RU98109898A - Хиральные метилфенилоксазолидиноны - Google Patents
Хиральные метилфенилоксазолидиноныInfo
- Publication number
- RU98109898A RU98109898A RU98109898/04A RU98109898A RU98109898A RU 98109898 A RU98109898 A RU 98109898A RU 98109898/04 A RU98109898/04 A RU 98109898/04A RU 98109898 A RU98109898 A RU 98109898A RU 98109898 A RU98109898 A RU 98109898A
- Authority
- RU
- Russia
- Prior art keywords
- oxazolidinone
- methoxyphenyl
- methyl
- compounds according
- producing compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims 6
- KQTXPXFRPZUXHE-MRVPVSSYSA-N (4R)-4-methyl-3-phenyl-1,3-oxazolidin-2-one Chemical class C[C@@H]1COC(=O)N1C1=CC=CC=C1 KQTXPXFRPZUXHE-MRVPVSSYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- WOBUKEJNKOARJA-HNNXBMFYSA-N (5R)-5-(3-cyclobutyloxy-4-methoxyphenyl)-5-methyl-1,3-oxazolidin-2-one Chemical compound COC1=CC=C([C@@]2(C)OC(=O)NC2)C=C1OC1CCC1 WOBUKEJNKOARJA-HNNXBMFYSA-N 0.000 claims 1
- YPHLLMSSGKXHKR-INIZCTEOSA-N (5R)-5-(3-cyclopentyloxy-4-methoxyphenyl)-5-methyl-1,3-oxazolidin-2-one Chemical compound COC1=CC=C([C@@]2(C)OC(=O)NC2)C=C1OC1CCCC1 YPHLLMSSGKXHKR-INIZCTEOSA-N 0.000 claims 1
- NGOFATSRHLZCPW-ZDUSSCGKSA-N (5R)-5-(3-ethoxy-4-methoxyphenyl)-5-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(OC)C(OCC)=CC([C@@]2(C)OC(=O)NC2)=C1 NGOFATSRHLZCPW-ZDUSSCGKSA-N 0.000 claims 1
- PCOLSQMMKHOUQZ-NSHDSACASA-N (5R)-5-(3-hydroxy-4-methoxyphenyl)-5-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(O)C(OC)=CC=C1[C@@]1(C)OC(=O)NC1 PCOLSQMMKHOUQZ-NSHDSACASA-N 0.000 claims 1
- DJDCRHVXQOQYQI-TYZXPVIJSA-N (5R)-5-[1-(4-methoxyphenyl)propoxy]-5-methyl-1,3-oxazolidin-2-one Chemical compound C=1C=C(OC)C=CC=1C(CC)O[C@@]1(C)CNC(=O)O1 DJDCRHVXQOQYQI-TYZXPVIJSA-N 0.000 claims 1
- QDVDGPVFKYOBPD-HNNXBMFYSA-N (5R)-5-[4-methoxy-3-(2-methylprop-1-enoxy)phenyl]-5-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(OC=C(C)C)C(OC)=CC=C1[C@@]1(C)OC(=O)NC1 QDVDGPVFKYOBPD-HNNXBMFYSA-N 0.000 claims 1
- PWCQICXDXLNDSX-HNNXBMFYSA-N (5R)-5-[4-methoxy-3-(2-methylpropoxy)phenyl]-5-methyl-1,3-oxazolidin-2-one Chemical compound C1=C(OCC(C)C)C(OC)=CC=C1[C@@]1(C)OC(=O)NC1 PWCQICXDXLNDSX-HNNXBMFYSA-N 0.000 claims 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 1
- 108010001801 Tumor Necrosis Factor-alpha Proteins 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 229940079593 drugs Drugs 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
Claims (8)
1. Производные (R)-(-)-метилфенилоксазолидинона формулы I
где R обозначает углеводородный остаток с количеством С-атомов до 5.
где R обозначает углеводородный остаток с количеством С-атомов до 5.
2. Производные (R)-(-)-метилфенилоксазолидинона по п.1, представляющие собой: (R)-(-)-5-(3-циклопентилокси-4-метоксифенил)-5-метил-2-оксазолидинон, (R)-(-)-5-(3-этокси-4-метоксифенил)-5-метил-2-оксазолидинон, (R)-(-)-5-(4-метоксифенил-3-пропокси)-5-метил-2-оксазолидинон, (R)-(-)-5-(3-циклобутилокси-4-метоксифенил)-5-метил-2-оксазолидинон, (R)-(-)-5-(3-изобутенилокси-4-метоксифенил)-5-метил-2-оксазолидинон, (R)-(-)-5-(3-изобутилокси-4-метоксифенил)-5-метил-2-оксазолидинон.
3. Лекарственные средства, содержащие соединение по п.1 или 2.
4. Применение соединений по п.1 или 2 для изготовления лекарственного средства для лечения заболеваний, которые способствуют активированию фактора некроза опухоли.
5. Применение соединений по п.1 или 2 для изготовления лекарственного средства для лечения рассеянного склероза.
6. Способ получения соединений по п.1, отличающийся тем, что рацемат с оптически активным вспомогательным веществом переводят в смесь диастереомеров и затем отделяют оптически активное вспомогательное вещество.
7. Способ получения соединений по пп.1, 6, отличающийся тем, что что их рацемат хроматографируют на хиральных колонках.
8. Способ получения соединений по пп.1, 6, отличающийся тем, что (R)-(-)-5-(3-гидрокси-4-метоксифенил)-5-метил-2-оксазолидинон подвергают этерификации и затем, в случае необходимости, восстанавливают R в значении алкенила.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19540475.0 | 1995-10-20 | ||
| DE19540475A DE19540475A1 (de) | 1995-10-20 | 1995-10-20 | Chirale Methylphenyloxazolidinone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98109898A true RU98109898A (ru) | 2000-03-27 |
| RU2156243C2 RU2156243C2 (ru) | 2000-09-20 |
Family
ID=7776217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98109898/04A RU2156243C2 (ru) | 1995-10-20 | 1996-02-09 | Производные (r-)-(-)-метилфенилоксазолидинона и способ их получения |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6025376A (ru) |
| EP (1) | EP0859766B1 (ru) |
| JP (1) | JPH11513693A (ru) |
| KR (1) | KR100417359B1 (ru) |
| CN (1) | CN1077103C (ru) |
| AT (1) | ATE201203T1 (ru) |
| AU (1) | AU715344B2 (ru) |
| CZ (1) | CZ292167B6 (ru) |
| DE (2) | DE19540475A1 (ru) |
| DK (1) | DK0859766T3 (ru) |
| ES (1) | ES2158284T3 (ru) |
| FI (1) | FI980862A0 (ru) |
| GR (1) | GR3036305T3 (ru) |
| HK (1) | HK1015788A1 (ru) |
| HU (1) | HUP9802630A3 (ru) |
| IL (1) | IL117091A (ru) |
| NO (1) | NO310772B1 (ru) |
| NZ (1) | NZ301645A (ru) |
| PL (1) | PL185526B1 (ru) |
| PT (1) | PT859766E (ru) |
| RU (1) | RU2156243C2 (ru) |
| SK (1) | SK282653B6 (ru) |
| TR (1) | TR199800679T2 (ru) |
| WO (1) | WO1997015561A1 (ru) |
| ZA (1) | ZA961074B (ru) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU8747998A (en) * | 1997-08-21 | 1999-03-16 | Takeda Chemical Industries Ltd. | Anti-inflammatory agent |
| DE19928312A1 (de) * | 1999-06-16 | 2000-12-21 | Schering Ag | Arzneimittelzubereitung mit verzögerter Wirkstoffabgabe |
| US6808902B1 (en) | 1999-11-12 | 2004-10-26 | Amgen Inc. | Process for correction of a disulfide misfold in IL-1Ra Fc fusion molecules |
| EP1216700A1 (de) * | 2000-12-21 | 2002-06-26 | Schering Aktiengesellschaft | Transdermalsysteme (TDS) enthaltend (R)-(-)-Methylphenyloxazolidinon-Derivate, Inhibitoren der Phosphodiesterase IV |
| GB0111872D0 (en) * | 2001-05-15 | 2001-07-04 | Northwick Park Inst For Medica | Therapeutic agents and methods |
| WO2003002187A2 (en) * | 2001-06-26 | 2003-01-09 | Photomed Technologies, Inc. | Multiple wavelength illuminator |
| BRPI0210579B8 (pt) | 2001-06-26 | 2021-05-25 | Amgen Fremont Inc | anticorpo e composição farmacêutica |
| US20080026984A1 (en) * | 2002-02-04 | 2008-01-31 | Alfama - Investigacao E Desenvolvimento De Productos Farmaceuticos Lda | Methods for treating inflammatory disease by administering aldehydes and derivatives thereof |
| US7011854B2 (en) * | 2002-02-04 | 2006-03-14 | Alfama-Investigacao e Desenvolvimento de Produtos Farmaceuticos Lda | Method for treating a mammal by administration of a compound having the ability to release CO, compounds having the ability to release CO and pharmaceutical compositions thereof |
| US6962940B2 (en) | 2002-03-20 | 2005-11-08 | Celgene Corporation | (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof |
| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| CA2511823A1 (en) * | 2002-12-30 | 2004-07-22 | Amgen Inc. | Combination therapy with co-stimulatory factors |
| US20070207217A1 (en) * | 2003-02-03 | 2007-09-06 | Alfama - Investigacao E Desenvolvimento De Productos Farmaceuticos Lda | Method for treating a mammal by administration of a compound having the ability to release CO |
| WO2004098592A1 (ja) * | 2003-05-06 | 2004-11-18 | Senju Pharmaceutical Co. Ltd. | オキサゾリジノン誘導体含有組成物 |
| ES2251866B1 (es) | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| CA2571710A1 (en) | 2004-06-24 | 2006-11-02 | Nicholas Valiante | Small molecule immunopotentiators and assays for their detection |
| GB0601394D0 (en) | 2006-01-24 | 2006-03-01 | Hemocorm Ltd | Therapeutic delivery of carbon monoxide |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| WO2012145520A2 (en) | 2011-04-19 | 2012-10-26 | Alfama, Inc. | Carbon monoxide releasing molecules and uses thereof |
| WO2013013179A1 (en) | 2011-07-21 | 2013-01-24 | Alfama, Inc. | Ruthenium carbon monoxide releasing molecules and uses thereof |
| EP3402777B1 (en) | 2015-12-16 | 2023-12-13 | Merck Sharp & Dohme Corp. | Oxazolidinones as taro inhibitors |
| US10736905B1 (en) | 2016-09-09 | 2020-08-11 | Shahin Fatholahi | Nefopam dosage forms and methods of treatment |
| US11446311B2 (en) | 2017-09-08 | 2022-09-20 | Shahin Fatholahi | Methods for treating pain associated with sickle cell disease |
| US10736874B1 (en) | 2017-09-08 | 2020-08-11 | Shahin Fatholahi | Methods for treating pain associated with sickle cell disease |
| CA3135420A1 (en) * | 2018-04-05 | 2019-10-10 | Universiteit Hasselt | Selective pde4d inhibitors against demyelinating diseases |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2413935A1 (de) * | 1974-03-20 | 1975-10-16 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone |
| DE2541855A1 (de) * | 1975-09-18 | 1977-03-31 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone ii |
| FR2358155A1 (fr) * | 1976-07-15 | 1978-02-10 | Lapinet Eugene | Composition pour le traitement et la prevention de l'irritation et de l'inflammation de la peau, de l'oeil et des muqueuses |
| DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| DE3438839A1 (de) * | 1984-10-19 | 1986-04-24 | Schering AG, 1000 Berlin und 4709 Bergkamen | Pharmazeutische praeparate |
| US5783591A (en) * | 1984-10-19 | 1998-07-21 | Schering Aktiengesellschaft | Administration of oxazolidinone and pyrolidinone compounds for the treatment of inflammation |
| DE3639225A1 (de) * | 1986-11-14 | 1988-05-19 | Schering Ag | Verwendung von 5-(subst. phenyl)-oxazolidinonderiaten als psychopharmaka |
| AU6355190A (en) * | 1989-06-13 | 1991-01-17 | Smithkline Beecham Corporation | Inhibition of interleukin-1 and tumor necrosis factor production by monocytes and/or macrophages |
| ATE161720T1 (de) * | 1990-08-03 | 1998-01-15 | Smithkline Beecham Corp | Tnf-inhibitoren |
| PT100441A (pt) * | 1991-05-02 | 1993-09-30 | Smithkline Beecham Corp | Pirrolidinonas, seu processo de preparacao, composicoes farmaceuticas que as contem e uso |
| US5227369A (en) * | 1991-07-11 | 1993-07-13 | The Regents Of The University Of California | Compositions and methods for inhibiting leukocyte adhesion to cns myelin |
| US5532160A (en) * | 1992-02-24 | 1996-07-02 | Q. P. Corporation | Ice nucleus-forming bacterium strain Xanthomonas campestris FERM BP-4191 and process for cultivation of the same |
| GB9204808D0 (en) * | 1992-03-04 | 1992-04-15 | Rhone Poulenc Rorer Ltd | Novel compositions of matter |
| US5264437A (en) * | 1992-03-20 | 1993-11-23 | Syntex (U.S.A.) Inc. | Optionally substituted pyrido[2,3-d]pyridine-2,4(1H,3H)-diones and pyrido[2,]pyrimidine-2(1H,3H)-ones |
| US5672622A (en) * | 1994-04-21 | 1997-09-30 | Berlex Laboratories, Inc. | Treatment of multiple sclerosis |
-
1995
- 1995-10-20 DE DE19540475A patent/DE19540475A1/de not_active Withdrawn
-
1996
- 1996-02-09 CZ CZ19981201A patent/CZ292167B6/cs not_active IP Right Cessation
- 1996-02-09 RU RU98109898/04A patent/RU2156243C2/ru not_active IP Right Cessation
- 1996-02-09 ZA ZA9601074A patent/ZA961074B/xx unknown
- 1996-02-09 DE DE59606920T patent/DE59606920D1/de not_active Expired - Fee Related
- 1996-02-09 DK DK96902871T patent/DK0859766T3/da active
- 1996-02-09 SK SK495-98A patent/SK282653B6/sk unknown
- 1996-02-09 HU HU9802630A patent/HUP9802630A3/hu unknown
- 1996-02-09 IL IL11709196A patent/IL117091A/xx not_active IP Right Cessation
- 1996-02-09 AU AU47123/96A patent/AU715344B2/en not_active Ceased
- 1996-02-09 EP EP96902871A patent/EP0859766B1/de not_active Expired - Lifetime
- 1996-02-09 PL PL96326322A patent/PL185526B1/pl not_active IP Right Cessation
- 1996-02-09 AT AT96902871T patent/ATE201203T1/de not_active IP Right Cessation
- 1996-02-09 CN CN96197740A patent/CN1077103C/zh not_active Expired - Fee Related
- 1996-02-09 NZ NZ301645A patent/NZ301645A/xx unknown
- 1996-02-09 WO PCT/DE1996/000259 patent/WO1997015561A1/de active IP Right Grant
- 1996-02-09 PT PT96902871T patent/PT859766E/pt unknown
- 1996-02-09 ES ES96902871T patent/ES2158284T3/es not_active Expired - Lifetime
- 1996-02-09 JP JP9516174A patent/JPH11513693A/ja not_active Ceased
- 1996-02-09 TR TR1998/00679T patent/TR199800679T2/xx unknown
- 1996-02-09 KR KR10-1998-0702843A patent/KR100417359B1/ko not_active IP Right Cessation
- 1996-08-02 US US08/691,651 patent/US6025376A/en not_active Expired - Fee Related
-
1998
- 1998-04-15 NO NO19981688A patent/NO310772B1/no unknown
- 1998-04-17 FI FI980862A patent/FI980862A0/fi unknown
-
1999
- 1999-03-12 HK HK99101010A patent/HK1015788A1/xx not_active IP Right Cessation
-
2001
- 2001-07-31 GR GR20010401155T patent/GR3036305T3/el not_active IP Right Cessation
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