EP0000301A1 - Verfahren zur Herstellung von Thieno(2,3-c) und Thieno(3,2-c) Pyridinen - Google Patents

Verfahren zur Herstellung von Thieno(2,3-c) und Thieno(3,2-c) Pyridinen Download PDF

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Publication number
EP0000301A1
EP0000301A1 EP78400018A EP78400018A EP0000301A1 EP 0000301 A1 EP0000301 A1 EP 0000301A1 EP 78400018 A EP78400018 A EP 78400018A EP 78400018 A EP78400018 A EP 78400018A EP 0000301 A1 EP0000301 A1 EP 0000301A1
Authority
EP
European Patent Office
Prior art keywords
acid
process according
formula
reaction
thieno
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
EP78400018A
Other languages
English (en)
French (fr)
Other versions
EP0000301B1 (de
Inventor
Jean-Pierre Maffrand
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.)
Parcor SARL
Sanofi SA
Original Assignee
Parcor SARL
Sanofi SA
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 Parcor SARL, Sanofi SA filed Critical Parcor SARL
Publication of EP0000301A1 publication Critical patent/EP0000301A1/de
Application granted granted Critical
Publication of EP0000301B1 publication Critical patent/EP0000301B1/de
Expired legal-status Critical Current

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Classifications

    • 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

Definitions

  • the present invention relates to a new process for the preparation of thieno [2,3-c] and thieno [3,2-c] pyridines of formula: in which R represents hydrogen or the carboxy group.
  • R represents hydrogen or the carboxy group.
  • the object of the present invention is to provide an inexpensive synthesis process making it possible to obtain, with good yields, the compounds (I) and (II) which are important intermediates in the chemical and pharmaceutical industry, in particular for the preparation of thienopyridine derivatives having various therapeutic activities, for example anti-inflammatory, anti-platelet aggregation, anti-arrhythmic, etc. (see for example the patents and published French patent applications No. 2 215 948, 2.257 271, 2,315,274 and 2,345,150.
  • the process of the invention is characterized in that a compound of formula is reacted with nitrous acid, thus obtaining compounds of formula and then we remove the nitroso group from the compounds of mule (V) or (VI) either by reaction with an acid, thus obtaining the derivatives of formula (I) or (II) in which R is hydrogen, or by reaction with an alkali metal hydroxide and subsequent neutralization, obtaining thus the derivatives of formula (I) or (II) in which R is the carboxy group.
  • nitrous acid is formed in situ by reacting an alkali metal nitrite in aqueous solution with an acid.
  • the reaction is carried out in particular by slowly adding an aqueous solution of alkali metal nitrite, in particular sodium, to a hydrochloric solution, maintained at 0 ° -15 ° C, of the derivative of formula (III) or (IV) and then abandoning several hours at room temperature.
  • alkali metal nitrite in particular sodium
  • a mineral acid such as hydrochloric acid, hydrobromic acid or sulfuric acid, preferably hydrochloric acid
  • an organic acid such as trifluoroacetic acid or trichloroacetic acid, preferably trifluoroacetic acid
  • the starting compounds of formula (III) or (IV) can be prepared by reaction of a compound of formula with formaldehyde in aqueous solution, in the presence of a strong acid.
  • Example 3 By operating as in Example 3, starting from the nitrose compound obtained in Example 1, thieno [2,3-c] pyridine is obtained. F 50 ° C, yield: 47%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
EP78400018A 1977-06-21 1978-06-13 Verfahren zur Herstellung von Thieno(2,3-c) und Thieno(3,2-c) Pyridinen Expired EP0000301B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR7718991A FR2395271A1 (fr) 1977-06-21 1977-06-21 Procede de preparation de thieno (2,3-c) et thieno (3,2-c) pyridines
FR7718991 1977-06-21

Publications (2)

Publication Number Publication Date
EP0000301A1 true EP0000301A1 (de) 1979-01-10
EP0000301B1 EP0000301B1 (de) 1980-09-17

Family

ID=9192350

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78400018A Expired EP0000301B1 (de) 1977-06-21 1978-06-13 Verfahren zur Herstellung von Thieno(2,3-c) und Thieno(3,2-c) Pyridinen

Country Status (31)

Country Link
US (1) US4161599A (de)
EP (1) EP0000301B1 (de)
JP (1) JPS549298A (de)
AR (1) AR216515A1 (de)
AT (1) AT362372B (de)
AU (1) AU515505B2 (de)
BE (1) BE868272A (de)
CA (1) CA1074800A (de)
CH (1) CH635588A5 (de)
DD (1) DD135492A5 (de)
DE (1) DE2860164D1 (de)
DK (1) DK147827C (de)
ES (1) ES469703A1 (de)
FI (1) FI63236C (de)
FR (1) FR2395271A1 (de)
GB (1) GB1584143A (de)
GR (1) GR64843B (de)
HU (1) HU178316B (de)
IE (1) IE47055B1 (de)
IL (1) IL54780A (de)
IT (1) IT1105427B (de)
LU (1) LU79787A1 (de)
MX (1) MX5020E (de)
NO (1) NO149315C (de)
NZ (1) NZ187625A (de)
PH (1) PH17024A (de)
PL (1) PL113510B1 (de)
PT (1) PT68182A (de)
SU (1) SU728717A3 (de)
YU (1) YU40709B (de)
ZA (1) ZA783051B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE816390A (en) * 1973-06-15 1974-12-16 Vinyl or ethynyl-substd. mercapto-methyl pyridines - for treatment of rheumatoid arthritis and inflammatory troubles
JPS6171830A (ja) * 1984-09-17 1986-04-12 Dainippon Ink & Chem Inc 界面活性剤組成物
US5962490A (en) * 1987-09-25 1999-10-05 Texas Biotechnology Corporation Thienyl-, furyl- and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin
AU8074894A (en) * 1994-02-02 1995-08-21 Eli Lilly And Company Hiv protease inhibitors and intermediates
US5958905A (en) 1996-03-26 1999-09-28 Texas Biotechnology Corporation Phosphoramidates, phosphinic amides and related compounds and the use thereof to modulate the activity of endothelin
US5804585A (en) * 1996-04-15 1998-09-08 Texas Biotechnology Corporation Thieno-pyridine sulfonamides derivatives thereof and related compounds that modulate the activity of endothelin
FR2797874B1 (fr) * 1999-08-27 2002-03-29 Adir Nouveaux derives de la pyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2312498A1 (fr) * 1975-05-30 1976-12-24 Parcor Procede de preparation de la thieno (3,2-c) pyridine et de derives de celle-ci

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2345150A2 (fr) * 1975-08-06 1977-10-21 Centre Etd Ind Pharma Nouveaux derives de la thienopyridine, et leur application
US3997545A (en) * 1973-07-23 1976-12-14 Takeda Chemical Industries, Ltd. Thienopyridine-carboxylic acid derivatives
FR2263745B1 (de) * 1974-03-12 1977-12-02 Roussel Uclaf
FR2278683A1 (fr) * 1974-07-16 1976-02-13 Parcor Procede de preparation de la thieno(3,2-c)pyridine et de la thieno(2,3-c)pyridine
FR2312247A1 (fr) * 1975-05-30 1976-12-24 Parcor Derives de la thieno-pyridine, leur procede de preparation et leurs applications
FR2315274A1 (fr) * 1975-06-27 1977-01-21 Parcor Nouveaux derives de la thieno (2,3-c) pyridine, leur preparation et leurs applications

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2312498A1 (fr) * 1975-05-30 1976-12-24 Parcor Procede de preparation de la thieno (3,2-c) pyridine et de derives de celle-ci

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 47, 1297-98 (1974). *

Also Published As

Publication number Publication date
NO149315B (no) 1983-12-19
DD135492A5 (de) 1979-05-09
PL207770A1 (pl) 1979-05-07
ES469703A1 (es) 1978-12-16
PL113510B1 (en) 1980-12-31
MX5020E (es) 1983-02-22
FI781900A (fi) 1978-12-22
JPS6230192B2 (de) 1987-07-01
FI63236C (fi) 1983-05-10
HU178316B (en) 1982-04-28
AU3725578A (en) 1980-01-03
BE868272A (fr) 1978-12-20
IT7849919A0 (it) 1978-06-19
AT362372B (de) 1981-05-11
CA1074800A (en) 1980-04-01
FR2395271A1 (fr) 1979-01-19
IL54780A0 (en) 1978-07-31
GR64843B (en) 1980-06-04
IL54780A (en) 1981-01-30
DK147827C (da) 1985-06-10
PT68182A (fr) 1978-07-01
DK147827B (da) 1984-12-17
NO782147L (no) 1978-12-22
NZ187625A (en) 1980-11-28
EP0000301B1 (de) 1980-09-17
DK266978A (da) 1978-12-22
GB1584143A (en) 1981-02-04
FR2395271B1 (de) 1980-04-04
SU728717A3 (ru) 1980-04-15
FI63236B (fi) 1983-01-31
ZA783051B (en) 1979-06-27
NO149315C (no) 1984-03-28
YU135878A (en) 1982-10-31
PH17024A (en) 1984-05-11
US4161599A (en) 1979-07-17
AU515505B2 (en) 1981-04-09
AR216515A1 (es) 1979-12-28
IT1105427B (it) 1985-11-04
IE47055B1 (en) 1983-12-14
YU40709B (en) 1986-04-30
IE781023L (en) 1978-12-21
ATA337978A (de) 1980-10-15
CH635588A5 (fr) 1983-04-15
DE2860164D1 (en) 1980-12-18
JPS549298A (en) 1979-01-24
LU79787A1 (fr) 1978-11-28

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