NO784005L - Fremgangsmaate for fremstilling av 3-jod- og 3-bromorifamycin s. - Google Patents
Fremgangsmaate for fremstilling av 3-jod- og 3-bromorifamycin s.Info
- Publication number
- NO784005L NO784005L NO784005A NO784005A NO784005L NO 784005 L NO784005 L NO 784005L NO 784005 A NO784005 A NO 784005A NO 784005 A NO784005 A NO 784005A NO 784005 L NO784005 L NO 784005L
- Authority
- NO
- Norway
- Prior art keywords
- rifamycin
- iodine
- bromorifamycin
- pyridine
- bromine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
- 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 16
- 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 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 239000011630 iodine Substances 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 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 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 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 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- AHLYXGYSBJNLAA-UHFFFAOYSA-N [K].N#C[Fe](C#N)C#N Chemical compound [K].N#C[Fe](C#N)C#N AHLYXGYSBJNLAA-UHFFFAOYSA-N 0.000 description 2
- -1 bromine ions Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229940109171 rifamycin sv Drugs 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- C07D498/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT03620/77A IT1090759B (it) | 1977-11-29 | 1977-11-29 | Procedimento per la preparazione di 3 iodio e 3 bromo rifamicina s |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO784005L true NO784005L (no) | 1979-05-30 |
Family
ID=11110742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO784005A NO784005L (no) | 1977-11-29 | 1978-11-28 | Fremgangsmaate for fremstilling av 3-jod- og 3-bromorifamycin s. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4179438A (xx) |
| JP (1) | JPS5495599A (xx) |
| AR (1) | AR219775A1 (xx) |
| AT (1) | AT360652B (xx) |
| AU (1) | AU519242B2 (xx) |
| BE (1) | BE872294A (xx) |
| CA (1) | CA1099265A (xx) |
| CH (1) | CH636619A5 (xx) |
| DE (1) | DE2851312A1 (xx) |
| DK (1) | DK155797C (xx) |
| ES (1) | ES475471A1 (xx) |
| FI (1) | FI65254C (xx) |
| FR (1) | FR2410000A1 (xx) |
| GB (1) | GB2009744B (xx) |
| GR (1) | GR71727B (xx) |
| IT (1) | IT1090759B (xx) |
| LU (1) | LU80567A1 (xx) |
| NL (1) | NL7811558A (xx) |
| NO (1) | NO784005L (xx) |
| PT (1) | PT68840A (xx) |
| SE (1) | SE439168B (xx) |
| YU (1) | YU279178A (xx) |
| ZA (1) | ZA786299B (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL100642A (en) * | 1991-01-28 | 1995-11-27 | Lepetit Spa | Process for the preparation of (2-) diethylamino (rifmacin P) AED / P (and its new intermediate |
| 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 |
| 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 |
| US7247634B2 (en) * | 2004-01-13 | 2007-07-24 | Cumbre Pharmaceuticals Inc. | Rifamycin derivatives effective against drug-resistant microbes |
| US9415112B2 (en) | 2011-06-20 | 2016-08-16 | Rutgers, The State University Of New Jersey | Bipartite inhibitors of bacterial RNA polymerase |
| US9108968B2 (en) | 2012-04-25 | 2015-08-18 | Ppg Industries Ohio, Inc. | Methods for producing 1,5,7-triazabicyclo[4.4.0]dec-5-ene by reaction of a disubstituted carbodiimide and dipropylene triamine |
