TW201408702A - 環孢素ａ類似物 - Google Patents

Info

Publication number

TW201408702A

TW201408702A TW102119527A TW102119527A TW201408702A TW 201408702 A TW201408702 A TW 201408702A TW 102119527 A TW102119527 A TW 102119527A TW 102119527 A TW102119527 A TW 102119527A TW 201408702 A TW201408702 A TW 201408702A

Authority

TW

Taiwan

Prior art keywords

methyl

compound

methylamino

sar

cyclosporin

Prior art date

2012-06-01

Links

• Espacenet
• Global Dossier
• Discuss

• PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical class CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 title claims abstract description 507
• 238000000034 method Methods 0.000 claims abstract description 139
• 208000003556 Dry Eye Syndromes Diseases 0.000 claims abstract description 60
• 206010013774 Dry eye Diseases 0.000 claims abstract description 47
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 45
• 239000000203 mixture Substances 0.000 claims abstract description 40
• 150000001875 compounds Chemical class 0.000 claims description 560
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 337
• 108010036949 Cyclosporine Proteins 0.000 claims description 333
• 229930105110 Cyclosporin A Natural products 0.000 claims description 330
• 229960001265 ciclosporin Drugs 0.000 claims description 310
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 164
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 122
• 125000000623 heterocyclic group Chemical group 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 84
• -1 N-methylpiperazinyl Chemical group 0.000 claims description 55
• 206010061218 Inflammation Diseases 0.000 claims description 46
• 230000004054 inflammatory process Effects 0.000 claims description 46
• 229910052760 oxygen Inorganic materials 0.000 claims description 41
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 35
• 239000000243 solution Substances 0.000 claims description 29
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 150000001412 amines Chemical class 0.000 claims description 25
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
• 208000024891 symptom Diseases 0.000 claims description 24
• 206010023332 keratitis Diseases 0.000 claims description 23
• 201000010666 keratoconjunctivitis Diseases 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 18
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
• 150000001299 aldehydes Chemical class 0.000 claims description 17
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 238000001356 surgical procedure Methods 0.000 claims description 15
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• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 12
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• 201000010099 disease Diseases 0.000 claims description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
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• 125000005842 heteroatom Chemical group 0.000 claims description 9
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• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
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• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 6
• 238000003756 stirring Methods 0.000 claims description 6
• 230000009885 systemic effect Effects 0.000 claims description 6
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• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
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• ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims description 5
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
• 125000001188 haloalkyl group Chemical group 0.000 claims description 5
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• 206010052779 Transplant rejections Diseases 0.000 claims description 4
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
• 239000007864 aqueous solution Substances 0.000 claims description 4
• GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 4
• 231100000321 erythema Toxicity 0.000 claims description 4
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 claims description 4
• ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 claims description 4
• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
• 125000006239 protecting group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
• 231100000241 scar Toxicity 0.000 claims description 4
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 206010072139 Ocular rosacea Diseases 0.000 claims description 3
• 206010042033 Stevens-Johnson syndrome Diseases 0.000 claims description 3
• 231100000168 Stevens-Johnson syndrome Toxicity 0.000 claims description 3
• 108010021119 Trichosanthin Proteins 0.000 claims description 3
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• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 238000001914 filtration Methods 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 239000012528 membrane Substances 0.000 claims description 3
• YWWNNLPSZSEZNZ-UHFFFAOYSA-N n,n-dimethyldecan-1-amine Chemical compound CCCCCCCCCCN(C)C YWWNNLPSZSEZNZ-UHFFFAOYSA-N 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
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• 125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 2
• DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims description 2
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 2
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• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 2
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• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
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