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
- 150000001412 amines Chemical class 0.000 title abstract 3
- 150000002576 ketones Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 150000002431 hydrogen Chemical class 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- FSJOLBAFVKSQQJ-UHFFFAOYSA-N 2-ethylpyrazol-3-amine Chemical compound CCN1N=CC=C1N FSJOLBAFVKSQQJ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- LCZQYXCFLGZBML-UHFFFAOYSA-N (4-chloro-1-ethylpyrazolo[3,4-b]pyridin-5-yl)-phenylmethanone Chemical compound C=1N=C2N(CC)N=CC2=C(Cl)C=1C(=O)C1=CC=CC=C1 LCZQYXCFLGZBML-UHFFFAOYSA-N 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- UOXJLWQORGXPOQ-UHFFFAOYSA-N 1-(4-chloro-1-ethylpyrazolo[3,4-b]pyridin-5-yl)ethanone Chemical compound CC(=O)C1=CN=C2N(CC)N=CC2=C1Cl UOXJLWQORGXPOQ-UHFFFAOYSA-N 0.000 abstract 1
- UKQGIOIORXFKHU-UHFFFAOYSA-N 1-(4-ethoxy-1-ethylpyrazolo[3,4-b]pyridin-5-yl)ethanone Chemical compound C(C)(=O)C=1C(=C2C(=NC1)N(N=C2)CC)OCC UKQGIOIORXFKHU-UHFFFAOYSA-N 0.000 abstract 1
- YAKIOQREGCHZQU-UHFFFAOYSA-N 5-acetyl-1-ethyl-7H-pyrazolo[3,4-b]pyridin-4-one Chemical compound C(C)(=O)C=1C(=C2C(=NC1)N(N=C2)CC)O YAKIOQREGCHZQU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003874 central nervous system depressant Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- YAHUDNWHZFLCBN-UHFFFAOYSA-N ethyl 2-benzoyl-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C(=O)OCC)C(=O)C1=CC=CC=C1 YAHUDNWHZFLCBN-UHFFFAOYSA-N 0.000 abstract 1
- CIIPJOUSYBHNNF-UHFFFAOYSA-N ethyl 5-[(2-ethylpyrazol-3-yl)amino]-3-oxopent-4-enoate Chemical compound C(C)OC(CC(=O)C=CNC1=CC=NN1CC)=O CIIPJOUSYBHNNF-UHFFFAOYSA-N 0.000 abstract 1
- XDHWYQRLMSOZOP-UHFFFAOYSA-N ethyl 5-ethoxy-3-oxopent-4-enoate Chemical compound CCOC=CC(=O)CC(=O)OCC XDHWYQRLMSOZOP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000000197 pyrolysis Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
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)
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 (cg-RX-API-DMAC7.html) |
| CA (1) | CA999298A (cg-RX-API-DMAC7.html) |
| CH (1) | CH557368A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2225433A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2139035B1 (cg-RX-API-DMAC7.html) |
| GB (2) | GB1399469A (cg-RX-API-DMAC7.html) |
| HU (1) | HU165257B (cg-RX-API-DMAC7.html) |
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 DE DE19722225433 patent/DE2225433A1/de not_active Withdrawn
- 1972-05-25 JP JP5238772A patent/JPS5629671B1/ja active Pending
- 1972-05-25 CH CH770072A patent/CH557368A/fr not_active IP Right Cessation
- 1972-05-25 HU HUSU000743 patent/HU165257B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU165257B (cg-RX-API-DMAC7.html) | 1974-07-27 |
| CH557368A (fr) | 1974-12-31 |
| FR2139035B1 (cg-RX-API-DMAC7.html) | 1975-10-31 |
| FR2139035A1 (cg-RX-API-DMAC7.html) | 1973-01-05 |
| JPS5629671B1 (cg-RX-API-DMAC7.html) | 1981-07-09 |
| GB1399470A (en) | 1975-07-02 |
| DE2225433A1 (de) | 1972-12-07 |
| CA999298A (en) | 1976-11-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |