HU199132B - Process for producing 1,3-oxazolidin-2-one derivatives and pharmaceutical compositions comprising such compounds as active ingredient - Google Patents
Process for producing 1,3-oxazolidin-2-one derivatives and pharmaceutical compositions comprising such compounds as active ingredient Download PDFInfo
- Publication number
- HU199132B HU199132B HU852082A HU208285A HU199132B HU 199132 B HU199132 B HU 199132B HU 852082 A HU852082 A HU 852082A HU 208285 A HU208285 A HU 208285A HU 199132 B HU199132 B HU 199132B
- Authority
- HU
- Hungary
- Prior art keywords
- compound
- oxazolidin
- phenyl
- formula
- methyl
- Prior art date
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- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 title claims description 106
- 238000000034 method Methods 0.000 title claims description 28
- 230000008569 process Effects 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 239000004480 active ingredient Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims description 2
- 206010029897 Obsessive thoughts Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 210000002435 tendon Anatomy 0.000 description 26
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- -1 1-methyl Chemical group 0.000 description 17
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
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- 101100310222 Caenorhabditis briggsae she-1 gene Proteins 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
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- 235000011152 sodium sulphate Nutrition 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
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- 206010044565 Tremor Diseases 0.000 description 4
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
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- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
- LDKKNKGQVRSJTJ-UHFFFAOYSA-N 5-phenyl-3-(3-piperidin-1-ylpropyl)-4-propan-2-yl-1,3-oxazolidin-2-one Chemical compound CC(C)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 LDKKNKGQVRSJTJ-UHFFFAOYSA-N 0.000 description 3
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- YYHKDAYVJJZHEN-NWDGAFQWSA-N (4s,5r)-4-(2-methylpropyl)-5-phenyl-1,3-oxazolidin-2-one Chemical compound CC(C)C[C@@H]1NC(=O)O[C@@H]1C1=CC=CC=C1 YYHKDAYVJJZHEN-NWDGAFQWSA-N 0.000 description 2
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- CBHDABYZJQLLTK-UHFFFAOYSA-N 3-[3-(azepan-1-yl)propyl]-4-hexyl-5-phenyl-1,3-oxazolidin-2-one Chemical compound CCCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCCC1 CBHDABYZJQLLTK-UHFFFAOYSA-N 0.000 description 2
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- ABZZCQSSDIPILA-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CCC(C)(C)C1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 ABZZCQSSDIPILA-UHFFFAOYSA-N 0.000 description 2
- AXRKILQEHPABMB-UHFFFAOYSA-N 4-(2-methylpropyl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 AXRKILQEHPABMB-UHFFFAOYSA-N 0.000 description 2
- LGAQJDJFDNJSME-UHFFFAOYSA-N 4-(2-methylpropyl)-5-phenyl-3-(3-pyrrolidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCC1 LGAQJDJFDNJSME-UHFFFAOYSA-N 0.000 description 2
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- OOBBCXZWSAKESQ-UHFFFAOYSA-N 4-(4-methylpentyl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OOBBCXZWSAKESQ-UHFFFAOYSA-N 0.000 description 2
- OGJFJARREZDRDX-UHFFFAOYSA-N 4-(5-methylhexyl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OGJFJARREZDRDX-UHFFFAOYSA-N 0.000 description 2
- OFBIBBBFSZWAGQ-UHFFFAOYSA-N 4-(6-methylheptyl)-5-phenyl-3-(3-piperidin-1-ylpropyl)-1,3-oxazolidin-2-one Chemical compound CC(C)CCCCCC1C(C=2C=CC=CC=2)OC(=O)N1CCCN1CCCCC1 OFBIBBBFSZWAGQ-UHFFFAOYSA-N 0.000 description 2
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000028161 membrane depolarization Effects 0.000 description 1
- ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59203624A JPS6183170A (ja) | 1984-09-28 | 1984-09-28 | 新規な１，３−オキサゾリジン−２−オン誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT39168A HUT39168A (en) | 1986-08-28 |
| HU199132B true HU199132B (en) | 1990-01-29 |
Family
ID=16477122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU852082A HU199132B (en) | 1984-09-28 | 1985-05-30 | Process for producing 1,3-oxazolidin-2-one derivatives and pharmaceutical compositions comprising such compounds as active ingredient |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4644063A (enExample) |
| JP (1) | JPS6183170A (enExample) |
| KR (1) | KR900004323B1 (enExample) |
| AR (1) | AR240924A1 (enExample) |
| AT (1) | AT392069B (enExample) |
| AU (1) | AU566419B2 (enExample) |
| BR (1) | BR8502707A (enExample) |
| CA (1) | CA1252092A (enExample) |
| CH (1) | CH663207A5 (enExample) |
| CS (1) | CS273606B2 (enExample) |
| DE (1) | DE3519261C2 (enExample) |
| DK (1) | DK165952C (enExample) |
| ES (2) | ES8800571A1 (enExample) |
| FR (1) | FR2571052B1 (enExample) |
| GB (2) | GB8512975D0 (enExample) |
| HU (1) | HU199132B (enExample) |
| IN (1) | IN162060B (enExample) |
| IT (1) | IT1208807B (enExample) |
| MX (2) | MX161397A (enExample) |
| MY (1) | MY102081A (enExample) |
| NL (1) | NL193191C (enExample) |
| NZ (1) | NZ212143A (enExample) |
| PH (1) | PH20852A (enExample) |
| RO (1) | RO91422B (enExample) |
| SE (1) | SE463100B (enExample) |
| SU (2) | SU1402263A3 (enExample) |
| ZA (1) | ZA854001B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6183147A (ja) * | 1984-09-28 | 1986-04-26 | Nippon Chemiphar Co Ltd | 新規なアミノアルコール誘導体およびその製造法並びにそれを有効成分とするグルタミン酸遮断剤 |
| JPH0759570B2 (ja) * | 1986-05-06 | 1995-06-28 | 三井東圧化学株式会社 | ２−オキサゾリジノン類の製造方法 |
| JPH0713017B2 (ja) * | 1986-06-18 | 1995-02-15 | 日本ケミファ株式会社 | 脳細胞保護作用を有する医薬組成物 |
| DE3877470T2 (de) * | 1987-09-10 | 1993-06-24 | Merck Sharp & Dohme | Oxazole und thiazole zur behandlung seniler demenz. |
| DE68915595T2 (de) * | 1988-03-24 | 1994-09-15 | Sankyo Co | Verwendung von Isoxazolinonen als cerebro-aktive Medikamente. |
| JPH0314562A (ja) * | 1988-04-11 | 1991-01-23 | Nippon Chemiphar Co Ltd | 新規なアルキレンジアミン誘導体およびグルタミン酸遮断剤 |
| US5187171A (en) * | 1989-01-09 | 1993-02-16 | G. D. Searle & Co. | Use of a glycine b partial agonist as an antipsychotic |
| DE69320730T2 (de) * | 1992-07-14 | 1999-02-11 | Nippon Chemiphar Co. Ltd., Tokio/Tokyo | Alkylendiaminderivate |
| NZ314207A (en) * | 1992-09-28 | 2000-12-22 | Vertex Pharma | 1-(2-Oxoacetyl)-piperidine-2-carboxylic acid derivatives as multi drug resistant cancer cell sensitizers |
| ES2111326T3 (es) * | 1993-09-15 | 1998-03-01 | Merck Sharp & Dohme | Derivados de imidazolona y oxazolona como antagonistas de dopamina. |
| DE4425613A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
| FR2729954B1 (fr) * | 1995-01-30 | 1997-08-01 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
| DE19516483A1 (de) * | 1995-05-05 | 1996-11-07 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten |
| US6037354A (en) | 1997-06-18 | 2000-03-14 | Merck & Co., Inc. | Alpha 1a adrenergic receptor antagonists |
| BR112015021940A2 (pt) | 2013-03-14 | 2017-07-18 | Akzo Nobel Chemicals Int Bv | composição agrícola que compreende pelo menos uma substância química agrícola e pelo menos um éter de celulose; método de redução do desvio de pulverização durante a pulverização de uma solução aquosa; e método de aumento da resistência à lavagem pela chuva de uma solução aquosa pulverizada sobre uma superfície |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437389A (en) * | 1948-03-09 | Oxazoeidones and erocesstok | ||
| DE1135461B (de) * | 1959-05-08 | 1962-08-30 | Knoll Ag | Verfahren zur Herstellung von basisch substituierten Phthalimidinen |
| FR1301267A (fr) * | 1961-04-04 | 1962-08-17 | Science Union Et Compagnie Soc | Nouveaux dérivés de l'oxazolidinone-2 et leurs procédés de préparation |
| US3131197A (en) * | 1963-03-13 | 1964-04-28 | Smith Kline French Lab | 5-(3, 4-carbonyldioxyphenyl)-3-isopropyl-2-oxazolidone |
| US3576808A (en) * | 1967-09-15 | 1971-04-27 | Miles Lab | N-4-phenyl-1-piperazinylalkyl-5-phenyl-oxazolidinones |
| GB1222708A (en) * | 1968-10-22 | 1971-02-17 | Delalande Sa | Novel 5-(n-substituted aminomethyl)-2-oxazolidinones and their process of preparation |
| FR2179582B1 (enExample) * | 1972-04-13 | 1975-10-10 | Synthelabo |
-
1984
- 1984-09-28 JP JP59203624A patent/JPS6183170A/ja active Granted
-
1985
- 1985-05-21 NZ NZ212143A patent/NZ212143A/en unknown
- 1985-05-22 SE SE8502525A patent/SE463100B/sv not_active IP Right Cessation
- 1985-05-22 GB GB858512975A patent/GB8512975D0/en active Pending
- 1985-05-23 IN IN382/MAS/85A patent/IN162060B/en unknown
- 1985-05-23 DK DK230185A patent/DK165952C/da not_active IP Right Cessation
- 1985-05-24 DE DE3519261A patent/DE3519261C2/de not_active Expired - Fee Related
- 1985-05-24 PH PH32310A patent/PH20852A/en unknown
- 1985-05-27 ES ES543517A patent/ES8800571A1/es not_active Expired
- 1985-05-27 ZA ZA854001A patent/ZA854001B/xx unknown
- 1985-05-28 CA CA000482506A patent/CA1252092A/en not_active Expired
- 1985-05-29 US US06/739,059 patent/US4644063A/en not_active Expired - Lifetime
- 1985-05-29 KR KR1019850003726A patent/KR900004323B1/ko not_active Expired
- 1985-05-30 HU HU852082A patent/HU199132B/hu not_active IP Right Cessation
- 1985-05-30 GB GB08513685A patent/GB2165237B/en not_active Expired
- 1985-05-30 RO RO118984A patent/RO91422B/ro unknown
- 1985-05-30 SU SU853902250A patent/SU1402263A3/ru active
- 1985-05-30 IT IT8567500A patent/IT1208807B/it active
- 1985-05-30 FR FR8508128A patent/FR2571052B1/fr not_active Expired
- 1985-05-31 MX MX205493A patent/MX161397A/es unknown
- 1985-05-31 AR AR300604A patent/AR240924A1/es active
- 1985-05-31 CH CH2317/85A patent/CH663207A5/fr not_active IP Right Cessation
- 1985-05-31 AT AT0165685A patent/AT392069B/de not_active IP Right Cessation
- 1985-05-31 NL NL8501579A patent/NL193191C/nl not_active IP Right Cessation
- 1985-05-31 CS CS392785A patent/CS273606B2/cs unknown
- 1985-05-31 BR BR8502707A patent/BR8502707A/pt not_active IP Right Cessation
- 1985-07-09 AU AU44697/85A patent/AU566419B2/en not_active Ceased
-
1986
- 1986-05-13 SU SU864027452A patent/SU1431679A3/ru active
- 1986-09-18 ES ES557075A patent/ES8802152A1/es not_active Expired
-
1987
- 1987-09-29 MY MYPI87002215A patent/MY102081A/en unknown
-
1990
- 1990-07-16 MX MX2159290A patent/MX21592A/es unknown
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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 |