FR2326923A1 - Analgesic and hypolipemic bis-piperazinyl-ethanes - prepd. by alkylation or acylation of (1)-piperazinyl-(2)-phenyl piperazinyl ethane - Google Patents

Analgesic and hypolipemic bis-piperazinyl-ethanes - prepd. by alkylation or acylation of (1)-piperazinyl-(2)-phenyl piperazinyl ethane

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Publication number
FR2326923A1
FR2326923A1 FR7530796A FR7530796A FR2326923A1 FR 2326923 A1 FR2326923 A1 FR 2326923A1 FR 7530796 A FR7530796 A FR 7530796A FR 7530796 A FR7530796 A FR 7530796A FR 2326923 A1 FR2326923 A1 FR 2326923A1
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France
Prior art keywords
piperazinyl
ethane
phenyl
ethanes
prepd
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Granted
Application number
FR7530796A
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French (fr)
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FR2326923B1 (en
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Individual
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Individual
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Priority to FR7530796A priority Critical patent/FR2326923A1/en
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Publication of FR2326923B1 publication Critical patent/FR2326923B1/fr
Granted legal-status Critical Current

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    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • C07D295/06—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 halogen atoms or nitro radicals
    • C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • 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
    • 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
    • C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero 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
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Bis piperazinyl ethanes of formula (I) are new. (Where X is halogen, esp. Cl or F, or CF3; either A is (un)-branched 1-4C hydrocarbon; Z = CH2OH or COOR1; or A is CO; Z is alkyl, cycloalkyl, phenyl opt. substd. alkoxy, aryloxy, aralkoxy, alkylamino, anilino or cycloalkylamino; R1 = alkyl, alkenyl, alkynyl, aralkyl or benzhydryl). (I) are analgesic and hypolipemics. A typical cpd. is 1- 4-(m-trifluoromethyl phenyl)-1-piperazinyl -2- 4-(1-ethoxycarbonylethyl)-1-piperazinyl- ethane difumarate. This was prepd. by adding 2.35g. ethyl-2-bromo propionate in isopropanol to 3.42g. 1-(1-piperazinyl)-2- 4-m-trifluoromethylphenyl)-1-piperazinyl ethane, and 1.38g. K2CO3 in 10 ml. isopropanol. After refluxing for 16 hrs. the mixt. was filtered and treated with fumaric acid to give a 61% yield, m. pt. 211 degrees C.
FR7530796A 1975-10-08 1975-10-08 Analgesic and hypolipemic bis-piperazinyl-ethanes - prepd. by alkylation or acylation of (1)-piperazinyl-(2)-phenyl piperazinyl ethane Granted FR2326923A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7530796A FR2326923A1 (en) 1975-10-08 1975-10-08 Analgesic and hypolipemic bis-piperazinyl-ethanes - prepd. by alkylation or acylation of (1)-piperazinyl-(2)-phenyl piperazinyl ethane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7530796A FR2326923A1 (en) 1975-10-08 1975-10-08 Analgesic and hypolipemic bis-piperazinyl-ethanes - prepd. by alkylation or acylation of (1)-piperazinyl-(2)-phenyl piperazinyl ethane

Publications (2)

Publication Number Publication Date
FR2326923A1 true FR2326923A1 (en) 1977-05-06
FR2326923B1 FR2326923B1 (en) 1979-09-14

Family

ID=9160945

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7530796A Granted FR2326923A1 (en) 1975-10-08 1975-10-08 Analgesic and hypolipemic bis-piperazinyl-ethanes - prepd. by alkylation or acylation of (1)-piperazinyl-(2)-phenyl piperazinyl ethane

Country Status (1)

Country Link
FR (1) FR2326923A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0042162A2 (en) * 1980-06-13 1981-12-23 Chugai Seiyaku Kabushiki Kaisha Compositions for treating diseases in circulatory organs
US4820707A (en) * 1986-07-09 1989-04-11 Adir Et Cie 2,6-piperazinedione compounds
CN114478359A (en) * 2022-03-17 2022-05-13 河南大学 Carbamate TRPV1 antagonistic/FAAH inhibition double-target medicine and preparation method and application thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0042162A2 (en) * 1980-06-13 1981-12-23 Chugai Seiyaku Kabushiki Kaisha Compositions for treating diseases in circulatory organs
EP0042162A3 (en) * 1980-06-13 1982-03-10 Chugai Seiyaku Kabushiki Kaisha Compositions for treating diseases in circulatory organs
US4820707A (en) * 1986-07-09 1989-04-11 Adir Et Cie 2,6-piperazinedione compounds
CN114478359A (en) * 2022-03-17 2022-05-13 河南大学 Carbamate TRPV1 antagonistic/FAAH inhibition double-target medicine and preparation method and application thereof
CN114478359B (en) * 2022-03-17 2023-09-29 河南大学 Carbamate TRPV1 antagonism/FAAH inhibition double-target drug, and preparation method and application thereof

Also Published As

Publication number Publication date
FR2326923B1 (en) 1979-09-14

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