AU3926389A - An improved process for the preparation of n,n'-bis- (alkoxyalkyl)-pyridine-2,4-dicarboxamides - Google Patents
An improved process for the preparation of n,n'-bis- (alkoxyalkyl)-pyridine-2,4-dicarboxamidesInfo
- Publication number
- AU3926389A AU3926389A AU39263/89A AU3926389A AU3926389A AU 3926389 A AU3926389 A AU 3926389A AU 39263/89 A AU39263/89 A AU 39263/89A AU 3926389 A AU3926389 A AU 3926389A AU 3926389 A AU3926389 A AU 3926389A
- Authority
- AU
- Australia
- Prior art keywords
- solution prepared
- pyridine
- alkoxyalkyl
- bis
- preparation
- 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
Links
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
- C07D213/40—Acylated substituent nitrogen atom
-
- 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
- C07D213/60—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 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Transplantation (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention relates to a process for the preparation of N,N'-bis(alkoxyalkyl)diamides of pyridine-2,4-dicarboxylic acid, and to the use of these compounds for preparing drugs for oral administration. The process according to the invention yields the compounds of the formula I <IMAGE> in which R<1> is C1-C4-alkyl which is monosubstituted with C1-C4-alkoxy, by initially A) reacting pyridine-2,4-dicarboxylic acid in toluene with a 2-3-fold excess of SOCl2 at temperatures of 90-110 DEG C, dissolving the resulting intermediate in dioxane and B) mixing 4 times the molar amount of alkoxyalkylamine of the formula II H2N-(R<2>)-OR<3> (II) in which R<2> is C1-C4-alkylene and R<3> is C1-C4-alkyl with dioxane, and subsequently, at a temperature of -5 to +5 DEG C, either adding the solution prepared as in A) dropwise to the solution prepared as in B), or adding the solution prepared as in B) dropwise to the solution prepared as in A), and then allowing reaction to continue at room temperature.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3826471A DE3826471A1 (en) | 1988-08-04 | 1988-08-04 | Improved process for the preparation of N,N'-bis(alkoxyalkyl)pyridine-2,4-dicarboximides |
DE3826471 | 1988-08-04 | ||
DE3828140 | 1988-08-19 | ||
DE3828140A DE3828140A1 (en) | 1988-08-19 | 1988-08-19 | Improved process for the preparation of N,N'-bis(alkoxyalkyl)pyridine-2,4-dicarboxamides and use of these compounds for the preparation of orally administrable medicaments |
Publications (2)
Publication Number | Publication Date |
---|---|
AU3926389A true AU3926389A (en) | 1990-02-08 |
AU615324B2 AU615324B2 (en) | 1991-09-26 |
Family
ID=25870814
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU39263/89A Ceased AU615324B2 (en) | 1988-08-04 | 1989-08-03 | An improved process for the preparation of n,n'-bis- (alkoxyalkyl)-pyridine-2,4-dicarboxamides |
Country Status (13)
Country | Link |
---|---|
EP (1) | EP0353668B1 (en) |
JP (1) | JP2683423B2 (en) |
KR (1) | KR0137789B1 (en) |
AT (1) | ATE113036T1 (en) |
AU (1) | AU615324B2 (en) |
CA (1) | CA1330802C (en) |
DE (1) | DE58908519D1 (en) |
DK (1) | DK170748B1 (en) |
ES (1) | ES2065355T3 (en) |
HU (1) | HU208423B (en) |
IE (1) | IE64673B1 (en) |
IL (1) | IL91185A (en) |
PT (1) | PT91361B (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU599746B2 (en) * | 1987-02-10 | 1990-07-26 | Hoechst Aktiengesellschaft | Pyridine-2,4- and -2,5-dicarboxylic acid amides, processes for their preparation, the use thereof, and medicaments based on these compounds |
AU600084B2 (en) * | 1987-02-10 | 1990-08-02 | Hoechst Aktiengesellschaft | Pyridine-2,4- and -2,5-dicarboxylic acid derivatives, processes for their preparation, the use thereof and medicaments based on these compounds |
AU604293B2 (en) * | 1987-02-10 | 1990-12-13 | Hoechst Aktiengesellschaft | Pyridine-2,4- and 2,5-dicarboxylic acid derivatives, a process for their preparation, the use thereof, and medicaments based on these compounds |
US5482953A (en) * | 1991-02-05 | 1996-01-09 | Hoechst Aktiengesellschaft | 2,4-and 2,5-bistetrazolylpyridines and the use thereof as pharmaceuticals |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3707429A1 (en) * | 1987-03-07 | 1988-09-15 | Hoechst Ag | SUBSTITUTED PYRIDINE-2,4-DICARBONIC ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF, USE OF THE SAME AND MEDICINAL PRODUCTS BASED ON THESE COMPOUNDS |
DE3924093A1 (en) * | 1989-07-20 | 1991-02-07 | Hoechst Ag | N, N'-BIS (ALKOXY-ALKYL) -PYRIDINE-2,4-DICARBONESAUREDIAMIDES, METHOD FOR THE PRODUCTION AND USE THEREOF |
DE4031000A1 (en) * | 1990-10-01 | 1992-04-09 | Hoechst Ag | 4- OR 5-SUBSTITUTED PYRIDINE-2-CARBONIC ACIDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A MEDICINAL PRODUCT |
TW199147B (en) * | 1991-03-18 | 1993-02-01 | Hoechst Ag | |
EP0533130A1 (en) * | 1991-09-19 | 1993-03-24 | Hoechst Aktiengesellschaft | 2-Hydroxymethylpyridines, the corresponding pyridine-N-oxides and derivatives thereof, process for their preparation and their use |
EP0541042A1 (en) * | 1991-11-05 | 1993-05-12 | Hoechst Aktiengesellschaft | 2,4- and 2,5-pyridine-dicarboxylic acid derivatives, process for their preparation and their use |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1235348A (en) * | 1968-12-16 | 1971-06-09 | Dufour Claude | Pyridine carboxylic acid amides |
DE3703959A1 (en) * | 1987-02-10 | 1988-08-18 | Hoechst Ag | PYRIDINE-2,4- AND 2,5-DICARBONIC ACID AMIDES, METHOD FOR THE PRODUCTION THEREOF, USE OF THE SAME AND MEDICINAL PRODUCTS BASED ON THESE COMPOUNDS |
DE3924093A1 (en) * | 1989-07-20 | 1991-02-07 | Hoechst Ag | N, N'-BIS (ALKOXY-ALKYL) -PYRIDINE-2,4-DICARBONESAUREDIAMIDES, METHOD FOR THE PRODUCTION AND USE THEREOF |
-
1989
- 1989-07-29 DE DE58908519T patent/DE58908519D1/en not_active Expired - Fee Related
- 1989-07-29 AT AT89114031T patent/ATE113036T1/en not_active IP Right Cessation
- 1989-07-29 ES ES89114031T patent/ES2065355T3/en not_active Expired - Lifetime
- 1989-07-29 EP EP89114031A patent/EP0353668B1/en not_active Expired - Lifetime
- 1989-08-02 IL IL91185A patent/IL91185A/en not_active IP Right Cessation
- 1989-08-03 AU AU39263/89A patent/AU615324B2/en not_active Ceased
- 1989-08-03 KR KR1019890011072A patent/KR0137789B1/en not_active IP Right Cessation
- 1989-08-03 PT PT91361A patent/PT91361B/en active IP Right Grant
- 1989-08-03 DK DK380989A patent/DK170748B1/en not_active IP Right Cessation
- 1989-08-03 IE IE252089A patent/IE64673B1/en not_active IP Right Cessation
- 1989-08-03 CA CA000607509A patent/CA1330802C/en not_active Expired - Fee Related
- 1989-08-03 JP JP1200441A patent/JP2683423B2/en not_active Expired - Lifetime
- 1989-08-04 HU HU893966A patent/HU208423B/en not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU599746B2 (en) * | 1987-02-10 | 1990-07-26 | Hoechst Aktiengesellschaft | Pyridine-2,4- and -2,5-dicarboxylic acid amides, processes for their preparation, the use thereof, and medicaments based on these compounds |
AU600084B2 (en) * | 1987-02-10 | 1990-08-02 | Hoechst Aktiengesellschaft | Pyridine-2,4- and -2,5-dicarboxylic acid derivatives, processes for their preparation, the use thereof and medicaments based on these compounds |
AU604293B2 (en) * | 1987-02-10 | 1990-12-13 | Hoechst Aktiengesellschaft | Pyridine-2,4- and 2,5-dicarboxylic acid derivatives, a process for their preparation, the use thereof, and medicaments based on these compounds |
US5482953A (en) * | 1991-02-05 | 1996-01-09 | Hoechst Aktiengesellschaft | 2,4-and 2,5-bistetrazolylpyridines and the use thereof as pharmaceuticals |
US5614537A (en) * | 1991-02-05 | 1997-03-25 | Hoechst Aktiengesellschaft | 2,4-and 2,5-bistetrazolylpyridines, a process for the preparation thereof and the use thereof as pharmaceuticals |
Also Published As
Publication number | Publication date |
---|---|
JP2683423B2 (en) | 1997-11-26 |
IE64673B1 (en) | 1995-08-23 |
DE58908519D1 (en) | 1994-11-24 |
ES2065355T3 (en) | 1995-02-16 |
KR0137789B1 (en) | 1998-05-15 |
DK380989D0 (en) | 1989-08-03 |
HUT52057A (en) | 1990-06-28 |
DK170748B1 (en) | 1996-01-08 |
ATE113036T1 (en) | 1994-11-15 |
KR900003125A (en) | 1990-03-23 |
EP0353668B1 (en) | 1994-10-19 |
IE892520L (en) | 1990-02-04 |
HU208423B (en) | 1993-10-28 |
PT91361A (en) | 1990-03-08 |
EP0353668A3 (en) | 1991-03-27 |
DK380989A (en) | 1990-02-05 |
PT91361B (en) | 1995-05-04 |
JPH0283371A (en) | 1990-03-23 |
CA1330802C (en) | 1994-07-19 |
IL91185A0 (en) | 1990-03-19 |
AU615324B2 (en) | 1991-09-26 |
IL91185A (en) | 1993-06-10 |
EP0353668A2 (en) | 1990-02-07 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |