GB1520356A - 11-12-unsaturated-9-fluoro-steroids and a process for the-eir manufacture - Google Patents

11-12-unsaturated-9-fluoro-steroids and a process for the-eir manufacture

Info

Publication number
GB1520356A
GB1520356A GB30616/76A GB3061676A GB1520356A GB 1520356 A GB1520356 A GB 1520356A GB 30616/76 A GB30616/76 A GB 30616/76A GB 3061676 A GB3061676 A GB 3061676A GB 1520356 A GB1520356 A GB 1520356A
Authority
GB
United Kingdom
Prior art keywords
unsaturated
alpha
compounds
novel
fluoro
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
GB30616/76A
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
Ciba 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
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1520356A publication Critical patent/GB1520356A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07J5/0046—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 substituted in position 17 alfa
    • C07J5/0061—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 substituted in position 17 alfa substituted in position 16
    • C07J5/0069—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C07J5/0076—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
    • 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
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
    • 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
    • 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
    • C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
    • C07J7/009—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by only one oxygen atom doubly bound
    • 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
    • C07J71/0026—Oxygen-containing hetero ring cyclic ketals
    • C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

Novel 11,12-unsaturated 9 alpha -fluorosteroids, especially those of the androstane and pregnane series, with the following constitution in rings B and C <IMAGE> it being possible for all the substituents customary in the known pharmacological active steroids to be present in the remaining positions in the steroid framework and in the side chain, are prepared. Compounds of this type generally display pharmacological effects analogous to those of the corresponding known compounds; for example the derivatives derived from the known corticosteroids display a potent antiinflammatory effect with a relative reduction in the unwanted effect on the adrenals, thymus and body weight. The novel compounds are obtained by a novel type of chemical process, namely from corresponding 9 alpha -fluoro-11 beta -hydroxysteroids by dehydration using an N,N-disubstituted aminosulphur trifluoride. This process is generally applicable to the preparation of any desired 11,12-unsaturated 9 alpha -fluorosteroids.
GB30616/76A 1975-07-23 1976-07-22 11-12-unsaturated-9-fluoro-steroids and a process for the-eir manufacture Expired GB1520356A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH962075A CH611631A5 (en) 1975-07-23 1975-07-23 Process for the preparation of 11,12-unsaturated 9alpha-fluorosteroids

Publications (1)

Publication Number Publication Date
GB1520356A true GB1520356A (en) 1978-08-09

Family

ID=4353884

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30616/76A Expired GB1520356A (en) 1975-07-23 1976-07-22 11-12-unsaturated-9-fluoro-steroids and a process for the-eir manufacture

Country Status (15)

Country Link
JP (1) JPS5214761A (en)
AT (1) AT353989B (en)
AU (1) AU505846B2 (en)
BE (1) BE844378A (en)
CH (1) CH611631A5 (en)
DE (1) DE2632550A1 (en)
DK (1) DK329976A (en)
ES (1) ES449989A1 (en)
FR (1) FR2318644A1 (en)
GB (1) GB1520356A (en)
IE (1) IE43926B1 (en)
NL (1) NL7608141A (en)
NZ (1) NZ181538A (en)
SE (1) SE7608369L (en)
ZA (1) ZA764405B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4358445A (en) 1979-11-16 1982-11-09 Macdonald Peter 6α-Fluoro-prednisdone 17,21 diesters

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5423643A (en) * 1977-07-22 1979-02-22 Aikawa Tekko Doctor blade stablizing apparatus
FI911202A (en) * 1990-12-28 1992-06-29 Albany Int Corp SCHABERBLAD.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4358445A (en) 1979-11-16 1982-11-09 Macdonald Peter 6α-Fluoro-prednisdone 17,21 diesters

Also Published As

Publication number Publication date
JPS5214761A (en) 1977-02-03
IE43926B1 (en) 1981-07-01
NZ181538A (en) 1978-09-20
FR2318644A1 (en) 1977-02-18
SE7608369L (en) 1977-01-24
CH611631A5 (en) 1979-06-15
FR2318644B1 (en) 1978-12-15
BE844378A (en) 1977-01-24
ZA764405B (en) 1977-08-31
IE43926L (en) 1977-01-23
ES449989A1 (en) 1977-12-01
AT353989B (en) 1979-12-10
DE2632550A1 (en) 1977-02-10
AU1612176A (en) 1978-01-26
ATA539376A (en) 1979-05-15
NL7608141A (en) 1977-01-25
DK329976A (en) 1977-01-24
AU505846B2 (en) 1979-12-06

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee