CH622022A5 - - Google Patents
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- Publication number
- CH622022A5 CH622022A5 CH568376A CH568376A CH622022A5 CH 622022 A5 CH622022 A5 CH 622022A5 CH 568376 A CH568376 A CH 568376A CH 568376 A CH568376 A CH 568376A CH 622022 A5 CH622022 A5 CH 622022A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- rifamycin
- compound
- hours
- acetic acid
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- SMPJCQGFZSDIHE-GVDHMVJUSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-amino-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C(N)=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 SMPJCQGFZSDIHE-GVDHMVJUSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 239000011701 zinc Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound 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 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 229930189077 Rifamycin Natural products 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 229960003292 rifamycin Drugs 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 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
- 238000003756 stirring Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000001663 electronic absorption spectrum Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- XFVYSNJVWMMLIE-LONSXKSTSA-N tetrahydrorifamycin s Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)C(C)CCC[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 XFVYSNJVWMMLIE-LONSXKSTSA-N 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-SVYQBANQSA-N (2H8)-1,4-Dioxane Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])OC1([2H])[2H] RYHBNJHYFVUHQT-SVYQBANQSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- BCNLNCHALTVDMC-UHFFFAOYSA-N benzene;methanol;4-methylpentan-2-one Chemical compound OC.C1=CC=CC=C1.CC(C)CC(C)=O BCNLNCHALTVDMC-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- -1 rifamycin compound Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 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 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000008096 xylene Substances 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
- C07D498/02—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 two hetero rings
- C07D498/08—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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT05155/75A IT1048565B (it) | 1975-05-15 | 1975-05-15 | Amine aromatiche |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622022A5 true CH622022A5 (fr) | 1981-03-13 |
Family
ID=11118523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH568376A CH622022A5 (fr) | 1975-05-15 | 1976-05-06 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4017481A (fr) |
| JP (1) | JPS51141897A (fr) |
| AR (1) | AR211013A1 (fr) |
| AT (1) | AT343808B (fr) |
| BE (1) | BE841548A (fr) |
| CA (1) | CA1057749A (fr) |
| CH (1) | CH622022A5 (fr) |
| DE (1) | DE2620782C2 (fr) |
| DK (1) | DK215676A (fr) |
| ES (1) | ES448421A1 (fr) |
| FI (1) | FI761176A (fr) |
| FR (1) | FR2311018A1 (fr) |
| GB (1) | GB1534075A (fr) |
| HU (1) | HU171395B (fr) |
| IE (1) | IE42980B1 (fr) |
| IL (1) | IL49516A (fr) |
| IN (1) | IN143142B (fr) |
| IT (1) | IT1048565B (fr) |
| NL (1) | NL7605142A (fr) |
| NO (1) | NO761681L (fr) |
| PT (1) | PT65102B (fr) |
| SE (1) | SE7604755L (fr) |
| SU (1) | SU598565A3 (fr) |
| ZA (1) | ZA762553B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK345977A (da) * | 1976-09-30 | 1978-03-31 | Archifar Ind Chim Trentino | G rifamycinforbindelser og fremgangsmaade til deres fremstillin |
| CH629212A5 (it) * | 1976-10-18 | 1982-04-15 | Erba Farmitalia | Procedimento per la preparazione di composti di rifamicina. |
| GB1576886A (en) * | 1977-04-20 | 1980-10-15 | Lepetit Spa | Rifamycin derivatives |
| IT1090772B (it) * | 1977-12-20 | 1985-06-26 | Alfa Farmaceutici Spa | Derivati della rifamicina e procedimento per la loro preparazione |
| BE886395A (fr) * | 1980-02-13 | 1981-03-16 | Erba Farmitalia | Derives de rifamycine |
| DE3228883A1 (de) * | 1981-08-26 | 1983-03-10 | Hydrocarbon Research Inc., 08648 Lawrenceville, N.J. | Verfahren zur herstellung von d-fructose |
| IT1201963B (it) * | 1983-03-24 | 1989-02-02 | Prodotti Antibiotici Spa | Derivati delle rifamicine e procedimento per la loro preparazione |
| US4631290A (en) * | 1985-08-29 | 1986-12-23 | American Home Products Corporation | Method of treating hepatitis |
| US4743619A (en) * | 1985-08-29 | 1988-05-10 | American Home Products Corporation | Method of treating hepatitis |
| WO2003045319A2 (fr) * | 2001-11-21 | 2003-06-05 | Activbiotics, Inc. | Agents therapeutiques cibles et leurs utilisations |
| US7820652B2 (en) * | 2003-09-24 | 2010-10-26 | Activbiotics Pharma, Llc | Regimen for the administration of rifamycin-class antibiotics |
| ITMI20071435A1 (it) * | 2007-07-17 | 2009-01-18 | Segix Italia Srl | Nuovi farmaci ad attivita' anticolestatica |
| CN105001236B (zh) * | 2015-06-26 | 2017-05-31 | 重庆华邦制药有限公司 | 3‑氨基‑利福霉素s的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH512510A (de) * | 1965-08-24 | 1971-09-15 | Ciba Geigy Ag | Verfahren zur Herstellung von in 3-Stellung durch eine unsubstituierte oder substituierte Aminogruppe substituierten Derivaten von Rifamycin-S und Rifamycin-SV |
| GB1316689A (en) * | 1971-01-18 | 1973-05-09 | Lepetit Spa | Trifamycin derivatives |
-
1975
- 1975-05-15 IT IT05155/75A patent/IT1048565B/it active
-
1976
- 1976-04-23 IE IE856/76A patent/IE42980B1/en unknown
- 1976-04-26 SE SE7604755A patent/SE7604755L/xx unknown
- 1976-04-27 US US05/680,771 patent/US4017481A/en not_active Expired - Lifetime
- 1976-04-27 GB GB16969/76A patent/GB1534075A/en not_active Expired
- 1976-04-28 ZA ZA762553A patent/ZA762553B/xx unknown
- 1976-04-28 FI FI761176A patent/FI761176A/fi not_active Application Discontinuation
- 1976-04-30 IN IN763/CAL/76A patent/IN143142B/en unknown
- 1976-05-03 CA CA251,689A patent/CA1057749A/fr not_active Expired
- 1976-05-03 IL IL49516A patent/IL49516A/xx unknown
- 1976-05-05 AR AR263203A patent/AR211013A1/es active
- 1976-05-06 BE BE166810A patent/BE841548A/fr unknown
- 1976-05-06 CH CH568376A patent/CH622022A5/it not_active IP Right Cessation
- 1976-05-07 FR FR7613690A patent/FR2311018A1/fr active Granted
- 1976-05-11 AT AT343276A patent/AT343808B/de not_active IP Right Cessation
- 1976-05-11 DE DE2620782A patent/DE2620782C2/de not_active Expired
- 1976-05-13 DK DK215676A patent/DK215676A/da unknown
- 1976-05-13 NL NL7605142A patent/NL7605142A/xx active Search and Examination
- 1976-05-14 SU SU762356006A patent/SU598565A3/ru active
- 1976-05-14 HU HU76AI00000256A patent/HU171395B/hu unknown
- 1976-05-14 NO NO761681A patent/NO761681L/no unknown
- 1976-05-14 JP JP51055227A patent/JPS51141897A/ja active Granted
- 1976-05-14 ES ES448421A patent/ES448421A1/es not_active Expired
- 1976-05-14 PT PT65102A patent/PT65102B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES448421A1 (es) | 1977-07-01 |
| AT343808B (de) | 1978-06-26 |
| AU1357476A (en) | 1977-11-10 |
| HU171395B (hu) | 1978-01-28 |
| FR2311018B1 (fr) | 1979-05-25 |
| BE841548A (fr) | 1976-09-01 |
| FI761176A (fr) | 1976-11-16 |
| ATA343276A (de) | 1977-10-15 |
| FR2311018A1 (fr) | 1976-12-10 |
| SE7604755L (sv) | 1976-11-16 |
| JPS51141897A (en) | 1976-12-07 |
| IL49516A (en) | 1979-10-31 |
| GB1534075A (en) | 1978-11-29 |
| JPS623154B2 (fr) | 1987-01-23 |
| DK215676A (da) | 1976-11-16 |
| IT1048565B (it) | 1980-12-20 |
| PT65102B (en) | 1977-09-14 |
| SU598565A3 (ru) | 1978-03-15 |
| CA1057749A (fr) | 1979-07-03 |
| IL49516A0 (en) | 1976-07-30 |
| NL7605142A (nl) | 1976-11-17 |
| ZA762553B (en) | 1977-04-27 |
| US4017481A (en) | 1977-04-12 |
| IN143142B (fr) | 1977-10-08 |
| DE2620782A1 (de) | 1976-11-25 |
| PT65102A (en) | 1976-06-01 |
| IE42980L (en) | 1976-11-15 |
| IE42980B1 (en) | 1980-11-19 |
| NO761681L (fr) | 1976-11-16 |
| AR211013A1 (es) | 1977-10-14 |
| DE2620782C2 (de) | 1986-10-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: FARMITALIA CARLO ERBA S.P.A. |
|
| PFA | Name/firm changed |
Owner name: FARMITALIA CARLO ERBA S.R.L. |
|
| PL | Patent ceased |