GB1205173A

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

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
1967-02-21
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.)
1967-02-21
Filing date
1968-02-12
Publication date
1970-09-16

1968-02-12
Application filed by Sandoz AG
filed
Critical
Sandoz AG

1970-09-16
Publication of GB1205173A
publication
Critical
patent/GB1205173A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

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

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, n1 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 R11 1 is a C 1-4 alkyl radical and Z is a hydrogen atom or a -COOR111 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 -COOR111 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 -COOR111 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 -COOR111 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 -COOR11 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

US6867221B2
(en)

*

2001-08-30
2005-03-15
Kowa Co., Ltd.
Cyclic amine compounds and pharmaceutical composition containing the same

US6395753B1
(en)

*

2001-08-30
2002-05-28
Kowa Co., Ltd.
Cyclic amine compounds and pharmaceutical composition containing the same

1968

1968-02-09
CH
CH198668A
patent/CH514581A/en
not_active
IP Right Cessation

1968-02-12
GB
GB6857/68A
patent/GB1205173A/en
not_active
Expired

1968-02-19
ES
ES350640A
patent/ES350640A1/en
not_active
Expired

1968-02-20
DE
DE19681668968
patent/DE1668968A1/en
active
Pending

1968-02-21
FR
FR1575591D
patent/FR1575591A/fr
not_active
Expired

1969

1969-04-01
ES
ES365515A
patent/ES365515A1/en
not_active
Expired

1972

1972-04-03
JP
JP47032689A
patent/JPS4831101B1/ja
active
Pending

1972-04-03
JP
JP47032690A
patent/JPS4831102B1/ja
active
Pending

Also Published As

Publication number
Publication date

ES350640A1
(en)

1969-10-01

CH514581A
(en)

1971-10-31

DE1668968A1
(en)

1971-10-14

JPS4831101B1
(en)

1973-09-26

ES365515A1
(en)

1971-03-16

FR1575591A
(en)

1969-07-25

JPS4831102B1
(en)

1973-09-26

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Legal Events

Date
Code
Title
Description

1971-01-27
PS
Patent sealed

1976-09-08
PLNP
Patent lapsed through nonpayment of renewal fees

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