JPS5610193A - Preparation of rifamycin derivative - Google Patents
Preparation of rifamycin derivativeInfo
- Publication number
- JPS5610193A JPS5610193A JP8560979A JP8560979A JPS5610193A JP S5610193 A JPS5610193 A JP S5610193A JP 8560979 A JP8560979 A JP 8560979A JP 8560979 A JP8560979 A JP 8560979A JP S5610193 A JPS5610193 A JP S5610193A
- Authority
- JP
- Japan
- Prior art keywords
- rifamycin
- compound
- formula
- hydrolyzing
- prepared
- 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.)
- Pending
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 abstract 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical class 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 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 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 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000000814 tuberculostatic agent Substances 0.000 abstract 1
Landscapes
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
PURPOSE: To prepare the titled compound useful as an intermediate of an antituberculous agent rifampicin SV and other useful rifamycin derivatives, easily, by hydrolyzing a specific derivative of rifamycin S under basic conditions.
CONSTITUTION: The objective compound of formula II is prepared, without using an oxidizing agent, by hydrolyzing a compound of formula I (R is alkyl, aryl, or benzyl) in a solvent such as hydrous tetrahydrofuran, hydrous dioxane, etc., in the presence of an excessive organic base such as triethylamine, pyrrolidine, etc., pref. in nitrogen atmosphere, at about room temperature for 10W20hr. The compound of formula I can be prepared from rifamycin S in high yield, without using an oxidizing agent.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8560979A JPS5610193A (en) | 1979-07-05 | 1979-07-05 | Preparation of rifamycin derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8560979A JPS5610193A (en) | 1979-07-05 | 1979-07-05 | Preparation of rifamycin derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS5610193A true JPS5610193A (en) | 1981-02-02 |
Family
ID=13863565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8560979A Pending JPS5610193A (en) | 1979-07-05 | 1979-07-05 | Preparation of rifamycin derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5610193A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590498A (en) * | 1982-12-27 | 1986-05-20 | Shin Nisso Kako Co., Ltd. | Chromogenic recording materials |
-
1979
- 1979-07-05 JP JP8560979A patent/JPS5610193A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590498A (en) * | 1982-12-27 | 1986-05-20 | Shin Nisso Kako Co., Ltd. | Chromogenic recording materials |
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