GB1603127A - Rifamycin compounds - Google Patents
Rifamycin compounds Download PDFInfo
- Publication number
- GB1603127A GB1603127A GB22170/78A GB2217078A GB1603127A GB 1603127 A GB1603127 A GB 1603127A GB 22170/78 A GB22170/78 A GB 22170/78A GB 2217078 A GB2217078 A GB 2217078A GB 1603127 A GB1603127 A GB 1603127A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- alkyl
- rifamycin
- carbon atoms
- formula
- 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.)
- Expired
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 abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- -1 rifamycin compound Chemical class 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 21
- 239000000243 solution Substances 0.000 claims description 21
- 229910052725 zinc Inorganic materials 0.000 claims description 21
- 239000011701 zinc Substances 0.000 claims description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 17
- 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 claims description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 14
- 239000005695 Ammonium acetate Substances 0.000 claims description 14
- 229940043376 ammonium acetate Drugs 0.000 claims description 14
- 235000019257 ammonium acetate Nutrition 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000001663 electronic absorption spectrum Methods 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 229930189077 Rifamycin Natural products 0.000 claims description 10
- 229960003292 rifamycin Drugs 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000012074 organic phase Substances 0.000 claims description 8
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 5
- 235000011152 sodium sulphate Nutrition 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000012064 sodium phosphate buffer Substances 0.000 claims description 4
- 238000004809 thin layer chromatography Methods 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- QFWBXLYVHOMANN-UHFFFAOYSA-N 1-(3-methoxypropyl)piperidin-4-one Chemical compound COCCCN1CCC(=O)CC1 QFWBXLYVHOMANN-UHFFFAOYSA-N 0.000 claims description 2
- UEWKKUAXRZRSQT-UHFFFAOYSA-N 1-(5-methylhexan-2-yl)piperidin-4-one Chemical compound CC(C)CCC(C)N1CCC(=O)CC1 UEWKKUAXRZRSQT-UHFFFAOYSA-N 0.000 claims description 2
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
- QEZGRWSAUJTDEZ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperidine-1-carbonyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)C(=O)N1CCCCC1 QEZGRWSAUJTDEZ-UHFFFAOYSA-N 0.000 claims description 2
- DCVGCQPXTOSWEA-UHFFFAOYSA-N 4-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]pyrazol-3-yl]methyl]-1-methylpiperazin-2-one Chemical compound CN1CCN(CC2=NN(CC(=O)N3CCC4=C(C3)N=NN4)C=C2C2=CN=C(NC3CC4=C(C3)C=CC=C4)N=C2)CC1=O DCVGCQPXTOSWEA-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 2
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 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 2
- MEESULSAEVCKJK-UHFFFAOYSA-N 1-(2-methyloxolan-3-yl)piperidin-4-one Chemical compound CC1OCCC1N1CCC(=O)CC1 MEESULSAEVCKJK-UHFFFAOYSA-N 0.000 description 1
- BDVKAMAALQXGLM-UHFFFAOYSA-N 1-ethylpiperidin-4-one Chemical compound CCN1CCC(=O)CC1 BDVKAMAALQXGLM-UHFFFAOYSA-N 0.000 description 1
- NUPCXPOFGHXLIZ-UHFFFAOYSA-N 1-hexylpiperidin-4-one Chemical compound CCCCCCN1CCC(=O)CC1 NUPCXPOFGHXLIZ-UHFFFAOYSA-N 0.000 description 1
- MSUAFFBEKJQZIC-UHFFFAOYSA-N 2-chloroethanone Chemical group ClC[C]=O MSUAFFBEKJQZIC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 241001646725 Mycobacterium tuberculosis H37Rv Species 0.000 description 1
- 108700035964 Mycobacterium tuberculosis HsaD Proteins 0.000 description 1
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000011282 treatment 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
- C07D498/22—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
-
- 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SG38683A SG38683G (en) | 1978-05-24 | 1983-07-02 | Rifamycin compounds |
| HK56183A HK56183A (en) | 1978-05-24 | 1983-11-17 | Rifamycin compounds |
| CS914196A CS419691A3 (en) | 1978-05-24 | 1991-12-31 | Rifamycin compounds |
