JPH07508985A - マイコバクテリウム・チュバーキュローシスに対して有効な５’−インドリニルオキサゾリジノン類 - Google Patents
マイコバクテリウム・チュバーキュローシスに対して有効な５’−インドリニルオキサゾリジノン類Info
- Publication number
- JPH07508985A JPH07508985A JP6503294A JP50329494A JPH07508985A JP H07508985 A JPH07508985 A JP H07508985A JP 6503294 A JP6503294 A JP 6503294A JP 50329494 A JP50329494 A JP 50329494A JP H07508985 A JPH07508985 A JP H07508985A
- Authority
- JP
- Japan
- Prior art keywords
- mixture
- acetamidomethyl
- tuberculosis
- oxazolidinone
- indolinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 241000187479 Mycobacterium tuberculosis Species 0.000 title claims description 6
- 201000008827 tuberculosis Diseases 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- 229940079593 drug Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 2
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 41
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- 238000011282 treatment Methods 0.000 description 14
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- LDYWVHSNDIGPHA-UHFFFAOYSA-N 3-(2,3-dihydroindol-1-yl)-1,3-oxazolidin-2-one Chemical class O=C1OCCN1N1C2=CC=CC=C2CC1 LDYWVHSNDIGPHA-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
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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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
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- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- RNJIQYVMKXWZBO-YFKPBYRVSA-N n-[[(5s)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CC(=O)NC[C@H]1CNC(=O)O1 RNJIQYVMKXWZBO-YFKPBYRVSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 206010029410 night sweats Diseases 0.000 description 1
- 230000036565 night sweats Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- WCNLCIJMFAJCPX-UHFFFAOYSA-N pethidine hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 WCNLCIJMFAJCPX-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 208000008128 pulmonary tuberculosis Diseases 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 208000013220 shortness of breath Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90938792A | 1992-07-08 | 1992-07-08 | |
| US909,387 | 1992-07-08 | ||
| PCT/US1993/004850 WO1994001110A1 (en) | 1992-07-08 | 1993-05-26 | 5'-INDOLINYL OXAZOLIDINONES USEFUL AGAINST $i(MYCOBACTERIUM TUBERCULOSIS) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07508985A true JPH07508985A (ja) | 1995-10-05 |
Family
ID=25427164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6503294A Withdrawn JPH07508985A (ja) | 1992-07-08 | 1993-05-26 | マイコバクテリウム・チュバーキュローシスに対して有効な５’−インドリニルオキサゾリジノン類 |
Country Status (9)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
| GB9702213D0 (en) | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
| GB9609919D0 (en) | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
| GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| WO1999064417A2 (en) | 1998-06-05 | 1999-12-16 | Astrazeneca Ab | Oxazolidinone derivatives, process for their preparation and pharmaceutical compositions containing them |
| GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
| GB0009803D0 (en) | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
| AR038536A1 (es) | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
| US7141588B2 (en) | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
| JP2005537301A (ja) | 2002-08-12 | 2005-12-08 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | Ｎ−アリール−２−オキサゾリジノン類及びそれらの誘導体 |
| DE60309504T2 (de) | 2002-11-21 | 2007-05-16 | Pharmacia & Upjohn Co. Llc, Kalamazoo | N-(4-(piperazin-1-yl)-phenyl-2-oxazolidinon-5-carbosäureamid-derivate und verwandte verbindungen als antibakterielle mittel |
| US7304050B2 (en) | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
| JP2023531666A (ja) | 2020-06-18 | 2023-07-25 | アカゲラ・メディスンズ，インコーポレイテッド | オキサゾリジノン化合物、オキサゾリジノン化合物を含むリポソーム組成物、およびそれらの使用方法 |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5314792A (en) * | 1976-07-24 | 1978-02-09 | Rubuobuna Buratsurabusukay Ara | Copolymers of nnvinylmethylpyrazol and diivinyl crossslinking agent and process for producing same |
| JPS54110186A (en) * | 1978-02-17 | 1979-08-29 | Tokyo Yuuki Kagaku Kougiyou Kk | Method of mamufacturing weak basic anion exchange resin |
| JPS6023854A (ja) * | 1983-07-19 | 1985-02-06 | Konishiroku Photo Ind Co Ltd | 写真要素 |
| EP0134921A1 (de) * | 1983-07-09 | 1985-03-27 | CASSELLA Aktiengesellschaft | Copolymerisat, Verfahren zu seiner Herstellung und seine Verwendung als Sorptionsmittel |
| JPS6178808A (ja) * | 1984-09-18 | 1986-04-22 | バスフ アクチェン ゲゼルシャフト | 不溶性で膨潤性の少ない粉末状重合体の製法 |
| JPS63130605A (ja) * | 1986-11-20 | 1988-06-02 | Tokuyama Soda Co Ltd | 陰イオン交換体の製造方法 |
| JPH021747A (ja) * | 1987-12-10 | 1990-01-08 | Ceskoslovenska Akad Ved | マクロ多孔性ポリマー膜及びその製造方法 |
| JPH02214711A (ja) * | 1988-12-21 | 1990-08-27 | Smith Kline Ltd | ポリビニルピリジニウムアニオン交換樹脂 |
| JPH03708A (ja) * | 1989-05-29 | 1991-01-07 | Koei Chem Co Ltd | 吸水性材料 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2865211B2 (ja) * | 1988-09-15 | 1999-03-08 | ファルマシア・アンド・アップジョン・カンパニー | ５’―インドリニル―５β―アミドメチルオキサゾリジン―２―オン類、３―（縮合環置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類および３―（窒素原子置換）フェニル―５β―アミドメチルオキサゾリジン―２―オン類 |
-
1993
- 1993-05-26 KR KR1019950700069A patent/KR950702417A/ko not_active Withdrawn
- 1993-05-26 CA CA002136324A patent/CA2136324A1/en not_active Abandoned
- 1993-05-26 JP JP6503294A patent/JPH07508985A/ja not_active Withdrawn
- 1993-05-26 WO PCT/US1993/004850 patent/WO1994001110A1/en not_active Application Discontinuation
- 1993-05-26 AU AU43865/93A patent/AU666740B2/en not_active Expired - Fee Related
- 1993-05-26 EP EP93914058A patent/EP0648119A1/en not_active Withdrawn
- 1993-06-08 TW TW082104539A patent/TW260608B/zh active
- 1993-06-23 MX MX9303764A patent/MX9303764A/es unknown
- 1993-07-02 IL IL106220A patent/IL106220A0/xx unknown
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5314792A (en) * | 1976-07-24 | 1978-02-09 | Rubuobuna Buratsurabusukay Ara | Copolymers of nnvinylmethylpyrazol and diivinyl crossslinking agent and process for producing same |
| JPS54110186A (en) * | 1978-02-17 | 1979-08-29 | Tokyo Yuuki Kagaku Kougiyou Kk | Method of mamufacturing weak basic anion exchange resin |
| EP0134921A1 (de) * | 1983-07-09 | 1985-03-27 | CASSELLA Aktiengesellschaft | Copolymerisat, Verfahren zu seiner Herstellung und seine Verwendung als Sorptionsmittel |
| JPS6023854A (ja) * | 1983-07-19 | 1985-02-06 | Konishiroku Photo Ind Co Ltd | 写真要素 |
| JPS6178808A (ja) * | 1984-09-18 | 1986-04-22 | バスフ アクチェン ゲゼルシャフト | 不溶性で膨潤性の少ない粉末状重合体の製法 |
| JPS63130605A (ja) * | 1986-11-20 | 1988-06-02 | Tokuyama Soda Co Ltd | 陰イオン交換体の製造方法 |
| JPH021747A (ja) * | 1987-12-10 | 1990-01-08 | Ceskoslovenska Akad Ved | マクロ多孔性ポリマー膜及びその製造方法 |
| JPH02214711A (ja) * | 1988-12-21 | 1990-08-27 | Smith Kline Ltd | ポリビニルピリジニウムアニオン交換樹脂 |
| JPH03708A (ja) * | 1989-05-29 | 1991-01-07 | Koei Chem Co Ltd | 吸水性材料 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4386593A (en) | 1994-01-31 |
| CA2136324A1 (en) | 1994-01-20 |
| AU666740B2 (en) | 1996-02-22 |
| TW260608B (enrdf_load_stackoverflow) | 1995-10-21 |
| WO1994001110A1 (en) | 1994-01-20 |
| IL106220A0 (en) | 1993-11-15 |
| KR950702417A (ko) | 1995-07-29 |
| EP0648119A1 (en) | 1995-04-19 |
| MX9303764A (es) | 1994-01-31 |
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