HRP20110437A2 - Derivati rifamicina - Google Patents
Derivati rifamicina Download PDFInfo
- Publication number
- HRP20110437A2 HRP20110437A2 HR20110437A HRP20110437A HRP20110437A2 HR P20110437 A2 HRP20110437 A2 HR P20110437A2 HR 20110437 A HR20110437 A HR 20110437A HR P20110437 A HRP20110437 A HR P20110437A HR P20110437 A2 HRP20110437 A2 HR P20110437A2
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- Croatia
- Prior art keywords
- formula
- compound
- alkyl
- compounds
- hydrogen
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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 abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 238000000034 method Methods 0.000 claims abstract description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 238000002360 preparation method Methods 0.000 claims abstract description 34
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 9
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 64
- 238000011282 treatment Methods 0.000 claims description 47
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 33
- 230000001580 bacterial effect Effects 0.000 claims description 26
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical group OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=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 NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 claims description 15
- 229960003040 rifaximin Drugs 0.000 claims description 15
- 239000003242 anti bacterial agent Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 206010012735 Diarrhoea Diseases 0.000 claims description 12
- 239000007800 oxidant agent Substances 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 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 claims description 12
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 229930189077 Rifamycin Natural products 0.000 claims description 10
- 208000028774 intestinal disease Diseases 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 10
- 244000005700 microbiome Species 0.000 claims description 9
- 229960003292 rifamycin Drugs 0.000 claims description 9
- 208000011231 Crohn disease Diseases 0.000 claims description 8
- 239000002552 dosage form Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 6
- 229940088710 antibiotic agent Drugs 0.000 claims description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 6
- 229930193140 Neomycin Natural products 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
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- 229960004927 neomycin Drugs 0.000 claims description 5
- 235000010288 sodium nitrite Nutrition 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
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- 208000035467 Pancreatic insufficiency Diseases 0.000 claims description 4
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- 125000001931 aliphatic group Chemical group 0.000 claims description 4
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- 210000000813 small intestine Anatomy 0.000 claims description 4
- 150000003930 2-aminopyridines Chemical class 0.000 claims description 3
- ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
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- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
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- 230000000116 mitigating effect Effects 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 11
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000013543 active substance Substances 0.000 description 29
- -1 benzoyloxy, hydroxy Chemical group 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 13
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/20—Spiro-condensed systems
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/7036—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin having at least one amino group directly attached to the carbocyclic ring, e.g. streptomycin, gentamycin, amikacin, validamycin, fortimicins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
-
- 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
- C07D498/20—Spiro-condensed systems
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2009A000653A IT1397617B1 (it) | 2009-04-20 | 2009-04-20 | Nuovi derivati della rifamicina |
| PCT/IB2010/051183 WO2010122436A1 (en) | 2009-04-20 | 2010-03-18 | Rifamycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110437A2 true HRP20110437A2 (hr) | 2011-09-30 |
Family
ID=41228810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110437A HRP20110437A2 (hr) | 2009-04-20 | 2011-06-10 | Derivati rifamicina |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US8318763B2 (es) |
| EP (1) | EP2421869B1 (es) |
| JP (1) | JP5661100B2 (es) |
| KR (1) | KR101555860B1 (es) |
| CN (1) | CN102405223A (es) |
| AR (1) | AR076340A1 (es) |
| AU (1) | AU2010240638B2 (es) |
| BR (1) | BRPI1005979A8 (es) |
| CA (1) | CA2743801C (es) |
| CL (1) | CL2011002597A1 (es) |
| CO (1) | CO6362013A2 (es) |
| DK (1) | DK2421869T3 (es) |
| EA (1) | EA020201B1 (es) |
| ES (1) | ES2535327T3 (es) |
| HK (1) | HK1163663A1 (es) |
| HR (1) | HRP20110437A2 (es) |
| IL (1) | IL212942A (es) |
| IT (1) | IT1397617B1 (es) |
| MA (1) | MA33320B1 (es) |
| MX (1) | MX338334B (es) |
| NZ (1) | NZ595884A (es) |
| PL (1) | PL2421869T3 (es) |
| PT (1) | PT2421869E (es) |
| SG (1) | SG171989A1 (es) |
| TN (1) | TN2011000265A1 (es) |
| TW (1) | TWI422372B (es) |
| UA (1) | UA105775C2 (es) |
| WO (1) | WO2010122436A1 (es) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1698630B1 (en) | 2005-03-03 | 2014-09-03 | ALFA WASSERMANN S.p.A. | New polymorphous forms of rifaximin, processes for their production and use thereof in the medicinal preparations |
| ITBO20050123A1 (it) | 2005-03-07 | 2005-06-06 | Alfa Wassermann Spa | Formulazioni farmaceutiche gastroresistenti contenenti rifaximina |
| IT1398550B1 (it) | 2010-03-05 | 2013-03-01 | Alfa Wassermann Spa | Formulazioni comprendenti rifaximina utili per ottenere un effetto prolungato nel tempo |
| 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. |
| 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. |
| EP2895169A4 (en) * | 2012-09-12 | 2016-02-24 | Salix Pharmaceuticals Inc | METHODS OF ADMINISTERING RIFAXIMINE WITHOUT PRODUCING ANTIBIOTIC RESISTANCE |
| CN103709177B (zh) * | 2013-12-20 | 2016-02-24 | 武汉工程大学 | 利福霉素类沃尼妙林杂合抗生素及其制备方法 |
| SI3546464T1 (sl) * | 2014-05-12 | 2020-09-30 | Alfasigma S.P.A. | Priprava in uporaba rifaksimina v kristalni obliki TAU solvatiranega z degme |
| RU2020102511A (ru) * | 2017-06-26 | 2021-07-27 | Биофер С.П.А. | Соединения пиридо-имидазо рифамицина в качестве антибактериального средства |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2043847A1 (es) | 1969-05-30 | 1971-02-19 | Takeda Chemical Industries Ltd | |
| SU465795A3 (ru) * | 1972-05-05 | 1975-03-30 | Группо Лепетит (Фирма) | Способ получени рифамицина в. |
| US3847903A (en) * | 1973-03-01 | 1974-11-12 | Archifar Ind Chim Trentino | Method for extracting and isolating rifamycin o from fermentation broths of rifamycins |
| CH571064A5 (en) * | 1973-03-01 | 1975-12-31 | Archifar Ind Chim Trentino | Recovery of rieamycin from broths - by oxidn to an insol form |
| US4267274A (en) * | 1973-04-26 | 1981-05-12 | Gruppo Lepetit S.P.A. | Streptomyces mediterranei mutant capable of production of rifamycin B |
| GB1470426A (en) | 1974-08-30 | 1977-04-14 | Lepetit Spa | Rifamycins |
| 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 |
| IT1199374B (it) * | 1984-05-15 | 1988-12-30 | Alfa Farmaceutici Spa | Processo per la preparazione di pirido-imidazo-rifamicine |
| US7923553B2 (en) | 2003-11-07 | 2011-04-12 | Alfa Wassermann, S.P.A. | Processes for the production of polymorphic forms of rifaximin |
| ITMI20032144A1 (it) | 2003-11-07 | 2005-05-08 | Alfa Wassermann Spa | Forme polimorfe di rifaximina, processi per ottenerle e |
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