WO1979000023A1 - A novel process for preparation of a therapeutically active pyridine compound - Google Patents
A novel process for preparation of a therapeutically active pyridine compound Download PDFInfo
- Publication number
- WO1979000023A1 WO1979000023A1 PCT/SE1978/000009 SE7800009W WO7900023A1 WO 1979000023 A1 WO1979000023 A1 WO 1979000023A1 SE 7800009 W SE7800009 W SE 7800009W WO 7900023 A1 WO7900023 A1 WO 7900023A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- preparation
- therapeutically active
- compound
- formula
- novel process
- Prior art date
Links
- 0 [O-][N+](c1ccccc1)c1cc*cc1 Chemical compound [O-][N+](c1ccccc1)c1cc*cc1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
Definitions
- the present invention is related to a novel process for pre- paration of a therapeutically active compound.
- An object of the invention is to provide a process enabling improved economy of production and avoiding use of chemicals that are difficult to handle.
- Swedish Patent 361 663 discloses i . a . a compound of the formu la
- the main disadvantages of the known method is that the pre ⁇ paration of the intermediate is complicated, involving chemicals which are difficult to handle, such as butyl lithi and that only a low overall yield may be obtained.
- Ph denotes phenyl and R denotes CH- or H, and reacted with 4-bromophenyl-3-pyridylketcne in the presence of sodium methylate according to the following scheme:
- the last reaction is suitably carried out in a solvent such as dimethylforma ide, hexamethylphosphorus-triamide or di- methylsulfoxide.
- a solvent such as dimethylforma ide, hexamethylphosphorus-triamide or di- methylsulfoxide.
- the new manner of preparing the Wittig re agent has surprisingly been found to be operable and is technically advantageous.
- a further advantage of the new process is that the simple reactant sodium methylate may be used as a base instead of butyl ' -lithium often used in simil reactions.
- Butyl lithium is, as mentioned, difficult to handle and should if possible be avoided in production on a technical scale because of its strong reactivity, which i.a may lead to self-ignition.
- the therapeutically active end compound VI exists in two stereoisomeric forms, a Z-form and an E-form according to t IUPAC nomenclature.
- the preferred isomer is the Z-isomer, having the configuration
- the preferred isomer may be obtained by isolation from an isom ⁇ ric mixture of the end compound VI..
- a modified manner of preparing the end compound is along t reaction route:.
- R represents methyl or hydrogen
- X is a leaving group selected from the halogens suc as Cl or Br methylsulfonyl and toluenesulfonyl, introduced reacting the compound of formula IV with a halogenating age such as HC1, HBr, PBr 3 , PClg, S0C1 , PCI or methylsulfonic toluenesulfonic acids and wherein R is as defined above.
- the compound and the methods of the invention are useful in the pharmaceutical industry, especially in preparation of a compound of formula VI above in a technical scale.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE7707707A SE409861B (sv) | 1977-07-04 | 1977-07-04 | Ett nytt forfarande for framstellning av en terapeutisk aktiv pyridinforening |
SE7707707 | 1977-07-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1979000023A1 true WO1979000023A1 (en) | 1979-01-25 |
Family
ID=20331764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SE1978/000009 WO1979000023A1 (en) | 1977-07-04 | 1978-06-26 | A novel process for preparation of a therapeutically active pyridine compound |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS5414976A (ru) |
AT (1) | AT365171B (ru) |
CA (1) | CA1082198A (ru) |
CH (1) | CH641163A5 (ru) |
DK (1) | DK295378A (ru) |
ES (1) | ES471302A1 (ru) |
FI (1) | FI64581C (ru) |
IT (1) | IT1105226B (ru) |
NL (1) | NL7807246A (ru) |
NO (1) | NO782304L (ru) |
SE (1) | SE409861B (ru) |
SU (1) | SU923366A3 (ru) |
WO (1) | WO1979000023A1 (ru) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0081478A2 (en) * | 1979-11-16 | 1983-06-15 | Astra Läkemedel Aktiebolag | Novel halophenyl-pyridyl-allylamine derivatives, processes and intermediates as well as pharmaceutical preparations thereof |
US20120217101A1 (en) * | 2009-10-23 | 2012-08-30 | Kone Corporation | Elevator arrangement and method |
US20120291395A1 (en) * | 2009-12-31 | 2012-11-22 | Kone Corporation | Method in the manufacture of an elevator |
US20130118838A1 (en) * | 2010-05-28 | 2013-05-16 | Kone Corporation | Method and elevator arrangement |
US20130233655A1 (en) * | 2012-03-06 | 2013-09-12 | Kone Corporation | Method and an elevator arrangement |
