DE2846321C2 - - Google Patents
Info
- Publication number
- DE2846321C2 DE2846321C2 DE2846321A DE2846321A DE2846321C2 DE 2846321 C2 DE2846321 C2 DE 2846321C2 DE 2846321 A DE2846321 A DE 2846321A DE 2846321 A DE2846321 A DE 2846321A DE 2846321 C2 DE2846321 C2 DE 2846321C2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- rifamycin
- rifampicin
- hexahydro
- triazine
- 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 - Fee Related
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 69
- 238000006243 chemical reaction Methods 0.000 claims description 48
- 229960001225 rifampicin Drugs 0.000 claims description 44
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 38
- 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 claims description 36
- 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 claims description 36
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 claims description 28
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- 239000011541 reaction mixture Substances 0.000 claims description 22
- -1 2-morpholinoethyl Chemical group 0.000 claims description 15
- 235000006408 oxalic acid Nutrition 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 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 claims 2
- JQXXHWHPUNPDRT-YOPQJBRCSA-N chembl1332716 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\N1CCN(C)CC1 JQXXHWHPUNPDRT-YOPQJBRCSA-N 0.000 description 43
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229930040373 Paraformaldehyde Natural products 0.000 description 15
- 229920002866 paraformaldehyde Polymers 0.000 description 15
- 229960003292 rifamycin Drugs 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 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 description 11
- 229930189077 Rifamycin Natural products 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- XNJJKNFDJBAYSE-UHFFFAOYSA-N 1,3,5-tritert-butyl-1,3,5-triazinane Chemical compound CC(C)(C)N1CN(C(C)(C)C)CN(C(C)(C)C)C1 XNJJKNFDJBAYSE-UHFFFAOYSA-N 0.000 description 7
- 208000034656 Contusions Diseases 0.000 description 7
- 208000034526 bruise Diseases 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical class C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 4
- XIDQLVVZFFJREM-UHFFFAOYSA-N 4-[2-[3,5-bis(2-morpholin-4-ylethyl)-1,3,5-triazinan-1-yl]ethyl]morpholine Chemical compound C1COCCN1CCN(CN(CCN1CCOCC1)C1)CN1CCN1CCOCC1 XIDQLVVZFFJREM-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000003381 deacetylation reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 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 3
- RLQMACPTWZLKDP-UHFFFAOYSA-N aminomethanediol Chemical compound NC(O)O RLQMACPTWZLKDP-UHFFFAOYSA-N 0.000 description 3
- 230000006196 deacetylation Effects 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229940109171 rifamycin sv Drugs 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- BBNQHOMJRFAQBN-UPZFVJMDSA-N 3-formylrifamycin sv Chemical compound OC1=C(C(O)=C2C)C3=C(O)C(C=O)=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 BBNQHOMJRFAQBN-UPZFVJMDSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000036632 reaction speed Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 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 2
- 229940081192 rifamycins Drugs 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DPMZXMBOYHBELT-UHFFFAOYSA-N 1,3,5-trimethyl-1,3,5-triazinane Chemical compound CN1CN(C)CN(C)C1 DPMZXMBOYHBELT-UHFFFAOYSA-N 0.000 description 1
- LHQBCLSCLWYPAM-UHFFFAOYSA-N 1,3,5-tris(1-ethylpiperidin-3-yl)-1,3,5-triazinane Chemical compound C1N(CC)CCCC1N1CN(C2CN(CC)CCC2)CN(C2CN(CC)CCC2)C1 LHQBCLSCLWYPAM-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical group C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 1
- GBARYYVKTMYEIX-UHFFFAOYSA-N 4-[2-[3,5-bis(2-morpholin-4-ylethyl)-1,3,5-triazinan-1-yl]ethyl]morpholine;oxalic acid Chemical compound OC(=O)C(O)=O.C1COCCN1CCN(CN(CCN1CCOCC1)C1)CN1CCN1CCOCC1 GBARYYVKTMYEIX-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- UKOYDJAIEJKTHU-UHFFFAOYSA-N [tert-butyl(hydroxymethyl)amino]methanol Chemical compound CC(C)(C)N(CO)CO UKOYDJAIEJKTHU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 150000007514 bases Chemical class 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 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
-
- 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)
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB49148/77A GB1594134A (en) | 1977-11-25 | 1977-11-25 | Rifamycins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2846321A1 DE2846321A1 (de) | 1979-05-31 |
| DE2846321C2 true DE2846321C2 (en, 2012) | 1991-04-25 |
Family
ID=10451344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782846321 Granted DE2846321A1 (de) | 1977-11-25 | 1978-10-24 | Verfahren zur herstellung von rifamycinen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4174320A (en, 2012) |
| JP (1) | JPS5479299A (en, 2012) |
| AR (1) | AR219549A1 (en, 2012) |
| AT (1) | AT362062B (en, 2012) |
| AU (1) | AU524481B2 (en, 2012) |
| BE (1) | BE872233A (en, 2012) |
| CA (1) | CA1095035A (en, 2012) |
| DE (1) | DE2846321A1 (en, 2012) |
| FR (2) | FR2422665A1 (en, 2012) |
| GB (1) | GB1594134A (en, 2012) |
| GR (1) | GR72969B (en, 2012) |
| IN (2) | IN149404B (en, 2012) |
| IT (1) | IT1100590B (en, 2012) |
| PH (1) | PH15017A (en, 2012) |
| YU (2) | YU40836B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8308166D0 (en) * | 1983-03-24 | 1983-05-05 | Erba Farmitalia | Preparation of azinomethyl-rifamycins |
| GB8318072D0 (en) * | 1983-07-04 | 1983-08-03 | Lepetit Spa | Water-soluble rifampicin derivatives |
| GB8531887D0 (en) * | 1985-12-30 | 1986-02-05 | Lepetit Spa | Rifamycin sv derivatives |
| CN100383143C (zh) * | 2004-04-29 | 2008-04-23 | 薛荔 | 一锅烩合成利福平的方法 |
| US20090275594A1 (en) * | 2008-05-05 | 2009-11-05 | Macielag Mark J | 3-hydrazone piperazinyl rifamycin derivatives useful as antimicrobial agents |
| CN102660598B (zh) * | 2012-05-31 | 2014-01-22 | 河南省南街村（集团）有限公司 | 一种提高利福霉素sv发酵产量的方法 |
| CN103772413B (zh) * | 2014-02-07 | 2016-01-20 | 天津大学 | 一种利福平ⅱ晶型的制备方法 |
| CN111848639A (zh) * | 2020-07-09 | 2020-10-30 | 华东理工大学 | 一种合成利福平的工艺方法 |
| KR102688151B1 (ko) | 2021-12-28 | 2024-07-24 | 주식회사 종근당바이오 | Mnp가 저감된 리팜피신의 신규 제조방법 |
| EP4522625A1 (en) | 2022-05-13 | 2025-03-19 | OLON S.p.A. | Purification process of rifampicin from nitrosamines |
| WO2024009248A1 (en) | 2022-07-08 | 2024-01-11 | Olon S.P.A. | Method and assembly for the control of the formation of a nitrosamine impurity in a solid active pharmaceutical ingredient |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR208F (en, 2012) * | 1964-07-31 | |||
| NL145554B (nl) * | 1967-06-07 | 1975-04-15 | Lepetit Spa | Werkwijze voor het bereiden van een 3-formylrifamycine sv-derivaat |
| IT1046627B (it) * | 1970-06-01 | 1980-07-31 | Lepetit Spa | Composizioni antivirali contenenti derivati della rifaumicina sv |
| AR207762A1 (es) * | 1973-07-25 | 1976-10-29 | Archifar Ind Chim Trentino | Procedimiento para la preparacion de 3-((4-metil-1-piperazin-1-il)-imino)-metil-rifamicina sv o rifampicina |
| GB1478563A (en) * | 1975-03-05 | 1977-07-06 | Lepetit Spa | Rifamycin derivatives |
-
1977
- 1977-11-25 GB GB49148/77A patent/GB1594134A/en not_active Expired
-
1978
- 1978-09-13 CA CA311,214A patent/CA1095035A/en not_active Expired
- 1978-09-25 AU AU40168/78A patent/AU524481B2/en not_active Expired
- 1978-09-27 AR AR273873A patent/AR219549A1/es active
- 1978-09-27 US US05/946,530 patent/US4174320A/en not_active Expired - Lifetime
- 1978-10-24 DE DE19782846321 patent/DE2846321A1/de active Granted
- 1978-11-04 JP JP13622578A patent/JPS5479299A/ja active Granted
- 1978-11-15 PH PH21809A patent/PH15017A/en unknown
- 1978-11-20 FR FR7832600A patent/FR2422665A1/fr active Granted
- 1978-11-22 YU YU2730/78A patent/YU40836B/xx unknown
- 1978-11-22 AT AT833878A patent/AT362062B/de not_active IP Right Cessation
- 1978-11-23 BE BE191899A patent/BE872233A/xx not_active IP Right Cessation
- 1978-11-23 GR GR57719A patent/GR72969B/el unknown
- 1978-11-24 IT IT30194/78A patent/IT1100590B/it active
- 1978-11-25 IN IN1275/CAL/78A patent/IN149404B/en unknown
-
1979
- 1979-10-15 FR FR7925577A patent/FR2438048A1/fr active Granted
-
1981
- 1981-08-28 IN IN966/CAL/81A patent/IN151954B/en unknown
-
1982
- 1982-09-23 YU YU02117/82A patent/YU211782A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2422665B1 (en, 2012) | 1983-12-16 |
| YU211782A (en) | 1983-01-21 |
| YU273078A (en) | 1983-01-21 |
| US4174320A (en) | 1979-11-13 |
| CA1095035A (en) | 1981-02-03 |
| YU40836B (en) | 1986-06-30 |
| JPS5740155B2 (en, 2012) | 1982-08-25 |
| AU4016878A (en) | 1980-04-03 |
| AR219549A1 (es) | 1980-08-29 |
| FR2438048A1 (fr) | 1980-04-30 |
| PH15017A (en) | 1982-05-10 |
| IT1100590B (it) | 1985-09-28 |
| JPS5479299A (en) | 1979-06-25 |
| AT362062B (de) | 1981-04-27 |
| BE872233A (fr) | 1979-03-16 |
| AU524481B2 (en) | 1982-09-16 |
| IN151954B (en, 2012) | 1983-09-10 |
| DE2846321A1 (de) | 1979-05-31 |
| FR2422665A1 (fr) | 1979-11-09 |
| GB1594134A (en) | 1981-07-30 |
| FR2438048B1 (en, 2012) | 1982-12-03 |
| ATA833878A (de) | 1980-09-15 |
| IT7830194A0 (it) | 1978-11-24 |
| GR72969B (en, 2012) | 1984-01-20 |
| IN149404B (en, 2012) | 1981-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |