DD216019A5 - Verfahren zur herstellung heterocyclisch ankondensierter pyrazolo (3,4-d) pyridin-3-one - Google Patents
Verfahren zur herstellung heterocyclisch ankondensierter pyrazolo (3,4-d) pyridin-3-one Download PDFInfo
- Publication number
- DD216019A5 DD216019A5 DD84259293A DD25929384A DD216019A5 DD 216019 A5 DD216019 A5 DD 216019A5 DD 84259293 A DD84259293 A DD 84259293A DD 25929384 A DD25929384 A DD 25929384A DD 216019 A5 DD216019 A5 DD 216019A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- lower alkyl
- substituted
- halogen
- formula
- compound
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- OCBGRKUCCSEAII-UHFFFAOYSA-N pyrazolo[4,3-c]pyridin-3-one Chemical compound C1=NC=C2C(=O)N=NC2=C1 OCBGRKUCCSEAII-UHFFFAOYSA-N 0.000 title 1
- -1 2-aryl-thieno (2 Chemical compound 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims description 106
- 150000003839 salts Chemical class 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000003545 alkoxy group Chemical group 0.000 claims description 60
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000013589 supplement Substances 0.000 claims description 8
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 150000002545 isoxazoles Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 241000134426 Ceratopogonidae Species 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 230000000295 complement effect Effects 0.000 claims 1
- 230000002452 interceptive effect Effects 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 102000004300 GABA-A Receptors Human genes 0.000 abstract description 6
- 108090000839 GABA-A Receptors Proteins 0.000 abstract description 6
- HQSMZMNFBMOEIF-UHFFFAOYSA-N 5H-1,6-naphthyridin-3-one Chemical compound O=C1C=NC2=CC=NCC2=C1 HQSMZMNFBMOEIF-UHFFFAOYSA-N 0.000 abstract 1
- 235000002639 sodium chloride Nutrition 0.000 description 83
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
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- 239000000243 solution Substances 0.000 description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
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- 239000002244 precipitate Substances 0.000 description 25
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000007858 starting material Substances 0.000 description 23
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
- 125000001309 chloro group Chemical group Cl* 0.000 description 15
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 8
- 230000027455 binding Effects 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 239000011737 fluorine Substances 0.000 description 8
- 125000005493 quinolyl group Chemical group 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 7
- 230000001773 anti-convulsant effect Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 7
- 229960003529 diazepam Drugs 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
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- 108020003175 receptors Proteins 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 210000000653 nervous system Anatomy 0.000 description 5
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- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 4
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 3
- GKECDORWWXXNRY-UHFFFAOYSA-N 2h-pyridin-3-one Chemical compound O=C1CN=CC=C1 GKECDORWWXXNRY-UHFFFAOYSA-N 0.000 description 3
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- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 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
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- RCIGDGBXEMECGY-UHFFFAOYSA-N pyridin-3-ylhydrazine Chemical compound NNC1=CC=CN=C1 RCIGDGBXEMECGY-UHFFFAOYSA-N 0.000 description 1
- NURLTSGEEKJEPI-UHFFFAOYSA-N pyrimidin-2-ylhydrazine;hydrochloride Chemical compound Cl.NNC1=NC=CC=N1 NURLTSGEEKJEPI-UHFFFAOYSA-N 0.000 description 1
- QIEQDFYXVYQLLU-UHFFFAOYSA-N pyrimidin-4-ylhydrazine Chemical compound NNC1=CC=NC=N1 QIEQDFYXVYQLLU-UHFFFAOYSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/34—Oxygen atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/457,105 US4479955A (en) | 1983-01-10 | 1983-01-10 | Heterocycle-fused pyrazolo[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD216019A5 true DD216019A5 (de) | 1984-11-28 |
Family
ID=23815456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84259293A DD216019A5 (de) | 1983-01-10 | 1984-01-09 | Verfahren zur herstellung heterocyclisch ankondensierter pyrazolo (3,4-d) pyridin-3-one |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4479955A (da) |
| EP (1) | EP0115469B1 (da) |
| JP (1) | JPS59130882A (da) |
| AT (1) | ATE27276T1 (da) |
| AU (1) | AU2317184A (da) |
| CA (1) | CA1250579A (da) |
| DD (1) | DD216019A5 (da) |
| DE (1) | DE3463769D1 (da) |
| DK (1) | DK8084A (da) |
| ES (2) | ES8606343A1 (da) |
| FI (1) | FI840053A7 (da) |
| GR (1) | GR79458B (da) |
| IL (1) | IL70635A0 (da) |
| NO (1) | NO840068L (da) |
| PT (1) | PT77926B (da) |
| ZA (1) | ZA84154B (da) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4560689A (en) * | 1983-01-10 | 1985-12-24 | Ciba-Geigy Corporation | Heterocyclic-fused pyrazolo-[3,4-d]pyridin-3-ones as benzodiazepine receptor modulators |
| EP0126970A3 (en) * | 1983-04-27 | 1985-11-06 | Beecham Group Plc | Anxiolytic and anti-depressant thienopyridine derivatives |
| US4647566A (en) * | 1984-07-09 | 1987-03-03 | Ciba-Geigy Corporation | Certain ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives in treating anxiety |
| US4602014A (en) * | 1984-07-09 | 1986-07-22 | Ciba-Geigy Corporation | Ring-fused pyrazolo[3,4-d]-pyridin-3-one derivatives as benzodiazepine receptor modulators |
| CA1263651A (en) * | 1984-07-09 | 1989-12-05 | Ciba-Geigy Ag | Certain ring-fused pyrazolo ¬3,4-d|-pyridin-3-one derivatives |
| JPS61112075A (ja) * | 1984-11-05 | 1986-05-30 | Shionogi & Co Ltd | チエニルピラゾロキノリン誘導体 |
| US4596799A (en) * | 1985-01-29 | 1986-06-24 | Ciba-Geigy Corporation | 9H-pyrrolo[2,1-c]-1,2,4-triazolo[4,3-a][1,4]benzodiazepines |
| US4831013A (en) * | 1986-03-20 | 1989-05-16 | Ciba-Geigy Corporation | 2-substituted-e-fused-[1,2,4]triazolo[1,5-c]pyrimidines, pharmaceutical compositions, and uses thereof |
| US4826854A (en) * | 1986-11-25 | 1989-05-02 | Ciba-Geigy Corporation | Certain cycloalka-(b)-pyrazolo(3,4-d)-pyridin-3-one derivatives |
| DE3728278A1 (de) * | 1986-12-17 | 1988-06-23 | Bayer Ag | Herbizide und fungizide mittel auf basis von substituierten pyrazolin-5-on derivaten |
| KR0169813B1 (ko) * | 1995-07-12 | 1999-01-15 | 김종인 | 4-아미노-3-아실나프티리딘 유도체 |
| GB9806102D0 (en) | 1998-03-20 | 1998-05-20 | Merck Sharp & Dohme | Therapeutic agents |
| WO2008154447A1 (en) * | 2007-06-08 | 2008-12-18 | Helicon Therapeutics, Inc. | Therapeutic pyrazolonaphthyridine derivatives |
| WO2012051213A2 (en) * | 2010-10-14 | 2012-04-19 | Helicon Therapeutics, Inc. | Therapeutic 5,6,5-tricyclic analogs |
| RU2481760C2 (ru) * | 2011-05-16 | 2013-05-20 | Александр Иванович Леляк | Способ выращивания растений |
| RU2477596C2 (ru) * | 2011-05-16 | 2013-03-20 | Александр Иванович Леляк | Способ стимуляции роста и защиты ягодных культур от болезней, вызываемых грибными патогенами |
| TW201522337A (zh) * | 2013-03-12 | 2015-06-16 | Arqule Inc | 經取代之三環吡唑並-嘧啶化合物類 |
| US11485733B2 (en) | 2017-06-30 | 2022-11-01 | Bayer Animal Health Gmbh | Azaquinoline derivatives |
Family Cites Families (5)
| 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 |
| US4146621A (en) * | 1973-01-16 | 1979-03-27 | The Regents Of The University Of Michigan | Process of treating proliferative skin diseases |
| EP0022078B1 (de) * | 1979-06-21 | 1984-07-25 | Ciba-Geigy Ag | Pyrazolochinoline, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate enthaltend diese Verbindungen |
| US4312870A (en) * | 1979-06-21 | 1982-01-26 | Ciba-Geigy Corporation | Pyrazoloquinolines |
-
1983
- 1983-01-10 US US06/457,105 patent/US4479955A/en not_active Expired - Fee Related
-
1984
- 1984-01-04 DE DE8484810002T patent/DE3463769D1/de not_active Expired
- 1984-01-04 AT AT84810002T patent/ATE27276T1/de active
- 1984-01-04 EP EP84810002A patent/EP0115469B1/de not_active Expired
- 1984-01-06 IL IL70635A patent/IL70635A0/xx unknown
- 1984-01-06 FI FI840053A patent/FI840053A7/fi not_active Application Discontinuation
- 1984-01-06 PT PT77926A patent/PT77926B/pt unknown
- 1984-01-06 CA CA000444815A patent/CA1250579A/en not_active Expired
- 1984-01-09 JP JP59000937A patent/JPS59130882A/ja active Pending
- 1984-01-09 GR GR73457A patent/GR79458B/el unknown
- 1984-01-09 AU AU23171/84A patent/AU2317184A/en not_active Abandoned
- 1984-01-09 NO NO840068A patent/NO840068L/no unknown
- 1984-01-09 ZA ZA84154A patent/ZA84154B/xx unknown
- 1984-01-09 DD DD84259293A patent/DD216019A5/de unknown
- 1984-01-09 DK DK8084A patent/DK8084A/da not_active Application Discontinuation
- 1984-01-09 ES ES528750A patent/ES8606343A1/es not_active Expired
-
1985
- 1985-06-14 ES ES544184A patent/ES544184A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59130882A (ja) | 1984-07-27 |
| EP0115469B1 (de) | 1987-05-20 |
| FI840053A7 (fi) | 1984-07-11 |
| ES8606343A1 (es) | 1986-04-01 |
| US4479955A (en) | 1984-10-30 |
| NO840068L (no) | 1984-07-11 |
| DK8084D0 (da) | 1984-01-09 |
| CA1250579A (en) | 1989-02-28 |
| DE3463769D1 (en) | 1987-06-25 |
| DK8084A (da) | 1984-07-11 |
| IL70635A0 (en) | 1984-04-30 |
| PT77926A (en) | 1984-02-01 |
| ES544184A1 (es) | 1986-12-01 |
| AU2317184A (en) | 1984-07-12 |
| ES528750A0 (es) | 1986-04-01 |
| ZA84154B (en) | 1984-08-29 |
| GR79458B (da) | 1984-10-30 |
| EP0115469A1 (de) | 1984-08-08 |
| PT77926B (en) | 1986-06-02 |
| FI840053A0 (fi) | 1984-01-06 |
| ATE27276T1 (de) | 1987-06-15 |
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