US3524850A - Methylalkanoyloxymethyl ketals of prednisolone derivatives - Google Patents

Methylalkanoyloxymethyl ketals of prednisolone derivatives Download PDF

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Publication number
US3524850A
US3524850A US610010A US3524850DA US3524850A US 3524850 A US3524850 A US 3524850A US 610010 A US610010 A US 610010A US 3524850D A US3524850D A US 3524850DA US 3524850 A US3524850 A US 3524850A
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US
United States
Prior art keywords
ketals
methylalkanoyloxymethyl
oxyacetonide
derivatives
prednisolone derivatives
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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 - Lifetime
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US610010A
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English (en)
Inventor
Bo Thuresson Af Ekenstam
Karl Goran Claeson
Fritz Henn
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.)
Saab Bofors AB
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Bofors AB
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Definitions

  • X is H or F and R is an alyl group having 3 to 5 carbon atoms possess anti-inflammatory action.
  • This invention relates to anti-inflammatory steroids, particularly prednisolone derivatives. It particularly relates to alkylalkanoyloxy alkyl ketals of fiuorinated prednisolone derivatives.
  • alkylalkanoyloxyalkyl ketals of prednisolone derivatives have provide to have good anti-inflammatory effect, particularly when the alkanoyl group contains 1-2 carbon atoms. Tests with other acetals and ketals have shown that the number of carbon atoms in the acetal and ketal group should be low.
  • Known methylalkanoyloxymethyl ketals are described in e.g. the British Pat. No. 1,020,309 and the Belgian Pat. No. 660,549.
  • the compound according to the present invention has the following general formula:
  • R is an alkyl group which has at least 3 carbon atoms and not more than 5 cabon atoms
  • X designates hydrogen or fluorine
  • EXAMPLE 1 To a suspension of 300 mg. of triamcinolon in 7.5 ml. of dioxane (dried and newly distilled), 2.5 g. of caproyloxy-acetone and 25 mg. of perchloric acid are added. The reaction mixture is stirred at 20-30" C. in nitrogen gas atmosphere for 5 hours. Gradually, a homogeneous, acid solution is formed, which is neutralized with a 5% sodium bicarbonate solution to pH 6.5. The solution is extracted with chloroform, after which the chloroform layer is dried and evaporated in vacuum. The reaction is re-crystallized from approx. 10 ml. of a mixture of ethyl acetate and ligroin in the proportion 1:1. Triamcinolone caprolyoxyacetonide is obtained, with a yield of 82% and a melting point of 229-230 C.
  • TAB LE Granulom weight in percent of granulom Daily weight of dose in Number reference No. Corticosteriod mg. of animals animals 1 Triameinolone acetyl- 10 48 69 oxyacetonide. 2 Triameinolone butyroyl- 10 8 67 oxyaeetonide. 3 Triameinolone valeroyl- 10 8 50 oxyacetonide. 4 Triamcinolone caproyl- 10 8 64 oxyacetonide. 5 Triamcinolone-3,3-di- 10 methyl-butyroyloxyacetonide. 6 Fluocinolone valeroyl- 10 8 62 oxyacetonide. 7 Triamcinolone acetyl- 3.
  • valeroyl- 4 A compound of the formula oxyacetonides have a considerably better anti-inflammatory effect compared with the other compounds.
  • a compound of the formula: 5 '-----O 0 0 cnr-o- -cim on 0 0/ cm-o-fi-m References Cited 15 UNITED STATES PATENTS 3,048,581 8/1962 Fried 260-23955 wherein R is an alkyl group containing from 4-5 car- 3,341,526 9/ 1967 Af Ekenstam 260-23955 bon atoms and X is hydrogen or fluorine.
  • R 20 LEWIS GOTTS Pnmary Examiner butyl. E. G. LOVE, Assistant Examiner 3.
  • R is amyl. US. Cl. X.R.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US610010A 1966-01-27 1967-01-18 Methylalkanoyloxymethyl ketals of prednisolone derivatives Expired - Lifetime US3524850A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE1048/66A SE307576B (en, 2012) 1966-01-27 1966-01-27

Publications (1)

Publication Number Publication Date
US3524850A true US3524850A (en) 1970-08-18

Family

ID=20257516

Family Applications (1)

Application Number Title Priority Date Filing Date
US610010A Expired - Lifetime US3524850A (en) 1966-01-27 1967-01-18 Methylalkanoyloxymethyl ketals of prednisolone derivatives

Country Status (11)

Country Link
US (1) US3524850A (en, 2012)
AT (1) AT269385B (en, 2012)
BE (1) BE692983A (en, 2012)
CH (1) CH487872A (en, 2012)
DE (1) DE1618028A1 (en, 2012)
ES (1) ES336470A1 (en, 2012)
FR (1) FR6257M (en, 2012)
GB (1) GB1120337A (en, 2012)
GR (1) GR33327B (en, 2012)
NL (1) NL6700465A (en, 2012)
SE (1) SE307576B (en, 2012)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2278122C1 (ru) * 2004-12-27 2006-06-20 Институт Молекулярной Генетики Российской Академии Наук (Имг Ран) Высокомеченный тритием [3h]-ацетонид 9альфа-фторо-16альфа-гидроксипреднизолона
JP2013504524A (ja) 2009-09-11 2013-02-07 シエシー ファルマセウティチィ ソシエタ ペル アチオニ イソオキサゾリジン誘導体

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3048581A (en) * 1960-04-25 1962-08-07 Olin Mathieson Acetals and ketals of 16, 17-dihydroxy steroids
US3341526A (en) * 1965-01-12 1967-09-12 Bofors Ab Acyloxyacetals of fluoro-16alpha-hydroxyprednisolones

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3048581A (en) * 1960-04-25 1962-08-07 Olin Mathieson Acetals and ketals of 16, 17-dihydroxy steroids
US3341526A (en) * 1965-01-12 1967-09-12 Bofors Ab Acyloxyacetals of fluoro-16alpha-hydroxyprednisolones

Also Published As

Publication number Publication date
CH487872A (de) 1970-03-31
SE307576B (en, 2012) 1969-01-13
DE1618028A1 (de) 1970-10-29
GR33327B (el) 1967-11-23
NL6700465A (en, 2012) 1967-07-28
GB1120337A (en) 1968-07-17
AT269385B (de) 1969-03-10
FR6257M (en, 2012) 1968-08-19
ES336470A1 (es) 1970-04-01
BE692983A (en, 2012) 1967-07-03

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