GB1391244A - 3-amino-1h-pyrazolo-3,4-b-pyridines and a process for their preparation - Google Patents
3-amino-1h-pyrazolo-3,4-b-pyridines and a process for their preparationInfo
- Publication number
- GB1391244A GB1391244A GB3120773A GB3120773A GB1391244A GB 1391244 A GB1391244 A GB 1391244A GB 3120773 A GB3120773 A GB 3120773A GB 3120773 A GB3120773 A GB 3120773A GB 1391244 A GB1391244 A GB 1391244A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- amino
- dihalogeno
- cyanopyridine
- hydrazine
- 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 4
- MJEPPEQNLZSPAP-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridin-3-amine Chemical class C1=CN=C2C(N)=NNC2=C1 MJEPPEQNLZSPAP-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- QPEKJCMSWHAWOC-UHFFFAOYSA-N N-hydrazinyl-N-[hydrazinyl(hydroxy)amino]oxyhydroxylamine Chemical compound N(N)N(O)ON(NN)O QPEKJCMSWHAWOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000006482 condensation reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
- -1 thio compound Chemical class 0.000 abstract 1
- 125000000101 thioether group Chemical group 0.000 abstract 1
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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/14—1,2-Diazoles or hydrogenated 1,2-diazoles ; Pyrazolium; Indazolium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Abstract
1391244 3 - Amino -1 H - pyrazolo pyridines HOECHST AG 29 June 1973 [30 June 1972] 31207/73 Heading C2C Novel 3-amino-1H-pyrazolopyridines of the formula wherein X is a primary, secondary or tertiary amino group, a hydrazino, hydroxylamino, ether or thioether group; Y is a hydrogen atom or an optionally substituted alkyl, cycloalkyl, aryl or heterocyclic radical, and Z is a hydrogen atom or an alkyl group, are prepared by reacting a 2,6-dihalogeno-3-cyanopyridine of the formula wherein Hal is chlorine or bromine, with ammonia, a primary or secondary amine, hydrazine, hydroxylamine, or a hydroxy or thio compound, and condensing the resulting compound of the formula with a hydrazine of the formula The reaction of the 2,6-dihalogeno-3-cyanopyridine is preferably carried out at a temperature of from 20 to 100 C. in an inert solvent, e.g. an aliphatic alcohol, and the condensation reaction is preferably carried out at a temperature of from 70 to 150 C. in an aqueous or aqueous-alcoholic solution.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232038A DE2232038A1 (en) | 1972-06-30 | 1972-06-30 | 3-AMINO-1H-PYRAZOLO SQUARE CLAMP ON 3.4-ANGLE BRACKET FOR PYRIDINE, THEIR PRODUCTION AND USE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1391244A true GB1391244A (en) | 1975-04-16 |
Family
ID=5849251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3120773A Expired GB1391244A (en) | 1972-06-30 | 1973-06-29 | 3-amino-1h-pyrazolo-3,4-b-pyridines and a process for their preparation |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3872133A (en) |
| JP (1) | JPS4949991A (en) |
| AT (1) | AT333758B (en) |
| BE (1) | BE801795A (en) |
| CH (1) | CH590279A5 (en) |
| DE (1) | DE2232038A1 (en) |
| FR (1) | FR2190824B1 (en) |
| GB (1) | GB1391244A (en) |
| NL (1) | NL7308793A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112313232A (en) * | 2018-05-02 | 2021-02-02 | Jw中外制药公司 | Novel heterocyclic derivatives |
| RU2792163C2 (en) * | 2018-05-02 | 2023-03-17 | ДжейВ ФАРМАСЬЮТИКАЛ КОРПОРЕЙШН | New heterocyclic derivative |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5163193A (en) * | 1974-11-26 | 1976-06-01 | Yoshitomi Pharmaceutical | TETORAHIDOROPIRAZOROPIRIJINKAGOBUTSUNO SEIZOHO |
| US4020072A (en) * | 1976-05-04 | 1977-04-26 | E. R. Squibb & Sons, Inc. | 5-Aminomethyl-1H-pyrazolo[3,4-b]pyridines |
| DE2643753A1 (en) * | 1976-09-29 | 1978-04-06 | Thomae Gmbh Dr K | NEW 1H-PYRAZOLO ANGLE CLAMP ON 3.4-B ANGLE CLAMP TO PYRIDINE |
| IL62306A0 (en) * | 1980-03-17 | 1981-05-20 | Sterling Drug Inc | Pyrazolopyridinones and pyridinylnicotinates,their preparation and pharmaceutical compositions containing them |
| US4264603A (en) * | 1980-03-17 | 1981-04-28 | Sterling Drug Inc. | 5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridine-3-amines, their use as cardiotonics and their preparation |
| US4361568A (en) * | 1981-04-28 | 1982-11-30 | Sterling Drug Inc. | 5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridin-3-amines and their cardiotonic use |
| MX2008002385A (en) * | 2005-08-25 | 2008-03-18 | Hoffmann La Roche | P38 map kinase inhibitors and methods for using the same. |
| EP2789615B1 (en) | 2009-08-11 | 2017-05-03 | Bristol-Myers Squibb Company | Azaindazoles as Btk kinase modulators and use thereof |
| US8742106B2 (en) | 2009-12-21 | 2014-06-03 | Novartis Ag | Disubstituted heteroaryl-fused pyridines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3733328A (en) * | 1971-11-04 | 1973-05-15 | Squibb & Sons Inc | Pyrazolo(3,4-b)pyridine-5-carboxamides |
-
1972
- 1972-06-30 DE DE2232038A patent/DE2232038A1/en active Pending
-
1973
- 1973-06-25 NL NL7308793A patent/NL7308793A/xx unknown
- 1973-06-26 US US373766A patent/US3872133A/en not_active Expired - Lifetime
- 1973-06-27 CH CH937573A patent/CH590279A5/xx not_active IP Right Cessation
- 1973-06-28 AT AT568373A patent/AT333758B/en not_active IP Right Cessation
- 1973-06-29 JP JP48072993A patent/JPS4949991A/ja active Pending
- 1973-06-29 GB GB3120773A patent/GB1391244A/en not_active Expired
- 1973-06-29 FR FR7323937A patent/FR2190824B1/fr not_active Expired
- 1973-07-02 BE BE133019A patent/BE801795A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112313232A (en) * | 2018-05-02 | 2021-02-02 | Jw中外制药公司 | Novel heterocyclic derivatives |
| EP3822270A4 (en) * | 2018-05-02 | 2022-03-02 | JW Pharmaceutical Corporation | Novel heterocycle derivative |
| RU2792163C2 (en) * | 2018-05-02 | 2023-03-17 | ДжейВ ФАРМАСЬЮТИКАЛ КОРПОРЕЙШН | New heterocyclic derivative |
| CN112313232B (en) * | 2018-05-02 | 2024-03-08 | Jw中外制药公司 | Novel heterocyclic derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA568373A (en) | 1976-04-15 |
| US3872133A (en) | 1975-03-18 |
| CH590279A5 (en) | 1977-07-29 |
| AT333758B (en) | 1976-12-10 |
| FR2190824B1 (en) | 1976-11-12 |
| JPS4949991A (en) | 1974-05-15 |
| FR2190824A1 (en) | 1974-02-01 |
| NL7308793A (en) | 1974-01-02 |
| BE801795A (en) | 1974-01-02 |
| DE2232038A1 (en) | 1974-01-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |