DE2504588A1 - Neue derivate von furo(2,3-d)pyrazolo (3,4-b)pyridinen - Google Patents
Neue derivate von furo(2,3-d)pyrazolo (3,4-b)pyridinenInfo
- Publication number
- DE2504588A1 DE2504588A1 DE19752504588 DE2504588A DE2504588A1 DE 2504588 A1 DE2504588 A1 DE 2504588A1 DE 19752504588 DE19752504588 DE 19752504588 DE 2504588 A DE2504588 A DE 2504588A DE 2504588 A1 DE2504588 A1 DE 2504588A1
- Authority
- DE
- Germany
- Prior art keywords
- lower alkyl
- pyrazolo
- furo
- pyridine
- formula
- 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.)
- Pending
Links
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 1
- -1 ethoxycarbonylmethoxy Chemical group 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000006309 butyl amino group Chemical group 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 239000006201 parenteral dosage form Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- CLKXTSGSOPYRTQ-UHFFFAOYSA-N (10-ethyl-5-hydroxy-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaen-4-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=2C(=C3C(=NC2)N(N=C3)CC)O1)O CLKXTSGSOPYRTQ-UHFFFAOYSA-N 0.000 description 1
- UDXRYVBGKNTRIC-UHFFFAOYSA-N (5-ethoxy-10-ethyl-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaen-4-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=2C(=C3C(=NC2)N(N=C3)CC)O1)OCC UDXRYVBGKNTRIC-UHFFFAOYSA-N 0.000 description 1
- GVLRTOYGRNLSDW-UHFFFAOYSA-N 1h-pyrazolo[3,4-b]pyridine Chemical compound C1=CC=C2C=NNC2=N1 GVLRTOYGRNLSDW-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- YNROYERVWVCVJJ-UHFFFAOYSA-N 5-ethoxy-10-ethyl-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaene-4-carboxylic acid Chemical compound C(C)OC1=C(OC2=C3C(=NC=C21)N(N=C3)CC)C(=O)O YNROYERVWVCVJJ-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JDRALZAKSPZXNW-UHFFFAOYSA-N CCOC(=O)C1=CN=C2C(=C1)C=NN2C Chemical compound CCOC(=O)C1=CN=C2C(=C1)C=NN2C JDRALZAKSPZXNW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- FBTCFJIPVTURDR-UHFFFAOYSA-N [5-(diethylamino)-7,10,12-trimethyl-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaen-4-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=2C(=C3C(=NC2C)N(N=C3C)C)O1)N(CC)CC FBTCFJIPVTURDR-UHFFFAOYSA-N 0.000 description 1
- ZVXPBPQRNLYSHA-UHFFFAOYSA-N [5-(ethylamino)-7,10,12-trimethyl-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaen-4-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=2C(=C3C(=NC2C)N(N=C3C)C)O1)NCC ZVXPBPQRNLYSHA-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 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 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 210000001608 connective tissue cell Anatomy 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- JMUROHROYQDOHF-UHFFFAOYSA-N ethyl 1-(furan-2-ylmethyl)-4-oxo-7H-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound N1=CC2=C(O)C(C(=O)OCC)=CN=C2N1CC1=CC=CO1 JMUROHROYQDOHF-UHFFFAOYSA-N 0.000 description 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 description 1
- PCUJHHXPZLTMSX-UHFFFAOYSA-N ethyl 10-ethyl-5-hydroxy-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaene-4-carboxylate Chemical compound C(C)OC(=O)C1=C(C=2C(=C3C(=NC2)N(N=C3)CC)O1)O PCUJHHXPZLTMSX-UHFFFAOYSA-N 0.000 description 1
- DWBSMBXTDIFAGZ-UHFFFAOYSA-N ethyl 1h-pyrazolo[3,4-b]pyridine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C2NN=CC2=C1 DWBSMBXTDIFAGZ-UHFFFAOYSA-N 0.000 description 1
- TVFHDWJEVKZZTE-UHFFFAOYSA-N ethyl 5-ethoxy-12-methyl-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1(12),2(6),4,7,9-pentaene-4-carboxylate Chemical compound C(C)OC(=O)C1=C(C=2C(=C3C(=NC2)NN=C3C)O1)OCC TVFHDWJEVKZZTE-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008752 local inflammatory process Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HDWJXYQMEDXSFG-UHFFFAOYSA-N methyl 5-hydroxy-10,12-dimethyl-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaene-4-carboxylate Chemical compound COC(=O)C1=C(C=2C(=C3C(=NC2)N(N=C3C)C)O1)O HDWJXYQMEDXSFG-UHFFFAOYSA-N 0.000 description 1
- TXZGRGVFEBWXOY-UHFFFAOYSA-N methyl 5-hydroxy-10-(2-phenylethyl)-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaene-4-carboxylate Chemical compound COC(=O)C1=C(C=2C(=C3C(=NC2)N(N=C3)CCC3=CC=CC=C3)O1)O TXZGRGVFEBWXOY-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- JSRRNLHJMICLCI-UHFFFAOYSA-N phenyl-(5-propoxy-3-oxa-8,10,11-triazatricyclo[7.3.0.02,6]dodeca-1,4,6,8,11-pentaen-4-yl)methanone Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=2C(=C3C(=NC2)NN=C3)O1)OCCC JSRRNLHJMICLCI-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US439777A US3880867A (en) | 1974-02-05 | 1974-02-05 | Derivatives of furo(2,3-d)pyrazolo(3,4-b)pyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2504588A1 true DE2504588A1 (de) | 1975-08-07 |
Family
ID=23746098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752504588 Pending DE2504588A1 (de) | 1974-02-05 | 1975-02-04 | Neue derivate von furo(2,3-d)pyrazolo (3,4-b)pyridinen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3880867A (en:Method) |
| JP (1) | JPS50108296A (en:Method) |
| CA (1) | CA1051901A (en:Method) |
| DE (1) | DE2504588A1 (en:Method) |
| FR (1) | FR2259605B1 (en:Method) |
| GB (1) | GB1492641A (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4622326A (en) * | 1985-12-23 | 1986-11-11 | Hoechst-Roussel Pharmaceuticals Inc. | 6H-isoxazolo(5,4-d)pyrazolo(3,4-b)pyridines, and their use as antihypertensive and analgesic agents |
| WO2001083487A1 (fr) * | 2000-04-28 | 2001-11-08 | Yamanouchi Pharmaceutical Co., Ltd. | Derive de froindazole |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3697532A (en) * | 1970-08-12 | 1972-10-10 | Squibb & Sons Inc | 5-methyldipyrazolo {8 3,4-b;3{40 ,4{40 -d{9 {0 pyridin-3(2h)-ones |
| US3669950A (en) * | 1970-12-01 | 1972-06-13 | Squibb & Sons Inc | DIPYRAZOLO{8 3,4-b:3,4d{9 -PYRIDIN-3-ONES |
| US3787430A (en) * | 1972-07-13 | 1974-01-22 | Squibb & Sons Inc | Derivatives of dipyrazolo(3,4-b;3',4'-d)pyridines |
-
1974
- 1974-02-05 US US439777A patent/US3880867A/en not_active Expired - Lifetime
-
1975
- 1975-01-29 CA CA218,981A patent/CA1051901A/en not_active Expired
- 1975-01-30 GB GB4134/75A patent/GB1492641A/en not_active Expired
- 1975-02-04 DE DE19752504588 patent/DE2504588A1/de active Pending
- 1975-02-05 JP JP50015874A patent/JPS50108296A/ja active Pending
- 1975-02-05 FR FR7503590A patent/FR2259605B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50108296A (en:Method) | 1975-08-26 |
| GB1492641A (en) | 1977-11-23 |
| FR2259605B1 (en:Method) | 1979-08-24 |
| CA1051901A (en) | 1979-04-03 |
| US3880867A (en) | 1975-04-29 |
| FR2259605A1 (en:Method) | 1975-08-29 |
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