GB1272155A - Orthohydroxybiphenylenecarboxylic acids and their derivatives - Google Patents

Orthohydroxybiphenylenecarboxylic acids and their derivatives

Info

Publication number
GB1272155A
GB1272155A GB29540/70A GB2954070A GB1272155A GB 1272155 A GB1272155 A GB 1272155A GB 29540/70 A GB29540/70 A GB 29540/70A GB 2954070 A GB2954070 A GB 2954070A GB 1272155 A GB1272155 A GB 1272155A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
methoxy
acetyloxy
carboxy
acetyl
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
GB29540/70A
Inventor
Tsung-Ying Shen
Gordon Lyn Walford
Bruce Edward Witzel
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.)
Merck and Co Inc
Original Assignee
Merck and Co 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
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1272155A publication Critical patent/GB1272155A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
    • C07C65/36—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic containing rings other than six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/17—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • C07C65/26—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic containing rings other than six-membered aromatic rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Emergency Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,272,155. o-Hydroxybiphenylene carboxylic acids and derivatives. MERCK & CO. Inc. 18 June, 1970 [25 June, 1969; 20 April, 1970], No. 29540/70. Heading C2C. Novel compounds of Formula I in which R is a hydroxy, amino, alkoxy, alkylamino, dialkylamino, dialkylaminoalkyl, dialkylaminoalkoxy, hydroxyalkoxy, polyhydroxyalkoxy, alkoxyalkoxy, phenylalkoxy, phenoxy, alkoxyphenoxy, dialkylaminophenoxy, alkanoylaminophenoxy, carboxyphenoxy, alkoxycarbonylphenoxy, hydrazino, morpholino, piperidino, pyrrolidino, or hydroxyalkylamino radical; R 2 is a hydrogen atom or an acyl, alkyl or alkoxycarbonyl radical; R 3 is a hydrogen or halogen atom or a haloalkyl, alkyl, C 3-7 cycloalkyl, or alkoxy radical; and each of X 1 , X 2 , X 3 and X 4 , which may be the same as or different from the others, is a hydrogen or halogen atom or an alkyl, hydroxy, alkoxy, acyloxy, haloalkyl, nitro, amino, alkylamino, dialkylamino, acylamino, mercapto, alkylthio, alkylsulphinyl, alkylsulphonyl, sulphamoyl, aminoalkyl, alkylaminoalkyl, hydroxyalkyl, alkoxyalkyl, mercaptoalkyl, alkylthioalkyl, cyano, carboxy, alkoxycarbonyl, carbamoyl, aryl, alkaryl, aralkyl, aryloxy, aralkoxy or salicyl radical; and the OR 2 group is always ortho to the group and the alkyl and alkoxy groups and residues mentioned contain not more than five carbon atoms, are prepared by one of the following methods: (a) an appropriate hydroxybiphenylene compound is carboxylated by reaction with CO 2 preferably in the presence of an alkali metal carbonate, (b) by oxidation of the corresponding 2-formyl-3-hydroxybiphenylene compounds, (c) by ring closure of an appropriate biphenyl or (d) by a Fries rearrangement of an appropriate ester, Grignard or Lithio compound, optionally followed by esterification, amidification or salt formation. Numerous intermediates used as starting materials and in their preparation are prepared; they are the following phenylenes: 2-acetyloxy- 3-methoxy-, 2-hydroxy-3-methoxy-, 2-acetyloxy-3-carboxy-, 2-acetyloxy-3-trifluoromethyl-, 2-hydroxy-3-trifluoromethyl-, 2-acetyl-3,6-dimethoxy-, 2-acetyl-6-hydroxy-, 2-hydroxy-6- methoxy-, 2-ethyl-6-hydroxy-, 2-acetyl-6- nitro-, 2-hydroxy-6-nitro-, 2-benzoyl-6-chloro-, 2-hydroxy-6-chloro-, 2-carboxy-6-methoxy-, 2- carboxy-6-hydroxy-, 2-carboxy-6-acetyloxy-, 2- acetoxy-6-trifluoromethl-, -, 2-hydroxy-6-trifluoromethyl-, 2-acetyl-6-methoxy- and oxime thereof, 2-acetamido-6-methoxy-, 2-amino-6- methoxy, 2-methoxy-6-phenyl-, 2-hydroxy-6- phenyl-, 2-benzyl-6-methoxy-, 2-benzyl-6-hydroxy-, 6-acetyl-3-methyl-2-methoxycarbonyl-, 2-acetyl-7-methyl-, 2-acetyloxy-7-methyl-, 2- acetyloxy-7-bromomethyl-, 2-hydroxy-7-methoxymethyl-, 2-fluoro-6-hydroxy-, 2-hydroxy-7- mercaptomethyl-, 2 - hydroxy - 7 - hydroxymethyl-, 2-dimethylaminomethyl-7-hydroxy-, 2-aminomethyl-7-hydroxy-, 2-methoxy-6-phenoxy-, 2-hydroxy-6-phenoxy-, 2,3-dimethoxy-6- hydroxy-, 2-chloro-6-mercapto-, 2-chloro-6- methylthio-, 2-cyano-6-methylthio, and 2-carboxy-6-methylthio-, -phenylenes. Pharmaceutical compositions in conventional forms for oral, parenteral and topical administration and having anti-inflammatory, anti-pyretic, analgesic, diuretic, antifibrinolytic and hypoglycaemic activity, comprise an above novel compound and a carrier therefor.
GB29540/70A 1969-06-25 1970-06-18 Orthohydroxybiphenylenecarboxylic acids and their derivatives Expired GB1272155A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US83665969A 1969-06-25 1969-06-25
US3029370A 1970-04-20 1970-04-20

Publications (1)

Publication Number Publication Date
GB1272155A true GB1272155A (en) 1972-04-26

Family

ID=26705874

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29540/70A Expired GB1272155A (en) 1969-06-25 1970-06-18 Orthohydroxybiphenylenecarboxylic acids and their derivatives

Country Status (7)

Country Link
JP (1) JPS4920771B1 (en)
CA (1) CA963021A (en)
CH (1) CH552553A (en)
DE (1) DE2031226A1 (en)
FR (1) FR2053010B1 (en)
GB (1) GB1272155A (en)
NL (1) NL7008626A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL7111913A (en) * 1970-09-15 1972-03-17
CA2728774A1 (en) * 2008-06-26 2009-12-30 Casella Waste Systems, Inc. Engineered fuel feed stock

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1522570A (en) * 1966-09-08 1968-04-26 Merck & Co Inc Phenylbenzoic acid compounds

Also Published As

Publication number Publication date
FR2053010A1 (en) 1971-04-16
JPS4920771B1 (en) 1974-05-27
FR2053010B1 (en) 1974-05-24
DE2031226A1 (en) 1971-01-07
CH552553A (en) 1974-08-15
CA963021A (en) 1975-02-18
NL7008626A (en) 1970-12-29

Similar Documents

Publication Publication Date Title
GB1278543A (en) TRICYCLIC o-HYDROXY CARBOXYLIC ACID DERIVATIVES
GB1419608A (en) Aroyl-substituted naphthaleneacetic acids and their derivatives
GB1038725A (en) Substituted indanes and indenes
GB1293626A (en) Substituted salicylic acid compounds
IE35424L (en) Cyclopropyl-p-tolyl-acetic acid derivatives.
GB1467110A (en) 4-phenyl-5-oxo-heptenoic acids
GB1497985A (en) Oxazolo-pyridines their preparation and use and compositions containing them
GB1268465A (en) Substituted salicylic acid compounds
GB1272155A (en) Orthohydroxybiphenylenecarboxylic acids and their derivatives
GB1374347A (en) 1,2-dihydroxy propane 2,3,3-tricarboxylic acid derivatives methods for their preparation and compositions containing them
GB1265279A (en)
IE35186B1 (en) Amines and a process for the manufacture thereof
GB1432503A (en) Cycloalkylalkylesters and process for their preparation
GB1273705A (en) A method for producing 3,5-diaryl-4-pyrazole acetic acids
GB1494773A (en) Hydroxyphenylalkanoic acids and lactones thereof
GB1497109A (en) Naphthalene derivatives
GB1219387A (en) Bicyclo[2.2.2]oct-2-ene-amino acid compounds
GB1473971A (en) 3-hydroxy-5,6-benzomorphinan derivatives
GB1278739A (en) Anilino salicylic acid derivatives
GB1389510A (en) Preparation of delta-keto-esters
SE7408868L (en)
GB1252248A (en)
GB1243321A (en) Antifibrinolytic compounds
GB1363640A (en) Esters of 2,2-diphenyl - cyclopropane - carboxylic acids
GB1472344A (en) Methylene dibenzocycloheptanes

Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees