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GB1434090A - Halo-4-biphenylyl-butyric acid esters and amides and pharma ceutical compositions containing them - Google Patents

Halo-4-biphenylyl-butyric acid esters and amides and pharma ceutical compositions containing them

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Publication number
GB1434090A
GB1434090A GB3884273A GB3884273A GB1434090A GB 1434090 A GB1434090 A GB 1434090A GB 3884273 A GB3884273 A GB 3884273A GB 3884273 A GB3884273 A GB 3884273A GB 1434090 A GB1434090 A GB 1434090A
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Prior art keywords
formula
compounds
compound
reacting
alkoxy
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
GB3884273A
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
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 DE2240441A external-priority patent/DE2240441A1/en
Priority claimed from DE19722261912 external-priority patent/DE2261912A1/en
Priority claimed from DE19732300402 external-priority patent/DE2300402A1/en
Priority claimed from DE19732309914 external-priority patent/DE2309914A1/en
Priority claimed from DE19732322195 external-priority patent/DE2322195A1/en
Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Priority to BR668474A priority Critical patent/BR7406684D0/en
Publication of GB1434090A publication Critical patent/GB1434090A/en
Expired legal-status Critical Current

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    • 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
    • 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
    • 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
    • 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
    • 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

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  • Chemical & Material Sciences (AREA)
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  • Medicinal Chemistry (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biochemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
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  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

1434090 Halo-4-biphenylyl-butyric acids, esters and amides DR KARL THOMAE GmbH 16 Aug 1973 [17 Aug 1972 18 Dec 1972 5 Jan 1973 28 Feb 1973 3 May 1973] 38842/73 Headings C2C and C2P The invention comprises compounds of the formula wherein R 1 is halogen and B is OH, alkoxy, aralkoxy or wherein R 3 and R 4 are H, carboxymethyl, C 1 - C 3 alkyl or phenyl optionally substituted by OH or CH 3 and when B is OH, acid addition salts thereof. They may be obtained by any of the following processes:-(1) when B is OH, by reacting compounds of the formula wherein X is OH, halogen or an acyloxy group, with a 1,1-dihaloethylene in acid and subsequently hydrolysing the intermediate with water; (2) by reduction of compounds of the formula wherein A is (3) when B is OH or alkoxy, by reduction of compounds of Formula III above wherein A is (4) when B is OH, by reacting a compound of the formula wherein Hal is a halogen atom with an alkali metal salt or an alkoxy magnesium salt of a malonate and saponifying the malonate obtained of the formula wherein R 5 is a C 1 -C 3 alkyl group, to a free acid which is subsequently decarboxylated; (5) when B is OH, by saponifying a nitrile of the formula by saponifying and decarboxylating a nitrile of the formula or by reduction and simultaneous saponification and decarboxylation of a nitrile of the formula (6) when B is OH, by oxidation of a carbinol of the formula (7) when B is OH, by reacting a Grignard compound of the formula wherein Hal is a halogen atom, with CO 2 ; (8) when B is OH or alkoxy, by solvolysis of compounds of the formula (9) when B is tertiary alkoxy, by reaction of a compound of Formula IIa with a metalated tert-alkyl acetate of the formula wherein Me is Li or Na and tert.alkyl is a C 4 - C 10 tertiary alkyl group; (10) when B is OH, by hydrolysis of ketene thioacetals of the formula wherein R 8 and R 9 are C 1 -C 3 alkyl groups or together they form a 5-7 membered ring which can optionally be interrupted by a further S atom; (11) when B is alkoxy, by desulphurizing a compound of the formula wherein R 6 is an alkyl group; (12) by decomposing a diazoketone of the formula with water to give a free acid, with an alcohol to give an ester, or with a primary or secondary amine of the formula to give an amide; (13) when B is OH, alkoxy or aralkoxy, by reacting a compound of Formula IIa with an alkali metal salt of an alkyl or aralkyl acetoacetate to form a compound of the formula wherein R, is alkyl or aryl, and cleaving this compound with a strong base; (14) when B is OH, alkoxy or aralkoxy by warming a compound of the formula wherein R 7 is alkyl or aralkyl, with a strong base whereby on acidification an acid of Formula I is produced, or with water whereby a compound of Formula I wherein B is alkoxy or aralkoxy is produced; (15) when B is OH, by oxidation of an aldehyde of the formula Pharmaceutical compositions comprise compounds of Formula I above. They have antiphlogistic activity and may be administered orally, parenterally or rectally. Compounds of Formula II above wherein X is OH may be obtained by reduction of the corresponding ketone. Compounds of Formula II above wherein X is halogen or acyloxy may be obtained by treatment of the corresponding compounds wherein X is OH with hydrohalic acids, phosphorus halides or thionyl halide or by acylation. Compounds of Formula III above wherein A is may be obtained by reacting -a ketone of the formula with a Zn compound of a corresponding halogenoacetate to give a compound of Formula III wherein A is followed by dehydration to give the required products. Compounds of Formula Va may be obtained by reduction of compounds of Formula Vd which may themselves be obtained by reacting a ketone of Formula XVIII with cyanoacetic acid or a derivative of the formula wherein Q is CN, CONH 2 or COOH optionally esterified with an aliphatic or araliphatic alcohol or a phenol. Compounds of Formula V may be obtained by decarboxylation of compounds of Formula Va. Compounds of Formula VI may be obtained by conversions of a compound of formula wherein Hal is halogen, to a Grignard compound followed by reaction with paraformaldehyde. Compounds of Formula XX may be obtained by reacting an appropriately substituted biphenyl with oxalic acid monoethyl ester chloride and anhydrous AlCl 3 to obtain the corresponding 2-(4-biphenyl)-glyoxylic acid ester which on reaction with CH 3 MgBr gives the 2-(4- biphenyl)-2-hydroxy-propionic acid which may then be treated with HI in acetic acid to give the 2-(4-biphenylyl)-propionic acid and reduced with LiAlH 4 in ether to give a propanol of the formula which on treatment with a phosphorus trihalide gives a compound of Formula XX. Compounds of Formula XXI may also be obtained by reduction with NaBH 4 of a compound of formula which may itself be obtained by heating in an alcoholic caustic alkali solution a compound of the formula which may itself be obtained by the reaction of 41-phenylacetophenones with chloroacetoacetates in the presence of NaNH 2 in benzene. Compounds of Formula VIII may be obtained by reacting halides of Formula II wherein X is halogen with metalated heterocycles of the formula Compounds of Formula X may be obtained by reaction of an aldehyde of Formula XXII with a lithium thioacetal of the formula to give compounds of the formula which may be dehydrated to give compounds of Formula X. Compounds of Formula XII may be obtained by alkylation of a compound of the formula wherein R 7 is an alkyl group, with a halogen compound of Formula II (X=halogen) in the presence of a metalating agent. Diazoketones of Formula XIII may be obtained by treating with diazonethane an acyl halide of the formula wherein Hal is Cl, Br or I. Compounds of Formula XVI may be obtained by reacting a compound of Formula IIa with a compound of the formula wherein R 7 is an alkyl or aralkyl group. Compounds of Formula XXXII may be obtained by reduction of a nitrile of Formula V.
GB3884273A 1972-08-17 1973-08-16 Halo-4-biphenylyl-butyric acid esters and amides and pharma ceutical compositions containing them Expired GB1434090A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BR668474A BR7406684D0 (en) 1973-08-16 1974-08-14 PO CONTAINING ABOUT 0.2 TO ABOUT 5.4% BY CARBON WEIGHT METALLIC SUBSTRATE ARTICLE TROCOID SURFACE AND CHROME COMPOSITE ARTICLE

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE2240441A DE2240441A1 (en) 1972-08-17 1972-08-17 NEW BIPHENYL DERIVATIVES AND METHOD OF MANUFACTURING
DE19722261912 DE2261912A1 (en) 1972-12-18 1972-12-18 Antiphlogistic butyric acid derivs - 3-(halo-substd.-4-biphenylyl)-butyric acid derivs
DE19732300402 DE2300402A1 (en) 1973-01-05 1973-01-05 Antiphlogistic butyric acid derivs - 3-(halo-substd.-4-biphenylyl)-butyric acid derivs
DE19732309914 DE2309914A1 (en) 1973-02-28 1973-02-28 NEW PROCESS FOR THE PRODUCTION OF 3- (4-BIPHENYLYL) BUTTER ACIDS
DE19732322195 DE2322195A1 (en) 1973-05-03 1973-05-03 Antiphlogistic butyric acid derivs - 3-(halo-substd.-4-biphenylyl)-butyric acid derivs

Publications (1)

Publication Number Publication Date
GB1434090A true GB1434090A (en) 1976-04-28

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GB3884273A Expired GB1434090A (en) 1972-08-17 1973-08-16 Halo-4-biphenylyl-butyric acid esters and amides and pharma ceutical compositions containing them

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JP (1) JPS5525173B2 (en)
AT (1) ATA785173A (en)
AU (1) AU476339B2 (en)
BG (3) BG21846A3 (en)
DD (2) DD111204A5 (en)
FR (1) FR2196171B1 (en)
GB (1) GB1434090A (en)
HU (1) HU168129B (en)
IL (1) IL43002A0 (en)
NL (1) NL7311355A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007009389A3 (en) * 2005-07-22 2007-04-19 Shanghai Inst Materia Medica Substituted propanamide derivatives, preparation and use thereof
CN105061183A (en) * 2015-08-18 2015-11-18 太仓运通生物化工有限公司 Method for preparing 1-cyclohexenylacetic acid

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5957870U (en) * 1982-10-08 1984-04-16 株式会社フジクラ Connections for wiring boards
JP2579766B2 (en) * 1986-05-07 1997-02-12 住友化学工業株式会社 Optically active biphenyl derivative and method for producing the same
US11844278B2 (en) * 2019-01-23 2023-12-12 Lg Innotek Co., Ltd. Thermoelectric element
JP7345777B2 (en) * 2019-06-11 2023-09-19 国立大学法人千葉大学 Method for producing ketone compounds, method for producing carboxylic acid derivatives

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3385887A (en) * 1961-02-02 1968-05-28 Boots Pure Drug Co Ltd 4-isobutylphenylacetic acid
GB1091403A (en) * 1964-01-24 1967-11-15 Boots Pure Drug Co Ltd Therapeutically active phenylalkane derivatives
FR1545270A (en) * 1966-11-25 1968-11-08 Boots Pure Drug Co Ltd Process for the preparation of phenylalkanoic acids
NL7203400A (en) * 1971-03-17 1972-09-19
GB1382996A (en) * 1971-03-26 1975-02-05 Boots Co Ltd Substituted biphenyls
BE787782A (en) * 1971-08-20 1973-02-19 Thomae Gmbh Dr K NEW 4- (4-BIPHENYLYL) -BUTYRAMIDES
GB1400448A (en) * 1971-08-25 1975-07-16 Boots Co Ltd Oxazoline derivatives arylalkanoic acids their preparation and therapeutic compositions containing them

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007009389A3 (en) * 2005-07-22 2007-04-19 Shanghai Inst Materia Medica Substituted propanamide derivatives, preparation and use thereof
CN105061183A (en) * 2015-08-18 2015-11-18 太仓运通生物化工有限公司 Method for preparing 1-cyclohexenylacetic acid

Also Published As

Publication number Publication date
ATA785173A (en) 1975-01-15
NL7311355A (en) 1974-02-19
BG21010A3 (en) 1976-01-20
AU476339B2 (en) 1976-09-16
JPS5525173B2 (en) 1980-07-04
DD111204A5 (en) 1975-02-05
BG21847A3 (en) 1976-09-20
AU5930773A (en) 1975-02-20
FR2196171A1 (en) 1974-03-15
IL43002A0 (en) 1973-11-28
DD107900A5 (en) 1974-08-20
BG21846A3 (en) 1976-09-20
FR2196171B1 (en) 1978-06-30
HU168129B (en) 1976-02-28
JPS4980046A (en) 1974-08-02

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Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees