GB1420802A

GB1420802A – Substituted geranyl acetic acids and pharmaceutical compositions thereof
– Google Patents

GB1420802A – Substituted geranyl acetic acids and pharmaceutical compositions thereof
– Google Patents
Substituted geranyl acetic acids and pharmaceutical compositions thereof

Info

Publication number
GB1420802A

GB1420802A
GB2894073A
GB2894073A
GB1420802A
GB 1420802 A
GB1420802 A
GB 1420802A
GB 2894073 A
GB2894073 A
GB 2894073A
GB 2894073 A
GB2894073 A
GB 2894073A
GB 1420802 A
GB1420802 A
GB 1420802A
Authority
GB
United Kingdom
Prior art keywords
substituted
condensation product
cyanoacetate
acids
geranylacetic
Prior art date
1972-07-14
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
GB2894073A
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.)

Princeton Biomedix Inc

Original Assignee
Princeton Biomedix 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.)
1972-07-14
Filing date
1973-06-19
Publication date
1976-01-14

1973-06-19
Application filed by Princeton Biomedix Inc
filed
Critical
Princeton Biomedix Inc

1976-01-14
Publication of GB1420802A
publication
Critical
patent/GB1420802A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone

C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof

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

C07C255/00—Carboxylic acid nitriles

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms

C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than 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

C07C57/26—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings

C07C57/28—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings containing an adamantane ring system

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms

C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms 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

C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid

C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems

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

1420802 Substituted geranylacetic acids PRINCETON BIOMEDIX Inc 19 June 1973 [14 July 1972] 28940/73 Heading C2C The invention comprises substituted geranylacetic acids of the structure wherein R is selected from substituted and unsubstituted alkyl having from 1 to 10 carbon atoms, aryl, aralkyl, alkaryl, cycloalkenyl and substituted and unsubstituted cycloalkyl having from 5 to 8 carbon atoms in the ring; and R1 is selected from H, COOH and ON; provided that when R is cyclohexyl or cyclopentyl, R1 is COOH or CN and salts thereof. The substituted geranylacetic acids of the structure wherein R is as above, are prepared by a method comprising the steps of condensing a carbonyl compound selected from R11=O and in which R11 and R111 are the divalent and trivalent derivatives of R with ethyl cyanoacetate to form a condensation product of the formula reducing said condensation product with sodium borohydride to form the cyanoacetate of the formula geranylating said cyanoacetate with a geranyl halide, hydrolysing the product of said geranylation step and decarboxylating the same to form said substituted geranylacetic acid. Cyclohexylgeranylacetic acid may be prepared by a method which comprises condensing citral with diethyl malonate to form a condensation product, reducing said condensation product with sodium borohydride to form diethyl 2- geranylmalonate; reacting this with sodium hydride and alkylating with cyclohexyl bromide to form diethyl 2-cyclohexyl-2-geranylmalonate which in turn is hydrolysed with potassium hydroxide, acidified with sulphuric acid and decarboxylated by heating at up to 160‹ C. Substituted geranylmalonic acids of the structure wherein R is as defined above, may be prepared by a method which comprises the steps of condensing a carbonyl compound selected from R11=O and (wherein R11 and R111 are as above) with ethyl cyanoacetate to form a condensation product of the formula reducing said condensation product with sodium borohydride to form the cyanoacetate of formula geranylating this with a geranyl halide and hydrolysing the product to form said substituted geranylmalonic acid. The compounds of the invention are used for treating dermatological disorders.

GB2894073A
1972-07-14
1973-06-19
Substituted geranyl acetic acids and pharmaceutical compositions thereof

Expired

GB1420802A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US27168772A

1972-07-14
1972-07-14

Publications (1)

Publication Number
Publication Date

GB1420802A
true

GB1420802A
(en)

1976-01-14

Family
ID=23036632
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB2894073A
Expired

GB1420802A
(en)

1972-07-14
1973-06-19
Substituted geranyl acetic acids and pharmaceutical compositions thereof

Country Status (8)

Country
Link

JP
(1)

JPS4943917A
(en)

AU
(1)

AU5677773A
(en)

BE
(1)

BE802155A
(en)

CA
(1)

CA970365A
(en)

DE
(1)

DE2335067A1
(en)

FR
(1)

FR2192826B1
(en)

GB
(1)

GB1420802A
(en)

ZA
(1)

ZA734022B
(en)

Cited By (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4289786A
(en)

1978-11-28
1981-09-15
Kuraray Co., Ltd.
Farnesylacetic acid ester derivatives

US8575386B2
(en)

2006-06-15
2013-11-05
Givaudan S.A.
Fragrance compounds

Families Citing this family (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB0501237D0
(en)

*

2005-01-21
2005-03-02
Givaudan Sa
Organic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

NL130627C
(en)

*

1961-05-26

1973

1973-06-12
CA
CA173,830A
patent/CA970365A/en
not_active
Expired

1973-06-12
AU
AU56777/73A
patent/AU5677773A/en
not_active
Expired

1973-06-13
ZA
ZA734022A
patent/ZA734022B/en
unknown

1973-06-19
GB
GB2894073A
patent/GB1420802A/en
not_active
Expired

1973-07-10
DE
DE19732335067
patent/DE2335067A1/en
active
Pending

1973-07-10
BE
BE133329A
patent/BE802155A/en
unknown

1973-07-13
FR
FR7325724A
patent/FR2192826B1/fr
not_active
Expired

1973-07-14
JP
JP48079755A
patent/JPS4943917A/ja
active
Pending

Cited By (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4289786A
(en)

1978-11-28
1981-09-15
Kuraray Co., Ltd.
Farnesylacetic acid ester derivatives

US8575386B2
(en)

2006-06-15
2013-11-05
Givaudan S.A.
Fragrance compounds

US9057041B2
(en)

2006-06-15
2015-06-16
Givaudan, S.A.
Fragrance compounds

US9447364B2
(en)

2006-06-15
2016-09-20
Givaudan S.A.
Fragrance compounds

US9585362B2
(en)

2006-06-15
2017-03-07
Givaudan S.A.
Fragrance compounds

Also Published As

Publication number
Publication date

ZA734022B
(en)

1974-09-25

CA970365A
(en)

1975-07-01

AU5677773A
(en)

1974-12-12

DE2335067A1
(en)

1974-01-31

FR2192826B1
(en)

1977-07-01

FR2192826A1
(en)

1974-02-15

BE802155A
(en)

1973-11-05

JPS4943917A
(en)

1974-04-25

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Legal Events

Date
Code
Title
Description

1976-05-26
PS
Patent sealed

1977-10-26
PLE
Entries relating assignments, transmissions, licences in the register of patents

1979-01-31
PCNP
Patent ceased through non-payment of renewal fee

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