GB1310612A - 17alpha-3-substituted propynyl steroids - Google Patents
17alpha-3-substituted propynyl steroidsInfo
- Publication number
- GB1310612A GB1310612A GB4115872A GB4115870A GB1310612A GB 1310612 A GB1310612 A GB 1310612A GB 4115872 A GB4115872 A GB 4115872A GB 4115870 A GB4115870 A GB 4115870A GB 1310612 A GB1310612 A GB 1310612A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acyl
- steroids
- alkyl
- products
- tetrahydropyran
- 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
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
- A61K31/568—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 positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—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 positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
-
- 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
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
Abstract
1310612 17α - (3 - Hydroxypropynyl) steroids and derivatives SYNTEX CORP 14 April 1970 [18 April 1969 17 Nov 1969] 41158/72 Divided out of 1310611 Heading C2U Novel steroids of the formulae (wherein R is tetrahydrofuran-2-yloxy, tetrahydropyran - 2 - yloxy, 4 - methoxytetrahydropyran - 4 - yloxy, halo, optionally substituted alkylsulphonyloxy or arylsulphonyloxy or hydroxy; R<SP>1</SP> is H or C 1-3 alkyl; R<SP>2</SP> is H or acyl or OR<SP>2</SP> is etherified hydroxy as defined for R; R<SP>3</SP> is O or α-H(#-OR<SP>6</SP>) in which R<SP>6</SP> is H or acyl or OR<SP>6</SP> is etherified hydroxy as defined for R; R<SP>4</SP> is H or CH 3 ; and R is H, C 1-8 alkyl, cycloalkyl, tetrahydrofuran-2-yl, tetrahydropyran-2- yl, 4 - methoxy - tetrahydropyran - 4 - yl or acyl, with the proviso that, in the estratrienes, when R<SP>1</SP> is H, R<SP>2</SP> is H or C 1-10 acyl of M.W. below 200, and R<SP>5</SP> is H, C 1-8 alkyl, cycloalkyl of 5 or 6 ring members, or C 1-10 carboxylic acyl of M.W. below 200, then R is not OH) and the ketals of the 3-keto steroids are prepared (i) when R is etherified OH, by treating the corresponding 17-oxo steroid with the Grignard reagent prepared from appropriate propargyl ethers and ethyl magnesium bromide; (ii) when R is OH, by hydrolysis of the products of (i), or by reacting the corresponding 17α-ethynyl steroids (in which R<SP>2</SP> is preferably an etherifying group) as their Li salts with paraformaldehyde; (iii) when R is halo, by halogenation of the products of (ii) with SOCl 2 , SOBr 2 , PCl 5 , PBr 5 or hydrocarbon sulphonyl fluorides; or (iv) when R is alkyl- or aryl-sulphonyloxy, by esterification of the products of (ii). The products may be subjected to standard etherifications, esterifications, hydrolyses and reductions. All these processes and the preparation of starting materials therefor are described in detail in examples in Specification 1,310,611 from which the present Specification is divided.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81756369A | 1969-04-18 | 1969-04-18 | |
| US87752169A | 1969-11-17 | 1969-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1310612A true GB1310612A (en) | 1973-03-21 |
Family
ID=27124181
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1767570A Expired GB1310611A (en) | 1969-04-18 | 1970-04-14 | Propadienyl steroids and method for their production |
| GB4115872A Expired GB1310612A (en) | 1969-04-18 | 1970-04-14 | 17alpha-3-substituted propynyl steroids |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1767570A Expired GB1310611A (en) | 1969-04-18 | 1970-04-14 | Propadienyl steroids and method for their production |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS4916857B1 (en) |
| AT (1) | AT322120B (en) |
| BE (1) | BE749067A (en) |
| CA (1) | CA919167A (en) |
| CH (1) | CH540894A (en) |
| DE (1) | DE2018055B2 (en) |
| DK (1) | DK133813C (en) |
| ES (1) | ES378764A1 (en) |
| FI (1) | FI47985C (en) |
| FR (1) | FR2051496B1 (en) |
| GB (2) | GB1310611A (en) |
| IL (2) | IL34228A (en) |
| NL (1) | NL7005604A (en) |
| NO (1) | NO134553C (en) |
| SE (1) | SE355802B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1348186A (en) * | 1970-04-24 | 1974-03-13 | Sandoz Ltd | 17alpha-propadienyl steroids |
| CH571537A5 (en) * | 1970-04-24 | 1976-01-15 | Sandoz Ag |
-
1970
- 1970-04-02 IL IL34228A patent/IL34228A/en unknown
- 1970-04-06 CA CA079239A patent/CA919167A/en not_active Expired
- 1970-04-13 FI FI701016A patent/FI47985C/en active
- 1970-04-14 GB GB1767570A patent/GB1310611A/en not_active Expired
- 1970-04-14 GB GB4115872A patent/GB1310612A/en not_active Expired
- 1970-04-15 DE DE19702018055 patent/DE2018055B2/en active Pending
- 1970-04-15 CH CH560270A patent/CH540894A/en not_active IP Right Cessation
- 1970-04-15 AT AT342970A patent/AT322120B/en not_active IP Right Cessation
- 1970-04-16 BE BE749067D patent/BE749067A/en unknown
- 1970-04-17 NO NO1467/70A patent/NO134553C/no unknown
- 1970-04-17 SE SE05322/70A patent/SE355802B/xx unknown
- 1970-04-17 ES ES378764A patent/ES378764A1/en not_active Expired
- 1970-04-17 JP JP45032883A patent/JPS4916857B1/ja active Pending
- 1970-04-17 FR FR707014098A patent/FR2051496B1/fr not_active Expired
- 1970-04-17 DK DK195170A patent/DK133813C/en active
- 1970-04-17 NL NL7005604A patent/NL7005604A/xx unknown
-
1974
- 1974-01-29 IL IL44105A patent/IL44105A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO134553C (en) | 1976-11-03 |
| JPS4916857B1 (en) | 1974-04-25 |
| CH540894A (en) | 1973-08-31 |
| NO134553B (en) | 1976-07-26 |
| FR2051496B1 (en) | 1973-03-16 |
| ES378764A1 (en) | 1973-02-01 |
| GB1310611A (en) | 1973-03-21 |
| FI47985B (en) | 1974-01-31 |
| IL44105A0 (en) | 1974-05-16 |
| DK133813C (en) | 1976-12-13 |
| IL34228A (en) | 1975-04-25 |
| AT322120B (en) | 1975-05-12 |
| SE355802B (en) | 1973-05-07 |
| DK133813B (en) | 1976-07-26 |
| IL34228A0 (en) | 1970-06-17 |
| DE2018055A1 (en) | 1970-10-22 |
| DE2018055B2 (en) | 1976-12-23 |
| CA919167A (en) | 1973-01-16 |
| NL7005604A (en) | 1970-10-20 |
| BE749067A (en) | 1970-10-01 |
| FR2051496A1 (en) | 1971-04-09 |
| FI47985C (en) | 1974-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |