IE58392B1 - A new process for the synthesis of pyrido-imidazo-rifamycins - Google Patents

A new process for the synthesis of pyrido-imidazo-rifamycins

Info

Publication number: IE58392B1
Authority: IE; Ireland
Prior art keywords: alkyl; formula; rifamycin; pyrido; imidazo
Prior art date: 1984-05-15

Application number

IE119185A

Other languages

English (en)

Other versions

IE851191L (en

Original Assignee

Alfa Wassermann Spa

Priority date (The priority date 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 date listed.)

1984-05-15

Filing date

1985-05-14

Publication date

1993-09-08

1985-05-14 Application filed by Alfa Wassermann Spa filed Critical Alfa Wassermann Spa

1985-11-15 Publication of IE851191L publication Critical patent/IE851191L/xx

1993-09-08 Publication of IE58392B1 publication Critical patent/IE58392B1/en

Links

238000000034 method Methods 0.000 title claims abstract description 24
230000008569 process Effects 0.000 title claims abstract description 17
229940081192 rifamycins Drugs 0.000 title claims abstract description 7
230000015572 biosynthetic process Effects 0.000 title abstract 2
238000003786 synthesis reaction Methods 0.000 title abstract 2
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 abstract description 30
229930189077 Rifamycin Natural products 0.000 claims abstract description 21
-1 hydroxy-(C2-4)-alkyl Chemical group 0.000 claims abstract description 18
229960003292 rifamycin Drugs 0.000 claims abstract description 17
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims abstract description 12
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
239000002904 solvent Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
239000011630 iodine Substances 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 8
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
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 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
150000002334 glycols Chemical class 0.000 claims description 3
150000008282 halocarbons Chemical class 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims 2
150000003222 pyridines Chemical class 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
150000001875 compounds Chemical class 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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 13
229940109171 rifamycin sv Drugs 0.000 description 13
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000001228 spectrum Methods 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
239000000047 product Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
ORLGLBZRQYOWNA-UHFFFAOYSA-N 4-methylpyridin-2-amine Chemical compound CC1=CC=NC(N)=C1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 5
RAFHKEAPVIWLJC-OQQFTUDCSA-N Rifamycin O Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC5(OCC(=O)O5)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C RAFHKEAPVIWLJC-OQQFTUDCSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
235000010323 ascorbic acid Nutrition 0.000 description 5
229960005070 ascorbic acid Drugs 0.000 description 5
239000011668 ascorbic acid Substances 0.000 description 5
RAFHKEAPVIWLJC-TWYIRNIGSA-N z67lem9p1w 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)N2)C)OC)C(C(=C3O)C)=C1C1=C3C(=O)C2=C[C@]11OCC(=O)O1 RAFHKEAPVIWLJC-TWYIRNIGSA-N 0.000 description 5
241000786363 Rhampholeon spectrum Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241001342522 Vampyrum spectrum Species 0.000 description 3
229950011175 aminopicoline Drugs 0.000 description 3
150000003927 aminopyridines Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013065 commercial product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-DUZGATOHSA-N D-isoascorbic acid Chemical compound OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
241000187654 Nocardia Species 0.000 description 1
BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 description 1
BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=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 BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
210000001557 animal structure Anatomy 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229940120503 dihydroxyacetone Drugs 0.000 description 1
238000007865 diluting Methods 0.000 description 1
235000010350 erythorbic acid Nutrition 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
229940006461 iodide ion Drugs 0.000 description 1
229940026239 isoascorbic acid Drugs 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
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
SQTCRTQCPJICLD-KTQDUKAHSA-N rifamycin B Chemical compound OC1=C(C(O)=C2C)C3=C(OCC(O)=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 SQTCRTQCPJICLD-KTQDUKAHSA-N 0.000 description 1
SQTCRTQCPJICLD-OQQFTUDCSA-N rifomycin-B 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(OCC(=O)O)c4c3C2=O SQTCRTQCPJICLD-OQQFTUDCSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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

Landscapes

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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IE119185A 1984-05-15 1985-05-14 A new process for the synthesis of pyrido-imidazo-rifamycins IE58392B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT03463/84A IT1199374B (it)	1984-05-15	1984-05-15	Processo per la preparazione di pirido-imidazo-rifamicine

Publications (2)

Publication Number	Publication Date
IE851191L IE851191L (en)	1985-11-15
IE58392B1 true IE58392B1 (en)	1993-09-08

Family

ID=11107845

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE119185A IE58392B1 (en)	1984-05-15	1985-05-14	A new process for the synthesis of pyrido-imidazo-rifamycins

Country Status (18)

Country	Link
US (1)	US4557866A (2)
EP (1)	EP0161534B1 (2)
JP (1)	JPS60252483A (2)
AR (1)	AR241913A1 (2)
AT (1)	ATE46512T1 (2)
AU (1)	AU568934B2 (2)
CA (1)	CA1215708A (2)
DE (1)	DE3573120D1 (2)
DK (1)	DK162647C (2)
ES (1)	ES8603489A1 (2)
FI (1)	FI81101C (2)
GR (1)	GR851144B (2)
IE (1)	IE58392B1 (2)
IT (1)	IT1199374B (2)
NO (1)	NO164242C (2)
PH (1)	PH22007A (2)
PT (1)	PT80446B (2)
ZA (1)	ZA852971B (2)

Families Citing this family (62)

