CA2699773A1

CA2699773A1 - Methods and compounds for treating retinol-related diseases

Methods and compounds for treating retinol-related diseases Download PDF

Info

Publication number: CA2699773A1
Authority: CA; Canada
Prior art keywords: alkyl; compound; formula; optionally substituted; butyl
Prior art date: 2007-09-27
Legal status : Abandoned

Application number

CA2699773A

Other languages

English (en)

French (fr)

Inventor

Nathan L. Mata

Kim B. Phan

Tam V. Bui

Mustapha Haddach

Current Assignee

Sirion Therapeutics Inc

Original Assignee

Individual

Priority date

2007-09-27

Filing date

2008-09-16

Publication date

2009-04-02

2008-09-16 Application filed by Individual filed Critical Individual

2009-04-02 Publication of CA2699773A1 publication Critical patent/CA2699773A1/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 359
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 title claims abstract description 293
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 title claims abstract description 163
239000011607 retinol Substances 0.000 title claims abstract description 143
229960003471 retinol Drugs 0.000 title claims abstract description 143
238000000034 method Methods 0.000 title claims abstract description 131
235000020944 retinol Nutrition 0.000 title claims abstract description 128
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 60
201000010099 disease Diseases 0.000 title claims description 53
239000000203 mixture Substances 0.000 claims abstract description 118
208000002780 macular degeneration Diseases 0.000 claims abstract description 74
210000002966 serum Anatomy 0.000 claims abstract description 66
230000000007 visual effect Effects 0.000 claims abstract description 12
-1 methylenecyclopropyl Chemical group 0.000 claims description 176
108091000053 retinol binding Proteins 0.000 claims description 118
102000029752 retinol binding Human genes 0.000 claims description 118
125000000217 alkyl group Chemical group 0.000 claims description 115
241000124008 Mammalia Species 0.000 claims description 110
239000008194 pharmaceutical composition Substances 0.000 claims description 104
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 91
108010071690 Prealbumin Proteins 0.000 claims description 78
102000009190 Transthyretin Human genes 0.000 claims description 78
150000003839 salts Chemical class 0.000 claims description 76
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 68
239000000651 prodrug Substances 0.000 claims description 68
229940002612 prodrug Drugs 0.000 claims description 68
125000004404 heteroalkyl group Chemical group 0.000 claims description 65
239000002207 metabolite Substances 0.000 claims description 65
125000003342 alkenyl group Chemical group 0.000 claims description 63
125000001072 heteroaryl group Chemical group 0.000 claims description 63
239000012453 solvate Substances 0.000 claims description 61
125000003107 substituted aryl group Chemical group 0.000 claims description 59
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 57
230000000694 effects Effects 0.000 claims description 50
102100038246 Retinol-binding protein 4 Human genes 0.000 claims description 46
125000000753 cycloalkyl group Chemical group 0.000 claims description 46
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 45
125000005843 halogen group Chemical group 0.000 claims description 43
206010064930 age-related macular degeneration Diseases 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 39
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 39
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 38
230000027455 binding Effects 0.000 claims description 37
125000000392 cycloalkenyl group Chemical group 0.000 claims description 35
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 34
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 33
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
229910052760 oxygen Inorganic materials 0.000 claims description 31
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NCYCYZXNIZJOKI-IOUUIBBYSA-N 11-cis-retinal Chemical compound O=C/C=C(\C)/C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-IOUUIBBYSA-N 0.000 claims description 4
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OPGXIVOGSNQWAY-UHFFFAOYSA-N 3-[(2-tert-butyl-4-chlorophenoxy)methyl]cyclopentane-1-carboxylic acid Chemical compound CC(C)(C)C1=CC(Cl)=CC=C1OCC1CC(C(O)=O)CC1 OPGXIVOGSNQWAY-UHFFFAOYSA-N 0.000 claims description 4
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SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 claims description 3
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COBGWVGXUVRBBY-UHFFFAOYSA-N 2-[3-[(2-tert-butyl-4-chlorophenoxy)methyl]cyclopentyl]acetic acid Chemical compound CC(C)(C)C1=CC(Cl)=CC=C1OCC1CC(CC(O)=O)CC1 COBGWVGXUVRBBY-UHFFFAOYSA-N 0.000 claims description 2
HDUVFHYCOAXIEL-UHFFFAOYSA-N 3-[(2-tert-butyl-4-chloroanilino)methyl]cyclopentane-1-carboxamide Chemical compound CC(C)(C)C1=CC(Cl)=CC=C1NCC1CC(C(N)=O)CC1 HDUVFHYCOAXIEL-UHFFFAOYSA-N 0.000 claims description 2
WLNCCKQPRPEHGG-UHFFFAOYSA-N 4-(2-tert-butyl-4-chlorophenoxy)butanoic acid Chemical compound CC(C)(C)C1=CC(Cl)=CC=C1OCCCC(O)=O WLNCCKQPRPEHGG-UHFFFAOYSA-N 0.000 claims description 2
SKNPWISJZMCGMB-UHFFFAOYSA-N 4-[5-(2-tert-butyl-4-chlorophenoxy)pentanoylamino]benzamide Chemical compound CC(C)(C)C1=CC(Cl)=CC=C1OCCCCC(=O)NC1=CC=C(C(N)=O)C=C1 SKNPWISJZMCGMB-UHFFFAOYSA-N 0.000 claims description 2
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