US4652553A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Steroidal glycolipids as host resistance stimulators
Assignee: Merck and Co Inc
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Filing: 1985-11-25
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Granted: 1987-03-24
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Expires: 2005-11-25
Abstract
Abstract Described are derivatives of glycolipids with substituted steroids bridged via a medium length hydrocarbon chain to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses. These compounds protect an immunocompromised human or animal host against opportunistic infection by virtue of their immunostimulant properties.
Inventors
- 👤 William K. Hagmann
- 👤 Philippe L. Durette
- 👤 Mitree M. Ponpipom
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 02:37
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/70; A61K31/7028; A61K31/7034; A61K31/704; C; C07; C07J; C07J31/00; C07J31/006; C07J41/00; C07J41/0033; C07J41/0088
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
172 words
A pharmaceutical composition for enhancing host resistance in an immunocompromised individual consisting essentially of a compound of the formula: ##STR23## where: R 1 is selected from the group consisting of α or β-D-1-thiomannopyranoside, α or β-L-1-thiofucopyranoside; A is selected from the group consisting of (CH 2 ) n where n is 5-7, or (CH 2 ) k X(CH 2 ) m where X is O or S or NH and k and m are independently 2-4 and the sum of k and m is 4-6; R 2 is selected from the group consisting of C 1 -C 8 alkyl or C 2 -C 10 alkene ##STR24## where B is C 1 -C 8 alkyl, C 1 -C 8 alkoxy, NR 3 R 4 where R 3 and R 4 are independently H, C 1 -C 4 alkyl; CH(CH 3 )D where D is OH, NH 2 , NHR 5 where R 5 is C 1 -C 10 alkyl, and pharmaceutically acceptable salts thereof, said composition also containing a pharmaceutically acceptable carrier therefor.
Claim 2
Dependent Claim
172 words
A pharmaceutical composition for enhancing host resistance in an immunocompromised individual consisting essentially of a compound of the formula: ##STR23## where: R 1 is selected from the group consisting of α or β-D-1-thiomannopyranoside, α or β-L-1-thiofucopyranoside; A is selected from the group consisting of (CH 2 ) n where n is 5-7, or (CH 2 ) k X(CH 2 ) m where X is O or S or NH and k and m are independently 2-4 and the sum of k and m is 4-6; R 2 is selected from the group consisting of C 1 -C 8 alkyl or C 2 -C 10 alkene ##STR24## where B is C 1 -C 8 alkyl, C 1 -C 8 alkoxy, NR 3 R 4 where R 3 and R 4 are independently H, C 1 -C 4 alkyl; CH(CH 3 )D where D is OH, NH 2 , NHR 5 where R 5 is C 1 -C 10 alkyl, and pharmaceutically acceptable salts thereof, said composition also containing a pharmaceutically acceptable carrier therefor.
Claim 3
Dependent Claim
19 words
The composition of claim 1 wherein said compound is present in an amount effective to exert an immunostimulant effect.
Claim 4
Dependent Claim
10 words
The composition of claim 1 wherein R 2 is 2,6-dimethylhexyl.
Claim 5
Dependent Claim
10 words
The composition of claim 1 wherein R 2 is 2,6-dimethyl-3-ethyl-hex-4-enyl.
Claim 6
Dependent Claim
7 words
The composition of claim 1 wherein ##STR25##
Claim 7
Dependent Claim
24 words
The composition of claim 1 wherein CH(CH 3 )D is CH 3 --CHOH--, CH 3 CH(NHCOCH 3 )--, or CH 3 CH(NH 2 )--.
Claim 8
Dependent Claim
28 words
The composition of claim 1 wherein the compound is selected from the following: 6-(5-Cholesten-3β-yloxy)hexyl-1-thio-α-D-mannopyranoside; 6-(5-Cholesten-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside; 6-(5-Cholesten-3β-yloxy)hexyl-1-thio-α-L-fucopyranoside; 6-(5-Cholesten-3β-yloxy)hexyl-1-thio-β-L-fucopyranoside; 2-(2-(5-Cholesten-3β-yloxy)ethoxy)ethyl-1-thio-β-D-mannopyranoside; 6-(Stigmasta-5,22-dien-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside; 6-(Pregn-5-en-20-one-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside; 6-(17β-Carbomethoxy-androst-5-en-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside; 6-(17β-Carbamido-androst-5-en-3β-yloxy)-hexyl-1-thio-β-D-mannopyranoside; 6-(Pregn-5-en-20-ol-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside; 6-(20S-Acetamido-pregn-5-en-3β-yloxy)-hexyl-1-thio-β-D-mannopyranoside; 6-(20R-Acetamido-pregn-5-en-3β-yloxy)-hexyl-1-thio-β-D-mannopyranoside; 6-(20S-Amino-pregn-5-en-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside; or 6-(20R-Amino-pregn-5-en-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside
Claim 9
Dependent Claim
10 words
The composition of claim 1 wherein said compound is 6-(5-cholesten-3β-yloxy)hexyl-1-thio-β-D-mannopyranoside.
Claim 10
Dependent Claim
30 words
A method for stimulating host resistance in an immunocompromised animal or human host to bacterial or fungal infection comprising administering to said host the composition as defined in claim 1.
Claim 11
Dependent Claim
14 words
The method of claim 9 wherein said composition is administered intramuscularly, subcutaneously or intraperitoneally.
Claim 12
Dependent Claim
13 words
The method of claim 10 wherein said composition further comprises an aqueous vehicle.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-03-23 | 1990-09-22 | 1991-03-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-03-23 | 1994-09-22 | 1995-03-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-03-23 | 1998-09-22 | 1999-03-24 | $7700.00 | Window Closed / Lapsed |