ES449257A1 - PROCESS FOR THE PREPARATION OF NEW 16-ETERS OF FUSID ACID DERIVATIVES. - Google Patents
PROCESS FOR THE PREPARATION OF NEW 16-ETERS OF FUSID ACID DERIVATIVES.Info
- Publication number
- ES449257A1 ES449257A1 ES449257A ES449257A ES449257A1 ES 449257 A1 ES449257 A1 ES 449257A1 ES 449257 A ES449257 A ES 449257A ES 449257 A ES449257 A ES 449257A ES 449257 A1 ES449257 A1 ES 449257A1
- Authority
- ES
- Spain
- Prior art keywords
- radical
- formula
- compound
- sulfur
- oxygen
- 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
- 239000002253 acid Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 239000001301 oxygen Substances 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 239000011593 sulfur Chemical group 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl 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
- 125000004429 atom Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- IECPWNUMDGFDKC-MZJAQBGESA-N fusidic acid Chemical class 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 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
Process for the preparation of new 16-ethers of derivatives of fusidic acid, of formula I **(See formula)** wherein the C24-25 bond is a single or double bond, and where C1 and C2 represent (see formula) or oxygen; A represents oxygen, sulfur, or a sulfinyl radical; R1 represents a straight or branched chain alkyl radical having 1 to 8 carbon atoms, an alkenyl or alkynyl radical having 2 to 6 carbon atoms, a cycloalkyl radical having 3 to 7 ring carbon atoms alicyclic, an aryl, aralkyl, or heterocyclylalkyl radical, or an heterocyclic radical having 5 or 6 atoms per ring and containing oxygen, sulfur, or nitrogen atoms, optionally all radicals being substituted R1; and the pharmaceutically acceptable salts and easily hydrolyzable esters thereof, consisting of reacting a compound of formula Vb **(See formula)** wherein Q1 is Q1 or (see formula), where R2 is an alkanoyl, aralkanoyl or aroyl radical; Q2 is as defined above; Y represents, chlorine, bromine or iodine; and R3 represents a straight or ratified alkyl radical, having 1 to 6 carbon atoms, an aralkyl radical, an alkanoyl- or aroylmethyl radical, an alkanoyl- or aroyl-oxyalkyl radical, an alkyloxymethyl or cyanomethyl radical; with a compound of formula VII: R1-A-H, where R1 is as defined above and A represents oxygen or sulfur, giving a compound of formula VIII: **(See formula)** wherein Q1, Q2, R1 and R3 are as defined above, and A is oxygen or sulfur, a compound which is subsequently subjected to hydrolysis, if desired, and a compound of formula I, where A is sulfur, it is optionally oxidized to a compound of formula I, where A is a sulfinyl radical; and the free acid can be transformed into a pharmaceutically acceptable salt or an easily hydrolyzable ester thereof. (Machine-translation by Google Translate, not legally binding)
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 (1)
| Publication Number | Publication Date |
|---|---|
| ES449257A1 true ES449257A1 (en) | 1977-12-16 |
Family
ID=26258548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES449257A Expired ES449257A1 (en) | 1975-06-25 | 1976-06-25 | PROCESS FOR THE PREPARATION OF NEW 16-ETERS OF FUSID 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 |
| JP3350048B2 (en) * | 1989-07-07 | 2002-11-25 | アンドルシェルシュ・インコーポレイテッド | Methods for treating androgen-related diseases |
| TW239145B (en) * | 1992-05-21 | 1995-01-21 | Endorech Inc |
-
1976
- 1976-06-08 GR GR50927A patent/GR60362B/en unknown
- 1976-06-09 NZ NZ181107A patent/NZ181107A/en unknown
- 1976-06-09 IE IE1227/76A patent/IE43478B1/en unknown
- 1976-06-16 AT AT438776A patent/AT345979B/en active
- 1976-06-22 FR FR7618949A patent/FR2315296A1/en active Granted
- 1976-06-23 PT PT65261A patent/PT65261A/en unknown
- 1976-06-23 IT IT68542/76A patent/IT1062245B/en active
- 1976-06-24 FI FI761863A patent/FI55852C/en not_active IP Right Cessation
- 1976-06-24 CA CA255,603A patent/CA1064906A/en not_active Expired
- 1976-06-24 JP JP51073931A patent/JPS523051A/en active Granted
- 1976-06-24 SE SE7607322A patent/SE7607322L/en unknown
- 1976-06-24 LU LU75239A patent/LU75239A1/xx unknown
- 1976-06-24 DE DE2628360A patent/DE2628360C2/en not_active Expired
- 1976-06-24 AU AU15250/76A patent/AU500027B2/en not_active Expired
- 1976-06-25 DK DK285776A patent/DK143905C/en not_active IP Right Cessation
- 1976-06-25 SU SU762374610A patent/SU799670A3/en active
- 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 |
|---|---|
| IT1062245B (en) | 1983-09-20 |
| JPS6350360B2 (en) | 1988-10-07 |
| FI55852C (en) | 1979-10-10 |
| FR2315296A1 (en) | 1977-01-21 |
| DE2628360C2 (en) | 1986-11-06 |
| SU799670A3 (en) | 1981-01-23 |
| CA1064906A (en) | 1979-10-23 |
| IE43478L (en) | 1976-12-25 |
| FI55852B (en) | 1979-06-29 |
| GR60362B (en) | 1978-05-19 |
| PT65261B (en) | 1977-12-07 |
| AU1525076A (en) | 1978-01-05 |
| NZ181107A (en) | 1978-11-13 |
| DK285776A (en) | 1976-12-26 |
| LU75239A1 (en) | 1977-03-16 |
| DK143905C (en) | 1982-04-19 |
| SE7607322L (en) | 1976-12-26 |
| NL7606983A (en) | 1976-12-28 |
| AU500027B2 (en) | 1979-05-10 |
| JPS523051A (en) | 1977-01-11 |
| DE2628360A1 (en) | 1977-01-13 |
| FR2315296B1 (en) | 1980-11-07 |
| ATA438776A (en) | 1978-02-15 |
| PT65261A (en) | 1976-07-01 |
| IE43478B1 (en) | 1981-03-11 |
| FI761863A7 (en) | 1976-12-26 |
| AT345979B (en) | 1978-10-10 |
| DK143905B (en) | 1981-10-26 |
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