US5457183A
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US
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Hydroxylated texaphyrins
Assignee: Pharmacyclics LLC
•
Filing: 1993-10-12
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Granted: 1995-10-10
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Expires: 2013-10-12
Abstract
Abstract A method of using texaphyrins as radiosensitizers. Advantageous properties of texaphyrins for use as a radiosensitizer include i) a low redox potential which allows radiation induced solvated electrons to flow to texaphyrin rather than neutralizing hydroxyl radicals, allowing the hydroxyl radicals to cause cellular damage, ii) a relatively stable texaphyrin radical which, nevertheless, reacts readily to covalently modify neighboring molecules causing further cellular damage, and iii) intrinsic biolocalization and indifference to the presence of O2 which allow texaphyrin to be particularly effective for treating the hypoxic areas of solid tumors. Sensitizer enhancement ratios of 1.62 and 2.2 were achieved at 20 mu M and 80 mu M gadolinium-texaphyrin, respectively, with a mouse leukemia cell line. Methods of treatment for an individual having a tumor include the use of a texaphyrin as a radiosensitizer and as an agent for photodynamic tumor therapy, or the use of a texaphyrin for internal and for external ionizing radiation. New water soluble hydroxy-substituted texaphyrins are described.
Inventors
- 👤 Jonathan L. Sessler
- 👤 Tarak D. Mody
- 👤 Gregory W. Hemmi
- 👤 Vladimir Kral
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 17:44
CPC Classifications
A; A61; A61K; A61K51/00; A61K51/02; A61K51/04; A61K51/0474; A61K51/0485; A61K41/00; A61K41/0038; A61K41/0057; A61K41/0076; A61K47/00; A61K47/50; A61K47/51; A61K47/54; A61K47/545; A61K47/546; A61K49/00; A61K49/001; A61K49/0013; A61K49/0017; A61K49/0019; A61K49/0021; A61K49/005; A61K49/0054; A61K49/06; A61K49/08; A61K49/085; A61K49/10; A61K49/101; A61K49/106; A61K49/12; A61K49/126; A61L; A61L2/00; A61L2/02; A61P; A61P35/00; A61P35/02; A61P43/00; B; B01; B01J; B01J31/00; B01J31/16; B01J31/165; B01J31/1658; B01J31/18; B01J31/1805; B01J31/181; B01J31/1815; C; C07; C07D; C07D487/00; C07D487/22; C07H; C07H21/00; A61L2103/00; A61L2103/05; B01J2531/00; B01J2531/02; B01J2531/0238; B01J2531/0241; B01J2531/025; B01J2531/20; B01J2531/23; B01J2531/26; B01J2531/27; B01J2531/28; B01J2531/30; B01J2531/36; B01J2531/37; B01J2531/38; B01J2531/70; B01J2531/72; B01J2531/80; B01J2531/84; B01J2531/842; B01J2531/845; B01J2531/847; B01J2531/90; B01J2531/96; B01J31/02; B01J31/06; B01J31/061
Claims Analysis
Total Claims: 60
Claim 1
Independent Claim
261 words
A water soluble compound retaining lipophilicity and having the structure: ##STR5## wherein M is H, a divalent metal cation selected from the group consisting of Ca +2 , Mn +2 , Co +2 , Ni +2 , Zn +2 , Cd +2 , Hg +2 , Fe +2 , Sm +2 and UO 2 +2 or a trivalent metal cation selected from the group consisting of Mn +3 , Co +3 , Ni +3 , Fe +3 , Ho +3 , Ce +3 , Y +3 , In +3 , Pr +3 , Nd +3 , Sm +3 , Eu +3 , Gd +3 , Tb +3 , Dy +3 , Er +3 , Tm +3 , Yb +3 , Lu +3 , La +3 , and U +3 ; R 2 and R 3 are CH 2 CH 3 , R 4 is CH 3 , R 1 , R 5 and R 6 are independently hydrogen, hydroxyl, alkyl, hydroxyalkyl, oxyalkyl, oxyhydroxyalkyl, saccharide, carboxyalkyl, carboxyamidealkyl, antibody, a peptide having affinity for a biological receptor, a sapphyrin molecule, or a couple to an antibody, a peptide having affinity for a biological receptor, or a sapphyrin molecule, where at least one of R 1 , R 5 , and R 6 is oxyhydroxyalkyl, saccharide, oxyalkyl, carboxyalkyl, carboxyamidealkyl, hydroxyalkyl, an antibody, a peptide having affinity for a biological receptor, a sapphyrin molecule, or a couple to an antibody, a peptide having affinity for a biological receptor, or a sapphyrin molecule, having at least one hydroxy substituent; and N is 0, 1 or 2.
