FR2254324A1 - 1-Amino-3-amino-propan-2-ols - with antiinflammatory, analgesic, beta-blocking alpha-blocking tranquillizing activity - Google Patents

1-Amino-3-amino-propan-2-ols - with antiinflammatory, analgesic, beta-blocking alpha-blocking tranquillizing activity

Info

Publication number
FR2254324A1
FR2254324A1 FR7441556A FR7441556A FR2254324A1 FR 2254324 A1 FR2254324 A1 FR 2254324A1 FR 7441556 A FR7441556 A FR 7441556A FR 7441556 A FR7441556 A FR 7441556A FR 2254324 A1 FR2254324 A1 FR 2254324A1
Authority
FR
France
Prior art keywords
amino
blocking
ch2ch2oh
cyclohexyl
ols
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.)
Granted
Application number
FR7441556A
Other languages
French (fr)
Other versions
FR2254324B1 (en
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.)
Especialidades Latinas Medicamentos Universales SA
Original Assignee
Especialidades Latinas Medicamentos Universales SA
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 Especialidades Latinas Medicamentos Universales SA filed Critical Especialidades Latinas Medicamentos Universales SA
Publication of FR2254324A1 publication Critical patent/FR2254324A1/en
Application granted granted Critical
Publication of FR2254324B1 publication Critical patent/FR2254324B1/fr
Granted 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
    • 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
    • C07D211/40—Oxygen atoms
    • C07D211/42—Oxygen atoms attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1-Thymoxy-3-aminopropan-2-ols (I) are prepd. by first treating thymol with epichlorhydrin in presence of a catalyst at 70 to 100 degrees C for 10-20 hrs. to give 3-chloro-2-hydroxy-1-thymoxypropane, then treating the reaction mixt. with NaOH or KOH for 24 hrs., extracting the mixt. with CHCl3 evapg. the extract under reduced pressure and distilling the residue under reduced pressure. The glycidyl ether obtd. is dissolved in (m)ethanol or THF and treated with the appropriate amine HNR1R2. Specific values of R1 and R2 are: when R1 is H, R2 is -CH2CH2Ph, -CH2CH2NH2, -CHPh2, -CHPh-CH2Ph, -CH2CH2.NMe2, -CH2CH2.OMe, -CHMe2CH2OH, -CH2CHOHMe, cyclohexyl, -CHMeCH2CH2-CH2CH2CH3, -CH2CH2CH2-NMe2 or R-isopropylphenyl when R1 is Me, R2 is -CH2CH2OH, or cyclohexyl; when R1 is -CH2CH2OH, R2 is -CMe3, -CH2.Ph; when R1 is Pri, R2 is Pri; when R1 is cyclohexyl, R2 is R1 or Ph; when R1 is -CH2.CH.CH2, R2 is -CH2. CH:CH2; when R1 is Et, R2 is -CH2CH2OH; or R1 and R2 together are The cpds. are spasmolytics, and alpha- and beta-blockers, potentiators of adrenaline, antiserotonins, antihistamines, tranquillisers, antiinflammatories and analgesics.
FR7441556A 1973-12-17 1974-12-17 1-Amino-3-amino-propan-2-ols - with antiinflammatory, analgesic, beta-blocking alpha-blocking tranquillizing activity Granted FR2254324A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES421546A ES421546A1 (en) 1973-12-17 1973-12-17 Procedure for obtaining pharmacologically active 1-timoxi-2-propanol-amines. (Machine-translation by Google Translate, not legally binding)

Publications (2)

Publication Number Publication Date
FR2254324A1 true FR2254324A1 (en) 1975-07-11
FR2254324B1 FR2254324B1 (en) 1978-07-28

Family

ID=8465584

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7441556A Granted FR2254324A1 (en) 1973-12-17 1974-12-17 1-Amino-3-amino-propan-2-ols - with antiinflammatory, analgesic, beta-blocking alpha-blocking tranquillizing activity

Country Status (2)

Country Link
ES (1) ES421546A1 (en)
FR (1) FR2254324A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5541204A (en) * 1994-12-02 1996-07-30 Bristol-Myers Squibb Company Aryloxypropanolamine β 3 adrenergic agonists

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5541204A (en) * 1994-12-02 1996-07-30 Bristol-Myers Squibb Company Aryloxypropanolamine β 3 adrenergic agonists
US5723489A (en) * 1994-12-02 1998-03-03 Bristol-Myers Squibb Company Aryloxypropanolamine beta 3 adrenergic agonists

Also Published As

Publication number Publication date
ES421546A1 (en) 1976-04-01
FR2254324B1 (en) 1978-07-28

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Legal Events

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ST Notification of lapse