GB1399469A - Amino derivatives of pyrazolopyridine ketones - Google Patents
Amino derivatives of pyrazolopyridine ketonesInfo
- Publication number
- GB1399469A GB1399469A GB2422372A GB2422372A GB1399469A GB 1399469 A GB1399469 A GB 1399469A GB 2422372 A GB2422372 A GB 2422372A GB 2422372 A GB2422372 A GB 2422372A GB 1399469 A GB1399469 A GB 1399469A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- phenyl
- pyridine
- ethyl
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1399469 Amino derivatives of pyrazolopyridine ketones E R SQUIBB & SONS Inc 23 May 1972 [25 May 1971] 24223/72 Heading C2C Novel compounds of the Formula I wherein R 1 is hydrogen, alkyl, phenyl or phenyl alkylene, R 2 is hydrogen or alkyl, R 3 and R 4 each is hydrogen, alkyl, alkanoyl, haloalkanoyl, R 7 ,R 8 -phenyl, phenylalkylene, dialkylaminoalkylene or R 3 and R 4 together with the nitrogen to which they are attached form R 9 ,R 10 - aziridinyl, -pyrrolidino, -piperidino, -pyrazolyl, -hexahydropyrimidinyl, -hexahydropyridazinyl or -piperazinyl, R 5 is alkyl, C 3-7 -cycloalkyl, phenyl, R 7 ,R 8 -phenyl, R6 is hydrogen, alkyl or phenyl, R 7 and R 8 each is hydrogen, halogen or trifluoromethyl and R 9 and R 10 each is hydrogen, alkyl or hydroxyalkyl where all alkyl, alkylene and alkanoyl radicals have up to 8 carbon atoms and acid addition salts thereof may be prepared by reacting either of the compounds VI or VIII with an amine R 3 R 4 NH, optionally followed where R 3 and/or R 4 is alkanoyl or haloalkanoyl by acylating the product I in which at least one of R 3 and R 4 is hydrogen. Compounds of the Formula VIII are the subject of the divided Specification 1,399,470. 5 - Acetyl - 4 - ethoxy - 1 - ethylpyrazolo[3,4- b]pyridine may be prepared by condensing 1- ethyl-5-aminopyrazole with ethoxymethylene acetoacetic acid ethyl ester to form (1-ethyl-5- pyrazolyl)aminomethylene - acetoacetic acid ethyl ester followed by pyrolysis to 5-acetyl-1-ethyl-4- hydroxypyrazolo[3,4-b]pyridine followed by alkylation of the hydroxy group. 5 - Acetyl - 4 - chloro - 1 - ethylpyrazolo[3,4 - b]- pyridine may be prepared by chlorinating the 4-hydroxy compound above. 5 - Benzoyl - 4 - chloro - 1 - ethylpyrazolo[3,4- b]pyridine may be prepared by reacting 5- amino-1-ethyl pyrazole with ethoxymethylene benzoylacetic acid ethyl ester, and pyrolysing the reaction mixture to form 5-benzoyl-1-ethyl- 4-hydroxpyrazolo[3,4-b]pyridine which gives the required intermediate on treatment with phosphorus oxychloride. Pharmaceutical compositions of the compounds I with the usual excipients show antiinflammatory, and CNS depressant activity and may be used to treat asthma when administered orally or parenterally (and topically for anti-inflammatory activity).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14681271A | 1971-05-25 | 1971-05-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1399469A true GB1399469A (en) | 1975-07-02 |
Family
ID=22519094
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2422372A Expired GB1399469A (en) | 1971-05-25 | 1972-05-23 | Amino derivatives of pyrazolopyridine ketones |
GB515275A Expired GB1399470A (en) | 1971-05-25 | 1972-05-23 | Derivatives of pyrazolopyridine ketones |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB515275A Expired GB1399470A (en) | 1971-05-25 | 1972-05-23 | Derivatives of pyrazolopyridine ketones |
Country Status (7)
Country | Link |
---|---|
JP (1) | JPS5629671B1 (en) |
CA (1) | CA999298A (en) |
CH (1) | CH557368A (en) |
DE (1) | DE2225433A1 (en) |
FR (1) | FR2139035B1 (en) |
GB (2) | GB1399469A (en) |
HU (1) | HU165257B (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3855675A (en) * | 1971-05-25 | 1974-12-24 | Squibb & Sons Inc | 1-(2-furanylmethyl)-1h-pyrazolo(3,4-b)pyridine-5-methanones |
CA997351A (en) * | 1973-05-17 | 1976-09-21 | E.R. Squibb And Sons | Amino derivatives of pyrazolopyridine ketones |
US3983128A (en) * | 1973-12-12 | 1976-09-28 | E. R. Squibb & Sons, Inc. | Alcohol derivatives of pyrazolo[3,4-b]pyridines |
GB1593417A (en) * | 1976-12-22 | 1981-07-15 | Squibb & Sons Inc | Carbocyclic-fused pyrazolopyridine derivatives |
EP0193329A3 (en) * | 1985-02-22 | 1987-08-19 | Beecham Group Plc | Pyrazolopyridines, their preparation and pharmaceutical compositions containing them |
US5300498A (en) * | 1993-06-04 | 1994-04-05 | Hoechst-Roussel Pharmaceuticals Incorporated | 6-piperazinyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acids, esters, amides and related compounds |
-
1972
- 1972-05-23 GB GB2422372A patent/GB1399469A/en not_active Expired
- 1972-05-23 CA CA142,740A patent/CA999298A/en not_active Expired
- 1972-05-23 GB GB515275A patent/GB1399470A/en not_active Expired
- 1972-05-25 FR FR7218680A patent/FR2139035B1/fr not_active Expired
- 1972-05-25 JP JP5238772A patent/JPS5629671B1/ja active Pending
- 1972-05-25 DE DE19722225433 patent/DE2225433A1/en not_active Withdrawn
- 1972-05-25 CH CH770072A patent/CH557368A/en not_active IP Right Cessation
- 1972-05-25 HU HUSU000743 patent/HU165257B/hu unknown
Also Published As
Publication number | Publication date |
---|---|
CA999298A (en) | 1976-11-02 |
JPS5629671B1 (en) | 1981-07-09 |
DE2225433A1 (en) | 1972-12-07 |
CH557368A (en) | 1974-12-31 |
HU165257B (en) | 1974-07-27 |
FR2139035B1 (en) | 1975-10-31 |
GB1399470A (en) | 1975-07-02 |
FR2139035A1 (en) | 1973-01-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |