DE2112716A1 - Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre Ester - Google Patents
Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre EsterInfo
- Publication number
- DE2112716A1 DE2112716A1 DE19712112716 DE2112716A DE2112716A1 DE 2112716 A1 DE2112716 A1 DE 2112716A1 DE 19712112716 DE19712112716 DE 19712112716 DE 2112716 A DE2112716 A DE 2112716A DE 2112716 A1 DE2112716 A1 DE 2112716A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- acid
- biphenylyl
- oxo
- butyric 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
- 230000001741 anti-phlogistic effect Effects 0.000 title abstract 2
- LUKDALDUKVBQLO-UHFFFAOYSA-N 2-(2-phenylphenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=CC=C1C1=CC=CC=C1 LUKDALDUKVBQLO-UHFFFAOYSA-N 0.000 title 1
- 150000002148 esters Chemical class 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 9
- 239000004305 biphenyl Substances 0.000 claims abstract description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 239000002841 Lewis acid Substances 0.000 claims abstract description 5
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 4
- -1 ester halide Chemical class 0.000 claims description 85
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 65
- 239000002253 acid Substances 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 38
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminum chloride Substances Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 27
- YRTUFFFNUSJOBZ-UHFFFAOYSA-N 4-[4-(2-fluorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1F YRTUFFFNUSJOBZ-UHFFFAOYSA-N 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 23
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
- 238000009835 boiling Methods 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 15
- 229940014800 succinic anhydride Drugs 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000007530 organic bases Chemical class 0.000 claims description 10
- 150000007529 inorganic bases Chemical class 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical class C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 claims description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- 238000006317 isomerization reaction Methods 0.000 claims description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012954 diazonium Substances 0.000 claims description 5
- TYLDGEVEWDNUTE-ZHACJKMWSA-N (e)-4-hydroxy-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(\C=C\C(O)=O)O)=CC=C1C1=CC=CC=C1 TYLDGEVEWDNUTE-ZHACJKMWSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- CHUFTWGXFPSEFT-UHFFFAOYSA-N 4-[4-(2-nitrophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1[N+]([O-])=O CHUFTWGXFPSEFT-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229930188620 butyrolactone Natural products 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- KFQGOLUWWNZVAS-ZHACJKMWSA-N (e)-4-oxo-4-(4-phenylphenyl)but-2-enoic acid Chemical compound C1=CC(C(=O)/C=C/C(=O)O)=CC=C1C1=CC=CC=C1 KFQGOLUWWNZVAS-ZHACJKMWSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 3
- 150000002084 enol ethers Chemical class 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 238000006396 nitration reaction Methods 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- UYNNOZMIMGSGMY-UHFFFAOYSA-N 4-[4-(3-nitrophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC([N+]([O-])=O)=C1 UYNNOZMIMGSGMY-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 150000002641 lithium Chemical group 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
- NKEZJFRHKJVVKY-UHFFFAOYSA-N 4-oxo-4-(4-phenylphenyl)butanenitrile Chemical compound C1=CC(C(CCC#N)=O)=CC=C1C1=CC=CC=C1 NKEZJFRHKJVVKY-UHFFFAOYSA-N 0.000 claims 1
- OXNGKCPRVRBHPO-XLMUYGLTSA-N alpha-L-Fucp-(1->2)-beta-D-Galp-(1->3)-[alpha-L-Fucp-(1->4)]-beta-D-GlcpNAc Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@@H](O)[C@@H]2NC(C)=O)O[C@H]2[C@H]([C@H](O)[C@H](O)[C@H](C)O2)O)O[C@H](CO)[C@H](O)[C@@H]1O OXNGKCPRVRBHPO-XLMUYGLTSA-N 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- 150000001989 diazonium salts Chemical class 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 abstract description 2
- 150000002596 lactones Chemical class 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 53
- 238000002844 melting Methods 0.000 description 52
- 230000008018 melting Effects 0.000 description 52
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 150000003946 cyclohexylamines Chemical class 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
- 239000000155 melt Substances 0.000 description 27
- 238000003756 stirring Methods 0.000 description 27
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 18
- 150000007513 acids Chemical class 0.000 description 17
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 12
- 239000013543 active substance Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- NRVRUWYHAZNGIC-UHFFFAOYSA-N 4-[4-(2-chlorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1Cl NRVRUWYHAZNGIC-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000000829 suppository Substances 0.000 description 10
- 229920002261 Corn starch Polymers 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000008120 corn starch Substances 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 9
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 9
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 9
- 238000007127 saponification reaction Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000007868 Raney catalyst Substances 0.000 description 8
- 229910000564 Raney nickel Inorganic materials 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000003610 charcoal Substances 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000004074 biphenyls Chemical class 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- PHXPTRKAFIHKND-UHFFFAOYSA-N 4-[4-(2-acetamidophenyl)phenyl]-4-oxobutanoic acid Chemical compound CC(=O)NC1=CC=CC=C1C1=CC=C(C(=O)CCC(O)=O)C=C1 PHXPTRKAFIHKND-UHFFFAOYSA-N 0.000 description 5
- IYWPCNIEUKBHQZ-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=C(F)C=C1 IYWPCNIEUKBHQZ-UHFFFAOYSA-N 0.000 description 5
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 3
- RUYZJEIKQYLEGZ-UHFFFAOYSA-N 1-fluoro-4-phenylbenzene Chemical group C1=CC(F)=CC=C1C1=CC=CC=C1 RUYZJEIKQYLEGZ-UHFFFAOYSA-N 0.000 description 3
- JVHAJKHGPDDEEU-UHFFFAOYSA-N 2,4-difluoro-1-phenylbenzene Chemical group FC1=CC(F)=CC=C1C1=CC=CC=C1 JVHAJKHGPDDEEU-UHFFFAOYSA-N 0.000 description 3
- XCFZGTNKAXCMQO-UHFFFAOYSA-N 4-[4-(2,3-dichlorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC(Cl)=C1Cl XCFZGTNKAXCMQO-UHFFFAOYSA-N 0.000 description 3
- HIHPBJVJJOJTAU-UHFFFAOYSA-N 4-[4-(2,4-dichlorophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=C(Cl)C=C1Cl HIHPBJVJJOJTAU-UHFFFAOYSA-N 0.000 description 3
- WMROWOVBFKOJNB-UHFFFAOYSA-N 4-[4-(4-nitrophenyl)phenyl]-4-oxobutanoic acid Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=C([N+]([O-])=O)C=C1 WMROWOVBFKOJNB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
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- 150000001242 acetic acid derivatives Chemical class 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
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- WPRNXMAGDGWHNT-UHFFFAOYSA-N biphenylen-1-amine Chemical group C12=CC=CC=C2C2=C1C=CC=C2N WPRNXMAGDGWHNT-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 150000008363 butyronitriles Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 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
- 239000012141 concentrate Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GGSGSIKNDBMLGW-UHFFFAOYSA-N ethanol 2-methylpropan-1-amine Chemical compound C(C)O.NCC(C)C GGSGSIKNDBMLGW-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- BSRSADLNTFOSHR-UHFFFAOYSA-N ethyl 4-[4-(2-fluorophenyl)phenyl]-4-oxobutanoate Chemical compound C1=CC(C(=O)CCC(=O)OCC)=CC=C1C1=CC=CC=C1F BSRSADLNTFOSHR-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- CBADACBTCCDCBI-UHFFFAOYSA-N methyl 4-[4-(2-chlorophenyl)phenyl]-4-oxobutanoate Chemical compound C1=CC(C(=O)CCC(=O)OC)=CC=C1C1=CC=CC=C1Cl CBADACBTCCDCBI-UHFFFAOYSA-N 0.000 description 1
- SMESMAQQPPMENO-UHFFFAOYSA-N methyl 4-[4-(4-fluorophenyl)phenyl]-4-oxobutanoate Chemical compound C1=CC(C(=O)CCC(=O)OC)=CC=C1C1=CC=C(F)C=C1 SMESMAQQPPMENO-UHFFFAOYSA-N 0.000 description 1
- DLZVZNAPRCRXEG-UHFFFAOYSA-N methyl 4-oxobutanoate Chemical compound COC(=O)CCC=O DLZVZNAPRCRXEG-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical class OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene 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
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- 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
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
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)
Priority Applications (48)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112716 DE2112716A1 (de) | 1971-03-17 | 1971-03-17 | Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre Ester |
| CH1317075A CH572015A5 (cs) | 1971-03-17 | 1972-03-14 | |
| CH371672A CH573387A5 (cs) | 1971-03-17 | 1972-03-14 | |
| ES400791A ES400791A1 (es) | 1971-03-17 | 1972-03-15 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil)-4-oxobutiricos y sus esteres. |
| NL7203400A NL7203400A (cs) | 1971-03-17 | 1972-03-15 | |
| AT00693/73A AT319925B (de) | 1971-03-17 | 1972-03-16 | Vzh von neuen 4-(4-biphenylyl)-4-oxo-buttersaeuren,ihren salzen und ihren estern |
| AT00696/73A AT318594B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00694/73A AT318592B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| SE7203420A SE393102B (sv) | 1971-03-17 | 1972-03-16 | Forfarande for framstellning av nya 4-(4-bifenylyl)-4-oxo-smorsyror med farmakologiska egenskaper |
| BE780821A BE780821A (fr) | 1971-03-17 | 1972-03-16 | Nouveaux derives de l'acide 4-(4-biphenylyl) butyrique |
| IL38999A IL38999A (en) | 1971-03-17 | 1972-03-16 | 4-(4-biphenyl)-butyric acids and derivatives thereof and the preparation of such compounds |
| AT00683/73A AT320624B (de) | 1971-03-17 | 1972-03-16 | Vzh von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00686/73A AT318589B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00682/73A AT319923B (de) | 1971-03-17 | 1972-03-16 | Vzh von neuen 4-(4-biphenylyl)-4-oxo-buttersaeuren,ihren salzen und ihren estern |
| IE338/72A IE36174B1 (en) | 1971-03-17 | 1972-03-16 | 4-(4-biphenylyl)-butyric acid derivatives |
| DK124072A DK132944C (da) | 1971-03-17 | 1972-03-16 | Analogifremgangsmade til fremstilling af 4-(4-biphenylyl)-4-oxo-smorsyrer eller estere eller salte heraf |
| AT00681/73A AT320623B (de) | 1971-03-17 | 1972-03-16 | Vzh von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00691/73A AT318591B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| ZA721798A ZA721798B (en) | 1971-03-17 | 1972-03-16 | Improvements relating to 4-(4-biphenylyl)-butyric acid derivatives |
| AT00690/73A AT320625B (de) | 1971-03-17 | 1972-03-16 | Vzh von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00695/73A AT318593B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00688/73A AT319924B (de) | 1971-03-17 | 1972-03-16 | Vzh von neuen 4-(4-biphenylyl)-4-oxo-buttersaeuren,ihren salzen und ihren estern |
| AT00697/73A AT318595B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00684/73A AT318587B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00687/73A AT318590B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| GB1241672A GB1390091A (en) | 1971-03-17 | 1972-03-16 | 4-4-biphenylyl-butyric acid derivatives |
| AT00685/73A AT318588B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00689/73A AT317879B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT222272A AT311949B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur Herstellung von neuen 4-(4-Biphenylyl)-4-oxo-buttersäuren, ihren Salzen und ihren Estern |
| AT00692/73A AT317880B (de) | 1971-03-17 | 1972-03-16 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-oxobuttersaeuren,ihren salzen und ihren estern |
| AT00680/73A AT319922B (de) | 1971-03-17 | 1972-03-16 | Vzh von neuen 4-(4-biphenylyl)-4-oxo-buttersaeuren,ihren salzen und ihren estern |
| FR7209420A FR2130390A1 (cs) | 1971-03-17 | 1972-03-17 | |
| ES406528A ES406528A1 (es) | 1971-03-17 | 1972-09-05 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil)-4-oxobutiricos y sus esteres. |
| ES406537A ES406537A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406536A ES406536A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406532A ES406532A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406526A ES406526A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil)-4-oxobutiricos y sus esteres. |
| ES406533A ES406533A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406530A ES406530A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406534A ES406534A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil)-4-oxobutiricos y sus esteres. |
| ES406539A ES406539A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406529A ES406529A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil)-4-oxobutiricos y sus esteres. |
| ES406535A ES406535A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406531A ES406531A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| ES406538A ES406538A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil)-4-oxobutiricos y sus esteres. |
| ES406527A ES406527A1 (es) | 1971-03-17 | 1972-09-09 | Procedimiento para la preparacion de nuevos acidos 4-(4-bi-fenilil) - 4-oxobutiricos y sus esteres. |
| US05/406,196 US4021479A (en) | 1971-03-17 | 1973-10-15 | Derivatives of 4-(4-biphenylyl)-butyric acid |
| US05/543,266 US3997589A (en) | 1971-03-17 | 1975-01-23 | 4-(2'-Fluoro-4-biphenylylr-4-oxo-butyric acid and esters and salts thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712112716 DE2112716A1 (de) | 1971-03-17 | 1971-03-17 | Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre Ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2112716A1 true DE2112716A1 (de) | 1972-10-05 |
Family
ID=5801760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712112716 Pending DE2112716A1 (de) | 1971-03-17 | 1971-03-17 | Neue 4-(4-Biphenylyl)-4-oxobuttersaeuren,ihre Salze und ihre Ester |
Country Status (7)
| Country | Link |
|---|---|
| AT (19) | AT318588B (cs) |
| CH (2) | CH573387A5 (cs) |
| DE (1) | DE2112716A1 (cs) |
| DK (1) | DK132944C (cs) |
| ES (15) | ES400791A1 (cs) |
| SE (1) | SE393102B (cs) |
| ZA (1) | ZA721798B (cs) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534909A1 (fr) * | 1981-10-22 | 1984-04-27 | Roussel Uclaf | Nouveaux derives amines de l'acide 4-phenyl 4-oxo 2-butenoiques, leur preparation, leur application comme medicaments et les compositions les renfermant |
| EP0180290A1 (en) * | 1984-08-31 | 1986-05-07 | SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu | Omega-(2',4'-dihalobiphenylyl)oxo alkanoic acids and process for their preparation |
| WO1997043247A1 (en) * | 1996-05-15 | 1997-11-20 | Bayer Corporation | Inhibition of matrix metalloproteases by substituted phenethyl compounds |
| WO1997043245A1 (en) * | 1996-05-15 | 1997-11-20 | Bayer Corporation | Inhibition of matrix metalloproteases by acetylene containing compounds |