Claim 2
Dependent Claim
261 words
A water soluble compound retaining lipophilicity and having the structure: ##STR5## wherein M is H, a divalent metal cation selected from the group consisting of Ca +2 , Mn +2 , Co +2 , Ni +2 , Zn +2 , Cd +2 , Hg +2 , Fe +2 , Sm +2 and UO 2 +2 or a trivalent metal cation selected from the group consisting of Mn +3 , Co +3 , Ni +3 , Fe +3 , Ho +3 , Ce +3 , Y +3 , In +3 , Pr +3 , Nd +3 , Sm +3 , Eu +3 , Gd +3 , Tb +3 , Dy +3 , Er +3 , Tm +3 , Yb +3 , Lu +3 , La +3 , and U +3 ; R 2 and R 3 are CH 2 CH 3 , R 4 is CH 3 , R 1 , R 5 and R 6 are independently hydrogen, hydroxyl, alkyl, hydroxyalkyl, oxyalkyl, oxyhydroxyalkyl, saccharide, carboxyalkyl, carboxyamidealkyl, antibody, a peptide having affinity for a biological receptor, a sapphyrin molecule, or a couple to an antibody, a peptide having affinity for a biological receptor, or a sapphyrin molecule, where at least one of R 1 , R 5 , and R 6 is oxyhydroxyalkyl, saccharide, oxyalkyl, carboxyalkyl, carboxyamidealkyl, hydroxyalkyl, an antibody, a peptide having affinity for a biological receptor, a sapphyrin molecule, or a couple to an antibody, a peptide having affinity for a biological receptor, or a sapphyrin molecule, having at least one hydroxy substituent; and N is 0, 1 or 2.
Claim 3
Dependent Claim
29 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONCH(CH 2 OH) 2 and R 5 and R 6 are OCH 3 .
Claim 4
Dependent Claim
33 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONCH(CH 2 OH) 2 and R 5 and R 6 are OCH 2 CH 2 CH 2 OH.
Claim 5
Dependent Claim
31 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONCH(CH 2 OH) 2 and R 5 and R 6 are OCH 2 CH 2 OH.
Claim 6
Dependent Claim
56 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONCH(CH 2 OH) 2 and R 5 and R 6 are O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 7
Dependent Claim
32 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONCH(CH 2 OH) 2 and R 5 and R 6 are independently H or CH 3 .
Claim 8
Dependent Claim
80 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONCH(CH 2 OH) 2 , R 5 is CH 3 , and R 6 is H, CH 3 , OCH 3 , OCH 2 CH 2 OH, OCH 2 CH 2 CH 2 OH, or O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 9
Dependent Claim
31 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CON(CH 2 CH 2 OH) 2 and R 5 and R 6 are OCH 3 .
Claim 10
Dependent Claim
35 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CON(CH 2 CH 2 OH) 2 and R 5 and R 6 are OCH 2 CH 2 CH 2 OH.
Claim 11
Dependent Claim
33 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CON(CH 2 CH 2 OH) 2 and R 5 and R 6 are OCH 2 CH 2 OH.
Claim 12
Dependent Claim
58 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CON(CH 2 CH 2 OH) 2 and R 5 and R 6 are O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 13
Dependent Claim
34 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CON(CH 2 CH 2 OH) 2 and R 5 and R 6 are independently H or CH 3 .
Claim 14
Dependent Claim
82 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CON(CH 2 CH 2 OH) 2 , R 5 is CH 3 , and R 6 is H, CH 3 , OCH 3 , OCH 2 CH 2 OH, OCH 2 CH 2 CH 2 OH, or O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 15
Dependent Claim
30 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHCH 2 CH(OH)CH(OH)CH(OH)CH(OH)CH 2 OH and R 5 and R 6 are OCH 3 .
