GB1388880A - 3-imidazole derivatives of rifamycin sv - Google Patents
3-imidazole derivatives of rifamycin svInfo
- Publication number
- GB1388880A GB1388880A GB5983272A GB5983272A GB1388880A GB 1388880 A GB1388880 A GB 1388880A GB 5983272 A GB5983272 A GB 5983272A GB 5983272 A GB5983272 A GB 5983272A GB 1388880 A GB1388880 A GB 1388880A
- Authority
- GB
- United Kingdom
- Prior art keywords
- rifamycin
- alkyl
- imidazole derivatives
- desacetyl
- 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 4
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract 3
- -1 carbalkoxy Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 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
- 150000001875 compounds Chemical class 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 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
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000004151 quinonyl group Chemical group 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
1388880 3-Imidazole derivatives of rifamycin SV GRUPPO LEPETIT SpA 28 Dec 1972 [19 Jan 1972] 59832/72 Heading C2C Novel 3-imidazole derivatives of rifamycin SV having the general Formula (I) and the corresponding 25-desacetyl and 16, 17, 18, 19, 28, 29-hexahydro derivatives, wherein R is hydrogen, C 1-6 alkyl, phenyl or phenyl- C 1-6 alkyl; and R 1 and R 2 together represent a carbocyclic residue forming with the double bond of the adjacent imidazol moiety a benzene ring; a mono- or poly-substituted benzene ring wherein the substituents are selected from C 1-6 alkyl, C 1-6 alkoxy, halo, carbalkoxy, carboxy, sulpho, sulphamoyl, nitro, trifluoromethyl, carbamyl, mono- and di-C 1-6 alkylcarbamyl and methylenedioxy; or a substituted or unsubstituted polynuclear aromatic radical composed of 2 or 3 fused rings each of 5-6 carbon atoms, are prepared by reacting 3-formylrifamycin SV or a 25-desacetyl or 16, 17, 18, 19, 28, 29-hexahydro derivative thereof, with an orthodiamine of formula wherein R, R 1 and R 2 are as defined above, and then oxidizing the product with air, a cupric salt, mercuric oxide, manganese dioxide, isoamyl nitrite, potassium ferricyanide or lead tetraacetate, and if the rifamycin moiety in the obtained compound is in the quinone form, reducing it to the corresponding hydroquinone with aqueous ascorbic acid. The compounds (I) have antibacterial, antiviral and anti-cancer activity and may be admixed with a pharmaceutical carrier to provide pharmaceutical compositions having such activity.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1952572 | 1972-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1388880A true GB1388880A (en) | 1975-03-26 |
Family
ID=11158763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5983272A Expired GB1388880A (en) | 1972-01-19 | 1972-12-28 | 3-imidazole derivatives of rifamycin sv |
Country Status (22)
| 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) |
| SU (1) | SU444372A3 (en) |
| ZA (1) | ZA728306B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005070940A3 (en) * | 2004-01-13 | 2005-09-29 | Cumbre Inc | Rifamycin derivatives effective against drug-resistant microbes |
Families Citing this family (2)
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA930734A (en) * | 1969-08-11 | 1973-07-24 | Bickel Hans | Antibiotically active 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 CH CH52873A patent/CH564554A5/xx not_active IP Right Cessation
- 1973-01-15 DE DE2301766A patent/DE2301766C3/en not_active Expired
- 1973-01-15 AU AU51099/73A patent/AU466810B2/en not_active Expired
- 1973-01-16 AR AR246143A patent/AR193313A1/en active
- 1973-01-16 NL NL7300610.A patent/NL159388B/en unknown
- 1973-01-16 DD DD168274A patent/DD103236A5/xx unknown
- 1973-01-17 LU LU66851A patent/LU66851A1/xx unknown
- 1973-01-17 SU SU1872137A patent/SU444372A3/en active
- 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 CA CA161,561A patent/CA991636A/en not_active Expired
- 1973-01-18 DK DK28173AA patent/DK135995B/en unknown
- 1973-01-18 FR FR7301784A patent/FR2181676B1/fr not_active Expired
- 1973-01-18 JP JP48008230A patent/JPS518959B2/ja not_active Expired
- 1973-01-18 HU HULE675A patent/HU165387B/hu unknown
- 1973-01-18 SE SE7300711A patent/SE383152B/en unknown
- 1973-01-19 RO RO7300073551A patent/RO62774A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005070940A3 (en) * | 2004-01-13 | 2005-09-29 | Cumbre Inc | Rifamycin derivatives effective against drug-resistant microbes |
| US7247634B2 (en) | 2004-01-13 | 2007-07-24 | Cumbre Pharmaceuticals Inc. | Rifamycin derivatives effective against drug-resistant microbes |
Also Published As
| Publication number | Publication date |
|---|---|
| AR193313A1 (en) | 1973-04-11 |
| ZA728306B (en) | 1973-07-25 |
| JPS518959B2 (en) | 1976-03-22 |
| ES410755A1 (en) | 1976-01-01 |
| IE36939L (en) | 1973-07-19 |
| LU66851A1 (en) | 1973-03-19 |
| DE2301766A1 (en) | 1973-07-26 |
| CA991636A (en) | 1976-06-22 |
| FR2181676A1 (en) | 1973-12-07 |
| AT320855B (en) | 1975-03-10 |
| FR2181676B1 (en) | 1976-05-14 |
| AU5109973A (en) | 1974-07-18 |
| RO62774A (en) | 1978-02-15 |
| SE383152B (en) | 1976-03-01 |
| CH564554A5 (en) | 1975-07-31 |
| NL159388B (en) | 1979-02-15 |
| NL7300610A (en) | 1973-07-23 |
| DK135995B (en) | 1977-07-25 |
| IL41017A0 (en) | 1973-02-28 |
| DK135995C (en) | 1978-01-23 |
| AU466810B2 (en) | 1975-11-13 |
| BE794298A (en) | 1973-05-16 |
| DD103236A5 (en) | 1974-01-12 |
| IL41017A (en) | 1976-06-30 |
| IE36939B1 (en) | 1977-03-30 |
| DE2301766C3 (en) | 1980-11-20 |
| DE2301766B2 (en) | 1980-02-28 |
| JPS4880600A (en) | 1973-10-29 |
| HU165387B (en) | 1974-08-28 |
| SU444372A3 (en) | 1974-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |