GB634073A - Process for the preparation of local anaesthetics - Google Patents

Process for the preparation of local anaesthetics

Info

Publication number
GB634073A
GB634073A GB15257/44A GB1525744A GB634073A GB 634073 A GB634073 A GB 634073A GB 15257/44 A GB15257/44 A GB 15257/44A GB 1525744 A GB1525744 A GB 1525744A GB 634073 A GB634073 A GB 634073A
Authority
GB
United Kingdom
Prior art keywords
acid
amide
chloride
dibenzylaminoacetic
trimethyl
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
GB15257/44A
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.)
AstraZeneca AB
Original Assignee
Astra AB
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 Astra AB filed Critical Astra AB
Publication of GB634073A publication Critical patent/GB634073A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Anilides of the general formula <FORM:0634073/IV (b)/1> wherein R1 and R5 and at least one of R2, R3 and R4 (especially R3) represent acyclic hydrocarbon residues and the rest hydrogen, X represents a mono- or di-substituted amino group and m and n are whole numbers, m being greater than or equal to n, are manufactured by condensing a phenylamine, substituted in the 2- and 6-positions and at least one other position by an acylic hydrocarbon residue, or a salt thereof, with an aminoalkylcarboxylic acid containing the group or groups X, or an alkyl ester or amide thereof, or with a halogenated alkylcarboxylic acid, or an anhydride, halide or amide thereof, followed in the latter case by further condensation with a primary or secondary amine. The condensation of the phenylamines or their hydrohalides with halogenated alkylcarboxylic acids or their derivatives, and the treatment of the products with amines, may be effected under the conditions set out in Specification 634,072. The products are useful as local anaesthetics, preferably after conversion into their salts with organic or inorganic acids, e.g. tartaric, citric or especially hydrochloric acid. Examples illustrate various features of the invention, using the following starting materials : 2 : 4 - dimethyl - 6 - ethyl -, 2 : 4 : 6-trimethyl- and 2 : 6-diethyl-4-methylaniline; the hydrochlorides of 2 : 3 : 4 : 5 : 6-pentamethyl- and 2 : 3 : 6 - trimethyl - aniline; N-allylaminoacetic acid, b -(N-diethylamino)-aminoacetic acid amide; chloracetyl chloride, b -chloropropionyl chloride, a -bromopropionyl bromide, chloracetic acid, chloracetamide, chloracetic anhydride and a : b -dibromopropionyl chloride; diethylamine, dimethylamine and n- or iso-butylamine. Additional amines specified for use in the second of the alternative processes are methylamine, allylamine cyclohexylamine, 1 : 2 : 3 : 4 - tetrahydro - 2 - naphthylamine, benzylamine, piperidine and 1 : 2 : 3 : 4-tetrahydroisoquinoline. N - Dibenzylaminoacetic acid amide is prepared by refluxing ethyl chloracetate with dibenzylamine in benzene, and treating the resulting N-dibenzylaminoacetic ester with ammonia in alcohol.
GB15257/44A 1944-05-25 1944-08-10 Process for the preparation of local anaesthetics Expired GB634073A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE437444 1944-05-25

Publications (1)

Publication Number Publication Date
GB634073A true GB634073A (en) 1950-03-15

Family

ID=20313597

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15257/44A Expired GB634073A (en) 1944-05-25 1944-08-10 Process for the preparation of local anaesthetics

Country Status (1)

Country Link
GB (1) GB634073A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2794835A (en) * 1952-07-14 1957-06-04 Astra Apotekarnes Kem Fab Alkyl alaninanilides
DE1054462B (en) * 1955-10-27 1959-04-09 Espe Fabrik Pharm Praeparate G Process for the production of locally anesthetically effective polyaminoacetanilides
US2917541A (en) * 1954-08-03 1959-12-15 Roussel Uclaf New n,n-dibenzyl amino acid compounds and process of making same
US2991307A (en) * 1954-12-14 1961-07-04 Roussel Uclaf Process of resolving nu, nu-dibenzyl-dl-alpha-amino acids and products
US3108997A (en) * 1957-10-31 1963-10-29 Astra Ab Morpholino lower alkanoyl xylidides and toluidides
US3334100A (en) * 1960-04-22 1967-08-01 Sterling Drug Inc Amino-lower-alkanoylanilines

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2794835A (en) * 1952-07-14 1957-06-04 Astra Apotekarnes Kem Fab Alkyl alaninanilides
US2917541A (en) * 1954-08-03 1959-12-15 Roussel Uclaf New n,n-dibenzyl amino acid compounds and process of making same
US2991307A (en) * 1954-12-14 1961-07-04 Roussel Uclaf Process of resolving nu, nu-dibenzyl-dl-alpha-amino acids and products
DE1054462B (en) * 1955-10-27 1959-04-09 Espe Fabrik Pharm Praeparate G Process for the production of locally anesthetically effective polyaminoacetanilides
US3108997A (en) * 1957-10-31 1963-10-29 Astra Ab Morpholino lower alkanoyl xylidides and toluidides
US3334100A (en) * 1960-04-22 1967-08-01 Sterling Drug Inc Amino-lower-alkanoylanilines

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