Claim 16
Dependent Claim
34 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHCH 2 CH(OH)CH(OH)CH(OH)CH(OH)CH 2 OH and R 5 and R 6 are OCH 2 CH 2 CH 2 OH.
Claim 17
Dependent Claim
32 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHCH 2 CH(OH)CH(OH)CH(OH)CH(OH)CH 2 OH and R 5 and R 6 are OCH 2 CH 2 OH.
Claim 18
Dependent Claim
57 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHCH 2 CH(OH)CH(OH)CH(OH)CH(OH)CH 2 OH and R 5 and R 6 are O(CH 2 CH 20 ) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 19
Dependent Claim
33 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHCH 2 CH(OH)CH(OH)CH(OH)CH(OH)CH 2 OH and R 5 and R 6 are independently H or CH 3 .
Claim 20
Dependent Claim
81 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHCH 2 CH(OH)CH(OH)CH(OH)CH(OH) CH 2 OH, R 5 is CH 3 , and R 6 is H, CH 3 , OCH 3 , OCH 2 CH 2 OH, OCH 2 CH 2 CH 2 OH, or O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 21
Dependent Claim
28 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are OCH 3 .
Claim 22
Dependent Claim
32 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are OCH 2 CH 2 CH 2 OH.
Claim 23
Dependent Claim
30 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are OCH 2 CH 2 OH.
Claim 24
Dependent Claim
53 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are O(CH 2 CH 20 ) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CHB.
Claim 25
Dependent Claim
31 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are independently H or CH 3 .
Claim 26
Dependent Claim
78 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH, R 5 is CH 3 , and R 6 is H, CH 3 , OCH 3 , OCH 2 CH 2 OH, OCH 2 CH 2 CH 2 OH, or O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 27
Dependent Claim
31 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHC 6 H 11 O 5 and R 5 and R 6 are OCH 3 .
Claim 28
Dependent Claim
35 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHC 6 H 11 O 5 and R 5 and R 6 are OCH 2 CH 2 CH 2 OH.
Claim 29
Dependent Claim
33 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHC 6 H 11 O 5 and R 5 and R 6 are OCH 2 CH 2 OH.
Claim 30
Dependent Claim
58 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHC 6 H 11 O 5 and R 5 and R 6 are O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 31
Dependent Claim
34 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHC 6 H 11 O 5 and R 5 and R 6 are independently H or CH 3 .
Claim 32
Dependent Claim
82 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CONHC 6 H 11 O 5 , R 5 is CH 3 , and R 6 is H, CH 3 , OCH 3 , OCH 2 CH 2 OH, OCH 2 CH 2 CH 2 OH, or O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 33
Dependent Claim
31 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 COOC 6 H 11 O 5 and R 5 and R 6 are OCH 3 .
Claim 34
Dependent Claim
35 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 COOC 6 H 11 O 5 and R 5 and R 6 are OCH 2 CH 2 CH 2 OH.
Claim 35
Dependent Claim
33 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 COOC 6 H 11 O 5 and R 5 and R 6 are OCH 2 CH 2 OH.
Claim 36
Dependent Claim
58 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 COOC 6 H 11 O 5 and R 5 and R 6 are O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 37
Dependent Claim
34 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 COOC 6 H 11 O 5 and R 5 and R 6 are independently H or CH 3 .
Claim 38
Dependent Claim
82 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 COOC 6 H 11 O 5 , R 5 is CH 3 , and R 6 is H, CH 3 , OCH 3 , OCH 2 CH 2 OH, OCH 2 CH 2 CH 2 OH, or O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 .
Claim 39
Dependent Claim
60 words
The water-soluble compound of claim 1 wherein the oxyhydroxyalkyl is C.sub.(n-x) H.sub.((2n+1)-2x) O x O y or OC.sub.(n-x) H.sub.((2n+1)-2x) O x O y where n is a positive integer from 1 to 10; x is zero or a positive integer less than or equal to n; and y is zero or a positive integer less than or equal to ((2n+1)-2x).
Claim 40
Dependent Claim
196 words
The water soluble compound of claim 1 wherein the oxyhydroxyalkyl or saccharide is C n H.sub.((2n+1)-q) O y R a q , OC n H.sub.((2n+1)-q) O y R a q or (CH 2 ) n CO 2 R a where n is a positive integer from 1 to 10, y is zero or a positive integer less than ((2n+1)-q), q is zero or a positive integer less than or equal to 2n+1, R a is independently H, alkyl, hydroxyalkyl, saccharide, C.sub.(m-w) H.sub.((2m+1)-2w) O w O z , O 2 CC.sub.(m-w) H.sub.((2m+1)-2w) O w O z or N(R)OCC.sub.(m-w) H.sub.((2m+1)-2w) O w O z , where m is a positive integer from 1 to 10, w is zero or a positive integer less than or equal to m, z is zero or a positive integer less than or equal to ((2m+1)-2w), R is H alkyl hydroxyalkyl or C m H.sub.((2m+1)-r) O z R b r where m is a positive integer from 1 to 10, z is zero or a positive integer less than ((2m+1)-r), r is zero or a positive integer less than or equal to 2m+1, and R b is independently H, alkyl, hydroxyalkyl, or saccharide.
Claim 41
Dependent Claim
178 words
The water soluble compound of claim 1 wherein the carboxyamidealkyl is (CH 2 ) n CONHR a , O(CH 2 ) n CONHR a , (CH 2 ) n CON(R a ) 2 , or O(CH 2 ) n CON(R a ) 2 where n is a positive integer from 1 to 10, R a is independently H, alkyl, hydroxyalkyl, saccharide, C.sub.(m-w) H.sub.((2m+1)-2w) O w O z , O 2 CC.sub.(m-w) H.sub.((2m+1)-2w) O w O z or N(R) OCC.sub.(m-w) H.sub.((2m+1)-2w) O w O z , where m is a positive integer from 1 to 10, w is zero or a positive integer less than or equal to m, z is zero or a positive integer less than or equal to ((2m+1)-2w), R is H, alkyl, hydroxyalkyl, or C m H.sub.((2m+1)-r) O z R b r where m is a positive integer from 1 to 10, z is zero or a positive integer less than ((2m+1)-r), r is zero or a positive integer less than or equal to 2m+1, and R b is independently H, alkyl, hydroxyalkyl, or saccharide.
Claim 42
Dependent Claim
223 words
The water soluble compound of claim 1 wherein the carboxyalkyl is C n H.sub.((2n+1)-q) O y R c q or OC n H.sub.((2n+1)-q) O y R c q where n is a positive integer from 1 to 10; y is zero or a positive integer less than ((2n+1)-q), q is zero or a positive integer less than or equal to 2n+1, R c is (CH 2 ) n CO 2 R d , (CH 2 ) n CONHR d or (CH 2 ) n CON(R d ) 2 where n is a positive integer from 1 to 10; R d is independently H, alkyl, hydroxyalkyl, saccharide, C.sub.(m-w) H.sub.((2m+1)-2w) O w O z , O 2 CC.sub.(m-w) H.sub.((2m+1)-2 w) O w O z or N(R)OCC.sub.(m-w) H.sub.((2m+1)-2w) O w O z , where m is a positive integer from 1 to 10, w is zero or a positive integer less than or equal to m, z is zero or a positive integer less than or equal to ((2m+1)-2w), R is H, alkyl, hydroxyalkyl, or C m H.sub.((2m+1)-r) O z R b r where m is a positive integer from 1 to 10, z is zero or a positive integer less than ((2m+1)-r), r is zero or a positive integer less than or equal to 2m+1, and R b is independently H, alkyl, hydroxyalkyl, or saccharide.
Claim 43
Dependent Claim
44 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are O(CH 2 CH 2 O) 2 CH 2 CH 2 OR', where R' is H or CH 3 .
Claim 44
Dependent Claim
38 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are O(CH 2 CH 2 O) 2 CH 2 CH 2 OCH 3 .
Claim 45
Dependent Claim
17 words
The water soluble compound of claim 23 wherein n is 2 and R' is CH 3 .
Claim 46
Dependent Claim
16 words
The water soluble compound of claim 42, 43 or 44 wherein M is Gd +3 .
Claim 47
Dependent Claim
16 words
The water soluble compound of claim 42, 43 or 44 wherein M is Lu +3 .
