GB1307028A - Phenethylamide derivatives and a process for the manufacture thereof - Google Patents

Phenethylamide derivatives and a process for the manufacture thereof

Info

Publication number
GB1307028A
GB1307028A GB5033171A GB5033171A GB1307028A GB 1307028 A GB1307028 A GB 1307028A GB 5033171 A GB5033171 A GB 5033171A GB 5033171 A GB5033171 A GB 5033171A GB 1307028 A GB1307028 A GB 1307028A
Authority
GB
United Kingdom
Prior art keywords
formula
group
acid
boric acid
compound
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
GB5033171A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1307028A publication Critical patent/GB1307028A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles

Abstract

1307028 3,4 - Dihydroxyphenylethylamine derivatives and boric acid complexes thereof F HOFFMANN-LA ROCHE & CO AG 29 Oct 1971 [30 Oct 1970] 50331/71 Headings C2B and C2C Novel compounds of Formula I wherein R represents a C 1-8 t-alkoxycarbonyl group, a 5-oxo-2-pyrrolidinecarbonyl group, a phenylsulphonyl group which may be C 1-7 alkyl-substituted or a nitro-substituted phenylthio group, and salts thereof are prepared by one of the following methods - (a) by acidic hydrolysis of a boric acid complex of the compound of Formula I above, (b) by dibenzylating a compound of Formula II wherein R<SP>1</SP> is a C 1-8 t-alkoxycarbonyl group, a N - benzyloxycarbonyl - 5 - oxo - 2 - pyrrolidinecarbonyl group or a phenylsulphonyl group which may be C 1-7 alkyl substituted, and (c) by mild basic hydrolysis of a compound of formula wherein R<SP>11</SP> is a C 1-8 t-alkoxycarbonyl group and R 1 is C 1-7 alkyl or phenyl. 0,0<SP>1</SP> - Nitrophenyldisulphide is obtained as a by-product from the acid hydrolysis of the boric acid complex of N-[(o-nitrophenyl)thio]- dopamine by method (a) above. Intermediates of Formula II above are prepared by reacting 3,4-dibenzyloxyphenethylamine or a salt thereof with an agent furnishing the group R<SP>1</SP>, e.g. p-toluene sulphonyl chloride or N-carbobenzyloxy-L-pyroglutamic acid dicyclohexylamine salt. Boric acid complexes of compounds of Formula I above are prepared by treating a solution of dopamine of Formula IV or a salt thereof with boric, acid or a borate at a pH of at least 7 to form a boric acid complex of the dopamine of the Formula IV in which the two phenolic hydroxy groups are esterified with boric acid and then treating this di-borate ester with an agent furnishing the radical R such as an acid halide, acid anhydride or acid azide particularly t-butoxycarbonyl azide. Pharmaceutical compositions in conventional forms for enteral or parenteral administration having hypotensive, - antipyretic and anti- Parkinson activity comprise an above novel compound I and a carrier therefor.
GB5033171A 1970-10-30 1971-10-29 Phenethylamide derivatives and a process for the manufacture thereof Expired GB1307028A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1604470A CH540230A (en) 1970-10-30 1970-10-30 Process for the production of phenethylamides

Publications (1)

Publication Number Publication Date
GB1307028A true GB1307028A (en) 1973-02-14

Family

ID=4414026

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5033171A Expired GB1307028A (en) 1970-10-30 1971-10-29 Phenethylamide derivatives and a process for the manufacture thereof

Country Status (10)

Country Link
AU (1) AU3357971A (en)
BE (1) BE774674A (en)
CA (1) CA958020A (en)
CH (2) CH540230A (en)
DE (1) DE2153825A1 (en)
FR (1) FR2111950B1 (en)
GB (1) GB1307028A (en)
IL (1) IL37702A (en)
NL (1) NL7113513A (en)
ZA (1) ZA716133B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4443473A (en) * 1981-06-30 1984-04-17 The Procter & Gamble Company Carbamate derivatives
DE102007035642A1 (en) * 2007-07-30 2009-02-12 Grietje Beck Substances for protecting cells and tissues against damage due to unfavorable conditions

Also Published As

Publication number Publication date
CH540230A (en) 1973-08-15
BE774674A (en) 1972-05-02
CH544070A (en) 1973-11-15
DE2153825A1 (en) 1972-05-04
ZA716133B (en) 1972-06-28
NL7113513A (en) 1972-05-03
CA958020A (en) 1974-11-19
FR2111950A1 (en) 1972-06-09
FR2111950B1 (en) 1975-04-18
IL37702A (en) 1975-02-10
AU3357971A (en) 1973-03-22
IL37702A0 (en) 1971-11-29

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees