SE453194B - Rifamycinderivat, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande dessa - Google Patents
Rifamycinderivat, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande dessaInfo
- Publication number
- SE453194B SE453194B SE8100743A SE8100743A SE453194B SE 453194 B SE453194 B SE 453194B SE 8100743 A SE8100743 A SE 8100743A SE 8100743 A SE8100743 A SE 8100743A SE 453194 B SE453194 B SE 453194B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- formula
- rifamycin
- represent
- amino
- Prior art date
Links
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical class OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- -1 hexahydroazepinyb Chemical group 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QBRFPWPICDILII-WVKYYCEASA-N 3-amino-4-iminorifamycin-s Chemical compound O=C1C(C(O)=C2C)=C3C(N)=C(N)C1=NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O QBRFPWPICDILII-WVKYYCEASA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 5
- 229940109171 rifamycin sv Drugs 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8004848 | 1980-02-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8100743L SE8100743L (sv) | 1981-08-14 |
| SE453194B true SE453194B (sv) | 1988-01-18 |
Family
ID=10511321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8100743A SE453194B (sv) | 1980-02-13 | 1981-01-30 | Rifamycinderivat, forfarande for framstellning derav samt farmaceutiska kompositioner innehallande dessa |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4305941A (en]) |
| JP (1) | JPS56128785A (en]) |
| AT (1) | AT373891B (en]) |
| AU (1) | AU533176B2 (en]) |
| BE (1) | BE886395A (en]) |
| CA (1) | CA1173030A (en]) |
| CH (1) | CH649770A5 (en]) |
| DE (1) | DE3100612A1 (en]) |
| DK (1) | DK11381A (en]) |
| ES (1) | ES8202030A1 (en]) |
| FI (1) | FI69079C (en]) |
| FR (1) | FR2475552A1 (en]) |
| GR (1) | GR71862B (en]) |
| IE (1) | IE51144B1 (en]) |
| IL (1) | IL61861A (en]) |
| IT (1) | IT1136558B (en]) |
| NL (1) | NL8100695A (en]) |
| NZ (1) | NZ195943A (en]) |
| PT (1) | PT72499B (en]) |
| SE (1) | SE453194B (en]) |
| SU (1) | SU1047391A3 (en]) |
| YU (1) | YU31781A (en]) |
| ZA (1) | ZA8140B (en]) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1201963B (it) * | 1983-03-24 | 1989-02-02 | Prodotti Antibiotici Spa | Derivati delle rifamicine e procedimento per la loro preparazione |
| GB8308166D0 (en) * | 1983-03-24 | 1983-05-05 | Erba Farmitalia | Preparation of azinomethyl-rifamycins |
| WO2003045319A2 (en) * | 2001-11-21 | 2003-06-05 | Activbiotics, Inc. | Targeted therapeutics and uses thereof |
| US7820652B2 (en) * | 2003-09-24 | 2010-10-26 | Activbiotics Pharma, Llc | Regimen for the administration of rifamycin-class antibiotics |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1048565B (it) * | 1975-05-15 | 1980-12-20 | Archifar Ind Chim Trentino | Amine aromatiche |
| IT1056271B (it) * | 1975-05-20 | 1982-01-30 | Archifar Ind Chim Trentino | Prodotti derivati dalle amine aromatiche |
| IT1056272B (it) * | 1975-06-13 | 1982-01-30 | Archifar Ind Chim Trentino | Prodotti derivati dalle amine aromatiche |
| DK345977A (da) * | 1976-09-30 | 1978-03-31 | Archifar Ind Chim Trentino | G rifamycinforbindelser og fremgangsmaade til deres fremstillin |
-
1980
- 1980-11-28 BE BE0/202966A patent/BE886395A/fr not_active IP Right Cessation
-
1981
- 1981-01-05 IE IE4/81A patent/IE51144B1/en unknown
- 1981-01-05 US US06/222,618 patent/US4305941A/en not_active Expired - Fee Related
- 1981-01-05 ZA ZA00810040A patent/ZA8140B/xx unknown
- 1981-01-06 NZ NZ195943A patent/NZ195943A/xx unknown
- 1981-01-06 IL IL61861A patent/IL61861A/xx unknown
- 1981-01-08 GR GR63818A patent/GR71862B/el unknown
- 1981-01-08 FI FI810038A patent/FI69079C/fi not_active IP Right Cessation
- 1981-01-12 DE DE19813100612 patent/DE3100612A1/de not_active Ceased
- 1981-01-12 DK DK11381A patent/DK11381A/da not_active Application Discontinuation
- 1981-01-14 CH CH207/81A patent/CH649770A5/it not_active IP Right Cessation
- 1981-01-19 IT IT19187/81A patent/IT1136558B/it active
- 1981-01-23 AT AT0028181A patent/AT373891B/de not_active IP Right Cessation
- 1981-01-23 SU SU813232526A patent/SU1047391A3/ru active
- 1981-01-23 FR FR8101219A patent/FR2475552A1/fr active Granted
- 1981-01-30 SE SE8100743A patent/SE453194B/sv not_active IP Right Cessation
- 1981-02-05 CA CA000370178A patent/CA1173030A/en not_active Expired
- 1981-02-06 YU YU00317/81A patent/YU31781A/xx unknown
- 1981-02-12 ES ES499356A patent/ES8202030A1/es not_active Expired
- 1981-02-12 NL NL8100695A patent/NL8100695A/nl not_active Application Discontinuation
- 1981-02-12 AU AU67253/81A patent/AU533176B2/en not_active Ceased
- 1981-02-12 PT PT72499A patent/PT72499B/pt unknown
- 1981-02-13 JP JP1913381A patent/JPS56128785A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI69079C (fi) | 1985-12-10 |
| CH649770A5 (it) | 1985-06-14 |
| CA1173030A (en) | 1984-08-21 |
| AT373891B (de) | 1984-02-27 |
| IT8119187A0 (it) | 1981-01-19 |
| PT72499A (en) | 1981-03-01 |
| PT72499B (en) | 1982-02-05 |
| ES499356A0 (es) | 1982-01-16 |
| NL8100695A (nl) | 1981-09-16 |
| ATA28181A (de) | 1983-07-15 |
| IE51144B1 (en) | 1986-10-15 |
| GR71862B (en]) | 1983-07-06 |
| JPS6155918B2 (en]) | 1986-11-29 |
| YU31781A (en) | 1983-09-30 |
| IE810004L (en) | 1981-08-13 |
| US4305941A (en) | 1981-12-15 |
| NZ195943A (en) | 1982-12-07 |
| BE886395A (fr) | 1981-03-16 |
| SE8100743L (sv) | 1981-08-14 |
| FR2475552B1 (en]) | 1985-02-15 |
| ZA8140B (en) | 1982-01-27 |
| JPS56128785A (en) | 1981-10-08 |
| AU533176B2 (en) | 1983-11-03 |
| IL61861A0 (en) | 1981-02-27 |
| SU1047391A3 (ru) | 1983-10-07 |
| DE3100612A1 (de) | 1981-12-03 |
| ES8202030A1 (es) | 1982-01-16 |
| FR2475552A1 (fr) | 1981-08-14 |
| FI810038L (fi) | 1981-08-14 |
| DK11381A (da) | 1981-08-14 |
| IL61861A (en) | 1984-03-30 |
| FI69079B (fi) | 1985-08-30 |
| AU6725381A (en) | 1981-08-20 |
| IT1136558B (it) | 1986-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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