US3932389A
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2-Descarboxy-2-(tetrazol-5-yl)-11-desoxy-15-substituted-.omega.-pentanorprostaglandins
Assignee: Pfizer Inc
•
Filing: 1974-12-11
•
Granted: 1976-01-13
•
Expires: 1994-12-11
Abstract
Abstract The 2-descarboxy-2-(tetrazol-5-yl)-11-desoxy-15-substituted-ω-pentanorprostaglandins and various intermediates employed in their preparation. The novel prostaglandins of this invention have been found to have activity profiles comparable to the parent prostaglandins, but exhibit a greater tissue specificity of action.
Inventors
- 👤 Michael R. Johnson
- 👤 Thomas K. Schaaf
- 👤 Jasjit S. Bindra
- 👤 Hans-Jurgen E. Hess
- 👤 James F. Eggler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 04:10
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; A; A61; A61K; A61K31/00; A61K31/185; A61K31/19; A61K31/21; A61K31/215; A61K31/33; A61K31/335; A61K31/34; A61K31/35; A61K31/38; A61P; A61P43/00; C07C; C07C405/00; C07C61/00; C07C61/06; C07C69/00; C07C69/74; C07D307/00; C07D307/77; C07D307/93; C07D307/935; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07D317/00; C07D317/08; C07D317/44; C07D317/46; C07D317/48; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D405/00; C07D405/02; C07D405/12; C07D407/00; C07D407/02; C07D407/06; C07D409/00; C07D409/02; C07D409/06; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/1896; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C07F9/4056; C07F9/4059; C07F9/547; C07F9/6524
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
68 words
2-descarboxy-2-[tetrazol-5-yl]-11-desoxy-ω-pentanorprostaglandins and their C 15 epimers having at the 15-position a hydroxy or a keto group and one substituent of the formula: ##EQU8## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; and R is hydrogen or methyl.
Claim 2
Dependent Claim
68 words
2-descarboxy-2-[tetrazol-5-yl]-11-desoxy-ω-pentanorprostaglandins and their C 15 epimers having at the 15-position a hydroxy or a keto group and one substituent of the formula: ##EQU8## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; and R is hydrogen or methyl.
Claim 3
Dependent Claim
75 words
2-descarboxy-2-[tetrazol-5-yl]-11-desoxy-ω-pentanorprotaglandins of the E or F series and their C 15 epimers having at the 15-position a hydroxy or keto group and one substituent of the formula: ##EQU9## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β -thienyl; α- or β -naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; and R is hydrogen or methyl.
Claim 4
Dependent Claim
75 words
2-descarboxy-2-[tetrazol-5-yl]-11-desoxy-ω-pentanorprotaglandins of the E or F series and their C 15 epimers having at the 15-position a hydroxy or keto group and one substituent of the formula: ##EQU9## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β -thienyl; α- or β -naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; and R is hydrogen or methyl.
Claim 5
Dependent Claim
76 words
A compound of the structure: ##SPC17## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl, 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; Z is a single bond or trans double bond; and M and N are each keto, ##EQU10##
Claim 6
Dependent Claim
76 words
A compound of the structure: ##SPC17## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl, 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; Z is a single bond or trans double bond; and M and N are each keto, ##EQU10##
Claim 7
Dependent Claim
69 words
A compound of the structure; ##SPC18## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 8
Dependent Claim
69 words
A compound of the structure; ##SPC18## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 9
Dependent Claim
69 words
A compound of the formula: ##SPC19## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 10
Dependent Claim
69 words
A compound of the formula: ##SPC19## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 11
Dependent Claim
71 words
A compound of the formula: ##SPC20## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β -thienyl; 5-lower alkyl-α- or β -thienyl; α- or β-naphthyl; tropyl, phenyl, 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 12
Dependent Claim
71 words
A compound of the formula: ##SPC20## wherein Ar is α- or β-thienyl; 5-phenyl-α- or β -thienyl; 5-lower alkyl-α- or β -thienyl; α- or β-naphthyl; tropyl, phenyl, 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 13
Dependent Claim
75 words
A compound of the structure: ##SPC21## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 14
Dependent Claim
75 words
A compound of the structure: ##SPC21## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 15
Dependent Claim
75 words
A compound of the structure: ##SPC22## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 16
Dependent Claim
75 words
A compound of the structure: ##SPC22## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 17
Dependent Claim
75 words
A compound of the structure: ##SPC23## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosbustituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 18
Dependent Claim
75 words
A compound of the structure: ##SPC23## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosbustituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; and Z is a single bond or trans double bond.
Claim 19
Dependent Claim
85 words
A compound of the structure: ##SPC24## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; Z is a single bond or trans double bond; R 1 is tetrahydropyranyl or dimethyl-tert-butylsilyl; and ##EQU11## or = 0.
Claim 20
Dependent Claim
85 words
A compound of the structure: ##SPC24## and the C 15 epimers thereof, wherein Ar is α- or β-thienyl; 5-phenyl-α- or β-thienyl; 5-lower alkyl-α- or β-thienyl; α- or β-naphthyl; tropyl, phenyl; 3,5-dimethylphenyl; 3,4-dimethoxyphenyl; 3,4-methylenedioxyphenyl; 3,4-dichlorophenyl; and monosubstituted phenyl wherein said substituent is bromo, chloro, fluoro, trifluoromethyl, phenyl, lower alkyl, or lower alkoxy; R is hydrogen or methyl; W is a single bond or cis double bond; Z is a single bond or trans double bond; R 1 is tetrahydropyranyl or dimethyl-tert-butylsilyl; and ##EQU11## or = 0.
Claim 21
Dependent Claim
19 words
A compound of claim 3 wherein W is a cis double bond and Z is a trans double bond.
Claim 22
Dependent Claim
18 words
A compound of claim 3 wherein W is a cis double bond and Z is a single bond.
Claim 23
Dependent Claim
13 words
A compound of claim 3 wherein both W and Z are single bonds.
Claim 24
Dependent Claim
18 words
A compound of claim 3 wherein W is a single bond and Z is a trans double bond.
Claim 25
Dependent Claim
19 words
A compound of claim 4 wherein W is a cis double bond and Z is a trans double bond.
Claim 26
Dependent Claim
18 words
A compound of claim 4 wherein W is a cis double bond and Z is a single bond.
Claim 27
Dependent Claim
18 words
A compound of claim 4 wherein W is a single bond and Z is a trans double bond.
Claim 28
Dependent Claim
13 words
A compound of claim 4 wherein both W and Z are single bonds.
Claim 29
Dependent Claim
19 words
A compound of claim 9 wherein W is a cis double bond and Z is a trans double bond.
Claim 30
Dependent Claim
13 words
A compound of claim 9 wherein both W and Z are single bonds.
Claim 31
Dependent Claim
18 words
A compound of claim 9 wherein W is a cis double bond and Z is a single bond.
Claim 32
Dependent Claim
18 words
A compound of claim 9 wherein W is a single bond and Z is a trans double bond.
Claim 33
Dependent Claim
30 words
A compound of the structure: ##SPC25## wherein R 2 is alkyl of from 1 to 8 carbons, phenalkyl of up to 9 carbons, phenyl, tolyl, p-biphenyl and α- or β-naphthyl.
Claim 34
Dependent Claim
30 words
A compound of the structure: ##SPC25## wherein R 2 is alkyl of from 1 to 8 carbons, phenalkyl of up to 9 carbons, phenyl, tolyl, p-biphenyl and α- or β-naphthyl.
Claim 35
Dependent Claim
25 words
A compound of claim 4 wherein Ar is m-tolyl, W is a cis double bond, Z is a trans double bond, and R is hydrogen.
Claim 36
Dependent Claim
25 words
A compound of claim 4 wherein Ar is phenyl, W is a cis double bond, Z is a trans double bond, and R is hydrogen.
Claim 37
Dependent Claim
19 words
A compound of claim 4 wherein Ar is phenyl, W and Z are single bonds, and R is hydrogen.
Claim 38
Dependent Claim
24 words
A compound of claim 4 wherein Ar is phenyl, W is a single bond, Z is a trans double bond, and R is hydrogen.
Claim 39
Dependent Claim
24 words
A compound of claim 4 wherein Ar is m-tolyl, W is a cis double bond, Z is a single bond, and R is hydrogen.
Claim 40
Dependent Claim
25 words
A compound of claim 6 wherein Ar is m-tolyl, W is a cis double bond, Z is a trans double bond, and R is hydrogen.
Claim 41
Dependent Claim
24 words
A compound of claim 6 wherein Ar is m-tolyl, W is a cis double bond, Z is a single bond, and R is hydrogen.
Claim 42
Dependent Claim
25 words
A compound of claim 9 wherein Ar is 5-phenyl-α-thienyl, W is a cis double bond, Z is a trans double bond, and R is hydrogen.
Claim 43
Dependent Claim
25 words
A compound of claim 9 wherein Ar is phenyl, W is a cis double bond, Z is a trans double bond, and R is (-)-methyl.
Claim 44
Dependent Claim
25 words
A compound of claim 9 wherein Ar is phenyl, W is a cis double bond, Z is a trans double bond, and R is (+)-methyl.
Claim 45
Dependent Claim
29 words
A compound of claim 9 wherein Ar is β-naphthyl, W is a cis double bond, Z is a trans double bond, R is hydrogen, and said prostaglandin is racemic.
Claim 46
Dependent Claim
33 words
A compound of claim 9 wherein Ar is β-naphthyl, W is a cis double bond, Z is a trans double bond, R is hydrogen, and said prostaglandin is a racemic C 15 epimer.
Claim 47
Dependent Claim
19 words
A compound of claim 9 wherein Ar is phenyl, W and Z are single bonds, and R is hydrogen.
Claim 48
Dependent Claim
25 words
A compound of claim 9 wherein Ar is m-tolyl, W is a cis double bond, Z is a trans double bond, and R is hydrogen.
References Cited (Backward Citations)
US3883513A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-12 | 1979-07-14 | 1980-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-12 | 1983-07-14 | 1984-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-12 | 1987-07-14 | 1988-01-13 | $7700.00 | Window Closed / Lapsed |