IL90552A - History of 3-oxo-propanitrile compressed pyrizole, their preparation and pharmaceutical preparations containing them - Google Patents
History of 3-oxo-propanitrile compressed pyrizole, their preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL90552A IL90552A IL9055289A IL9055289A IL90552A IL 90552 A IL90552 A IL 90552A IL 9055289 A IL9055289 A IL 9055289A IL 9055289 A IL9055289 A IL 9055289A IL 90552 A IL90552 A IL 90552A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- group
- oxo
- cyano
- dihydro
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- JHKHZUNDFBNXET-UHFFFAOYSA-N 3-oxopropanenitrile;1h-pyrazole Chemical class C=1C=NNC=1.O=CCC#N JHKHZUNDFBNXET-UHFFFAOYSA-N 0.000 title abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 41
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 152
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 111
- -1 N-pyrrolidinyl Chemical group 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- ZGONRPXUNVTWTA-UHFFFAOYSA-N methyl 2-isocyanatoacetate Chemical compound COC(=O)CN=C=O ZGONRPXUNVTWTA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 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 description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229910014585 C2-Ce Inorganic materials 0.000 claims 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 9
- 230000001580 bacterial effect Effects 0.000 abstract description 4
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- 230000001613 neoplastic effect Effects 0.000 abstract description 2
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 33
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000005457 ice water Substances 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000000460 chlorine Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 15
- 230000008025 crystallization Effects 0.000 description 15
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 14
- 230000007935 neutral effect Effects 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
- 239000012312 sodium hydride Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 229940086542 triethylamine Drugs 0.000 description 9
- 229940024606 amino acid Drugs 0.000 description 8
- 239000003480 eluent Substances 0.000 description 8
- 238000007912 intraperitoneal administration Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
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- 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 5
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- ZLIZZDCWMOGEGA-UHFFFAOYSA-N 1h-pyrazole-5-carbonyl chloride Chemical compound ClC(=O)C=1C=CNN=1 ZLIZZDCWMOGEGA-UHFFFAOYSA-N 0.000 description 4
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- 229910052740 iodine Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
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- UBPVIFJIKVBXOL-UHFFFAOYSA-N n-butyl-2-cyano-3-oxo-3-(1-phenyl-4h-indeno[1,2-c]pyrazol-3-yl)propanamide Chemical compound C1C2=CC=CC=C2C2=C1C(C(=O)C(C#N)C(=O)NCCCC)=NN2C1=CC=CC=C1 UBPVIFJIKVBXOL-UHFFFAOYSA-N 0.000 description 1
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- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 210000003024 peritoneal macrophage Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
- C07D495/02—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 two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- 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
- 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
- C07D491/02—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 two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888814587A GB8814587D0 (en) | 1988-06-20 | 1988-06-20 | Condensed pyrazole 3-oxo-propanenitrile derivatives & process for their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL90552A0 IL90552A0 (en) | 1990-01-18 |
| IL90552A true IL90552A (en) | 1994-08-26 |
Family
ID=10638992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9055289A IL90552A (en) | 1988-06-20 | 1989-06-07 | History of 3-oxo-propanitrile compressed pyrizole, their preparation and pharmaceutical preparations containing them |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5424308A (cs) |
| EP (2) | EP0422051A1 (cs) |
| JP (1) | JPH03505205A (cs) |
| KR (1) | KR900701756A (cs) |
| CN (1) | CN1022322C (cs) |
| AT (1) | ATE88700T1 (cs) |
| AU (1) | AU634966B2 (cs) |
| CZ (1) | CZ284336B6 (cs) |
| DE (1) | DE68906200T2 (cs) |
| DK (1) | DK163581C (cs) |
| ES (1) | ES2054930T3 (cs) |
| GB (1) | GB8814587D0 (cs) |
| HU (1) | HU206872B (cs) |
| IE (1) | IE63189B1 (cs) |
| IL (1) | IL90552A (cs) |
| NZ (1) | NZ229450A (cs) |
| PT (1) | PT90905B (cs) |
| RU (1) | RU2109735C1 (cs) |
| WO (1) | WO1989012630A1 (cs) |
| YU (1) | YU46937B (cs) |
| ZA (1) | ZA894678B (cs) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8907799D0 (en) * | 1989-04-06 | 1989-05-17 | Erba Carlo Spa | Heteroaryl-3-oxo-propanenitrile derivatives useful in the treatment of rheumatoid arthritis and other autoimmune diseases |
| US5260328A (en) * | 1989-04-06 | 1993-11-09 | Farmitalia Carlo Erba Srl | Phenyl-indenopurazol 3-oxo-propanamide derivatives useful in the treatment of rheumatoid arthritis |
| GB8916290D0 (en) * | 1989-07-17 | 1989-08-31 | Erba Carlo Spa | Heteroaryl-3-oxo-propanenitrile derivatives useful in stimulating myelopoiesis |
| US6492411B1 (en) | 1993-11-30 | 2002-12-10 | G. D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides for the treatment of inflammation |
| US5466823A (en) * | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| ES2141916T3 (es) * | 1993-11-30 | 2000-04-01 | Searle & Co | Pirazolil-bencenosulfonamidas sustituidas para el tratamiento de la inflamacion. |
| US6716991B1 (en) | 1993-11-30 | 2004-04-06 | G. D. Searle & Co. | Process for preparing a substituted pyrazolyl benzenesulfonamide for the treatment of inflammation |
| US5547975A (en) * | 1994-09-20 | 1996-08-20 | Talley; John J. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
| US5886016A (en) * | 1995-09-15 | 1999-03-23 | G.D. Searle & Co. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
| US5756529A (en) * | 1995-09-29 | 1998-05-26 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides for use in veterinary therapies |
| GB9716103D0 (en) * | 1997-07-30 | 1997-10-01 | Pharmacia & Upjohn Spa | Condensed heterocyclic compounds |
| EP1427706B1 (en) | 2001-09-19 | 2007-05-30 | Pharmacia Corporation | Substituted pyrazolo compounds for the treatment of inflammation |
| BR0212611A (pt) | 2001-09-19 | 2004-08-17 | Pharmacia Corp | Compostos de pirazolila substituìdos para o tratamento da inflamação |
| JP2005507892A (ja) | 2001-09-19 | 2005-03-24 | ファルマシア・コーポレーション | 炎症の治療のための置換されたピラゾリルベンゼンスルファミド化合物 |
| CN114718407A (zh) * | 2022-03-01 | 2022-07-08 | 东风柳州汽车有限公司 | 车窗控制方法、装置、设备及存储介质 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2989538A (en) * | 1960-02-10 | 1961-06-20 | Smith Kline French Lab | Process for preparing pyrazoloindenone hydrazones |
| US3004983A (en) * | 1960-05-16 | 1961-10-17 | Smith Kline French Lab | 4-aminopyrazolo [3, 4-a] indene derivatives |
| US4140785A (en) * | 1978-05-08 | 1979-02-20 | E. I. Du Pont De Nemours And Company | N-(benzothienopyrazol)amide antirhinoviral agents |
| US4173634A (en) * | 1979-02-23 | 1979-11-06 | E. R. Squibb & Sons, Inc. | Basically-substituted tricyclic pyrazoles useful as antiinflammatory agents |