* Cited by examiner, † Cited by third party
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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
WO2003051299A2 (en) *	2001-12-13	2003-06-26	Activbiotics, Inc.	Sulfhydryl rifamycins and uses thereof
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
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
ITMI20032144A1 (it) *	2003-11-07	2005-05-08	Alfa Wassermann Spa	Forme polimorfe di rifaximina, processi per ottenerle e
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
US8003118B2 (en) *	2005-03-02	2011-08-23	Kodsi Robert E	Use of rifaximin for the prevention of aspiration pneumonia and/or sepsis
US20060210492A1 (en) *	2005-03-02	2006-09-21	Kodsi Robert E	Use of rifaximin for treatment and prevention of periodontal conditions
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
KR101398648B1 (ko)	2006-03-09	2014-06-27	샐릭스 파마슈티컬스 인코포레이티드	리팍시민 직장 기능장애 치료 제제
WO2008016708A2 (en)	2006-08-02	2008-02-07	Salix Pharmaceuticals, Inc.	Methods for treatment of radiation enteritis
ITMI20061692A1 (it)	2006-09-05	2008-03-06	Alfa Wassermann Spa	Uso di polioli per ottenere forme polimorfe stabili di rifaximina
AU2007298733B2 (en) *	2006-09-22	2012-11-08	Cipla Limited	Rifaximin
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
US7709634B2 (en)	2007-09-20	2010-05-04	Apotex Pharmachem Inc.	Amorphous form of rifaximin and processes for its preparation
EP2257557A4 (en)	2008-02-25	2011-06-29	Salix Pharmaceuticals Ltd	FORMS OF RIFAXIMINE AND APPLICATIONS THEREOF
US8486956B2 (en) *	2008-02-25	2013-07-16	Salix Pharmaceuticals, Ltd	Forms of rifaximin and uses thereof
US11779571B2 (en)	2008-02-26	2023-10-10	Salix Pharmaceuticals, Inc.	Methods for treating irritable bowel syndrome (IBS)
ES2727728T3 (es)	2008-02-26	2019-10-18	Salix Pharmaceuticals Ltd	Métodos para el tratamiento del síndrome del intestino irritable
WO2009137672A1 (en)	2008-05-07	2009-11-12	Salix Pharmaceuticals, Ltd.	Methods of treating bowel disease by administering a bowel cleanser and an antibiotic
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1984
- 1984-05-15 IT IT03463/84A patent/IT1199374B/it active
1985
- 1985-04-19 AT AT85104790T patent/ATE46512T1/de not_active IP Right Cessation
- 1985-04-19 ZA ZA852971A patent/ZA852971B/xx unknown
- 1985-04-19 EP EP85104790A patent/EP0161534B1/en not_active Expired
- 1985-04-19 DE DE8585104790T patent/DE3573120D1/de not_active Expired
- 1985-04-25 PH PH32186A patent/PH22007A/en unknown
- 1985-04-26 US US06/727,521 patent/US4557866A/en not_active Expired - Lifetime
- 1985-04-29 CA CA000480321A patent/CA1215708A/en not_active Expired
- 1985-05-13 GR GR851144A patent/GR851144B/el unknown
- 1985-05-13 PT PT80446A patent/PT80446B/pt unknown
- 1985-05-14 IE IE119185A patent/IE58392B1/en not_active IP Right Cessation
- 1985-05-14 JP JP60102528A patent/JPS60252483A/ja active Granted
- 1985-05-14 ES ES543115A patent/ES8603489A1/es not_active Expired
- 1985-05-14 DK DK214685A patent/DK162647C/da not_active IP Right Cessation
- 1985-05-14 NO NO851921A patent/NO164242C/no not_active IP Right Cessation
- 1985-05-14 FI FI851907A patent/FI81101C/fi not_active IP Right Cessation
- 1985-05-15 AR AR85300385A patent/AR241913A1/es active
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Also Published As

Publication number	Publication date
JPH0469634B2 (2)	1992-11-06
IE851191L (en)	1985-11-15
DK162647C (da)	1992-04-13
AU4251585A (en)	1985-11-21
NO851921L (no)	1985-11-18
FI851907A0 (fi)	1985-05-14
ZA852971B (en)	1985-12-24
EP0161534A2 (en)	1985-11-21
FI851907L (fi)	1985-11-16
CA1215708A (en)	1986-12-23
PT80446A (en)	1985-06-01
JPS60252483A (ja)	1985-12-13
FI81101C (fi)	1990-09-10
DK214685D0 (da)	1985-05-14
IT1199374B (it)	1988-12-30
ES543115A0 (es)	1986-01-01
DE3573120D1 (en)	1989-10-26
ATE46512T1 (de)	1989-10-15
PH22007A (en)	1988-05-02
AR241913A1 (es)	1993-01-29
NO164242B (no)	1990-06-05
US4557866A (en)	1985-12-10
DK162647B (da)	1991-11-25
GR851144B (2)	1985-11-25
NO164242C (no)	1990-09-12
EP0161534A3 (en)	1987-03-04
PT80446B (pt)	1987-11-11
FI81101B (fi)	1990-05-31
ES8603489A1 (es)	1986-01-01
AU568934B2 (en)	1988-01-14
IT8403463A0 (it)	1984-05-15
EP0161534B1 (en)	1989-09-20
DK214685A (da)	1985-11-16

Legal Events

Date	Code	Title	Description
2005-06-29	MK9A	Patent expired

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US4659812A (en)	1987-04-21	Cephalosporin intermediates
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Mooney et al.	1982	Some Reactions of α-Trifluoromethylsulphonyloxy-Penicillanate Esters
JPS626556B2 (2)	1987-02-12
GB2106908A (en)	1983-04-20	Alkoxyvincamone derivatives
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HU192276B (en)	1987-05-28	Process for preparing 4-deacetyl-3',4'-anhydro- vincristine
EP0310969A2 (en)	1989-04-12	Pyrido-benzothiazine derivatives having high antibacterial activity and high bioavailability to tissues