CA2352520A1 - Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives - Google Patents

Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives Download PDF

Info

Publication number
CA2352520A1
CA2352520A1 CA 2352520 CA2352520A CA2352520A1 CA 2352520 A1 CA2352520 A1 CA 2352520A1 CA 2352520 CA2352520 CA 2352520 CA 2352520 A CA2352520 A CA 2352520A CA 2352520 A1 CA2352520 A1 CA 2352520A1
Authority
CA
Canada
Prior art keywords
formula
compound
see
iii
hydrogen
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.)
Granted
Application number
CA 2352520
Other languages
French (fr)
Other versions
CA2352520C (en
Inventor
Stephen E. Horne
Jaipal Reddy Nagireddy
Laura Kaye Mcconachie
Gamini Weeratunga
Bogdan M. Comanita
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.)
Apotex Pharmachem Inc
Original Assignee
Brantford Chemicals Inc
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 Brantford Chemicals Inc filed Critical Brantford Chemicals Inc
Priority to CA 2352520 priority Critical patent/CA2352520C/en
Priority to US09/902,165 priority patent/US6495691B1/en
Priority to PCT/CA2002/001017 priority patent/WO2003004502A1/en
Priority to EP02745008A priority patent/EP1404681A1/en
Publication of CA2352520A1 publication Critical patent/CA2352520A1/en
Application granted granted Critical
Publication of CA2352520C publication Critical patent/CA2352520C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

A process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives of general formula I:

(see formula I) or their pharmaceutically acceptable salts, wherein the meaning of X is hydrogen, carboxyl, alkoxycarbonyl, aryloxycarbonyl, nitrile, or carbamoyl of formula (see formula VI) wherein R, and R2 can be individually or simultaneously hydrogen, alkyl or part of a heterocyclic structure; Z can be hydrogen, halogen, alkyl, aryl, aryloxy or alkoxy group comprising the steps of:

(a) reducing the compound of formula II with suitable reducing agents to obtain compound of formula III, (see formulas II and III) (b) reacting the compound of formula III with formaldehyde or any chemical equivalent thereof to obtain compound of formula IV, (see formula IV) (c) rearranging the compound of formula IV to produce the compound of formula V, (see formula V) wherein Y is hydroxyl, alkanoyloxy, aroyloxy, carbamate or carbonate derivatives, and (d) reducing the compound of formula V to compound of formula I.
CA 2352520 2001-07-06 2001-07-06 Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives Expired - Fee Related CA2352520C (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA 2352520 CA2352520C (en) 2001-07-06 2001-07-06 Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives
US09/902,165 US6495691B1 (en) 2001-07-06 2001-07-11 Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives
PCT/CA2002/001017 WO2003004502A1 (en) 2001-07-06 2002-07-05 Process for the preparation of tetrahydrothieno [3,2-c] pyridine derivatives
EP02745008A EP1404681A1 (en) 2001-07-06 2002-07-05 Process for the preparation of tetrahydrothieno [3,2-c] pyridine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA 2352520 CA2352520C (en) 2001-07-06 2001-07-06 Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives

Publications (2)

Publication Number Publication Date
CA2352520A1 true CA2352520A1 (en) 2003-01-06
CA2352520C CA2352520C (en) 2007-10-02

Family

ID=4169420

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2352520 Expired - Fee Related CA2352520C (en) 2001-07-06 2001-07-06 Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives

Country Status (3)

Country Link
EP (1) EP1404681A1 (en)
CA (1) CA2352520C (en)
WO (1) WO2003004502A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100678287B1 (en) 2005-06-23 2007-02-02 한미약품 주식회사 Method of preparing clopidogrel and intermediates used therein
US20070191609A1 (en) * 2006-02-13 2007-08-16 Lee Pharma Limited Process for preparation of clopidogrel bisulphate form-1
PL380849A1 (en) * 2006-10-17 2008-04-28 Adamed Spółka Z Ograniczoną Odpowiedzialnością Crystalline form of racemic methyl 0 - (2-chlorophenyl) - 6, 7 - dihydrothiene [3, 2 - c] pyridil -5 (4H) - acetate, method for its manufacture and its application

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2424278A1 (en) * 1978-04-24 1979-11-23 Parcor Thieno-pyridine(s) prepn. - form hydroxy tetra:hydro thieno pyridine(s), useful as intermediates for platelet aggregation inhibitors
FR2530247B1 (en) * 1982-07-13 1986-05-16 Sanofi Sa NOVEL THIENO (3, 2-C) PYRIDINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THERAPEUTIC APPLICATION

Also Published As

Publication number Publication date
WO2003004502A1 (en) 2003-01-16
CA2352520C (en) 2007-10-02
EP1404681A1 (en) 2004-04-07

Similar Documents

Publication Publication Date Title
EP1270578A4 (en) Novel process for producing fused imidazopyridine derivative and novel crystal form
NZ515027A (en) Erythromycin derivatives as antibiotics
EP1219609A4 (en) Aromatic nitrogenous six-membered ring compounds
WO2002044153A8 (en) 4-6-diphenyl pyridine derivatives as antiinflammatory agents
NZ514662A (en) Amine derivatives
CA2340701A1 (en) Oxindole derivatives as growth hormone releasers
WO2004000762A3 (en) Propionic acid derivatives and their use as hppars activators
CA2285733A1 (en) Process for preparation of pyrazolo[4,3-d]pyrimidin-7-ones and intermediates thereof
WO2003010142A3 (en) A process for the preparation of perindopril, its analgous compounds and salts thereof using 2,5 -dioxo-oxazolidine intermediate compounds
CA2008861A1 (en) Imidazopyridazines, their production and use
MY117092A (en) Chemotherapeutic pyrrolocarbazole derivatives
EP1550651A4 (en) Glycerol derivative
CA2352520A1 (en) Process for the preparation of tetrahydrothieno[3,2-c]pyridine derivatives
CA2309474A1 (en) New 4-arylpiperidine derivatives for the treatment of pruritus
WO2001034587A3 (en) Process for preparing n-(4-hydroxy-phenyl)-n'-(4'-aminophenyl)-piperazine
CA2351528A1 (en) Process for the preparation of a piperazine derivative
CA2033937A1 (en) Hemihydrate
EP1535920A4 (en) Process for preparation of 1,3-benzodioxole-2-spiro- cycloalkane derivatives
CA2318694A1 (en) Antivirals
CA2434408A1 (en) Process for the preparation of heterocyclic indene analogs
EP1092720A3 (en) Process for the preparation of pyrazolo [4,3-d] pyrimidin-7-ones-3-pyridylsulphonyl compounds and intermediates thereof
WO2002060878A1 (en) Benzimidazolidinone derivatives
EP1227081A4 (en) Process for the preparation of oxyiminoalkanoic acid derivatives
CA2344647A1 (en) New derivatives of 6-(4-phenylbutoxy)hexylamine and process for producing salmeterol
CA2420297A1 (en) Continuous process for the preparation of pesticidal chlorothiazoles

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed