GB1220591A

GB1220591A – Beta-phenylalanine derivatives
– Google Patents

GB1220591A – Beta-phenylalanine derivatives
– Google Patents
Beta-phenylalanine derivatives

Info

Publication number
GB1220591A

GB1220591A
GB24754/67A
GB2475467A
GB1220591A
GB 1220591 A
GB1220591 A
GB 1220591A
GB 24754/67 A
GB24754/67 A
GB 24754/67A
GB 2475467 A
GB2475467 A
GB 2475467A
GB 1220591 A
GB1220591 A
GB 1220591A
Authority
GB
United Kingdom
Prior art keywords
methoxy
hydroxy
general formula
acid
ethoxy
Prior art date
1967-05-26
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
GB24754/67A
Inventor
Pierre Crooij
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.)

RIT RECH IND THERAPEUT

Original Assignee
RIT RECH IND THERAPEUT
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.)
1967-05-26
Filing date
1967-05-26
Publication date
1971-01-27

1967-05-26
Application filed by RIT RECH IND THERAPEUT
filed
Critical
RIT RECH IND THERAPEUT

1967-05-26
Priority to GB24754/67A
priority
Critical
patent/GB1220591A/en

1968-05-16
Priority to DE19681768466
priority
patent/DE1768466A1/en

1968-05-18
Priority to ES354058A
priority
patent/ES354058A1/en

1968-05-24
Priority to CH95170A
priority
patent/CH517700A/en

1968-05-24
Priority to AT499368A
priority
patent/AT286968B/en

1968-05-24
Priority to CH769568A
priority
patent/CH515888A/en

1968-05-24
Priority to BE715588D
priority
patent/BE715588A/xx

1968-05-24
Priority to NO204168A
priority
patent/NO121788B/no

1968-05-27
Priority to FR1592518D
priority
patent/FR1592518A/fr

1968-05-27
Priority to FR153043A
priority
patent/FR7889M/fr

1968-05-27
Priority to NL6807465A
priority
patent/NL6807465A/xx

1971-01-27
Publication of GB1220591A
publication
Critical
patent/GB1220591A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

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

C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups

C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms

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

C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups

C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton

C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton

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

C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups

C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton

C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form

C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C47/00—Compounds having —CHO groups

C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings

C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings

C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings

C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members

C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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

C07D263/36—One oxygen atom

C07D263/42—One oxygen atom attached in position 5

C—CHEMISTRY; METALLURGY

C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING

C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE

C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture

C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions

Abstract

1,220,591. #-Phenylalanine derivatives. RECHERCHE ET INDUSTRIE THERAPEUTIQUES R.I.T. 2 May, 1968 [26 May, 1967], No. 24754/67. Heading C2C. Novel DL-, D- and L-#-phenylalanine derivatives of the general formula wherein R 1 and R 2 are each a methyl or ethyl group or one of R 1 and R 2 is a hydrogen atom or a C 2-30 acyl group and the other is a methyl or ethyl group; R 3 is a hydrogen atom, a pharmaceutically acceptable non-toxic alkali metal, ammonium, a pharmaceutically acceptable non-toxic protonated amine with which the rest of the molecule forms an acid addition salt, or a C 1-30 alkyl or C 2-30 alkenyl radical; X is a chlorine, bromine, iodine or fluorine atom; and Z is a hydrogen atom or a C 2-30 carboxylic acyl radical; and non-toxic acid addition salts thereof are prepared (a) when R 3 and Z are each a hydrogen atom, by hydrolysis and decarboxylation of a 2-benzyl-2- amino-malonic acid ester derivative of the general formula wherein Alk1 is a C 1-4 alkyl radical and Y is a formyl, acetyl, benzoyl, phthaloyl or benzyloxycarbonyl radical, the reaction being conducted in a solvent under the influence of heat in an acid medium and in the presence of a reducing agent; or (b) when R 3 and Z are each a hydrogen atom, by reduction of a phenyl-pyruvic acid derivative of the general formula wherein M is as R 3 above with the exception of an alkyl or alkenyl radical, under mild conditions in the presence of ammonium hydroxide solution, followed optionally by conversion of the product to a non-toxic acid addition salt thereof or resolution of the racemic product into its D- and L-enantiomers. The L(-)ephedrine salt of (-)3-methoxy-4- hydroxy – 5 – bromo – N – acetyl – phenylalanine is prepared by adding DL-3-methoxy-4-hydroxy-5-bronio-N-acetyl-phenylalanine to an ethanolic solution of L(-)ephedrine diluted with acetone. 2 – Benzyl – 2 – aminomalonic acid ester derivatives of the second general formula above wherein R 1 is a methyl or ethyl group and R 2 is a hydrogen atom are prepared by halogenation of 3-(methoxy or ethoxy)-4-hydroxybenzaldehyde, reduction of the resulting 3-(methoxy or ethoxy) – 4 – hydroxy – 5 – halobenzaldehyde with sodium borohydride, reaction of the 3-(methoxy or ethoxy) – 4 – hydroxy – 5 – halobenzyl alcohol so obtained with a hydrogen halide and reaction of the resulting 3-(methoxy or ethoxy)-4- hydroxy-5-halobenzyl halide with an alkali metal salt of a 2-aminomalonic acid ester derivative of the general formula wherein M+ is an alkali metal ion. Phenylpyruvic acid derivatives of the third general formula above are prepared by reaction of a 3-(methoxy or ethoxy)-4-hydroxy-5-halobenzaldehyde with N-acetylglycine in the presence of excess acetic anhydride and sodium acetate, mild alkaline hydrolysis of the resulting azlactone of the general formula and acid or alkaline hydrolysis of the resulting 2 – acetamido – 3 – [31– methoxy or ethoxy)- 41 – hydroxy – 51– halo] – phenylpropenoic acid. 5 – Bromo – isovanallin is prepared by treatment of 5-bromovanallin with anhydrous aluminium chloride in pyridine, while heating, and reaction of the resulting 5-bromo-protocatechualdehyde with methyl iodide and sodium bicarbonate in acetone. Acetamido – 3,4 – dihydroxy – 5 – chlorobenzylmalonic acid diethyl ester is prepared by treatment of diethyl acetamido-(3-methoxy-4-hydroxy – 5 – chlorobenzyl) – malonate with aluminium chloride in pyridine. Pharmaceutical compositions having hypotensive activity comprise, as active ingredient, a DL-, D- or L-#-phenylalanine derivative of the first general formula above or a non-toxic acid addition salt thereof, together with a pharmaceutically acceptable diluent or carrier, and may be administered orally, intramuscularly, intravenously or subcutaneously.

GB24754/67A
1967-05-26
1967-05-26
Beta-phenylalanine derivatives

Expired

GB1220591A
(en)

Priority Applications (11)

Application Number
Priority Date
Filing Date
Title

GB24754/67A

GB1220591A
(en)

1967-05-26
1967-05-26
Beta-phenylalanine derivatives

DE19681768466

DE1768466A1
(en)

1967-05-26
1968-05-16

New ss-phenylalanine derivatives

ES354058A

ES354058A1
(en)

1967-05-26
1968-05-18
Beta-phenylalanine derivatives

CH95170A

CH517700A
(en)

1967-05-26
1968-05-24
(A) Cpds. (I) R’ and R2 = Me or Et or one only of R’ or R2 may = H or (1-30C)acyl R3 = H, non-toxic cation chosen from the alkali metals and opt. su

AT499368A

AT286968B
(en)

1967-05-26
1968-05-24

Process for the preparation of new DL-, D- and L-β-phenylalanine derivatives

CH769568A

CH515888A
(en)

1967-05-26
1968-05-24

Process for the preparation of beta-phenylalanine derivatives

BE715588D

BE715588A
(en)

1967-05-26
1968-05-24

NO204168A

NO121788B
(en)

1967-05-26
1968-05-24

FR1592518D

FR1592518A
(en)

1967-05-26
1968-05-27

FR153043A

FR7889M
(en)

1967-05-26
1968-05-27

NL6807465A

NL6807465A
(en)

1967-05-26
1968-05-27

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

GB24754/67A

GB1220591A
(en)

1967-05-26
1967-05-26
Beta-phenylalanine derivatives

Publications (1)

Publication Number
Publication Date

GB1220591A
true

GB1220591A
(en)

1971-01-27

Family
ID=10216725
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB24754/67A
Expired

GB1220591A
(en)

1967-05-26
1967-05-26
Beta-phenylalanine derivatives

Country Status (8)

Country
Link

AT
(1)

AT286968B
(en)

BE
(1)

BE715588A
(en)

CH
(1)

CH515888A
(en)

DE
(1)

DE1768466A1
(en)

ES
(1)

ES354058A1
(en)

FR
(2)

FR7889M
(en)

GB
(1)

GB1220591A
(en)

NL
(1)

NL6807465A
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

WO2004110500A1
(en)

*

2002-08-02
2004-12-23
Mallinckrodt Inc.
Radioactively labelled amino acid analogues, their preparation and use

Families Citing this family (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

BE789586A
(en)

*

1972-03-27
1973-04-02
Hoffmann La Roche

PROCESS FOR THE PREPARATION OF 3,4,5-TRIMETHOXY-BENZALDEHYDE

1967

1967-05-26
GB
GB24754/67A
patent/GB1220591A/en
not_active
Expired

1968

1968-05-16
DE
DE19681768466
patent/DE1768466A1/en
active
Pending

1968-05-18
ES
ES354058A
patent/ES354058A1/en
not_active
Expired

1968-05-24
AT
AT499368A
patent/AT286968B/en
not_active
IP Right Cessation

1968-05-24
CH
CH769568A
patent/CH515888A/en
not_active
IP Right Cessation

1968-05-24
BE
BE715588D
patent/BE715588A/xx
unknown

1968-05-27
FR
FR153043A
patent/FR7889M/fr
not_active
Expired

1968-05-27
FR
FR1592518D
patent/FR1592518A/fr
not_active
Expired

1968-05-27
NL
NL6807465A
patent/NL6807465A/xx
unknown

Cited By (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

WO2004110500A1
(en)

*

2002-08-02
2004-12-23
Mallinckrodt Inc.
Radioactively labelled amino acid analogues, their preparation and use

US7189383B2
(en)

2002-08-02
2007-03-13
Mallinckrodt Inc.
Radioactively labelled amino acid analogues, their preparation and use

AU2003304200B2
(en)

*

2002-08-02
2009-10-01
Vrije Universiteit Brussel
Radioactively labelled amino acid analogues, their preparation and use

Also Published As

Publication number
Publication date

CH515888A
(en)

1971-11-30

BE715588A
(en)

1968-10-16

NL6807465A
(en)

1968-11-27

ES354058A1
(en)

1970-02-16

DE1768466A1
(en)

1971-09-16

FR1592518A
(en)

1970-05-19

AT286968B
(en)

1971-01-11

FR7889M
(en)

1970-05-04

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