| US5968795A (en) * | 1996-05-15 | 1999-10-19 | Bayer Corporation | Biaryl acetylenes as inhibitors of matrix metalloproteases |
| WO2002042250A1 (fr) | 2000-11-27 | 2002-05-30 | Universite Louis Pasteur (Etablissement Public A Caractere Scientifique, Culturel Et Professionnel) | DERIVES DE L'ACIDE 4-HYDROXYBUTANOÏQUE ET DE SON HOMOLOGUE SUPERIEUR COMME LIGANDS DES RECEPTEURS DU η-HYDROXYBUTYRATE (GHB) COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET UTILISATIONS PHARMACEUTIQUES |
| US7091228B2 (en) | 2003-05-09 | 2006-08-15 | Bayer Pharmaceuticals Corporation | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| WO2008003299A1 (de) * | 2006-07-07 | 2008-01-10 | Christian-Albrechts-Universitaet Zu Kiel | Basische acetophenone als hemmstoffe von no-synthasen |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001049648A1 (en) * | 2000-01-04 | 2001-07-12 | Korea Research Institute Of Chemical Technology | Preparing method of 2-phenylalkanoic acid derivatives |
| CN115803026A (zh) * | 2020-06-26 | 2023-03-14 | 瓦伦塔有限责任公司 | 戊二酰亚胺衍生物用于治疗与异常白介素-6活性相关的疾病的用途 |
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1971
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- 1972-09-09 ES ES406531A patent/ES406531A1/es not_active Expired
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534909A1 (fr) * | 1981-10-22 | 1984-04-27 | Roussel Uclaf | Nouveaux derives amines de l'acide 4-phenyl 4-oxo 2-butenoiques, leur preparation, leur application comme medicaments et les compositions les renfermant |
| AT390254B (de) * | 1981-10-22 | 1990-04-10 | Roussel Uclaf | Verfahren zur herstellung von neuen aminderivaten der 4-phenyl-4-oxo-2-butensaeure und von deren salzen |
| EP0180290A1 (en) * | 1984-08-31 | 1986-05-07 | SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu | Omega-(2',4'-dihalobiphenylyl)oxo alkanoic acids and process for their preparation |
| WO1997043247A1 (en) * | 1996-05-15 | 1997-11-20 | Bayer Corporation | Inhibition of matrix metalloproteases by substituted phenethyl compounds |
| WO1997043245A1 (en) * | 1996-05-15 | 1997-11-20 | Bayer Corporation | Inhibition of matrix metalloproteases by acetylene containing compounds |
| US5968795A (en) * | 1996-05-15 | 1999-10-19 | Bayer Corporation | Biaryl acetylenes as inhibitors of matrix metalloproteases |
| WO2002042250A1 (fr) | 2000-11-27 | 2002-05-30 | Universite Louis Pasteur (Etablissement Public A Caractere Scientifique, Culturel Et Professionnel) | DERIVES DE L'ACIDE 4-HYDROXYBUTANOÏQUE ET DE SON HOMOLOGUE SUPERIEUR COMME LIGANDS DES RECEPTEURS DU η-HYDROXYBUTYRATE (GHB) COMPOSITIONS PHARMACEUTIQUES LES CONTENANT ET UTILISATIONS PHARMACEUTIQUES |
| FR2817256A1 (fr) * | 2000-11-27 | 2002-05-31 | Univ Pasteur | Derives de l'acides 4-hydroxybutanoique et de son homologue superieur comme ligands des recepteurs du gamma- hydroxybutyrate (ghb), compositions pharmaceutiques les contenant et utilisations pharmaceutiques |
| US7091228B2 (en) | 2003-05-09 | 2006-08-15 | Bayer Pharmaceuticals Corporation | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| US7423156B2 (en) | 2003-05-09 | 2008-09-09 | Bayer Pharmaceuticals Corporation | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| US7968576B2 (en) | 2003-05-09 | 2011-06-28 | Smith Roger A | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| US8013166B2 (en) | 2003-05-09 | 2011-09-06 | Bayer Healthcare Llc | Preparation and use of aryl alkyl acid derivatives for the treatment of obesity |
| WO2008003299A1 (de) * | 2006-07-07 | 2008-01-10 | Christian-Albrechts-Universitaet Zu Kiel | Basische acetophenone als hemmstoffe von no-synthasen |
| US7994365B2 (en) | 2006-07-07 | 2011-08-09 | Christian-Albrechts-Universitaet Zu Kiel | Basic acetophenones as inhibitors of NO-synthases |
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