DE2123318C2 - 4-Butylamino-1-äthyl-1H-pyrazolo[3,4-b]pyridin-5-carbonsäureäthylester, Verfahren zu dessen Herstellung und diesen enthaltende pharmazeutische Mittel - Google Patents
4-Butylamino-1-äthyl-1H-pyrazolo[3,4-b]pyridin-5-carbonsäureäthylester, Verfahren zu dessen Herstellung und diesen enthaltende pharmazeutische MittelInfo
- Publication number
- DE2123318C2 DE2123318C2 DE2123318A DE2123318A DE2123318C2 DE 2123318 C2 DE2123318 C2 DE 2123318C2 DE 2123318 A DE2123318 A DE 2123318A DE 2123318 A DE2123318 A DE 2123318A DE 2123318 C2 DE2123318 C2 DE 2123318C2
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- pyrazolo
- carboxylic acid
- ethyl
- butylamino
- 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
- 238000002360 preparation method Methods 0.000 title claims description 3
- IQNQAOGGWGCROX-UHFFFAOYSA-N cartazolate Chemical compound CCCCNC1=C(C(=O)OCC)C=NC2=C1C=NN2CC IQNQAOGGWGCROX-UHFFFAOYSA-N 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 2
- -1 4-Butylamino- Chemical class 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- SBLCYEJKHYBVKD-UHFFFAOYSA-N ethyl 1-ethyl-4-oxo-7H-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C2N(CC)N=CC2=C1O SBLCYEJKHYBVKD-UHFFFAOYSA-N 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 206010003591 Ataxia Diseases 0.000 description 7
- 208000019901 Anxiety disease Diseases 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 230000036506 anxiety Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001977 ataxic effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 3
- 229960004782 chlordiazepoxide Drugs 0.000 description 3
- 230000035622 drinking Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 229940005513 antidepressants Drugs 0.000 description 2
- 230000001914 calming effect Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DDUHZTYCFQRHIY-UHFFFAOYSA-N 7-chloro-3',4,6-trimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione Chemical compound COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- AMUSYIUKEYMNEE-UHFFFAOYSA-N [P].ClO Chemical compound [P].ClO AMUSYIUKEYMNEE-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000049 anti-anxiety effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 230000002716 ataractic effect Effects 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical class C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/38—Nitrogen atoms
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4156870A | 1970-05-28 | 1970-05-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2123318A1 DE2123318A1 (de) | 1971-12-09 |
| DE2123318C2 true DE2123318C2 (de) | 1984-05-03 |
Family
ID=21917210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2123318A Expired DE2123318C2 (de) | 1970-05-28 | 1971-05-11 | 4-Butylamino-1-äthyl-1H-pyrazolo[3,4-b]pyridin-5-carbonsäureäthylester, Verfahren zu dessen Herstellung und diesen enthaltende pharmazeutische Mittel |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS554105B1 (enExample) |
| BE (1) | BE767842A (enExample) |
| CA (1) | CA920592A (enExample) |
| CH (1) | CH527208A (enExample) |
| DE (1) | DE2123318C2 (enExample) |
| ES (1) | ES390163A1 (enExample) |
| FR (1) | FR2100698A1 (enExample) |
| HU (1) | HU163173B (enExample) |
| IE (1) | IE35118B1 (enExample) |
| NL (1) | NL172657C (enExample) |
| SE (1) | SE367202B (enExample) |
| YU (1) | YU37344B (enExample) |
| ZA (1) | ZA711710B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3804843A (en) * | 1971-12-23 | 1974-04-16 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine carbonitriles |
| BE787794A (fr) * | 1972-06-13 | 1973-02-21 | Fratmann Ag | Procede de preparation du n-(1-ethyl-alpha-pyrrolidylmethyl)- 2-methoxy-5-sulfamidobenzamide |
| US3835144A (en) * | 1972-06-16 | 1974-09-10 | Squibb & Sons Inc | Amino derivatives of (4,3-c pyrazolopyridine cabroxylic acids and esters |
| US3840546A (en) * | 1972-11-15 | 1974-10-08 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine carboxamides |
| US3833598A (en) * | 1972-12-29 | 1974-09-03 | Squibb & Sons Inc | Amino derivatives of pyrazolopyridine-6-carboxylic acids and esters |
| PL2222675T3 (pl) * | 2007-12-19 | 2014-02-28 | Genentech Inc | 5-anilinoimidazopirydyny i sposoby zastosowania |
| US8841462B2 (en) * | 2008-07-01 | 2014-09-23 | Robert A. Heald | Bicyclic heterocycles as MEK kinase inhibitors |
| US8492427B2 (en) | 2008-07-01 | 2013-07-23 | Genentech, Inc. | Isoindolones derivatives as MEK kinase inhibitors and methods of use |
-
1971
- 1971-03-16 ZA ZA711710A patent/ZA711710B/xx unknown
- 1971-03-16 CA CA107869A patent/CA920592A/en not_active Expired
- 1971-03-23 IE IE379/71A patent/IE35118B1/xx unknown
- 1971-04-14 ES ES390163A patent/ES390163A1/es not_active Expired
- 1971-04-21 HU HUSU614A patent/HU163173B/hu unknown
- 1971-04-28 YU YU1066/71A patent/YU37344B/xx unknown
- 1971-05-03 CH CH652971A patent/CH527208A/fr not_active IP Right Cessation
- 1971-05-11 DE DE2123318A patent/DE2123318C2/de not_active Expired
- 1971-05-11 JP JP3147571A patent/JPS554105B1/ja active Pending
- 1971-05-14 NL NLAANVRAGE7106688,A patent/NL172657C/xx not_active IP Right Cessation
- 1971-05-27 FR FR7119340A patent/FR2100698A1/fr active Granted
- 1971-05-27 SE SE06895/71A patent/SE367202B/xx unknown
- 1971-05-28 BE BE767842A patent/BE767842A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU37344B (en) | 1984-08-31 |
| IE35118L (en) | 1971-11-28 |
| ZA711710B (en) | 1971-12-29 |
| FR2100698A1 (en) | 1972-03-24 |
| CH527208A (fr) | 1972-08-31 |
| YU106671A (en) | 1983-04-27 |
| CA920592A (en) | 1973-02-06 |
| HU163173B (enExample) | 1973-06-28 |
| BE767842A (fr) | 1971-11-29 |
| DE2123318A1 (de) | 1971-12-09 |
| FR2100698B1 (enExample) | 1974-08-23 |
| NL172657C (nl) | 1983-10-03 |
| NL172657B (nl) | 1983-05-02 |
| SE367202B (enExample) | 1974-05-20 |
| ES390163A1 (es) | 1973-07-01 |
| NL7106688A (enExample) | 1971-11-30 |
| JPS554105B1 (enExample) | 1980-01-29 |
| IE35118B1 (en) | 1975-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C07D471/04 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |