FI90232B - Förfarande för framställning av terapeutiskt aktiva imidazoliumföreningar - Google Patents

Förfarande för framställning av terapeutiskt aktiva imidazoliumföreningar Download PDF

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Publication number
FI90232B
FI90232B FI842760A FI842760A FI90232B FI 90232 B FI90232 B FI 90232B FI 842760 A FI842760 A FI 842760A FI 842760 A FI842760 A FI 842760A FI 90232 B FI90232 B FI 90232B
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Finland
Prior art keywords
butyl
compound
mol
chloride
mixture
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FI842760A
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English (en)
Finnish (fi)
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FI842760A0 (sv
FI842760A (sv
FI90232C (sv
Inventor
Julius Diamond
Jr William Carl Lumma
Jr Thomas Kenneth Morgan
Ronald Andre Wohl
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Schering Ag
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Publication of FI842760A publication Critical patent/FI842760A/sv
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • 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
    • A61P9/06—Antiarrhythmics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
    • C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
    • C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
    • C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
    • C07C33/483—Monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/50—Halogenated unsaturated alcohols containing six-membered aromatic rings and other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Cardiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Gas Separation By Absorption (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)

Claims (6)

1. FÖrfarande för framstälining av terapeutiskt aktiva imidazoliumföreningar med formeln (I) 5 R,_Ri R5
10. R, väri R är en oförgrenad eller förgrenad alkyl med 1-12 kolatomer, eller cykloalkyl(lägre)alkyl,
15 R,, R2 och R3 är samma eller olika och vardera är väte eller en oförgrenad alkylgrupp med 1-4 kolatomer, R4 och R5 är samma eller olika och vardera är väte, halogen, lägre alkyl, lägre alkoxi, lägre alkanoylamido eller lägre alkylsulfonylamino, 20 n är 0 - 2, “ p är 0 - 5, Y är metylen, hydroximetylen, -CH=CH-, karbonyl, -NHS02-eller -S02NH-, förutsatt att: 2 5 (a) di Y är -S02NH- eller -NHS02-, sä är p ett heitä 1 2 - 5, (b) dä Y är metylen eller -CH=CH-, sä är p är ett heltal 1-5, (c) dä summan av kolatomer i kedjan -(CH2)„-Y-(CH2)p- är 2, 30 sä kan R4 och R5 ej vardera vara väteatomer, (d) dä Y är karbonyl, sä kan R, och R5 ej vardera vara väteatomer; och ΊΓ är halogenid, tosylat, sulfat, divätefosfat eller me-tansulfonat, 35 molekylföreningar bildade av ovan anförda kvaternära sait 45 90232 och aromatiska dikarboxylsyror, kännetecknat därav, att A) en förening med formeln J^)- (CHj)n-Y-(CH2)p-Ql R5 omsätts med en förening med formeln 10 R2 Ri R3 15 väri R|, R2 och R3 betecknar saroina som ovan, och den er-hällna föreningen omsätts med en förening med formeln RZ eller RQ,, 20 eller B) en förening med formeln RQi 25 omsätts med en förening med formeln }=<
30 HN N R3 och den erhällna föreningen omsätts med en förening med formeln 46 90232 ^J^-<cH2)n-V- (CH2)p-Ql 5 varvid Q, i förfaranden A) och B) är en avgäende grupp som är halogen, mesyloxi eller tosyloxi, och ifall den genom förfarande A) eller B) erhällna föreningen ej inne-häller en grupp Z, omsätts den med en syra vars anjon är 10 Z", och om s§l önskas, omvandlas ett erhället salt till ett annat salt och/eller omvandlas en karbonylgrupp Y till en grupp CHOH genom hydrering i närvaro av en Pd/C-katalysator.
2. Förfarande enligt patentkravet 1, känne-15 tecknat därav, att man framställer 1-(4-[4-(ace- tylamino)fenyl]butyl]-3-heptylimidazolium-(4-metylben-sen)sulfonat.
3. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer 1-[4-(4-klorfe- 20 nyl)butyl]-3-propylimidazoliumdivätefosfat.
4. Förfarande enligt patentkravet 1, kanne-tecknat därav, att man framställer i-[4-(4-fluor-fenyl)butyl]-3-heptylimidazoliumdivätefosfat.
5. Förfarande enligt patentkravet 1, kanne-25 tecknat därav, att man framställer 1-[4-(4-klorfe- ny1)butyl]-3-pentylimidazoliumdivätefosfat.
6. Förfarande enligt patentkravet 1, känne-tecknat därav, att man framställer l-butyl-3-[4- (4-klorfenyl)butyl]imidazoliumdivätefosfat.
FI842760A 1983-07-12 1984-07-10 Förfarande för framställning av terapeutiskt aktiva imidazoliumföreningar FI90232C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US51314383 1983-07-12
US06/513,143 US4581370A (en) 1983-07-12 1983-07-12 Antiarrhythmic imidazoliums

Publications (4)

Publication Number Publication Date
FI842760A0 FI842760A0 (sv) 1984-07-10
FI842760A FI842760A (sv) 1985-01-13
FI90232B true FI90232B (sv) 1993-09-30
FI90232C FI90232C (sv) 1994-01-10

Family

ID=24042059

Family Applications (1)

Application Number Title Priority Date Filing Date
FI842760A FI90232C (sv) 1983-07-12 1984-07-10 Förfarande för framställning av terapeutiskt aktiva imidazoliumföreningar

Country Status (15)

Country Link
US (2) US4581370A (sv)
EP (1) EP0131302B1 (sv)
JP (1) JPH08815B2 (sv)
AT (1) ATE72238T1 (sv)
AU (1) AU582538B2 (sv)
CA (1) CA1289563C (sv)
DE (1) DE3485488D1 (sv)
DK (1) DK339184A (sv)
FI (1) FI90232C (sv)
GR (1) GR82282B (sv)
IE (1) IE59337B1 (sv)
IL (1) IL72354A (sv)
NO (1) NO168300C (sv)
NZ (1) NZ208831A (sv)
ZA (1) ZA845410B (sv)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0149976A3 (de) * 1983-12-30 1986-12-10 Ciba-Geigy Ag Substituierte Imidazole
US4609670A (en) * 1984-11-13 1986-09-02 Eli Lilly And Company Imidazolium hypoglycemic agents
DE3674054D1 (de) * 1985-04-26 1990-10-18 Hoffmann La Roche 1,3-disubstituierte imidazoliumsalze.
US4937250A (en) * 1988-03-07 1990-06-26 Ciba-Geigy Corporation Alpha-heterocycle substituted tolunitriles
US4978672A (en) * 1986-03-07 1990-12-18 Ciba-Geigy Corporation Alpha-heterocyclc substituted tolunitriles
GB8609331D0 (en) * 1986-04-16 1986-05-21 Pfizer Ltd Anti-arrythmia agents
GB8707120D0 (en) * 1987-03-25 1987-04-29 Pfizer Ltd Antiarrhythmic agents
DE3876006T2 (de) * 1987-04-14 1993-03-25 Glaxo Group Ltd Keton-derivate.
GB8720693D0 (en) * 1987-09-03 1987-10-07 Glaxo Group Ltd Chemical compounds
HU221317B1 (en) * 1991-08-14 2002-09-28 Procter & Gamble Pharma 2,4-imidazolidinedione derivatives and antiarrhythmic and antifibrillatory compositions containing them, and process for producing them
RU2142461C1 (ru) * 1991-08-14 1999-12-10 Проктер энд Гэмбл Фармасьютикалз, Инк. Циклические соединения мочевины, фармацевтическая композиция и способ лечения
BR9206353A (pt) * 1991-08-14 1995-11-07 Procter & Gamble Pharma Uretanos cíclicos utilizáveis como agentes antiarrítmicos e antifibrilatórios
US5635521A (en) * 1991-09-23 1997-06-03 Sandoz Ltd. Imidazolylmethyl-pyridines
WO1993012108A1 (en) * 1991-12-18 1993-06-24 Schering Corporation Imidazolyl or imidazoylalkyl substituted with a four or five membered nitrogen containing heterocyclic ring
GB9127304D0 (en) * 1991-12-23 1992-02-19 Boots Co Plc Therapeutic agents
US5183813A (en) * 1992-02-19 1993-02-02 Sterling Winthrop Inc. Antiarrhythmic agents
US6031109A (en) * 1993-06-22 2000-02-29 Knoll Aktiengesellschaft Phenoxy-, phenylthio-, benzoyl-alkyleneaminoalkylene-imidazole derivatives as therapeutic agents
GB9312893D0 (en) * 1993-06-22 1993-08-04 Boots Co Plc Therapeutic agents
FR2766179B1 (fr) * 1997-07-16 2000-03-17 Oreal Nouvelles bases d'oxydation cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture
FR2766178B1 (fr) * 1997-07-16 2000-03-17 Oreal Nouvelles bases d'oxydation cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture
FR2782718B1 (fr) * 1998-09-02 2000-11-10 Oreal Nouveaux composes cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture
FR2782719B1 (fr) * 1998-09-02 2000-11-10 Oreal Nouvelles orthophenylenediamines cationiques, leur utilisation pour la teinture d'oxydation des fibres keratiniques, compositions tinctoriales et procedes de teinture
JP4620286B2 (ja) * 2001-06-05 2011-01-26 富士フイルム株式会社 電解質組成物、光電変換素子及び光電気化学電池
CN1659131A (zh) 2002-04-08 2005-08-24 葛兰素集团有限公司 2－((2－烷氧基)－苯基)－环戊－1－烯基)芳香碳－以及杂环羧酸及其衍生物
GB0225548D0 (en) 2002-11-01 2002-12-11 Glaxo Group Ltd Compounds
JP2008133248A (ja) * 2006-10-24 2008-06-12 Sanyo Chem Ind Ltd イミダゾリウム塩の製造方法

