US2008009473A1PendingUtilityA1
Pyridyl-substituted porphyrin compounds and methods of use thereof
Assignee: INOTEK PHARMACEUTICALS CORPPriority: Mar 29, 2004Filed: Jul 19, 2007Published: Jan 10, 2008
Est. expiryMar 29, 2024(expired)· nominal 20-yr term from priority
A61P 9/06A61P 3/10A61P 37/00A61P 39/06A61P 9/04A61P 9/10A61P 39/00A61P 9/00A61P 43/00A61P 31/04A61P 25/28A61P 25/16A61P 25/14A61P 31/10A61P 29/00A61P 27/02A61P 35/02A61P 35/00A61P 25/00A61P 15/10A61P 1/00C07F 15/025A61P 1/02A61P 11/00A61P 17/16A61P 17/02C07D 487/22A61P 17/06A61P 19/02C07F 11/005C07F 13/005A61P 17/00A61P 1/16A61K 31/44
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Claims
Abstract
The present invention relates to Pyridyl-Substituted Porphyrin Compounds, compositions comprising an effective amount of a Pyridyl-Substituted Porphyrin Compound and methods for treating or preventing injury due to exposure to a reactive species, erectile dysfunction due to surgery, lung disease, hyperoxia, neurodegenerative disease, liver disease, myocardial damage during cardioplegia, an inflammatory condition, a reperfusion injury, an ischemic condition, a cardiovascular disease, diabetes, a diabetic complication, cancer, a side effect of cancer chemotherapy, or a radiation-induced injury, or to prolong the half-life of an oxidation-prone compound, comprising administering to a subject in need thereof an effective amount of a Pyridyl-Substituted Porphyrin Compound.
Claims
exact text as granted — not AI-modified1 . A method for treating an inflammatory condition, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
2 . The method of claim 1 , wherein the compound of formula (A) has the structure:
3 . The method of claim 1 , wherein the inflammatory condition is an inflammatory condition of a joint, a chronic inflammatory condition of the gum, an inflammatory bowel disease, an inflammatory lung disease, an inflammatory condition of the central nervous system, an inflammatory condition of the eye, gram-positive shock, gram negative shock, hemorrhagic shock, anaphylactic shock, traumatic shock, chemotherapeutic shock, or shock induced in response to administration of a pro-inflammatory cytokine.
4 . The method of claim 2 , wherein the inflammatory condition is an inflammatory condition of a joint, a chronic inflammatory condition of the gum, an inflammatory bowel disease, an inflammatory lung disease, an inflammatory condition of the central nervous system, an inflammatory condition of the eye, gram-positive shock, gram negative shock, hemorrhagic shock, anaphylactic shock, traumatic shock chemotherapeutic shock, or shock induced in response to administration of a pro-inflammatory cytokine.
5 . A method for treating a reperfusion injury, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
6 . The method of claim 5 , wherein the compound of formula (A) has the structure:
7 . The method of claim 5 , wherein the reperfusion injury is stroke, myocardial infarction, or a reoxygenation injury resulting from organ transplantation.
8 . The method of claim 6 , wherein the reperfusion injury is stroke, myocardial infarction, or a reoxygenation injury resulting from organ transplantation.
9 . The method of claim 7 , wherein the organ transplantation is cardiac transplantation or kidney transplantation.
10 . The method of claim 8 , wherein the organ transplantation is cardiac transplantation or kidney transplantation.
11 . A method for treating an ischemic condition, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
12 . The method of claim 11 , wherein the compound of formula (A) has the structure:
13 . The method of claim 11 , wherein the ischemic condition is myocardial ischemia, stable angina, unstable angina, stroke, ischemic heart disease or cerebral ischemia.
14 . The method of claim 12 , wherein the ischemic condition is myocardial ischemia, stable angina, unstable angina, stroke, ischemic heart disease or cerebral ischemia.
15 . A method for treating a radiation-induced injury, the method comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
16 . The method of claim 15 , wherein the compound of formula (A) has the structure:
17 . The method of claim 15 , wherein the radiation-induced injury is acute radiation sickness.
18 . The method of claim 16 , wherein the radiation-induced injury is acute radiation sickness.
19 . A method for treating diabetes, the method comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
20 . The method of claim 19 , wherein the compound of formula (A) has the structure:
21 . The method of claim 19 , wherein the diabetes is diabetes mellitus.
22 . The method of claim 20 , wherein the diabetes is diabetes mellitus.
23 . The method of claim 19 , wherein the diabetes is Type I diabetes or Type II diabetes.
24 . The method of claim 20 , wherein the diabetes is Type I diabetes or Type II diabetes.
25 . A method for treating a diabetic complication, the method comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
26 . The method of claim 25 , wherein the compound of formula (A) has the structure:
27 . The method of claim 25 , wherein the diabetic complication is diabetic neuropathy, retinopathy, neuropathy, angiopathy, cardiomyopathy, or erectile dysfunction.
28 . The method of claim 26 , wherein the diabetic complication is diabetic neuropathy, retinopathy, neuropathy, angiopathy, cardiomyopathy, or erectile dysfunction.
29 . A method for treating a cardiovascular disease, the method comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
30 . The method of claim 29 , wherein the compound of formula (A) has the structure:
31 . The method of claim 29 , wherein the cardiovascular disease is acute heart failure, chronic heart failure, ischemic heart failure, drug-induced heart failure, idiopathic heart failure, alcoholic heart failure, or a cardiac arrhythmia.
32 . The method of claim 30 , wherein the cardiovascular disease is acute heart failure, chronic heart failure, ischemic heart failure, drug-induced heart failure, idiopathic heart failure, alcoholic heart failure, or a cardiac arrhythmia.
33 . The method of claim 29 , wherein the cardiovascular disease is balloon-induced vascular injury, coronary stenting, atherosclerosis, or restenosis.
34 . The method of claim 30 , wherein the cardiovascular disease is balloon-induced vascular injury, coronary stenting, atherosclerosis, or restenosis.
35 . A method for treating cancer, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
36 . The method of claim 35 , wherein the compound of formula (A) has the structure:
37 . The method of claim 35 , wherein the cancer is colorectal cancer, lung cancer, pancreatic cancer, esophageal cancer, stomach cancer, skin cancer, leukemia, lymphoma, testicular cancer, bladder cancer, breast cancer, prostate cancer, head and neck cancer or ovarian cancer.
38 . The method of claim 36 , wherein the cancer is colorectal cancer, lung cancer, pancreatic cancer, esophageal cancer, stomach cancer, skin cancer, leukemia, lymphoma, testicular cancer, bladder cancer, breast cancer, prostate cancer, head and neck cancer or ovarian cancer.
39 . A method for treating a side effect of cancer chemotherapy, comprising administering to a subject in need thereof an effective amount of a compound having the formula
(A)
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
40 . The method of claim 39 , wherein the compound of formula (A) has the structure:
41 . The method of claim 39 , wherein the cancer chemotherapy comprises administering a platinum-based chemotherapy agent to the subject.
42 . The method of claim 40 , wherein the cancer chemotherapy comprises administering a platinum-based chemotherapy agent to the subject.
43 . The method of claim 41 , wherein the platinum-based chemotherapy agent is cisplatin.
44 . The method of claim 42 , wherein the platinum-based chemotherapy agent is cisplatin.
45 . The method of claim 15 , wherein the radiation-induced injury is caused by radiation therapy administered to a subject for the treatment of cancer.
46 . The method of claim 16 , wherein the radiation-induced injury is caused by radiation therapy administered to a subject for the treatment of cancer.
47 . A method for preventing radiation-induced death, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
48 . The method of claim 47 , wherein the compound of formula (A) has the structure:
49 . A method for increasing a subject's survival time following exposure to radiation, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
50 . The method of claim 49 , wherein the compound of formula (A) has the structure:
51 . A method for treating or preventing injury due to exposure to a reactive species, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
52 . The method of claim 51 , wherein the compound of formula (A) has the structure:
53 . A method for treating or preventing an inflammatory skin disease, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
54 . The method of claim 53 , wherein the compound of formula (A) has the structure:
55 . The method of claim 53 , wherein the inflammatory skin disease is contact dermatitis, erythema, or psoriasis.
56 . The method of claim 54 , wherein the inflammatory skin disease is contact dermatitis, erythema, or psoriasis.
57 . A method for treating or preventing skin wrinkling, skin aging, sunburn erythema, UV-induced skin injury, or UV-induced skin disease, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
58 . The method of claim 57 , wherein the compound of formula (A) has the structure:
59 . A method of treating or preventing erectile dysfunction caused by surgery, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
60 . The method of claim 59 , wherein the compound of formula (A) has the structure:
61 . The method of claim 59 , wherein the surgery is surgery of the prostate or the colon.
62 . The method of claim 60 , wherein the surgery is surgery of the prostate or the colon.
63 . A method for treating or preventing a lung disease, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
64 . The method of claim 63 , wherein the compound of formula (A) has the structure:
65 . The method of claim 63 , wherein the lung disease is cystic fibrosis, hyperoxic lung injury, emphysema, or adult respiratory distress syndrome.
66 . The method of claim 64 , wherein the lung disease is cystic fibrosis, hyperoxic lung injury, emphysema, or adult respiratory distress syndrome.
67 . A method for treating or preventing injury due to hyperoxia, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
68 . The method of claim 67 , wherein the compound of formula (A) has the structure:
69 . The method of claim 67 , wherein the injury due to hyperoxia is hyperoxia-induced eye injury or hyperoxia-induced lung injury.
70 . The method of claim 68 , wherein the injury due to hyperoxia is hyperoxia-induced eye injury or hyperoxia-induced lung injury.
71 . A method for treating or preventing a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
72 . The method of claim 71 , wherein the compound of formula (A) has the structure:
73 . The method of claim 71 , wherein the neurodegenerative disease is Parkinson's disease, Alzheimer's disease, Huntington's disease, or amyotrophic lateral sclerosis.
74 . The method of claim 72 , wherein the neurodegenerative disease is Parkinson's disease, Alzheimer's disease, Huntington's disease, or amyotrophic lateral sclerosis.
75 . A method for treating or preventing a liver disease, comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
76 . The method of claim 75 , wherein the compound of formula (A) has the structure:
77 . The method of claim 75 , wherein the liver disease is hepatitis, liver failure, or drug-induced liver injury.
78 . The method of claim 76 , wherein the liver disease is hepatitis, liver failure, or drug-induced liver injury.
79 . A method for inducing cardioplegia comprising administering to a subject in need thereof an effective amount of a cardioplegia-inducing agent and a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
80 . The method of claim 79 , wherein the compound of formula (A) has the structure:
81 . A method for prolonging the half-life of an oxidation-prone compound in vivo comprising administering to a subject in need thereof an effective amount of a compound having the formula
wherein:
M is Fe or Mn;
f is 0 or 1;
each R is independently —C(O)OH or —C(O)O − ;
each X − is independently a negatively-charged counterion; and
n=(f)+(the total number of R groups where R is —C(O)OH).
82 . The method of claim 81 , wherein the compound of formula (A) has the structure:Join the waitlist — get patent alerts
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