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GB869978A - Method of producing n-alkyl-and-cycloalkyl-piperidine carboxylic acid amides - Google Patents

Method of producing n-alkyl-and-cycloalkyl-piperidine carboxylic acid amides

Info

Publication number
GB869978A
GB869978A GB5067/59A GB506759A GB869978A GB 869978 A GB869978 A GB 869978A GB 5067/59 A GB5067/59 A GB 5067/59A GB 506759 A GB506759 A GB 506759A GB 869978 A GB869978 A GB 869978A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
alkyl
alkyl groups
amides
hydrogen atoms
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
GB5067/59A
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.)
Saab Bofors AB
Original Assignee
Bofors 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 Bofors AB filed Critical Bofors AB
Publication of GB869978A publication Critical patent/GB869978A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Amides of the general formula: <FORM:0869978/IV (b)/1> (wherein R1 is an alkyl or cycloalkyl group of at most 8 carbon atoms, R2 and R3 are hydrogen atoms or alkyl groups of at most 2 carbon atoms, R2 and R3 together containing at most 3 carbon atoms, and R4, R5, R6, R7 and R8 are hydrogen atoms or alkyl groups of at most 2 carbon atoms provided that together they do not contain more than 4 carbon atoms) are prepared by reacting the corresponding pyridine carboxamides unsubstituted on the ring nitrogen atom with alkylating or cycloalkylating agents to obtain the corresponding quaternary compounds, hydrogenating the pyridine ring of these to obtain salts of the desired amides and then treating the salts with bases, e.g. sodium hydroxide, to liberate the desired free amides, which may, if desired, then be converted to other acid-addition salts. Suitable alkylating agents are dialkyl sulphates, p-toluene sulphonic acid alkyl esters and alkyl bromides or iodides, and the alkylation or cyclo alkylation is advantageously conducted at 50 to 200 DEG C. for a period of 1/2 to 20 hours. Examples are given. The process of Specification 826,668 is disclaimed. Specifications 770,129, 799,778, 799,780 and 824,542 also are referred to.ALSO:An aqueous solution, suitable for injection, contains as active ingredient an acid-addition salt of an amide of the formula <FORM:0869978/VI/1> (wherein R1 is an alkyl or cycloalkyl group of at most 8 carbon atoms, R2 and R3 are hydrogen atoms or alkyl groups of at most 2 carbon atoms, R2 and R3 together containing at most 3 carbon atoms, and R4, R5, R6, R7 and R8 are hydrogen atoms or alkyl groups of at most 2 carbon atoms provided that together they do not contain more than 4 carbon atoms). Specifications 770,129, 799,778, 799,780, 824,542 and 826,668 are referred to.
GB5067/59A 1958-03-13 1959-02-13 Method of producing n-alkyl-and-cycloalkyl-piperidine carboxylic acid amides Expired GB869978A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE869978X 1958-03-13

Publications (1)

Publication Number Publication Date
GB869978A true GB869978A (en) 1961-06-07

Family

ID=20367076

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5067/59A Expired GB869978A (en) 1958-03-13 1959-02-13 Method of producing n-alkyl-and-cycloalkyl-piperidine carboxylic acid amides

Country Status (1)

Country Link
GB (1) GB869978A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4110331A (en) 1976-06-22 1978-08-29 Ab Bofors Method of producing the hydrochloride of N-methyl piperidine-2-carboxylic acid-2,6-xylidide
US4695576A (en) * 1984-07-09 1987-09-22 Astra Lake Medel Aktiebolag L-N-n-propylpipecolic acid-2,6-xylidide
US4870086A (en) * 1986-01-03 1989-09-26 Astra Lakemedel Aktiebolag Optically pure compound and a process for its preparation
WO1995012576A1 (en) * 1993-11-04 1995-05-11 Instituto De Investigacion Y Desarrollo Quimico Biologico, S.A. New cyclopropyl derivatives, preparation method thereof and applications
US5715572A (en) * 1994-01-04 1998-02-10 Amiram Steinberg & Dalia Lapidot Hinge
US5834490A (en) * 1993-11-04 1998-11-10 Instituto De Investigacion Y Desarrolo Quimico Biologico, S.A. Cyclopropyl derivatives, preparation method there-of and applications
WO2025240895A1 (en) * 2024-05-17 2025-11-20 Siteone Therapeutics, Inc. SUBSTITUTED CYCLOALKYL AND HETEROCYCLOALKYL INHIBITORS OF NAv1.8 FOR THE TREATMENT OF PAIN

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4110331A (en) 1976-06-22 1978-08-29 Ab Bofors Method of producing the hydrochloride of N-methyl piperidine-2-carboxylic acid-2,6-xylidide
US4695576A (en) * 1984-07-09 1987-09-22 Astra Lake Medel Aktiebolag L-N-n-propylpipecolic acid-2,6-xylidide
US4870086A (en) * 1986-01-03 1989-09-26 Astra Lakemedel Aktiebolag Optically pure compound and a process for its preparation
WO1995012576A1 (en) * 1993-11-04 1995-05-11 Instituto De Investigacion Y Desarrollo Quimico Biologico, S.A. New cyclopropyl derivatives, preparation method thereof and applications
ES2082703A1 (en) * 1993-11-04 1996-03-16 Inst Investigacion Desarrollo NEW DERIVATIVES OF CYCLOPROPIL, PROCEDURES FOR ITS PREPARATION AND APPLICATIONS.
AU693123B2 (en) * 1993-11-04 1998-06-25 Instituto De Investigacion Y Desarrollo Quimico Biologico, S.A. New cyclopropyl derivatives, preparation method thereof and applications
US5834490A (en) * 1993-11-04 1998-11-10 Instituto De Investigacion Y Desarrolo Quimico Biologico, S.A. Cyclopropyl derivatives, preparation method there-of and applications
US5715572A (en) * 1994-01-04 1998-02-10 Amiram Steinberg & Dalia Lapidot Hinge
WO2025240895A1 (en) * 2024-05-17 2025-11-20 Siteone Therapeutics, Inc. SUBSTITUTED CYCLOALKYL AND HETEROCYCLOALKYL INHIBITORS OF NAv1.8 FOR THE TREATMENT OF PAIN

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