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WO1997017050A3 - An improved method for preparation of substituted tetrahydroisoquinolines - Google Patents

An improved method for preparation of substituted tetrahydroisoquinolines Download PDF

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Publication number
WO1997017050A3
WO1997017050A3 PCT/US1996/017926 US9617926W WO9717050A3 WO 1997017050 A3 WO1997017050 A3 WO 1997017050A3 US 9617926 W US9617926 W US 9617926W WO 9717050 A3 WO9717050 A3 WO 9717050A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
improved method
substituted tetrahydroisoquinolines
optically pure
pure
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/US1996/017926
Other languages
French (fr)
Other versions
WO1997017050A2 (en
Inventor
Brian Griffin
Mark R Johnson
Ronald L Keller
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.)
Monsanto Co
Original Assignee
Monsanto Co
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 Monsanto Co filed Critical Monsanto Co
Priority to AU77244/96A priority Critical patent/AU7724496A/en
Publication of WO1997017050A2 publication Critical patent/WO1997017050A2/en
Publication of WO1997017050A3 publication Critical patent/WO1997017050A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

An improved method for the preparation and isolation of optically pure (3S) or (3R)-1, 2, 3, 4-tetrahydroisoquinoline-3-carboxylic acid comprises reacting formaldehyde with either D- or L-phenylalanine and hydrobromic acid to prepare the pure hydrobromide salts. The mixture is then cooled to precipitate the optically pure isomer which is filtered and then neutralized with a base to form the free acid and dried.
PCT/US1996/017926 1995-11-09 1996-11-08 An improved method for preparation of substituted tetrahydroisoquinolines Ceased WO1997017050A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU77244/96A AU7724496A (en) 1995-11-09 1996-11-08 An improved method for preparation of substituted tetrahydroisoquinolines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55624995A 1995-11-09 1995-11-09
US08/556,249 1995-11-09

Publications (2)

Publication Number Publication Date
WO1997017050A2 WO1997017050A2 (en) 1997-05-15
WO1997017050A3 true WO1997017050A3 (en) 1997-06-05

Family

ID=24220534

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/017926 Ceased WO1997017050A2 (en) 1995-11-09 1996-11-08 An improved method for preparation of substituted tetrahydroisoquinolines

Country Status (2)

Country Link
AU (1) AU7724496A (en)
WO (1) WO1997017050A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1283640B1 (en) * 1996-07-29 1998-04-23 Archimica Spa PROCEDURE FOR THE PREPARATION OF AN OPTICALLY PURE TETRAHYDROQUINOLINCARBOXYL ACID

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0039804A1 (en) * 1980-05-12 1981-11-18 Usv Pharmaceutical Corporation Cyclic amides
EP0496369A1 (en) * 1991-01-24 1992-07-29 Hoechst Aktiengesellschaft Process for the preparation of racemic and optically active-1,2,3,4-tetrahydro isoquinoline 3-carboxylic acid and its precursors
EP0533000A1 (en) * 1991-09-18 1993-03-24 F.Hoffmann-La Roche & Co. Aktiengesellschaft Process for the preparation of 3-substituted 1,2,3,4-tetrahydro isoquinoline derivatives
EP0578163A1 (en) * 1992-07-09 1994-01-12 Hoechst Aktiengesellschaft Process for the preparation of D,L or D,L-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0039804A1 (en) * 1980-05-12 1981-11-18 Usv Pharmaceutical Corporation Cyclic amides
EP0496369A1 (en) * 1991-01-24 1992-07-29 Hoechst Aktiengesellschaft Process for the preparation of racemic and optically active-1,2,3,4-tetrahydro isoquinoline 3-carboxylic acid and its precursors
EP0533000A1 (en) * 1991-09-18 1993-03-24 F.Hoffmann-La Roche & Co. Aktiengesellschaft Process for the preparation of 3-substituted 1,2,3,4-tetrahydro isoquinoline derivatives
EP0578163A1 (en) * 1992-07-09 1994-01-12 Hoechst Aktiengesellschaft Process for the preparation of D,L or D,L-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
ARCHER,S.: "A Revised Preparation of Clemo's Tetrahydrobenzoquinolizinone", J.ORG.CHEM., vol. 16, 1951, WASHINGTON, pages 430 - 432, XP000651831 *
GRUNEWLAD,G.L. ET AL.: "Synthesis and Evaluation of 3-Substituted Analogues of 1,2,3,4-Tetrahydroquinoline as Inhibitors of Phenyletanolamine N-Methyltransferase", J.MED.CHEM., vol. 31, no. 4, 1988, WASHINGTON, pages 824 - 830, XP002027200 *
HAYASHI,K. ET AL.: "Facile Preparation of optically Pure (3S)- and (3R-)1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid", CHEM.PHARM.BULL., vol. 31, no. 1, 1983, TOKYO, pages 312 - 314, XP002027201 *
KAMMERMEIER,B.O.T. ET AL.: "Efficient Sythesis of Racemic and Enantiomerically Pure 1,2,3,4-Tetrahydroisoquinolline-3-carboxylic Acid and Esters", SYNTHESIS, November 1992 (1992-11-01), STUTTGART, pages 1157 - 1160, XP002027198 *
SHINAKI,H. ET AL.: "N-Acylphenylalanines and Related Compounds. A New Class of Oral Hypoglycemic Agents", J.MED.CHEM., vol. 31, 1988, WASHINGTON, pages 2092 - 2097, XP002027199 *
SHIRAIWA,T. ET AL.: "Asymetric Transformation of (RS)-1,2,3,4-Tetrahydro-3-sioquinolinecarboxylic Acid via Salt Formation with (1S)-10-Camphersulfonic Acid", BULL.CHEM.SOC.JPN., vol. 64, 1991, TOKYO, pages 3729 - 3731, XP002027197 *

Also Published As

Publication number Publication date
WO1997017050A2 (en) 1997-05-15
AU7724496A (en) 1997-05-29

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