GB1205173A - Novel bis-phenoxy-acetic acid derivatives, the preparation thereof and compositions containing the same - Google Patents

Novel bis-phenoxy-acetic acid derivatives, the preparation thereof and compositions containing the same

Info

Publication number
GB1205173A
GB1205173A GB6857/68A GB685768A GB1205173A GB 1205173 A GB1205173 A GB 1205173A GB 6857/68 A GB6857/68 A GB 6857/68A GB 685768 A GB685768 A GB 685768A GB 1205173 A GB1205173 A GB 1205173A
Authority
GB
United Kingdom
Prior art keywords
general formula
bis
radical
phenoxy
reaction
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
GB6857/68A
Inventor
Rudolf Gustav Griot
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.)
Sandoz AG
Original Assignee
Sandoz AG
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 Sandoz AG filed Critical Sandoz AG
Publication of GB1205173A publication Critical patent/GB1205173A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • A61P3/06—Antihyperlipidemics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • 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
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • 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
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
    • C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
    • C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring

Landscapes

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

Abstract

1,205,173. Bis-phenoxy-acetic acid derivatives. SANDOZ Ltd. 12 Feb., 1968 [21 Feb., 1967; 14 July, 1967], No. 6857/68. Heading C2C. Novel bis-phenoxy-acetic acid derivatives of the general formula wherein each Y is the same and is a 4-biphenylyl, 4 - (4 - chlorophenyl) phenyl or 4 - trifluoromethylphenyl radical and R 1 is a hydrogen atom, a C 1-4 alkyl radical or a heterocyclic radical of the formula in which n is 0 or a whole number from 1 to 4, n<SP>1</SP> is 4 or 5 and R 2 is a C 1-4 alkyl radical, and salts thereof are prepared (a) when R 1 is a heterocyclic radical as defined above, (i) by reaction of a bis-phenoxy-acetic acid alkyl ester derivative of the general formula wherein R<SP>11</SP> 1 is a C 1-4 alkyl radical and Z is a hydrogen atom or a -COOR<SP>11</SP>1 radical, with an alcohol of the general formula R 1 OH, in which R 1 is a heterocyclic radical as defined above, at a temperature sufficiently high for a partial decarboxylation to occur when Z is a -COOR<SP>11</SP>1 radical; or (ii) by reaction of a bis-phenoxyacetyl halide derivative of the general formula wherein X is a chlorine or bromine atom, with an alcohol or salt thereof of the general formula R 1 OP, in which R 1 is a heterocyclic radical as defined above and P is a hydrogen atom or an alkali metal atom; (b) when R 1 is a C 1-4 alkyl radical, (i) by reaction of an alkali metal phenolate of the general formula Y-O-M, in which M is an alkali metal atom, with a dihaloacetic acid ester of the general formula X 2 CHCOOR 1 , wherein R 1 is a C 1-4 , alkyl radical; (ii) by partial decarboxylation of a bis-phenoxymalonic acid alkyl ester of the second general formula above, wherein Z is a -COOR<SP>11</SP>1 radical; or (iii) by reaction of a bis-phenoxyacetic acid derivative of the fourth general formula above, wherein X is a chlorine or bromine atom or a hydroxyl radical with an alcohol or salt thereof of the fifth general formula above, wherein R 1 is a C 1-4 alkyl radical, with the proviso that when X is a hydroxyl radical, P is a hydrogen atom and the reaction is carried out in the presence of a conventional esterification catalyst; or (c) when R 1 is a hydrogen atom, (i) by partial decarboxylation of a bis-phenoxy-malonic acid derivative of the general formula (ii) by saponification of a bis-phenoxy-acetic acid alkyl ester of the second general formula above, the temperature being sufficiently high for a partial decarboxylation to occur when Z is a -COOR<SP>11</SP>1 radical; or (iii) by reaction of a dihaloacetic acid salt of the general formula X 2 CHCOOM with an alkali metal phenolate of the sixth general formula above; followed optionally by salt-formation. Bis-phenoxy-malonic acid derivatives of the eighth general formula above are prepared by saponification of the corresponding bis-phenoxyacetic acid dialkyl ester of the second general formula above, wherein Z is a -COOR<SP>11</SP> 1 radical, which in turn is prepared by reaction of a dihalomalonic acid ester of the general formula with an alkali metal phenolate of the sixth general formula at a temperature not exceeding 80‹ C. Bis-phenoxy-acetyl halide derivatives of the fourth general formula above are prepared by reaction of a bis-phenoxy-acetic acid derivative of the first general formula above, wherein R 1 is a hydrogen atom with a chlorinating or brominating agent. Pharmaceutical compositions having hypocholesteremic activity comprise as active ingredient a bis-phenoxy-acetic acid derivative of the first general formula above or a non-toxic, pharmaceutically acceptable salt thereof in association with a physiologically acceptable carrier or diluent.
GB6857/68A 1967-02-21 1968-02-12 Novel bis-phenoxy-acetic acid derivatives, the preparation thereof and compositions containing the same Expired GB1205173A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61745667A 1967-02-21 1967-02-21
US65335067A 1967-07-14 1967-07-14

Publications (1)

Publication Number Publication Date
GB1205173A true GB1205173A (en) 1970-09-16

Family

ID=27088030

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6857/68A Expired GB1205173A (en) 1967-02-21 1968-02-12 Novel bis-phenoxy-acetic acid derivatives, the preparation thereof and compositions containing the same

Country Status (6)

Country Link
JP (2) JPS4831101B1 (en)
CH (1) CH514581A (en)
DE (1) DE1668968A1 (en)
ES (2) ES350640A1 (en)
FR (1) FR1575591A (en)
GB (1) GB1205173A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2088140B1 (en) * 1970-05-22 1974-02-22 Sertha Centre Rech
BE792853A (en) * 1971-12-18 1973-06-15 Merck Patent Gmbh CARBOXYLIC ACID DERIVATIVES AND THEIR PREPARATION PROCESS
IT1282693B1 (en) * 1996-02-27 1998-03-31 Dompe Spa GEMINAL CARBOXYLIC ACIDS AND THEIR ESTERS; PHARMACEUTICAL PREPARATIONS THAT CONTAIN THEM USEFUL IN THE TREATMENT OF BONE DYSMETABOLISM
US6395753B1 (en) * 2001-08-30 2002-05-28 Kowa Co., Ltd. Cyclic amine compounds and pharmaceutical composition containing the same
US6867221B2 (en) * 2001-08-30 2005-03-15 Kowa Co., Ltd. Cyclic amine compounds and pharmaceutical composition containing the same

Also Published As

Publication number Publication date
CH514581A (en) 1971-10-31
DE1668968A1 (en) 1971-10-14
ES350640A1 (en) 1969-10-01
FR1575591A (en) 1969-07-25
JPS4831101B1 (en) 1973-09-26
ES365515A1 (en) 1971-03-16
JPS4831102B1 (en) 1973-09-26

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Legal Events

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