| US4431657A (en) * | 1982-05-24 | 1984-02-14 | Ayerst, Mckenna & Harrison Inc. | Analgesic compositions consisting of 2H-benzothieno[3,2-c]pyrazol-3-amine derivatives |
| US4420476A (en) * | 1982-05-24 | 1983-12-13 | Averst McKenna & Harrison, Inc. | Benzofuro[3,2-c]pyrazol-3-amine derivatives |
| US4816467A (en) * | 1987-01-09 | 1989-03-28 | Farmitalia Carlo Erba S.R.L | Heteroaryl 3-oxo-propanenitrile derivatives, pharmaceutical compositions and use |
| AU609808B2 (en) * | 1987-04-09 | 1991-05-09 | E.I. Du Pont De Nemours And Company | Insecticidal substituted indazoles |
| GB8814586D0 (en) * | 1988-06-20 | 1988-07-27 | Erba Carlo Spa | Tricyclic 3-oxo-propanenitrile derivatives & process for their preparation |
| GB8916290D0 (en) * | 1989-07-17 | 1989-08-31 | Erba Carlo Spa | Heteroaryl-3-oxo-propanenitrile derivatives useful in stimulating myelopoiesis |
-
1988
- 1988-06-20 GB GB888814587A patent/GB8814587D0/en active Pending
-
1989
- 1989-06-07 IL IL9055289A patent/IL90552A/en not_active IP Right Cessation
- 1989-06-08 NZ NZ229450A patent/NZ229450A/xx unknown
- 1989-06-16 US US07/635,157 patent/US5424308A/en not_active Expired - Fee Related
- 1989-06-16 ES ES89110986T patent/ES2054930T3/es not_active Expired - Lifetime
- 1989-06-16 EP EP89907133A patent/EP0422051A1/en active Pending
- 1989-06-16 AT AT89110986T patent/ATE88700T1/de not_active IP Right Cessation
- 1989-06-16 AU AU37692/89A patent/AU634966B2/en not_active Ceased
- 1989-06-16 EP EP89110986A patent/EP0347773B1/en not_active Expired - Lifetime
- 1989-06-16 RU SU4894213A patent/RU2109735C1/ru active
- 1989-06-16 HU HU894019A patent/HU206872B/hu not_active IP Right Cessation
- 1989-06-16 WO PCT/EP1989/000682 patent/WO1989012630A1/en not_active Application Discontinuation
- 1989-06-16 DE DE8989110986T patent/DE68906200T2/de not_active Expired - Fee Related
- 1989-06-16 JP JP1506679A patent/JPH03505205A/ja active Pending
- 1989-06-19 PT PT90905A patent/PT90905B/pt active IP Right Grant
- 1989-06-19 CZ CS893701A patent/CZ284336B6/cs not_active IP Right Cessation
- 1989-06-19 YU YU125489A patent/YU46937B/sh unknown
- 1989-06-19 IE IE198289A patent/IE63189B1/en not_active IP Right Cessation
- 1989-06-20 CN CN89104203A patent/CN1022322C/zh not_active Expired - Fee Related
- 1989-06-20 ZA ZA894678A patent/ZA894678B/xx unknown
-
1990
- 1990-02-19 KR KR1019900700337A patent/KR900701756A/ko not_active Ceased
- 1990-12-19 DK DK300890A patent/DK163581C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| US5424308A (en) | 1995-06-13 |
| NZ229450A (en) | 1990-08-28 |
| ZA894678B (en) | 1991-02-27 |
| EP0422051A1 (en) | 1991-04-17 |
| PT90905A (pt) | 1989-12-29 |
| AU634966B2 (en) | 1993-03-11 |
| DE68906200D1 (de) | 1993-06-03 |
| IE63189B1 (en) | 1995-03-22 |
| DK300890D0 (da) | 1990-12-19 |
| IL90552A0 (en) | 1990-01-18 |
| CN1038642A (zh) | 1990-01-10 |
| CZ370189A3 (cs) | 1998-07-15 |
| KR900701756A (ko) | 1990-12-04 |
| ES2054930T3 (es) | 1994-08-16 |
| DE68906200T2 (de) | 1993-08-05 |
| ATE88700T1 (de) | 1993-05-15 |
| EP0347773B1 (en) | 1993-04-28 |
| DK163581B (da) | 1992-03-16 |
| CN1022322C (zh) | 1993-10-06 |
| HUT56076A (en) | 1991-07-29 |
| YU46937B (sh) | 1994-06-24 |
| YU125489A (en) | 1991-04-30 |
| CZ284336B6 (cs) | 1998-10-14 |
| PT90905B (pt) | 1994-12-30 |
| DK300890A (da) | 1991-02-20 |
| WO1989012630A1 (en) | 1989-12-28 |
| HU206872B (en) | 1993-01-28 |
| DK163581C (da) | 1992-08-10 |
| EP0347773A1 (en) | 1989-12-27 |
| AU3769289A (en) | 1990-01-12 |
| GB8814587D0 (en) | 1988-07-27 |
| JPH03505205A (ja) | 1991-11-14 |
| HU894019D0 (en) | 1991-06-28 |
| RU2109735C1 (ru) | 1998-04-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |