CA1173030A - Rifamycin derivatives - Google Patents
Rifamycin derivativesInfo
- Publication number
- CA1173030A CA1173030A CA000370178A CA370178A CA1173030A CA 1173030 A CA1173030 A CA 1173030A CA 000370178 A CA000370178 A CA 000370178A CA 370178 A CA370178 A CA 370178A CA 1173030 A CA1173030 A CA 1173030A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- carbon atoms
- coch3
- atom
- along
- 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 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
- -1 alkyl hydrocarbon Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004965 chloroalkyl group Chemical group 0.000 claims abstract description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 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
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract 5
- 229930195733 hydrocarbon Natural products 0.000 claims abstract 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 239000000010 aprotic solvent Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 229940086542 triethylamine Drugs 0.000 claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 8
- 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 abstract description 6
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 229910052799 carbon Inorganic materials 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 229960001701 chloroform Drugs 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 4
- 229940109171 rifamycin sv Drugs 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 2
- 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 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229940023064 escherichia coli Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin 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)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical class C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241001522878 Escherichia coli B Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960001225 rifampicin Drugs 0.000 description 1
- 229960003292 rifamycin Drugs 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 238000005406 washing 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
- C07D498/12—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
-
- 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
- C07D498/22—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)
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8004848 | 1980-02-13 | ||
| GB8004848 | 1980-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1173030A true CA1173030A (en) | 1984-08-21 |
Family
ID=10511321
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000370178A Expired CA1173030A (en) | 1980-02-13 | 1981-02-05 | Rifamycin derivatives |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4305941A (en, 2012) |
| JP (1) | JPS56128785A (en, 2012) |
| AT (1) | AT373891B (en, 2012) |
| AU (1) | AU533176B2 (en, 2012) |
| BE (1) | BE886395A (en, 2012) |
| CA (1) | CA1173030A (en, 2012) |
| CH (1) | CH649770A5 (en, 2012) |
| DE (1) | DE3100612A1 (en, 2012) |
| DK (1) | DK11381A (en, 2012) |
| ES (1) | ES8202030A1 (en, 2012) |
| FI (1) | FI69079C (en, 2012) |
| FR (1) | FR2475552A1 (en, 2012) |
| GR (1) | GR71862B (en, 2012) |
| IE (1) | IE51144B1 (en, 2012) |
| IL (1) | IL61861A (en, 2012) |
| IT (1) | IT1136558B (en, 2012) |
| NL (1) | NL8100695A (en, 2012) |
| NZ (1) | NZ195943A (en, 2012) |
| PT (1) | PT72499B (en, 2012) |
| SE (1) | SE453194B (en, 2012) |
| SU (1) | SU1047391A3 (en, 2012) |
| YU (1) | YU31781A (en, 2012) |
| ZA (1) | ZA8140B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8308166D0 (en) * | 1983-03-24 | 1983-05-05 | Erba Farmitalia | Preparation of azinomethyl-rifamycins |
| IT1201963B (it) * | 1983-03-24 | 1989-02-02 | Prodotti Antibiotici Spa | Derivati delle rifamicine e procedimento per la loro preparazione |
| US7122525B2 (en) * | 2001-11-21 | 2006-10-17 | Activbiotics, Inc. | Targeted therapeutics and uses thereof |
| US7820652B2 (en) * | 2003-09-24 | 2010-10-26 | Activbiotics Pharma, Llc | Regimen for the administration of rifamycin-class antibiotics |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DK345977A (da) * | 1976-09-30 | 1978-03-31 | Archifar Ind Chim Trentino | G rifamycinforbindelser og fremgangsmaade til deres fremstillin |
-
1980
- 1980-11-28 BE BE0/202966A patent/BE886395A/fr not_active IP Right Cessation
-
1981
- 1981-01-05 IE IE4/81A patent/IE51144B1/en unknown
- 1981-01-05 ZA ZA00810040A patent/ZA8140B/xx unknown
- 1981-01-05 US US06/222,618 patent/US4305941A/en not_active Expired - Fee Related
- 1981-01-06 IL IL61861A patent/IL61861A/xx unknown
- 1981-01-06 NZ NZ195943A patent/NZ195943A/xx unknown
- 1981-01-08 FI FI810038A patent/FI69079C/fi not_active IP Right Cessation
- 1981-01-08 GR GR63818A patent/GR71862B/el unknown
- 1981-01-12 DE DE19813100612 patent/DE3100612A1/de not_active Ceased
- 1981-01-12 DK DK11381A patent/DK11381A/da not_active Application Discontinuation
- 1981-01-14 CH CH207/81A patent/CH649770A5/it not_active IP Right Cessation
- 1981-01-19 IT IT19187/81A patent/IT1136558B/it active
- 1981-01-23 FR FR8101219A patent/FR2475552A1/fr active Granted
- 1981-01-23 AT AT0028181A patent/AT373891B/de not_active IP Right Cessation
- 1981-01-23 SU SU813232526A patent/SU1047391A3/ru active
- 1981-01-30 SE SE8100743A patent/SE453194B/sv not_active IP Right Cessation
- 1981-02-05 CA CA000370178A patent/CA1173030A/en not_active Expired
- 1981-02-06 YU YU00317/81A patent/YU31781A/xx unknown
- 1981-02-12 AU AU67253/81A patent/AU533176B2/en not_active Ceased
- 1981-02-12 ES ES499356A patent/ES8202030A1/es not_active Expired
- 1981-02-12 PT PT72499A patent/PT72499B/pt unknown
- 1981-02-12 NL NL8100695A patent/NL8100695A/nl not_active Application Discontinuation
- 1981-02-13 JP JP1913381A patent/JPS56128785A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IE51144B1 (en) | 1986-10-15 |
| DK11381A (da) | 1981-08-14 |
| ES499356A0 (es) | 1982-01-16 |
| NZ195943A (en) | 1982-12-07 |
| IL61861A (en) | 1984-03-30 |
| BE886395A (fr) | 1981-03-16 |
| SU1047391A3 (ru) | 1983-10-07 |
| YU31781A (en) | 1983-09-30 |
| IL61861A0 (en) | 1981-02-27 |
| IT1136558B (it) | 1986-09-03 |
| US4305941A (en) | 1981-12-15 |
| FI810038L (fi) | 1981-08-14 |
| AU6725381A (en) | 1981-08-20 |
| FI69079B (fi) | 1985-08-30 |
| SE453194B (sv) | 1988-01-18 |
| ATA28181A (de) | 1983-07-15 |
| JPS6155918B2 (en, 2012) | 1986-11-29 |
| DE3100612A1 (de) | 1981-12-03 |
| AT373891B (de) | 1984-02-27 |
| PT72499A (en) | 1981-03-01 |
| PT72499B (en) | 1982-02-05 |
| ZA8140B (en) | 1982-01-27 |
| FI69079C (fi) | 1985-12-10 |
| FR2475552A1 (fr) | 1981-08-14 |
| FR2475552B1 (en, 2012) | 1985-02-15 |
| NL8100695A (nl) | 1981-09-16 |
| IE810004L (en) | 1981-08-13 |
| JPS56128785A (en) | 1981-10-08 |
| GR71862B (en, 2012) | 1983-07-06 |
| SE8100743L (sv) | 1981-08-14 |
| AU533176B2 (en) | 1983-11-03 |
| CH649770A5 (it) | 1985-06-14 |
| IT8119187A0 (it) | 1981-01-19 |
| ES8202030A1 (es) | 1982-01-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3925366A (en) | 1,3-Oxazino(5,6-c)rifamycins and method for preparing the same | |
| DE2461526C2 (de) | N-Acylderivate von α-Aminobenzylpenicillinen | |
| CZ289671B6 (cs) | Heteroaroylové deriváty monocyklických beta-laktamových antibiotik, způsob jejich přípravy a meziprodukty tohoto postupu | |
| CA1173030A (en) | Rifamycin derivatives | |
| DK148979B (da) | Analogifremgangsmaade til fremstilling af quinoxalin-2-yl-ethenylketoner | |
| US4447432A (en) | Azino rifamycins | |
| CA1218650A (en) | Process for the synthesis of pyrido-imidazo- rifamycins | |
| EP0819112B1 (en) | Oxidative process for preparing narwedine derivatives | |
| US2776979A (en) | 1-nitroso-2-imidazolidone and process | |
| US2772280A (en) | Synthesis of 4-amino-3-isoxazolidone and its derivatives | |
| KR0178957B1 (ko) | 페넴 화합물 | |
| IE51358B1 (en) | 1,2,4-triazinylthiomethyl-3-cephem sulfoxides,process for their preparation and pharmaceutical compositions containing them | |
| GB2069485A (en) | Rifamycin derivatives | |
| FR2498606A1 (fr) | Derives de 5,6-didesoxyapramycine a activite antimicrobienne contre les bacteries gram-positives et gram-negatives | |
| SE441751B (sv) | Forfarande for framstellning av nya rifamyciner | |
| US4060527A (en) | Pyrido[2,3-c]-acridine-1-hydroxy-2-carboxylic acid derivatives | |
| CA1213278A (en) | 3-azinomethyl rifamycins | |
| EP0005140B1 (en) | Novel 4-desoxy-thiazolo (5,4-c) rifamycin derivatives and a process for preparing them | |
| US4190581A (en) | Novel penicillin derivatives | |
| KR840002046B1 (ko) | 세팔로스포린의 제조방법 | |
| EP0489733A1 (en) | Antibacterial pyrido(1,2,3-de)-1,4-benzoxazinone agents | |
| GB2073737A (en) | Rifamycins | |
| US4243596A (en) | (5-Nitro-2-furyl)vinylene-2-trimethylammonium bromide and method of preparing same | |
| DE1906194C3 (de) | 3-Brommethyl-A2 -cephalosporine und Verfahren zu ihrer Herstellung | |
| KR820001126B1 (ko) | 4-스펙티노마이실아민의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |