GB1366080A - 6alpha,15alpha-dihydroxy-steroids - Google Patents
6alpha,15alpha-dihydroxy-steroidsInfo
- Publication number
- GB1366080A GB1366080A GB3338271A GB3338271A GB1366080A GB 1366080 A GB1366080 A GB 1366080A GB 3338271 A GB3338271 A GB 3338271A GB 3338271 A GB3338271 A GB 3338271A GB 1366080 A GB1366080 A GB 1366080A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dione
- ene
- dihydroxyandrost
- pregnane
- followed
- 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
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 abstract 2
- WVAMBAWFDOYFOD-BMSLSITRSA-N (6s,8r,9s,10r,13s,14s)-6-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3C[C@H](O)C2=C1 WVAMBAWFDOYFOD-BMSLSITRSA-N 0.000 abstract 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 abstract 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 abstract 1
- 241001133184 Colletotrichum agaves Species 0.000 abstract 1
- 241000223197 Fusarium lateritium Species 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 229960005305 adenosine Drugs 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 abstract 1
- 230000033444 hydroxylation Effects 0.000 abstract 1
- 238000005805 hydroxylation reaction Methods 0.000 abstract 1
- 230000000813 microbial effect Effects 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 150000003431 steroids Chemical class 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1366080 6α,15α-Dihydroxy steroids NELSON RESEARCH & DEVELOPMENT CO 1 Dec 1971 [3 Dec 1970 15 July 1971] 57533/70 and 33382/71 Heading C2U The invention comprises 6α,15α-dihydroxyandrost-4-ene-3,17-dione; 2α-methyl-6α,15α, 17# - trihydroxyandrost - 4 - en - 3 - one; 6α, 15α - dihydroxypregn - 4 - ene - 3,20 - dione; 6α,11#,15α,17α,21 - pentahydroxypregn - 4 - ene- 3,20 - dione; and 6α,11#,15α,17α,21 - pentahydroxy - 5α - pregnane - 3,20 - dione. These compounds are prepared from the corresponding 15-unsubstituted compounds by microbial hydroxylation with Gibberella baccata or Colletotrichum antirrhini. 2# - Methyl - 6α,17# - dihydroxyandrost - 4 - en- 3-one is prepared from 6α-hydroxyandrost-4- ene-3,17-dione by NaBH 4 reduction to give 6α, 17#-dihydroxyandrost-4-en-3-one followed by reaction with ethyl oxalate/sodium hydride to give 2# - ethoxalyl - 6α,17# - dihydroxyandrost - 4 -en-3- one followed by reaction with MeI/K 2 CO 3 / acetone and then NaOEt/EtOH. 6α,11#,17α,21 - Tetrahydroxy - 5α - pregnane- 3,20-dione is prepared from 3,20-bis-(ethylenedioxy) - 11#,17α,21 - trihydroxypregn - 5 - ene by reaction with B 2 H 6 and then alkaline H 2 O 2 to give 3,20-bis-(ethylenedioxy)6α,11#,17α,21- tetrahydroxy-5α-pregnane followed by acidolysis of the ketal groups. The inventive compounds are said to block the actions of prostaglandins and adenosine 3<SP>1</SP>, 5<SP>1</SP>-(cyclic monophosphate), and may be made up with carriers into pharmaceutical compositions for oral. parenteral and topical administration.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3338271A GB1366080A (en) | 1970-12-03 | 1971-07-15 | 6alpha,15alpha-dihydroxy-steroids |
| AU36325/71A AU3632571A (en) | 1970-12-03 | 1971-11-30 | Steroid comounds |
| DE19712159874 DE2159874A1 (en) | 1970-12-03 | 1971-12-02 | STEROID CONNECTIONS |
| FR7143350A FR2116508A1 (en) | 1970-12-03 | 1971-12-02 | |
| AR23939571A AR196867A1 (en) | 1970-12-03 | 1971-12-02 | METHOD FOR THE PREPARATION OF ALPHA-STEROIDS ANTAGONISTS OF PROSTAGLANDINS |
| BE776238A BE776238A (en) | 1970-12-03 | 1971-12-03 | STEROID COMPOUNDS, THEIR PREPARATIONS AND THEIR USES |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5753370 | 1970-12-03 | ||
| GB3338271A GB1366080A (en) | 1970-12-03 | 1971-07-15 | 6alpha,15alpha-dihydroxy-steroids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1366080A true GB1366080A (en) | 1974-09-11 |
Family
ID=26261849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3338271A Expired GB1366080A (en) | 1970-12-03 | 1971-07-15 | 6alpha,15alpha-dihydroxy-steroids |
Country Status (6)
| Country | Link |
|---|---|
| AR (1) | AR196867A1 (en) |
| AU (1) | AU3632571A (en) |
| BE (1) | BE776238A (en) |
| DE (1) | DE2159874A1 (en) |
| FR (1) | FR2116508A1 (en) |
| GB (1) | GB1366080A (en) |
-
1971
- 1971-07-15 GB GB3338271A patent/GB1366080A/en not_active Expired
- 1971-11-30 AU AU36325/71A patent/AU3632571A/en not_active Expired
- 1971-12-02 DE DE19712159874 patent/DE2159874A1/en active Pending
- 1971-12-02 FR FR7143350A patent/FR2116508A1/fr not_active Withdrawn
- 1971-12-02 AR AR23939571A patent/AR196867A1/en active
- 1971-12-03 BE BE776238A patent/BE776238A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE776238A (en) | 1972-04-04 |
| DE2159874A1 (en) | 1973-05-03 |
| AR196867A1 (en) | 1974-02-28 |
| AU3632571A (en) | 1973-06-07 |
| FR2116508A1 (en) | 1972-07-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1151404A (en) | Novel Gona-1,3,5(10)-Trienes, Processes for their Preparation, and Compositions incorporating them | |
| GB1429922A (en) | Steroid acetals processes for their manufacture and preparations containing them | |
| GB1366080A (en) | 6alpha,15alpha-dihydroxy-steroids | |
| ES379001A1 (en) | Stable aqueous steroid phosphate solutions | |
| GB1211220A (en) | 21-aldehydes of the pregnane series and derivatives thereof and process for their manufacture | |
| ES456057A1 (en) | Novel enol esters of steroids, compositions containing such compounds, processes for their preparation and methods of treatment therewith | |
| GB1416839A (en) | 17beta-hydroxy-16,16-dimethylestr-4-en-3-one | |
| GB1161629A (en) | Pregnadienes | |
| GB1259492A (en) | ||
| GB1244560A (en) | Halogenated steroids and process for the manufacture thereof | |
| GB1141214A (en) | New derivatives of proscillaridin a | |
| GB1366329A (en) | Process for the manufacture of delta4-3-oxo-1alpha-methylsteroids | |
| GB1388443A (en) | Selective reduction of 9,15-dioxoprostanoic acids | |
| GB1174360A (en) | 6,16-Dimethyl-21-Fluoro-Steriods of the Pregnane Series. | |
| GB1289918A (en) | ||
| GB1185381A (en) | 05,16beta-Methylene Steroids of the 19-Nor-Androstane Series and Process for their Manufacture | |
| GB1265444A (en) | ||
| GB1289020A (en) | ||
| GB1164705A (en) | Preparation of Delta<7>-Dehydro Steroids | |
| GB1324612A (en) | Epoxy estranes processes for their preparation and compositions incorporating them | |
| GB1263383A (en) | 6-fluoro steroids of the androstane series and their manufacture | |
| GB1263804A (en) | 08-METHYL-2alpha,3alpha-EPITHIO-5alpha-ANDROSTANE DERIVATIVES | |
| GB1348943A (en) | 5alpha-halo-6,6-difluoro-20-ketopregnanes | |
| GB1132061A (en) | 3,17-diketo-steroids | |
| GB1147798A (en) | Steroid 3-thioketals |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |