IE43478L - 16-ethers of fusidic acid - Google Patents
16-ethers of fusidic acidInfo
- Publication number
- IE43478L IE43478L IE761227A IE122776A IE43478L IE 43478 L IE43478 L IE 43478L IE 761227 A IE761227 A IE 761227A IE 122776 A IE122776 A IE 122776A IE 43478 L IE43478 L IE 43478L
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- desacetoxy
- alpha
- alkyl
- fusidinic
- Prior art date
Links
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical compound O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C(O)=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C IECPWNUMDGFDKC-MZJAQBGESA-N 0.000 title abstract 3
- 229960004675 fusidic acid Drugs 0.000 title abstract 3
- IECPWNUMDGFDKC-UHFFFAOYSA-N Fusicsaeure Natural products C12C(O)CC3C(=C(CCC=C(C)C)C(O)=O)C(OC(C)=O)CC3(C)C1(C)CCC1C2(C)CCC(O)C1C IECPWNUMDGFDKC-UHFFFAOYSA-N 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 abstract 2
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- -1 p-nitrobenzyl ester Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Abstract
Fusidinic acid derivs. of formula (I) and their pharmaceutically acceptable salts and easily hydrolysable esters are new: (C24 and C25 are joined by a single or double bond, Q1 and Q2 are H HO or O. A=O, S or SO. R1 = opt. branched 1-8C alkyl, 2-6C alkenyl or alkynyl, 3-7C cycloalkyl, aryl, aralkyl, heterocyclyl-alkyl or 5-6 membered heterocycle contg. O.S or N atoms; and all these gps. may be substd.). Prepn. is by reacting the 16 alpha-halo analogue, in which the 21-COOH is esterified, with R1AH then hydrolysing. (I) are useful for treating bacterial infections in humans and animals. They are more stable than fusidinic acid itself and are practically non-toxic. They may be administered in usual oral, parenteral or topical forms for an adult dose of 0.25-5, pref. 0.5-3g/day. A specifically claimed cpd., 16-desacetoxy-16 beta-isopropylthiofusidinic acid, was prepd. from 3-O-acetyl-16-desacetoxy-16 alpha-bromofusidinic acid p-nitrobenzyl ester, by reaction with isopropyl mercaptan, then hydrolysis with NaOH.
[FR2315296A1]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26989/75A GB1523803A (en) | 1975-06-25 | 1975-06-25 | 16-ethers of fusidic acid derivatives |
| GB4622975 | 1975-11-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43478L true IE43478L (en) | 1976-12-25 |
| IE43478B1 IE43478B1 (en) | 1981-03-11 |
Family
ID=26258548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1227/76A IE43478B1 (en) | 1975-06-25 | 1976-06-09 | New 16-ethers of fusidic acid derivatives |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS523051A (en) |
| AT (1) | AT345979B (en) |
| AU (1) | AU500027B2 (en) |
| CA (1) | CA1064906A (en) |
| DE (1) | DE2628360C2 (en) |
| DK (1) | DK143905C (en) |
| ES (1) | ES449257A1 (en) |
| FI (1) | FI55852C (en) |
| FR (1) | FR2315296A1 (en) |
| GR (1) | GR60362B (en) |
| IE (1) | IE43478B1 (en) |
| IT (1) | IT1062245B (en) |
| LU (1) | LU75239A1 (en) |
| NL (1) | NL7606983A (en) |
| NZ (1) | NZ181107A (en) |
| PT (1) | PT65261A (en) |
| SE (1) | SE7607322L (en) |
| SU (1) | SU799670A3 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1581335A (en) * | 1976-07-05 | 1980-12-10 | Leo Pharm Prod Ltd | 16-s-acyl derivatives of fusidic acid |
| US4548922A (en) * | 1983-06-06 | 1985-10-22 | Beth Israel Hospital | Drug administration |
| US5372996A (en) * | 1989-03-10 | 1994-12-13 | Endorecherche, Inc. | Method of treatment of androgen-related diseases |
| DK0595796T3 (en) * | 1989-07-07 | 2003-05-05 | Endorech Inc | Method of treating androgen-related diseases |
| KR950701527A (en) * | 1992-05-21 | 1995-04-28 | 라브리 페르낭 | INHIBITORS OF TESTOSTERONE 5α-REDUCTASE ACTIVITY |
-
1976
- 1976-06-08 GR GR50927A patent/GR60362B/en unknown
- 1976-06-09 IE IE1227/76A patent/IE43478B1/en unknown
- 1976-06-09 NZ NZ181107A patent/NZ181107A/en unknown
- 1976-06-16 AT AT438776A patent/AT345979B/en active
- 1976-06-22 FR FR7618949A patent/FR2315296A1/en active Granted
- 1976-06-23 IT IT68542/76A patent/IT1062245B/en active
- 1976-06-23 PT PT65261A patent/PT65261A/en unknown
- 1976-06-24 CA CA255,603A patent/CA1064906A/en not_active Expired
- 1976-06-24 AU AU15250/76A patent/AU500027B2/en not_active Expired
- 1976-06-24 FI FI761863A patent/FI55852C/en not_active IP Right Cessation
- 1976-06-24 DE DE2628360A patent/DE2628360C2/en not_active Expired
- 1976-06-24 LU LU75239A patent/LU75239A1/xx unknown
- 1976-06-24 SE SE7607322A patent/SE7607322L/en unknown
- 1976-06-24 JP JP51073931A patent/JPS523051A/en active Granted
- 1976-06-25 SU SU762374610A patent/SU799670A3/en active
- 1976-06-25 DK DK285776A patent/DK143905C/en not_active IP Right Cessation
- 1976-06-25 ES ES449257A patent/ES449257A1/en not_active Expired
- 1976-06-25 NL NL7606983A patent/NL7606983A/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS523051A (en) | 1977-01-11 |
| GR60362B (en) | 1978-05-19 |
| CA1064906A (en) | 1979-10-23 |
| FR2315296A1 (en) | 1977-01-21 |
| AU500027B2 (en) | 1979-05-10 |
| PT65261B (en) | 1977-12-07 |
| FI761863A7 (en) | 1976-12-26 |
| AT345979B (en) | 1978-10-10 |
| FI55852B (en) | 1979-06-29 |
| FI55852C (en) | 1979-10-10 |
| JPS6350360B2 (en) | 1988-10-07 |
| IT1062245B (en) | 1983-09-20 |
| ES449257A1 (en) | 1977-12-16 |
| AU1525076A (en) | 1978-01-05 |
| FR2315296B1 (en) | 1980-11-07 |
| DK143905C (en) | 1982-04-19 |
| DE2628360C2 (en) | 1986-11-06 |
| ATA438776A (en) | 1978-02-15 |
| NL7606983A (en) | 1976-12-28 |
| LU75239A1 (en) | 1977-03-16 |
| DE2628360A1 (en) | 1977-01-13 |
| DK285776A (en) | 1976-12-26 |
| SU799670A3 (en) | 1981-01-23 |
| NZ181107A (en) | 1978-11-13 |
| DK143905B (en) | 1981-10-26 |
| SE7607322L (en) | 1976-12-26 |
| IE43478B1 (en) | 1981-03-11 |
| PT65261A (en) | 1976-07-01 |
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