CA2785185C - Organic compounds for the regulation of vectorial ion channels - Google Patents
Organic compounds for the regulation of vectorial ion channels Download PDFInfo
- Publication number
- CA2785185C CA2785185C CA2785185A CA2785185A CA2785185C CA 2785185 C CA2785185 C CA 2785185C CA 2785185 A CA2785185 A CA 2785185A CA 2785185 A CA2785185 A CA 2785185A CA 2785185 C CA2785185 C CA 2785185C
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- Canada
- Prior art keywords
- cndot
- compound
- amino acid
- amino
- lung
- Prior art date
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- 102000004310 Ion Channels Human genes 0.000 title claims abstract description 31
- 230000033228 biological regulation Effects 0.000 title claims abstract description 18
- 150000002894 organic compounds Chemical class 0.000 title description 4
- 150000001413 amino acids Chemical class 0.000 claims abstract description 79
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 38
- 125000003277 amino group Chemical group 0.000 claims abstract description 31
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 18
- 206010030113 Oedema Diseases 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 230000004199 lung function Effects 0.000 claims abstract description 11
- -1 cyclic organic compound Chemical class 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 117
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 72
- 239000004471 Glycine Substances 0.000 claims description 46
- 210000004899 c-terminal region Anatomy 0.000 claims description 25
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 210000004072 lung Anatomy 0.000 claims description 18
- 206010037423 Pulmonary oedema Diseases 0.000 claims description 13
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 12
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 11
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 11
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 9
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 9
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 9
- 229960003104 ornithine Drugs 0.000 claims description 9
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 claims description 8
- 208000004852 Lung Injury Diseases 0.000 claims description 8
- 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 claims description 8
- 231100000515 lung injury Toxicity 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 6
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 206010069351 acute lung injury Diseases 0.000 claims description 6
- 229960002684 aminocaproic acid Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 230000029058 respiratory gaseous exchange Effects 0.000 claims description 6
- 208000009421 viral pneumonia Diseases 0.000 claims description 5
- 108010002350 Interleukin-2 Proteins 0.000 claims description 4
- 208000019693 Lung disease Diseases 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 206010022000 influenza Diseases 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 208000034486 Multi-organ failure Diseases 0.000 claims description 3
- 206010061603 Respiratory syncytial virus infection Diseases 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000000872 buffer Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims description 3
- 230000003204 osmotic effect Effects 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007884 disintegrant Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000000796 flavoring agent Substances 0.000 claims description 2
- 235000013355 food flavoring agent Nutrition 0.000 claims description 2
- 235000003599 food sweetener Nutrition 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 239000003765 sweetening agent Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 9
- 230000008569 process Effects 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 56
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 28
- 229910052799 carbon Inorganic materials 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 108090000765 processed proteins & peptides Proteins 0.000 description 27
- 235000001014 amino acid Nutrition 0.000 description 24
- 108090000862 Ion Channels Proteins 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 22
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 20
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 125000001433 C-terminal amino-acid group Chemical group 0.000 description 12
- 239000012530 fluid Substances 0.000 description 12
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 11
- 238000005259 measurement Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 9
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 8