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US2493318A (en) * 1945-07-14 1950-01-03 Lilly Co Eli Imidazolium compounds
FR8357M (sv) * 1966-09-08 1971-02-08
SE7600674L (sv) * 1975-02-05 1976-08-06 Rohm & Haas Fungicider
DE2510525C3 (de) * 1975-03-11 1978-03-30 Th. Goldschmidt Ag, 4300 Essen Quartäre 2-Alkylimidazoliumsalze
JPS5488268A (en) * 1977-10-19 1979-07-13 Wellcome Found Novel imidazole derivatives*their manufacture and medical composition
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Also Published As

Publication number Publication date
EP0131302A2 (en) 1985-01-16
NO168300B (no) 1991-10-28
AU3054384A (en) 1985-01-17
US4689341A (en) 1987-08-25
FI842760A0 (sv) 1984-07-10
IL72354A (en) 1988-11-30
IE59337B1 (en) 1994-02-09
ZA845410B (en) 1985-02-27
FI842760A (sv) 1985-01-13
CA1289563C (en) 1991-09-24
IL72354A0 (en) 1984-11-30
DK339184D0 (da) 1984-07-10
IE841774L (en) 1985-01-12
AU582538B2 (en) 1989-04-06
GR82282B (sv) 1984-12-13
JPS6038366A (ja) 1985-02-27
US4581370A (en) 1986-04-08
JPH08815B2 (ja) 1996-01-10
DE3485488D1 (de) 1992-03-12
DK339184A (da) 1985-01-13
EP0131302A3 (en) 1987-06-16
NO842835L (no) 1985-01-14
FI90232C (sv) 1994-01-10
NO168300C (no) 1992-02-05
NZ208831A (en) 1988-09-29
ATE72238T1 (de) 1992-02-15
EP0131302B1 (en) 1992-01-29

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