SI20428A - Antipicornavirusne spojine, njihova priprava in uporaba - Google Patents

Antipicornavirusne spojine, njihova priprava in uporaba Download PDF

Info

Publication number: SI20428A
Authority: SI; Slovenia
Prior art keywords: compound; acceptable salt; prodrug; solvate; pharmaceutically acceptable
Prior art date: 1998-04-30

Application number

SI9920041A

Other languages

English (en)

Slovenian (sl)

Inventor

Peter Scott Dragovich

Joseph Timothy Marakovits

Thomas Jay Prins

Jayashree Girish Tikhe

Stephen Evan Webber

Ru Zhou

Theodore O. Johnson

Original Assignee

Agouron Pharmaceuticals, 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.)

1998-04-30

Filing date

1999-01-05

Publication date

2001-06-30

1999-01-05 Application filed by Agouron Pharmaceuticals, Inc. filed Critical Agouron Pharmaceuticals, Inc.

2001-06-30 Publication of SI20428A publication Critical patent/SI20428A/sl

Links

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239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
241001144416 Picornavirales Species 0.000 claims abstract description 4
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238000005984 hydrogenation reaction Methods 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000000099 in vitro assay Methods 0.000 description 1
238000005462 in vivo assay Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
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150000007529 inorganic bases Chemical class 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000002502 liposome Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000035800 maturation Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
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IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
238000004452 microanalysis Methods 0.000 description 1
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239000002808 molecular sieve Substances 0.000 description 1
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000002797 proteolythic effect Effects 0.000 description 1
230000006337 proteolytic cleavage Effects 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
102220264985 rs182760732 Human genes 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000004513 sizing Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
239000001476 sodium potassium tartrate Substances 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
ACNRTYKOPZDRCO-UHFFFAOYSA-N tert-butyl n-(2-oxoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC=O ACNRTYKOPZDRCO-UHFFFAOYSA-N 0.000 description 1
FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000004474 valine Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000029302 virus maturation Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
150000003953 γ-lactams Chemical class 0.000 description 1
150000003954 δ-lactams Chemical group 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
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07K5/0205—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)3-C(=0)-, e.g. statine or derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Virology (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Crystallography & Structural Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)
Enzymes And Modification Thereof (AREA)
Medicines Containing Plant Substances (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

SI9920041A 1998-04-30 1999-01-05 Antipicornavirusne spojine, njihova priprava in uporaba SI20428A (sl)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US8382898P	1998-04-30	1998-04-30
US9835898P	1998-08-28	1998-08-28
PCT/US1999/000260 WO1999057135A1 (en)	1998-04-30	1999-01-05	Antipicornaviral compounds, their preparation and use

Publications (1)

Publication Number	Publication Date
SI20428A true SI20428A (sl)	2001-06-30

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ID=26769788

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SI9920041A SI20428A (sl)	1998-04-30	1999-01-05	Antipicornavirusne spojine, njihova priprava in uporaba

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US (3)	US6531452B1 (pt)
EP (1)	EP1073672B1 (pt)
JP (1)	JP2003526600A (pt)
KR (1)	KR20010043004A (pt)
CN (1)	CN1198838C (pt)
AP (1)	AP2000001934A0 (pt)
AT (2)	ATE248186T1 (pt)
AU (1)	AU768539B2 (pt)
BG (1)	BG104899A (pt)
BR (1)	BR9910573A (pt)
CA (1)	CA2326763A1 (pt)
DE (2)	DE69928140D1 (pt)
DK (1)	DK1073672T3 (pt)
EA (1)	EA003856B1 (pt)
EE (1)	EE200000621A (pt)
ES (1)	ES2205760T3 (pt)
GE (1)	GEP20022824B (pt)
HR (1)	HRP20000623A2 (pt)
HU (1)	HUP0400624A2 (pt)
IL (1)	IL138609A0 (pt)
IS (1)	IS5633A (pt)
LT (1)	LT4846B (pt)
LV (1)	LV12666B (pt)
NO (1)	NO20005411L (pt)
NZ (1)	NZ507633A (pt)
OA (1)	OA11503A (pt)
PL (1)	PL351250A1 (pt)
PT (1)	PT1073672E (pt)
SI (1)	SI20428A (pt)
SK (1)	SK284714B6 (pt)
TR (1)	TR200003159T2 (pt)
WO (1)	WO1999057135A1 (pt)
YU (1)	YU66000A (pt)

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CA2326763A1 (en)	1998-04-30	1999-11-11	Theodore O. Johnson, Jr.	Antipicornaviral compounds and compositions, their pharmaceutical uses, and methods for their synthesis
US6355807B1 (en)	1999-08-24	2002-03-12	Agouron Pharmaceuticals, Inc.	Efficient synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
US6774243B2 (en)	1999-08-24	2004-08-10	Agouron Pharmaceuticals, Inc.	Efficient synthetic routes for the preparation of rhinovirus protease inhibitors and key intermediates
PE20010517A1 (es) *	1999-08-24	2001-05-16	Agouron Pharma	Las rutas sinteticas eficientes para la preparacion de los inhibidores de la proteasa del rinovirus y los intermedios claves
PA8507801A1 (es) *	1999-12-03	2002-08-26	Agouron Pharma	Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis
PE20011277A1 (es)	2000-04-14	2002-01-07	Agouron Pharma	Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis
US6632825B2 (en)	2000-06-14	2003-10-14	Agouron Pharmaceuticals, Inc.	Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
WO2004093860A1 (en) *	2003-04-21	2004-11-04	Pfizer Inc.	Inhibitors of sars related coronavirus proteinase
US20040235952A1 (en) *	2003-05-05	2004-11-25	Agouron Pharmaceuticals, Inc.	Inhibitors of severe acute respiratory syndrome (SARS) 3C-like proteinase
EP1704142A4 (en) *	2003-12-31	2008-08-20	Taigen Biotechnology Co Ltd	PROTEASE INHIBITORS
US7462594B2 (en)	2003-12-31	2008-12-09	Taigen Biotechnology Co., Ltd.	Peptide-like compounds that inhibit coronaviral 3CL and flaviviridae viral proteases
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1999
- 1999-01-05 CA CA002326763A patent/CA2326763A1/en not_active Abandoned
- 1999-01-05 EP EP99900780A patent/EP1073672B1/en not_active Expired - Lifetime
- 1999-01-05 SK SK1604-2000A patent/SK284714B6/sk unknown
- 1999-01-05 EE EEP200000621A patent/EE200000621A/xx unknown
- 1999-01-05 DE DE69928140T patent/DE69928140D1/de not_active Expired - Lifetime
- 1999-01-05 PL PL99351250A patent/PL351250A1/xx not_active Application Discontinuation
- 1999-01-05 PT PT99900780T patent/PT1073672E/pt unknown
- 1999-01-05 ES ES99900780T patent/ES2205760T3/es not_active Expired - Lifetime
- 1999-01-05 CN CNB998056278A patent/CN1198838C/zh not_active Expired - Fee Related
- 1999-01-05 AT AT99900780T patent/ATE248186T1/de not_active IP Right Cessation
- 1999-01-05 KR KR1020007011851A patent/KR20010043004A/ko not_active Ceased
- 1999-01-05 BR BR9910573-0A patent/BR9910573A/pt not_active IP Right Cessation
- 1999-01-05 GE GEAP19995606A patent/GEP20022824B/en unknown
- 1999-01-05 AU AU20287/99A patent/AU768539B2/en not_active Ceased
- 1999-01-05 IL IL13860999A patent/IL138609A0/xx unknown
- 1999-01-05 NZ NZ507633A patent/NZ507633A/en unknown
- 1999-01-05 AT AT03009409T patent/ATE308557T1/de not_active IP Right Cessation
- 1999-01-05 HU HU0400624A patent/HUP0400624A2/hu unknown
- 1999-01-05 TR TR2000/03159T patent/TR200003159T2/xx unknown
- 1999-01-05 AP APAP/P/2000/001934A patent/AP2000001934A0/en unknown
- 1999-01-05 SI SI9920041A patent/SI20428A/sl not_active IP Right Cessation
- 1999-01-05 DK DK99900780T patent/DK1073672T3/da active
- 1999-01-05 LT LT2000109A patent/LT4846B/lt not_active IP Right Cessation
- 1999-01-05 DE DE69910762T patent/DE69910762T2/de not_active Expired - Fee Related
- 1999-01-05 HR HR20000623A patent/HRP20000623A2/hr not_active Application Discontinuation
- 1999-01-05 JP JP2000547104A patent/JP2003526600A/ja not_active Withdrawn
- 1999-01-05 WO PCT/US1999/000260 patent/WO1999057135A1/en not_active Ceased
- 1999-01-05 EA EA200001133A patent/EA003856B1/ru not_active IP Right Cessation
- 1999-01-05 YU YU66000A patent/YU66000A/sh unknown
- 1999-04-29 US US09/301,977 patent/US6531452B1/en not_active Expired - Fee Related
2000
- 2000-09-22 IS IS5633A patent/IS5633A/is unknown
- 2000-10-20 OA OA1200000288A patent/OA11503A/en unknown
- 2000-10-27 NO NO20005411A patent/NO20005411L/no not_active Application Discontinuation
- 2000-11-01 BG BG104899A patent/BG104899A/xx unknown
- 2000-12-19 LV LV000162A patent/LV12666B/xx unknown
2002
- 2002-11-06 US US10/289,982 patent/US6995142B2/en not_active Expired - Fee Related
2005
- 2005-08-24 US US11/210,717 patent/US20060046966A1/en not_active Abandoned

Also Published As

Publication number	Publication date
EP1073672B1 (en)	2003-08-27
ATE308557T1 (de)	2005-11-15
US20060046966A1 (en)	2006-03-02
CN1198838C (zh)	2005-04-27
EP1073672A1 (en)	2001-02-07
PT1073672E (pt)	2004-01-30
GEP20022824B (en)	2002-10-25
SK284714B6 (sk)	2005-09-08
US6531452B1 (en)	2003-03-11
CA2326763A1 (en)	1999-11-11
US20030130204A1 (en)	2003-07-10
AU2028799A (en)	1999-11-23
ES2205760T3 (es)	2004-05-01
DE69910762T2 (de)	2004-03-11
DE69928140D1 (de)	2005-12-08
AP2000001934A0 (en)	2000-12-31
JP2003526600A (ja)	2003-09-09
AU768539B2 (en)	2003-12-18
US6995142B2 (en)	2006-02-07
BR9910573A (pt)	2001-01-16
ATE248186T1 (de)	2003-09-15
BG104899A (en)	2001-08-31
NO20005411D0 (no)	2000-10-27
LV12666B (lv)	2001-11-20
HRP20000623A2 (en)	2001-04-30
EA200001133A1 (ru)	2001-08-27
IS5633A (is)	2000-09-22
EE200000621A (et)	2002-06-17
LV12666A (en)	2001-05-20
SK16042000A3 (sk)	2001-05-10
DK1073672T3 (da)	2003-12-08
DE69910762D1 (de)	2003-10-02
IL138609A0 (en)	2001-10-31
EA003856B1 (ru)	2003-10-30
WO1999057135A1 (en)	1999-11-11
HK1034722A1 (en)	2001-11-02
PL351250A1 (en)	2003-04-07
NO20005411L (no)	2000-10-27
OA11503A (en)	2004-05-10
HUP0400624A2 (hu)	2004-06-28
KR20010043004A (ko)	2001-05-25
LT2000109A (en)	2001-05-25
YU66000A (sh)	2003-12-31
CN1311793A (zh)	2001-09-05
NZ507633A (en)	2003-10-31
TR200003159T2 (tr)	2001-09-21
LT4846B (lt)	2001-10-25

Legal Events

Date	Code	Title	Description
2004-12-31	KO00	Lapse of patent	Effective date: 20041027

Publication	Publication Date	Title
SI20428A (sl)	2001-06-30	Antipicornavirusne spojine, njihova priprava in uporaba
AU779321B2 (en)	2005-01-20	Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
US5962487A (en)	1999-10-05	Antipicornaviral compounds and methods for their use and preparation
EP0910572B1 (en)	2005-04-27	Inhibitors of picornavirus 3c proteases and methods for their use and preparation
AU736550B2 (en)	2001-08-02	Antipicornaviral compounds, compositions containing them, and methods for their use
US6331554B1 (en)	2001-12-18	Antipicornaviral compounds, compositions containing them, and methods for their use
US6362166B1 (en)	2002-03-26	Antipicornaviral compounds and methods for their use and preparation
US6906198B1 (en)	2005-06-14	Antipicornaviral compounds, their preparation and use
EP1329457B1 (en)	2005-11-02	Antipicornaviral compounds, their preparation and use
HK1034722B (en)	2003-11-28	Antipicornaviral compounds, their preparation and use
MXPA00010406A (en)	2001-07-31	Antipicornaviral compounds, their preparation and use
CZ20003986A3 (cs)	2001-06-13	Antipicornavirální součeniny a kompozice, jejich farmaceutické použití a materiály pro jejich syntézu