WO1995032189A1 - Intermediate for preparing a pharmaceutically active compound - Google Patents

Intermediate for preparing a pharmaceutically active compound Download PDF

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Publication number
WO1995032189A1
WO1995032189A1 PCT/US1995/005664 US9505664W WO9532189A1 WO 1995032189 A1 WO1995032189 A1 WO 1995032189A1 US 9505664 W US9505664 W US 9505664W WO 9532189 A1 WO9532189 A1 WO 9532189A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
methyl
imidazol
preparing
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.)
Ceased
Application number
PCT/US1995/005664
Other languages
English (en)
French (fr)
Inventor
Raymond E. Dagger
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.)
SmithKline Beecham Corp
Original Assignee
SmithKline Beecham Corp
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
Priority to HK98119267.9A priority Critical patent/HK1014939B/en
Priority to SI9530675T priority patent/SI0850225T1/xx
Priority to AT95919025T priority patent/ATE247091T1/de
Priority to NZ285588A priority patent/NZ285588A/en
Priority to HU9603205A priority patent/HU221905B1/hu
Priority to JP7530315A priority patent/JPH10500681A/ja
Priority to US08/737,699 priority patent/US5719293A/en
Priority to CA002190858A priority patent/CA2190858C/en
Priority to DE69531507T priority patent/DE69531507T2/de
Priority to PL95317538A priority patent/PL185858B1/pl
Priority to BR9507668A priority patent/BR9507668A/pt
Priority to EP95919025A priority patent/EP0850225B1/en
Application filed by SmithKline Beecham Corp filed Critical SmithKline Beecham Corp
Priority to AU24737/95A priority patent/AU690270B2/en
Priority to MX9605794A priority patent/MX9605794A/es
Priority to DK95919025T priority patent/DK0850225T3/da
Publication of WO1995032189A1 publication Critical patent/WO1995032189A1/en
Priority to NO964921A priority patent/NO306673B1/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

Definitions

  • the present invention relates to the bisulfite addition compound of a key intermediate useful in the preparation of an angiotensin II (All) receptor antagonist.
  • the PCT application details the preparation of 4-[(2-n-butyl-5-formyl-lH-imidazol-l-yl)methyl]benzoic acid, which is a key intermediate in the preparation of (E)-3-[2-n-butyl-l- ⁇ (4- carboxyphenyl)methyl- lH-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic acid, a highly potent All receptor antagonist (Weinstock, et al., J. Med. Chem.. 34:1514- 1517 (1991)).
  • the bisulfite addition compound itself can be used directly in the preparation of ethyl (E)-3-[2-n-butyl-l- ⁇ (4-carboxyphenyl)methyl- lH-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate, which is the immediate precussor to (E)-3-[2-n-butyl- 1- ⁇ (4-carboxyphenyl)methyl- lH-imidazol-5-yl]-2-(2- thienyl)methyl-2-propenoic acid.
  • the present invention provides for a compound according to the formula (I):
  • This invention relates to a compound of the formula (I):
  • the specific compound of this invention is the bisulfite addition compound of 4-[(2-n-butyl-5-fo ⁇ nyl-lH-imidazol-l-yl)methyl]benzoic acid, and hydrates, solvates, and salts thereof.
  • the compound of formula (I) is prepared by reacting a compound of formula (II):
  • Salts of the compound of formula (I), such as the formula (3) Scheme (I) compound may be prepared by known methods from inorganic bases, including alkali metal and alkaline earth bases, for example, lithium, sodium and potassium hydroxides, bicarbonates, and carbonates, and organic bases, such as triethylamine, butylamine, piperazine, choline and diethanolamine.
  • inorganic bases including alkali metal and alkaline earth bases, for example, lithium, sodium and potassium hydroxides, bicarbonates, and carbonates, and organic bases, such as triethylamine, butylamine, piperazine, choline and diethanolamine.
  • N-(l-iminopentyl)-4-(aminomethyl)benzoic acid 80 mMol, 19.13 g @ 80 %), 2-bromo-3-(l-methylethoxy)-2-propenal (88 mMol, 18.9 g @ 90 %), potassium carbonate (104 mMol, 14,42 g), tetrahydrofuran (90 mL) and water (10 mL) are combined, stirred vigorously and refluxed under a nitrogen atmosphere.
  • the neutralized reaction is diluted with tert-butylmethyl ether (90 mL).
  • Sodium bisulfite (20 g) and sodium chloride (16 g) are added to the well stirred mixture.
  • the mixture is cooled to 0 - 5° C, stirred for 2 hours and the intermediate sodium salt of the bisulfite addition compound (formula (3) compound in Scheme I) is isolated via vacuum filtration.
  • This intermediate salt is dissolved in water (275 mL) and the resultant solution is acidified to pH 1.0 - 1.5 with hydrochloric acid.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lining Or Joining Of Plastics Or The Like (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Lubricants (AREA)
  • Detergent Compositions (AREA)
PCT/US1995/005664 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound Ceased WO1995032189A1 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
SI9530675T SI0850225T1 (en) 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound
AT95919025T ATE247091T1 (de) 1994-05-20 1995-05-04 Zwischenprodukte zur herstellung einer pharmazeutisch aktiven verbindung
NZ285588A NZ285588A (en) 1994-05-20 1995-05-04 [2-butyl-3-(4-carboxybenzyl)-1h-imidazolium-4-yl]-hydroxymethyl sulphonate
HU9603205A HU221905B1 (hu) 1994-05-20 1995-05-04 Imidazolszármazék hidrogén-szulfit addíciós vegyülete
JP7530315A JPH10500681A (ja) 1994-05-20 1995-05-04 医薬上活性な化合物を製造するための中間体
US08/737,699 US5719293A (en) 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound
CA002190858A CA2190858C (en) 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound
PL95317538A PL185858B1 (pl) 1994-05-20 1995-05-04 Związek addycyjny kwasu 4-[(2-n-butylo-5-formylo-1Związek addycyjny kwasu 4-[(2-n-butylo-5-formylo-1H-imidazol-1-ilo)metylo]benzoesowego z wodorosiarcH-imidazol-1-ilo)metylo]benzoesowego z wodorosiarczynem i sposób jego wytwarzaniazynem i sposób jego wytwarzania
DE69531507T DE69531507T2 (de) 1994-05-20 1995-05-04 Zwischenprodukte zur herstellung einer pharmazeutisch aktiven verbindung
HK98119267.9A HK1014939B (en) 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound
EP95919025A EP0850225B1 (en) 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound
BR9507668A BR9507668A (pt) 1994-05-20 1995-05-04 Intermédio para preparar um composto farmaceuticamente atívo
AU24737/95A AU690270B2 (en) 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound
MX9605794A MX9605794A (es) 1994-05-20 1995-05-04 Intermediario para preparar un compuesto farmaceuticamente activo.
DK95919025T DK0850225T3 (da) 1994-05-20 1995-05-04 Mellemprodukt til fremstilling af en farmaceutisk aktiv forbindelse
NO964921A NO306673B1 (no) 1994-05-20 1996-11-19 Mellomprodukt for fremstilling av farmasöytisk aktiv forbindelse

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US24643194A 1994-05-20 1994-05-20
US08/246,431 1994-05-20

Publications (1)

Publication Number Publication Date
WO1995032189A1 true WO1995032189A1 (en) 1995-11-30

Family

ID=22930661

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/005664 Ceased WO1995032189A1 (en) 1994-05-20 1995-05-04 Intermediate for preparing a pharmaceutically active compound

Country Status (20)

Country Link
US (1) US5719293A (https=)
EP (1) EP0850225B1 (https=)
JP (1) JPH10500681A (https=)
KR (1) KR100369417B1 (https=)
CN (1) CN1067059C (https=)
AT (1) ATE247091T1 (https=)
AU (1) AU690270B2 (https=)
BR (1) BR9507668A (https=)
CZ (1) CZ289968B6 (https=)
DE (1) DE69531507T2 (https=)
DK (1) DK0850225T3 (https=)
ES (1) ES2204950T3 (https=)
HU (1) HU221905B1 (https=)
MX (1) MX9605794A (https=)
NO (1) NO306673B1 (https=)
NZ (1) NZ285588A (https=)
PL (1) PL185858B1 (https=)
PT (1) PT850225E (https=)
WO (1) WO1995032189A1 (https=)
ZA (1) ZA954053B (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU730383B2 (en) * 1997-02-14 2001-03-08 Smithkline Beecham Corporation Process for preparing eprosartan

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185351A (en) * 1989-06-14 1993-02-09 Smithkline Beecham Corporation Imidazolyl-alkenoic acids useful as angiotensin II receptor antagonists

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1214324A (fr) * 1957-11-16 1960-04-07 Merck Ag E Procédé de préparation du pyridoxal et de ses dérivés à groupe aldéhyde protégé
US3798172A (en) * 1969-05-26 1974-03-19 Dan River Inc Dyeing textile materials with vat and sulfur dyes and reducing agent stabilizers for same
JPS518934B2 (https=) * 1972-02-04 1976-03-22
US4024067A (en) * 1976-01-07 1977-05-17 The United States Of America As Represented By The Secretary Of The Navy Processes for the preparation of bis-benzoins and bis-benzils
JPS55104254A (en) * 1979-02-05 1980-08-09 Kuraray Co Ltd N-substituted-alpha-cyano-3-phenoxybenzylamine
JPS55167274A (en) * 1979-06-14 1980-12-26 Banyu Pharmaceut Co Ltd Forphenicine derivative and its preparation
JPS5671074A (en) * 1979-11-12 1981-06-13 Takeda Chem Ind Ltd 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative
WO1991000281A2 (en) * 1989-06-30 1991-01-10 E.I. Du Pont De Nemours And Company Fused-ring aryl substituted imidazoles
JPH03112940A (ja) * 1989-09-26 1991-05-14 Nkk Corp （±）―４―ホルミル―α―アルキルベンジルアルコール類の製造方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185351A (en) * 1989-06-14 1993-02-09 Smithkline Beecham Corporation Imidazolyl-alkenoic acids useful as angiotensin II receptor antagonists

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
J. MARC, "Advanced Organic Chemistry", Published 1992, by JOHN WILEY & SONS (N.Y.), page 895. *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU730383B2 (en) * 1997-02-14 2001-03-08 Smithkline Beecham Corporation Process for preparing eprosartan

Also Published As

Publication number Publication date
HUT75714A (en) 1997-05-28
DE69531507T2 (de) 2004-06-17
EP0850225A1 (en) 1998-07-01
PL317538A1 (en) 1997-04-14
NO964921L (no) 1996-11-20
MX9605794A (es) 1997-12-31
DE69531507D1 (de) 2003-09-18
AU2473795A (en) 1995-12-18
US5719293A (en) 1998-02-17
NO306673B1 (no) 1999-12-06
PL185858B1 (pl) 2003-08-29
BR9507668A (pt) 1997-10-07
NO964921D0 (no) 1996-11-19
CZ289968B6 (cs) 2002-05-15
ES2204950T3 (es) 2004-05-01
CZ340396A3 (en) 1997-03-12
EP0850225A4 (https=) 1998-07-01
EP0850225B1 (en) 2003-08-13
AU690270B2 (en) 1998-04-23
NZ285588A (en) 1997-12-19
CN1151734A (zh) 1997-06-11
DK0850225T3 (da) 2003-12-01
HU221905B1 (hu) 2003-02-28
ATE247091T1 (de) 2003-08-15
JPH10500681A (ja) 1998-01-20
HK1014939A1 (en) 1999-10-08
ZA954053B (en) 1996-01-19
CN1067059C (zh) 2001-06-13
KR100369417B1 (ko) 2003-04-23
HU9603205D0 (en) 1997-01-28
PT850225E (pt) 2003-11-28

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