DK1854477T3 - Peptide inhibitors of plasma kallikrein for use in the treatment of eye disorders - Google Patents

Info

Publication number

DK1854477T3

DK1854477T3 DK07005182.6T DK07005182T DK1854477T3 DK 1854477 T3 DK1854477 T3 DK 1854477T3 DK 07005182 T DK07005182 T DK 07005182T DK 1854477 T3 DK1854477 T3 DK 1854477T3

Authority

DK

Denmark

Prior art keywords

phe

cys

glu

gly

ala

Prior art date

2006-03-16

Links

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• 108090000765 processed proteins & peptides Proteins 0.000 title claims description 82
• 238000011282 treatment Methods 0.000 title claims description 27
• 208000030533 eye disease Diseases 0.000 title claims description 23
• 108090000113 Plasma Kallikrein Proteins 0.000 title claims description 14
• 102000003827 Plasma Kallikrein Human genes 0.000 title claims description 13
• 239000003112 inhibitor Substances 0.000 title description 23
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• 108010012581 phenylalanylglutamate Proteins 0.000 claims description 166
• 150000001413 amino acids Chemical group 0.000 claims description 163
• 108010017949 tyrosyl-glycyl-glycine Proteins 0.000 claims description 141
• LTAWNJXSRUCFAN-UNQGMJICSA-N Phe-Thr-Arg Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O LTAWNJXSRUCFAN-UNQGMJICSA-N 0.000 claims description 140
• IDEODOAVGCMUQV-GUBZILKMSA-N Glu-Ser-Leu Chemical compound [H]N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(O)=O IDEODOAVGCMUQV-GUBZILKMSA-N 0.000 claims description 125
• IDOGEHIWMJMAHT-BYPYZUCNSA-N Gly-Gly-Cys Chemical compound NCC(=O)NCC(=O)N[C@@H](CS)C(O)=O IDOGEHIWMJMAHT-BYPYZUCNSA-N 0.000 claims description 125
• NUSWUSKZRCGFEX-FXQIFTODSA-N Glu-Glu-Cys Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CS)C(O)=O NUSWUSKZRCGFEX-FXQIFTODSA-N 0.000 claims description 123
• UDPSLLFHOLGXBY-FXQIFTODSA-N Cys-Glu-Glu Chemical compound [H]N[C@@H](CS)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(O)=O UDPSLLFHOLGXBY-FXQIFTODSA-N 0.000 claims description 115
• YWEHYKGJWHPGPY-XGEHTFHBSA-N Cys-Thr-Arg Chemical compound C[C@H]([C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)[C@H](CS)N)O YWEHYKGJWHPGPY-XGEHTFHBSA-N 0.000 claims description 111
• ZOLXQKZHYOHHMD-DLOVCJGASA-N Cys-Ala-Phe Chemical compound C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)NC(=O)[C@H](CS)N ZOLXQKZHYOHHMD-DLOVCJGASA-N 0.000 claims description 107
• IAYPZSHNZQHQNO-KKUMJFAQSA-N His-Ser-Phe Chemical compound C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC2=CN=CN2)N IAYPZSHNZQHQNO-KKUMJFAQSA-N 0.000 claims description 107
• 239000000203 mixture Substances 0.000 claims description 106
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• 108010016616 cysteinylglycine Proteins 0.000 claims description 85
• 108010065135 phenylalanyl-phenylalanyl-phenylalanine Proteins 0.000 claims description 85
• XNMYNGDKJNOKHH-BZSNNMDCSA-N Phe-Ser-Tyr Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(O)=O XNMYNGDKJNOKHH-BZSNNMDCSA-N 0.000 claims description 80
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 75
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• 108010027345 wheylin-1 peptide Proteins 0.000 claims description 68
• FADYJNXDPBKVCA-UHFFFAOYSA-N L-Phenylalanyl-L-lysin Natural products NCCCCC(C(O)=O)NC(=O)C(N)CC1=CC=CC=C1 FADYJNXDPBKVCA-UHFFFAOYSA-N 0.000 claims description 64
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• BKIFWLQFOOKUCA-DCAQKATOSA-N Met-His-Ser Chemical compound CSCC[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@@H](CO)C(=O)O)N BKIFWLQFOOKUCA-DCAQKATOSA-N 0.000 claims description 63
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• 108010041407 alanylaspartic acid Proteins 0.000 claims description 47
• MNBHKGYCLBUIBC-UFYCRDLUSA-N Arg-Phe-Phe Chemical compound C([C@H](NC(=O)[C@H](CCCNC(N)=N)N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 MNBHKGYCLBUIBC-UFYCRDLUSA-N 0.000 claims description 46
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• 108010073025 phenylalanylphenylalanine Proteins 0.000 claims description 37
• 108010084264 glycyl-glycyl-cysteine Proteins 0.000 claims description 36
• LOVIQNMIPQVIGT-BVSLBCMMSA-N Arg-Trp-Phe Chemical compound C([C@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCCN=C(N)N)N)C(O)=O)C1=CC=CC=C1 LOVIQNMIPQVIGT-BVSLBCMMSA-N 0.000 claims description 34
• CEXINUGNTZFNRY-BYPYZUCNSA-N Gly-Cys-Gly Chemical compound [NH3+]CC(=O)N[C@@H](CS)C(=O)NCC([O-])=O CEXINUGNTZFNRY-BYPYZUCNSA-N 0.000 claims description 31
• 108010047857 aspartylglycine Proteins 0.000 claims description 31
• FHXGMDRKJHKLKW-QWRGUYRKSA-N Ser-Tyr-Gly Chemical compound OC[C@H](N)C(=O)N[C@H](C(=O)NCC(O)=O)CC1=CC=C(O)C=C1 FHXGMDRKJHKLKW-QWRGUYRKSA-N 0.000 claims description 30
• 108010051242 phenylalanylserine Proteins 0.000 claims description 29
• 102000004196 processed proteins & peptides Human genes 0.000 claims description 24
• NUZHSNLQJDYSRW-BZSNNMDCSA-N Pro-Arg-Trp Chemical compound [H]N1CCC[C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O NUZHSNLQJDYSRW-BZSNNMDCSA-N 0.000 claims description 22
• 230000002207 retinal effect Effects 0.000 claims description 21
• HUUOZYZWNCXTFK-INTQDDNPSA-N Ala-His-Pro Chemical compound C[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)N2CCC[C@@H]2C(=O)O)N HUUOZYZWNCXTFK-INTQDDNPSA-N 0.000 claims description 20
• 208000004644 retinal vein occlusion Diseases 0.000 claims description 20
• KIEPQOIQHFKQLK-PCBIJLKTSA-N Phe-Asn-Ile Chemical compound [H]N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(O)=O KIEPQOIQHFKQLK-PCBIJLKTSA-N 0.000 claims description 19
• 201000010099 disease Diseases 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
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• CBENHWCORLVGEQ-HJOGWXRNSA-N Phe-Phe-Phe Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1 CBENHWCORLVGEQ-HJOGWXRNSA-N 0.000 claims description 17
• HIINQLBHPIQYHN-JTQLQIEISA-N Tyr-Gly-Gly Chemical compound OC(=O)CNC(=O)CNC(=O)[C@@H](N)CC1=CC=C(O)C=C1 HIINQLBHPIQYHN-JTQLQIEISA-N 0.000 claims description 17
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• JQLQUPIYYJXZLJ-ZEWNOJEFSA-N Phe-Ile-Tyr Chemical compound C([C@H](N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(O)=O)C1=CC=CC=C1 JQLQUPIYYJXZLJ-ZEWNOJEFSA-N 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 16
• 108010004914 prolylarginine Proteins 0.000 claims description 16
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• BOMYCJXTWRMKJA-RNXOBYDBSA-N Trp-Phe-Phe Chemical compound C1=CC=C(C=C1)C[C@@H](C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)N BOMYCJXTWRMKJA-RNXOBYDBSA-N 0.000 claims description 15
• VEPIBPGLTLPBDW-URLPEUOOSA-N Ile-Phe-Thr Chemical compound CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H]([C@@H](C)O)C(=O)O)N VEPIBPGLTLPBDW-URLPEUOOSA-N 0.000 claims description 14
• 206010025415 Macular oedema Diseases 0.000 claims description 14
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• 201000010230 macular retinal edema Diseases 0.000 claims description 14
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