US2188244A - Pyridine carboxylic acid morpholides - Google Patents
Pyridine carboxylic acid morpholides Download PDFInfo
- Publication number
- US2188244A US2188244A US159604A US15960437A US2188244A US 2188244 A US2188244 A US 2188244A US 159604 A US159604 A US 159604A US 15960437 A US15960437 A US 15960437A US 2188244 A US2188244 A US 2188244A
- Authority
- US
- United States
- Prior art keywords
- pyridine carboxylic
- carboxylic acid
- morpholine
- acid morpholides
- carboxylic acids
- 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.)
- Expired - Lifetime
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
- C07D213/60—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
- C07D213/82—Amides; Imides in position 3
Definitions
- pyridine carboxylic acids can give new amido derivatives with amines such as morpholine (a complex function compound) giving results superior to those obtained up to this time with other derivatives of analogous kind.
- Our invention which is based upon the foregoing therapeutic discovery consists essentially in reacting, in the presence of suitable dehydrating reagents, and especially in the presence of phosphorus oxy-chloride, a pyridine carboxylic acid (alpha, beta or gamma) with morpholine, i. e., a secondary amine of the following formula:
- N o CH CQz which exhibits both a secondary amine function and an ether function.
- Example I We mix, as intimately as possible, 83 parts by weight of morpholine with 110 parts by weight of nicotinic acid and we add 50 parts by weight of phosphorus oxychloride, taking care that the reaction does not become too violent but, however, raising the temperature sufficiently to enable the reaction to proceed.
- This amide which at first has a viscous consistency, subsequently solidifies to form a solid which crystallizes normally and melts at a temperature of about 70 C. Its formula is:
- Example II hours we again add 9 kilograms of morpholine and the operation is continued.
- therapeutically useful compound having a melting pointof about 70 C.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR200846X | 1936-10-12 | ||
FR190737X | 1937-07-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2188244A true US2188244A (en) | 1940-01-23 |
Family
ID=26214028
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US159604A Expired - Lifetime US2188244A (en) | 1936-10-12 | 1937-08-17 | Pyridine carboxylic acid morpholides |
Country Status (5)
Country | Link |
---|---|
US (1) | US2188244A (pl) |
BE (1) | BE424052A (pl) |
CH (1) | CH200846A (pl) |
GB (1) | GB503780A (pl) |
NL (1) | NL46009C (pl) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2447587A (en) * | 1942-12-18 | 1948-08-24 | Geigy Ag J R | Acyl glycine amides |
US2870148A (en) * | 1957-01-23 | 1959-01-20 | Bristol Lab Inc | Heterocyclic amides of n aralkyl piperidine carboxylic acids |
JPS50126671A (pl) * | 1974-03-22 | 1975-10-04 |
-
0
- BE BE424052D patent/BE424052A/xx unknown
- NL NL46009D patent/NL46009C/xx active
-
1937
- 1937-08-17 US US159604A patent/US2188244A/en not_active Expired - Lifetime
- 1937-10-11 CH CH200846D patent/CH200846A/fr unknown
- 1937-10-12 GB GB27725/37A patent/GB503780A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2447587A (en) * | 1942-12-18 | 1948-08-24 | Geigy Ag J R | Acyl glycine amides |
US2870148A (en) * | 1957-01-23 | 1959-01-20 | Bristol Lab Inc | Heterocyclic amides of n aralkyl piperidine carboxylic acids |
JPS50126671A (pl) * | 1974-03-22 | 1975-10-04 | ||
JPS5839834B2 (ja) * | 1974-03-22 | 1983-09-01 | シグマタウ インダストリエ フアルマシウテイシエ リウニテ ソシエタ ペル アジオニ | ニコチノイルチアゾリジン誘導体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
NL46009C (pl) | |
BE424052A (pl) | |
CH200846A (fr) | 1938-10-31 |
GB503780A (en) | 1939-04-12 |
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