GB1336434A - 14,18- epoxy-ethanoimino steroids their preparation and compositions containing them - Google Patents

14,18- epoxy-ethanoimino steroids their preparation and compositions containing them

Info

Publication number
GB1336434A
GB1336434A GB5042570A GB5042570A GB1336434A GB 1336434 A GB1336434 A GB 1336434A GB 5042570 A GB5042570 A GB 5042570A GB 5042570 A GB5042570 A GB 5042570A GB 1336434 A GB1336434 A GB 1336434A
Authority
GB
United Kingdom
Prior art keywords
diacetoxy
epoxy
pregnan
methoxy
compounds
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
GB5042570A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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
Priority claimed from CH1590269A external-priority patent/CH575438A5/en
Application filed by JR Geigy AG filed Critical JR Geigy AG
Publication of GB1336434A publication Critical patent/GB1336434A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0036—Nitrogen-containing hetero ring
    • C07J71/0057—Nitrogen and oxygen
    • 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
    • C07J13/005—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 16 (17)
    • 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
    • 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
    • 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
    • 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
    • C07J7/0065—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 an OH group free esterified or etherified
    • C07J7/007—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 an OH group free esterified or etherified not substituted in position 17 alfa
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Farming Of Fish And Shellfish (AREA)
  • Fodder In General (AREA)

Abstract

1336434 14,18-Epoxyethanoimino steroids J R GEIGY AG 23 Oct 1970 [24 Oct 1969 24 July 1970] 50425/70 Heading C2U The invention relates to compounds of formula wherein R 1 is H, C 1-8 alkyl or benzyl; R 2 is H 2 or oxo; R 3 is free or ketalized oxo or is a hydrogen atom with a free, esterified or etherified OH group; R 4 is defined as R 3 or is a free or etherified OH group and, together with R 8 , a 3α,9α-epoxy radical; R 5 and R 6 are each defined as R 3 , or may be H 2 , or, when occurring at a double bond, H; R 7 is H; R 8 is α-H, α-OH or, together with R 4 , 3α,9α-epoxy; and R 9 is H or free, esterified or etherified OH; and wherein double bonds may be present in position 5 or 4 (in the latter only when R 4 is free oxo), and in positions 7, 9(11) and 16 corresponding to the dotted lines and with the elimination of R 7 , R 8 and/or R 9 ; and the acid-addition salts of the above compounds wherein R 2 is H 2 . Compounds (I) and their acid-addition salts are claimed per se with the exception of the following compounds and their acid-addition salts: (a) batrachotoxinin A and its 20-pbromobenzoate, and the derivatives of these compounds and also of batrachotoxin and homobatrachotoxin in which the 3α,9α-epoxy group has been replaced by a 9-hydroxy group; (b) the 20-esters of batrachotoxinin A with 2- or 3- pyrrolecarboxylic acids or their alkylated and/or N-acylated derivatives (including batrachotoxin and homobatrachotoxin); and (c) the specific compounds claimed in Claims 7, 8 and 10-19 of Specification 1,268,568. Compounds (I) (including the compounds excepted from the per se claims) are prepared from compounds of formula (wherein X is halo) by cyclization in the presence of an acid-binding agent, to give compounds (I) wherein R 2 is oxo which may then be reduced with a complex hydride to give compounds (I) wherein R 2 is H 2 which may then be salified. Compounds (I) are further interconvertible by hydrolysis of ether, ester, ketal and epoxy groups; esterification, etherification and oxidation of hydroxy groups; and reduction of oxo to hydroxy. 3# - Methoxy - 3α,9α - epoxy - 11α,20# - diacetoxy - 18 - (N - methyl - 2 - chloroacetamido)- 5#,17α - pregnan - 14# - ol (XIII) is prepared from 3,3 - ethylenedioxy - 20# - hydroxypregna- 5,9(11) - dien - 18 - oic acid (18 -# 20) - lactone (XII) by the sequence: XII -# 3,3- ethylenedioxypregna - 5,9(11) - diene - 18,20#- diol -# 18,20# - dihydroxypregna - 4,9(11)- dien - 3 - one -# 18,20# - dihydroxy - 5# - pregn- 9(11) - en - 3 - one -# 18 - acetoxy - 20#- hydroxy - 5# - pregn - 9(11) - en - 3 - one (+18,20- diacetate as by-product) -# 18 - acetoxy - 5#- pregn - 9(11) - ene - 3,20 - dione -# 3#,11α - dihydroxy - 3α,9α - epoxy - 18 - acetoxy - 5# - preg- nan - 20 - one -# 3# - methoxy - 3α,9α - epoxy- 11α,18 - diacetoxy - 5# - pregnan - 20 - one -# 3# - methoxy - 3α,9α - epoxy - 11α,18 - diacetoxy - 5# - pregn - 16 - en - 20 - one -# 3# - methoxy- 3α,9α - epoxy - 11α,18 - diacetoxy - 5# - pregna- 14,16 - dien - 20 - one -# 3# - methoxy - 3α,9α; 14#,15# - diepoxy - 11α,18 - diacetoxy - 5# - pregn- 16 - en - 20 - one -# 3# - methoxy - 3α,9α - epoxy- 11α,18 - diacetoxy - 14# - hydroxy - 5#,17α - pregnan - 20 - one -# 3# - methoxy - 3α,9α - epoxy- 11α,18,20# - triacetoxy - 5#,17α - pregnan - 14#- ol -# 3# - methoxy - 3α,9α - epoxy - 11α,20- diacetoxy - 5#,17α - pregnane - 14#,18 - diol -# 3# - methoxy - 3α,9α - epoxy - 11α,20# - diacetoxy- 14# - hydroxy - 5#,17α - pregnan - 18 - al -# 3#- methoxy - 3α,9α - epoxy - 11α,20# - diacetoxy - 18- methylimino - 5#,17α - pregnan - 14# - ol -# 3#- methoxy - 3α,9α - epoxy - 11α,20# - diacetoxy - 18- methylamino - 5#,17α - pregnan - 14# - ol -# XIII. (Example 8). 3#,20# - Diacetoxy - 18 - (N - methyl - 2- chloroacetamido) - 5α,17α - pregnan - 14# - ol (XI) is prepared from 3#-acetoxy-5α-pregnan-20#-ol (X) by the sequence: X -# 3#-acetoxy-18,20- epoxy - 5α - pregnan - 20# - ol -# 3#,18 - diacetoxy - 5α - pregnan - 20 - one -# 3#,18 - diacetoxy - 17# - bromo - 5α,17# - pregnan - 20 - one -# 3#,18 - diacetoxy - 5α - pregn - 16 - en - 20- one -# 3#,18 - diacetoxy - 5α - pregna - 14,16- dien - 20 - one -# 3#,18 - diacetoxy - 14#,15#- epoxy - 5α - pregn - 16 - en - 20 - one -# 3#,18- diacetoxy - 14# - hydroxy - 5α,17α - pregnan - 20- one -# 3#,18 - diacetoxy - 5α,17α - pregnane- 14#,20# - diol -# 3#,18,20# - triacetoxy - 5α,17α- pregnan - 14# - ol -# 3#,20# - diacetoxy - 5α,17α- pregnane - 14#,18 - diol -# 3#,20# - diacetoxy- 14# - hydroxy - 5α,17α - pregnan - 18 - al -# 3#,20# - diacetoxy - 18 - methylimino - 5α,17α- pregnan - 14# - ol -# 3#,20# - diacetoxy - 18- methylamino - 5α,17α - pregnan - 14# - ol -# XI. (Example 7). Cardioactive compositions for oral, parenteral and topical administration comprise a carrier and a compound (I) (subject to the above exceptions) or an organic or inorganic acidaddition salt thereof. Reference has been directed by the Comptroller to Specification 1,268,568.
GB5042570A 1969-10-24 1970-10-23 14,18- epoxy-ethanoimino steroids their preparation and compositions containing them Expired GB1336434A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1590269A CH575438A5 (en) 1969-10-24 1969-10-24 Cardiotropic (14-beta-18(epoxy-ethano-imino) - steroids
CH1124270 1970-07-24

Publications (1)

Publication Number Publication Date
GB1336434A true GB1336434A (en) 1973-11-07

Family

ID=25708025

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5042570A Expired GB1336434A (en) 1969-10-24 1970-10-23 14,18- epoxy-ethanoimino steroids their preparation and compositions containing them

Country Status (10)

Country Link
JP (1) JPS495354B1 (en)
AT (1) AT307634B (en)
AU (1) AU2147670A (en)
BE (1) BE757924A (en)
DE (1) DE2052166A1 (en)
FR (1) FR2070158B1 (en)
GB (1) GB1336434A (en)
HU (1) HU163270B (en)
IL (1) IL35512A0 (en)
NL (1) NL7015246A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2325806A1 (en) * 1972-05-30 1973-12-13 Ciba Geigy Ag METHOD OF MANUFACTURING DELTA HIGH 16 -STEROID-14BETA, 18, 20-TRIOLS AND -14BETA, 20-DIOL-18-ALEN OF THE PREGNAN SERIES
DE2325873A1 (en) * 1972-05-30 1973-12-13 Ciba Geigy Ag PROCESS FOR THE PREPARATION OF 14,18EPOXYAETHANOIMINOSTEROIDS

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1768162A1 (en) * 1968-04-06 1971-09-30 Schering Ag New 18-nor-14ss-pregnano- [13,14-f] -hexahydro-1,4-oxazepine

Also Published As

Publication number Publication date
AU2147670A (en) 1972-04-27
IL35512A0 (en) 1970-12-24
JPS495354B1 (en) 1974-02-06
FR2070158A1 (en) 1971-09-10
DE2052166A1 (en) 1971-05-06
BE757924A (en) 1971-04-01
AT307634B (en) 1973-05-25
FR2070158B1 (en) 1974-08-30
HU163270B (en) 1973-07-28
NL7015246A (en) 1971-04-27

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee