GB1307360A - Substituted 17alpha-penta-1,3-diynyl steroids - Google Patents

Substituted 17alpha-penta-1,3-diynyl steroids

Info

Publication number
GB1307360A
GB1307360A GB2522869A GB1307360DA GB1307360A GB 1307360 A GB1307360 A GB 1307360A GB 2522869 A GB2522869 A GB 2522869A GB 1307360D A GB1307360D A GB 1307360DA GB 1307360 A GB1307360 A GB 1307360A
Authority
GB
United Kingdom
Prior art keywords
compound
group
steroid
ethynyl
prepared
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
Application number
GB2522869A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BDH Pharmaceuticals Ltd
Original Assignee
BDH Pharmaceuticals Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BDH Pharmaceuticals Ltd filed Critical BDH Pharmaceuticals Ltd
Publication of GB1307360A publication Critical patent/GB1307360A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1307360 Substituted 17α-penta-1<SP>1</SP>,3<SP>1</SP>-diynyl steroids; ethynyl carbinols BDH PHARMACEUTICALS Ltd 15 May 1970 [16 May 1969] 25228/69 Headings C2C and C2U [Also in Division A5] Novel steroids possessing a 17#-free, esterified or etherified OH group and a 17α-substituent of the structure wherein R<SP>1</SP> is aryl, aralkyl, heteroeyclic, alicyclic, C 2-5 alkenyl or C 1-5 alkyl, and R<SP>2</SP> is selected from the same values as R<SP>1</SP> or can be H, or R<SP>1</SP> and K<SP>2</SP> together with the adjacent carbon atom form an alicyclic ring, are prepared (1) by reacting a compound B<SP>3</SP>-C#CH with a compound R<SP>4</SP>-C#CBr, wherein one of R<SP>3</SP> and R<SP>4</SP> is a steroidal moiety which has a 17#-free, esterified or etherified OH group and to which - C=3H or -C=CBr is linked in the 17α- position and the other is -C(OH).R<SP>1</SP>.R<SP>2</SP>, in the presence of a cuprous salt maintained in the reduced state, e.g. by inclusion of a reducing agent such as hydroxylamine; or (2) for products containing a free 17#-OH group, by reacting a 17-oxo steroid with a compound of the formula M-(CmC) 2 -C(OH).R<SP>1</SP>.R<SP>2</SP> wherein M is Li, Na, K, or MgHal (Hal is Cl, Br or I) and subsequently regenerating the steroid from the resulting complex; or (3) by treating a metal derivative of a 17α-buta-1,3-diynyl-steroid with a compound R<SP>1</SP>.R<SP>2</SP>.CO. In these processes a steroid oxo group may be protected, e.g. as an oxime, and subsequently released, and in (2) the OH group of the acetylenic compound may be protected, e.g. as a tetrahydropyranyl ether. Resulting 17#-ols may be esterified or etherified. 17α - Bromoethynyl - 6# - methyl - 5α- andro- Start.3#,5,17#-trial is prepared from the corresponding 17α-ethynyl compound and N-bromosuccinimide. 3 - Acetoxy - 17α - bromoethynyl- 1 ,3,5( 10)-estratrien- 17#-ol is prepared similarly. Starting materials of the formula are prepared from compounds R<SP>1</SP>R<SP>2</SP>.CO and acetylene derivatives HC#C.M where R<SP>1</SP>, R<SP>2</SP> and M are as defined above. Specified products are ethynyl-p-tolyl-carbinol, ethyl-(2-naphthyl)- carbinol and p-biphenylyl-ethynyl-carbinol. Specification 1,108,758 is referred to.
GB2522869A 1969-05-16 1969-05-16 Substituted 17alpha-penta-1,3-diynyl steroids Expired GB1307360A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2522869 1969-05-16

Publications (1)

Publication Number Publication Date
GB1307360A true GB1307360A (en) 1973-02-21

Family

ID=10224288

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2522869A Expired GB1307360A (en) 1969-05-16 1969-05-16 Substituted 17alpha-penta-1,3-diynyl steroids

Country Status (13)

Country Link
US (1) US3758521A (en)
JP (1) JPS4842069B1 (en)
BE (1) BE750461A (en)
CA (1) CA952899A (en)
DE (1) DE2023917A1 (en)
DK (1) DK129340B (en)
ES (1) ES379730A1 (en)
FR (1) FR2051531B1 (en)
GB (1) GB1307360A (en)
IE (1) IE34171B1 (en)
NL (1) NL7007153A (en)
SE (1) SE374741B (en)
ZA (1) ZA703304B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4115456A (en) * 1975-06-19 1978-09-19 Merck Patent Gesellschaft Mit Beschrankter Haftung Alkyne compounds and method of use

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1427141A (en) * 1972-05-03 1976-03-10 Bdh Pharmaceuticals Ltd 17-alka-1,3-diynyl- steroids
JPS60174049U (en) * 1984-04-18 1985-11-18 和泉電気株式会社 circuit breaker

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB961502A (en) * 1962-02-02 1964-06-24 British Drug Houses Ltd 17ª‡-butadiynyl-17ª‰-hydroxy steroids
GB1108758A (en) * 1966-02-03 1968-04-03 British Drug Houses Ltd Substituted-17ª‡-buta-1',3'-diynyl-steroids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4115456A (en) * 1975-06-19 1978-09-19 Merck Patent Gesellschaft Mit Beschrankter Haftung Alkyne compounds and method of use

Also Published As

Publication number Publication date
FR2051531A1 (en) 1971-04-09
FR2051531B1 (en) 1973-08-10
NL7007153A (en) 1970-11-18
DK129340B (en) 1974-09-30
CA952899A (en) 1974-08-13
BE750461A (en) 1970-11-16
US3758521A (en) 1973-09-11
SE374741B (en) 1975-03-17
JPS4842069B1 (en) 1973-12-10
DE2023917A1 (en) 1970-11-19
DK129340C (en) 1975-02-17
ZA703304B (en) 1971-12-29
IE34171B1 (en) 1975-02-19
ES379730A1 (en) 1973-01-16
IE34171L (en) 1970-11-16

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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