NL7908300A - METHOD FOR PREPARING NEW PIPERAZINO-ETHANOL COMPOUNDS. - Google Patents

METHOD FOR PREPARING NEW PIPERAZINO-ETHANOL COMPOUNDS. Download PDF

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Publication number
NL7908300A
NL7908300A NL7908300A NL7908300A NL7908300A NL 7908300 A NL7908300 A NL 7908300A NL 7908300 A NL7908300 A NL 7908300A NL 7908300 A NL7908300 A NL 7908300A NL 7908300 A NL7908300 A NL 7908300A
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NL
Netherlands
Prior art keywords
piperazinoethanol
compounds
preparing new
piperazine
ethoxyphenyl
Prior art date
Application number
NL7908300A
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Dutch (nl)
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Roussel Uclaf
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.)
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Publication date
Application filed by Roussel Uclaf filed Critical Roussel Uclaf
Publication of NL7908300A publication Critical patent/NL7908300A/en

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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
    • C07D295/04—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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

"* --793472/vdV/Ar j-b-XdJSÊ. -j"* --793472 / vdV / Ar j-b-XdJSÊ. -J

/-5 I/ -5 I

Aanvraagster: ROUSSEL UCLAF te PARIJS, FRANKRIJKApplicant: ROUSSEL UCLAF in PARIS, FRANCE

Titel :"Werkwijze voor de bereiding van nieuwe piperazino-ethanol- verbindingen".Title: "Process for the preparation of new piperazinoethanol compounds".

5 De uitvinding heeft betrekking op een werkwijze voor de be reiding van nieuwe piperazino-ethanolverbindingen, die toegepast kunnen worden als uitgangsverbindingen voor de bereiding van 2-alkylthiazol 5-carbonzuuresters met adrenolytische en perifere vasodilatatiewerking, die beschreven zijn in de Nederlandse octrooiaanvrage no. 7?·θ8ΐ3δ, waaruit de 10 onderhavige aanvrage is afgesplitst.The invention relates to a process for the preparation of new piperazinoethanol compounds, which can be used as starting compounds for the preparation of 2-alkylthiazole 5-carboxylic acid esters with adrenolytic and peripheral vasodilatation action, which are described in Dutch patent application no. 7 ? · Θ8ΐ3δ, from which the present 10 application has been split off.

* De nieuwe piperazino-ethanolverbindingen zijn ^-(o-ethoxy- fenyl)piperazino-ethanol, k-(0,0·’— dimethylfenyl)piperazino-ethanol en k-(m-trifluormethylfenyl)piperazino-ethanol, en kuróien bereid worden op voor analoge verbindingen bekende wijze, bijvoorbeeld door inwerking van ethy-15 leenoxyde op overeenkomstig gesubstitueerde piperazinen.* The new piperazinoethanol compounds are ^ - (o-ethoxyphenyl) piperazinoethanol, k- (0,0'-dimethylphenyl) piperazinoethanol and k- (m-trifluoromethylphenyl) piperazinoethanol, and are prepared in a manner known for analogous compounds, for example by action of ethylene oxide on correspondingly substituted piperazines.

De uitvinding zal nader toegelicht worden door de hiernavolgende voorbeelden.The invention will be further elucidated by the following examples.

VOORBEELD I : 4-(o,o'-dimethylfenyl)piperazino-ethanol.EXAMPLE I: 4- (o, o'-dimethylphenyl) piperazinoethanol.

Aan een oplossing van 1^,3 g N-(2,6-dimethylfenyl)piperazine 20 in 38 cm''* methanol voegt men bij -15°C, cm^ van een methanolische oplossing van ethyleenoxyde toe, die 200 g ethyleenoxyde per liter bevat, laat 90 uren staan, destilleert het oplosmiddel onder verminderde druk af, rectificeert het residu en verkrijgt 1^,67 g **-(0,0'-dimethylfenyl)piperazino-ethanol met een kookpunt van 1^6°C onder 0,05 mm kwikdruk.To a solution of 1.3 g of N- (2,6-dimethylphenyl) piperazine 20 in 38 cm 3 of methanol is added at -15 ° C, cm 2 of a methanolic solution of ethylene oxide containing 200 g of ethylene oxide per liter, let stand for 90 hours, distill off the solvent under reduced pressure, rectify the residue and obtain 1 ^ 67 g ** - (0,0'-dimethylphenyl) piperazinoethanol with a boiling point of 1 ^ 6 ° C 0.05 mm mercury pressure.

25 VOORBEELD II: 4-(m-trifluormethylfenyl)piperazino-ethanol.EXAMPLE II: 4- (m-trifluoromethylphenyl) piperazinoethanol.

Op analoge wijze als in Voorbeeld I, verkrijgt men uitgaande van 17,3 g N-(m-trifluormethylfenyl)piperazine, 15,8 g ^-(m-trifluormethylfenyl·) piperazino-ethanol met een kookpunt van 143°C onder een druk van 0,1 mm kwikdruk.In an analogous manner as in Example 1, 17.3 g of N- (m-trifluoromethylphenyl) piperazine, 15.8 g of (m-trifluoromethylphenyl) piperazinoethanol having a boiling point of 143 ° C under pressure are obtained starting from of 0.1 mm mercury pressure.

30 VOORBEELD III: (o-ethoxyfenyl)piperazino-ethanol.EXAMPLE III: (o-ethoxyphenyl) piperazinoethanol.

Op analoge wijze als in Voorbeeld I verkrijgt men uitgaande van 10,3 g N-(o-ethoxyfenyl)piperazine 7,9 g 4-(o-ethoxyfenyl)piperazino-ethanol met een kookpunt van 148°C onder 0,1 mm kwikdruk.Analogously as in Example 1, 7.9 g of 4- (o-ethoxyphenyl) piperazinoethanol having a boiling point of 148 ° C under 0.1 mm of mercury pressure are obtained from 10.3 g of N- (o-ethoxyphenyl) piperazine. .

7908300 357908300 35

Claims (2)

4* - * ** --- - 2- B>x.d>E ItKT^r I-:--/ ΧΊ CONCLUSIES IX4 * - * ** --- - 2- B> x.d> E ItKT ^ r I -: - / ΧΊ CONCLUSIONS IX 1. Werkwijze voor de bereiding van piperazino-ethanolverbindingen, met het kenmerk, dat men ^-(o-ethoxyfenyl)piperazino-ethanol, 5 4-( o To ’ -dimethylfenyl)piperazino-ethanol en k~ (m-trifluormethylfenyl) pipers - zino-ethanol bereidt op voor analoge verbindingen bekende wijze·1. Process for the preparation of piperazinoethanol compounds, characterized in that 1 - (o-ethoxyphenyl) piperazinoethanol, 4- (o To '-dimethylphenyl) piperazinoethanol and k- (m-trifluoromethylphenyl) pipers - Zino-ethanol prepared in a manner known for analogous compounds 2. Werkwijze volgens conclusie 1,met het kenmerk, dat men ethyleenoxyde laat inwerken op N-(o-ethoxyfenyl)piperazine, ^-(ο,ο'- 10 dimethylfenyl)piperazine of *f-(m-trifluormethylfenyl)piperazine. 79083002. Process according to claim 1, characterized in that ethylene oxide is allowed to act on N- (o-ethoxyphenyl) piperazine, ^ - (ο, ο'-dimethylphenyl) piperazine or * f- (m-trifluoromethylphenyl) piperazine. 7908300
NL7908300A 1971-06-14 1979-11-13 METHOD FOR PREPARING NEW PIPERAZINO-ETHANOL COMPOUNDS. NL7908300A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR7121466 1971-06-14
FR7121466A FR2141526B1 (en) 1971-06-14 1971-06-14
FR7306847A FR2247243B2 (en) 1971-06-14 1973-02-27
FR7306847 1973-02-27

Publications (1)

Publication Number Publication Date
NL7908300A true NL7908300A (en) 1980-03-31

Family

ID=26216449

Family Applications (2)

