GB1382267A - Phenylalkanoic acid derivatives - Google Patents

Phenylalkanoic acid derivatives

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Publication number
GB1382267A
GB1382267A GB5751071A GB5751071A GB1382267A GB 1382267 A GB1382267 A GB 1382267A GB 5751071 A GB5751071 A GB 5751071A GB 5751071 A GB5751071 A GB 5751071A GB 1382267 A GB1382267 A GB 1382267A
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GB
United Kingdom
Prior art keywords
group
phenyl
hydroxy
alkoxy
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.)
Expired
Application number
GB5751071A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
William H Rorer Inc
Original Assignee
William H Rorer Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US034870A external-priority patent/US3864384A/en
Priority claimed from US00152387A external-priority patent/US3852323A/en
Priority claimed from US00152451A external-priority patent/US3821267A/en
Priority claimed from US00152366A external-priority patent/US3821268A/en
Priority claimed from US195825A external-priority patent/US3867434A/en
Application filed by William H Rorer Inc filed Critical William H Rorer Inc
Publication of GB1382267A publication Critical patent/GB1382267A/en
Expired legal-status Critical Current

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Classifications

    • 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
    • C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/26—Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • 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
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/61—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/24—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/08—Sulfenic acids; Derivatives thereof
    • C07C313/18—Sulfenamides
    • C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C313/30—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/02—Thiosulfates
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/34—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

1382267 Phenylalkanoic acid derivatives WILLIAM H RORER Inc 10 Dec 1971 [10 March 1971 11 June 1971 (4) 21 July 1971 (2) 4 Nov 1971] 57510/71 Addition to 1355681 Heading C2C Novel phenylalkanoic acid derivatives of the general formula wherein R is a C 1-7 alkyl, C 3-7 cycloalkyl, C 3-7 cycloalkenyl, aryloxy, arylthio, arylamino, aroyl, heterocyclic, aryl or Y (not H)- substituted aryl group; Y is a hydrogen or halogen atom or a C 1-7 alkyl, nitro, amino, acylamino, mono- or di-C 1-7 alkylamino, mercapto, acylthio, C 1-7 alkylthio, C 1-7 alkylsulphinyl, C 1-7 alkylsulphonyl, hydroxy, C 1-6 alkoxy, C 1-7 acyloxy, C 1-7 haloalkyl, cyano or acetyl group, n is 0, 1 or 2, m is 0, 1 or 2, the sum of n and m is 0, 1 or 2, each of Rx, R# and Rγ is a hydrogen atom or C 1-7 alkyl group; X is a halogen atom or a hydroxy, C 1-6 alkoxy, C 1-7 acyloxy, C 2-7 carbalkoxy oxycarbamoyloxy, mono- or di-C 1-7 alkylcarbamoyloxy, C 1-7 alkanesulphonyloxy, benzenesulphonyloxy, toluenesulphonyloxy, carboxyacyloxy, mercapto, C 1-7 alkylthio, acylthio, sulpho, sulphino, C 1-7 alkylsulphinyl, C 1-7 alkylsulphonyl, thioacylthio, thiosulphato (of formula S 2 O 3 M where M is a cation), thiocyanato, amidinothio, carbamoylthio, mono- or di-C 1-7 alkylcarbamoylthio, C 1-6 alkoxy-thiocarbonylthio, C 1-6 alkoxy - carbonylthio, di-C 1-7 alkyl-thiocarbamoylthio, ar-C 1-5 -alkoxy-carbonylthio or carboxyacylthio group; and Z is a hydrogen atom or a hydroxy, C 1-6 alkoxy, ar-C 1-6 alkoxy, amino, mono- or di-C 1-7 alkylamino, C 3-7 cycloalkylamino, -NA (A is a C 2-6 alkylene group or a C 2-5 alkylene group having at least one atom selected from O, N and S in the chain), -NHOH, -NHNH 2 or -OM group, where M is an alkali or alkaline earth metal or Al atom or an ammonium or quaternary ammonium salt group; with the proviso that when n is 0 and m is 0, then X is a said oxy group and is other than a hydroxy, alkoxy or alkanoyloxy group; when n is 0 and m is 1 and Rx is an alkyl group and R is a cycloalkyl group, then X is other than a hydroxy group; and when n is 1 and m is 1 or n is 0 and m is 2 and Rx, R# and Rγ are hydrogen atoms, then X is other than a hydroxy group if R is a phenyl group, are prepared, e.g. (a) when X is a hydroxy group R# is a hydrogen ato m and Z is a hydroxy, alkoxy or aralkoxy group, by reduction of the corresponding compound in which -CXR 13 - is -CO-; (b) when X is a hydroxy group, R 13 is an alkyl group and Z is an alkoxy or aralkoxy group, by reaction of the corr esponding compound in which -CXR 13 - is -CO- with a Grignard reagent of the general formula R 13 Mghalogen; (c) when n is 0, m is 1, X is a hydroxy group, Rx is a hydrogen atom, and Z is an alkoxy or aralkoxy group, by reaction of the corresponding phenyl alkyl ketone with a haloalkanoic acid ester of the general formula halogen -CH 2 COOR<SP>11</SP> in the presence of zinc; (d) when each of X and Z is a hydroxy group, by acid hydrolysis of the corresponding nitrile; (e) by conversion of a Y substituent in the compound of the first general formula above into another such substituent by a known method; (f) when X is other than a hydroxy group, by conversion of a corresponding compound of the first general formula above to the desired compound having a different value of X by a known method; (g) by interconversion of acids, esters and amides of the first general formula above by known methods; (h) when Z is -OM, by salification of the corresponding free acid; and (i) by resolution of a racemic mixture of compounds of the first general formula above to give the optical isomers. The keto-ester starting materials of (a) above (in which n is 0) may be prepared by reaction of the corresponding benzene derivative with a suitable carboxylic acid chloride in the presence of AlC 3 . γ-(Y, R-Substituted phenyl)-α-hydroxybutyronitriles are prepared by reaction of an R,Y-substituted benzaldehyde with malonic acid or an alkyl derivative thereof, catalytic hydrogenation of the resulting cinnamic acid derivative, treatment of the resulting #-phenylpropionic acid with thionyl chloride, treatment of the resulting acid chloride with lithium tri-tbutoxyaluminium hydride and reaction of the resulting #-phenyl-propionaldehyde with sodium bisulphite and sodium cyanide. 4-(R,Y-substituted phenyl)-butan-2-ones are prepared by reaction of the corresponding #-phenyl-propionic acid chloride with methylmagnesium bromide in ether, followed by ammonium chloride solution. #-(R,Y-Substituted phenyl)-pyruvic acids are prepared (a) by bromination of the corresponding #-phenyl-cinnamic acid and treatment of the resulting α,#-dibromo-#-phenyl-propionic acid with piperidine, followed by acid hydrolysis, and (b) by reaction of the corresponding benzaldehyde with hippuric acid in the presence of sodium acetate and acetic anhydride and base hydrolysis of the resulting 2-phenyl-4-benzylidenyl-5-oxazolone, and may be esterified to give the corresponding alkyl esters. #-(R,Y-Substituted phenyl)-cinnamic acids are prepared by dehydration of the corresponding alkyl #-phenyl #-hydroxy-propionate with phosphorus oxychloride. #-Hydroxy-γ-(R,Y-substituted phenyl) - butyronitriles are prepared by reaction of an R,Y-substituted phenyl magnesium bromide with epichlorohydrin and reaction of the resulting 1 -chloro-3-(R,Y-substituted phenyl)-2- propanol with aqueous sodium cyanide. (RSubstituted bromo-, chloro- or nitro-phenyl) - glyoxylates are prepared-by bromination, chlorination or nitration, respectively, of the corresponding (R-substituted phenyl)-glyoxylate. Pharmaceutical compositions having analgesic, antipyretic and anti-inflammatory activity comprise, as active ingredient, a phenylalkanoio acid derivative of the first general formula above, together with an acceptable carrier therefor, and may be administered orally, topically, parenterally or rectally.
GB5751071A 1970-05-05 1971-12-10 Phenylalkanoic acid derivatives Expired GB1382267A (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US034870A US3864384A (en) 1970-05-05 1970-05-05 Substituted phenylacetic acid compounds
US12299871A 1971-03-10 1971-03-10
US15236871A 1971-06-11 1971-06-11
US00152387A US3852323A (en) 1970-05-05 1971-06-11 Phenylacetic acids
US00152451A US3821267A (en) 1970-05-05 1971-06-11 A-acylthio-p-cyclohexylphenylacetic acid and derivatives
US00152366A US3821268A (en) 1970-05-05 1971-06-11 Alpha-acylthio biphenylylacetic acids
US16492071A 1971-07-21 1971-07-21
US16482271A 1971-07-21 1971-07-21
US195825A US3867434A (en) 1971-11-04 1971-11-04 Phenyl butyric acids and derivatives thereof

Publications (1)

Publication Number Publication Date
GB1382267A true GB1382267A (en) 1975-01-29

Family

ID=27578118

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5751071A Expired GB1382267A (en) 1970-05-05 1971-12-10 Phenylalkanoic acid derivatives

Country Status (3)

Country Link
DE (1) DE2162038A1 (en)
FR (4) FR2128277B2 (en)
GB (1) GB1382267A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0164590A1 (en) * 1981-06-03 1985-12-18 Ciba-Geigy Ag Derivatives of 4-(3'-trifluoromethylphenoxy)-benzoylacetic acid
WO1987000521A3 (en) * 1985-07-16 1987-03-12 Boehringer Mannheim Gmbh New carboxylic acid derivatives, their manufacturing process, use and medicines containing these compounds
EP0279162A1 (en) * 1987-01-13 1988-08-24 Roche Diagnostics GmbH Carbonic acid derivatives, process for their preparation and pharmaceuticals containing them
CN114105762A (en) * 2020-09-01 2022-03-01 宁夏金海沃德科技有限公司 Resource recovery device and treatment method for acidic wastewater

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2240441A1 (en) * 1972-08-17 1974-02-28 Thomae Gmbh Dr K NEW BIPHENYL DERIVATIVES AND METHOD OF MANUFACTURING

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3027406A (en) * 1960-01-18 1962-03-27 Merck & Co Inc 3-hydroxy-3-biphenylylheptanoic acid
CH420102A (en) * 1960-05-25 1966-09-15 Merck & Co Inc Process for the preparation of aryl-substituted α-oxy-aliphatic carboxylic acids
GB1040735A (en) * 1964-07-23 1966-09-01 British Drug Houses Ltd 4-aryl-3-hydroxybutyric acid and esters, amides and salts thereof
GB1171670A (en) * 1967-11-15 1969-11-26 Bdh Chemicals Ltd Derivatives of 4-Aryl-3-Hydroxybutyric Acid
FR2043467A1 (en) * 1969-05-12 1971-02-19 Clin Byla Ets

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0164590A1 (en) * 1981-06-03 1985-12-18 Ciba-Geigy Ag Derivatives of 4-(3'-trifluoromethylphenoxy)-benzoylacetic acid
WO1987000521A3 (en) * 1985-07-16 1987-03-12 Boehringer Mannheim Gmbh New carboxylic acid derivatives, their manufacturing process, use and medicines containing these compounds
US4933367A (en) * 1985-07-16 1990-06-12 Boehringer Mannheim Gmbh Carboxylic acid derivatives, processes for the preparation thereof, the use thereof, and pharmaceutical compositions which contain these compounds
EP0279162A1 (en) * 1987-01-13 1988-08-24 Roche Diagnostics GmbH Carbonic acid derivatives, process for their preparation and pharmaceuticals containing them
US5145611A (en) * 1987-01-13 1992-09-08 Boehringer Mannheim Gmbh Carboxylic acid derivatives, and pharmaceutical compositions containing them
CN114105762A (en) * 2020-09-01 2022-03-01 宁夏金海沃德科技有限公司 Resource recovery device and treatment method for acidic wastewater

Also Published As

Publication number Publication date
DE2162038A1 (en) 1972-08-17
FR2128277B2 (en) 1979-06-22
FR2282867A2 (en) 1976-03-26
FR2279386A2 (en) 1976-02-20
FR2128277A2 (en) 1972-10-20
FR2282867B2 (en) 1979-08-17
FR2279387A2 (en) 1976-02-20

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