DE2240441A1 - Neue biphenylderivate und verfahren zur herstellung - Google Patents
Neue biphenylderivate und verfahren zur herstellungInfo
- Publication number
- DE2240441A1 DE2240441A1 DE2240441A DE2240441A DE2240441A1 DE 2240441 A1 DE2240441 A1 DE 2240441A1 DE 2240441 A DE2240441 A DE 2240441A DE 2240441 A DE2240441 A DE 2240441A DE 2240441 A1 DE2240441 A1 DE 2240441A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- group
- compounds
- biphenylyl
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 27
- -1 (- biphenylyl) -3-hydroxy-butyric acid Chemical compound 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000007529 inorganic bases Chemical class 0.000 claims description 10
- 150000007530 organic bases Chemical class 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Chemical class 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910000043 hydrogen iodide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 2
- 150000008043 acidic salts Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 206010030113 Oedema Diseases 0.000 description 15
- 238000003756 stirring Methods 0.000 description 14
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 13
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 239000013543 active substance Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000008120 corn starch Substances 0.000 description 9
- 229940099112 cornstarch Drugs 0.000 description 9
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 9
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 9
- 239000000829 suppository Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 150000003946 cyclohexylamines Chemical class 0.000 description 5
- 239000008298 dragée Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 235000010418 carrageenan Nutrition 0.000 description 4
- 229920001525 carrageenan Polymers 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- DOGMWDLAWMDDHW-UHFFFAOYSA-N 3-[4-(2-fluorophenyl)phenyl]butanoic acid Chemical compound C1=CC(C(CC(O)=O)C)=CC=C1C1=CC=CC=C1F DOGMWDLAWMDDHW-UHFFFAOYSA-N 0.000 description 3
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 3
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 230000002322 anti-exudative effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 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
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229960001462 sodium cyclamate Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 230000001960 triggered effect Effects 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000282376 Panthera tigris Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax 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
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 210000000548 hind-foot Anatomy 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PASUFCLLJYIBHP-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1F PASUFCLLJYIBHP-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- SKXKMFFXSTWOAA-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)phenyl]butanoic acid Chemical compound C1=CC(C(CC(O)=O)C)=CC=C1C1=CC=CC=C1Cl SKXKMFFXSTWOAA-UHFFFAOYSA-N 0.000 description 1
- GFFAAVLHFBGSEB-UHFFFAOYSA-N 3-[4-(2-fluorophenyl)phenyl]-3-hydroxybutanoic acid Chemical compound FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CC(=O)O)(C)O GFFAAVLHFBGSEB-UHFFFAOYSA-N 0.000 description 1
