DE2261912A1 - Neues verfahren zur herstellung von 3-(4-biphenylyl)-buttersaeuren - Google Patents
Neues verfahren zur herstellung von 3-(4-biphenylyl)-buttersaeurenInfo
- Publication number
- DE2261912A1 DE2261912A1 DE19722261912 DE2261912A DE2261912A1 DE 2261912 A1 DE2261912 A1 DE 2261912A1 DE 19722261912 DE19722261912 DE 19722261912 DE 2261912 A DE2261912 A DE 2261912A DE 2261912 A1 DE2261912 A1 DE 2261912A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- malonic acid
- biphenylyl
- acid ester
- 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
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 title description 4
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 230000001741 anti-phlogistic effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 25
- -1 alkali metal salt Chemical class 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- YPLFUSQRFMNDIK-UHFFFAOYSA-N 3-(4-phenylphenyl)butanoic acid Chemical class C1=CC(C(CC(O)=O)C)=CC=C1C1=CC=CC=C1 YPLFUSQRFMNDIK-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- WIDJUGXQJWBBGH-UHFFFAOYSA-N 1-(1-chloroethyl)-4-(2-fluorophenyl)benzene Chemical compound C1=CC(C(Cl)C)=CC=C1C1=CC=CC=C1F WIDJUGXQJWBBGH-UHFFFAOYSA-N 0.000 description 5
- 150000001447 alkali salts Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- JJILKXZHMWBFAB-UHFFFAOYSA-N 2-[1-[4-(2-chlorophenyl)phenyl]ethyl]propanedioic acid Chemical compound C1=CC(C(C(C(O)=O)C(O)=O)C)=CC=C1C1=CC=CC=C1Cl JJILKXZHMWBFAB-UHFFFAOYSA-N 0.000 description 4
- UONMCIWZZVLMQJ-UHFFFAOYSA-N 2-[1-[4-(2-fluorophenyl)phenyl]ethyl]propanedioic acid Chemical compound C1=CC(C(C(C(O)=O)C(O)=O)C)=CC=C1C1=CC=CC=C1F UONMCIWZZVLMQJ-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 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
- 239000003513 alkali Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HORIKVLWDGXBNZ-UHFFFAOYSA-N 1-(1-bromoethyl)-4-(4-fluorophenyl)benzene Chemical compound C1=CC(C(Br)C)=CC=C1C1=CC=C(F)C=C1 HORIKVLWDGXBNZ-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- WJURYJKKHZBZMO-UHFFFAOYSA-N 2-[1-[4-(4-fluorophenyl)phenyl]ethyl]propanedioic acid Chemical compound C1=CC(C(C(C(O)=O)C(O)=O)C)=CC=C1C1=CC=C(F)C=C1 WJURYJKKHZBZMO-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FMYFYLKYHXEHQM-UHFFFAOYSA-N 1-(1-bromoethyl)-4-(2-fluorophenyl)benzene Chemical compound C1=CC(C(Br)C)=CC=C1C1=CC=CC=C1F FMYFYLKYHXEHQM-UHFFFAOYSA-N 0.000 description 1
- TXGWVUKEBDNEBM-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CC=CC=C1F TXGWVUKEBDNEBM-UHFFFAOYSA-N 0.000 description 1
- SNROWBDCKYEFHP-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1C1=CC=C(F)C=C1 SNROWBDCKYEFHP-UHFFFAOYSA-N 0.000 description 1
- QJCZAGAGPGJJBF-UHFFFAOYSA-N 1-chloro-2-[4-(1-chloroethyl)phenyl]benzene Chemical compound C1=CC(C(Cl)C)=CC=C1C1=CC=CC=C1Cl QJCZAGAGPGJJBF-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
- YNXOWAGEHLRWAE-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)phenyl]butanoic acid Chemical compound C1=CC(C(CC(O)=O)C)=CC=C1C1=CC=C(F)C=C1 YNXOWAGEHLRWAE-UHFFFAOYSA-N 0.000 description 1
- ZFAGXQVYYWOLNK-UHFFFAOYSA-N CCO[Mg] Chemical class CCO[Mg] ZFAGXQVYYWOLNK-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- ZRDZXPSXXZMRTD-UHFFFAOYSA-N diethyl 2-[1-[4-(2-fluorophenyl)phenyl]ethyl]propanedioate Chemical compound C1=CC(C(C)C(C(=O)OCC)C(=O)OCC)=CC=C1C1=CC=CC=C1F ZRDZXPSXXZMRTD-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical class O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT785173A ATA785173A (de) | 1972-08-17 | 1972-09-13 | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-hydroxy-buttersaeureamiden |
| DE19722261912 DE2261912A1 (de) | 1972-12-18 | 1972-12-18 | Neues verfahren zur herstellung von 3-(4-biphenylyl)-buttersaeuren |
| ES417792A ES417792A1 (es) | 1972-08-17 | 1973-08-11 | Procedimiento para la preparacion de nuevos derivados de bifenilo. |
| DD172904A DD107900A5 (enExample) | 1972-08-17 | 1973-08-15 | |
| BG027680A BG21847A3 (bg) | 1972-08-17 | 1973-08-15 | Метод за получаване на бифенилови производни |
| BG027679A BG21846A3 (bg) | 1972-08-17 | 1973-08-15 | Метод за получаване на бифенилови производни |
| HUTO924A HU168129B (enExample) | 1972-08-17 | 1973-08-15 | |
| BG024326A BG21010A3 (bg) | 1972-08-17 | 1973-08-15 | Метод за получаване на бифенилови производни |
| DD177432*A DD111204A5 (enExample) | 1972-08-17 | 1973-08-15 | |
| BG2768473A BG21390A3 (enExample) | 1972-12-18 | 1973-08-15 | |
| GB3884273A GB1434090A (en) | 1972-08-17 | 1973-08-16 | Halo-4-biphenylyl-butyric acid esters and amides and pharma ceutical compositions containing them |
| AU59307/73A AU476339B2 (en) | 1972-08-17 | 1973-08-16 | Halo-4-biphenylyl-butyric acids, esters and amides and pharmaceutical compositions containing them |
| JP9205173A JPS5525173B2 (enExample) | 1972-08-17 | 1973-08-16 | |
| CS4905A CS165388B2 (enExample) | 1972-12-18 | 1973-08-16 | |
| CS491774A CS165400B2 (enExample) | 1972-12-18 | 1973-08-16 | |
| IL43002A IL43002A0 (en) | 1972-08-17 | 1973-08-16 | Novel biphenylyl derivatives,their preparation and pharmaceutical compositions containing them |
| FR7330079A FR2196171B1 (enExample) | 1972-08-17 | 1973-08-17 | |
| NL7311355A NL7311355A (enExample) | 1972-08-17 | 1973-08-17 | |
| AT837174A AT332382B (de) | 1972-12-18 | 1974-10-18 | Verfahren zur herstellung neuer (1-(4-biphenylyl)-1-athyl)-malonsauren und deren estern |
| AT837474A AT332867B (de) | 1972-12-18 | 1974-10-18 | Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, deren estern, amiden und salzen |
| SU2069737A SU520908A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилилмасл ной кислоты или ее эфира или ее соли |
| SU2069772A SU517245A3 (ru) | 1972-08-17 | 1974-10-21 | Способ получени замещенной бифенилмасл ной кислоты или ее соли |
| ES432466A ES432466A1 (es) | 1972-12-18 | 1974-11-30 | Procedimiento para la preparacion de nuevos derivados de bifenilo. |
| ES432478A ES432478A1 (es) | 1972-12-18 | 1974-11-30 | Procedimiento para la preparacion de acidos malonicos, es- teres de acidos malonicos y esteres de acidos beta-cetocar- boxilicos. |
| US05/577,170 US3987197A (en) | 1972-08-17 | 1975-05-14 | 3-(2'-fluoro-4-biphenylyl)-butyric acid and salts thereof |
| FR7520342A FR2275439A1 (fr) | 1972-12-18 | 1975-06-27 | Nouveaux derives de biphenyle et procedes pour les fabriquer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722261912 DE2261912A1 (de) | 1972-12-18 | 1972-12-18 | Neues verfahren zur herstellung von 3-(4-biphenylyl)-buttersaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2261912A1 true DE2261912A1 (de) | 1974-06-20 |
