ES306519A1 - Esters of piperazine 1, 4-diethanol - Google Patents

Esters of piperazine 1, 4-diethanol

Info

Publication number
ES306519A1
ES306519A1 ES0306519A ES306519A ES306519A1 ES 306519 A1 ES306519 A1 ES 306519A1 ES 0306519 A ES0306519 A ES 0306519A ES 306519 A ES306519 A ES 306519A ES 306519 A1 ES306519 A1 ES 306519A1
Authority
ES
Spain
Prior art keywords
piperazine
reacting
propanediol
unsubstituted
methoxy
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
ES0306519A
Other languages
Spanish (es)
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.)
Instituto de Angeli SpA
Original Assignee
Instituto de Angeli SpA
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 Instituto de Angeli SpA filed Critical Instituto de Angeli SpA
Publication of ES306519A1 publication Critical patent/ES306519A1/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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds of general formula <FORM:1016968/C2/1> where R is hydrogen or C1 to C5 alkyl group and acid addition salts thereof and the preparation thereof by reacting a piperazine derivative of the formu'a <FORM:1016968/C2/2> with a 1-naphthylacetic acid derivative of the formula <FORM:1016968/C2/3> where X and Y represent groups which are able to react together to form divalent -O-CH2-CH2-radicals, for example (1) reacting an acid halide of an a -substituted or unsubstituted 1-naphthyl acetic acid with N,N1-d -(b -hydroxyethyl)-piperazine (2) reacting a b -halo ethyl ester of an a -substituted or unsubstituted 1-naphthyl acetic acid with piperazine (3) transesterifying the esters, preferably the alkyl esters, of a -substituted or unsubstituted 1-naphthyl acetic acids with N,N1-di-(b -hydroxyethyl)-piperazine and (4) reacting an alkali metal salt of an a -substituted or unsubstituted 1-naphthyl acetic acid with an N,N1-di-(b -haloethyl)piperazine. The compounds of the invention may be mixed with solubility promoters such as metamizole, urea, nicotinamide, nicotinamide ascorbate, piperazine, hexamethylene - tetramine, antipyrene, acetamide, dimethylacetamide, coramine, and compounds containing a -O-CH2-CH(OH-CH2OH group such as 3 - (2 - methoxy - phenoxy) - 1,2 - propanediol and 3-(2-methyl, chloro- and methoxy-4-propionyl - phenoxy) - 1,2 - propanediol. Acid chlorides of the general formula <FORM:1016968/C2/4> wherein R is H, ethyl, n-propyl or n-butyl, are produced by reacting the corresponding free carboxylic acids and thionyl chloride.ALSO:Pharmaceutical compositions having spasmolytic activity contain as their active ingredient compounds of the formula: <FORM:1016968/A5-A6/1> wherein, R represents hydrogen or straight chain C1 to C5 alkyl, and acid addition salts thereof. The compositions which may be adapted for oral, rectal or parenteral administration take the form of tablets, dragees, capsules, suppositories, ampoules, suspensions, syrups, solutions, injectable liquids, linctuses, emulsions, drops or suspensions. Solubility promoters such as metamizole, urea, nicotinamide, nicotinamide ascorbate, piperazine, hexamethylene-tetramine, antipyrene, acetamide, dimethylacetamide coramine and compounds containing a -O-CH2-CH(OH)-CH2OH group such as 3-(2-methoxy-pheroxy)-1, 2-propanediol and 3-(2-methyl, chloro and methoxy-4-propionyl-phenoxy)-1, 2-propanediol may be included.
ES0306519A 1964-04-28 1964-11-28 Esters of piperazine 1, 4-diethanol Expired ES306519A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB17604/64A GB1016968A (en) 1964-04-28 1964-04-28 Piperazine esters of ª‡-substituted 1-naphthylacetic acids

Publications (1)

Publication Number Publication Date
ES306519A1 true ES306519A1 (en) 1965-04-01

Family

ID=10098067

Family Applications (1)

Application Number Title Priority Date Filing Date
ES0306519A Expired ES306519A1 (en) 1964-04-28 1964-11-28 Esters of piperazine 1, 4-diethanol

Country Status (9)

Country Link
US (1) US3338902A (en)
AT (1) AT254197B (en)
BE (1) BE656442A (en)
BR (1) BR6464391D0 (en)
CH (1) CH448099A (en)
ES (1) ES306519A1 (en)
FR (1) FR4374M (en)
GB (1) GB1016968A (en)
IL (1) IL22496A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2996506A (en) * 1961-08-15 Hcxchb
US2995554A (en) * 1958-09-08 1961-08-08 Lakeside Lab Inc Substituted glycolic acid esters of 1, 4-bis-(hydroxyalkyl)-piperazines

Also Published As

Publication number Publication date
BR6464391D0 (en) 1973-08-07
FR4374M (en) 1966-08-29
BE656442A (en) 1965-05-31
AT254197B (en) 1967-05-10
CH448099A (en) 1967-12-15
IL22496A (en) 1968-12-26
GB1016968A (en) 1966-01-12
US3338902A (en) 1967-08-29

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Legal Events

Date Code Title Description
FD1A Patent lapsed

Effective date: 19850226