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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
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 (es) |
EP (1) | EP1343807B1 (es) |
JP (1) | JP4368581B2 (es) |
KR (1) | KR20030091946A (es) |
CN (1) | CN1301994C (es) |
AR (1) | AR031905A1 (es) |
AT (1) | ATE430166T1 (es) |
AU (2) | AU3659102A (es) |
CA (1) | CA2430458A1 (es) |
DE (1) | DE60138567D1 (es) |
ES (1) | ES2324594T3 (es) |
HK (1) | HK1054394B (es) |
HU (1) | HUP0303436A2 (es) |
IL (1) | IL155842A0 (es) |
MX (1) | MXPA03005219A (es) |
PE (1) | PE20020691A1 (es) |
WO (1) | WO2002048172A2 (es) |
ZA (1) | ZA200304382B (es) |
Families Citing this family (168)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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EP3083654A1 (en) | 2013-12-18 | 2016-10-26 | Idenix Pharmaceuticals LLC | 4'-or nucleosides for the treatment of hcv |
US10449210B2 (en) | 2014-02-13 | 2019-10-22 | Ligand Pharmaceuticals Inc. | Prodrug compounds and their uses |
US20170135990A1 (en) | 2014-03-05 | 2017-05-18 | Idenix Pharmaceuticals Llc | Pharmaceutical compositions comprising a 5,5-fused heteroarylene flaviviridae inhibitor and their use for treating or preventing flaviviridae infection |
US20170066795A1 (en) | 2014-03-05 | 2017-03-09 | Idenix Pharmaceuticals Llc | Solid prodrug forms of 2'-chloro-2'-methyl uridine for hcv |
US20170066779A1 (en) | 2014-03-05 | 2017-03-09 | Idenix Pharmaceuticals Llc | Solid forms of a flaviviridae virus inhibitor compound and salts thereof |
EP3131914B1 (en) | 2014-04-16 | 2023-05-10 | Idenix Pharmaceuticals LLC | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
CN106687118A (zh) | 2014-07-02 | 2017-05-17 | 配体药物公司 | 前药化合物及其用途 |
CN105153005A (zh) * | 2015-08-05 | 2015-12-16 | 上海瑞博化学有限公司 | 一种4-羰基-脯氨酸衍生物的制备方法 |
EP3512836A1 (en) * | 2016-09-13 | 2019-07-24 | Haplogen GmbH | Antiviral compounds |
US11970482B2 (en) | 2018-01-09 | 2024-04-30 | Ligand Pharmaceuticals Inc. | Acetal compounds and therapeutic uses thereof |
Family Cites Families (11)
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., Tokio/Tokyo | Azeotrope oder azeotropähnliche Zusammensetzung auf der Basis von Chlorfluorkohlenwasserstoffen |
CA2079105C (en) | 1990-04-04 | 2000-06-13 | Michael Houghton | Hepatitis c virus protease |
AU4156197A (en) | 1996-08-21 | 1998-03-06 | Hybridon, Inc. | Oligonucleotide prodrugs |
IL129407A0 (en) * | 1996-10-18 | 2000-02-17 | Vertex Pharma | Inhibitors of serine proteases particularly hepatitis C virus NS3 protease pharmaceutical compositions containing the same and the use thereof |
GB9623908D0 (en) | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
AR022061A1 (es) | 1998-08-10 | 2002-09-04 | Boehringer Ingelheim Ca Ltd | Peptidos inhibidores de la hepatitis c, una composicion farmaceutica que los contiene, el uso de los mismos para preparar una composicion farmaceutica, el uso de un producto intermedio para la preparacion de estos peptidos y un procedimiento para la preparacion de un peptido analogo de los mismos. |
US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
CZ20023473A3 (cs) * | 2000-04-19 | 2003-01-15 | Schering Corporation | Makrocyklická sloučenina a farmaceutický prostředek |
RU2355700C9 (ru) * | 2000-07-21 | 2010-03-20 | Шеринг Корпорейшн | Новые пептиды как ингибиторы ns3-серинпротеазы вируса гепатита с |
BR0112666A (pt) * | 2000-07-21 | 2003-06-10 | Schering Corp | Peptìdeos como inibidores de ns3-serina protease de vìrus da hepatite c |
-
2001
- 2001-12-10 ES ES01986126T patent/ES2324594T3/es not_active Expired - Lifetime
- 2001-12-10 EP EP01986126A patent/EP1343807B1/en not_active Expired - Lifetime
- 2001-12-10 MX MXPA03005219A patent/MXPA03005219A/es active IP Right Grant
- 2001-12-10 IL IL15584201A patent/IL155842A0/xx unknown
- 2001-12-10 CA CA002430458A patent/CA2430458A1/en not_active Abandoned
- 2001-12-10 AU AU3659102A patent/AU3659102A/xx active Pending
- 2001-12-10 KR KR10-2003-7007731A patent/KR20030091946A/ko not_active Application Discontinuation
- 2001-12-10 DE DE60138567T patent/DE60138567D1/de not_active Expired - Lifetime
- 2001-12-10 AR ARP010105721A patent/AR031905A1/es unknown
- 2001-12-10 AT AT01986126T patent/ATE430166T1/de not_active IP Right Cessation
- 2001-12-10 JP JP2002549703A patent/JP4368581B2/ja not_active Expired - Fee Related
- 2001-12-10 US US10/013,071 patent/US6911428B2/en not_active Expired - Fee Related
- 2001-12-10 HU HU0303436A patent/HUP0303436A2/hu unknown
- 2001-12-10 CN CNB018204759A patent/CN1301994C/zh not_active Expired - Fee Related
- 2001-12-10 AU AU2002236591A patent/AU2002236591B2/en not_active Expired - Fee Related
- 2001-12-10 WO PCT/US2001/047383 patent/WO2002048172A2/en active Application Filing
- 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
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Publication number | Publication date |
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EP1343807A2 (en) | 2003-09-17 |
AR031905A1 (es) | 2003-10-08 |
HK1054394A1 (en) | 2003-11-28 |
KR20030091946A (ko) | 2003-12-03 |
IL155842A0 (en) | 2003-12-23 |
WO2002048172A3 (en) | 2003-06-19 |
CN1501942A (zh) | 2004-06-02 |
JP2004532812A (ja) | 2004-10-28 |
US20020147139A1 (en) | 2002-10-10 |
HK1054394B (zh) | 2009-09-25 |
CA2430458A1 (en) | 2002-06-20 |
CN1301994C (zh) | 2007-02-28 |
JP4368581B2 (ja) | 2009-11-18 |
EP1343807B1 (en) | 2009-04-29 |
ES2324594T3 (es) | 2009-08-11 |
AU3659102A (en) | 2002-06-24 |
HUP0303436A2 (hu) | 2004-01-28 |
US6911428B2 (en) | 2005-06-28 |
AU2002236591B2 (en) | 2005-07-14 |
ATE430166T1 (de) | 2009-05-15 |
WO2002048172A2 (en) | 2002-06-20 |
PE20020691A1 (es) | 2002-08-03 |
MXPA03005219A (es) | 2003-09-25 |
DE60138567D1 (de) | 2009-06-10 |
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