US5175343A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Metal radionuclide labeled proteins for diagnosis and therapy
Assignee: Poniard Pharmaceuticals Inc
•
Filing: 1987-06-19
•
Granted: 1992-12-29
•
Expires: 2007-06-19
Abstract
Abstract Protein conjugated chelated metal radionuclides are provided for use in vivo. Intermediates are provided for preparing the polypeptide compositions efficiently.
Inventors
- 👤 Alan R. Fritzberg
- 👤 Sudhakar Kasina
- 👤 Ananthachari Srinivasan
- 👤 Daniel S. Wilbur
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 01:37
CPC Classifications
C; C07; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; A; A61; A61K; A61K51/00; A61K51/02; A61K51/04; A61K51/0474; A61K51/0478; A61K51/08; A61K51/10; A61K51/1093; A61K51/12; B; B82; B82Y; B82Y5/00; C07C227/00; C07C227/04; C07C227/06; C07C227/08; A61K2123/00
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
182 words
A compound of the formula: ##STR32## wherein: one of Z 1 , Z 2 , Z 3 , or Z 4 is ##STR33## and the others are H 2 or ═O; wherein (CH 2 ) m and (CH 2 ) m ' are aliphatic groups and m=(1-6) and m'=(1-3) and m+m'=(1-6). W is H 2 or ═NH or ═O, with the proviso that the W bonded to the carbon atom bonded to Y is H 2 when Y is --NH 2 ; n is 0 or 1; T is a removable sulfur protective group, hydrogen, or an alkali metal ion; Y is a leaving group of an active ester that reacts with a polypeptide in an aqueous medium to form an amide or amidine bond, wherein said active ester is a carboxylic ester or an imide ester, --NH 2 , --NHNH 2 , or a polypeptide of at least two amino acids; X is a bond, methylene, or CHZ 4 ; and the A's are the same or different and are hydrogen or lower alkyl of from 1 to 3 carbon atoms.
Claim 2
Dependent Claim
182 words
A compound of the formula: ##STR32## wherein: one of Z 1 , Z 2 , Z 3 , or Z 4 is ##STR33## and the others are H 2 or ═O; wherein (CH 2 ) m and (CH 2 ) m ' are aliphatic groups and m=(1-6) and m'=(1-3) and m+m'=(1-6). W is H 2 or ═NH or ═O, with the proviso that the W bonded to the carbon atom bonded to Y is H 2 when Y is --NH 2 ; n is 0 or 1; T is a removable sulfur protective group, hydrogen, or an alkali metal ion; Y is a leaving group of an active ester that reacts with a polypeptide in an aqueous medium to form an amide or amidine bond, wherein said active ester is a carboxylic ester or an imide ester, --NH 2 , --NHNH 2 , or a polypeptide of at least two amino acids; X is a bond, methylene, or CHZ 4 ; and the A's are the same or different and are hydrogen or lower alkyl of from 1 to 3 carbon atoms.
Claim 3
Dependent Claim
11 words
The compound according to claim 1, wherein X is a bond.
Claim 4
Dependent Claim
44 words
The compound according to claim 1, wherein the W bonded to the carbon atom bonded to Y is ═O and wherein Y is a leaving group of an active ester that reacts with a polypeptide in an aqueous medium to form an amide bond.
Claim 5
Dependent Claim
13 words
The compound according to claim 3, wherein said ester is a 2,3,5,6-tetrafluorophenyl ester.
Claim 6
Dependent Claim
34 words
The compound according to claim 1, wherein X is a bond, Z 3 is ═O, and one of Z 1 or Z 2 is ##STR34## and the other is ═O or H 2 .
Claim 7
Dependent Claim
101 words
A compound of the formula: ##STR35## wherein: each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR36## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, R 4 represents a lower alkyl group of from one to about three carbon atoms, and R 5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms, and Y represents the leaving group of an active ester, wherein said active ester is a carboxylic ester or an imide ester.
Claim 8
Dependent Claim
101 words
A compound of the formula: ##STR35## wherein: each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR36## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, R 4 represents a lower alkyl group of from one to about three carbon atoms, and R 5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms, and Y represents the leaving group of an active ester, wherein said active ester is a carboxylic ester or an imide ester.
Claim 9
Dependent Claim
209 words
A compound of the formula: ##STR37## wherein: one of Z 1 , Z 2 , Z 3 , or Z 4 is (CH 2 ) n -CWY, wherein n=1-6, and the others are H 2 or ═O; W is H 2 or ═NH or ═O, with the proviso that W is H 2 when Y is --NH 2 ; Y is a leaving group of an active ester that reacts with a polypeptide in an aqueous medium to form an amide or amidine bond, wherein said active ester is a carboxylic ester or an imide ester, --NH 2 , --NHNH 2 , or a polypeptide of at least two amino acids; X is a bond, methylene, or CHZ 4 ; the A's are the same or different and are hydrogen or lower alkyl 3 carbon atoms; and each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR38## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, and R 4 represents a lower alkyl group of from one to about three carbon atoms, and R5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms.
Claim 10
Dependent Claim
209 words
A compound of the formula: ##STR37## wherein: one of Z 1 , Z 2 , Z 3 , or Z 4 is (CH 2 ) n -CWY, wherein n=1-6, and the others are H 2 or ═O; W is H 2 or ═NH or ═O, with the proviso that W is H 2 when Y is --NH 2 ; Y is a leaving group of an active ester that reacts with a polypeptide in an aqueous medium to form an amide or amidine bond, wherein said active ester is a carboxylic ester or an imide ester, --NH 2 , --NHNH 2 , or a polypeptide of at least two amino acids; X is a bond, methylene, or CHZ 4 ; the A's are the same or different and are hydrogen or lower alkyl 3 carbon atoms; and each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR38## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, and R 4 represents a lower alkyl group of from one to about three carbon atoms, and R5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms.
Claim 11
Dependent Claim
15 words
The compound of claim 7 wherein said hemithioacetal sulfur protective group is an ethoxyethyl group.
Claim 12
Dependent Claim
6 words
A compound of the formula: ##STR39##
Claim 13
Dependent Claim
6 words
A compound of the formula: ##STR39##
Claim 14
Dependent Claim
88 words
A compound of the formula: ##STR40## wherein: Y represents a leaving group selected from ##STR41## and each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR42## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, R 4 represents a lower alkyl group of from one to about three carbon atoms, and R 5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms.
Claim 15
Dependent Claim
88 words
A compound of the formula: ##STR40## wherein: Y represents a leaving group selected from ##STR41## and each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR42## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, R 4 represents a lower alkyl group of from one to about three carbon atoms, and R 5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms.
Claim 16
Dependent Claim
15 words
The compound of claim 10, wherein said hemithioacetal sulfur protective group is an ethoxyethyl group.
Claim 17
Dependent Claim
184 words
A compound of the formula: ##STR43## wherein: one of Z 1 , Z 2 , Z 3 , or Z 4 is --(CH 2 ) n --CWY, wherein n is 1-3, and the others are H 2 or ═O; W is ═NH or ═O; Y is the leaving group of an active ester that reacts with a polypeptide in an aqueous medium to form an amide or amidine bond, wherein said active ester is a carboxylic ester or an imide ester; X is a bond, methylene, or CHZ 4 ; the A's are the same or different and are hydrogen or noncyclic lower alkyl of from 1 to 3 carbon atoms; and each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR44## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, R 4 represents a lower alkyl group of from one to about three carbon atoms, and R 5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms.
Claim 18
Dependent Claim
184 words
A compound of the formula: ##STR43## wherein: one of Z 1 , Z 2 , Z 3 , or Z 4 is --(CH 2 ) n --CWY, wherein n is 1-3, and the others are H 2 or ═O; W is ═NH or ═O; Y is the leaving group of an active ester that reacts with a polypeptide in an aqueous medium to form an amide or amidine bond, wherein said active ester is a carboxylic ester or an imide ester; X is a bond, methylene, or CHZ 4 ; the A's are the same or different and are hydrogen or noncyclic lower alkyl of from 1 to 3 carbon atoms; and each T, when taken together with the sulfur atom to be protected, defines a hemithioacetal sulfur protective group of the formula: ##STR44## wherein R 3 represents a lower alkyl group of from about two to about five carbon atoms, R 4 represents a lower alkyl group of from one to about three carbon atoms, and R 5 represents hydrogen or a lower alkyl group of from one to about three carbon atoms.
References Cited (Backward Citations)
US3989730A
Cited
US4416865A
Cited
US4208398A
Cited
US4233285A
Cited
US4115541A
Cited
US4032625A
Cited
US4027005A
Cited
US3987157A
Cited
US3974268A
Cited
US4017595A
Cited
US4233284A
Cited
US4232000A
Cited
US4363793A
Cited
US4421735A
Cited
US4474746A
Cited
US4418052A
Cited
US4564472A
Cited
US4444690A
Cited
US4454106A
Cited
US4472509A
Cited
US4479930A
Cited
US4571430A
Cited
US4434151A
Cited
US4575556A
Cited
US4615876A
Cited
US4673562A
Cited
US4582700A
Cited
US4963682A
Cited
US4963688A
Cited
US4861869A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-12-29 | 1996-06-29 | 1996-12-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-12-29 | 2000-06-29 | 2000-12-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-12-29 | 2004-06-29 | 2004-12-29 | $7700.00 | Window Closed / Lapsed |