US5280015A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-substituted adenosines and 2-substituted adenosine 5'-carboxamides
Assignee: HEALTH AND HUMAN SERVICES United States, Secretary of, Department of
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Filing: 1990-09-05
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Granted: 1994-01-18
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Expires: 2010-09-05
Abstract
Abstract The present invention is directed to compounds useful as probes for characterizing and studying the adenosine A 2 receptor. The present invention is also directed to methods of treating central nervous system disorders and cardiovascular disorders which include treating hypertension and thrombosis by administering said compounds.
Inventors
- 👤 Kenneth A. Jacobson
- 👤 R. Tyler McCabe
- 👤 Phil Skolnick
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 11:20
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/70; C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/16
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
64 words
A compound having the formula ##STR32## wherein R is H, C 1 -C 7 lower alkyl, C 1 -C 7 lower alkenyl, an acyl radical of the formula R--C(O)--, an isothiocyanate radical, or a reporter group; and R 2 is (CH 2 ) n OH or CONH(CH 2 ) n H or CONH-cyclopropyl wherein n=1-4, and wherein s=1-6, or a physiologically acceptable salt thereof.
Claim 2
Dependent Claim
64 words
A compound having the formula ##STR32## wherein R is H, C 1 -C 7 lower alkyl, C 1 -C 7 lower alkenyl, an acyl radical of the formula R--C(O)--, an isothiocyanate radical, or a reporter group; and R 2 is (CH 2 ) n OH or CONH(CH 2 ) n H or CONH-cyclopropyl wherein n=1-4, and wherein s=1-6, or a physiologically acceptable salt thereof.
Claim 3
Dependent Claim
109 words
The compound according to claim 1 having the formula ##STR33## wherein R is H, C 1 -C 4 lower alkyl, C 1 -C 4 lower alkenyl, ##STR34## and wherein R 1 =OH, NH 2 , NHCO 2 CH 2 C 6 H 5 , (CH 2 ) m X, m=0-4, X=Cl, F, or Br, and p=0-4, ##STR35## and wherein A=0 or S, and q=0-4, CO(CH 2 ) n X, ##STR36## wherein R 3 is NCS or SO 3 Na; or a reporter group; and R 2 is (CH 2 ) n OH or CONH(CH 2 ) n CH 3 or CONH-cyclopropyl wherein n=1-4; or a physiologically acceptable salt thereof.
Claim 4
Dependent Claim
36 words
The compound according to claim 2 wherein said reporter group is selected from the group consisting of a spectroscopic reporter group, a fluorescent dye, a chemical or photochemical affinity probe and a spin label probe .
Claim 5
Dependent Claim
13 words
The compound according to claim 2 wherein R is a radiolabeled prosthetic group.
Claim 6
Dependent Claim
37 words
The compound according to claim 3 wherein said fluorescent dye is selected from the group consisting of 5- (and 6-)-carboxynaphthofluorescein, 5-(and 6-) carboxyfluorescein 7-hydroxycoumarin-4-acetic acid, acridone-10-acetic acid, tetramethylrhodamine-5-(and-6)-isothiocyanate (TRITC), 1-pyreneisothiocyanate, 9-acridineisothiocyanate, and 4,4'-diisothiocyanatostilbene-2,2'-disulfonic acid, disodium salt (DIDS).
Claim 7
Dependent Claim
34 words
The compound of claim 3 wherein said spin label probes are selected from the group consisting of 4-isothiocyanate-2,2,6,6,-tetramethyl piperidinyloxy free radical, N-(4-(iodoacetyl)amino)-2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO 1A), N-(3-(iodoacetyl)amino)-2,2,5,5-tetramethylpyrrolidine-1-oxyl (PROXYL 1A), succinimidyl 2,2,5,5-tetramethyl-3-pyrroline-1-oxyl-3-carboxylate, 2,2,5,5-tetramethyl-3-pyrroline-1-oxyl-3-carboxylic acid, and 9-doxylstearic acid.
Claim 8
Dependent Claim
15 words
The compound of claim 6 wherein said spin label probe is 4-isothiocyanate-2,2,6,6-tetramethyl piperidinyloxy free radical.
Claim 9
Dependent Claim
40 words
The compound according to claim 3 wherein said photoaffinity probe is selected from the group consisting of bromoacetyl, m- or p-phenylenediisothiocyanate, N-succinimidyl suberic acid, 4-azidosalicylic acid, 2-(p-azidosalicylamido)ethyl-1,3'dithiopropionic acid, 5-azido-2-nitrobenzoic acid, 2-(m-azido-o-nitrobenzamido)ethyl-1,3'dithiopropionic acid, 6-(4'-azido-2'-nitrophenylamino)hexanoate, (4-azidophenyl)-1,3'-dithiopropionic acid, 4-azidobenzoic acid, 4-azidophenylisothiocyanate, 2-diazo-3,3,3-trifluoropropionic acid.
Claim 10
Dependent Claim
32 words
The compound according to claim 4 wherein said radiolabeled compound is selected from the group consisting of diethylenetriaminepentacetic acid, ethylenediamine tetraacetic acid, 2-p-nitrobenzyl-1,4,7,10-tetraazacyclododecane-N,N',N",N"'-tetraacetic acid, dimercaptosuccinate, N,N'-1,2-ethylenediylbis-L-cysteine diethyl ester, p-hydroxyphenylpropionic acid, p-aminobenzoic acid.
Claim 11
Dependent Claim
101 words
A pharmaceutical composition comprising an effective amount of the compound according to claim 2 having the formula ##STR37## wherein R is H, C 1 -C 4 lower alkyl, C 1 -C 4 lower alkenyl, ##STR38## and R 1 is H, OH, NH 2 , NHCO 2 CH 2 C 6 H 5 , (CH 2 ) m X, wherein m=0-4, X=Cl, Br or F, wherein p=0-4, ##STR39## and A is O, or S, q=0-4; and R 2 is (CH 2 ) n OH, CONH(CH 2 ) n H and n=1-4, or a physiologically acceptable salt thereof; and a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
EP0354180A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1997-01-17 | 1997-07-19 | 1998-01-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2001-01-17 | 2001-07-19 | 2002-01-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2005-01-17 | 2005-07-19 | 2006-01-18 | $7700.00 | Window Closed / Lapsed |