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US4390548A Expired / Lapsed US ⏱️ 0.0 years remaining

Trans-Δ2 -pge alkylsulphonyl amides

Assignee: Ono Pharmaceutical Co Ltd
•
Filing: 1981-04-24
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Granted: 1983-06-28
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Expires: 2001-04-24
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Abstract

Abstract Prostaglandin analogues of the formula: ##STR1## (wherein R 1 represents an alkyl group containing from 1 to 4 carbon atoms, R 2 represents a single bond or an alkylene group containing from 1 to 5 carbon atoms, R 3 represents a hydrogen atom, an alkyl or alkoxy group containing from 1 to 8 carbon atoms, a cycloalkyl or cycloalkyloxy group containing from 4 to 7 carbon atoms and being unsubstituted or substituted by at least one alkyl group containing from 1 to 8 carbon atoms, or a phenyl or phenoxy group unsubstituted or substituted by at least one halogen atom, trifluoromethyl group or alkyl group containing from 1 to 4 carbon atoms, R 4 represents a hydrogen atom or a hydroxy-protecting group which may be removed under acidic conditions, X represents an ethylene group or a cis-vinylene group, the double bonds between the carbon atoms in positions 2 and 3 and between the carbon atoms in positions 13 and 14 are both in trans-configuration, and the wavy line attached to the carbon atom in position 15 represents α- or β-configuration or a mixture thereof, provided that, when R 2 represents a single bond, R 3 does not represent an alkoxy group, a cycloalkoxy group or a phenoxy group) and cyclodextrin clathrates thereof are useful compounds: those in which R 4 represents a hydrogen atom possess selective prostaglandin-like properties.

Inventors

  • 👤 Takashi Yamato
  • 👤 Hirofumi Endo
  • 👤 Kimiichiro Matsumoto
  • 👤 Hajimu Miyake

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-09 22:32
CPC Classifications
C; C07; C07C; C07C405/00; C07C405/0008; C07C405/0041; A; A61; A61P; A61P43/00; C07C405/0033; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 111 words
A prostaglandin analogue of the formula: ##STR20## (wherein R 1 represents an alkyl group containing from 1 to 4 carbon atoms, R 2 represents a single bond or an alkylene group containing from 1 to 5 carbon atoms, R 3 represents an alkyl group containing from 1 to 8 carbon atoms, X represents an ethylene group or a cis-vinylene group, the double bonds between the carbon atoms in positions 2 and 3 and between the carbon atoms in positions 13 and 14 are both in trans-configuration, and the wavy line attached to the carbon atom in position 15 represents α- or β-configuration or a mixture thereof), or a cyclodextrin clathrate thereof.
Claim 2
Dependent Claim 111 words
A prostaglandin analogue of the formula: ##STR20## (wherein R 1 represents an alkyl group containing from 1 to 4 carbon atoms, R 2 represents a single bond or an alkylene group containing from 1 to 5 carbon atoms, R 3 represents an alkyl group containing from 1 to 8 carbon atoms, X represents an ethylene group or a cis-vinylene group, the double bonds between the carbon atoms in positions 2 and 3 and between the carbon atoms in positions 13 and 14 are both in trans-configuration, and the wavy line attached to the carbon atom in position 15 represents α- or β-configuration or a mixture thereof), or a cyclodextrin clathrate thereof.
Claim 3
Dependent Claim 14 words
A prostaglandin analogue according to claim 1, wherein R 1 represents a methyl group.
Claim 4
Dependent Claim 27 words
A prostaglandin analogue according to claim 1, wherein the grouping --R 2 --R 3 represents n-pentyl or n-hexyl unsubstituted or substituted by one or two methyl group(s).
Claim 5
Dependent Claim 22 words
A prostaglandin analogue according to claim 1, wherein the grouping --R 2 --R 3 represents n-pentyl, 1-methylpentyl, 2-methylpentyl, 1,1-dimethylpentyl, hexyl or 2-methylhexyl.
Claim 6
Dependent Claim 16 words
A prostaglandin analogue according to claim 1, wherein the grouping --R 2 --R 3 represents 1,1-dimethylpentyl.
Claim 7
Dependent Claim 27 words
A prostaglandin analogue according to claim 1, wherein the group OH atached to the C-15 carbon atom in formula IV depicted in claim 1 is in α-configuration.
Claim 8
Dependent Claim 15 words
A compound according to claim 1 which is (2E, 13E)-(11α,15R)-N-methanesulphonyl-9-oxo-11,15-dihydroxy-16,16-dimethylprosta-2,13-dien-1amide or a cyclodextrin clathrate thereof.
Claim 9
Dependent Claim 24 words
A compound according to claim 1 which is a cyclodextrin clathrate of a prostaglandin analogue claimed in any one of claims 1 to 6.
Claim 10
Dependent Claim 57 words
A pharmaceutical composition useful in the termination of pregnancy or induction of labour in pregnant female mammals and in contraception and menstrual regulation in female mammals which comprises an effective amount of at least one prostaglandin analogue of general formula IV claimed in claim 1 or cyclodextrin clathrate thereof, in association with a pharmaceutical carrier or coating.
Claim 11
Dependent Claim 20 words
A pharmaceutical composition according to claim 9 in which the active ingredient is (2E, 13E)-(11α,15R)-N-methanesulphonyl-9-oxo-11,15-dihydroxy-16,16-dimethylprosta-2,13-dien-1-amide or a cyclodextrin clathrate thereof.
Claim 12
Dependent Claim 48 words
A method for the termination of pregnancy or induction of labour in a pregnant female mammal or for contraception or menstrual regulation in a female mammal which comprises administering an effective amount of a compound of general formula IV specified in claim 1, or a cyclodextrin clathrate thereof.

References Cited (Backward Citations)

US3954741A Cited
US4024179A Cited
US3931296A Cited
US4024174A Cited
US4034003A Cited
US4073934A Cited
US4191694A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-06-27 1986-12-27 1987-06-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-06-27 1990-12-27 1991-06-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-06-27 1994-12-27 1995-06-28 $7700.00 Window Closed / Lapsed

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