- HQKWWDRSCKHETN-UHFFFAOYSA-N 3-[4-(2-fluorophenyl)phenyl]butanamide Chemical compound C1=CC(C(CC(N)=O)C)=CC=C1C1=CC=CC=C1F HQKWWDRSCKHETN-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- XQKLFJUJTVMQBF-UHFFFAOYSA-N CCOC(CC(C)(C(C=C1)=CC=C1C(C=CC=C1)=C1Cl)O)=O Chemical compound CCOC(CC(C)(C(C=C1)=CC=C1C(C=CC=C1)=C1Cl)O)=O XQKLFJUJTVMQBF-UHFFFAOYSA-N 0.000 description 1
- QEKSZZVVKYZANM-UHFFFAOYSA-N CNC(CC(C)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O Chemical compound CNC(CC(C)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O QEKSZZVVKYZANM-UHFFFAOYSA-N 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- OKBWIJWBIFQJPZ-UHFFFAOYSA-N FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CC(=O)Cl)C Chemical compound FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CC(=O)Cl)C OKBWIJWBIFQJPZ-UHFFFAOYSA-N 0.000 description 1
- TUDZKWCNKSDFKZ-UHFFFAOYSA-N FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CC(=O)OCC)(C)O Chemical compound FC1=C(C=CC=C1)C1=CC=C(C=C1)C(CC(=O)OCC)(C)O TUDZKWCNKSDFKZ-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- POTZATWUSJKAQN-UHFFFAOYSA-N OC1=CC=C(C=C1)NC(CC(C)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O Chemical compound OC1=CC=C(C=C1)NC(CC(C)C1=CC=C(C=C1)C1=C(C=CC=C1)F)=O POTZATWUSJKAQN-UHFFFAOYSA-N 0.000 description 1
- 241001478272 Salmonella enterica subsp. enterica serovar Banana Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 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
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 239000001582 butter acid Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 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 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/208—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being MX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- 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
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide 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
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (79)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2240441A DE2240441A1 (de) | 1972-08-17 | 1972-08-17 | Neue biphenylderivate und verfahren zur herstellung |
AT785173A ATA785173A (de) | 1972-08-17 | 1972-09-13 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-hydroxy-buttersaeureamiden |
ES417792A ES417792A1 (es) | 1972-08-17 | 1973-08-11 | Procedimiento para la preparacion de nuevos derivados de bifenilo. |
AT710773A AT323143B (de) | 1972-08-17 | 1973-08-14 | Verfahren zur herstellung neuer biphenylderivate |
CH1170773A CH588435A5 (pl) | 1972-08-17 | 1973-08-14 | |
AT710873A AT323144B (de) | 1972-08-17 | 1973-08-14 | Verfahren zur herstellung neuer biphenylderivate |
ES417883A ES417883A1 (es) | 1972-08-17 | 1973-08-14 | Procedimiento para la preparacion de derivados de bifenilo. |
ES417884A ES417884A1 (es) | 1972-08-17 | 1973-08-14 | Procedimiento para la preparacion de derivados de bifenilo. |
AT711273A AT328427B (de) | 1972-08-17 | 1973-08-14 | Verfahren zur herstellung neuer 3- (4-biphenylyl) -buttersauren, deren ester, amide, deren optisch aktiven isomeren und salze |
BG27671A BG21844A3 (pl) | 1972-08-17 | 1973-08-15 | |
BG24328A BG22069A3 (pl) | 1972-08-17 | 1973-08-15 | |
HUTO925A HU166516B (pl) | 1972-08-17 | 1973-08-15 | |
SU1958291A SU482039A3 (ru) | 1972-08-17 | 1973-08-15 | Способ получени бифенилилбутеновых кислот или их производных |
BG27679A BG21846A3 (pl) | 1972-08-17 | 1973-08-15 | |
BG24326A BG21010A3 (pl) | 1972-08-17 | 1973-08-15 | |
SU1958288A SU484679A3 (ru) | 1972-08-17 | 1973-08-15 | Способ получени производных бифенила |
BG24327A BG21197A3 (pl) | 1972-08-17 | 1973-08-15 | |
DD177432*A DD111204A5 (pl) | 1972-08-17 | 1973-08-15 | |
DD172904A DD107900A5 (pl) | 1972-08-17 | 1973-08-15 | |
DD172906A DD108071A5 (pl) | 1972-08-17 | 1973-08-15 | |
SU1958290A SU511846A3 (ru) | 1972-08-17 | 1973-08-15 | Способ получени -бифенилмасл ных кислот или их солей |
BG27680A BG21847A3 (pl) | 1972-08-17 | 1973-08-15 | |
DD172907A DD107901A5 (pl) | 1972-08-17 | 1973-08-15 | |
HUTO924A HU168129B (pl) | 1972-08-17 | 1973-08-15 | |
HUTO926A HU166517B (pl) | 1972-08-17 | 1973-08-15 | |
JP48092053A JPS49124052A (pl) | 1972-08-17 | 1973-08-16 | |
ZA00735616A ZA735616B (en) | 1972-08-17 | 1973-08-16 | Improvements relating to biphenylyl derivatives |
NL7311301A NL7311301A (pl) | 1972-08-17 | 1973-08-16 | |
AU59307/73A AU476339B2 (en) | 1972-08-17 | 1973-08-16 | Halo-4-biphenylyl-butyric acids, esters and amides and pharmaceutical compositions containing them |
JP48092052A JPS49124051A (pl) | 1972-08-17 | 1973-08-16 | |
PL1973164708A PL90397B1 (pl) | 1972-08-17 | 1973-08-16 | |
ZA00735629A ZA735629B (en) | 1972-08-17 | 1973-08-16 | Improvements relating to biphenylyl derivates |
IL43002A IL43002A0 (en) | 1972-08-17 | 1973-08-16 | Novel biphenylyl derivatives,their preparation and pharmaceutical compositions containing them |
IL43003A IL43003A0 (en) | 1972-08-17 | 1973-08-16 | Novel biphenyl derivatives,their preparation and pharmaceutical compositions containing them |
GB3884473A GB1410852A (en) | 1972-08-17 | 1973-08-16 | Substituted 4-biphenylyl-butenoic acids esters and amides and pharmaceutical compositions containing them |
PL1973186474A PL94510B1 (pl) | 1972-08-17 | 1973-08-16 | Sposob wytwarzania nowych amidow kwasu 3-(4-bifenylilo)-2-propenokarboksylowego |
AU59308/73A AU5930873A (en) | 1972-08-17 | 1973-08-16 | Biphenylyl alkanoic acids |
GB3884373A GB1411495A (en) | 1972-08-17 | 1973-08-16 | Substituted-4-biphenyl-3-hydroxybutyric acids esters and amides and pharmaceutical compositions containing them |
AU59309/73A AU476340B2 (en) | 1972-08-17 | 1973-08-16 | Substituted 4-biphenylyl-butenoic acids, esters and amides and pharmaceutical compositions containing them |
JP9205173A JPS5525173B2 (pl) | 1972-08-17 | 1973-08-16 | |
CS4904A CS165387B2 (pl) | 1972-08-17 | 1973-08-16 | |
ZA00735628A ZA735628B (en) | 1972-08-17 | 1973-08-16 | Improvements relating to biphenylyl derivates |
IL43004A IL43004A0 (en) | 1972-08-17 | 1973-08-16 | Novel biphenylyl derivatives,their preparation and pharmaceutical compositions containing them |
NL7311300A NL7311300A (pl) | 1972-08-17 | 1973-08-16 | |
CS4903A CS165386B2 (pl) | 1972-08-17 | 1973-08-16 | |
GB3884273A GB1434090A (en) | 1972-08-17 | 1973-08-16 | Halo-4-biphenylyl-butyric acid esters and amides and pharma ceutical compositions containing them |
CS5793A CS165385B2 (pl) | 1972-08-17 | 1973-08-16 | |
BE134691A BE803734A (fr) | 1972-08-17 | 1973-08-17 | Nouveaux derives de biphenyle et procedes de preparation de ces derives |
BE134689A BE803732A (fr) | 1972-08-17 | 1973-08-17 | Nouveaux derives de biphenyle et procedes pour les fabriquer |
NL7311355A NL7311355A (pl) | 1972-08-17 | 1973-08-17 | |
FR7330079A FR2196171B1 (pl) | 1972-08-17 | 1973-08-17 | |
FR7330076A FR2196168B1 (pl) | 1972-08-17 | 1973-08-17 | |
RO7300075822A RO62918A (fr) | 1972-08-17 | 1973-08-17 | Procede pour la preparation des derives du biphenyle |
FR7330075A FR2196167B1 (pl) | 1972-08-17 | 1973-08-17 | |
BE134690A BE803733A (fr) | 1972-08-17 | 1973-08-17 | Nouveaux derives de biphenyle et procede de preparation de ces derives |
RO7300075821A RO62917A (fr) | 1972-08-17 | 1973-08-17 | Procede pour obtenir des derives du diphenyle |
AT837274A AT332383B (de) | 1972-08-17 | 1974-10-18 | Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, ihrer ester, amide und salze |
AT838074A AT332385B (de) | 1972-08-17 | 1974-10-18 | Zylindrischer drehschieber für hubkolbenbrennkraftmaschinen |
AT837374A AT332384B (de) | 1972-08-17 | 1974-10-18 | Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, deren estern, amiden und salzen |
SU2069576A SU561505A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени 3-(4-бифенилил) -масл ной кислоты или ее солей |
SU2069771A SU520030A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилмасл ной кислоты или ее эфира или ее соли |
SU2069111A SU526284A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилмасл ной кислоты или ее амида или соли |
SU2069114A SU538658A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени бифенилмасл ных кислот или их солей, или рацематов, или оптически активных антиподов |
SU2069737A SU520908A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилилмасл ной кислоты или ее эфира или ее соли |
SU2069113A SU545250A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилилмасл ной кислоты или ее сложных эфиров или ее солей |
SU2069772A SU517245A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилмасл ной кислоты или ее соли |
SU2069110A SU554810A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени производных бифенила или их солей, или рацематов, или оптически активных антиподов |
SU2069738A SU519122A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилмасл ной кислоты или ее соли |
SU2069774A SU552021A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени производных бифенила или их солей |
SU2069577A SU520907A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилилмасл ной кислоты или ее соли |
SU7402069575A SU577967A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилилмасл ной кислоты или ее эфиров или ее амидов или ее солей |
SU2069578A SU511847A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилмасл ной кислоты или ее эфиров или солей |
SU2069116A SU517244A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилилмасл ной кислоты или ее соли |
ES432464A ES432464A1 (es) | 1972-08-17 | 1974-11-30 | Procedimiento para la preparacion de nuevos derivados de bi-fenilo. |
ES432465A ES432465A1 (es) | 1972-08-17 | 1974-11-30 | Procedimiento para la preparacion de nuevos derivados de bifenilo. |
US05/577,170 US3987197A (en) | 1972-08-17 | 1975-05-14 | 3-(2'-fluoro-4-biphenylyl)-butyric acid and salts thereof |
AT611075A AT336592B (de) | 1972-08-17 | 1975-08-07 | Verfahren zur herstellung neuer 3-(4- biphenylyl)-buttersauren, deren estern, amiden und salzen |
AT837775A ATA837775A (de) | 1972-08-17 | 1975-11-04 | Verfahren zur herstellung neuer 3- (4-biphenylyl) -buttersauren, ihrer ester, amide und salze |
AT837875A ATA837875A (de) | 1972-08-17 | 1975-11-04 | Verfahren zur herstellung neuer 3- (4-biphenylyl)-buttersauren, ihrer ester, amide und salze |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2240441A DE2240441A1 (de) | 1972-08-17 | 1972-08-17 | Neue biphenylderivate und verfahren zur herstellung |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2240441A1 true DE2240441A1 (de) | 1974-02-28 |
Family
ID=5853790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2240441A Pending DE2240441A1 (de) | 1972-08-17 | 1972-08-17 | Neue biphenylderivate und verfahren zur herstellung |
Country Status (19)
Country | Link |
---|---|
JP (2) | JPS49124052A (pl) |
AT (3) | AT323144B (pl) |
AU (2) | AU476340B2 (pl) |
BE (3) | BE803733A (pl) |
BG (3) | BG21844A3 (pl) |
CH (1) | CH588435A5 (pl) |
CS (3) | CS165385B2 (pl) |
DD (2) | DD107901A5 (pl) |
DE (1) | DE2240441A1 (pl) |
ES (4) | ES417884A1 (pl) |
FR (2) | FR2196168B1 (pl) |
GB (2) | GB1410852A (pl) |
HU (2) | HU166516B (pl) |
IL (2) | IL43003A0 (pl) |
NL (2) | NL7311300A (pl) |
PL (2) | PL90397B1 (pl) |
RO (2) | RO62917A (pl) |
SU (11) | SU482039A3 (pl) |
ZA (3) | ZA735629B (pl) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2457275A1 (fr) * | 1979-05-21 | 1980-12-19 | Fabre Sa Pierre | Acides p-biphenyl-4 methyl-2 buten-3 oiques utiles dans le traitement des rhumatismes |
RU2686489C1 (ru) * | 2018-12-27 | 2019-04-29 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный университет (СПбГУ)" | Способ получения α-диазокарбонильных соединений в водной среде |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1382267A (en) * | 1970-05-05 | 1975-01-29 | Rorer Inc William H | Phenylalkanoic acid derivatives |
BE776316R (fr) * | 1971-03-10 | 1972-06-06 | Rorer Inc William H | Nouveaux derives d'acides phenyl-acetiques substitues et procede pour leur |
-
1972
- 1972-08-17 DE DE2240441A patent/DE2240441A1/de active Pending
-
1973
- 1973-08-14 ES ES417884A patent/ES417884A1/es not_active Expired
- 1973-08-14 CH CH1170773A patent/CH588435A5/xx not_active IP Right Cessation
- 1973-08-14 ES ES417883A patent/ES417883A1/es not_active Expired
- 1973-08-14 AT AT710873A patent/AT323144B/de not_active IP Right Cessation
- 1973-08-14 AT AT711273A patent/AT328427B/de not_active IP Right Cessation
- 1973-08-14 AT AT710773A patent/AT323143B/de not_active IP Right Cessation
- 1973-08-15 SU SU1958291A patent/SU482039A3/ru active
- 1973-08-15 BG BG27671A patent/BG21844A3/xx unknown
- 1973-08-15 HU HUTO925A patent/HU166516B/hu unknown
- 1973-08-15 HU HUTO926A patent/HU166517B/hu unknown
- 1973-08-15 SU SU1958288A patent/SU484679A3/ru active
- 1973-08-15 SU SU1958290A patent/SU511846A3/ru active
- 1973-08-15 DD DD172907A patent/DD107901A5/xx unknown
- 1973-08-15 DD DD172906A patent/DD108071A5/xx unknown
- 1973-08-15 BG BG24328A patent/BG22069A3/xx not_active Expired
- 1973-08-15 BG BG24327A patent/BG21197A3/xx unknown
- 1973-08-16 IL IL43003A patent/IL43003A0/xx unknown
- 1973-08-16 NL NL7311300A patent/NL7311300A/xx unknown
- 1973-08-16 ZA ZA00735629A patent/ZA735629B/xx unknown
- 1973-08-16 CS CS5793A patent/CS165385B2/cs unknown
- 1973-08-16 ZA ZA00735628A patent/ZA735628B/xx unknown
- 1973-08-16 CS CS4903A patent/CS165386B2/cs unknown
- 1973-08-16 GB GB3884473A patent/GB1410852A/en not_active Expired
- 1973-08-16 GB GB3884373A patent/GB1411495A/en not_active Expired
- 1973-08-16 JP JP48092053A patent/JPS49124052A/ja active Pending
- 1973-08-16 CS CS4904A patent/CS165387B2/cs unknown
- 1973-08-16 PL PL1973164708A patent/PL90397B1/pl unknown
- 1973-08-16 ZA ZA00735616A patent/ZA735616B/xx unknown
- 1973-08-16 PL PL1973186474A patent/PL94510B1/pl unknown
- 1973-08-16 NL NL7311301A patent/NL7311301A/xx unknown
- 1973-08-16 AU AU59309/73A patent/AU476340B2/en not_active Expired
- 1973-08-16 IL IL43004A patent/IL43004A0/xx unknown
- 1973-08-16 JP JP48092052A patent/JPS49124051A/ja active Pending
- 1973-08-16 AU AU59308/73A patent/AU5930873A/en not_active Expired
- 1973-08-17 BE BE134690A patent/BE803733A/xx unknown
- 1973-08-17 BE BE134689A patent/BE803732A/xx unknown
- 1973-08-17 RO RO7300075821A patent/RO62917A/ro unknown
- 1973-08-17 RO RO7300075822A patent/RO62918A/ro unknown
- 1973-08-17 FR FR7330076A patent/FR2196168B1/fr not_active Expired
- 1973-08-17 BE BE134691A patent/BE803734A/xx unknown
- 1973-08-17 FR FR7330075A patent/FR2196167B1/fr not_active Expired
-
1974
- 1974-10-21 SU SU2069771A patent/SU520030A3/ru active
- 1974-10-21 SU SU2069774A patent/SU552021A3/ru active
- 1974-10-21 SU SU2069114A patent/SU538658A3/ru active
- 1974-10-21 SU SU2069577A patent/SU520907A3/ru active
- 1974-10-21 SU SU2069578A patent/SU511847A3/ru active
- 1974-10-21 SU SU2069576A patent/SU561505A3/ru active
- 1974-10-21 SU SU7402069575A patent/SU577967A3/ru active
- 1974-10-21 SU SU2069110A patent/SU554810A3/ru active
- 1974-11-30 ES ES432465A patent/ES432465A1/es not_active Expired
- 1974-11-30 ES ES432464A patent/ES432464A1/es not_active Expired
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE3212682C2 (pl) | ||
DE69305189T2 (de) | Arylcycloalkylderivate, deren Herstellung und Verwendung | |
DE1493955A1 (de) | Verfahren zur Herstellung substituierter Sulfonanilide | |
DE2205732A1 (de) | Neue 4-(4-biphenylyl)-butensaeurederivate | |
EP0185909B1 (de) | 5-Alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
DE2240440A1 (de) | Neue (4-biphenylyl)-alkohole und verfahren zu ihrer herstellung | |
EP0072960B1 (de) | 1,5-Diphenylpyrazolin-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
DE2112716A1 (de) | Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre Ester | |
DE2044172A1 (de) | Neue Pyrroldenvate, ein Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimittelzubereitungen | |
DE2633992C2 (pl) | ||
DE2240441A1 (de) | Neue biphenylderivate und verfahren zur herstellung | |
DE1949987A1 (de) | Neue alpha-Phenylfettsaeureverbindungen | |
DE2341507A1 (de) | Neue biphenylderivate und verfahren zur herstellung | |
DE1942521A1 (de) | Cyclopropancarbonsaeurederivate und Verfahren zu deren Herstellung | |
EP0000013B1 (de) | 4-Phenyl-8-amino-tetrahydroisochinoline, diese enthaltende pharmazeutische Präparate und Verfahren zur Herstellung dieser Präparate | |
DE69021525T2 (de) | Pyrrolaldehydderivate. | |
DE2747987C2 (pl) | ||
DE2112715A1 (de) | Neue 4-(4-Biphenylyl)-4-hydroxybuttersaeuren,ihre Salze,Ester und Lactone | |
DE2341506A1 (de) | Neue biphenylderivate und verfahren zu ihrer herstellung | |
DE69307210T2 (de) | Cycloalkylalkylamine als Liganden für sigma-Rezeptoren, Verfahren und ihre Herstellung und ihre Anwendung in der Therapie | |
DE2259243A1 (de) | 2'-fluorbiphenyle | |
DE2330838A1 (de) | Neue carbonsaeureester von 3-(4biphenylyl)-1-butanolen und 3-(4-biphenylyl)2-buten-1-olen | |
DE2421165A1 (de) | N-substituierte dihydroxyphenylaethylamine | |
DE68905259T2 (de) | Derivate von benzocyclohepten, verfahren zu ihrer herstellung und sie enthaltende arzneimittel. | |
DE2001288C3 (de) | Hydroxyalkyl-benzophenone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |