IL41506A - 15alpha,16alpha-methylene-delta4-oestren-17beta-ols - Google Patents
15alpha,16alpha-methylene-delta4-oestren-17beta-olsInfo
- Publication number
- IL41506A IL41506A IL41506A IL4150673A IL41506A IL 41506 A IL41506 A IL 41506A IL 41506 A IL41506 A IL 41506A IL 4150673 A IL4150673 A IL 4150673A IL 41506 A IL41506 A IL 41506A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- group
- ene
- methylene
- hydroxy
- Prior art date
Links
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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1425636 15,16 - Methylene - estr - 4 - enes SCHERING AG 12 Feb 1973 [11 Feb 1972] 6821/73 Heading C2U [Also in Division A5] Novel steroids of the formula wherein R<SP>1</SP> is C 1-5 alkyl; R<SP>2</SP> is H or acyl; R<SP>3</SP> is H or an optionally substituted aliphatic hydrocarbon group of at most 5 carbon atoms (exclusive of substituents); and X is O or H (OR<SP>4</SP>) in which OR<SP>4</SP> is in the alpha or beta position and R<SP>4</SP> is H or acyl are prepared from steroids of the formulµ wherein Y is a protected keto group and the dotted lines in the rings indicate the presence of a #<SP>5</SP>- or #<SP>5(10)</SP>-double bond and when a #<SP>5(10)</SP>- double bond is present then the 10-H atom is absent, by reduction in the 17-position or conversion to a 17α-substituted-17#-ol followed when required, by hydrolysis to a free #<SP>4</SP>-3-one and, if desired, by hydrogenation of a 17α- unsaturated group and/or reduction to a 3-ol and/or acylation of a free OH group. 3,3 - (2<SP>1</SP>,2<SP>1</SP> - Dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy)- 18 - methyl - 15α,16α - methylene - #<SP>5</SP> or #<SP>5(10)</SP>- estren-17-one is prepared from 3,3-(2<SP>1</SP>,2<SP>1</SP>-dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 18 - methyl - 19- nor - #<SP>5,16</SP> or <SP>15(10),16</SP> - pregnadien - 20 - one (prepared from the #<SP>4</SP>-3-one and 2,2-dimethyl-1,3- propane-diol) by oxygenation to give the corresponding #<SP>15</SP> - 17α - ol, reduction of this to the corresponding 20-ol, reaction of this with methylene iodide in the presence of a Zn-Cu couple to give 17α,20# - dihydroxy - 3,3 - (2<SP>1</SP>,2<SP>1</SP>- dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 18 - methyl- 15α,16α - methylene - 19 - nor - #<SP>5</SP>- or #<SP>5(10)</SP>- pregnene and oxidation of this. 3,3-(2<SP>1</SP>,2<SP>1</SP> -dimethyl - 1<SP>1</SP>,3<SP>1</SP> - propylenedioxy) - 15α,16α- methylene - #<SP>5</SP> or <SP>15(10)</SP> - estren - 17 - one is prepared similarly via corresponding intermediates. The novel steroids are stated to possess a strong androgenic and anabolic activity or a strong gestagenic activity and they may be made up into pharmaceutical compositions with suitable carriers. The gestagenic compounds can be used, possibly together with estrogens, in contraceptive preparations (see Heading A5B).
[GB1425636A]
Claims (50)
1. A compound of tthe general formula I 1n which R represents a methyl or ethyl group, R represents a hydrogen atom 3 or an alkanoyl group, R represents a hydrogen atom or an ethyl, vinyl, ethynyl, chloroethynyl, or butadlenyi group and X represents an oxygen atom or a grouping 4 of the formula H, OR^ wherein the OR^ group 1s 1n the β-position and in which R represents a hydrogen atom or an alkanoyl group.
2. A compound as claimed in claim 1 wherein ^ represents a methyl or ethyl group 3
3. A compound as claimed 1n claim 1 .wherein R represents an ethynyl group. 3
4. A compound as claimed 1n claim 1 or 2, wherein R represents a methyl, ethyl, butyl, vinyl, ethynyl or butadlynyl group. 3
5. A compound as claimed 1n claim 1 or 2, wherein R represents a chlorethynyl group. 4
6. 17g-Hydroxy-18-methyl-15a,16a-methylene-A -oestren-3-one. 4
7. 17s-Hydroxy-15a,16a-methylene-A -oestren-3-one. 4
8. 173-Hydroxy-18-methyl-17a-ethynyl-15a,16a-methylene-A -oestren-3-one. 4
9. 173-Hydroxy-17a-ethynyl-15a,16a-methylene-A -oestren-3-one. 4
10. 173-Acetoxy-18-methyl-15a,16a-methylene-A -oestren-3-one. 4
11. 173-Acetoxy-15a,16a-methylene -Δ -oestren-3-one.
12. 173-Acetoxy-18-methyl -17a-ethynyl -15a, 16o-methy 1 ene-Δ -oestren-3-one,
13. 178-Butyroxy-l 8-methyl -17a-ethynyl -15a ,16a-methyl ene-Δ4-oestren-3-one.
14. 170-Heptanoy 1 oxy-18-methyl -17a-ethy ny 1 -15a , 16a-methy 1 ene-Δ -oestren-3-one.
15. 173-Acetoxy-l 7a-ethyr yl -15a ,16a-methy 1 ene-A4-oes tren-3-one . 4
16. 173-Bu ty roxy-1 ¾ -ethyny 1 -15a , 16a-methy 1 ene-Δ -oes tren-3-one .
17. 173-Heptanoyl xoy-17a-ethynyl -15a , 16a-methy 1 ene-A^-oes tren-3-one .
18. 3p , 173-D1 hydroxy- 18-methyl -17a-ethy ny 1 -15a , 16a-meth 1 ene-Δ4-oestrene. 4
19. 33,l73-D1hydroxy-l7a-ethyny1-l5a,l6a-methylene-A -oestrene.
20. 173-Hydroxy-33-acetoxy-18-methyl -17a-ethynyl-15a,16a- 4 methyl ene-Δ -oestrene.
21. . 173-Hydroxy-33-acetoxy-17a-ethynyl-15a,16a-methylene-A4-oestrene. 4
22. 30,173-D1 acetoxy- 18-methyl - 17a-ethy 1 -15a , 16a-methy 1 ene-Δ -oestrene i
23. 3 , 173-D1 acetoxy-17a-ethynyl -15a, 16a-methyl ene-A^-oestrene .
24. 2 . 33-Hydroxy-l 73-acetoxy-l 8-methyl -17a-ethyr yl -15a ,16a-methy 1 ene- Λ Δ -oestrene. 4
25. 33-Hydroxy-l 73-acetoxy-l 7a-ethynyl -15a , 16a-methyl ene-Δ -oestrene .
26. 173-Hydroxy- 18-methyl - 17a-eth 1 - 15a , 16a-me thy 1 ene-A4-oes trene-3-one. 4
27. 173-Hydroxy- 18-methyl - 17a-ch 1 orethy ny 1 - 15a , 16a-methy 1 ene-Δ -oestren-3-one. 4
28. 173-Dodecanoyl oxy-18-methyl -15 , 16a-methy 1 ene-Δ -oes tren-3-one .
29. 173-Hydroxy-33-heptanoy 1 oxy-18-methyl - 17a-ethy ny 1 - 15a , 16a- 4 methyl ene-Δ -oestrene.
30. 173-Acetoxy-33-octanoy 1 oxy-18-methyl -1 a-ethynyl -15a ,16a-methyl ene-Δ 4 -oestrene. ■ · ,- 4
31. . l7B-Hydroxy-l8-methyl-l7a-butad1ynyl-l5a ,l6a-methylene-A -oestren-4rone. Λ
32. 176-Hydroxy-l 8-methy 1 - 17a- vi nyl - 15a , 16armethy 1 ene-Δ -oes tren-3-one .
33. A pharmaceutical preparation which compBlses a compound as claimed In any one of claims 1 to 5 , 1n admixture or conjunction with a pharmaceutical ly suitable carfier,
34. ; A pharmaceutical preparation which comprises the compound claimed In any one of claims 6 to 32, In admixture or conjunction with a pharmaceutically suitable carrier,
35. A preparation as claimed 1n cl aim 33 or 34, which 1s 1n the form of a contraceptive preparation.
36. A preparation as claimed 1n claim 35, which also contains an oestrogenically active compound.
37. A preparation as claimed 1n any one of claims 33 to 36 , which 1s 1 n a form suitable for oral administration.
38. A preparation as claimed 1n claim 37 , which is in the form of a tablet, dragee , capsule , pi l l , suspension or solution.
39. A preparation as claimed 1n any ,c|¾j) of claims 33 to 36 , which is in a form suitable for. parenteral administration.
40. » A preparation as claimed in claim 39 , which is I n the form of an plly solution.
41. A preparation having a composition substantially as described in any one of Examples 37 to 47 herein.
42. A method of contraception, wherei n there 1s administered in a contraceptive dose to a female maipal , as hereinbefore defined , a compound as claimed In any one of claims 1 to 5,
43. A method of contraception , wherein there 1s administered 1 n a contraceptive dose to a female mammal , as hereinbefore defined , the compound claimed 1n any one of claims 6 to 32.
44. A method as claimed in claim 42 or 43, wherein the female mammal is a female of the human species . , 41506/3
45. A system which comprises a compound as claimed 1n any one of claims 1 to 5 together with instructions, which Instructions require the administration of the compound 1n a contraceptive dose to a female mamma 1 , as hereinbefore defined.
46. A system which comprises the compound claimed 1n any one of claims 6 to 32 together with Instructions, which instructions require the administration of the compound 1n a contraceptive dose to a female mammal, as hereinbefore defined.
47. A system as claimed in claim 45 or 46, wherein the female mammal is a female of the human species.
48. A process for the manufacture of a compound of the general formula I in which R represents a methyl or ethyl group, R represents a hydrogen atom . 3 or an alkanoyl group, R represents a hydrogen atom or an ethyl, vinyl, ethynyl, chloroethynyl, or butadlenyl group and X represents an oxygen atom or a grouping of the formula H.OR^ wherein the O ^ group 1s 1n the β -position and 1n which R^ represents a hydrogen atom or an alkanoyl group, wherein the 17-fteto group in a 15a ,16a-methylene-17-oxo-A5^- or A5^°^-oestrene of the general formula II 1n which R has the meaning given above and Y represents a free or protected keto group 1s reduced to form an ~ .R3 grouping 1n which R3 has the meaning given above, any Uorunsaturated group 1s, if desired, hydrogenated, and any protected keto group 1n the 3-pos1t1on 1s converted Into a free keto group, and then, if desired, the 3-keto group is reduced to form a hydroxy1 group together with a hydrogen atom and/or, 1f desired, alkenoyloxy a free hydroxy! group is converted into an aeytexy group.
49. A process as claimed in claim 48, wherein the protected keto group Is a ketaHzed keto group,
50. Any one of the processes as claimed in claim 48, conducted substantially as described in the Examples herein. For the Applicants Wolff, Bregman and Goller
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2207421A DE2207421C3 (en) | 1972-02-11 | 1972-02-11 | 15?, 16? -Methylene-4-oestrene-17? -ols or acylates, processes for their production and medicaments containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41506A0 IL41506A0 (en) | 1973-04-30 |
| IL41506A true IL41506A (en) | 1976-07-30 |
Family
ID=5836211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41506A IL41506A (en) | 1972-02-11 | 1973-02-09 | 15alpha,16alpha-methylene-delta4-oestren-17beta-ols |
Country Status (29)
| Country | Link |
|---|---|
| JP (1) | JPS5829317B2 (en) |
| KR (1) | KR780000156B1 (en) |
| AT (1) | AT327413B (en) |
| AU (1) | AU467306B2 (en) |
| BE (1) | BE795241A (en) |
| CA (1) | CA997753A (en) |
| CH (2) | CH590883A5 (en) |
| CS (1) | CS193019B2 (en) |
| DD (1) | DD102379A5 (en) |
| DE (1) | DE2207421C3 (en) |
| DK (1) | DK131037B (en) |
| EG (1) | EG10914A (en) |
| ES (1) | ES410933A1 (en) |
| FI (1) | FI52225C (en) |
| FR (1) | FR2181719B1 (en) |
| GB (1) | GB1425636A (en) |
| GR (1) | GR63160B (en) |
| HU (1) | HU165253B (en) |
| IE (1) | IE37266B1 (en) |
| IL (1) | IL41506A (en) |
| NL (1) | NL177217C (en) |
| NO (2) | NO140304C (en) |
| PH (1) | PH9370A (en) |
| PL (1) | PL81084B1 (en) |
| RO (1) | RO73527A (en) |
| SE (3) | SE403781B (en) |
| SU (1) | SU513628A3 (en) |
| YU (1) | YU35035B (en) |
| ZA (1) | ZA73944B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007027636A1 (en) | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17β-Cyano-18α-homo-19-nor-androst-4-ene derivative, its use and the derivative-containing drug |
| DE102007027637A1 (en) | 2007-06-12 | 2008-12-18 | Bayer Schering Pharma Aktiengesellschaft | 17β-cyano-19-nor-androst-4-ene derivative, its use and the derivative-containing drug |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT274653B (en) * | 1966-11-10 | 1969-09-25 | Alexander Schoeller & Co Kg | Stackable, rectangular, closed plastic transport container for fine-grained bulk goods and liquids |
-
0
- BE BE795241D patent/BE795241A/en not_active IP Right Cessation
-
1972
- 1972-02-11 DE DE2207421A patent/DE2207421C3/en not_active Expired
- 1972-12-29 PL PL1972159970A patent/PL81084B1/pl unknown
-
1973
- 1973-01-11 DD DD168198A patent/DD102379A5/xx unknown
- 1973-01-16 DK DK24273AA patent/DK131037B/en not_active IP Right Cessation
- 1973-01-23 FI FI730169A patent/FI52225C/en active
- 1973-01-24 ES ES410933A patent/ES410933A1/en not_active Expired
- 1973-01-31 CS CS73748A patent/CS193019B2/en unknown
- 1973-01-31 YU YU243/73A patent/YU35035B/en unknown
- 1973-02-06 IE IE190/73A patent/IE37266B1/en unknown
- 1973-02-06 CA CA163,029A patent/CA997753A/en not_active Expired
- 1973-02-07 EG EG49/73A patent/EG10914A/en active
- 1973-02-08 AT AT112473A patent/AT327413B/en not_active IP Right Cessation
- 1973-02-09 ZA ZA730944A patent/ZA73944B/en unknown
- 1973-02-09 SU SU1891803A patent/SU513628A3/en active
- 1973-02-09 NO NO528/73A patent/NO140304C/en unknown
- 1973-02-09 FR FR7304678A patent/FR2181719B1/fr not_active Expired
- 1973-02-09 GR GR1318A patent/GR63160B/en unknown
- 1973-02-09 PH PH14330*UA patent/PH9370A/en unknown
- 1973-02-09 CH CH186373A patent/CH590883A5/xx not_active IP Right Cessation
- 1973-02-09 CH CH535776A patent/CH593995A5/xx not_active IP Right Cessation
- 1973-02-09 IL IL41506A patent/IL41506A/en unknown
- 1973-02-10 KR KR7300246A patent/KR780000156B1/en active
- 1973-02-10 HU HUSE1666A patent/HU165253B/hu unknown
- 1973-02-10 RO RO7373805A patent/RO73527A/en unknown
- 1973-02-12 SE SE7301935A patent/SE403781B/en unknown
- 1973-02-12 NL NLAANVRAGE7301974,A patent/NL177217C/en not_active IP Right Cessation
- 1973-02-12 GB GB682173A patent/GB1425636A/en not_active Expired
- 1973-02-12 JP JP48017357A patent/JPS5829317B2/en not_active Expired
- 1973-02-12 AU AU52076/73A patent/AU467306B2/en not_active Expired
-
1975
- 1975-12-22 SE SE7514513A patent/SE409329B/en not_active IP Right Cessation
-
1977
- 1977-12-07 SE SE7713896A patent/SE426834B/en not_active IP Right Cessation
-
1978
- 1978-08-14 NO NO782754A patent/NO143065C/en unknown
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