FI69079C - Foerfarande foer framstaellning av rifamycinderivat med antibakterisk aktivitet - Google Patents
Foerfarande foer framstaellning av rifamycinderivat med antibakterisk aktivitet Download PDFInfo
- Publication number
- FI69079C FI69079C FI810038A FI810038A FI69079C FI 69079 C FI69079 C FI 69079C FI 810038 A FI810038 A FI 810038A FI 810038 A FI810038 A FI 810038A FI 69079 C FI69079 C FI 69079C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- amino
- oco
- solution
- added
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- -1 morpholino, hexahydroazepinyl Chemical group 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 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 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 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 6
- 238000000034 method Methods 0.000 description 5
- 229940109171 rifamycin sv Drugs 0.000 description 5
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 4
- 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
- HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000013207 serial dilution Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241001522878 Escherichia coli B Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 229930189077 Rifamycin Natural products 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 229960003292 rifamycin Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Veterinary Medicine (AREA)
- Oncology (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8004848 | 1980-02-13 | ||
| GB8004848 | 1980-02-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810038L FI810038L (fi) | 1981-08-14 |
| FI69079B FI69079B (fi) | 1985-08-30 |
| FI69079C true FI69079C (fi) | 1985-12-10 |
Family
ID=10511321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810038A FI69079C (fi) | 1980-02-13 | 1981-01-08 | Foerfarande foer framstaellning av rifamycinderivat med antibakterisk aktivitet |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4305941A (en, 2012) |
| JP (1) | JPS56128785A (en, 2012) |
| AT (1) | AT373891B (en, 2012) |
| AU (1) | AU533176B2 (en, 2012) |
| BE (1) | BE886395A (en, 2012) |
| CA (1) | CA1173030A (en, 2012) |
| CH (1) | CH649770A5 (en, 2012) |
| DE (1) | DE3100612A1 (en, 2012) |
| DK (1) | DK11381A (en, 2012) |
| ES (1) | ES8202030A1 (en, 2012) |
| FI (1) | FI69079C (en, 2012) |
| FR (1) | FR2475552A1 (en, 2012) |
| GR (1) | GR71862B (en, 2012) |
| IE (1) | IE51144B1 (en, 2012) |
| IL (1) | IL61861A (en, 2012) |
| IT (1) | IT1136558B (en, 2012) |
| NL (1) | NL8100695A (en, 2012) |
| NZ (1) | NZ195943A (en, 2012) |
| PT (1) | PT72499B (en, 2012) |
| SE (1) | SE453194B (en, 2012) |
| SU (1) | SU1047391A3 (en, 2012) |
| YU (1) | YU31781A (en, 2012) |
| ZA (1) | ZA8140B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8308166D0 (en) * | 1983-03-24 | 1983-05-05 | Erba Farmitalia | Preparation of azinomethyl-rifamycins |
| IT1201963B (it) * | 1983-03-24 | 1989-02-02 | Prodotti Antibiotici Spa | Derivati delle rifamicine e procedimento per la loro preparazione |
| US7122525B2 (en) * | 2001-11-21 | 2006-10-17 | 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 ZA ZA00810040A patent/ZA8140B/xx unknown
- 1981-01-05 US US06/222,618 patent/US4305941A/en not_active Expired - Fee Related
- 1981-01-06 IL IL61861A patent/IL61861A/xx unknown
- 1981-01-06 NZ NZ195943A patent/NZ195943A/xx unknown
- 1981-01-08 FI FI810038A patent/FI69079C/fi not_active IP Right Cessation
- 1981-01-08 GR GR63818A patent/GR71862B/el unknown
- 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 FR FR8101219A patent/FR2475552A1/fr active Granted
- 1981-01-23 AT AT0028181A patent/AT373891B/de not_active IP Right Cessation
- 1981-01-23 SU SU813232526A patent/SU1047391A3/ru active
- 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 AU AU67253/81A patent/AU533176B2/en not_active Ceased
- 1981-02-12 ES ES499356A patent/ES8202030A1/es not_active Expired
- 1981-02-12 PT PT72499A patent/PT72499B/pt unknown
- 1981-02-12 NL NL8100695A patent/NL8100695A/nl not_active Application Discontinuation
- 1981-02-13 JP JP1913381A patent/JPS56128785A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1173030A (en) | 1984-08-21 |
| IE51144B1 (en) | 1986-10-15 |
| DK11381A (da) | 1981-08-14 |
| ES499356A0 (es) | 1982-01-16 |
| NZ195943A (en) | 1982-12-07 |
| IL61861A (en) | 1984-03-30 |
| BE886395A (fr) | 1981-03-16 |
| SU1047391A3 (ru) | 1983-10-07 |
| YU31781A (en) | 1983-09-30 |
| IL61861A0 (en) | 1981-02-27 |
| IT1136558B (it) | 1986-09-03 |
| US4305941A (en) | 1981-12-15 |
| FI810038L (fi) | 1981-08-14 |
| AU6725381A (en) | 1981-08-20 |
| FI69079B (fi) | 1985-08-30 |
| SE453194B (sv) | 1988-01-18 |
| ATA28181A (de) | 1983-07-15 |
| JPS6155918B2 (en, 2012) | 1986-11-29 |
| DE3100612A1 (de) | 1981-12-03 |
| AT373891B (de) | 1984-02-27 |
| PT72499A (en) | 1981-03-01 |
| PT72499B (en) | 1982-02-05 |
| ZA8140B (en) | 1982-01-27 |
| FR2475552A1 (fr) | 1981-08-14 |
| FR2475552B1 (en, 2012) | 1985-02-15 |
| NL8100695A (nl) | 1981-09-16 |
| IE810004L (en) | 1981-08-13 |
| JPS56128785A (en) | 1981-10-08 |
| GR71862B (en, 2012) | 1983-07-06 |
| SE8100743L (sv) | 1981-08-14 |
| AU533176B2 (en) | 1983-11-03 |
| CH649770A5 (it) | 1985-06-14 |
| IT8119187A0 (it) | 1981-01-19 |
| ES8202030A1 (es) | 1982-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: FARMITALIA CARLO ERBA S.P.A. |