CH648037A5 - Imidazo-rifamycin-derivate mit antibakterieller wirksamkeit. - Google Patents
Imidazo-rifamycin-derivate mit antibakterieller wirksamkeit. Download PDFInfo
- Publication number
- CH648037A5 CH648037A5 CH3381/81A CH338181A CH648037A5 CH 648037 A5 CH648037 A5 CH 648037A5 CH 3381/81 A CH3381/81 A CH 3381/81A CH 338181 A CH338181 A CH 338181A CH 648037 A5 CH648037 A5 CH 648037A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- nothing
- rifamycin
- imidazo
- compound
- Prior art date
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- 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 9
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 74
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- 239000000126 substance Substances 0.000 claims description 18
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- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
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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 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
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- 229960003292 rifamycin Drugs 0.000 description 1
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT03429/80A IT1154655B (it) | 1980-05-22 | 1980-05-22 | Derivati imidazo-rifamicinici metodi per la loro preparazione e loro uso come sostanza ad azione antibatterica |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH648037A5 true CH648037A5 (de) | 1985-02-28 |
Family
ID=11107198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3381/81A CH648037A5 (de) | 1980-05-22 | 1981-05-22 | Imidazo-rifamycin-derivate mit antibakterieller wirksamkeit. |
Country Status (25)
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1199374B (it) | 1984-05-15 | 1988-12-30 | Alfa Farmaceutici Spa | Processo per la preparazione di pirido-imidazo-rifamicine |
| IT1264494B1 (it) * | 1993-03-23 | 1996-09-24 | Alfa Wassermann Spa | Uso di rifaximin e di formulazioni che la contengono nel trattamento delle dispepsie gastriche originate da helicobacter |
| US6861053B1 (en) * | 1999-08-11 | 2005-03-01 | Cedars-Sinai Medical Center | Methods of diagnosing or treating irritable bowel syndrome and other disorders caused by small intestinal bacterial overgrowth |
| US7048906B2 (en) | 1995-05-17 | 2006-05-23 | Cedars-Sinai Medical Center | Methods of diagnosing and treating small intestinal bacterial overgrowth (SIBO) and SIBO-related conditions |
| US5981522A (en) * | 1995-09-01 | 1999-11-09 | Kaneka Corporation | Treatment of disease caused by infection of Helicobacter |
| ES2237809T3 (es) * | 1997-02-28 | 2005-08-01 | Kaneka Corporation | Medicina curativa para la enfermedad causada por infeccion de helicobacter. |
| EP1453837A4 (en) * | 2001-11-21 | 2007-11-07 | Activbiotics Inc | TARGETED THERAPEUTIC AGENTS AND USES THEREOF |
| US7078399B2 (en) * | 2001-12-13 | 2006-07-18 | Activbiotics, Inc. | Sulfhydryl rifamycins and uses thereof |
| ES2385477T3 (es) * | 2002-11-05 | 2012-07-25 | Fadim S.R.L. | Liberación continua y controlada de rifaximina |
| US7820652B2 (en) * | 2003-09-24 | 2010-10-26 | Activbiotics Pharma, Llc | Regimen for the administration of rifamycin-class antibiotics |
| US20080262024A1 (en) * | 2003-11-07 | 2008-10-23 | Giuseppe Claudio Viscomi | Rifaximin compositions and method of use |
| US7902206B2 (en) * | 2003-11-07 | 2011-03-08 | Alfa Wassermann, S.P.A. | Polymorphic forms α, β and γ of rifaximin |
| US7923553B2 (en) * | 2003-11-07 | 2011-04-12 | Alfa Wassermann, S.P.A. | Processes for the production of polymorphic forms of rifaximin |