| BG098016A BG60435B2 (bg) | 1978-05-24 | 1993-08-03 | Съединения на рифамицина |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2825445A DE2825445C2 (de) | 1975-06-13 | 1978-06-09 | Rifamycin-S-Verbindungen und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1603127A true GB1603127A (en) | 1981-11-18 |
Family
ID=6041475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB22170/78A Expired GB1603127A (en) | 1978-05-24 | 1978-05-24 | Rifamycin compounds |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS557203A (enrdf_load_stackoverflow) |
| BE (1) | BE870570R (enrdf_load_stackoverflow) |
| CA (1) | CA1089453A (enrdf_load_stackoverflow) |
| CH (1) | CH633014A5 (enrdf_load_stackoverflow) |
| FR (1) | FR2426690A2 (enrdf_load_stackoverflow) |
| GB (1) | GB1603127A (enrdf_load_stackoverflow) |
| NL (2) | NL182564C (enrdf_load_stackoverflow) |
| SE (1) | SE441751B (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008008480A3 (en) * | 2006-07-12 | 2008-03-13 | Cumbre Pharmaceuticals Inc | Nitroheteroaryl-containing rifamycin derivatives |
| WO2009064792A1 (en) * | 2007-11-16 | 2009-05-22 | Cumbre Pharmaceuticals Inc. | Quinolone carboxylic acid-substituted rifamycin derivatives |
| WO2013062445A1 (ru) | 2011-10-26 | 2013-05-02 | ИВАЩЕНКО, Андрей Александрович | Фармацевтическая композиция и набор для лечения бактериальных инфекций |
| CN103408571A (zh) * | 2013-08-23 | 2013-11-27 | 成都樵枫科技发展有限公司 | 利福布丁的晶型i及其制备方法和用途 |
| CN106279205A (zh) * | 2015-05-12 | 2017-01-04 | 重庆华邦胜凯制药有限公司 | 制备利福霉素s衍生物的方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1154655B (it) * | 1980-05-22 | 1987-01-21 | Alfa Farmaceutici Spa | Derivati imidazo-rifamicinici metodi per la loro preparazione e loro uso come sostanza ad azione antibatterica |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1056271B (it) * | 1975-05-20 | 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 |
-
1978
- 1978-05-22 CH CH554478A patent/CH633014A5/it not_active IP Right Cessation
- 1978-05-23 SE SE7805863A patent/SE441751B/sv not_active IP Right Cessation
- 1978-05-24 GB GB22170/78A patent/GB1603127A/en not_active Expired
- 1978-05-24 FR FR7815450A patent/FR2426690A2/fr active Granted
- 1978-05-30 CA CA304,380A patent/CA1089453A/en not_active Expired
- 1978-06-20 NL NLAANVRAGE7806659,A patent/NL182564C/xx not_active IP Right Cessation
- 1978-06-27 JP JP7706378A patent/JPS557203A/ja active Granted
- 1978-09-18 BE BE190561A patent/BE870570R/xx active
-
1995
- 1995-11-22 NL NL950028C patent/NL950028I2/nl unknown
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008008480A3 (en) * | 2006-07-12 | 2008-03-13 | Cumbre Pharmaceuticals Inc | Nitroheteroaryl-containing rifamycin derivatives |
| US7678791B2 (en) | 2006-07-12 | 2010-03-16 | Cumbre Ip Ventures, L.P. | Nitroheteroaryl-containing rifamycin derivatives |
| WO2009064792A1 (en) * | 2007-11-16 | 2009-05-22 | Cumbre Pharmaceuticals Inc. | Quinolone carboxylic acid-substituted rifamycin derivatives |
| US7884099B2 (en) | 2007-11-16 | 2011-02-08 | Cumbre Ip Ventures, L.P. | Quinolone carboxylic acid-substituted rifamycin derivatives |
| WO2013062445A1 (ru) | 2011-10-26 | 2013-05-02 | ИВАЩЕНКО, Андрей Александрович | Фармацевтическая композиция и набор для лечения бактериальных инфекций |
| CN103408571A (zh) * | 2013-08-23 | 2013-11-27 | 成都樵枫科技发展有限公司 | 利福布丁的晶型i及其制备方法和用途 |
| CN103408571B (zh) * | 2013-08-23 | 2015-11-18 | 成都樵枫科技发展有限公司 | 利福布丁的晶型i及其制备方法和用途 |
| CN106279205A (zh) * | 2015-05-12 | 2017-01-04 | 重庆华邦胜凯制药有限公司 | 制备利福霉素s衍生物的方法 |
| CN106279205B (zh) * | 2015-05-12 | 2020-07-21 | 重庆华邦胜凯制药有限公司 | 制备利福霉素s衍生物的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1089453A (en) | 1980-11-11 |
| BE870570R (fr) | 1979-01-15 |
| NL182564C (nl) | 1988-04-05 |
| JPH0114238B2 (enrdf_load_stackoverflow) | 1989-03-10 |
| NL182564B (nl) | 1987-11-02 |
| SE7805863L (sv) | 1979-11-24 |
| NL950028I1 (nl) | 1996-03-01 |
| NL950028I2 (nl) | 1997-04-01 |
| JPS557203A (en) | 1980-01-19 |
| SE441751B (sv) | 1985-11-04 |
| FR2426690B2 (enrdf_load_stackoverflow) | 1982-05-28 |
| CH633014A5 (en) | 1982-11-15 |
| NL7806659A (nl) | 1979-12-27 |
| FR2426690A2 (fr) | 1979-12-21 |
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