US20130248299A1 (en) * | 2010-12-01 | 2013-09-26 | Kone Corporation | Elevator arrangement and method |
US9388020B2 (en) * | 2012-03-06 | 2016-07-12 | Kone Corporation | Method and an elevator arrangement |
-
1977
- 1977-07-04 SE SE7707707A patent/SE409861B/sv unknown
-
1978
- 1978-06-26 CH CH329979A patent/CH641163A5/de not_active IP Right Cessation
- 1978-06-26 WO PCT/SE1978/000009 patent/WO1979000023A1/en unknown
- 1978-06-27 CA CA306,260A patent/CA1082198A/en not_active Expired
- 1978-06-29 DK DK782953A patent/DK295378A/da not_active Application Discontinuation
- 1978-06-30 IT IT50123/78A patent/IT1105226B/it active
- 1978-06-30 FI FI782115A patent/FI64581C/fi not_active IP Right Cessation
- 1978-06-30 ES ES471302A patent/ES471302A1/es not_active Expired
- 1978-07-03 NO NO782304A patent/NO782304L/no unknown
- 1978-07-04 AT AT0483778A patent/AT365171B/de not_active IP Right Cessation
- 1978-07-04 NL NL7807246A patent/NL7807246A/xx not_active Application Discontinuation
- 1978-07-04 JP JP8182078A patent/JPS5414976A/ja active Pending
-
1979
- 1979-08-03 SU SU792798502A patent/SU923366A3/ru active
Non-Patent Citations (1)
Title |
---|
ORGANIC REACTIONS 1965 (Wiley & Sons, New York) vol 14, p. 319-321, 334, 388-398 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0081478A2 (en) * | 1979-11-16 | 1983-06-15 | Astra Läkemedel Aktiebolag | Novel halophenyl-pyridyl-allylamine derivatives, processes and intermediates as well as pharmaceutical preparations thereof |
EP0081478A3 (en) * | 1979-11-16 | 1984-01-04 | Astra Lakemedel Aktiebolag | Novel halophenyl-pyridyl-allylamine derivatives, processes and intermediates as well as pharmaceutical preparations thereof |
US20120217101A1 (en) * | 2009-10-23 | 2012-08-30 | Kone Corporation | Elevator arrangement and method |
US20120291395A1 (en) * | 2009-12-31 | 2012-11-22 | Kone Corporation | Method in the manufacture of an elevator |
US20130118838A1 (en) * | 2010-05-28 | 2013-05-16 | Kone Corporation | Method and elevator arrangement |
US20130248299A1 (en) * | 2010-12-01 | 2013-09-26 | Kone Corporation | Elevator arrangement and method |
US20130233655A1 (en) * | 2012-03-06 | 2013-09-12 | Kone Corporation | Method and an elevator arrangement |
US9388020B2 (en) * | 2012-03-06 | 2016-07-12 | Kone Corporation | Method and an elevator arrangement |
Also Published As
Publication number | Publication date |
---|---|
FI782115A (fi) | 1979-01-05 |
AT365171B (de) | 1981-12-28 |
IT1105226B (it) | 1985-10-28 |
ES471302A1 (es) | 1979-09-01 |
DK295378A (da) | 1979-01-05 |
FI64581C (fi) | 1983-12-12 |
NL7807246A (nl) | 1979-01-08 |
SE7707707L (sv) | 1979-01-05 |
IT7850123A0 (it) | 1978-06-30 |
NO782304L (no) | 1979-01-05 |
JPS5414976A (en) | 1979-02-03 |
ATA483778A (de) | 1981-05-15 |
FI64581B (fi) | 1983-08-31 |
CH641163A5 (de) | 1984-02-15 |
SE409861B (sv) | 1979-09-10 |
SU923366A3 (ru) | 1982-04-23 |
CA1082198A (en) | 1980-07-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO314456B1 (no) | Fremgangsmåter og mellomprodukter nyttige for å fremstille antifolater | |
EP1954134A2 (en) | Process for synthesizing 2-phenyl-1h-phenantrho[9,10-d]imidazole derivative | |
WO1979000023A1 (en) | A novel process for preparation of a therapeutically active pyridine compound | |
KR101583851B1 (ko) | 3-메틸-2-티오펜카르복실산의 제조 방법 | |
EP2982673B1 (en) | Process for manufacturing 5-chloromethyl-2,3-dicarboxylic anhydride | |
US20220002241A1 (en) | Process for the preparation of arylsulfonylpropenenitriles | |
JP2672874B2 (ja) | シトシンの製法 | |
JP3003946B2 (ja) | 置換エテンの調製 | |
JPH01168675A (ja) | 1,3−ジアルキルピラゾール−5−カルボン酸エステル類の製造法 | |
EP1002788A1 (en) | Process for preparing halogenated phenylmalonates | |
CA1119179A (en) | Process for preparing n-tritylimidazole compounds | |
US9303022B2 (en) | Industrial method for the preparation of high-purity methiozolin | |
JP2648297B2 (ja) | カルボジチオアート誘導体の製造方法 | |
US10807962B2 (en) | Process for the synthesis of firocoxib | |
GB2132607A (en) | Preparation of thiophene compounds | |
JP3545466B2 (ja) | ジヒドロクロマンカルボン酸類及びその製造方法 | |
CN118146160A (zh) | 砜吡草唑及其中间体的制备方法和应用 | |
JPH11209354A (ja) | 3,5−ジメチルイソオキサゾール−4−スルホニルクロライドを製造する方法 | |
KR970006237B1 (ko) | 피라졸을 함유한 프로페노익 에스테르 유도체의 제조방법 | |
HU193454B (en) | Process for producing 3-phenyl-butyraldehyde derivatives | |
CN117529325A (zh) | 制备7-(吗啉基)-2-(N-哌嗪基)甲基噻吩并[2,3-c]吡啶衍生物的改进方法 | |
JPS624272A (ja) | 5−置換チオピラゾ−ル誘導体 | |
JPS59130278A (ja) | 2−アルキルチオメチル−4−ヒドロキシピリミジンの製造方法 | |
JPH054987A (ja) | ピラゾロピリジン誘導体の製造法 | |
JPWO2010029756A1 (ja) | 5−[2−(メチルチオ)エトキシ]ピリミジン−2−アミンの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): CH SE SU Designated state(s): CH SE SU |