IL41017A - 3-(2-imidazolyl)derivatives of rifamycin - Google Patents
3-(2-imidazolyl)derivatives of rifamycinInfo
- Publication number
- IL41017A IL41017A IL41017A IL4101772A IL41017A IL 41017 A IL41017 A IL 41017A IL 41017 A IL41017 A IL 41017A IL 4101772 A IL4101772 A IL 4101772A IL 41017 A IL41017 A IL 41017A
- Authority
- IL
- Israel
- Prior art keywords
- rifamycin
- derivatives
- mono
- alkyl
- formula
- Prior art date
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
- -1 carbalkoxy Chemical group 0.000 claims abstract 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 150000001555 benzenes Chemical class 0.000 claims abstract 2
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000004985 diamines Chemical class 0.000 claims 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 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
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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
- 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
- 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.
[GB1388880A]
Claims (1)
1. C A 1 A rifamyein of the wherein represents and together represent a carbocyclic chain forming with the double bond of the adjacent imidazole moiety a benzene a mono or substituted benzene ring wherein the substituents are independently selected from lover lower halo or or unsubstituted or dioxo substituted fused polynuclear aromatic residue including condensed rings each of carbon and its 25 desaeetyl and A process for preparing a rifamyein of the formula wherein represents and together represent a carbocyclic chain forming the double bond of the adjacent imidazole moiety a benaene a mono or ring wherein the substituents are independently selected from lower lower or carboxy or unsubsti or or substituted fused polynuclear aromatic residue including condensed rings each of carbon and its and derivatives which condensing or its desaeetyl or derivatives with diamine of the formula wherein R and have the same meaning as in claim 1 and treating the obtained compound an oxidizing agent selected from cupric mercuric manganese isoamyl potassium ferricyanide and lead tetraacetate and when the obtained derivative is in the quinonic form reducing it to the corresponding hydroquinone with ascorbic December 1972 AGENT FOR APPLICANT insufficientOCRQuality
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1952572 | 1972-01-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41017A0 IL41017A0 (en) | 1973-02-28 |
| IL41017A true IL41017A (en) | 1976-06-30 |
Family
ID=11158763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41017A IL41017A (en) | 1972-01-19 | 1972-12-06 | 3-(2-imidazolyl)derivatives of rifamycin |
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 |
| EP1730154B1 (en) * | 2004-01-13 | 2012-10-17 | Cumbre IP Ventures, L.P. | 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 CH CH52873A patent/CH564554A5/xx not_active IP Right Cessation
- 1973-01-15 AU AU51099/73A patent/AU466810B2/en not_active Expired
- 1973-01-16 NL NL7300610.A patent/NL159388B/en unknown
- 1973-01-16 AR AR246143A patent/AR193313A1/en active
- 1973-01-16 DD DD168274A patent/DD103236A5/xx unknown
- 1973-01-17 AT AT37173A patent/AT320855B/en not_active IP Right Cessation
- 1973-01-17 LU LU66851A patent/LU66851A1/xx unknown
- 1973-01-18 CA CA161,561A patent/CA991636A/en not_active Expired
- 1973-01-18 JP JP48008230A patent/JPS518959B2/ja not_active Expired
- 1973-01-18 FR FR7301784A patent/FR2181676B1/fr not_active Expired
- 1973-01-18 DK DK28173AA patent/DK135995B/en unknown
- 1973-01-18 HU HULE675A patent/HU165387B/hu unknown
- 1973-01-18 ES ES410755A patent/ES410755A1/en not_active Expired
- 1973-01-18 SE SE7300711A patent/SE383152B/en unknown
- 1973-01-19 RO RO7300073551A patent/RO62774A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL159388B (en) | 1979-02-15 |
| JPS4880600A (en) | 1973-10-29 |
| DK135995B (en) | 1977-07-25 |
| CA991636A (en) | 1976-06-22 |
| IE36939L (en) | 1973-07-19 |
| NL7300610A (en) | 1973-07-23 |
| SU444372A3 (en) | 1974-09-25 |
| AU466810B2 (en) | 1975-11-13 |
| FR2181676B1 (en) | 1976-05-14 |
| BE794298A (en) | 1973-05-16 |
| RO62774A (en) | 1978-02-15 |
| AU5109973A (en) | 1974-07-18 |
| IL41017A0 (en) | 1973-02-28 |
| DD103236A5 (en) | 1974-01-12 |
| JPS518959B2 (en) | 1976-03-22 |
| DE2301766A1 (en) | 1973-07-26 |
| AR193313A1 (en) | 1973-04-11 |
| FR2181676A1 (en) | 1973-12-07 |
| SE383152B (en) | 1976-03-01 |
| ZA728306B (en) | 1973-07-25 |
| LU66851A1 (en) | 1973-03-19 |
| DK135995C (en) | 1978-01-23 |
| CH564554A5 (en) | 1975-07-31 |
| GB1388880A (en) | 1975-03-26 |
| DE2301766C3 (en) | 1980-11-20 |
| IE36939B1 (en) | 1977-03-30 |
| HU165387B (en) | 1974-08-28 |
| DE2301766B2 (en) | 1980-02-28 |
| AT320855B (en) | 1975-03-10 |
| ES410755A1 (en) | 1976-01-01 |
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