSA-N methyl 4-(4-phenylphenyl)butanoate Chemical compound C1=CC(CCCC(=O)OC)=CC=C1C1=CC=CC=C1 ZKYIDZVHHNPNSZ-UHFFFAOYSA-N 0.000 description 2
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- LJFCDOMDEACIMM-UHFFFAOYSA-N zinc chromium(3+) oxygen(2-) Chemical compound [O-2].[Cr+3].[Zn+2] LJFCDOMDEACIMM-UHFFFAOYSA-N 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- IDGZWZOGXPFMAL-UHFFFAOYSA-N 1-(2-bromoethyl)-4-phenylbenzene Chemical compound C1=CC(CCBr)=CC=C1C1=CC=CC=C1 IDGZWZOGXPFMAL-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- CLGLKAAXNFFWON-UHFFFAOYSA-N 2-(4-phenylphenyl)ethanol Chemical compound C1=CC(CCO)=CC=C1C1=CC=CC=C1 CLGLKAAXNFFWON-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- ZTFXLAHCWFMVDU-UHFFFAOYSA-N 2-[4-(2-fluorophenyl)phenyl]ethanol Chemical group OCCc1ccc(cc1)-c1ccccc1F ZTFXLAHCWFMVDU-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- ASXHBIMJLZHIQU-UHFFFAOYSA-N 4-(2-phenylphenyl)butan-1-ol Chemical class OCCCCC1=CC=CC=C1C1=CC=CC=C1 ASXHBIMJLZHIQU-UHFFFAOYSA-N 0.000 description 1
- ZQHPHTJXHHYYIR-UHFFFAOYSA-N 4-(4-phenylphenyl)butanoyl chloride Chemical compound C1=CC(CCCC(=O)Cl)=CC=C1C1=CC=CC=C1 ZQHPHTJXHHYYIR-UHFFFAOYSA-N 0.000 description 1
- NSPWQBUPDXYLAL-UHFFFAOYSA-N 4-hydroxy-1-(4-phenylphenyl)butan-1-one Chemical compound C1=CC(C(=O)CCCO)=CC=C1C1=CC=CC=C1 NSPWQBUPDXYLAL-UHFFFAOYSA-N 0.000 description 1
- NABGULCRNBRRDQ-UHFFFAOYSA-N 5-(4-phenylphenyl)-3h-furan-2-one Chemical compound O1C(=O)CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 NABGULCRNBRRDQ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 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
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- HKNWKTRXBJXGMT-UHFFFAOYSA-N barium palladium Chemical compound [Pd].[Ba] HKNWKTRXBJXGMT-UHFFFAOYSA-N 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- OSDANZNEPXWSQQ-UHFFFAOYSA-N copper chromium(3+) oxygen(2-) Chemical compound [O--].[Cr+3].[Cu++] OSDANZNEPXWSQQ-UHFFFAOYSA-N 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- UZXQPFDXSJUCSB-OUKQBFOZSA-N ethyl (E)-4-oxo-4-(4-phenylphenyl)but-2-enoate Chemical compound C1(=CC=C(C=C1)C(/C=C/C(=O)OCC)=O)C1=CC=CC=C1 UZXQPFDXSJUCSB-OUKQBFOZSA-N 0.000 description 1
- PMVQNZOSDZOHCO-UHFFFAOYSA-N ethyl 4-oxo-4-(4-phenylphenyl)butanoate Chemical compound C1=CC(C(=O)CCC(=O)OCC)=CC=C1C1=CC=CC=C1 PMVQNZOSDZOHCO-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 150000002241 furanones Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 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
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/24—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part polycyclic without condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/26—Polyhydroxylic alcohols containing only six-membered aromatic rings as cyclic part
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Rheumatology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2151312A DE2151312C3 (de) | 1971-10-15 | 1971-10-15 | 4- (4-Biphen ylyl) -l-butanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO136092B true NO136092B (es) | 1977-04-12 |
| NO136092C NO136092C (no) | 1977-07-20 |
Family
ID=5822378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3683/72A NO136092C (no) | 1971-10-15 | 1972-10-13 | Analogifremgangsm}te for fremstilling av terapeutisk aktiv 4-(4-bifenyl)-1-butanol. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3801654A (es) |
| JP (3) | JPS5320031B2 (es) |
| AT (7) | AT327177B (es) |
| AU (1) | AU469279B2 (es) |
| BE (1) | BE790086A (es) |
| BG (5) | BG20777A3 (es) |
| CA (1) | CA993897A (es) |
| CH (4) | CH589575A5 (es) |
| CS (7) | CS160609B2 (es) |
| DD (1) | DD103233A5 (es) |
| DE (1) | DE2151312C3 (es) |
| DK (1) | DK129573B (es) |
| ES (5) | ES407583A1 (es) |
| FI (1) | FI55984C (es) |
| FR (1) | FR2157860B1 (es) |
| GB (1) | GB1361574A (es) |
| HU (1) | HU164696B (es) |
| IE (1) | IE36775B1 (es) |
| IL (1) | IL40571A (es) |
| NL (1) | NL7213927A (es) |
| NO (1) | NO136092C (es) |
| PH (1) | PH13645A (es) |
| PL (4) | PL83601B1 (es) |
| RO (8) | RO70060A (es) |
| SE (2) | SE399417B (es) |
| SU (7) | SU464106A3 (es) |
| YU (5) | YU255972A (es) |
| ZA (1) | ZA727320B (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053639A (en) * | 1964-01-24 | 1977-10-11 | The Boots Company Limited | Therapeutically active phenylalkane derivatives |
| BE790085A (fr) * | 1971-10-15 | 1973-04-13 | Thomae Gmbh Dr K | Nouveaux 4-(4-biphenylyl)-butanols |
| DE2240438A1 (de) * | 1972-08-17 | 1974-02-28 | Thomae Gmbh Dr K | Neue 2-(4-biphenylyl)-tetrahydrofurane und verfahren zu ihrer herstellung |
| DE2240440A1 (de) * | 1972-08-17 | 1974-02-28 | Thomae Gmbh Dr K | Neue (4-biphenylyl)-alkohole und verfahren zu ihrer herstellung |
| DE2341506A1 (de) * | 1973-08-16 | 1975-02-27 | Thomae Gmbh Dr K | Neue biphenylderivate und verfahren zu ihrer herstellung |
| DE2528958A1 (de) * | 1975-06-28 | 1977-01-13 | Merck Patent Gmbh | Araliphatische dihalogenverbindungen und verfahren zu ihrer herstellung |
| DE2708520A1 (de) * | 1977-02-26 | 1978-08-31 | Thomae Gmbh Dr K | Neue arzneimittelkombinationen und verfahren zu ihrer herstellung |
| DE3001303A1 (de) * | 1980-01-16 | 1981-07-23 | Basf Ag, 6700 Ludwigshafen | Optisch aktive phenylpropan-derivate, ihre herstellung und verwendung |
| AT399471B (de) * | 1993-06-04 | 1995-05-26 | Ifw Manfred Otte Ges M B H & C | Spritzgiessform |
-
0
- BE BE790086D patent/BE790086A/xx not_active IP Right Cessation
-
1971
- 1971-10-15 DE DE2151312A patent/DE2151312C3/de not_active Expired
-
1972
- 1972-09-22 SE SE7212263A patent/SE399417B/xx unknown
- 1972-10-04 US US00294940A patent/US3801654A/en not_active Expired - Lifetime
- 1972-10-05 AT AT573873*7A patent/AT327177B/de not_active IP Right Cessation
- 1972-10-05 AT AT573673A patent/AT321897B/de not_active IP Right Cessation
- 1972-10-05 AT AT852372A patent/AT315823B/de not_active IP Right Cessation
- 1972-10-05 AT AT573573A patent/AT321898B/de not_active IP Right Cessation
- 1972-10-05 AT AT573473A patent/AT321899B/de not_active IP Right Cessation
- 1972-10-05 AT AT573373A patent/AT321901B/de not_active IP Right Cessation
- 1972-10-05 AT AT573773A patent/AT321900B/de not_active IP Right Cessation
- 1972-10-06 PH PH13983A patent/PH13645A/en unknown
- 1972-10-11 DD DD166149A patent/DD103233A5/xx unknown
- 1972-10-12 YU YU02559/72A patent/YU255972A/xx unknown
- 1972-10-12 SU SU1955030A patent/SU464106A3/ru active
- 1972-10-12 SU SU1957826A patent/SU474968A3/ru active
- 1972-10-12 SU SU1955028A patent/SU471710A3/ru active
- 1972-10-12 SU SU1839112A patent/SU453823A3/ru active
- 1972-10-12 SU SU1955026A patent/SU464105A3/ru active
- 1972-10-13 BG BG23546A patent/BG20777A3/xx unknown
