ES410755A1 - 3-imidazole derivatives of rifamycin sv - Google Patents
3-imidazole derivatives of rifamycin svInfo
- Publication number
- ES410755A1 ES410755A1 ES410755A ES410755A ES410755A1 ES 410755 A1 ES410755 A1 ES 410755A1 ES 410755 A ES410755 A ES 410755A ES 410755 A ES410755 A ES 410755A ES 410755 A1 ES410755 A1 ES 410755A1
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- formula
- deacetyl
- carbamyl
- mono
- 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 abstract 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title 1
- -1 carbalkoxy Chemical group 0.000 abstract 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229930189077 Rifamycin Natural products 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229960005070 ascorbic acid Drugs 0.000 abstract 1
- 235000010323 ascorbic acid Nutrition 0.000 abstract 1
- 239000011668 ascorbic acid Substances 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 abstract 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 abstract 1
- 229940101209 mercuric oxide Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 1
- 229960003292 rifamycin Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Procedure for preparing a 3-substituted rifamycin, of general formula: **(See formula)** where R represents hydrogen, lower alkyl, phenyl and phenylalkyl; R1 and R2 together represent a carbocyclic chain which forms with the double bond of the adjacent imidazole moiety a benzene ring, a mono or poly-substituted benzene ring in which the substituents are independently chosen from lower alkyl, lower alkoxy, halo, carboxy, carbalkoxy, sulfo, sulfamoyl, nitro, trifluoromethyl, carbamyl, mono- and di-lower-alkyl-carbamyl and methylenedioxy, a fused, substituted or substituted polynuclear aromatic moiety, including 2-3 fused rings of 5-6 carbon atoms each; and its derivatives 25-deacetyl and 16, 17, 18, 19, 28, 29-hexahydro; characterized in that it comprises condensing 3-formylriphamicin, or its 25-deacetyl or 16, 17, 18, 19, 28, 29-hexahydro derivatives, with an orthodiamine of formula: **(See formula)** wherein R, R1 and R2 are defined as above, and treating the compound obtained with a hydrogen acceptor selected from the group consisting of air, cupric salts, mercuric oxide, manganese dioxide, isoamyl nitrite, potassium ferricyanide and lead tetraacetate and, when the derivative obtained is in quinonic form, it is reduced to the corresponding hydroquinone with ascorbic acid. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1952572 | 1972-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES410755A1 true ES410755A1 (en) | 1976-01-01 |
Family
ID=11158763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES410755A Expired ES410755A1 (en) | 1972-01-19 | 1973-01-18 | 3-imidazole derivatives of rifamycin sv |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS518959B2 (en) |
| AR (1) | AR193313A1 (en) |
| AT (1) | AT320855B (en) |
| AU (1) | AU466810B2 (en) |
| BE (1) | BE794298A (en) |
| CA (1) | CA991636A (en) |
| CH (1) | CH564554A5 (en) |
| DD (1) | DD103236A5 (en) |
| DE (1) | DE2301766C3 (en) |
| DK (1) | DK135995B (en) |
| ES (1) | ES410755A1 (en) |
| FR (1) | FR2181676B1 (en) |
| GB (1) | GB1388880A (en) |
| HU (1) | HU165387B (en) |
| IE (1) | IE36939B1 (en) |
| IL (1) | IL41017A (en) |
| LU (1) | LU66851A1 (en) |
| NL (1) | NL159388B (en) |
| RO (1) | RO62774A (en) |
| SE (1) | SE383152B (en) |
| ZA (1) | ZA728306B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5480960U (en) * | 1977-11-18 | 1979-06-08 | ||
| US4447432A (en) * | 1981-11-17 | 1984-05-08 | Farmitalia Carlo Erba S.P.A. | Azino rifamycins |
| WO2005070940A2 (en) * | 2004-01-13 | 2005-08-04 | Cumbre Pharmaceuticals Inc. | Rifamycin derivatives effective against drug-resistant microbes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1325047A (en) * | 1969-08-11 | 1973-08-01 | Ciba Geigy Ag | Rifamycin compounds and processes for their manufacture |
-
0
- BE BE794298D patent/BE794298A/en unknown
-
1972
- 1972-11-23 ZA ZA728306A patent/ZA728306B/en unknown
- 1972-11-30 IE IE1666/72A patent/IE36939B1/en unknown
- 1972-12-06 IL IL41017A patent/IL41017A/en unknown
- 1972-12-28 GB GB5983272A patent/GB1388880A/en not_active Expired
-
1973
- 1973-01-15 DE DE2301766A patent/DE2301766C3/en not_active Expired
- 1973-01-15 AU AU51099/73A patent/AU466810B2/en not_active Expired
- 1973-01-15 CH CH52873A patent/CH564554A5/xx not_active IP Right Cessation
- 1973-01-16 DD DD168274A patent/DD103236A5/xx unknown
- 1973-01-16 NL NL7300610.A patent/NL159388B/en unknown
- 1973-01-16 AR AR246143A patent/AR193313A1/en active
- 1973-01-17 LU LU66851A patent/LU66851A1/xx unknown
- 1973-01-17 AT AT37173A patent/AT320855B/en not_active IP Right Cessation
- 1973-01-18 ES ES410755A patent/ES410755A1/en not_active Expired
- 1973-01-18 FR FR7301784A patent/FR2181676B1/fr not_active Expired
- 1973-01-18 SE SE7300711A patent/SE383152B/en unknown
- 1973-01-18 CA CA161,561A patent/CA991636A/en not_active Expired
- 1973-01-18 HU HULE675A patent/HU165387B/hu unknown
- 1973-01-18 JP JP48008230A patent/JPS518959B2/ja not_active Expired
- 1973-01-18 DK DK28173AA patent/DK135995B/en unknown
- 1973-01-19 RO RO7300073551A patent/RO62774A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HU165387B (en) | 1974-08-28 |
| DD103236A5 (en) | 1974-01-12 |
| AR193313A1 (en) | 1973-04-11 |
| DE2301766A1 (en) | 1973-07-26 |
| IE36939B1 (en) | 1977-03-30 |
| FR2181676B1 (en) | 1976-05-14 |
| GB1388880A (en) | 1975-03-26 |
| DE2301766C3 (en) | 1980-11-20 |
| JPS518959B2 (en) | 1976-03-22 |
| BE794298A (en) | 1973-05-16 |
| JPS4880600A (en) | 1973-10-29 |
| IL41017A (en) | 1976-06-30 |
| DK135995C (en) | 1978-01-23 |
| SU444372A3 (en) | 1974-09-25 |
| IE36939L (en) | 1973-07-19 |
| DE2301766B2 (en) | 1980-02-28 |
| AU5109973A (en) | 1974-07-18 |
| NL7300610A (en) | 1973-07-23 |
| RO62774A (en) | 1978-02-15 |
| FR2181676A1 (en) | 1973-12-07 |
| SE383152B (en) | 1976-03-01 |
| NL159388B (en) | 1979-02-15 |
| AU466810B2 (en) | 1975-11-13 |
| AT320855B (en) | 1975-03-10 |
| DK135995B (en) | 1977-07-25 |
| CA991636A (en) | 1976-06-22 |
| ZA728306B (en) | 1973-07-25 |
| IL41017A0 (en) | 1973-02-28 |
| LU66851A1 (en) | 1973-03-19 |
| CH564554A5 (en) | 1975-07-31 |
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