Claim 48
Dependent Claim
34 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are OCH 2 COOH or OCH 2 CH 2 COOH.
Claim 49
Dependent Claim
66 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH and R 5 and R 6 are OCH 2 CH 2 CONHC(CH 2 OH) 3 ; OCH 2 CH 2 CH 2 NHCO[CH(OH)] 4 CH 2 OH; OCH 2 CH 2 C(CH 2 OH) 3 ; or OCH 2 CH 2 COOCH 2 C(CH 2 OH) 3 .
Claim 50
Dependent Claim
74 words
The water soluble compound of claim 1 wherein R 1 is CH 2 CH 2 CH 2 OH; R 5 is (O) m (CH 2 ) n CONHR, where m is zero or 1; n is zero, 1, 2, or 3; and R is an aminosugar, a polysaccharide, an oligosaccharide, or an oligopeptide; and R 6 is H, OH, OCH 3 , O(CH 2 ) 2 OH, O(CH 2 ) 3 OH, or COOH.
Claim 51
Dependent Claim
82 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH; R 5 is (O) m (CH 2 ) n CONHR, where m is zero or 1; n is zero, 1, 2, or 3; and R is glucosamine, galactosamine, mannosamine, poly-L-lysine, derivatized poly-L-lysine, (LysAla) n , (LysLeuAla) n , polyglutamic acid, polyornithine, or heparin; and R 6 is H, OH, OCH 3 , O(CH 2 ) 2 OH, O(CH 2 ) 3 OH, or COOH.
Claim 52
Dependent Claim
14 words
The water soluble compound of claim 49 or 50 where R 6 is H.
Claim 53
Dependent Claim
101 words
The water soluble compound of claim 1 were R 1 is CH 2 (CH 2 CH 2 O) n CH 2 CH 2 OR, where n is an integerless than or equal to 10 and R is H or CH 3 ; and R 5 and R 6 are OCH 3 , OCH 2 CH 2 OH; OCH 2 CH 2 CH 2 OH; O(CH 2 CH 2 O) n CH 2 CH 2 OR', where n is an integer less than or equal to 10 and R' is H or CH 3 ; or independently H or CH 3 .
Claim 54
Dependent Claim
21 words
The water soluble compound of claim 52 where R 5 and R 6 are OCH 2 CH 2 CH 2 OH.
Claim 55
Dependent Claim
66 words
The water soluble compound of claim 1 where R 1 is (CH 2 ) n CON(R')R, where n is 1, 2, or 3, R' is H or CH 3 , and R is an aminosugar, a polysaccharide, an oligosaccharide, or an oligopeptide; and R 5 and R 6 are CH 3 , OCH 3 , O(CH 2 ) 2 OH, or O(CH 2 ) 3 OH.
Claim 56
Dependent Claim
74 words
The water soluble compound of claim 1 where R 1 is O(CH 2 ) n CON(R')R, where n is 1, 2, or 3, R' is H or CH 3 , and R is glucosamine, galactosamine, mannosamine, poly-L-lysine, derivatized poly-L-lysine, (LysAla) n , (LysLeuAla) n , polyglutamic acid, polyornithine, or heparin; and R 5 and R 6 are CH 3 , OCH 3 , O(CH 2 ) 2 OH, or O(CH 2 ) 3 OH.
Claim 57
Dependent Claim
21 words
The water soluble compound of claim 1 where R 5 and R 6 are OCH 2 CH 2 OHCH 2 OH.
Claim 58
Dependent Claim
16 words
The water soluble compound of claim 23 wherein M is Mn +2 or Mn +3 .
Claim 59
Dependent Claim
16 words
The water soluble compound of claim 43 wherein M is Mn +2 or Mn +3 .
Claim 60
Dependent Claim
40 words
The water soluble compound of claim 1 where R 1 is CH 2 CH 2 CH 2 OH, R 5 and R 6 are OCH 2 CH 2 CH 2 OH, and M is Mn +2 or Mn +3 .
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1998-10-09 | 1999-04-10 | 1999-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2002-10-09 | 2003-04-10 | 2003-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2006-10-09 | 2007-04-10 | 2007-10-10 | $7700.00 | Window Closed / Lapsed |