CH629498A5 - Procedimento per la preparazione di composti di rifamicina. - Google Patents

Procedimento per la preparazione di composti di rifamicina. Download PDF

Info

Publication number: CH629498A5
Authority: CH; Switzerland
Prior art keywords: group; formula; atoms; phenyl; hours
Prior art date: 1976-09-30

Application number

CH953077A

Other languages

English (en)

Italian (it)

Inventor

Vittorio Rossetti

Leonardo Marsili

Carmine Pasqualucci

Original Assignee

Erba Farmitalia

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.)

1976-09-30

Filing date

1977-08-03

Publication date

1982-04-30

1977-08-03 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1982-04-30 Publication of CH629498A5 publication Critical patent/CH629498A5/it

Links

150000001875 compounds Chemical class 0.000 title claims description 9
238000000034 method Methods 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 72
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 50
229910052725 zinc Inorganic materials 0.000 claims description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 14
-1 methyl hydroxyl Chemical group 0.000 claims description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
229960001760 dimethyl sulfoxide Drugs 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 70
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
229910021529 ammonia Inorganic materials 0.000 description 35
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 33
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 30
238000003756 stirring Methods 0.000 description 28
239000011701 zinc Substances 0.000 description 26
239000000203 mixture Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
239000000047 product Substances 0.000 description 24
239000000243 solution Substances 0.000 description 24
229940076134 benzene Drugs 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
239000000741 silica gel Substances 0.000 description 16
229910002027 silica gel Inorganic materials 0.000 description 16
229960001866 silicon dioxide Drugs 0.000 description 16
235000010265 sodium sulphite Nutrition 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
239000000706 filtrate Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 9
239000007864 aqueous solution Substances 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
230000008020 evaporation Effects 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 2
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
RKXCKEHBMLDWET-UHFFFAOYSA-N 3,6-dihydro-2h-pyran-5-carbaldehyde Chemical compound O=CC1=CCCOC1 RKXCKEHBMLDWET-UHFFFAOYSA-N 0.000 description 1
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 1
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
241001530105 Anax Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
NVQOFWZLYDVFMU-UHFFFAOYSA-N azane;oxolane Chemical compound N.C1CCOC1 NVQOFWZLYDVFMU-UHFFFAOYSA-N 0.000 description 1
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical group C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
238000003795 desorption Methods 0.000 description 1
238000001663 electronic absorption spectrum Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000284 extract Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229940099259 vaseline Drugs 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
- 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

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)

CH953077A 1976-09-30 1977-08-03 Procedimento per la preparazione di composti di rifamicina. CH629498A5 (it)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT520976		1976-09-30

Publications (1)

Publication Number	Publication Date
CH629498A5 true CH629498A5 (it)	1982-04-30

Family

ID=11119379

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH953077A CH629498A5 (it)	1976-09-30	1977-08-03	Procedimento per la preparazione di composti di rifamicina.
CH952977A CH629497A5 (it)	1976-09-30	1977-08-03	Procedimento per la preparazione di composti di rifamicina.
CH952877A CH629496A5 (it)	1976-09-30	1977-08-03	Procedimento per la preparazione di composti di rifamicina.

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH952977A CH629497A5 (it)	1976-09-30	1977-08-03	Procedimento per la preparazione di composti di rifamicina.
CH952877A CH629496A5 (it)	1976-09-30	1977-08-03	Procedimento per la preparazione di composti di rifamicina.

Country Status (12)

Country	Link
US (3)	US4164499A (2)
JP (3)	JPS5350200A (2)
AT (2)	AT352279B (2)
CA (2)	CA1081218A (2)
CH (3)	CH629498A5 (2)
DE (3)	DE2739671A1 (2)
DK (2)	DK345977A (2)
ES (2)	ES462294A1 (2)
FR (3)	FR2366295A1 (2)
GB (3)	GB1560265A (2)
NL (2)	NL7710627A (2)
SE (2)	SE7708841L (2)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH633014A5 (en) *	1978-06-09	1982-11-15	Erba Farmitalia	Rifamycin compounds
BE886395A (fr) *	1980-02-13	1981-03-16	Erba Farmitalia	Derives de rifamycine
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
DD204925A5 (de) *	1980-09-25	1983-12-14	Ciba Geigy Ag	Verfahren zur herstellung eines 4-aminoimidazolo (4,5-c)rifamycins sv oder s
IT1201963B (it) *	1983-03-24	1989-02-02	Prodotti Antibiotici Spa	Derivati delle rifamicine e procedimento per la loro preparazione
US5362726A (en) *	1993-02-12	1994-11-08	Healthsearch, Inc.	Compound and method of treatment for falciparum malaria
AU2002360416A1 (en) *	2001-11-21	2003-06-10	Activbiotics, Inc.	Targeted therapeutics and uses thereof
PT102807A (pt) *	2002-07-09	2004-01-30	Inst Nac De Engenharia E Tecno	Derivados n-substituidos de rifabutina uteis como agentes antimicrobianos, processo para a sua preparacao e sua utilizacao como medicamentos
US7820652B2 (en) *	2003-09-24	2010-10-26	Activbiotics Pharma, Llc	Regimen for the administration of rifamycin-class antibiotics
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
WO2008008480A2 (en) *	2006-07-12	2008-01-17	Cumbre Pharmaceuticals Inc.	Nitroheteroaryl-containing rifamycin derivatives
WO2009064792A1 (en) *	2007-11-16	2009-05-22	Cumbre Pharmaceuticals Inc.	Quinolone carboxylic acid-substituted rifamycin derivatives

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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
CH536851A (de) *	1966-10-25	1973-05-15	Ciba Geigy Ag	Verfahren zur Herstellung neuer antibiotisch wirksamer Verbindungen der Rifamycinreihen
IT1048565B (it) *	1975-05-15	1980-12-20	Archifar Ind Chim Trentino	Amine aromatiche
IT1056271B (it) *	1975-05-20	1982-01-30	Archifar Ind Chim Trentino	Prodotti derivati dalle amine aromatiche
IT1056272B (it) *	1975-06-13	1982-01-30	Archifar Ind Chim Trentino	Prodotti derivati dalle amine aromatiche

1977
- 1977-08-02 DK DK345977A patent/DK345977A/da unknown
- 1977-08-03 CH CH953077A patent/CH629498A5/it not_active IP Right Cessation
- 1977-08-03 CH CH952977A patent/CH629497A5/it not_active IP Right Cessation
- 1977-08-03 SE SE7708841A patent/SE7708841L/xx unknown
- 1977-08-03 CH CH952877A patent/CH629496A5/it not_active IP Right Cessation
- 1977-08-09 GB GB33316/77A patent/GB1560265A/en not_active Expired
- 1977-08-09 SE SE7709001A patent/SE7709001L/xx not_active Application Discontinuation
- 1977-08-09 GB GB33315/77A patent/GB1550769A/en not_active Expired
- 1977-08-11 DK DK357477A patent/DK357477A/da unknown
- 1977-08-12 US US05/825,165 patent/US4164499A/en not_active Expired - Lifetime
- 1977-08-12 US US05/825,166 patent/US4165317A/en not_active Expired - Lifetime
- 1977-08-12 US US05/825,163 patent/US4175077A/en not_active Expired - Lifetime
- 1977-08-15 CA CA284,850A patent/CA1081218A/en not_active Expired
- 1977-08-15 GB GB34102/77A patent/GB1557090A/en not_active Expired
- 1977-08-16 CA CA284,958A patent/CA1083144A/en not_active Expired
- 1977-08-29 FR FR7726221A patent/FR2366295A1/fr active Granted
- 1977-08-29 FR FR7726222A patent/FR2366296A1/fr active Granted
- 1977-08-29 FR FR7726223A patent/FR2366294A1/fr active Granted
- 1977-09-02 DE DE19772739671 patent/DE2739671A1/de not_active Withdrawn
- 1977-09-02 DE DE19772739623 patent/DE2739623A1/de not_active Withdrawn
- 1977-09-02 DE DE19772739624 patent/DE2739624A1/de not_active Withdrawn
- 1977-09-09 AT AT649177A patent/AT352279B/de not_active IP Right Cessation
- 1977-09-09 AT AT649077A patent/AT352278B/de not_active IP Right Cessation
- 1977-09-12 ES ES462294A patent/ES462294A1/es not_active Expired
- 1977-09-12 ES ES462293A patent/ES462293A1/es not_active Expired
- 1977-09-21 JP JP11276477A patent/JPS5350200A/ja active Granted
- 1977-09-21 JP JP11276377A patent/JPS5350199A/ja active Granted
- 1977-09-21 JP JP11276277A patent/JPS5350198A/ja active Pending
- 1977-09-28 NL NL7710627A patent/NL7710627A/xx not_active Application Discontinuation
- 1977-09-28 NL NL7710625A patent/NL7710625A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
ES462293A1 (es)	1978-05-16
CH629496A5 (it)	1982-04-30
AT352278B (de)	1979-09-10
DE2739671A1 (de)	1978-04-06
CH629497A5 (it)	1982-04-30
US4164499A (en)	1979-08-14
AT352279B (de)	1979-09-10
JPS5526145B2 (2)	1980-07-11
NL7710627A (nl)	1978-04-03
FR2366296A1 (fr)	1978-04-28
JPS5350200A (en)	1978-05-08
FR2366294A1 (fr)	1978-04-28
CA1081218A (en)	1980-07-08
SE7708841L (sv)	1978-03-31
US4175077A (en)	1979-11-20
FR2366295A1 (fr)	1978-04-28
US4165317A (en)	1979-08-21
DE2739624A1 (de)	1978-04-06
GB1550769A (en)	1979-08-22
GB1560265A (en)	1980-02-06
DE2739623A1 (de)	1978-04-06
JPS5526146B2 (2)	1980-07-11
FR2366296B1 (2)	1982-11-19
JPS5350199A (en)	1978-05-08
SE7709001L (sv)	1978-03-31
FR2366294B1 (2)	1982-11-19
FR2366295B1 (2)	1982-11-19
GB1557090A (en)	1979-12-05
ATA649177A (de)	1979-02-15
JPS5350198A (en)	1978-05-08
ATA649077A (de)	1979-02-15
CA1083144A (en)	1980-08-05
NL7710625A (nl)	1978-04-03
ES462294A1 (es)	1978-05-16
DK357477A (da)	1978-03-31
DK345977A (da)	1978-03-31

Legal Events

Date	Code	Title	Description
1984-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH629498A5 (it)	1982-04-30	Procedimento per la preparazione di composti di rifamicina.
CA1092094A (en)	1980-12-23	Spirolactones and process for their preparation
KAMIYA et al.	1972	Bicyclomycin, a new antibiotic II. Structural elucidation and acyl derivatives
SU652896A3 (ru)	1979-03-15	Способ производства лейрокристина
SU1031407A3 (ru)	1983-07-23	Способ получени производных ( @ )-16-фенокси-9-кетопростатриеновой кислоты или их солей
SU1189353A3 (ru)	1985-10-30	Способ получени 3- кетоандростенов
US4007169A (en)	1977-02-08	Method of preparing derivatives of rifamycin S
Wiley et al.	1976	Sparsomycin, structure and chemistry
HU177591B (en)	1981-11-28	Process for producing 1-methyl-10-methoxy-lumilizergole derivatives
GB1602633A (en)	1981-11-11	Plant vinca rosea l process for the isolation of alkaloid components from the
Yanagisawa et al.	1976	Synthesis of 7α-substituted cephalosporins. V Novel oxidation procedure for syntheses of 7α-methoxycephalosporins and 6α-methoxypenicillins
AU595415B2 (en)	1990-03-29	Novel crystalline cefadroxil and method for producing it
US4410459A (en)	1983-10-18	Process for preparation of cytostatic compounds
SE457085B (sv)	1988-11-28	Oleandomycinderivat till anvaendning som mellanprodukt foer framstaellning av terapeutiskt anvaendbara derivat av 4"-desoxi-4"-amino-oleandomycin
CH625804A5 (2)	1981-10-15
CH629212A5 (it)	1982-04-15	Procedimento per la preparazione di composti di rifamicina.
SU423292A3 (ru)	1974-04-05	Способ получения пептидсодержащих эргоалкалоидов
PL124350B1 (en)	1983-01-31	Process for preparing vindesin
HU184516B (en)	1984-09-28	Process for producing 7-alpha-alkoxycarbonyl-15-beta,16-beta-methylene-4-androstene derivatives
US3738998A (en)	1973-06-12	Decarbamoylmitosanes
Williams et al.	1991	Hemiketal formation and subsequent intramolecular acylation of an N-hydroxy. beta.-lactam
US4251529A (en)	1981-02-17	Ergot peptide alkaloids
US4429129A (en)	1984-01-31	1α-Ethyl-1β-(2'-alkoxy carbonyl-2'-hydroxyiminoethyl)-10-methoxy 1,2,3,4,6,7,12,12β-octahydroindolo(2,3A)quinolizines
CA1123445A (en)	1982-05-11	Coriolin derivatives and process for producing the same
US3627781A (en)	1971-12-14	Decarbamoylmitosanes