- 1972-10-13 BG BG21617A patent/BG20560A3/xx unknown
- 1972-10-13 PL PL1972158243A patent/PL83601B1/pl unknown
- 1972-10-13 CS CS6922A patent/CS160609B2/cs unknown
- 1972-10-13 CS CS5229*[A patent/CS160613B2/cs unknown
- 1972-10-13 CA CA153,847A patent/CA993897A/en not_active Expired
- 1972-10-13 BG BG23543A patent/BG19586A3/xx unknown
- 1972-10-13 NL NL7213927A patent/NL7213927A/xx not_active Application Discontinuation
- 1972-10-13 PL PL1972173621A patent/PL91407B1/pl unknown
- 1972-10-13 GB GB4744272A patent/GB1361574A/en not_active Expired
- 1972-10-13 CH CH63676A patent/CH589575A5/xx not_active IP Right Cessation
- 1972-10-13 BG BG23545A patent/BG20333A3/xx unknown
- 1972-10-13 JP JP10314872A patent/JPS5320031B2/ja not_active Expired
- 1972-10-13 ZA ZA727320A patent/ZA727320B/xx unknown
- 1972-10-13 NO NO3683/72A patent/NO136092C/no unknown
- 1972-10-13 CS CS5231*[A patent/CS160615B2/cs unknown
- 1972-10-13 CS CS5230*[A patent/CS160614B2/cs unknown
- 1972-10-13 FR FR7236362A patent/FR2157860B1/fr not_active Expired
- 1972-10-13 CH CH1500072A patent/CH575358A5/xx not_active IP Right Cessation
- 1972-10-13 CS CS5226*[A patent/CS160610B2/cs unknown
- 1972-10-13 HU HUTO891A patent/HU164696B/hu unknown
- 1972-10-13 DK DK506872AA patent/DK129573B/da not_active IP Right Cessation
- 1972-10-13 IL IL40571A patent/IL40571A/xx unknown
- 1972-10-13 CH CH72676A patent/CH590185A5/xx not_active IP Right Cessation
- 1972-10-13 ES ES407583A patent/ES407583A1/es not_active Expired
- 1972-10-13 IE IE1394/72A patent/IE36775B1/xx unknown
- 1972-10-13 PL PL1972173620A patent/PL91409B1/pl unknown
- 1972-10-13 FI FI2841/72A patent/FI55984C/fi active
- 1972-10-13 CS CS5227*[A patent/CS160611B2/cs unknown
- 1972-10-13 AU AU47748/72A patent/AU469279B2/en not_active Expired
- 1972-10-13 PL PL1972173619A patent/PL91408B1/pl unknown
- 1972-10-13 BG BG23544A patent/BG20332A3/xx unknown
- 1972-10-13 CS CS5228*[A patent/CS160612B2/cs unknown
- 1972-10-15 RO RO7283157A patent/RO70060A/ro unknown
- 1972-10-15 RO RO7283159A patent/RO71306A/ro unknown
- 1972-10-15 RO RO7283156A patent/RO69378A/ro unknown
- 1972-10-15 RO RO7283154A patent/RO70059A/ro unknown
- 1972-10-15 RO RO7283160A patent/RO71307A/ro unknown
- 1972-10-15 RO RO7283155A patent/RO70567A/ro unknown
- 1972-10-16 RO RO7283153A patent/RO70058A/ro unknown
- 1972-10-16 RO RO7272524A patent/RO71244A/ro unknown
-
1973
- 1973-05-26 ES ES415242A patent/ES415242A1/es not_active Expired
- 1973-05-26 ES ES415241A patent/ES415241A1/es not_active Expired
- 1973-05-26 ES ES415244A patent/ES415244A1/es not_active Expired
- 1973-05-26 ES ES415243A patent/ES415243A1/es not_active Expired
- 1973-08-23 SU SU1955347A patent/SU496713A3/ru active
- 1973-08-23 SU SU1955029A patent/SU496714A3/ru active
-
1976
- 1976-01-26 SE SE7600800A patent/SE7600800L/xx unknown
- 1976-04-29 CH CH206977A patent/CH599082A5/xx not_active IP Right Cessation
-
1977
- 1977-09-09 JP JP10868477A patent/JPS5387342A/ja active Granted
- 1977-09-09 JP JP10868377A patent/JPS5387341A/ja active Granted
-
1979
- 1979-08-13 YU YU01974/79A patent/YU197479A/xx unknown
- 1979-08-13 YU YU01973/79A patent/YU197379A/xx unknown
- 1979-08-13 YU YU01971/79A patent/YU197179A/xx unknown
- 1979-08-13 YU YU01972/79A patent/YU197279A/xx unknown
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