GB1002851A - 1-methyl-3-(m-hydroxyphenyl)-3-alkylpyrrolidines and ethers and esters thereof and their acid addition salts - Google Patents

1-methyl-3-(m-hydroxyphenyl)-3-alkylpyrrolidines and ethers and esters thereof and their acid addition salts

Info

Publication number
GB1002851A
GB1002851A GB375/61A GB37561A GB1002851A GB 1002851 A GB1002851 A GB 1002851A GB 375/61 A GB375/61 A GB 375/61A GB 37561 A GB37561 A GB 37561A GB 1002851 A GB1002851 A GB 1002851A
Authority
GB
United Kingdom
Prior art keywords
methoxyphenyl
methyl
radical
hydrogen atom
ethyl
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
GB375/61A
Inventor
John Frederick Cavalla
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Priority to GB375/61A priority Critical patent/GB1002851A/en
Publication of GB1002851A publication Critical patent/GB1002851A/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
    • C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—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 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
    • C07D207/12—Oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises racemic and optically active compounds of the general formula <FORM:1002851/C2/1> (wherein R represents a hydrogen atom or a lower alkyl or lower alkanoyl radical, R1 represents a C2- 4 alkyl radical, and R2 and R3 each represents a hydrogen atom or a methyl or ethyl radical, R2 and R3 being chosen such that they are not both alkyl radicals) and pharmaceutically acceptable acid-addition salts thereof, pharmaceutical preparations containing them, and their preparation by (a)-when R is a hydrogen atom or a lower alkyl radical and R2 and R3 are both hydrogen atoms-reducing a compound of the formula <FORM:1002851/C2/2> with a complex metal hydride (when R in the starting material is an alkonoyl radical, R in the product is a hydrogen atom), (b)-when R is a hydrogen atom-heating a corresponding 1-methyl - 3 - (m - alkoxyphenyl) - 3 - alkyl-pyrrolidine with an acidic reagent capable of cleaving the ether linkage, (c)-when R is a lower alkanoyl radical-acylating the corresponding phenol, (d) methylating a compound of the formula <FORM:1002851/C2/3> or (e)-when R is a lower alkyl radical, R2 is a methyl or ethyl radical and R3 is a hydrogen atom-reducing a compound of the formula <FORM:1002851/C2/4> (wherein R4 represents a methyl or ethyl radical and A(-) represents an anion), optionally followed in each case by acid addition salt formation. An optically active product may be obtained by using an optically active starting material or by resolving a racemic product. The terms "lower alkyl radical" and "lower alkanoyl radical" are defined as radicals containing not more than four carbon atoms. The following intermediates are prepared from the starting materials indicated in parentheses: N - methyl - a - (m - methoxyphenyl) - a - propylsuccinimide (ethyl - a - cyano - b - (m - methoxyphenyl) - b - propylacrylate, via ethyl a ,b - dicyano - b - (m - methoxyphenyl) - hexanoate and a - (m - methoxyphenyl) - a - propylsuccinic acid); 5 - methyl - 3 - (m - methoxyphenyl) - 3 - propylpyrrolidin (a - (m - methoxyphenyl) - valeronitrile, via 4-cyano-4-(m - methoxyphenyl) - heptanol - 2 and 4 - aminomethyl - 4 - (m - methoxyphenyl) - heptanol - 2); 3 - (m - methoxyphenyl) - 3 - propylpyrrolidine (a - (m - methoxyphenyl) - a - propylsuccinic acid, via N - benzyl - a - (m - methoxyphenyl) - a - propylsuccinimide and 1 - benzyl - 3 - (m - methoxyphenyl) - 3 - propylpyrrolidine, or 2 - (21 - chloroethyl) - 2 - (m - methoxyphenyl) - valeronitrile); 1,2 - dimethyl - 3 - (m - methoxyphenyl - 3 - propyl - 1 - pyrrolinium iodide (m-methoxybenzyl cyanide, via a - (m - methoxyphenyl) - valeronitrile, 3 - cyano - 3 - (m - methoxyphenyl) - 1 - chlorohexane and 2 - methyl - 3 - (m - methoxyphenyl) - 3 - propyl - 1 - pyrroline. The compounds of the invention are analgesics and may be administered orally or parenterally in the form of pharmaceutical preparations containing them in association with a carrier or diluent. Reference has been directed by the Comptroller to Specification 928,007.
GB375/61A 1961-01-04 1961-01-04 1-methyl-3-(m-hydroxyphenyl)-3-alkylpyrrolidines and ethers and esters thereof and their acid addition salts Expired GB1002851A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB375/61A GB1002851A (en) 1961-01-04 1961-01-04 1-methyl-3-(m-hydroxyphenyl)-3-alkylpyrrolidines and ethers and esters thereof and their acid addition salts

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB375/61A GB1002851A (en) 1961-01-04 1961-01-04 1-methyl-3-(m-hydroxyphenyl)-3-alkylpyrrolidines and ethers and esters thereof and their acid addition salts

Publications (1)

Publication Number Publication Date
GB1002851A true GB1002851A (en) 1965-09-02

Family

ID=9703312

Family Applications (1)

Application Number Title Priority Date Filing Date
GB375/61A Expired GB1002851A (en) 1961-01-04 1961-01-04 1-methyl-3-(m-hydroxyphenyl)-3-alkylpyrrolidines and ethers and esters thereof and their acid addition salts

Country Status (1)

Country Link
GB (1) GB1002851A (en)

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