SE433747B - Forfarande for framstellning av 3-amino-rifamycin s och sv - Google Patents
Forfarande for framstellning av 3-amino-rifamycin s och svInfo
- Publication number
- SE433747B SE433747B SE7902064A SE7902064A SE433747B SE 433747 B SE433747 B SE 433747B SE 7902064 A SE7902064 A SE 7902064A SE 7902064 A SE7902064 A SE 7902064A SE 433747 B SE433747 B SE 433747B
- Authority
- SE
- Sweden
- Prior art keywords
- rifamycin
- amino
- give
- formula
- nitro
- Prior art date
Links
- SMPJCQGFZSDIHE-GVDHMVJUSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-amino-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C(N)=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 SMPJCQGFZSDIHE-GVDHMVJUSA-N 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 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 title claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229940109171 rifamycin sv Drugs 0.000 claims description 4
- 235000010288 sodium nitrite Nutrition 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- -1 potassium ferricyanide Chemical compound 0.000 claims description 2
- 125000004151 quinonyl group Chemical group 0.000 claims description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 2
- 229940081192 rifamycins Drugs 0.000 claims 2
- 229930189077 Rifamycin Natural products 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 229960003292 rifamycin Drugs 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000007858 starting material Substances 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9295/78A GB1591697A (en) | 1978-03-09 | 1978-03-09 | Process for producing 3-amino-rifamycins s and sv |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7902064L SE7902064L (sv) | 1979-09-10 |
| SE433747B true SE433747B (sv) | 1984-06-12 |
Family
ID=9869225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7902064A SE433747B (sv) | 1978-03-09 | 1979-03-08 | Forfarande for framstellning av 3-amino-rifamycin s och sv |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4217277A (de) |
| JP (1) | JPS54122297A (de) |
| KR (1) | KR810001509B1 (de) |
| AT (1) | AT364083B (de) |
| CA (1) | CA1095036A (de) |
| DE (1) | DE2908876A1 (de) |
| DK (1) | DK96079A (de) |
| ES (1) | ES477998A1 (de) |
| FR (1) | FR2419293A1 (de) |
| GB (1) | GB1591697A (de) |
| IT (1) | IT1113418B (de) |
| NL (1) | NL7901918A (de) |
| SE (1) | SE433747B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5653682A (en) * | 1979-10-09 | 1981-05-13 | Kanebo Ltd | Production of novel rifamycin derivative |
| RU2256663C2 (ru) * | 2003-07-22 | 2005-07-20 | Гитлин Исаак Григорьевич | Способ получения 3-аминорифампицина-s (варианты) |
| CN119243181B (zh) * | 2024-10-14 | 2025-10-10 | 河北欣港药业有限公司 | 一种微尺度下由利福霉素sv连续流电化学合成利福霉素s的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR208F (de) * | 1964-07-31 | |||
| 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 |
| IT1053787B (it) * | 1974-10-29 | 1981-10-10 | Pastori A | Macrolidi azotati e loro preparazione |
-
1978
- 1978-03-09 GB GB9295/78A patent/GB1591697A/en not_active Expired
-
1979
- 1979-02-14 IT IT20186/79A patent/IT1113418B/it active
- 1979-02-23 CA CA322,222A patent/CA1095036A/en not_active Expired
- 1979-02-23 ES ES477998A patent/ES477998A1/es not_active Expired
- 1979-02-26 JP JP2090579A patent/JPS54122297A/ja active Pending
- 1979-02-28 US US06/016,006 patent/US4217277A/en not_active Expired - Lifetime
- 1979-03-02 KR KR7900646A patent/KR810001509B1/ko not_active Expired
- 1979-03-05 AT AT0166279A patent/AT364083B/de active
- 1979-03-07 DE DE19792908876 patent/DE2908876A1/de active Pending
- 1979-03-08 FR FR7905944A patent/FR2419293A1/fr active Granted
- 1979-03-08 SE SE7902064A patent/SE433747B/sv not_active IP Right Cessation
- 1979-03-08 DK DK96079A patent/DK96079A/da unknown
- 1979-03-09 NL NL7901918A patent/NL7901918A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54122297A (en) | 1979-09-21 |
| GB1591697A (en) | 1981-06-24 |
| SE7902064L (sv) | 1979-09-10 |
| ES477998A1 (es) | 1979-10-16 |
| NL7901918A (nl) | 1979-09-11 |
| AT364083B (de) | 1981-09-25 |
| IT7920186A0 (it) | 1979-02-14 |
| KR810001509B1 (en) | 1981-10-25 |
| FR2419293A1 (fr) | 1979-10-05 |
| US4217277A (en) | 1980-08-12 |
| CA1095036A (en) | 1981-02-03 |
| IT1113418B (it) | 1986-01-20 |
| FR2419293B1 (de) | 1982-04-02 |
| DK96079A (da) | 1979-09-10 |
| ATA166279A (de) | 1981-02-15 |
| DE2908876A1 (de) | 1979-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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