ZA200304382B - Diaryl peptides as NS3-Serine protease inhibitors of hepatitis C virus. - Google Patents
Diaryl peptides as NS3-Serine protease inhibitors of hepatitis C virus. Download PDFInfo
- Publication number
- ZA200304382B ZA200304382B ZA200304382A ZA200304382A ZA200304382B ZA 200304382 B ZA200304382 B ZA 200304382B ZA 200304382 A ZA200304382 A ZA 200304382A ZA 200304382 A ZA200304382 A ZA 200304382A ZA 200304382 B ZA200304382 B ZA 200304382B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- compound
- aryl
- cycloalkyl
- compound according
- Prior art date
Links
- 241000711549 Hepacivirus C Species 0.000 title description 33
- 108090000765 processed proteins & peptides Proteins 0.000 title description 14
- 102000004196 processed proteins & peptides Human genes 0.000 title description 9
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 title description 3
- 239000003001 serine protease inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 124
- -1 enantiomers Chemical class 0.000 claims description 116
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 51
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
- 125000003118 aryl group Chemical group 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 37
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 19
- 125000005110 aryl thio group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 18
- 125000001769 aryl amino group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 108091005804 Peptidases Proteins 0.000 claims description 14
- 239000004365 Protease Substances 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 125000005281 alkyl ureido group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000004437 phosphorous atom Chemical group 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 241000700605 Viruses Species 0.000 claims description 13
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 13
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 12
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims description 11
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 10
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 10
- 229940079322 interferon Drugs 0.000 claims description 10
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 9
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000012453 solvate Substances 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 8
- 125000005518 carboxamido group Chemical group 0.000 claims description 8
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 102000014150 Interferons Human genes 0.000 claims description 7
- 108010050904 Interferons Proteins 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 7
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 6
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 5
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- 230000001747 exhibiting effect Effects 0.000 claims description 5
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 229960000329 ribavirin Drugs 0.000 claims description 4
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 4
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 101150026868 CHS1 gene Proteins 0.000 claims description 2
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 2
- 101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 2
- 150000004789 alkyl aryl sulfoxides Chemical class 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- 150000008378 aryl ethers Chemical class 0.000 claims description 2
- 125000005362 aryl sulfone group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 21
- 239000000126 substance Substances 0.000 claims 17
- 239000003937 drug carrier Substances 0.000 claims 7
- 239000003443 antiviral agent Substances 0.000 claims 6
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 3
- 238000007920 subcutaneous administration Methods 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 101100167365 Caenorhabditis elegans cha-1 gene Proteins 0.000 claims 1
- 241000984695 Troglodytinae Species 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 claims 1
- 101710144111 Non-structural protein 3 Proteins 0.000 description 15
- 102100038132 Endogenous retrovirus group K member 6 Pro protein Human genes 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 108010022999 Serine Proteases Proteins 0.000 description 10
- 102000012479 Serine Proteases Human genes 0.000 description 10
- 229920001184 polypeptide Polymers 0.000 description 6
- 208000005176 Hepatitis C Diseases 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 206010016654 Fibrosis Diseases 0.000 description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 3
- 230000007882 cirrhosis Effects 0.000 description 3
- 208000019425 cirrhosis of liver Diseases 0.000 description 3
- 208000006454 hepatitis Diseases 0.000 description 3
- 231100000283 hepatitis Toxicity 0.000 description 3
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 3
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 241000701022 Cytomegalovirus Species 0.000 description 2
- 241000709721 Hepatovirus A Species 0.000 description 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 2
- 108010076039 Polyproteins Proteins 0.000 description 2
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 description 2
- 125000000539 amino acid group Chemical group 0.000 description 2
- 208000029570 hepatitis D virus infection Diseases 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000029812 viral genome replication Effects 0.000 description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000053642 Catalytic RNA Human genes 0.000 description 1
- 108090000994 Catalytic RNA Proteins 0.000 description 1
- 108090000317 Chymotrypsin Proteins 0.000 description 1
- 101710091045 Envelope protein Proteins 0.000 description 1
- 108010088842 Fibrinolysin Proteins 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 208000005331 Hepatitis D Diseases 0.000 description 1
- 101000856199 Homo sapiens Chymotrypsin-like protease CTRL-1 Proteins 0.000 description 1
- 101001077660 Homo sapiens Serine protease inhibitor Kazal-type 1 Proteins 0.000 description 1
- 102000008394 Immunoglobulin Fragments Human genes 0.000 description 1
- 108010021625 Immunoglobulin Fragments Proteins 0.000 description 1
- 102100020870 La-related protein 6 Human genes 0.000 description 1
- 108050008265 La-related protein 6 Proteins 0.000 description 1
- 101100129514 Mus musculus Mbip gene Proteins 0.000 description 1
- 125000001429 N-terminal alpha-amino-acid group Chemical group 0.000 description 1
- 108090001074 Nucleocapsid Proteins Proteins 0.000 description 1
- 108010067372 Pancreatic elastase Proteins 0.000 description 1
- 102000016387 Pancreatic elastase Human genes 0.000 description 1
- 101710188315 Protein X Proteins 0.000 description 1
- 108010049219 RNA-dependent ATPase Proteins 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 108010067390 Viral Proteins Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229960002376 chymotrypsin Drugs 0.000 description 1
- 239000003541 chymotrypsin inhibitor Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 238000011461 current therapy Methods 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 241001493065 dsRNA viruses Species 0.000 description 1
- 102000057815 human SPINK1 Human genes 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 229960001322 trypsin Drugs 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
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
- C07K5/08—Tripeptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/81—Protease inhibitors
- C07K14/8107—Endopeptidase (E.C. 3.4.21-99) inhibitors
- C07K14/811—Serine protease (E.C. 3.4.21) inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25486900P | 2000-12-12 | 2000-12-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200304382B true ZA200304382B (en) | 2004-09-13 |
Family
ID=22965900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200304382A ZA200304382B (en) | 2000-12-12 | 2003-06-04 | Diaryl peptides as NS3-Serine protease inhibitors of hepatitis C virus. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6911428B2 (fr) |
| EP (1) | EP1343807B1 (fr) |
| JP (1) | JP4368581B2 (fr) |
| KR (1) | KR20030091946A (fr) |
| CN (1) | CN1301994C (fr) |
| AR (1) | AR031905A1 (fr) |
| AT (1) | ATE430166T1 (fr) |
| AU (2) | AU3659102A (fr) |
| CA (1) | CA2430458A1 (fr) |
| DE (1) | DE60138567D1 (fr) |
| ES (1) | ES2324594T3 (fr) |
