HU194192B - Process for preparing isoxazole derivatives further pharmaceutical compositions containing such compounds as active substances - Google Patents
Process for preparing isoxazole derivatives further pharmaceutical compositions containing such compounds as active substances Download PDFInfo
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- HU194192B HU194192B HU85524A HU52485A HU194192B HU 194192 B HU194192 B HU 194192B HU 85524 A HU85524 A HU 85524A HU 52485 A HU52485 A HU 52485A HU 194192 B HU194192 B HU 194192B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000002545 isoxazoles Chemical class 0.000 title description 4
- 239000013543 active substance Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 230000000202 analgesic effect Effects 0.000 claims description 18
- -1 iodo, methyl Chemical group 0.000 claims description 12
- 239000000730 antalgic agent Substances 0.000 claims description 6
- 239000002221 antipyretic Substances 0.000 claims description 5
- LYPXTDXYEQEIIN-UHFFFAOYSA-N 1,2-oxazole-4-carboxylic acid Chemical class OC(=O)C=1C=NOC=1 LYPXTDXYEQEIIN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229940125716 antipyretic agent Drugs 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
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- 206010037660 Pyrexia Diseases 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- QBPXGTUBZXXKJO-UHFFFAOYSA-N 1,2-oxazole-4-carboxamide Chemical class NC(=O)C=1C=NOC=1 QBPXGTUBZXXKJO-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
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- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Golf Clubs (AREA)
- Measuring Volume Flow (AREA)
- Apparatus For Radiation Diagnosis (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843405727 DE3405727A1 (de) | 1984-02-17 | 1984-02-17 | Isoxazol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT37767A HUT37767A (en) | 1986-02-28 |
| HU194192B true HU194192B (en) | 1988-01-28 |
Family
ID=6228020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU85524A HU194192B (en) | 1984-02-17 | 1985-02-12 | Process for preparing isoxazole derivatives further pharmaceutical compositions containing such compounds as active substances |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4636513A (en, 2012) |
| EP (1) | EP0152868B1 (en, 2012) |
| JP (1) | JPS60193973A (en, 2012) |
| KR (1) | KR850006411A (en, 2012) |
| AT (1) | ATE44142T1 (en, 2012) |
| AU (1) | AU572612B2 (en, 2012) |
| CA (1) | CA1247616A (en, 2012) |
| DE (2) | DE3405727A1 (en, 2012) |
| DK (1) | DK165981C (en, 2012) |
| ES (1) | ES8602776A1 (en, 2012) |
| FI (1) | FI81094C (en, 2012) |
| GR (1) | GR850416B (en, 2012) |
| HU (1) | HU194192B (en, 2012) |
| IL (1) | IL74351A (en, 2012) |
| MA (1) | MA20352A1 (en, 2012) |
| NO (1) | NO158677C (en, 2012) |
| NZ (1) | NZ211139A (en, 2012) |
| PH (1) | PH21434A (en, 2012) |
| PT (1) | PT79969B (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3534440A1 (de) * | 1985-09-27 | 1987-04-02 | Hoechst Ag | Arzneimittel gegen chronische graft-versus-host-krankheiten sowie gegen autoimmunerkrankungen, insbesondere systemischen lupus erythematodes |
| US5268382A (en) * | 1985-09-27 | 1993-12-07 | Hoechst Aktiengesellschaft | Medicaments to combat autoimmune diseases, in particular systemic lupus erythematosus |
| IT1228288B (it) * | 1989-01-09 | 1991-06-07 | Zambon Spa | Composti ad attivita' antiserotoninica |
| ZA913762B (en) | 1990-05-18 | 1992-01-29 | Hoechst Ag | Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides,pharmaceuticals containing these compounds and their use |
| DK0527736T3 (da) * | 1990-05-18 | 1997-10-20 | Hoechst Ag | Isoxazol-4-carboxylsyreamider og hydroxyalkyliden-cyanoacetamider, lægemidler indeholdende disse forbindelser og anvendelsen af disse lægemidler. |
| DE4127737A1 (de) | 1991-08-22 | 1993-02-25 | Hoechst Ag | Arzneimittel zur behandlung von abstossungsreaktionen bei organverpflanzungen |
| US6133301A (en) * | 1991-08-22 | 2000-10-17 | Aventis Pharma Deutschland Gmbh | Pharmaceuticals for the treatment of rejection reactions in organ transplantations |
| GB9219779D0 (en) * | 1992-09-18 | 1992-10-28 | Rhone Poulenc Agriculture | Compositions of new matter |
| US5624946A (en) * | 1994-07-05 | 1997-04-29 | Williams; James | Use of leflunomide to control and reverse chronic allograft rejection |
| DE59912559D1 (de) | 1999-07-02 | 2005-10-20 | Cognis Ip Man Gmbh | Mikrokapseln - III |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE634286C (de) * | 1935-02-23 | 1936-08-26 | Hoffmann La Roche & Co Akt Ges | Verfahren zur Herstellung dialkylsubstituierter Amide von Isoxazolcarbonsaeuren |
| US2126329A (en) * | 1936-03-20 | 1938-08-09 | Hoffmann La Roche | Amide derivatives of isoxazole carboxylic acids |
| DE653835C (de) * | 1936-03-20 | 1937-12-03 | Hoffmanni La Roche & Co Akt Ge | Verfahren zur Darstellung amidartiger Abkoemmlinge von Isoxazolcarbonsaeuren |
| US2212767A (en) * | 1938-01-17 | 1940-08-27 | Hoffmann La Roche | Amide derivatives of 3,5-dimethylisoxazole carboxylic acids |
| DE2524959C2 (de) * | 1975-06-05 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | 5-Methyl-isoxazol-4-carbonsäureanilide, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende Mittel |
-
1984
- 1984-02-17 DE DE19843405727 patent/DE3405727A1/de not_active Withdrawn
-
1985
- 1985-02-07 AT AT85101264T patent/ATE44142T1/de not_active IP Right Cessation
- 1985-02-07 EP EP85101264A patent/EP0152868B1/de not_active Expired
- 1985-02-07 DE DE8585101264T patent/DE3571130D1/de not_active Expired
- 1985-02-12 HU HU85524A patent/HU194192B/hu not_active IP Right Cessation
- 1985-02-14 FI FI850613A patent/FI81094C/fi not_active IP Right Cessation
- 1985-02-14 NO NO850580A patent/NO158677C/no unknown
- 1985-02-15 ES ES540438A patent/ES8602776A1/es not_active Expired
- 1985-02-15 IL IL74351A patent/IL74351A/xx not_active IP Right Cessation
- 1985-02-15 PH PH31872A patent/PH21434A/en unknown
- 1985-02-15 CA CA000474482A patent/CA1247616A/en not_active Expired
- 1985-02-15 NZ NZ211139A patent/NZ211139A/en unknown
- 1985-02-15 DK DK074085A patent/DK165981C/da active
- 1985-02-15 PT PT79969A patent/PT79969B/pt not_active IP Right Cessation
- 1985-02-15 JP JP60026671A patent/JPS60193973A/ja active Granted
- 1985-02-15 MA MA20576A patent/MA20352A1/fr unknown
- 1985-02-15 US US06/702,312 patent/US4636513A/en not_active Expired - Fee Related
- 1985-02-15 GR GR850416A patent/GR850416B/el unknown
- 1985-02-15 AU AU38785/85A patent/AU572612B2/en not_active Ceased
- 1985-02-16 KR KR1019850000966A patent/KR850006411A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP0152868A2 (de) | 1985-08-28 |
| IL74351A0 (en) | 1985-05-31 |
| FI850613L (fi) | 1985-08-18 |
| KR850006411A (ko) | 1985-10-05 |
| GR850416B (en, 2012) | 1985-06-18 |
| DE3405727A1 (de) | 1985-08-22 |
| DK74085A (da) | 1985-08-18 |
| EP0152868B1 (de) | 1989-06-21 |
| ES540438A0 (es) | 1985-12-01 |
| NO158677C (no) | 1988-10-19 |
| ATE44142T1 (de) | 1989-07-15 |
| HUT37767A (en) | 1986-02-28 |
| NZ211139A (en) | 1988-04-29 |
| CA1247616A (en) | 1988-12-28 |
| FI81094C (fi) | 1990-09-10 |
| NO850580L (no) | 1985-08-19 |
| FI850613A0 (fi) | 1985-02-14 |
| DE3571130D1 (en) | 1989-07-27 |
| PH21434A (en) | 1987-10-15 |
| FI81094B (fi) | 1990-05-31 |
| AU572612B2 (en) | 1988-05-12 |
| AU3878585A (en) | 1985-09-05 |
| DK165981B (da) | 1993-02-22 |
| EP0152868A3 (en) | 1986-10-08 |
| IL74351A (en) | 1988-11-15 |
| US4636513A (en) | 1987-01-13 |
| ES8602776A1 (es) | 1985-12-01 |
| PT79969B (de) | 1987-02-02 |
| PT79969A (de) | 1985-03-01 |
| JPS60193973A (ja) | 1985-10-02 |
| MA20352A1 (fr) | 1985-10-01 |
| NO158677B (no) | 1988-07-11 |
| DK74085D0 (da) | 1985-02-15 |
| JPH03866B2 (en, 2012) | 1991-01-09 |
| DK165981C (da) | 1993-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |