ZA200210311B - Novel petides as NS3-serine protease inhibitors of hepatitis C virus. - Google Patents

Novel petides as NS3-serine protease inhibitors of hepatitis C virus. Download PDF

Info

Publication number: ZA200210311B
Authority: ZA; South Africa
Prior art keywords: compound; composition; cooh; substance; alkyl
Prior art date: 2000-07-21

Application number

ZA200210311A

Other languages

English (en)

Inventor

Anil K Saksena

Stephane L Bogen

Edwin E Jao

Jinping L Mc Cormick

Russel E Pike

Tin-Yau Chan

Ashok Arasappan

Srikanth Venkatraman

Patrick A Pinto

F George Njoroge

Henry A Vaccaro

Odile Esther Levy

Susan Y Tamura

Viyyor Moopil Girijavallabhan

Raymond G Lovey

Frank Bennett

Haiyan Wang

Yi-Tsung Liu

Zhaoning Zhu

Kevin X Chen

Tejal N Parekh

Bama Santhanam

Ashit K Ganguly

Scott Jeffrey Kemp

Marguerita Lim-Wilby

Original Assignee

Schering Corp

Corvas Int Inc

Priority date (The priority date 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 date listed.)

2000-07-21

Filing date

2002-12-19

Publication date

2004-03-19

2002-12-19 Application filed by Schering Corp, Corvas Int Inc filed Critical Schering Corp

2004-03-19 Publication of ZA200210311B publication Critical patent/ZA200210311B/en

Links

241000711549 Hepacivirus C Species 0.000 title claims description 54
239000003001 serine protease inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 69
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
238000000034 method Methods 0.000 claims description 34
-1 enantiomers Chemical class 0.000 claims description 29
108091005804 Peptidases Proteins 0.000 claims description 22
239000004365 Protease Substances 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 22
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
108090000765 processed proteins & peptides Proteins 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
102000004196 processed proteins & peptides Human genes 0.000 claims description 13
125000001072 heteroaryl group Chemical group 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
229920001184 polypeptide Polymers 0.000 claims description 10
125000004404 heteroalkyl group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000002877 alkyl aryl group Chemical group 0.000 claims description 8
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
229940079322 interferon Drugs 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
208000005176 Hepatitis C Diseases 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000001769 aryl amino group Chemical group 0.000 claims description 6
125000005110 aryl thio group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004437 phosphorous atom Chemical group 0.000 claims description 6
102000014150 Interferons Human genes 0.000 claims description 5
108010050904 Interferons Proteins 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
208000024891 symptom Diseases 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 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 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
229960000329 ribavirin Drugs 0.000 claims description 3
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 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
229940100389 Sulfonylurea Drugs 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 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
125000005248 alkyl aryloxy group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
125000005281 alkyl ureido group Chemical group 0.000 claims description 2
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
125000005421 aryl sulfonamido group Chemical group 0.000 claims description 2
UZMZVDOOVXLRID-UHFFFAOYSA-N azanylidyne-(nitrosulfonylamino)methane Chemical compound [O-][N+](=O)S(=O)(=O)NC#N UZMZVDOOVXLRID-UHFFFAOYSA-N 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
125000005241 heteroarylamino group Chemical group 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
125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 2
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
125000005936 piperidyl group Chemical class 0.000 claims description 2
125000004076 pyridyl group Chemical class 0.000 claims description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
150000003457 sulfones Chemical class 0.000 claims description 2
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 2
150000003462 sulfoxides Chemical class 0.000 claims description 2
125000001544 thienyl group Chemical class 0.000 claims description 2
239000000203 mixture Substances 0.000 claims 33
239000000126 substance Substances 0.000 claims 29
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 15
238000004519 manufacturing process Methods 0.000 claims 7
239000003443 antiviral agent Substances 0.000 claims 4
150000003839 salts Chemical class 0.000 claims 3
239000012453 solvate Substances 0.000 claims 3
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 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
230000002401 inhibitory effect Effects 0.000 claims 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
101710179738 6,7-dimethyl-8-ribityllumazine synthase 1 Proteins 0.000 claims 1
102100020870 La-related protein 6 Human genes 0.000 claims 1
108050008265 La-related protein 6 Proteins 0.000 claims 1
101710186608 Lipoyl synthase 1 Proteins 0.000 claims 1
101710137584 Lipoyl synthase 1, chloroplastic Proteins 0.000 claims 1
101710090391 Lipoyl synthase 1, mitochondrial Proteins 0.000 claims 1
229910006074 SO2NH2 Inorganic materials 0.000 claims 1
PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
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 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000001747 exhibiting effect Effects 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
238000007920 subcutaneous administration Methods 0.000 claims 1
101710144111 Non-structural protein 3 Proteins 0.000 description 14
239000003112 inhibitor Substances 0.000 description 10
108010022999 Serine Proteases Proteins 0.000 description 9
102000012479 Serine Proteases Human genes 0.000 description 9
102100038132 Endogenous retrovirus group K member 6 Pro protein Human genes 0.000 description 8
238000003776 cleavage reaction Methods 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
235000018102 proteins Nutrition 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
230000007017 scission Effects 0.000 description 5
208000006454 hepatitis Diseases 0.000 description 4
231100000283 hepatitis Toxicity 0.000 description 4
206010016654 Fibrosis Diseases 0.000 description 3
230000007882 cirrhosis Effects 0.000 description 3
208000019425 cirrhosis of liver Diseases 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
241000701022 Cytomegalovirus Species 0.000 description 2
241000701044 Human gammaherpesvirus 4 Species 0.000 description 2
108010076039 Polyproteins Proteins 0.000 description 2
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
241000700605 Viruses Species 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
239000003541 chymotrypsin inhibitor Substances 0.000 description 2
208000029570 hepatitis D virus infection Diseases 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
208000007848 Alcoholism Diseases 0.000 description 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
101100309570 Caenorhabditis elegans let-765 gene Proteins 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
WYVKPHCYMTWUCW-YUPRTTJUSA-N Cys-Thr Chemical group C[C@@H]([C@@H](C(=O)O)NC(=O)[C@H](CS)N)O WYVKPHCYMTWUCW-YUPRTTJUSA-N 0.000 description 1
101710091045 Envelope protein Proteins 0.000 description 1
108010074860 Factor Xa 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
101001098529 Homo sapiens Proteinase-activated receptor 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
101100129514 Mus musculus Mbip gene Proteins 0.000 description 1
125000001429 N-terminal alpha-amino-acid group Chemical group 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
102100037136 Proteinase-activated receptor 1 Human genes 0.000 description 1
108010049219 RNA-dependent ATPase Proteins 0.000 description 1
101800001838 Serine protease/helicase NS3 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
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 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
230000000840 anti-viral effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 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
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
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
208000035475 disorder Diseases 0.000 description 1
241001493065 dsRNA viruses Species 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
102000057815 human SPINK1 Human genes 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 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
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
230000003612 virological effect Effects 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
- C07K5/10—Tetrapeptides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- A61K38/05—Dipeptides
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
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- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
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- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
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- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
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ZA200210311A 2000-07-21 2002-12-19 Novel petides as NS3-serine protease inhibitors of hepatitis C virus. ZA200210311B (en)

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US22010700P	2000-07-21	2000-07-21

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ZA200210311A ZA200210311B (en)	2000-07-21	2002-12-19	Novel petides as NS3-serine protease inhibitors of hepatitis C virus.

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US (2)	US7169760B2 (cs)
EP (1)	EP1303487A4 (cs)
JP (2)	JP4452441B2 (cs)
KR (1)	KR20030081297A (cs)
CN (1)	CN1446201A (cs)
AR (1)	AR030249A1 (cs)
AU (1)	AU8063701A (cs)
BR (1)	BR0112666A (cs)
CA (1)	CA2410682A1 (cs)
CZ (1)	CZ2003195A3 (cs)
EC (1)	ECSP034439A (cs)
HU (1)	HUP0303358A3 (cs)
IL (1)	IL153669A0 (cs)
MX (1)	MXPA03000626A (cs)
NO (1)	NO20030271L (cs)
NZ (1)	NZ523781A (cs)
PE (1)	PE20020266A1 (cs)
PL (1)	PL365695A1 (cs)
RU (1)	RU2003105221A (cs)
SK (1)	SK742003A3 (cs)
WO (1)	WO2002008187A1 (cs)
ZA (1)	ZA200210311B (cs)

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- 2001-07-19 WO PCT/US2001/022813 patent/WO2002008187A1/en not_active Ceased
- 2001-07-19 CA CA002410682A patent/CA2410682A1/en not_active Abandoned
- 2001-07-19 EP EP01959041A patent/EP1303487A4/en not_active Withdrawn
- 2001-07-19 JP JP2002514094A patent/JP4452441B2/ja not_active Expired - Fee Related
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- 2001-07-19 NZ NZ523781A patent/NZ523781A/en unknown
- 2001-07-19 AU AU8063701A patent/AU8063701A/xx not_active Withdrawn
- 2001-07-19 MX MXPA03000626A patent/MXPA03000626A/es unknown
- 2001-07-19 US US09/909,012 patent/US7169760B2/en not_active Expired - Lifetime
- 2001-07-19 RU RU2003105221/04A patent/RU2003105221A/ru not_active Application Discontinuation
- 2001-07-19 PE PE2001000733A patent/PE20020266A1/es not_active Application Discontinuation
- 2001-07-19 IL IL15366901A patent/IL153669A0/xx unknown
- 2001-07-19 PL PL01365695A patent/PL365695A1/xx not_active Application Discontinuation
- 2001-07-19 CN CN01813921A patent/CN1446201A/zh active Pending
- 2001-07-19 KR KR10-2003-7000861A patent/KR20030081297A/ko not_active Ceased
- 2001-07-19 CZ CZ2003195A patent/CZ2003195A3/cs unknown
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2002
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2003
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2005
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JP2009292832A (ja)	2009-12-17
MXPA03000626A (es)	2004-07-30
AU8063701A (en)	2002-02-05
EP1303487A4 (en)	2005-11-23
CZ2003195A3 (cs)	2003-04-16
JP4452441B2 (ja)	2010-04-21
RU2003105221A (ru)	2004-09-20
BR0112666A (pt)	2003-06-10
US20020160962A1 (en)	2002-10-31
NZ523781A (en)	2004-10-29
CA2410682A1 (en)	2002-01-31
CN1446201A (zh)	2003-10-01
HUP0303358A3 (en)	2005-10-28
PE20020266A1 (es)	2002-05-11
WO2002008187A1 (en)	2002-01-31
SK742003A3 (en)	2003-06-03
NO20030271D0 (no)	2003-01-20
JP2004513881A (ja)	2004-05-13
PL365695A1 (en)	2005-01-10
NO20030271L (no)	2003-03-18
ECSP034439A (es)	2003-03-10
US20050176648A1 (en)	2005-08-11
AR030249A1 (es)	2003-08-13
EP1303487A1 (en)	2003-04-23
US7595299B2 (en)	2009-09-29
IL153669A0 (en)	2003-07-06
US7169760B2 (en)	2007-01-30
KR20030081297A (ko)	2003-10-17
WO2002008187A9 (en)	2003-01-03
HUP0303358A2 (hu)	2004-01-28

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