GB991509A - Aminoalkylpiperidinoalkyl-ª‡-naphthylamines - Google Patents

Aminoalkylpiperidinoalkyl-ª‡-naphthylamines

Info

Publication number
GB991509A
GB991509A GB4072463A GB4072463A GB991509A GB 991509 A GB991509 A GB 991509A GB 4072463 A GB4072463 A GB 4072463A GB 4072463 A GB4072463 A GB 4072463A GB 991509 A GB991509 A GB 991509A
Authority
GB
United Kingdom
Prior art keywords
naphthylamine
naphthylamino
ethyl
acid
piperidine
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
GB4072463A
Inventor
Edward F Elslager
Donald F Worth
David B Capps
Leslie M Werbel
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 GB4072463A priority Critical patent/GB991509A/en
Publication of GB991509A publication Critical patent/GB991509A/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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • 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
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises a -naphthylamine compounds having the formula <FORM:0991509/C2/1> and addition salts thereof; in which x is 2 or 3, y is 0, 1, 2 or 3 and R1 and R2 independently represent lower alkyl of 1 to 3 carbon atoms inclusive or when taken together with -N< represent a heterocyclic group such as pyrrolidinyl or piperidinyl. The compounds may be made by condensing an N-(omega-haloalkyl)-1-naphthylamine of the formula <FORM:0991509/C2/2> with a dialkylaminoalkylpiperidine compound of formula <FORM:0991509/C2/3> in the presence of an acid binding agent, where Hal represents a halogen atom, preferably bromine. The reaction is preferably effected in a solvent which may be the piperidine compound in excess (which also acts as acid binding agent) or dimethyl formamide, benzene, xylene or toluene. Other suitable acid binding agents are tertiary amines, ammonium hydroxide or alkali metal hydroxides. Temperatures of above 50 DEG C. and up to 150 DEG C. are preferred. The acid addition salts are formed by reaction of the free base with an organic or inorganic acid, such as hydrochloric, hydrobromic, hydriodic, sulphuric, phosphoric, oxalic, sulphamic, lactic, tartaric, gluconic, and citric acids. Examples describe the preparation of 4-(2-diethylaminoethyl) - 1 - [2 - (1 - naphthylamino) ethyl] piperidine and its salts; 11-[2-(1-naphthylamino)ethyl] - 1,41 - ethylenedipiperidine and its hydrochloride; 11-[2-(1-naphthylamino) ethyl] - 1,21 - ethylenedipiperidine and salts; 1 - [3 - (1 - naphthylamino)propyl] - 4 - [2 - (1-pyrrolidinyl)ethyl] piperidine and 11-[2-(1-naphthylamino)ethyl] - 1,41 - dipiperidine, the preparation of other similar compounds being indicated N - (2 - bromoethyl) - 1 - naphthylamine hydrobromide is made from 1-naphthylamine and ethylene oxide to form N-(2-hydroxyethyl)-1-naphthylamine followed by reaction with hydrobromic acid. A pharmaceutical composition comprises a novel a -naphthylamine compound or acid addition salt thereof as described above in association with one or more pharmaceutical diluents and/or excipients. The composition can be made up in a dosage unit form suitable for oral administration, for example a tablet, pill, sachet, packaged powder or encapsulated powder. Specification 981,952 is referred to.
GB4072463A 1963-10-15 1963-10-15 Aminoalkylpiperidinoalkyl-ª‡-naphthylamines Expired GB991509A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4072463A GB991509A (en) 1963-10-15 1963-10-15 Aminoalkylpiperidinoalkyl-ª‡-naphthylamines

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4072463A GB991509A (en) 1963-10-15 1963-10-15 Aminoalkylpiperidinoalkyl-ª‡-naphthylamines

Publications (1)

Publication Number Publication Date
GB991509A true GB991509A (en) 1965-05-12

Family

ID=10416304

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4072463A Expired GB991509A (en) 1963-10-15 1963-10-15 Aminoalkylpiperidinoalkyl-ª‡-naphthylamines

Country Status (1)

Country Link
GB (1) GB991509A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2390434A1 (en) * 1976-06-29 1978-12-08 Rech Applications Therap STARTING COMPOUNDS FOR THE PREPARATION OF PENICILLANIC ACID DERIVATIVES
WO1994026713A1 (en) * 1993-05-17 1994-11-24 Fournier Industrie Et Sante DERIVATIVES OF β, β-DIMETHYL-4-PIPERIDINEETHANAMINE AS INHIBITORS OF THE CHOLESTEROL BIOSYNTHESIS

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2390434A1 (en) * 1976-06-29 1978-12-08 Rech Applications Therap STARTING COMPOUNDS FOR THE PREPARATION OF PENICILLANIC ACID DERIVATIVES
WO1994026713A1 (en) * 1993-05-17 1994-11-24 Fournier Industrie Et Sante DERIVATIVES OF β, β-DIMETHYL-4-PIPERIDINEETHANAMINE AS INHIBITORS OF THE CHOLESTEROL BIOSYNTHESIS
FR2705343A1 (en) * 1993-05-17 1994-11-25 Fournier Ind & Sante Derivatives of beta, beta-dimethyl-4-piperidineethanamine, process for their preparation and their use in therapy.
US5614534A (en) * 1993-05-17 1997-03-25 Fournier Industrie Et Sante Derivatives of β, β-dimethyl-4-piperidineethanamine as inhibitors of the cholesterol biosynthesis

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