- 238000010532 solid phase synthesis reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000012453 solvate Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 102000004196 processed proteins & peptides Human genes 0.000 description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 5
- 239000004472 Lysine Substances 0.000 description 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 102000003837 Epithelial Sodium Channels Human genes 0.000 description 4
- 108090000140 Epithelial Sodium Channels Proteins 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 238000001994 activation Methods 0.000 description 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 4
- 235000003704 aspartic acid Nutrition 0.000 description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 235000013922 glutamic acid Nutrition 0.000 description 4
- 239000004220 glutamic acid Substances 0.000 description 4
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- 238000004113 cell culture Methods 0.000 description 3
- 210000002919 epithelial cell Anatomy 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 230000037427 ion transport Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 210000003456 pulmonary alveoli Anatomy 0.000 description 3
- 230000032258 transport Effects 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical compound CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 2
- 102000010637 Aquaporins Human genes 0.000 description 2
- 239000007995 HEPES buffer Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000035508 accumulation Effects 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 2
- 229960002576 amiloride Drugs 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 210000003050 axon Anatomy 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 210000005260 human cell Anatomy 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VZQHRKZCAZCACO-PYJNHQTQSA-N (2s)-2-[[(2s)-2-[2-[[(2s)-2-[[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]propanoyl]amino]prop-2-enoylamino]-3-methylbutanoyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C(C)C)NC(=O)C(=C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCCNC(N)=N VZQHRKZCAZCACO-PYJNHQTQSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 206010015866 Extravasation Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 108010052164 Sodium Channels Proteins 0.000 description 1
- 102000018674 Sodium Channels Human genes 0.000 description 1
- 102000018594 Tumour necrosis factor Human genes 0.000 description 1
- 108050007852 Tumour necrosis factor Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 230000036251 extravasation Effects 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000002102 hyperpolarization Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 230000007483 microbial process Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical group O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 230000008816 organ damage Effects 0.000 description 1
- 230000007331 pathological accumulation Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- XWIJIXWOZCRYEL-UHFFFAOYSA-M potassium;methanesulfonate Chemical compound [K+].CS([O-])(=O)=O XWIJIXWOZCRYEL-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000036412 respiratory physiology Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/52—Cytokines; Lymphokines; Interferons
- C07K14/525—Tumour necrosis factor [TNF]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/56—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation not occurring through 2,4-diamino-butanoic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/191—Tumor necrosis factors [TNF], e.g. lymphotoxin [LT], i.e. TNF-beta
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Gastroenterology & Hepatology (AREA)
- Pulmonology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0004110A AT509267A1 (de) | 2010-01-14 | 2010-01-14 | Organische verbindungen zur regulierung von vektoriellen ionenkanälen |
| ATA41/2010 | 2010-01-14 | ||
| PCT/AT2011/000014 WO2011085423A1 (de) | 2010-01-14 | 2011-01-12 | Zyklische peptide zur regulierung von vektoriellen ionenkanälen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2785185A1 CA2785185A1 (en) | 2011-07-21 |
| CA2785185C true CA2785185C (en) | 2019-02-19 |
Family
ID=43970939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2785185A Active CA2785185C (en) | 2010-01-14 | 2011-01-12 | Organic compounds for the regulation of vectorial ion channels |
Country Status (16)
| Country | Link |
|---|---|
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| WO (1) | WO2011085423A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2679239A1 (de) | 2012-06-28 | 2014-01-01 | Apeptico Forschung und Entwicklung GmbH | Pharmazeutische Zusammensetzung zur Behandlung der durch Sauerstoffarmut und verringerten Luftdruck vermittelten pulmonalen Form der Höhenkrankheit |
| JP6335279B2 (ja) * | 2013-04-23 | 2018-05-30 | アペプティコ フオルシユング ウント アントウィクラング ゲーエムベーハー | 式ｘ１−ｇｑｒｅｔｐｅｇａｅａｋｐｗｙ−ｘ２の環状ペプチドを含んでなる医薬組成物および体外肺処置のための使用 |
| US12004506B2 (en) | 2013-04-23 | 2024-06-11 | Apeptico Forschung Und Entwicklung Gmbh | Pharmaceutical composition comprising a cyclic peptide of formula X1-GQRETPEGAEAKPWY-X2 and use for extracorporeal lung treatment |
| DK2988768T3 (da) * | 2013-04-23 | 2021-06-21 | Apeptico Forschung & Entwicklung Gmbh | Lyofilisat indeholdende et cyklisk peptid med Formel X1-GQRETPEGAEAKPWY-X2 til behandling af pulmonære ødemer |
| WO2015132294A1 (en) * | 2014-03-04 | 2015-09-11 | Apeptico Forschung Und Entwicklung Gmbh | Attenuation of intrapulmonary inflammation |
| CN108025038B (zh) * | 2015-09-14 | 2022-02-01 | 阿佩普蒂科研究和开发有限责任公司 | 治疗1b型pha的环状多肽 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5968753A (en) * | 1994-06-14 | 1999-10-19 | Nexell Therapeutics, Inc. | Positive and positive/negative cell selection mediated by peptide release |
| NZ509604A (en) | 1998-08-14 | 2003-05-30 | Innogenetics N | TNF-derived peptides for use in treating oedema |
| FR2839514A1 (fr) * | 2002-05-07 | 2003-11-14 | Centre Nat Rech Scient | Nouveaux peptides cycliques, leur utilisation comme agents anti-microbiens |
| EP1781323B1 (en) | 2004-08-06 | 2010-02-17 | Nycomed GmbH | Composition comprising a pulmonary surfactant and a tnf-derived peptide |
| CN101003520A (zh) * | 2007-01-12 | 2007-07-25 | 陈志龙 | 一种缬氨酸丁酰联苯化合物 |
| CN101007791A (zh) * | 2007-01-12 | 2007-08-01 | 东华大学 | 一种氨基酸联苯化合物 |
| EP2009023A1 (en) * | 2007-06-04 | 2008-12-31 | Rentschler Beteiligungs GmbH | Novel peptides and their use for the treatment of edema |
| AT506151B1 (de) * | 2007-12-12 | 2010-01-15 | Apeptico Forschung Und Entwick | Fusionsprotein |
| AT506150B1 (de) * | 2007-12-12 | 2010-01-15 | Apeptico Forschung Und Entwick | Zyklisches und cystein-freies peptid |
| CN101298432B (zh) * | 2008-05-30 | 2010-12-22 | 广州市星业科技发展有限公司 | L-吡咯烷酮羧酸钠的制备方法 |
| WO2009149278A1 (en) * | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| AT507953B1 (de) * | 2009-03-05 | 2011-02-15 | Apeptico Forschung & Entwicklung Gmbh | Verfahren zur vermeidung und zur behandlung einer hyperpermeabilität |
| DK2397151T3 (en) * | 2010-06-21 | 2015-05-18 | Apeptico Forschung & Entwicklung Gmbh | The treatment of the vascular complications of diabetes |
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2010
- 2010-01-14 AT AT0004110A patent/AT509267A1/de not_active Application Discontinuation
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2011
- 2011-01-12 WO PCT/AT2011/000014 patent/WO2011085423A1/de not_active Ceased
- 2011-01-12 CA CA2785185A patent/CA2785185C/en active Active
- 2011-01-12 PL PL11705798T patent/PL2523968T3/pl unknown
- 2011-01-12 BR BR112012017093A patent/BR112012017093A2/pt not_active IP Right Cessation
- 2011-01-12 ES ES11705798.4T patent/ES2525381T3/es active Active
- 2011-01-12 EP EP11705798.4A patent/EP2523968B1/de active Active
- 2011-01-12 DK DK11705798.4T patent/DK2523968T3/da active
- 2011-01-12 AU AU2011206907A patent/AU2011206907B2/en not_active Ceased
- 2011-01-12 US US13/522,204 patent/US8754049B2/en active Active
- 2011-01-12 NZ NZ600818A patent/NZ600818A/en not_active IP Right Cessation
- 2011-01-12 KR KR1020127018445A patent/KR101865420B1/ko active Active
- 2011-01-12 CN CN201180005765.9A patent/CN102770442B/zh active Active
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- 2011-01-12 RU RU2012134322/04A patent/RU2538597C2/ru not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2523968A1 (de) | 2012-11-21 |
| JP2013517224A (ja) | 2013-05-16 |
| EP2523968B1 (de) | 2014-09-10 |
| ES2525381T3 (es) | 2014-12-23 |
| AU2011206907B2 (en) | 2016-06-02 |
| HK1174341A1 (en) | 2013-06-07 |
| WO2011085423A1 (de) | 2011-07-21 |
| RU2012134322A (ru) | 2014-02-20 |
| US20130072444A1 (en) | 2013-03-21 |
| CA2785185A1 (en) | 2011-07-21 |
| IL220924B (en) | 2018-04-30 |
| AT509267A1 (de) | 2011-07-15 |
| AU2011206907A1 (en) | 2012-06-21 |
| CN102770442B (zh) | 2015-09-23 |
| CN102770442A (zh) | 2012-11-07 |
| RU2538597C2 (ru) | 2015-01-10 |
| BR112012017093A2 (pt) | 2016-11-29 |
| NZ600818A (en) | 2014-02-28 |
| DK2523968T3 (da) | 2014-11-03 |
| PL2523968T3 (pl) | 2015-03-31 |
| KR20120134100A (ko) | 2012-12-11 |
| JP5771220B2 (ja) | 2015-08-26 |
| US8754049B2 (en) | 2014-06-17 |
| KR101865420B1 (ko) | 2018-07-13 |
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| EEER | Examination request |
Effective date: 20160106 |