Family
ID=5864729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722261912 Pending DE2261912A1 (de) | 1972-08-17 | 1972-12-18 | Neues verfahren zur herstellung von 3-(4-biphenylyl)-buttersaeuren |
Country Status (3)
| Country | Link |
|---|---|
| CS (1) | CS165388B2 (enExample) |
| DE (1) | DE2261912A1 (enExample) |
| ES (1) | ES432466A1 (enExample) |
-
1972
- 1972-12-18 DE DE19722261912 patent/DE2261912A1/de active Pending
-
1973
- 1973-08-16 CS CS4905A patent/CS165388B2/cs unknown
-
1974
- 1974-11-30 ES ES432466A patent/ES432466A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS165388B2 (enExample) | 1975-12-22 |
| ES432466A1 (es) | 1976-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH354435A (de) | Verfahren zur Herstellung ungesättigter Carbonsäuren | |
| EP0124041B1 (de) | Verfahren zur Herstellung von Cyclohexandionderivaten | |
| DE102004005318A1 (de) | Verfahren zur Herstellung von 2,5-Dimethylphenylessigsäure | |
| DE3122995C2 (enExample) | ||
| DE2261912A1 (de) | Neues verfahren zur herstellung von 3-(4-biphenylyl)-buttersaeuren | |
| DE1104965B (de) | Verfahren zur Herstellung von Derivaten des Urazols | |
| DE2533396C2 (de) | 3-Methyl-3-aryl-brenztraubensäureester und Verfahren zu ihrer Herstellung | |
| DE1793825C3 (de) | 2-(6'-substituierte-2'-Naphthyl)propionsäurederivate und deren Herstellung | |
| DE886900C (de) | Verfahren zur Herstellung von neuen Naphthalinderivaten | |
| EP0378073B1 (de) | Verfahren zur Herstellung von 1,3-Cyclopentandion | |
| DE818937C (de) | Verfahren zur Synthese von Oestron und seinen Abbauprodukten sowie ihren Derivaten und Isomeren | |
| DE837099C (de) | Verfahren zur Herstellung von Aminodiolen | |
| CH250806A (de) | Verfahren zur Herstellung eines neuen Oxyhydrophenanthren-Derivates. | |
| AT332867B (de) | Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, deren estern, amiden und salzen | |
| DE2208568C3 (de) | Verfahren zur Herstellung von a-Ketocarbonsäuren und a- Ketocarbonsäureamide als dafür geeignete Zwischenprodukte | |
| DE141699C (enExample) | ||
| DE570861C (de) | Verfahren zur Darstellung von 1-m-Oxyphenyl-2-aminopropan-1-ol | |
| DE915938C (de) | Verfahren zur Herstellung von Oxoacylaminen der Cyclopentanopolyhydrophenanthrenreihe | |
| AT222116B (de) | Verfahren zur Herstellung von neuen, 4-substituierten 1,2-Diaryl-3,5-dioxo-pyrazolidinen | |
| AT334887B (de) | Schaltungsanordnung für die zündung und den betrieb von gasentladungslampen | |
| DE1568936C3 (de) | Verfahren zur Herstellung von Benzylmalonsäure | |
| DE2912052A1 (de) | Verfahren zur herstellung von 2eckige klammer auf 4-(thienylcarbonyl)phenyl eckige klammer zu -propionsaeure | |
| DE1091115B (de) | Verfahren zur Herstellung von 3-Formylmethyl-4-methyl-8-alkoxy-1, 2, 3, 4-tetrahydronphthalin-1-onen | |
| DE893647C (de) | Verfahren zur Herstellung von 1-Methyl-2-(ª‰-halogenaethyl)-4-kohlenwasserstoffoxycyclohexen-1 | |
| DE842051C (de) | Verfahren zur Herstellung von Hydrofluoren-2-carbonsaeuren und ihren Derivaten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |