NL7908300A - Werkwijze voor de bereiding van nieuwe piperazino- -ethanol-verbindingen. - Google Patents

Werkwijze voor de bereiding van nieuwe piperazino- -ethanol-verbindingen. 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
Authority
NL
Netherlands
Prior art keywords
piperazinoethanol
compounds
preparing new
piperazine
ethoxyphenyl
Prior art date
Application number
NL7908300A
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English (en)
Original Assignee
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.)
Filing date
Publication date
Application filed by Roussel Uclaf filed Critical Roussel Uclaf
Publication of NL7908300A publication Critical patent/NL7908300A/nl

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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
    • 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)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Epidemiology (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
/-5 I
Aanvraagster: ROUSSEL UCLAF te PARIJS, FRANKRIJK
Titel :"Werkwijze voor de bereiding van nieuwe piperazino-ethanol- verbindingen".
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.
* 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.
De uitvinding zal nader toegelicht worden door de hiernavolgende voorbeelden.
VOORBEELD I : 4-(o,o'-dimethylfenyl)piperazino-ethanol.
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.
25 VOORBEELD II: 4-(m-trifluormethylfenyl)piperazino-ethanol.
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.
30 VOORBEELD III: (o-ethoxyfenyl)piperazino-ethanol.
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.
7908300 35

Claims (2)

4* - * ** --- - 2- B>x.d>E ItKT^r I-:--/ ΧΊ CONCLUSIES 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·
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. 7908300
NL7908300A 1971-06-14 1979-11-13 Werkwijze voor de bereiding van nieuwe piperazino- -ethanol-verbindingen. NL7908300A (nl)

Applications Claiming Priority (4)

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

Publications (1)

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

Family

ID=26216449

Family Applications (2)

Application Number Title Priority Date Filing Date
NLAANVRAGE7208138,A NL176072C (nl) 1971-06-14 1972-06-14 Werkwijze ter bereiding van 2-alkyl 5-thiazool-carbonzuuresters, en van een geneesmiddel met vaatverwijdende werking; gevormd geneesmiddel.
NL7908300A NL7908300A (nl) 1971-06-14 1979-11-13 Werkwijze voor de bereiding van nieuwe piperazino- -ethanol-verbindingen.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
NLAANVRAGE7208138,A NL176072C (nl) 1971-06-14 1972-06-14 Werkwijze ter bereiding van 2-alkyl 5-thiazool-carbonzuuresters, en van een geneesmiddel met vaatverwijdende werking; gevormd geneesmiddel.

Country Status (10)

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

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 (de) * 1980-01-29 1981-07-30 Hoechst Ag, 6000 Frankfurt Hydroxyphenyl-thiazol, -thiazolin und -thiazolidin-carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung zur beeinflussung des kollagenstoffwechsels
DE4339617C2 (de) * 1993-11-20 2003-06-05 Vortex Gmbh Dt Rückschlagventil für ein Brauchwasser-Zirkulationssystem
US6083966A (en) 1998-08-31 2000-07-04 University Of Florida Thiazoline acid derivatives
WO2000016763A2 (en) 1998-09-21 2000-03-30 University Of Florida Research Foundation, Inc. Antimalarial agents
WO2005034949A1 (en) 2003-09-09 2005-04-21 University Of Florida Desferrithiocin derivatives and their use as iron chelators
CA2603385C (en) 2005-04-04 2014-07-15 University Of Florida Research Foundation, Inc. Desferrithiocin polyether analogues and uses thereof for treating metal overload, oxidative stress, and neoplastic and preneoplastic conditions
CN104003955A (zh) 2007-03-15 2014-08-27 佛罗里达大学研究基金公司 去铁硫辛聚醚类似物
CN104114170B (zh) 2011-12-16 2021-07-06 佛罗里达大学研究基金会 4′-去铁硫素类似物的用途
EP3071201A4 (en) 2013-11-22 2017-04-26 University of Florida Research Foundation, Inc. Desferrithiocin analogs and uses thereof
WO2016176343A1 (en) 2015-04-27 2016-11-03 University Of Florida Research Foundation, Incorporated Metabolically programmed metal chelators 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 (nl) * 1969-12-23 1973-07-13 Ferlux

Also Published As

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

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Date Code Title Description
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