GB726230A - Novel heterocyclic compounds and process for the manufacture thereof - Google Patents
Novel heterocyclic compounds and process for the manufacture thereofInfo
- Publication number
- GB726230A GB726230A GB6228/53A GB622853A GB726230A GB 726230 A GB726230 A GB 726230A GB 6228/53 A GB6228/53 A GB 6228/53A GB 622853 A GB622853 A GB 622853A GB 726230 A GB726230 A GB 726230A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isonicotinyl
- isonicotinic acid
- chloro
- prepared
- chloride
- 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
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
- C07D213/86—Hydrazides; Thio or imino analogues thereof
Abstract
The invention comprises chemotherapeutically active compounds of the formula <FORM:0726230/IV (b)/1> wherein R represents a halogen atom or a hydroxy, mercapto or amino group, the hydrogen of any which may be substituted by a lower alkyl radical which may contain a hydroxy, carboxy, amino, alkylamino or dialkylamino substituent, and R1 represents a hydrogen atom or any of the R values. They are prepared by condensing an isonicotinic acid halide with an isonicotinic acid hydrazide, the pyridine nucleus of one of the reactants containing chlorine or one of the above groups in the 2- or 2,6-positions, and, if desired, replacing the chlorine if present in the product by one or two of the above groups; or where two chlorine atoms are present, replacing one by hydrogen and, if desired, the other by one of the above groups. In the examples: (1) 2,6-dimethoxy-isonicotinic acid, obtained by heating sodium methoxide and 2,6-dichloronicotinic acid, is converted to the acid chloride by refluxing with thionyl chloride, and heated in pyridine with isonicotinic acid hydrazide to give 1 - (21,61 - dimethoxy - isonicotinyl) - 2-isonicotinyl-hydrazine. Similarly prepared are (2), (3) and (4), the 21,61-diethoxy, 31,61-diisopropyloxy, and 21,61-di-n-butyloxy derivatives; (5) the 21,61-dichloro-derivative is prepared (a) by reacting 2,6 - dichloro - isonicotinic acid hydrazide and isonicotinyl chloride hydrochloride in pyridine, and (b) by reacting the unsubstituted hydrazide with 2,6-dichloroisonicotinyl chloride. From this, 1-(21-chloro-61 - ethyl - mercapto - isoicotinyl) - 2 - isonicotinyl hydrazine is prepared by boiling with sodium methoxide and ethyl mercaptan; (6)-2-chloro-isonicotinic acid, prepared by heating the 2,6 - dichloro - derivative with hydrazine hydrate followed by boiling with copper sulphate solution, is converted to the acid chloride and warmed with isonicotinic acid hydrazide in pyridine to give 1-(21-chloro-isonicotinyl)-2-isoicotinyl-hydrazine; (8) (a) sodium and methanol are heated with 2,6-dichloro-isonicotinic acid to give 2-chloro-6-ethoxy-isonicotinic acid, the chloride is formed which, with isonicotinyl hydrazide, gives 1-(21-chloro-61 - ethoxy - isonicotinyl) - 2 - isonicotinylhydrazine, (b) 2-chloro-6-ethoxy-isonicotinic is hydrogenated with palladium nickel in NaOH to give 2-ethoxy-isonicotinic acid and the process is continued as in (a); (9) 1-(21-methoxyisonicotinyl) - 2 - isonicotinyl hydrazine is prepared by the method of (8) (b). The Specification includes a large number of other radicals as examples of R and R1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH726230X | 1952-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB726230A true GB726230A (en) | 1955-03-16 |
Family
ID=4531959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6228/53A Expired GB726230A (en) | 1952-03-14 | 1953-03-06 | Novel heterocyclic compounds and process for the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB726230A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3131194A (en) * | 1962-12-14 | 1964-04-28 | American Home Prod | Substituted 2-aminoisonicotinic acid hydrazides |
| GB2368843A (en) * | 2000-11-08 | 2002-05-15 | Leuven K U Res & Dev | Non-porphyrin multipurpose contrast agents |
| CN106614663A (en) * | 2016-12-29 | 2017-05-10 | 新沂市中诺新材料科技有限公司 | Novel nanoscale indazole pesticide synthesis method |
-
1953
- 1953-03-06 GB GB6228/53A patent/GB726230A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3131194A (en) * | 1962-12-14 | 1964-04-28 | American Home Prod | Substituted 2-aminoisonicotinic acid hydrazides |
| GB2368843A (en) * | 2000-11-08 | 2002-05-15 | Leuven K U Res & Dev | Non-porphyrin multipurpose contrast agents |
| CN106614663A (en) * | 2016-12-29 | 2017-05-10 | 新沂市中诺新材料科技有限公司 | Novel nanoscale indazole pesticide synthesis method |
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