Application Number Title Priority Date Filing Date
NLAANVRAGE7208138,A NL176072C (en) 1971-06-14 1972-06-14 PROCESS FOR THE PREPARATION OF 2-ALKYL 5-THIAZOLIC CARBONIC ACID ESTERS, AND A MEDICINAL PRODUCT WITH DEVASTATIC ACTION; FORMED MEDICINAL PRODUCT.
NL7908300A NL7908300A (en) 1971-06-14 1979-11-13 METHOD FOR PREPARING NEW PIPERAZINO-ETHANOL COMPOUNDS.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
NLAANVRAGE7208138,A NL176072C (en) 1971-06-14 1972-06-14 PROCESS FOR THE PREPARATION OF 2-ALKYL 5-THIAZOLIC CARBONIC ACID ESTERS, AND A MEDICINAL PRODUCT WITH DEVASTATIC ACTION; FORMED MEDICINAL PRODUCT.

Country Status (10)

Country Link
US (1) US3853875A (en)
JP (1) JPS5519251A (en)
AT (1) AT317895B (en)
BE (1) BE784777A (en)
CA (1) CA1001629A (en)
CH (1) CH555362A (en)
FR (2) FR2141526B1 (en)
GB (1) GB1382887A (en)
NL (2) NL176072C (en)
SE (1) SE389673B (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4411900A (en) * 1980-01-03 1983-10-25 Fujisawa Pharmaceutical Co., Ltd. Benzhydrylpiperozinyl thiazole derivatives and pharmaceutical composition comprising the same
DE3002989A1 (en) * 1980-01-29 1981-07-30 Hoechst Ag, 6000 Frankfurt HYDROXYPHENYL-THIAZOLE, -THIAZOLINE AND -THIAZOLIDINE-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR INFLUENCING COLLAGEN METABOLISM
DE4339617C2 (en) * 1993-11-20 2003-06-05 Vortex Gmbh Dt Check valve for a domestic water circulation system
US6083966A (en) 1998-08-31 2000-07-04 University Of Florida Thiazoline acid derivatives
NZ526880A (en) 1998-09-21 2005-05-27 Univ Florida Antimalarial agents
WO2005034949A1 (en) 2003-09-09 2005-04-21 University Of Florida Desferrithiocin derivatives and their use as iron chelators
PL1866296T3 (en) 2005-04-04 2017-05-31 University Of Florida Research Foundation, Inc. Desferrithiocin polyether analogues
CA2680592C (en) 2007-03-15 2016-07-05 University Of Florida Research Foundation, Inc. Desferrithiocin polyether analogues and uses thereof in treating pathological conditions
US20140343110A1 (en) 2011-12-16 2014-11-20 University Of Florida Research Foundation, Inc. Uses of 4'-desferrithiocin analogs
CA2930966A1 (en) 2013-11-22 2015-05-28 University Of Florida Research Foundation, Inc. Desferrithiocin analogs and uses thereof
KR20170140306A (en) 2015-04-27 2017-12-20 유니버시티 오브 플로리다 리서치 파운데이션, 인코포레이티드 Metabolically programmed metal chelating agents and uses thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3238203A (en) * 1962-10-12 1966-03-01 Olin Mathieson Basic esters of n-alkenoylanthranilic acid
FR2073284B1 (en) * 1969-12-23 1973-07-13 Ferlux

Also Published As

Publication number Publication date
NL176072C (en) 1985-02-18
NL176072B (en) 1984-09-17
GB1382887A (en) 1975-02-05
FR2141526B1 (en) 1975-05-30
BE784777A (en) 1972-12-13
DE2228805B2 (en) 1977-03-31
NL7208138A (en) 1972-12-18
FR2141526A1 (en) 1973-01-26
DE2228805A1 (en) 1972-12-21
SE389673B (en) 1976-11-15
CH555362A (en) 1974-10-31
US3853875A (en) 1974-12-10
CA1001629A (en) 1976-12-14
JPS5519251A (en) 1980-02-09
FR2247243B2 (en) 1976-12-03
AT317895B (en) 1974-09-25
FR2247243A2 (en) 1975-05-09

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A1B A search report has been drawn up
BC A request for examination has been filed
A85 Still pending on 85-01-01
BN A decision not to publish the application has become irrevocable