GB1016968A - Piperazine esters of ª‡-substituted 1-naphthylacetic acids - Google Patents

Piperazine esters of ª‡-substituted 1-naphthylacetic acids

Info

Publication number
GB1016968A
GB1016968A GB17604/64A GB1760464A GB1016968A GB 1016968 A GB1016968 A GB 1016968A GB 17604/64 A GB17604/64 A GB 17604/64A GB 1760464 A GB1760464 A GB 1760464A GB 1016968 A GB1016968 A GB 1016968A
Authority
GB
United Kingdom
Prior art keywords
piperazine
substituted
reacting
propanediol
unsubstituted
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
GB17604/64A
Inventor
Gianfranco Pala
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
Priority to NL124129D priority Critical patent/NL124129C/xx
Application filed by Instituto de Angeli SpA filed Critical Instituto de Angeli SpA
Priority to GB17604/64A priority patent/GB1016968A/en
Priority to BR164391/64A priority patent/BR6464391D0/en
Priority to US412859A priority patent/US3338902A/en
Priority to IL22496A priority patent/IL22496A/en
Priority to DE19641445959 priority patent/DE1445959A1/en
Priority to FR996522A priority patent/FR4374M/fr
Priority to NL6413857A priority patent/NL6413857A/xx
Priority to FR996526A priority patent/FR1476516A/en
Priority to ES0306519A priority patent/ES306519A1/en
Priority to BE656442D priority patent/BE656442A/xx
Priority to CH1540964A priority patent/CH448099A/en
Priority to AT1011864A priority patent/AT254197B/en
Publication of GB1016968A publication Critical patent/GB1016968A/en
Priority to CH1047969A priority patent/CH541567A/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

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (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.
GB17604/64A 1964-04-28 1964-04-28 Piperazine esters of ª‡-substituted 1-naphthylacetic acids Expired GB1016968A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
NL124129D NL124129C (en) 1964-04-28
GB17604/64A GB1016968A (en) 1964-04-28 1964-04-28 Piperazine esters of ª‡-substituted 1-naphthylacetic acids
BR164391/64A BR6464391D0 (en) 1964-04-28 1964-11-17 PROCESS FOR THE PREPARATION OF NEW I-NAFTYLACETIC ESTERS OF DIETANOL PIPERAZINE
US412859A US3338902A (en) 1964-04-28 1964-11-20 Esters of piperazine 1, 4-diethanol
IL22496A IL22496A (en) 1964-04-28 1964-11-23 N,n1-di-(beta-hydroxyethyl)piperazine esters of 1-naphthyl alkanoic acids
NL6413857A NL6413857A (en) 1964-04-28 1964-11-27
FR996522A FR4374M (en) 1964-04-28 1964-11-27
DE19641445959 DE1445959A1 (en) 1964-04-28 1964-11-27 Process for the preparation of piperazine derivatives
FR996526A FR1476516A (en) 1964-04-28 1964-11-27 New nude esters. nu-di (beta-hydroxyethyl) piperazine and process for their preparation
ES0306519A ES306519A1 (en) 1964-04-28 1964-11-28 Esters of piperazine 1, 4-diethanol
BE656442D BE656442A (en) 1964-04-28 1964-11-30
CH1540964A CH448099A (en) 1964-04-28 1964-11-30 Process for the preparation of 1-naphthyl-acetic acid esters of N, N'-di- (B-hydroxyethyl) piperazine
AT1011864A AT254197B (en) 1964-04-28 1964-11-30 Process for the preparation of new diesters of N, N'-di (β-hydroxyethyl) piperazine with optionally α-substituted 1-naphthylacetic acids
CH1047969A CH541567A (en) 1964-04-28 1969-07-09 1,4-bis(hydroxyethyl)piperazine diesters - with myolytic-type spasmolytic activity

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
GB1016968A true GB1016968A (en) 1966-01-12

Family

ID=10098067

Family Applications (1)

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

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
CH448099A (en) 1967-12-15
IL22496A (en) 1968-12-26
AT254197B (en) 1967-05-10
ES306519A1 (en) 1965-04-01
BR6464391D0 (en) 1973-08-07
US3338902A (en) 1967-08-29
BE656442A (en) 1965-05-31
FR4374M (en) 1966-08-29

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