US2002114769A1PendingUtilityA1
Novel dequalinium analogs
Priority: Sep 14, 2000Filed: Sep 14, 2001Published: Aug 22, 2002
Est. expirySep 14, 2020(expired)· nominal 20-yr term from priority
A61Q 17/04A61K 8/492A61Q 17/00
40
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Claims
Abstract
A chemical compound having the formula: (Q—L—Q) w +2 X y −z or (Q—T) u + X −v wherein: Q represents 4-E-2-R 3 -1-quinolinium; E represents NR 1 R 2 , COO R 1 , OR 1 , I, Br, Cl, F, or NO 3 N represents a nitrogen atom; R 1 and R 2 independently represent hydrogen or lower alkyl; R 3 represents E, hydrogen or lower alkyl; L represents a chain comprising n atoms, the atoms in the chain being t carbon atoms and 0 to approximately 0.5t heteroatoms; the minimum value of n is 12; the maximum value of n is 22; T represents hydrogen or a chain comprising m atoms, the atoms in the chain being t carbon atoms and 0 to approximately 0.5t heteroatoms; the minimum value of m is 6; the maximum value of m is 22; X represents an anion; w represents 1 or 3, y and z represent 1 or 2, with the proviso that 2w=yz; and u and v represent 1, 2, or 3 with the proviso that u=v.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A chemical compound having the formula:
(Q—L—Q) w +2 X y −z or (Q—T) u + X −v
wherein:
Q represents 4-E-2-R 3 -1-quinolinium;
E represents NR 1 R 2 , COO R 1 , OR 1 , I, Br, Cl, F, or NO 3 N represents a nitrogen atom;
R 1 and R 2 independently represent hydrogen or lower alkyl;
R 3 represents E, hydrogen or lower alkyl;
L represents a chain comprising n atoms, the atoms in the chain being t carbon atoms and 0 to approximately 0.5t heteroatoms;
the minimum value of n is 12;
the maximum value of n is 22;
T represents hydrogen or a chain comprising m atoms, the atoms in the chain being t carbon atoms and 0 to approximately 0.5t heteroatoms;
the minimum value of m is 6;
the maximum value of m is 22;
X represents an anion;
w represents 1 or 3, y and z represent 1 or 2, with the proviso that 2w=yz; and
u and v represent 1, 2, or 3 with the proviso that u=v.
2 . The chemical compound of claim 1 wherein E represents NR 1 R 2 .
3 . The chemical compound of claim 1 wherein R 3 represents hydrogen or lower alkyl.
4 . The chemical compound of claim 1 wherein E represents NR 1 R 2 and R 3 represents hydrogen or lower alkyl.
5 . The chemical compound of claim 1 having the formula:
(Q—L—Q) w +2 X y −z .
6 . The chemical compound of claim 1 having the formula:
(Q—L—Q) +2 X y −z or (Q—T) + X 1
wherein:
Q represents 4—NR 1 R 2 -2-R 3 -1-quinolinium;
N represents a nitrogen atom;
R 1 and R 2 independently represent hydrogen or lower alkyl;
R 3 represents hydrogen or lower alkyl;
L represents a 1,n-aliphatic chain comprising n carbon atoms;
n represents 6-22;
T represents hydrogen or a 1,m-aliphatic chain comprising m carbon atoms;
m represents 6-22;
X represents an anion; and
y and z represent 1 or 2 with the proviso that yz=2.
7 . The chemical compound of claim 5 wherein the heteroatoms are oxygen, sulfur, or nitrogen atoms.
8 . The chemical compound of claim 7 wherein L comprises at least one unit of ethylene glycol.
9 . The chemical compound of claim 7 wherein L comprises at least one unit of ethylenediamine.
10 . The chemical compound of claim 1 having the formula:
(Q—T) u + X −v .
11 . The chemical compound of claim 10 wherein:
u and v=1;
T represents hydrogen or a 1,m-aliphatic chain comprising m carbon atoms;
and X represents nitrate, sulfate, bisulfate, or halide.
12 . The chemical compound of claim 10 wherein the heteroatoms are oxygen, sulfur, or nitrogen atoms.
13 . The chemical compound of claim 12 wherein T comprises at least one unit of ethylene glycol.
14 . The chemical compound of claim 12 wherein T comprises at least one unit of ethylenediamine.
15 . The chemical compound of claim 5 wherein L represents a saturated aliphatic chain.
16 . The chemical compound of claim 5 wherein L represents an unsaturated aliphatic chain.
17 . The chemical compound of claim 16 wherein the unsaturated aliphatic chain comprises at least one double bond.
18 . The chemical compound of claim 17 wherein the at least one double bond is a trans double bond.
19 . The chemical compound of claim 16 wherein the unsaturated aliphatic chain comprises at least one triple bond.
20 . The chemical compound of claim 5 wherein n represents 12-16.
21 . The chemical compound of claim 5 wherein n represents 14-16.
22 . The chemical compound of claim 5 wherein n represents 14.
23 . The chemical compound of claim 10 wherein m represents 8-18.
24 . The chemical compound of claim 10 wherein m represents 10-16.
25 . The chemical compound of claim 10 wherein m represents 12-14.
26 . The chemical compound of claim 5 wherein y represents 2.
27 . The chemical compound of claim 26 wherein X represents a halide.
28 . The chemical compound of claim 26 wherein X represents iodide.
29 . The chemical compound of claim 5 wherein R 1 and R 2 represent a hydrogen atom.
30 . The chemical compound of claim 5 wherein R 3 represent a methyl group.
31 . The chemical compound of claim 5 wherein (Q—L—Q) +2 represents 1,1′-(1,14-tetradecanediyl)-bis(4-amino-2-methylquinolinium)
32 . The chemical compound of claim 31 wherein X y −z represents diiodide.
33 . A composition for protecting human skin from harmful effects of the sun, the composition comprising a topically effective amount of:
(a) a first chemical compound that absorbs ultraviolet light sufficiently to reduce significantly the damage to human skin from harmful effects of ultraviolet light; and (b) a second chemical compound according to claim 1
34 . The composition of claim 33 wherein the second compound has the formula:
(Q—L—Q) w +2 X y −z .
35 . The composition of claim 33 wherein the second compound has the formula:
(Q—L—Q) +2 X y −z or (Q—T) + X 1
wherein:
Q represents 4-NR 1 R 2 -2-R 3 -1-quinolinium;
N represents a nitrogen atom;
R 1 and R 2 independently represent hydrogen or lower alkyl;
R 3 represents hydrogen or lower alkyl;
L represents a 1,n-aliphatic chain comprising n carbon atoms;
n represents 6-22;
T represents hydrogen or a 1,m-aliphatic chain comprising m carbon atoms;
m represents 6-22;
X represents an anion; and
y and z represent 1 or 2 with the proviso that yz=2.
36 . The composition of claim 33 wherein E represents NR 1 R 2 .
37 . The composition of claim 33 wherein R 3 represents hydrogen or lower alkyl.
38 . The composition of claim 33 wherein E represents NR 1 R 2 and R 3 represents hydrogen or lower alkyl.
39 . The composition of claim 35 wherein the heteroatoms are oxygen, sulfur, or nitrogen atoms.
40 . The composition of claim 39 wherein L comprises at least one unit of ethylene glycol.
41 . The composition of claim 39 wherein L comprises at least one unit of ethylenediamine.
42 . The composition of claim 33 wherein the second compound has the formula:
(Q—T) u + X −v .
43 . The composition of claim 42 wherein:
u and v=1;
T represents hydrogen or a 1,m-aliphatic chain comprising m carbon atoms;
and X represents nitrate, sulfate, bisulfate, or halide.
44 . The composition of claim 42 wherein the heteroatoms are oxygen, sulfur, or nitrogen atoms.
45 . The composition of claim 44 wherein T comprises at least one unit of ethylene glycol.
46 . The composition of claim 44 wherein T comprises at least one unit of ethylenediamine.
47 . The composition of claim 35 wherein L represents a saturated aliphatic chain.
48 . The composition of claim 35 wherein L represents an unsaturated aliphatic chain.
49 . The composition of claim 48 wherein the unsaturated aliphatic chain comprises at least one double bond.
50 . The composition of claim 49 wherein the at least one double bond is a trans double bond.
51 . The composition of claim 48 wherein the unsaturated aliphatic chain comprises at least one triple bond.
52 . The composition of claim 35 wherein n represents 12-16.
53 . The composition of claim 35 wherein n represents 14-16.
54 . The composition of claim 35 wherein n represents 14.
55 . The composition of claim 42 wherein m represents 8-18.
56 . The composition of claim 42 wherein m represents 10-16.
57 . The composition of claim 42 wherein m represents 12-14.
58 . The composition of claim 35 wherein y represents 2.
59 . The composition of claim 58 wherein X represents a halide.
60 . The composition of claim 58 wherein X represents iodide.
61 . The composition of claim 34 wherein R 1 and R 2 represent a hydrogen atom.
62 . The composition of claim 34 wherein R 3 represent a methyl group.
63 . The composition of claim 35 wherein (Q—L—Q) +2 represents 1,1′-(1,14-tetradecanediyl)-bis(4-amino-2-methylquinolinium)
64 . The composition of claim 63 wherein X y −z represents diiodide.
65 . A method for inhibiting the activity of an isoform of protein kinase C, the method comprising contacting the protein kinase C with an effective amount of a chemical compound according to claim 1 .
66 . The method according to claim 65 , wherein the isoform of protein kinase C is protein kinase Cα.
67 . The method according to claim 65 , further comprising subjecting the protein kinase C and the chemical compound according to claim 1 to a wavelength of ultraviolet light that enhances the inhibition.
68 . The method according to claim 67 wherein the wavelength of ultraviolet light is approximately 325 to 395 nm.
