GB1161908A - Antibiotically Active Derivatives of Rifamycin S and Rifamycin SV and Process for their Manufacture - Google Patents
Antibiotically Active Derivatives of Rifamycin S and Rifamycin SV and Process for their ManufactureInfo
- Publication number
- GB1161908A GB1161908A GB3744266A GB3744266A GB1161908A GB 1161908 A GB1161908 A GB 1161908A GB 3744266 A GB3744266 A GB 3744266A GB 3744266 A GB3744266 A GB 3744266A GB 1161908 A GB1161908 A GB 1161908A
- Authority
- GB
- United Kingdom
- Prior art keywords
- rifamycin
- substituted
- derivative
- salt
- aliphatic character
- 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
- 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 title abstract 7
- 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 abstract 6
- 229940109171 rifamycin sv Drugs 0.000 title abstract 6
- HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 4
- 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 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000002955 isolation Methods 0.000 abstract 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229930189077 Rifamycin Natural products 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 abstract 1
- 229940081192 rifamycins Drugs 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,161,908. Rifamycins. CIBA Ltd. 22 Aug., 1966 [24 Aug., 1965], No. 37442/66. Heading C2A. The invention comprises a 3-substituted derivative of rifamycin S or of rifamycin SV, or of a 16, 17, 18, 19-tetrahydro or 16, 17, 18, 19, 28, 29-hexahydro derivative of rifamycin S or rifamycin SV, the substituent in position 3 being a free or aliphatically substituted amino group, namely, an amino group substituted by one or two monovalent hydrocarbon radicals of aliphatic character, which may be the same or different, or by a divalent hydrocarbon radical of aliphatic character, which hydrocarbons of aliphatic character may be interrupted in the carbon chain by one or more hetero atoms and may be unsubstituted or substituted, e.g. a heterocyclic grouping which is not aromatic; a salt thereof or a quaternary ammonium compound thereof. Examples thereof are 3-morpholino-rifamycin S, 3-pyrrolidino-rifamycin SV, 3-benzylamino rifamycin S, 3-piperidino-rifamycin SV, 3-cyclohexylaminorifamycin S and 3-methylamino-rifamycin SV. Rifamycin S has the following formula The compounds are prepared by reacting rifamycin S, or a 16, 17, 18, 19-tetrahydro or 16, 17, 18, 19, 28, 29 hexa-hydro derivative thereof, with ammonia or with a primary or secondary aliphatically substituted amine, and the 3-substituted derivative of rifamycin S and for the 3-substituted derivative of rifamycin SV so obtained is isolated, a hydroquinone obtained before or after the isolation being oxidized, if desired, to form a quinone and/or a quinone obtained before or after the isolation being reduced, if desired, to form a hydroquinone, and/or, if desired, a resulting compound is converted into a salt. Salts are formed with inorganic and organic acids (listed), and with metals. The picrates may be used in the purification of the bases. A pharmaceutical preparation having antibacterial activity comprises a rifamycin S or SV derivative as above, or a salt or quaternary ammonium compound thereof and a carrier. The compositions may be used orally, parenterally or topically. The rifamycin derivatives may also be added to animal fodders.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1187965A CH512510A (en) | 1965-08-24 | 1965-08-24 | Rifamycin s derivs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1161908A true GB1161908A (en) | 1969-08-20 |
Family
ID=4377763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3744266A Expired GB1161908A (en) | 1965-08-24 | 1966-08-22 | Antibiotically Active Derivatives of Rifamycin S and Rifamycin SV and Process for their Manufacture |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS511720B1 (en) |
| AT (1) | AT271722B (en) |
| BE (1) | BE685886A (en) |
| CH (1) | CH512510A (en) |
| CS (1) | CS158605B2 (en) |
| DE (2) | DE1795731A1 (en) |
| FR (4) | FR5995M (en) |
| GB (1) | GB1161908A (en) |
| MY (1) | MY7300140A (en) |
| NL (1) | NL152170B (en) |
| SE (1) | SE356519B (en) |
| SU (1) | SU378004A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252585A (en) | 1977-09-08 | 1981-02-24 | Rheem Manufacturing Company | Method for making a plastic container |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1048565B (en) * | 1975-05-15 | 1980-12-20 | Archifar Ind Chim Trentino | AROMATIC AMINAS |
| DK345977A (en) * | 1976-09-30 | 1978-03-31 | Archifar Ind Chim Trentino | G RIFAMYCIN COMPOUNDS AND PROCEDURE FOR THEIR PREPARATION |
| IT7828731A0 (en) * | 1977-11-05 | 1978-10-13 | Archifar Lab Chim Farm | PROCEDURE FOR THE PRODUCTION OF 3-AMINODERIVATIVES OF RIFAMICIN S. |
| GB1591697A (en) * | 1978-03-09 | 1981-06-24 | Archifar Lab Chim Farm | Process for producing 3-amino-rifamycins s and sv |
| IT1135270B (en) * | 1980-04-12 | 1986-08-20 | Erba Farmitalia | 3-amidino-ANSAMICINE |
-
1965
- 1965-08-24 CH CH1187965A patent/CH512510A/en not_active IP Right Cessation
-
1966
- 1966-08-17 CS CS541366A patent/CS158605B2/cs unknown
- 1966-08-18 DE DE19661795731 patent/DE1795731A1/en not_active Withdrawn
- 1966-08-18 DE DE19661670377 patent/DE1670377C3/en not_active Expired
- 1966-08-22 GB GB3744266A patent/GB1161908A/en not_active Expired
- 1966-08-23 BE BE685886D patent/BE685886A/xx unknown
- 1966-08-23 SU SU1098428A patent/SU378004A3/ru active
- 1966-08-23 AT AT800966A patent/AT271722B/en active
- 1966-08-23 NL NL6611867A patent/NL152170B/en not_active IP Right Cessation
- 1966-08-24 JP JP41055316A patent/JPS511720B1/ja active Pending
- 1966-08-28 SE SE1134966A patent/SE356519B/xx unknown
- 1966-11-22 FR FR84416A patent/FR5995M/fr not_active Expired
- 1966-11-22 FR FR84414A patent/FR5993M/fr not_active Expired
- 1966-11-22 FR FR84417A patent/FR5996M/fr not_active Expired
- 1966-11-22 FR FR84415A patent/FR5994M/fr not_active Expired
-
1973
- 1973-12-31 MY MY7300140A patent/MY7300140A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4252585A (en) | 1977-09-08 | 1981-02-24 | Rheem Manufacturing Company | Method for making a plastic container |
Also Published As
| Publication number | Publication date |
|---|---|
| NL152170B (en) | 1977-02-15 |
| DE1670377A1 (en) | 1972-04-06 |
| CH512510A (en) | 1971-09-15 |
| BE685886A (en) | 1967-02-23 |
| FR5994M (en) | 1968-04-29 |
| FR5995M (en) | 1968-04-29 |
| SE356519B (en) | 1973-05-28 |
| SU378004A3 (en) | 1973-04-17 |
| JPS511720B1 (en) | 1976-01-20 |
| MY7300140A (en) | 1973-12-31 |
| DE1795731A1 (en) | 1974-05-02 |
| DE1670377B2 (en) | 1973-07-19 |
| FR5996M (en) | 1968-04-29 |
| NL6611867A (en) | 1967-02-27 |
| DE1670377C3 (en) | 1974-02-28 |
| FR5993M (en) | 1968-04-29 |
| AT271722B (en) | 1969-06-10 |
| CS158605B2 (en) | 1974-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |