FI57929C - Foerfarande foer framstaellning av terapeutiskt vaerdefull bifenyl - Google Patents
Foerfarande foer framstaellning av terapeutiskt vaerdefull bifenyl Download PDFInfo
- Publication number
- FI57929C FI57929C FI1907/73A FI190773A FI57929C FI 57929 C FI57929 C FI 57929C FI 1907/73 A FI1907/73 A FI 1907/73A FI 190773 A FI190773 A FI 190773A FI 57929 C FI57929 C FI 57929C
- Authority
- FI
- Finland
- Prior art keywords
- hydroxy
- group
- halogen
- cooh
- biphenylyl
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004074 biphenyls Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 241000277284 Salvelinus fontinalis Species 0.000 claims 1
- 230000000911 decarboxylating effect Effects 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 239000000543 intermediate Substances 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000003208 petroleum Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000009835 boiling Methods 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- 235000019260 propionic acid Nutrition 0.000 description 13
- 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 13
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- -1 tetrahydropyranyloxy group Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YFVOFFKNHQTQQE-UHFFFAOYSA-N 1-(4-bromo-3-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C([N+]([O-])=O)=C1 YFVOFFKNHQTQQE-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CNVQKQRUQRLPQS-UHFFFAOYSA-N 2-(3-hydroxy-4-phenylphenyl)propanoic acid Chemical compound OC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 CNVQKQRUQRLPQS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 206010003246 arthritis Diseases 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000001119 stannous chloride Substances 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- QFEDDRCGUJGZIJ-UHFFFAOYSA-N 1-[3-amino-4-(4-chloro-2-methoxyphenyl)phenyl]ethanone Chemical group COC1=CC(Cl)=CC=C1C1=CC=C(C(C)=O)C=C1N QFEDDRCGUJGZIJ-UHFFFAOYSA-N 0.000 description 2
- XGTZNDGDQUFLTL-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-3-methoxyphenyl]ethanone Chemical group COC1=CC(C(C)=O)=CC=C1C1=CC=C(Cl)C=C1 XGTZNDGDQUFLTL-UHFFFAOYSA-N 0.000 description 2
- MEGCHWGZNPUMAV-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1O MEGCHWGZNPUMAV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000008096 xylene Substances 0.000 description 2
- SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 1
- UPTMYZNKOOVWEB-UHFFFAOYSA-N 1-[2-(4-chloro-2-methoxyphenyl)phenyl]ethanone Chemical group C(C)(=O)C1=C(C=CC=C1)C1=C(C=C(C=C1)Cl)OC UPTMYZNKOOVWEB-UHFFFAOYSA-N 0.000 description 1
- SDHJWIGSKFZUGY-UHFFFAOYSA-N 1-[3-amino-4-(2,4-difluorophenyl)phenyl]ethanone Chemical group NC1=CC(C(=O)C)=CC=C1C1=CC=C(F)C=C1F SDHJWIGSKFZUGY-UHFFFAOYSA-N 0.000 description 1
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- KDKVLQIDNRFDDF-UHFFFAOYSA-N 1-[3-hydroxy-4-(4-methoxyphenyl)phenyl]ethanone Chemical group C1=CC(OC)=CC=C1C1=CC=C(C(C)=O)C=C1O KDKVLQIDNRFDDF-UHFFFAOYSA-N 0.000 description 1
- RYFFNRQSICUCLJ-UHFFFAOYSA-N 1-[4-(2,4-dimethoxyphenyl)-3-nitrophenyl]ethanone Chemical group COC1=CC(OC)=CC=C1C1=CC=C(C(C)=O)C=C1[N+]([O-])=O RYFFNRQSICUCLJ-UHFFFAOYSA-N 0.000 description 1
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- GVYWMDOWAKBHQA-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)phenyl]propanoic acid Chemical compound COC1=CC=CC=C1C1=CC=C(C(C)C(O)=O)C=C1 GVYWMDOWAKBHQA-UHFFFAOYSA-N 0.000 description 1
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- VBFLUCIGUGAYJU-UHFFFAOYSA-N 2-[4-(4-chloro-2-fluorophenyl)-3-methoxyphenyl]propanal Chemical compound COC1=CC(C(C)C=O)=CC=C1C1=CC=C(Cl)C=C1F VBFLUCIGUGAYJU-UHFFFAOYSA-N 0.000 description 1
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- CIAOQHUPIWPDQV-UHFFFAOYSA-N 2-[4-(4-chloro-2-methoxyphenyl)phenyl]propanal Chemical compound ClC1=CC(=C(C=C1)C1=CC=C(C=C1)C(C=O)C)OC CIAOQHUPIWPDQV-UHFFFAOYSA-N 0.000 description 1
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- NDMPRFCNOYMCLE-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-3-methoxyphenyl]propanal Chemical compound COC1=CC(C(C)C=O)=CC=C1C1=CC=C(F)C=C1 NDMPRFCNOYMCLE-UHFFFAOYSA-N 0.000 description 1
- AMEXCCWVSBTYAM-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)-3-methoxyphenyl]propanoic acid Chemical compound COC1=CC(C(C)C(O)=O)=CC=C1C1=CC=C(F)C=C1 AMEXCCWVSBTYAM-UHFFFAOYSA-N 0.000 description 1
- LVKCDOUIWQEMCI-UHFFFAOYSA-N 2-[4-(4-hydroxyphenyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=C(O)C=C1 LVKCDOUIWQEMCI-UHFFFAOYSA-N 0.000 description 1
- XCAOWJIVGZXNIR-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)phenyl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(C)C(O)=O)C=C1 XCAOWJIVGZXNIR-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- HCEZWZZQCVGDPZ-UHFFFAOYSA-N CC(C1=C(C(=C(C=C1)C2=CC=CC=C2)OC)OC)C(=O)O Chemical compound CC(C1=C(C(=C(C=C1)C2=CC=CC=C2)OC)OC)C(=O)O HCEZWZZQCVGDPZ-UHFFFAOYSA-N 0.000 description 1
- GWYDJTJZVYZQJU-UHFFFAOYSA-N CC(C1=C(C=C(C(=C1F)OC)C2=CC=CC=C2)F)C(=O)O Chemical compound CC(C1=C(C=C(C(=C1F)OC)C2=CC=CC=C2)F)C(=O)O GWYDJTJZVYZQJU-UHFFFAOYSA-N 0.000 description 1
- YTKAVLFBISRQBX-UHFFFAOYSA-N CC(C=O)C1(CC(=C(C=C1)C2=CC=CC=C2OC)Cl)OC Chemical compound CC(C=O)C1(CC(=C(C=C1)C2=CC=CC=C2OC)Cl)OC YTKAVLFBISRQBX-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- RUMGUGBCAUMVIP-UHFFFAOYSA-N OC1=C(C=CC(=C1)CC(=O)O)C1=CC=CC=C1 Chemical compound OC1=C(C=CC(=C1)CC(=O)O)C1=CC=CC=C1 RUMGUGBCAUMVIP-UHFFFAOYSA-N 0.000 description 1
- 208000000114 Pain Threshold Diseases 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
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- 239000003125 aqueous solvent Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000011436 cob Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000020335 dealkylation Effects 0.000 description 1
- 238000006900 dealkylation reaction Methods 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- NXPHCVPFHOVZBC-UHFFFAOYSA-N hydroxylamine;sulfuric acid Chemical compound ON.OS(O)(=O)=O NXPHCVPFHOVZBC-UHFFFAOYSA-N 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NEEBGNCVINGBCR-UHFFFAOYSA-N methyl 2-(3-hydroxy-4-phenylphenyl)propanoate Chemical compound OC1=CC(C(C)C(=O)OC)=CC=C1C1=CC=CC=C1 NEEBGNCVINGBCR-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 230000001047 pyretic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RMADEAIMDSHWHU-UHFFFAOYSA-M sodium;2-(3-hydroxy-4-phenylphenyl)propanoate Chemical compound [Na+].OC1=CC(C(C([O-])=O)C)=CC=C1C1=CC=CC=C1 RMADEAIMDSHWHU-UHFFFAOYSA-M 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D263/14—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/002—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by transformation of a functional group, e.g. oxo, carboxyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- 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
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- 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
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2810472 | 1972-06-15 | ||
GB2810472A GB1396726A (en) | 1972-06-15 | 1972-06-15 | Phenylalkanoic acids |
Publications (2)
Publication Number | Publication Date |
---|---|
FI57929B FI57929B (fi) | 1980-07-31 |
FI57929C true FI57929C (fi) | 1980-11-10 |
Family
ID=10270338
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI1907/73A FI57929C (fi) | 1972-06-15 | 1973-06-13 | Foerfarande foer framstaellning av terapeutiskt vaerdefull bifenyl |
Country Status (26)
Country | Link |
---|---|
US (1) | US3969402A (en, 2012) |
JP (1) | JPS4961144A (en, 2012) |
AR (1) | AR211760A1 (en, 2012) |
AT (1) | AT329036B (en, 2012) |
BE (1) | BE800951A (en, 2012) |
CA (1) | CA1012151A (en, 2012) |
CH (1) | CH584180A5 (en, 2012) |
CS (1) | CS176239B2 (en, 2012) |
DD (1) | DD108977A5 (en, 2012) |
DE (1) | DE2329125A1 (en, 2012) |
ES (1) | ES415919A1 (en, 2012) |
FI (1) | FI57929C (en, 2012) |
FR (1) | FR2189036B1 (en, 2012) |
GB (1) | GB1396726A (en, 2012) |
HU (1) | HU167229B (en, 2012) |
IE (1) | IE38031B1 (en, 2012) |
IL (1) | IL42447A (en, 2012) |
LU (1) | LU67781A1 (en, 2012) |
NL (1) | NL7308349A (en, 2012) |
NO (1) | NO138061C (en, 2012) |
PL (1) | PL102580B1 (en, 2012) |
RO (1) | RO62810A (en, 2012) |
SE (1) | SE409855B (en, 2012) |
SU (1) | SU578854A3 (en, 2012) |
YU (1) | YU155673A (en, 2012) |
ZA (1) | ZA734053B (en, 2012) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4205176A (en) * | 1978-10-18 | 1980-05-27 | Cincinnati Milacron Chemicals Inc. | Ester substituted oxazolines |
US4247466A (en) * | 1979-07-05 | 1981-01-27 | American Cyanamid Company | Lactone metabolites of 3-(4-biphenylylcarbonyl)propionic acid |
JPS5735543A (en) * | 1980-08-13 | 1982-02-26 | Hisamitsu Pharmaceut Co Inc | Novel phenylacetic acid derivative |
JPS5762239A (en) * | 1980-08-26 | 1982-04-15 | Hisamitsu Pharmaceut Co Inc | Novel phenylacetic acid derivative |
DE3049405A1 (de) * | 1980-12-23 | 1982-07-15 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue derivate von antiphlogistisch wirksamen carbonsaeuren, ihre herstellung und medizinische anwendung |
US4792560A (en) * | 1985-04-03 | 1988-12-20 | Rorer Pharmaceutical Corporation | Quinoline hydroxamates and their use as modulators of arachidonic acid metabolic pathways |
US5218124A (en) * | 1989-10-27 | 1993-06-08 | American Home Products Corporation | Substituted benzoylbenzene-, biphenyl- and 2-oxazole-alkanoic acid derivatives as inhibitors of pla2 and lipoxygenase |
US5071988A (en) * | 1989-10-27 | 1991-12-10 | American Home Products Corporation | Substituted benzoylbenzene-, biphenyl- and 2-oxazole-alkanoic acid derivatives |
PH30449A (en) * | 1991-11-25 | 1997-05-28 | Lilly Co Eli | Substituted phenyl phenol leukotriene antagonists |
AU684674B2 (en) * | 1994-10-06 | 1997-12-18 | Bayer Aktiengesellschaft | Substituted diphenyl oxazolines |
FR2744445B1 (fr) * | 1996-02-01 | 1998-10-02 | Roussel Uclaf | Composes biphenyles nouveaux et/ou a titre de medicament, compositions pharmaceutiques les contenant, leur procede de preparation et les intermediaires de ce procede |
FR2880885B1 (fr) * | 2005-01-14 | 2009-01-30 | Merck Sante Soc Par Actions Si | Derives d'acide phenylbenzoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique |
CA2643670A1 (en) * | 2006-02-27 | 2007-08-30 | Sterix Limited | Diaryl compounds as non-steroidal inhibitors of 17-beta hydroxysteroid dehydrogenase and/or steroid sulphatase for the treatment of oestrogen-related diseases such as hormone dependent breast cancer |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1091403A (en) * | 1964-01-24 | 1967-11-15 | Boots Pure Drug Co Ltd | Therapeutically active phenylalkane derivatives |
US3624142A (en) * | 1964-09-10 | 1971-11-30 | Merck & Co Inc | Substituted biphenyl acetic acid derivatives |
US3671580A (en) * | 1969-12-22 | 1972-06-20 | Merck & Co Inc | Substituted biphenyl acetic acids and ester derivatives thereof |
-
1972
- 1972-06-15 GB GB2810472A patent/GB1396726A/en not_active Expired
-
1973
- 1973-05-31 IE IE875/73A patent/IE38031B1/xx unknown
- 1973-06-05 IL IL42447A patent/IL42447A/en unknown
- 1973-06-06 US US05/367,614 patent/US3969402A/en not_active Expired - Lifetime
- 1973-06-07 DE DE2329125A patent/DE2329125A1/de not_active Withdrawn
- 1973-06-11 YU YU01556/73A patent/YU155673A/xx unknown
- 1973-06-12 RO RO7300075114A patent/RO62810A/ro unknown
- 1973-06-12 DD DD171483A patent/DD108977A5/xx unknown
- 1973-06-13 FI FI1907/73A patent/FI57929C/fi active
- 1973-06-13 LU LU67781A patent/LU67781A1/xx unknown
- 1973-06-13 SE SE7308350A patent/SE409855B/xx unknown
- 1973-06-13 HU HUBO1444A patent/HU167229B/hu unknown
- 1973-06-14 ES ES415919A patent/ES415919A1/es not_active Expired
- 1973-06-14 CA CA174,008A patent/CA1012151A/en not_active Expired
- 1973-06-14 CH CH865173A patent/CH584180A5/xx not_active IP Right Cessation
- 1973-06-14 NO NO2479/73A patent/NO138061C/no unknown
- 1973-06-14 SU SU7301934985A patent/SU578854A3/ru active
- 1973-06-14 AT AT522873A patent/AT329036B/de not_active IP Right Cessation
- 1973-06-14 CS CS4320A patent/CS176239B2/cs unknown
- 1973-06-14 ZA ZA734053A patent/ZA734053B/xx unknown
- 1973-06-14 JP JP48067328A patent/JPS4961144A/ja active Pending
- 1973-06-15 NL NL7308349A patent/NL7308349A/xx not_active Application Discontinuation
- 1973-06-15 PL PL1973163373A patent/PL102580B1/pl unknown
- 1973-06-15 BE BE132294A patent/BE800951A/xx unknown
- 1973-06-15 AR AR248602A patent/AR211760A1/es active
- 1973-06-15 FR FR7321853A patent/FR2189036B1/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
ES415919A1 (es) | 1976-05-16 |
IE38031L (en) | 1973-12-15 |
US3969402A (en) | 1976-07-13 |
DE2329125A1 (de) | 1974-01-03 |
YU155673A (en) | 1981-04-30 |
IE38031B1 (en) | 1977-12-07 |
SE409855B (sv) | 1979-09-10 |
DD108977A5 (en, 2012) | 1974-10-12 |
NO138061B (no) | 1978-03-13 |
ZA734053B (en) | 1974-05-29 |
RO62810A (fr) | 1978-01-15 |
AU5700173A (en) | 1974-12-19 |
IL42447A0 (en) | 1973-08-29 |
AT329036B (de) | 1976-04-26 |
LU67781A1 (en, 2012) | 1973-08-16 |
NO138061C (no) | 1978-06-21 |
SU578854A3 (ru) | 1977-10-30 |
FR2189036B1 (en, 2012) | 1980-04-11 |
CA1012151A (en) | 1977-06-14 |
HU167229B (en, 2012) | 1975-09-27 |
AR211760A1 (es) | 1978-03-15 |
CH584180A5 (en, 2012) | 1977-01-31 |
GB1396726A (en) | 1975-06-04 |
CS176239B2 (en, 2012) | 1977-06-30 |
FR2189036A1 (en, 2012) | 1974-01-25 |
NL7308349A (en, 2012) | 1973-12-18 |
JPS4961144A (en, 2012) | 1974-06-13 |
IL42447A (en) | 1977-05-31 |
ATA522873A (de) | 1975-07-15 |
BE800951A (fr) | 1973-12-17 |
FI57929B (fi) | 1980-07-31 |
PL102580B1 (pl) | 1979-04-30 |
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