69 . The method according to claim 67 wherein the wavelength of ultraviolet light is approximately 365 nm.
70 . The method according to claim 65 , wherein the effective amount is a concentration of 0.05 to 1 uM.
71 . The method according to claim 70 , wherein the effective amount is a concentration of 200 to 300 nM.
72 . A method for inhibiting the motility of cells, the method comprising contacting the cells with an effective amount of a chemical compound according to claim 1 .
73 . The method according to claim 72 , wherein the cells are malignant cells.
74 . The method according to claim 72 , wherein the cells are melanoma cells, malignant breast, prostate, lung, uterus, kidney, or colon cells; any of the above cells in a pre-cancerous condition; and cells pre-disposed to become any of the above cells.
75 . The method according to claim 72 , wherein the malignant cells are melanoma cells, malignant breast, prostate, lung, uterus, kidney, or colon cells.
76 . The method according to claim 73 , wherein the malignant cells are melanoma cells.
77 . The method according to claim 73 , wherein the malignant cells are human breast cells.
78 . The method according to claim 73 , wherein the malignant cells are in vivo.
79 . The method according to claim 72 , further comprising subjecting the protein kinase C and the chemical compound according to claim 1 to a wavelength of ultraviolet light that enhances the inhibition of motility.
80 . The method according to claim 79 wherein the wavelength of ultraviolet light is approximately 325 to 395 nm.
81 . The method according to claim 79 wherein the wavelength of ultraviolet light is approximately 365 nm.
82 . The method according to claim 72 , wherein the effective amount is a concentration of 0.05 to 1 uM.
83 . The method according to claim 72 , wherein the effective amount is a concentration of 200 to 300 nM.
84 . A method for inhibiting the metastasis of malignant cells in a mammal, the method comprising treating the mammal with an effective amount of a chemical compound according to claim 1 .
85 . The method according to claim 84 , wherein the malignant cells are melanoma cells.
86 . The method according to claim 84 , wherein the malignant cells are human breast cells.
87 . The method according to claim 84 , wherein the malignant cells are melanoma cells, malignant breast, prostate, lung, uterus, kidney, or colon cells
88 . The method according to claim 84 , further comprising subjecting the cells and the chemical compound according to claim 1 to a wavelength of ultraviolet light that enhances the inhibition of metastasis.
89 . The method according to claim 67 wherein the wavelength of ultraviolet light is approximately 325 to 395 nm.
90 . The method according to claim 88 wherein the wavelength of ultraviolet light is approximately 365 nm.
91 . The method according to claim 88 , wherein the cells are accessible to external radiation.
92 . The method according to claim 88 , wherein the cells are skin cells.
93 . The method according to claim 84 , wherein the effective amount is a minimum of approximately 0.5 mg/kg body weight and a maximum of approximately 50 mg/kg body weight of the mammal.
94 . The method according to claim 84 , wherein the effective amount is approximately 5 mg/kg body weight of the mammal.
95 . The method according to claim 84 , wherein the blood level of the compound according to claim 1 is approximately 0.05 to approximately 1 uM.
96 . The method according to claim 95 , wherein the blood level is approximately 200 to 300 nM.
97 . The method according to claim 84 , wherein the mammal is a human.
98 . The method according to claim 84 , wherein the chemical compound according to claim 1 is administered topically, intravenously, or intraperitoneally.
99 . A method for inhibiting the growth of pre-cancerous or malignant cells in a mammal, the method comprising treating the mammal with an effective amount of a chemical compound according to claim 1 .
100 . The method for inhibiting the growth of pre-cancerous cells according to claim E, wherein the pre-cancerous cells are pre-cancerous skin lesions.
101 . The method for inhibiting the growth of malignant cells according to claim 99 , wherein the malignant cells are melanoma cells.
102 . The method for inhibiting the growth of malignant cells according to claim 99 , wherein the malignant cells are human breast cells.
103 . The method according to claim 99 , further comprising subjecting the cells and the chemical compound according to claim 1 to a wavelength of ultraviolet light that enhances the inhibition of metastasis.
104 . The method according to claim 103 wherein the wavelength of ultraviolet light is approximately 325 to 395 nm.
105 . The method according to claim 103 wherein the wavelength of ultraviolet light is approximately 365 nm.
106 . The method according to claim 99 , wherein the effective amount is a minimum of approximately 0.5 mg/kg body weight and a maximum of approximately 50 mg/kg body weight of the mammal.
107 . The method according to claim 99 , wherein the effective amount is approximately 5 mg/kg body weight of the mammal.
108 . The method according to claim 99 , wherein the blood level of the compound according to claim 1 is approximately 0.05 to 1 uM.
109 . The method according to claim 108 , wherein the blood level is approximately 200 to 300 nM.
110 . The method according to claim 99 , wherein the mammal is a human.
111 . The method according to claim 99 , wherein the chemical compound according to claim 1 is administered topically, intravenously, or intraperitoneally.Join the waitlist — get patent alerts
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