| HK (1) | HK1054394B (fr) |
| HU (1) | HUP0303436A2 (fr) |
| IL (1) | IL155842A0 (fr) |
| MX (1) | MXPA03005219A (fr) |
| PE (1) | PE20020691A1 (fr) |
| WO (1) | WO2002048172A2 (fr) |
| ZA (1) | ZA200304382B (fr) |
Families Citing this family (168)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4080541B2 (ja) | 1996-10-18 | 2008-04-23 | バーテックス ファーマシューティカルズ インコーポレイテッド | セリンプロテアーゼ、特にｃ型肝炎ウイルスｎｓ３プロテアーゼの阻害因子 |
| SV2003000617A (es) | 2000-08-31 | 2003-01-13 | Lilly Co Eli | Inhibidores de la proteasa peptidomimetica ref. x-14912m |
| JP2005533817A (ja) | 2002-06-28 | 2005-11-10 | イデニクス（ケイマン）リミテツド | フラビウィルス科ウィルス感染治療用の修飾２′および３′−ヌクレオシドプロドラッグ |
| EP1408031A1 (fr) * | 2002-10-09 | 2004-04-14 | 3 D Gene Pharma | Derivés de pyrolidine comme médicaments contre Hepatitis C |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2012739T5 (es) | 1987-11-18 | 2001-12-01 | Chiron Corp | Diagnosticos para nanbv. |
| DE69024378T2 (de) | 1989-02-01 | 1996-09-12 | Asahi Glass Co Ltd | Azeotrope oder azeotropähnliche Zusammensetzung auf der Basis von Chlorfluorkohlenwasserstoffen |
| CA2079105C (fr) | 1990-04-04 | 2000-06-13 | Michael Houghton | Protease du virus de l'hepatite c |
| AU4156197A (en) | 1996-08-21 | 1998-03-06 | Hybridon, Inc. | Oligonucleotide prodrugs |
| JP4080541B2 (ja) | 1996-10-18 | 2008-04-23 | バーテックス ファーマシューティカルズ インコーポレイテッド | セリンプロテアーゼ、特にｃ型肝炎ウイルスｎｓ３プロテアーゼの阻害因子 |
| GB9623908D0 (en) | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
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| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
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| US7012066B2 (en) * | 2000-07-21 | 2006-03-14 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| CZ2003195A3 (cs) * | 2000-07-21 | 2003-04-16 | Schering Corporation | Peptidové inhibitory serinové proteázy NS3 a farmaceutický prostředek |
-
2001
- 2001-12-10 MX MXPA03005219A patent/MXPA03005219A/es active IP Right Grant
- 2001-12-10 KR KR10-2003-7007731A patent/KR20030091946A/ko not_active Application Discontinuation
- 2001-12-10 AR ARP010105721A patent/AR031905A1/es unknown
- 2001-12-10 ES ES01986126T patent/ES2324594T3/es not_active Expired - Lifetime
- 2001-12-10 HU HU0303436A patent/HUP0303436A2/hu unknown
- 2001-12-10 AT AT01986126T patent/ATE430166T1/de not_active IP Right Cessation
- 2001-12-10 DE DE60138567T patent/DE60138567D1/de not_active Expired - Lifetime
- 2001-12-10 US US10/013,071 patent/US6911428B2/en not_active Expired - Fee Related
- 2001-12-10 EP EP01986126A patent/EP1343807B1/fr not_active Expired - Lifetime
- 2001-12-10 AU AU3659102A patent/AU3659102A/xx active Pending
- 2001-12-10 AU AU2002236591A patent/AU2002236591B2/en not_active Expired - Fee Related
- 2001-12-10 IL IL15584201A patent/IL155842A0/xx unknown
- 2001-12-10 WO PCT/US2001/047383 patent/WO2002048172A2/fr active Application Filing
- 2001-12-10 CA CA002430458A patent/CA2430458A1/fr not_active Abandoned
- 2001-12-10 CN CNB018204759A patent/CN1301994C/zh not_active Expired - Fee Related
- 2001-12-10 JP JP2002549703A patent/JP4368581B2/ja not_active Expired - Fee Related
- 2001-12-11 PE PE2001001236A patent/PE20020691A1/es not_active Application Discontinuation
-
2003
- 2003-06-04 ZA ZA200304382A patent/ZA200304382B/en unknown
- 2003-09-18 HK HK03106692.5A patent/HK1054394B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004532812A (ja) | 2004-10-28 |
| EP1343807A2 (fr) | 2003-09-17 |
| PE20020691A1 (es) | 2002-08-03 |
| CN1301994C (zh) | 2007-02-28 |
| HUP0303436A2 (hu) | 2004-01-28 |
| DE60138567D1 (de) | 2009-06-10 |
| WO2002048172A2 (fr) | 2002-06-20 |
| AU2002236591B2 (en) | 2005-07-14 |
| AU3659102A (en) | 2002-06-24 |
| US20020147139A1 (en) | 2002-10-10 |
| JP4368581B2 (ja) | 2009-11-18 |
| ES2324594T3 (es) | 2009-08-11 |
| ATE430166T1 (de) | 2009-05-15 |
| MXPA03005219A (es) | 2003-09-25 |
| HK1054394A1 (en) | 2003-11-28 |
| AR031905A1 (es) | 2003-10-08 |
| KR20030091946A (ko) | 2003-12-03 |
| EP1343807B1 (fr) | 2009-04-29 |
| CN1501942A (zh) | 2004-06-02 |
| CA2430458A1 (fr) | 2002-06-20 |
| US6911428B2 (en) | 2005-06-28 |
| WO2002048172A3 (fr) | 2003-06-19 |
| HK1054394B (zh) | 2009-09-25 |
| IL155842A0 (en) | 2003-12-23 |
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