| US7906542B2 (en) * | 2004-11-04 | 2011-03-15 | Alfa Wassermann, S.P.A. | Pharmaceutical compositions comprising polymorphic forms α, β, and γ of rifaximin |
| ITMI20032144A1 (it) * | 2003-11-07 | 2005-05-08 | Alfa Wassermann Spa | Forme polimorfe di rifaximina, processi per ottenerle e |
| US7265107B2 (en) * | 2004-03-10 | 2007-09-04 | Cumbre Pharmaceuticals Inc. | Rifamycin C-11 oxime cyclo derivatives effective against drug-resistant microbes |
| US7256187B2 (en) * | 2004-03-10 | 2007-08-14 | Cumbre Pharmaceuticals Inc. | Rifamycin C-11 oxime derivatives effective against drug-resistant microbes |
| US7202246B2 (en) * | 2004-06-09 | 2007-04-10 | Cumbre Pharmaceuticals Inc. | Spiro-rifamycin derivatives targeting RNA polymerase |
| US20060210492A1 (en) * | 2005-03-02 | 2006-09-21 | Kodsi Robert E | Use of rifaximin for treatment and prevention of periodontal conditions |
| US8003118B2 (en) * | 2005-03-02 | 2011-08-23 | Kodsi Robert E | Use of rifaximin for the prevention of aspiration pneumonia and/or sepsis |
| US20060210483A1 (en) * | 2005-03-02 | 2006-09-21 | Kodsi Robert E | Non-systemic antibiotic formulations and related method of use and treatment of upper respiratory infections |
| ES2522895T3 (es) | 2005-03-03 | 2014-11-19 | Alfa Wassermann S.P.A. | Nuevas formas polimorfas de rifaximina, procedimientos para su producción y uso de las mismas en preparados medicinales |
| ITBO20050123A1 (it) * | 2005-03-07 | 2005-06-06 | Alfa Wassermann Spa | Formulazioni farmaceutiche gastroresistenti contenenti rifaximina |
| KR101327635B1 (ko) | 2005-08-11 | 2013-11-12 | 타간타 테라퓨틱스 인크. | 포스폰산화 리파마이신, 및 그의 뼈 및 관절 감염의 저지및 치료 용도 |
| WO2007103448A2 (en) | 2006-03-09 | 2007-09-13 | Salix Pharmaceuticals, Inc. | Rifaximin anti-rectal dysfunction preparation |
| DK2054066T3 (en) | 2006-08-02 | 2015-06-08 | Salix Pharmaceuticals Inc | METHODS OF TREATMENT OF RADIATE ENTERITIS |
| ITMI20061692A1 (it) | 2006-09-05 | 2008-03-06 | Alfa Wassermann Spa | Uso di polioli per ottenere forme polimorfe stabili di rifaximina |
| KR101667534B1 (ko) * | 2006-09-22 | 2016-10-19 | 씨아이피엘에이 엘티디. | 리팍시민 |
| US20080161337A1 (en) * | 2007-01-03 | 2008-07-03 | Leonard Weinstock | Use of Rifaximin for the Treatment of Chronic Prostatitis |
| US20080159987A1 (en) * | 2007-01-03 | 2008-07-03 | Leonard Weinstock | Use of Rifaximin for the Treatment of Restless Legs Syndrome |
| ITMI20071241A1 (it) * | 2007-06-20 | 2008-12-21 | Solmag S P A | Processo per la preparazione di rifaximina amorfa e rifaximina amorfa cosi' ottenuta |
| ES2798253T3 (es) | 2007-07-06 | 2020-12-10 | Lupin Ltd | Composiciones farmacéuticas de rifaximina |
| AU2008273699A1 (en) | 2007-07-06 | 2009-01-15 | Lupin Limited | Pharmaceutical compositions of rifaximin |
| US7709634B2 (en) * | 2007-09-20 | 2010-05-04 | Apotex Pharmachem Inc. | Amorphous form of rifaximin and processes for its preparation |
| BRPI0908864A2 (pt) | 2008-02-25 | 2018-09-18 | Salix Pharmaceuticals Ltd | formas da rifaximina e usos das mesmas |
| US8486956B2 (en) | 2008-02-25 | 2013-07-16 | Salix Pharmaceuticals, Ltd | Forms of rifaximin and uses thereof |
| US8309569B2 (en) | 2008-02-26 | 2012-11-13 | Salix Pharmaceuticals, Ltd. | Methods for treating diarrhea-associated irritable bowel syndrome |
| US11779571B2 (en) | 2008-02-26 | 2023-10-10 | Salix Pharmaceuticals, Inc. | Methods for treating irritable bowel syndrome (IBS) |
| EP2294012B1 (en) | 2008-05-07 | 2014-07-09 | Salix Pharmaceuticals, Ltd. | Administration of a bowel cleanser and an antibiotic for the treatment of bowel disease |
| US8524691B2 (en) | 2008-08-13 | 2013-09-03 | The Medicines Company | Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections |
| RU2011116400A (ru) | 2008-09-26 | 2012-11-10 | Аска Фармасьютикал Ко., Лтд. (Jp) | Средство для предотвращения и/или лечения функционального расстройства желудочно-кишечного тракта |
| US12285414B2 (en) | 2008-10-02 | 2025-04-29 | Salix Pharmaceuticals, Inc. | Methods of treating hepatic encephalopathy |
| EP3628319B1 (en) | 2008-10-02 | 2024-02-14 | Salix Pharmaceuticals, Ltd. | Treatment of hepatic encephalopathy using rifaximin |
| WO2010067072A1 (en) | 2008-12-10 | 2010-06-17 | Cipla Limited | Rifaximin complexes |
| IT1397617B1 (it) * | 2009-04-20 | 2013-01-18 | Alfa Wassermann Spa | Nuovi derivati della rifamicina |
| CN102548408A (zh) | 2009-06-02 | 2012-07-04 | 萨利克斯药品有限公司 | 治疗肝性脑病的方法 |
| KR20120062897A (ko) | 2009-09-13 | 2012-06-14 | 샐릭스 파마슈티컬스 리미티드 | 과민성 장 증후군(ｉｂｓ)의 치료방법 |
| CN113274355B (zh) | 2009-10-27 | 2023-05-30 | 鲁平有限公司 | 利福昔明固体分散体 |
| WO2011061519A2 (en) | 2009-11-23 | 2011-05-26 | Cipla Limited | Topical foam composition |
| EP2401282B2 (en) | 2009-12-28 | 2017-01-04 | Silvio Massimo Lavagna | Method for the production of amorphous rifaximin |
| AU2011218129A1 (en) | 2010-02-18 | 2012-08-23 | Board Of Regents Of The University Of Texas System | Methods for treating infection |
| IT1398550B1 (it) | 2010-03-05 | 2013-03-01 | Alfa Wassermann Spa | Formulazioni comprendenti rifaximina utili per ottenere un effetto prolungato nel tempo |
| CA2800235C (en) | 2010-03-10 | 2018-10-16 | Lupin Limited | Rifaximin ready-to-use suspension |
| US20120077835A1 (en) | 2010-07-12 | 2012-03-29 | Salix Pharmaceuticals, Ltd. | Formulations of rifaximin and uses thereof |
| WO2012035544A2 (en) | 2010-09-13 | 2012-03-22 | Sequent Scientific Ltd. | A novel polymorphic form of rifaximin and process for its preparation |
| JP6076267B2 (ja) | 2011-02-11 | 2017-02-08 | サリックス ファーマスーティカルズ，リミテッド | リファキシミンの形態およびその使用 |
| EP2705042A1 (en) | 2011-05-02 | 2014-03-12 | Ranbaxy Laboratories Limited | Rifaximin dimethylformamide solvate |
| ITMI20110890A1 (it) * | 2011-05-19 | 2012-11-20 | A M S A Anonima Materie Sint & Affini S P A | Polimorfo di rifaximina e processo per la sua preparazione |
| ITBO20110461A1 (it) | 2011-07-29 | 2013-01-30 | Alfa Wassermann Spa | Composizioni farmaceutiche comprendenti rifaximina, processi per la loro preparazione e loro uso nel trattamento di infezioni vaginali. |
| RU2496475C2 (ru) | 2011-10-26 | 2013-10-27 | Александр Васильевич Иващенко | Фармацевтическая композиция и набор для лечения бактериальных инфекций |
| PL2773205T3 (pl) | 2011-11-02 | 2024-09-02 | Salix Pharmaceuticals, Inc. | Ryfaksymina w leczeniu ustępującej biegunki z przewagą zespołu jelita drażliwego |
| EP2807148A4 (en) * | 2012-01-25 | 2015-04-08 | Salix Pharmaceuticals Ltd | RIFAXIMIN DERIVATIVE AND USES THEREOF |
| ITBO20120368A1 (it) | 2012-07-06 | 2014-01-07 | Alfa Wassermann Spa | Composizioni comprendenti rifaximina e amminoacidi, cristalli di rifaximina derivanti da tali composizioni e loro uso. |
| WO2014091432A1 (en) | 2012-12-12 | 2014-06-19 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of rifaximin |
| CA2897758A1 (en) | 2013-03-15 | 2014-09-18 | Alfa Wassermann S.P.A. | Rifaximin for use in the treating of vaginal infections |
| WO2014140995A2 (en) | 2013-03-15 | 2014-09-18 | Alfa Wassermann S.P.A. | Method for diagnosing vaginal infections |
| MX374340B (es) | 2013-04-12 | 2025-03-06 | Alfasigma Spa | Administracion de farmacos antiinflamatorios no esteroidales y composiciones, metodos y sistemas relacionados. |
| US9018225B1 (en) | 2013-07-26 | 2015-04-28 | Novel Laboratories | Rifaximin crystalline forms and methods of preparation thereof |
| EP2927235B1 (en) | 2014-03-31 | 2017-02-08 | Euticals S.P.A. | Polymorphic mixture of rifaximin and its use for the preparation of solid formulations |
| WO2015159275A2 (en) * | 2014-04-19 | 2015-10-22 | Granules India Limited | An improved process for the preparation of rifamycin derivatives |
| EP3140313B1 (en) | 2014-05-04 | 2020-02-26 | Salix Pharmaceuticals, Inc. | Ibs microbiota and uses thereof |
| EP3546464B1 (en) | 2014-05-12 | 2020-06-17 | Alfasigma S.p.A. | Preparation and use of crystalline form tau of rifaximin solvated with degme |
| EP2982764A1 (en) | 2014-08-05 | 2016-02-10 | ALFA WASSERMANN S.p.A. | Identification of vaginal bacteria |
| US9988398B2 (en) | 2016-06-07 | 2018-06-05 | Cadila Healthcare Limited | Crystalline form of rifaximin and process for its preparation |
| KR102494049B1 (ko) | 2016-09-30 | 2023-01-31 | 샐릭스 파마슈티컬스 인코포레이티드 | 리팍시민의 고체 분산물 형태 |
| IT201700091912A1 (it) * | 2017-08-08 | 2019-02-08 | Biofer Spa | Nuove pirido-imidazo rifamicine |
| DK3645539T3 (da) * | 2017-06-26 | 2021-05-10 | Biofer Spa | Pyrido-imidazo-rifamycin-derivater som antibakterielt middel |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE273377C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| AT273377B (de) * | 1967-03-01 | 1969-08-11 | Lepetit Spa | Verfahren zur Herstellung von neuen Rifamycinen |
| AT344898B (de) * | 1975-06-13 | 1978-08-10 | Archifar Ind Chim Trentino | Verfahren zur herstellung neuer rifamycin-verbindungen |
| 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. |
| CH633014A5 (en) * | 1978-06-09 | 1982-11-15 | Erba Farmitalia | Rifamycin compounds |
-
1980
- 1980-05-22 IT IT03429/80A patent/IT1154655B/it active Protection Beyond IP Right Term
-
1981
- 1981-05-11 NL NLAANVRAGE8102290,A patent/NL187022C/xx not_active IP Right Cessation
- 1981-05-11 US US06/262,123 patent/US4341785A/en not_active Expired - Lifetime
- 1981-05-18 AU AU70655/81A patent/AU537093B2/en not_active Expired
- 1981-05-19 AT AT0222781A patent/AT373599B/de not_active IP Right Cessation
- 1981-05-20 FR FR8110058A patent/FR2482967A1/fr active Granted
- 1981-05-20 PH PH25656A patent/PH17207A/en unknown
- 1981-05-20 PT PT73064A patent/PT73064B/pt unknown
- 1981-05-20 EG EG280/81A patent/EG14891A/xx active
- 1981-05-20 LU LU83376A patent/LU83376A1/fr unknown
- 1981-05-20 GR GR65010A patent/GR75640B/el unknown
- 1981-05-21 CA CA000378015A patent/CA1142518A/en not_active Expired
- 1981-05-21 IE IE1139/81A patent/IE51204B1/en not_active IP Right Cessation
- 1981-05-21 ES ES502906A patent/ES502906A0/es active Granted
- 1981-05-21 BE BE2/59169A patent/BE888895A/fr not_active IP Right Cessation
- 1981-05-21 SE SE8103216A patent/SE453089B/sv not_active IP Right Cessation
- 1981-05-21 DK DK224781A patent/DK157876C/da active
- 1981-05-21 ZA ZA00813430A patent/ZA813430B/xx unknown
- 1981-05-21 FI FI811565A patent/FI69467C/fi not_active IP Right Cessation
- 1981-05-21 NO NO811731A patent/NO155622C/no unknown
- 1981-05-22 GB GB8115790A patent/GB2079270B/en not_active Expired
- 1981-05-22 JP JP7787781A patent/JPS5711987A/ja active Granted
- 1981-05-22 AR AR285424A patent/AR226212A1/es active
- 1981-05-22 CH CH3381/81A patent/CH648037A5/de not_active IP Right Cessation
- 1981-05-22 DE DE19813120460 patent/DE3120460A1/de active Granted
-
1982
- 1982-02-09 PH PH26842A patent/PH18704A/en unknown
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