| EP3134415A4 (en) * | 2014-04-19 | 2017-10-25 | Granules India Limited | An improved process for the preparation of rifamycin derivatives |
| DK3645539T3 (da) | 2017-06-26 | 2021-05-10 | Biofer Spa | Pyrido-imidazo-rifamycin-derivater som antibakterielt middel |
| CN109400628A (zh) * | 2018-12-26 | 2019-03-01 | 重庆华邦胜凯制药有限公司 | 一种利福布汀中间体的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1053787B (it) * | 1974-10-29 | 1981-10-10 | Pastori A | Macrolidi azotati e loro preparazione |
| GB1591696A (en) * | 1978-03-09 | 1981-06-24 | Archifar Lab Chim Farm | 3-nitro-rifamycins s and sv |
-
1977
- 1977-11-29 IT IT03620/77A patent/IT1090759B/it active
-
1978
- 1978-11-06 US US05/957,844 patent/US4179438A/en not_active Expired - Lifetime
- 1978-11-08 ZA ZA00786299A patent/ZA786299B/xx unknown
- 1978-11-23 AT AT837078A patent/AT360652B/de not_active IP Right Cessation
- 1978-11-23 AU AU41867/78A patent/AU519242B2/en not_active Expired
- 1978-11-23 LU LU80567A patent/LU80567A1/xx unknown
- 1978-11-24 NL NL7811558A patent/NL7811558A/xx not_active Application Discontinuation
- 1978-11-27 FR FR7833394A patent/FR2410000A1/fr active Granted
- 1978-11-27 AR AR274585A patent/AR219775A1/es active
- 1978-11-27 DE DE19782851312 patent/DE2851312A1/de not_active Withdrawn
- 1978-11-27 BE BE2057442A patent/BE872294A/xx not_active IP Right Cessation
- 1978-11-27 YU YU02791/78A patent/YU279178A/xx unknown
- 1978-11-28 ES ES475471A patent/ES475471A1/es not_active Expired
- 1978-11-28 NO NO784005A patent/NO784005L/no unknown
- 1978-11-28 DK DK530978A patent/DK155797C/da not_active IP Right Cessation
- 1978-11-28 SE SE7812231A patent/SE439168B/sv not_active IP Right Cessation
- 1978-11-28 CA CA317,009A patent/CA1099265A/en not_active Expired
- 1978-11-28 GR GR57753A patent/GR71727B/el unknown
- 1978-11-28 CH CH1217978A patent/CH636619A5/it not_active IP Right Cessation
- 1978-11-28 FI FI783639A patent/FI65254C/fi not_active IP Right Cessation
- 1978-11-28 JP JP14704878A patent/JPS5495599A/ja active Granted
- 1978-11-28 PT PT68840A patent/PT68840A/pt unknown
- 1978-11-29 GB GB7846449A patent/GB2009744B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2410000A1 (fr) | 1979-06-22 |
| GB2009744B (en) | 1982-05-26 |
| CA1099265A (en) | 1981-04-14 |
| ES475471A1 (es) | 1979-06-01 |
| US4179438A (en) | 1979-12-18 |
| CH636619A5 (it) | 1983-06-15 |
| ZA786299B (en) | 1979-10-31 |
| AT360652B (de) | 1981-01-26 |
| DK155797B (da) | 1989-05-16 |
| GB2009744A (en) | 1979-06-20 |
| LU80567A1 (fr) | 1979-03-22 |
| GR71727B (xx) | 1983-06-22 |
| FI65254C (fi) | 1984-04-10 |
| DK155797C (da) | 1989-10-02 |
| BE872294A (fr) | 1979-03-16 |
| ATA837078A (de) | 1980-06-15 |
| JPS625159B2 (xx) | 1987-02-03 |
| DE2851312A1 (de) | 1979-07-12 |
| AR219775A1 (es) | 1980-09-15 |
| SE7812231L (sv) | 1979-05-30 |
| PT68840A (en) | 1978-12-01 |
| JPS5495599A (en) | 1979-07-28 |
| NL7811558A (nl) | 1979-05-31 |
| SE439168B (sv) | 1985-06-03 |
| AU519242B2 (en) | 1981-11-19 |
| FI65254B (fi) | 1983-12-30 |
| FI783639A (fi) | 1979-05-30 |
| YU279178A (en) | 1982-10-31 |
| IT1090759B (it) | 1985-06-26 |
| AU4186778A (en) | 1979-06-07 |
| DK530978A (da) | 1979-05-30 |
| FR2410000B1 (xx) | 1983-10-28 |
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