CA2603404A1 - Substituted 1,2-ethylendiamines, medicaments comprising said compound; their use and their method of manufacture - Google Patents
Substituted 1,2-ethylendiamines, medicaments comprising said compound; their use and their method of manufacture Download PDFInfo
- Publication number
- CA2603404A1 CA2603404A1 CA002603404A CA2603404A CA2603404A1 CA 2603404 A1 CA2603404 A1 CA 2603404A1 CA 002603404 A CA002603404 A CA 002603404A CA 2603404 A CA2603404 A CA 2603404A CA 2603404 A1 CA2603404 A1 CA 2603404A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- heteroaryl
- heterocyclyl
- cycloalkyl
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims description 191
- 238000000034 method Methods 0.000 title claims description 45
- 239000003814 drug Chemical class 0.000 title claims description 12
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000004519 manufacturing process Methods 0.000 title description 5
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 764
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 389
- -1 carboxy, formyl Chemical group 0.000 claims description 221
- 229910052731 fluorine Inorganic materials 0.000 claims description 187
- 239000011737 fluorine Substances 0.000 claims description 185
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 184
- 239000000460 chlorine Substances 0.000 claims description 173
- 229910052801 chlorine Inorganic materials 0.000 claims description 168
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 167
- 229910052794 bromium Inorganic materials 0.000 claims description 155
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 153
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 153
- 125000001072 heteroaryl group Chemical group 0.000 claims description 131
- 125000000623 heterocyclic group Chemical group 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 122
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 120
- 239000001257 hydrogen Substances 0.000 claims description 118
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 96
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 92
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 76
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 67
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 66
- 229910052717 sulfur Inorganic materials 0.000 claims description 58
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 56
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 45
- 239000013543 active substance Substances 0.000 claims description 43
- 125000004043 oxo group Chemical group O=* 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000001153 fluoro group Chemical group F* 0.000 claims description 30
- 125000004434 sulfur atom Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
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- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 19
- 230000002401 inhibitory effect Effects 0.000 claims description 18
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
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- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 230000002265 prevention Effects 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 10
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 10
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 10
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 10
- 239000000969 carrier Substances 0.000 claims description 9
- 238000012545 processing Methods 0.000 claims description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 8
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- 108090000258 Cathepsin D Proteins 0.000 claims description 8
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 201000008319 inclusion body myositis Diseases 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- 230000002159 abnormal effect Effects 0.000 claims description 7
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- 230000003551 muscarinic effect Effects 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims description 5
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 5
- DUGMCDWNXXFHDE-VZYDHVRKSA-N 2-amino-2-methyl-n-[(2r)-1-(1-methylsulfonylspiro[2h-indole-3,4'-piperidine]-1'-yl)-1-oxo-3-phenylmethoxypropan-2-yl]propanamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.C([C@@H](NC(=O)C(C)(N)C)C(=O)N1CCC2(C3=CC=CC=C3N(C2)S(C)(=O)=O)CC1)OCC1=CC=CC=C1 DUGMCDWNXXFHDE-VZYDHVRKSA-N 0.000 claims description 5
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 claims description 5
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- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- KVLLHLWBPNCVNR-SKCUWOTOSA-N capromorelin Chemical compound C([C@@]12CN(CCC1=NN(C2=O)C)C(=O)[C@@H](COCC=1C=CC=CC=1)NC(=O)C(C)(C)N)C1=CC=CC=C1 KVLLHLWBPNCVNR-SKCUWOTOSA-N 0.000 claims description 5
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- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims description 5
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 5
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 5
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- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LDKDMDVMMCXTMO-LBPRGKRZSA-N tert-butyl n-[(2s)-1-hydroxy-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](CO)CC1=CC=CC=C1 LDKDMDVMMCXTMO-LBPRGKRZSA-N 0.000 description 1
- LQTMEOSBXTVYRM-VIFPVBQESA-N tert-butyl n-[(2s)-1-hydroxy-4-methylpentan-2-yl]carbamate Chemical compound CC(C)C[C@@H](CO)NC(=O)OC(C)(C)C LQTMEOSBXTVYRM-VIFPVBQESA-N 0.000 description 1
- XWZWRKLKABZPGP-VIFPVBQESA-N tert-butyl n-[(2s)-1-oxo-3-thiophen-2-ylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C=O)CC1=CC=CS1 XWZWRKLKABZPGP-VIFPVBQESA-N 0.000 description 1
- WSVQQQWSUDALOR-JTQLQIEISA-N tert-butyl n-[(2s)-1-oxo-3-thiophen-3-ylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C=O)CC=1C=CSC=1 WSVQQQWSUDALOR-JTQLQIEISA-N 0.000 description 1
- CVXUYYULENWBTP-NSHDSACASA-N tert-butyl n-cyclohexyl-n-[(2s)-1-oxopropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N([C@H](C=O)C)C1CCCCC1 CVXUYYULENWBTP-NSHDSACASA-N 0.000 description 1
- NWISIXHXJZTEJZ-JTQLQIEISA-N tert-butyl n-cyclopentyl-n-[(2s)-1-oxopropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N([C@H](C=O)C)C1CCCC1 NWISIXHXJZTEJZ-JTQLQIEISA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- 239000012096 transfection reagent Substances 0.000 description 1
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05006939.2 | 2005-03-30 | ||
| EP05006939 | 2005-03-30 | ||
| PCT/EP2006/002769 WO2006103038A1 (en) | 2005-03-30 | 2006-03-27 | Substituted 1,2-ethylendiamines, medicaments comprising said compound; their use and their method of manufacture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2603404A1 true CA2603404A1 (en) | 2006-10-05 |
Family
ID=36545049
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002603404A Abandoned CA2603404A1 (en) | 2005-03-30 | 2006-03-27 | Substituted 1,2-ethylendiamines, medicaments comprising said compound; their use and their method of manufacture |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US7713961B2 (enExample) |
| EP (1) | EP1866034A1 (enExample) |
| JP (1) | JP2008534541A (enExample) |
| AR (1) | AR056862A1 (enExample) |
| CA (1) | CA2603404A1 (enExample) |
| TW (1) | TW200716152A (enExample) |
| WO (1) | WO2006103038A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2603404A1 (en) * | 2005-03-30 | 2006-10-05 | Boehringer Ingelheim International Gmbh | Substituted 1,2-ethylendiamines, medicaments comprising said compound; their use and their method of manufacture |
| JP2009503027A (ja) * | 2005-08-03 | 2009-01-29 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | アルツハイマー病ｉｉの治療のための置換エタン−１，２−ジアミン |
| EP1919861A2 (de) * | 2005-08-11 | 2008-05-14 | Boehringer Ingelheim International GmbH | Verbindungen zur behandlung der alzheimer erkrankung |
| US20090042867A1 (en) * | 2005-08-11 | 2009-02-12 | Klaus Fuchs | Compounds for the treatment of alzheimer's disease |
| EP1915339A1 (de) * | 2005-08-11 | 2008-04-30 | Boehringer Ingelheim International GmbH | Inhibitoren der beta-sekretase zur behandlung der alzheimer- erkrankung |
| CA2618474A1 (en) * | 2005-08-11 | 2007-02-15 | Boehringer Ingelheim International Gmbh | Compounds for treating alzheimer's disease |
| JP2012505241A (ja) | 2008-10-10 | 2012-03-01 | パーデュー・リサーチ・ファウンデーション | アルツハイマー病の治療用組成物 |
| EP2376083A4 (en) | 2008-11-20 | 2012-06-20 | Purdue Research Foundation | QUINAZOLIN-BASED BACE-1 INHIBITORS AND METHODS OF USE |
| WO2010065861A2 (en) * | 2008-12-05 | 2010-06-10 | Purdue Research Foundation | Inhibitors of bace 1 and methods for treating alzheimer's disease |
| JP2013506713A (ja) * | 2009-10-05 | 2013-02-28 | コメンティス，インコーポレーテッド | β−セクレターゼ活性を阻害するスルホンアミドピロリジン化合物及びその使用方法 |
| US20140066488A1 (en) * | 2012-08-30 | 2014-03-06 | Purdue Research Foundation | Inhibitors of Memapsin 2 Cleavage for the Treatment of Alzheimer's Disease |
| US20240383852A1 (en) * | 2021-03-12 | 2024-11-21 | Infex Therapeutics Limited | Anti-viral compounds |
| MX2023014754A (es) | 2021-06-18 | 2024-02-12 | Aligos Therapeutics Inc | Métodos y composiciones dirigidos a pd-l1. |
| CN119212987A (zh) | 2021-12-16 | 2024-12-27 | 安力高医药股份有限公司 | 用于靶向pd-l1的方法和组合物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ184194A3 (en) | 1993-08-09 | 1995-03-15 | Lilly Co Eli | Aspartylprotease inhibitor and method of identifying thereof |
| US7087399B1 (en) | 1999-05-13 | 2006-08-08 | Scios, Inc. | β-secretase and modulation of β-secretase activity |
| EP1194449B1 (en) | 1999-06-28 | 2010-09-22 | Oklahoma Medical Research Foundation | Inhibitors of memapsin 2 and use thereof |
| CA2449948A1 (en) * | 2001-06-08 | 2002-12-19 | Elan Pharmaceuticals, Inc. | Methods of treating alzheimer's disease |
| EP1453516A2 (de) | 2001-10-17 | 2004-09-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | 5-substituierte 4-amino-2-phenylamino-pyrimdinderivate und ihre verwendung als beta-amyloid modulatoren |
| AU2003206413A1 (en) * | 2002-01-04 | 2003-07-24 | Elan Pharmaceuticals, Inc. | Substituted amino carboxamides for the treatment of alzheimer's disease |
| US7763646B2 (en) * | 2002-09-27 | 2010-07-27 | Elan Pharmaceuticals, Inc. | Compounds for the treatment of alzheimer's disease |
| DE60329316D1 (de) * | 2002-11-12 | 2009-10-29 | Merck & Co Inc | Phenylcarboxamide als beta-sekretase-hemmer zur behandlung von alzheimer |
| US20050090449A1 (en) | 2003-05-13 | 2005-04-28 | Boehringer Ingelheim International Gmbh | Novel statine derivatives for the treatment of Alzheimer's disease |
| JP2007516207A (ja) * | 2003-06-30 | 2007-06-21 | メルク エンド カムパニー インコーポレーテッド | アルツハイマー病の治療のためのＮ−アルキルフェニルカルボキサミドβ−セクレターゼ阻害剤 |
| EP1750719A2 (en) | 2004-05-19 | 2007-02-14 | Boehringer Ingelheim International GmbH | Treatment of diseases associated with altered level of amyloid beta peptides |
| WO2005113582A1 (en) | 2004-05-22 | 2005-12-01 | Boehringer Ingelheim International Gmbh | Substituted ethane-1,2-diamines for the treatment of alzheimer's disease |
| WO2006050861A2 (en) | 2004-11-10 | 2006-05-18 | Boehringer Ingelheim International Gmbh | Statine derivatives for the treatment of alzheimer's disease |
| WO2006050862A1 (en) | 2004-11-10 | 2006-05-18 | Boehringer Ingelheim International Gmbh | Statine derivatives for the treatment of alzheimer's disease |
| CA2603404A1 (en) * | 2005-03-30 | 2006-10-05 | Boehringer Ingelheim International Gmbh | Substituted 1,2-ethylendiamines, medicaments comprising said compound; their use and their method of manufacture |
| JP2009503027A (ja) | 2005-08-03 | 2009-01-29 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | アルツハイマー病ｉｉの治療のための置換エタン−１，２−ジアミン |
| US20090042867A1 (en) | 2005-08-11 | 2009-02-12 | Klaus Fuchs | Compounds for the treatment of alzheimer's disease |
-
2006
- 2006-03-27 CA CA002603404A patent/CA2603404A1/en not_active Abandoned
- 2006-03-27 EP EP06723747A patent/EP1866034A1/en not_active Withdrawn
- 2006-03-27 JP JP2008503415A patent/JP2008534541A/ja active Pending
- 2006-03-27 WO PCT/EP2006/002769 patent/WO2006103038A1/en not_active Ceased
- 2006-03-29 TW TW095110860A patent/TW200716152A/zh unknown
- 2006-03-29 AR ARP060101206A patent/AR056862A1/es not_active Application Discontinuation
- 2006-03-30 US US11/278,059 patent/US7713961B2/en active Active
-
2009
- 2009-07-29 US US12/511,474 patent/US20090325940A1/en not_active Abandoned
-
2010
- 2010-04-13 US US12/759,167 patent/US20100204160A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1866034A1 (en) | 2007-12-19 |
| US7713961B2 (en) | 2010-05-11 |
| US20060223759A1 (en) | 2006-10-05 |
| WO2006103038A1 (en) | 2006-10-05 |
| AR056862A1 (es) | 2007-10-31 |
| US20090325940A1 (en) | 2009-12-31 |
| US20100204160A1 (en) | 2010-08-12 |
| TW200716152A (en) | 2007-05-01 |
| JP2008534541A (ja) | 2008-08-28 |
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