IL89872A - Use of 2-oxindole-1-carboxamides converted at position 3 to prepare boils to suppress T cell function - Google Patents
Use of 2-oxindole-1-carboxamides converted at position 3 to prepare boils to suppress T cell functionInfo
- Publication number
- IL89872A IL89872A IL8987289A IL8987289A IL89872A IL 89872 A IL89872 A IL 89872A IL 8987289 A IL8987289 A IL 8987289A IL 8987289 A IL8987289 A IL 8987289A IL 89872 A IL89872 A IL 89872A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- pharmaceutically
- acceptable base
- base salt
- formula
- Prior art date
Links
- 210000001744 T-lymphocyte Anatomy 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- -1 3-substituted-2-oxindole-1- carboxamides Chemical class 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 18
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- 230000001404 mediated effect Effects 0.000 claims abstract description 12
- 210000000056 organ Anatomy 0.000 claims abstract description 10
- 230000009885 systemic effect Effects 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 7
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 150000004682 monohydrates Chemical class 0.000 claims description 6
- 238000007911 parenteral administration Methods 0.000 claims description 6
- 208000019423 liver disease Diseases 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 206010028417 myasthenia gravis Diseases 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 7
- 239000002585 base Substances 0.000 description 11
- 102000003820 Lipoxygenases Human genes 0.000 description 8
- 108090000128 Lipoxygenases Proteins 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 206010018691 Granuloma Diseases 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
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- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
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- 229920002472 Starch Polymers 0.000 description 2
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- 210000004072 lung Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
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- 238000011200 topical administration Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- UYINJAQCJCYCGO-UHFFFAOYSA-N 2-oxo-3h-indole-1-carboxamide Chemical class C1=CC=C2N(C(=O)N)C(=O)CC2=C1 UYINJAQCJCYCGO-UHFFFAOYSA-N 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000011752 CBA/J (JAX™ mouse strain) Methods 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037391 Pulmonary granuloma Diseases 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
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- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
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- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
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- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
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- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
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- 239000008101 lactose Substances 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000036473 myasthenia Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003961 penetration enhancing agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol 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
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
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- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/181,142 US4853409A (en) | 1988-04-13 | 1988-04-13 | 3-substituted-2-oxindole-1-carboxamides for suppressing T-cell function |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL89872A0 IL89872A0 (en) | 1989-12-15 |
| IL89872A true IL89872A (en) | 1994-06-24 |
Family
ID=22663072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL8987289A IL89872A (en) | 1988-04-13 | 1989-04-06 | Use of 2-oxindole-1-carboxamides converted at position 3 to prepare boils to suppress T cell function |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4853409A (pt) |
| EP (1) | EP0337628B1 (pt) |
| JP (1) | JPH01311022A (pt) |
| KR (1) | KR920002328B1 (pt) |
| AT (1) | ATE89725T1 (pt) |
| AU (1) | AU601326B2 (pt) |
| CA (1) | CA1324762C (pt) |
| DE (1) | DE68906707T2 (pt) |
| DK (1) | DK174289A (pt) |
| HU (1) | HU204996B (pt) |
| IE (1) | IE62751B1 (pt) |
| IL (1) | IL89872A (pt) |
| MY (1) | MY103872A (pt) |
| NZ (1) | NZ228712A (pt) |
| PH (1) | PH25857A (pt) |
| PT (1) | PT90249B (pt) |
| ZA (1) | ZA892622B (pt) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5008283A (en) * | 1990-03-19 | 1991-04-16 | Pfizer Inc. | Use of tenidap to inhibit activation of collagenase and to inhibit the activity of myeloperoxidase |
| US5006547A (en) * | 1990-03-19 | 1991-04-09 | Pfizer Inc. | Tenidap as an inhibitor of the release of elastase by neutrophils |
| US5122534A (en) * | 1991-02-08 | 1992-06-16 | Pfizer Inc. | Use of tenidap to reduce total serum cholesterol, ldl cholesterol and triglycerides |
| DE4111306C2 (de) * | 1991-04-08 | 1994-06-01 | Mack Chem Pharm | Pharmazeutische Zubereitungen, die ein 2-Oxindol-l-carboxamid-derivat enthalten und zur Injektion bestimmt sind |
| DE4111305C2 (de) * | 1991-04-08 | 1994-12-01 | Mack Chem Pharm | Pharmazeutische Zubereitung zur rektalen Applikation, die ein 2-Oxindol-l-carboxamid-derivat enthält |
| US5298522A (en) * | 1993-01-22 | 1994-03-29 | Pfizer Inc. | 6-chloro-5-fluoro-3-(2-thenoyl)-2-oxindole-1-carboxamide as an analgesic and anti-inflammatory agent while maintaining a normal urine protein/creatinine ratio |
| WO1994016694A1 (en) * | 1993-01-22 | 1994-08-04 | Pfizer Inc. | Lysine salt of 6-chloro-5-fluoro-3-(2-thenoyl)-2-oxindole-1-carboxamide |
| US5545656A (en) * | 1995-04-05 | 1996-08-13 | Pfizer Inc. | 2-Oxidole-1-carboxamide pharmaceutical agents for the treatment of alzheimer's disease |
| BG62359B1 (bg) * | 1995-07-13 | 1999-09-30 | Anormed | N,n-диетил-8,8-дипропил-2-азаспиро[4,5]декан-2-пропанаминдималеат |
| AU7503496A (en) * | 1995-12-19 | 1997-07-14 | Pfizer Inc. | Stable, long acting salts of indole derivatives for the treatment of joint diseases |
| EP0826685A1 (en) * | 1996-08-21 | 1998-03-04 | Pfizer Inc. | Stable, long acting salts of carboxamides for the treatment of joint disease |
| WO2006105796A1 (en) * | 2005-04-08 | 2006-10-12 | Leo Pharma A/S | Novel indolinone derivatives |
| EP2886541A1 (en) * | 2013-12-19 | 2015-06-24 | Sanofi | Oxindole derivatives, preparation thereof and therapeutic use in the treatment of AMPK-related diseases |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4556672A (en) * | 1984-03-19 | 1985-12-03 | Pfizer Inc. | 3-Substituted 2-oxindole-1-carboxamides as analgesic and anti-inflammatory agents |
| DE3413572A1 (de) * | 1984-04-11 | 1985-10-24 | Hoechst Ag, 6230 Frankfurt | Oxindol-verbindungen zur behandlung der epilepsie |
| US4569942A (en) * | 1984-05-04 | 1986-02-11 | Pfizer Inc. | N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents |
| AU6898287A (en) * | 1986-01-30 | 1987-08-25 | University Of Utah, The | Treatment of bone loss |
| UA25898A1 (uk) * | 1987-02-02 | 1999-02-26 | Пфайзер Інк. | Спосіб одержаhhя кристалічhої hатрієвої солі 5-хлор-3-(2-теhоїл)-2-оксііhдол-1-карбоксаміду |
-
1988
- 1988-04-13 US US07/181,142 patent/US4853409A/en not_active Expired - Lifetime
-
1989
- 1989-03-28 AT AT89303050T patent/ATE89725T1/de not_active IP Right Cessation
- 1989-03-28 EP EP89303050A patent/EP0337628B1/en not_active Expired - Lifetime
- 1989-03-28 DE DE8989303050T patent/DE68906707T2/de not_active Expired - Fee Related
- 1989-03-31 PH PH38415A patent/PH25857A/en unknown
- 1989-04-06 IL IL8987289A patent/IL89872A/en not_active IP Right Cessation
- 1989-04-08 MY MYPI89000448A patent/MY103872A/en unknown
- 1989-04-10 JP JP1090492A patent/JPH01311022A/ja active Pending
- 1989-04-11 CA CA000596306A patent/CA1324762C/en not_active Expired - Fee Related
- 1989-04-11 PT PT90249A patent/PT90249B/pt not_active IP Right Cessation
- 1989-04-11 ZA ZA892622A patent/ZA892622B/xx unknown
- 1989-04-12 DK DK174289A patent/DK174289A/da not_active Application Discontinuation
- 1989-04-12 HU HU891754A patent/HU204996B/hu not_active IP Right Cessation
- 1989-04-12 NZ NZ228712A patent/NZ228712A/en unknown
- 1989-04-12 IE IE117189A patent/IE62751B1/en not_active IP Right Cessation
- 1989-04-12 KR KR1019890004822A patent/KR920002328B1/ko not_active Expired
- 1989-04-12 AU AU32712/89A patent/AU601326B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DE68906707T2 (de) | 1993-09-16 |
| JPH01311022A (ja) | 1989-12-15 |
| IL89872A0 (en) | 1989-12-15 |
| AU3271289A (en) | 1989-10-19 |
| PH25857A (en) | 1991-12-02 |
| AU601326B2 (en) | 1990-09-06 |
| DK174289A (da) | 1989-10-16 |
| DE68906707D1 (de) | 1993-07-01 |
| EP0337628A2 (en) | 1989-10-18 |
| KR920002328B1 (ko) | 1992-03-21 |
| KR890015740A (ko) | 1989-11-25 |
| ZA892622B (en) | 1990-11-28 |
| IE62751B1 (en) | 1995-02-22 |
| NZ228712A (en) | 1997-02-24 |
| PT90249B (pt) | 1994-06-30 |
| IE891171L (en) | 1989-10-13 |
| MY103872A (en) | 1993-09-30 |
| EP0337628B1 (en) | 1993-05-26 |
| DK174289D0 (da) | 1989-04-12 |
| ATE89725T1 (de) | 1993-06-15 |
| US4853409A (en) | 1989-08-01 |
| EP0337628A3 (en) | 1991-01-02 |
| CA1324762C (en) | 1993-11-30 |
| HU204996B (en) | 1992-03-30 |
| HUT52376A (en) | 1990-07-28 |
| PT90249A (pt) | 1989-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |