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GB1095665A - Novel 9ª‰, 10ª‡-steroids and a process for the manufacture thereof - Google Patents

Novel 9ª‰, 10ª‡-steroids and a process for the manufacture thereof

Info

Publication number
GB1095665A
GB1095665A GB3054865A GB3054865A GB1095665A GB 1095665 A GB1095665 A GB 1095665A GB 3054865 A GB3054865 A GB 3054865A GB 3054865 A GB3054865 A GB 3054865A GB 1095665 A GB1095665 A GB 1095665A
Authority
GB
United Kingdom
Prior art keywords
keto
hydroxy
compounds
acyloxy
dihalo
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
GB3054865A
Inventor
Engbert Harmen Reerink Frederi
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 to BE667072D priority Critical patent/BE667072A/xx
Priority to FR25070A priority patent/FR1450840A/en
Priority to FR25071A priority patent/FR4759M/fr
Priority to GB3275567A priority patent/GB1095666A/en
Priority to GB3275967A priority patent/GB1095670A/en
Priority to GB3275667A priority patent/GB1095667A/en
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Priority to GB3275867A priority patent/GB1095669A/en
Priority to GB3275765A priority patent/GB1095668A/en
Priority to GB3054865A priority patent/GB1095665A/en
Priority to GB30546/65A priority patent/GB1078499A/en
Publication of GB1095665A publication Critical patent/GB1095665A/en
Expired legal-status Critical Current

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
    • A61K31/57—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
    • A61K31/573—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 substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • 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
    • 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
    • A61K31/5685—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 having an oxo group in position 17, e.g. androsterone
    • 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
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
    • C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
    • C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Hydrology & Water Resources (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Steroid Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

The invention comprises 3-keto-D 4-, 3-keto-D 4,6-, 3-keto-D 1,4-, 3-keto-D 1,4,6- and 3-acyloxy-D 3,5-derivatives of compounds of formula <FORM:1095665/C2/1> wherein R is a halogen atom, -OR1 is a free, etherified or acylated hydroxy group, X is a hydrogen or halogen atom or a hydroxy or acyloxy group, Y is a hydrogen atom or a free, etherified or acylated hydroxy group and Z is an alkyl, alkenyl or alkynyl group containing up to 5 carbon atoms, and their preparation by (a) reaction of an unsubstituted steroid with an oxalic acid or formic acid ester to obtain a 2 - (carboxy - hydroxy - methylene) or 2 - hydroxy-methylene-compound and reacting this successively with a halogenating agent and a base, (b) direct halogenation, including treatment of 3 - keto - D 1,4,6, 3 - acyloxy - D 2,4,6 and 6-halo-compounds, followed where necessary by partial dehalogenation of a 1,2-dihalo, 2,2-dihalo or 6-halo product, (c) introduction of double bonds into the 1- and/or 6-positions by standard methods, (d) enol etherification (e) interconversion of 17b -hydroxy and 17-keto groups, or (f) ethynylation of a 17-keto-compound. The compounds of the invention have uterotrophic, antigonadotrophic or anti-andro-genic activity and may be used in pharmaceutical compositions in combination with a carrier, for example in forms suitable for oral or parenteral administration.
GB3054865A 1965-07-19 1965-07-19 Novel 9ª‰, 10ª‡-steroids and a process for the manufacture thereof Expired GB1095665A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BE667072D BE667072A (en) 1965-07-19
FR25071A FR4759M (en) 1965-07-19 1965-07-19
GB3275567A GB1095666A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10ª‡-steroid derivative
GB3275967A GB1095670A (en) 1965-07-19 1965-07-19 A novel 9ª‰,10ª‡-steroid
GB3275667A GB1095667A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10-ª‡steroid
FR25070A FR1450840A (en) 1965-07-19 1965-07-19 Process for the preparation of new 9beta, 10alpha-steroids
GB3275867A GB1095669A (en) 1965-07-19 1965-07-19 Novel 9ª‰,10ª‡-steroids
GB3275765A GB1095668A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10ª‡-steroid derivative
GB3054865A GB1095665A (en) 1965-07-19 1965-07-19 Novel 9ª‰, 10ª‡-steroids and a process for the manufacture thereof
GB30546/65A GB1078499A (en) 1965-07-19 1965-07-19 Novel 10ª‡-methyl-9ª‰-steroids and a process for the manufacture thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3054865A GB1095665A (en) 1965-07-19 1965-07-19 Novel 9ª‰, 10ª‡-steroids and a process for the manufacture thereof

Publications (1)

Publication Number Publication Date
GB1095665A true GB1095665A (en) 1967-12-20

Family

ID=10309369

Family Applications (7)

Application Number Title Priority Date Filing Date
GB3275765A Expired GB1095668A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10ª‡-steroid derivative
GB3275667A Expired GB1095667A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10-ª‡steroid
GB30546/65A Expired GB1078499A (en) 1965-07-19 1965-07-19 Novel 10ª‡-methyl-9ª‰-steroids and a process for the manufacture thereof
GB3054865A Expired GB1095665A (en) 1965-07-19 1965-07-19 Novel 9ª‰, 10ª‡-steroids and a process for the manufacture thereof
GB3275967A Expired GB1095670A (en) 1965-07-19 1965-07-19 A novel 9ª‰,10ª‡-steroid
GB3275867A Expired GB1095669A (en) 1965-07-19 1965-07-19 Novel 9ª‰,10ª‡-steroids
GB3275567A Expired GB1095666A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10ª‡-steroid derivative

Family Applications Before (3)

Application Number Title Priority Date Filing Date
GB3275765A Expired GB1095668A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10ª‡-steroid derivative
GB3275667A Expired GB1095667A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10-ª‡steroid
GB30546/65A Expired GB1078499A (en) 1965-07-19 1965-07-19 Novel 10ª‡-methyl-9ª‰-steroids and a process for the manufacture thereof

Family Applications After (3)

Application Number Title Priority Date Filing Date
GB3275967A Expired GB1095670A (en) 1965-07-19 1965-07-19 A novel 9ª‰,10ª‡-steroid
GB3275867A Expired GB1095669A (en) 1965-07-19 1965-07-19 Novel 9ª‰,10ª‡-steroids
GB3275567A Expired GB1095666A (en) 1965-07-19 1965-07-19 A novel 9ª‰, 10ª‡-steroid derivative

Country Status (3)

Country Link
BE (1) BE667072A (en)
FR (1) FR4759M (en)
GB (7) GB1095668A (en)

Also Published As

Publication number Publication date
GB1095667A (en) 1967-12-20
GB1078499A (en) 1967-08-09
FR4759M (en) 1967-01-16
GB1095670A (en) 1967-12-20
BE667072A (en)
GB1095668A (en) 1967-12-20
GB1095669A (en) 1967-12-20
GB1095666A (en) 1967-12-20

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