SK17482000A3 - Antivírusové zlúčeniny, spôsob inhibície vírusov a farmaceutický prípravok - Google Patents

Antivírusové zlúčeniny, spôsob inhibície vírusov a farmaceutický prípravok Download PDF

Info

Publication number: SK17482000A3
Authority: SK; Slovakia
Prior art keywords: mmol; pyridine; imidazo; preparation; converted
Prior art date: 1998-05-20

Application number

SK1748-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Jesus Ezquerra-Carrera

Joseph Michael Gruber

Hamdouchi Chafiq Hamdouchi

Richard Elmer Holmes

Wayne Alfred Spitzer

Original Assignee

Eli Lilly And Company

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.)

1998-05-20

Filing date

1998-05-20

Publication date

2005-03-04

1998-05-20 Application filed by Eli Lilly And Company filed Critical Eli Lilly And Company

2005-03-04 Publication of SK17482000A3 publication Critical patent/SK17482000A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 172
238000000034 method Methods 0.000 title claims description 110
230000002401 inhibitory effect Effects 0.000 title claims description 8
230000000840 anti-viral effect Effects 0.000 title claims description 4
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
241000700605 Viruses Species 0.000 title abstract description 9
-1 CONHOCH3 Chemical group 0.000 claims abstract description 59
150000003839 salts Chemical class 0.000 claims abstract description 31
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
125000004076 pyridyl group Chemical group 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 16
241000709664 Picornaviridae Species 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
125000001624 naphthyl group Chemical group 0.000 claims abstract description 7
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
125000002541 furyl group Chemical group 0.000 claims abstract description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 7
150000002431 hydrogen Chemical group 0.000 claims abstract 6
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
241000711549 Hepacivirus C Species 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004212 difluorophenyl group Chemical group 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
241000709661 Enterovirus Species 0.000 abstract description 15
241001466953 Echovirus Species 0.000 abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
241000709687 Coxsackievirus Species 0.000 abstract description 3
241000991587 Enterovirus C Species 0.000 abstract description 3
241000710185 Mengo virus Species 0.000 abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
241000710190 Cardiovirus Species 0.000 abstract description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
239000000047 product Substances 0.000 description 142
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 139
238000002360 preparation method Methods 0.000 description 135
238000005481 NMR spectroscopy Methods 0.000 description 110
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 104
239000002904 solvent Substances 0.000 description 90
239000000243 solution Substances 0.000 description 88
230000002829 reductive effect Effects 0.000 description 74
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000007787 solid Substances 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
239000000460 chlorine Substances 0.000 description 47
239000000203 mixture Substances 0.000 description 45
239000011541 reaction mixture Substances 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
239000011734 sodium Substances 0.000 description 34
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239000002585 base Substances 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
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238000010992 reflux Methods 0.000 description 20
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238000002451 electron ionisation mass spectrometry Methods 0.000 description 19
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 18
UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
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238000003756 stirring Methods 0.000 description 16
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238000004440 column chromatography Methods 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 11
229920002554 vinyl polymer Polymers 0.000 description 11
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 10
229910052751 metal Inorganic materials 0.000 description 10
239000002184 metal Substances 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
239000012300 argon atmosphere Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 9
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
150000001298 alcohols Chemical class 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
229910052744 lithium Inorganic materials 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
ZALOOIGRDWEGRD-UHFFFAOYSA-N 2-amino-n-methoxy-n-methyl-3-phenylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)N(C)OC)C=CC2=NC(N)=C1C1=CC=CC=C1 ZALOOIGRDWEGRD-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000011630 iodine Chemical group 0.000 description 6
229910052740 iodine Chemical group 0.000 description 6
239000010410 layer Substances 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
239000000725 suspension Substances 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
150000003568 thioethers Chemical class 0.000 description 6
APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
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230000015572 biosynthetic process Effects 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
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239000007858 starting material Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
230000003612 virological effect Effects 0.000 description 5
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239000002775 capsule Substances 0.000 description 4
239000012320 chlorinating reagent Substances 0.000 description 4
239000010949 copper Substances 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000284 extract Substances 0.000 description 4
230000002140 halogenating effect Effects 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
239000003999 initiator Substances 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
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UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
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239000000376 reactant Substances 0.000 description 4
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
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239000000126 substance Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
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UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
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FMEBIWNKYZUWFV-UHFFFAOYSA-N 6-chloropyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)N=C1 FMEBIWNKYZUWFV-UHFFFAOYSA-N 0.000 description 3
108091003079 Bovine Serum Albumin Proteins 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
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UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
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238000004458 analytical method Methods 0.000 description 3
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RRORQNSWYJCUEH-UHFFFAOYSA-N methyl 3-phenyl-2-[(2,2,2-trifluoroacetyl)amino]imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(NC(=O)C(F)(F)F)=C1C1=CC=CC=C1 RRORQNSWYJCUEH-UHFFFAOYSA-N 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
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238000006053 organic reaction Methods 0.000 description 3
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
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FQAWVJRQBWWDAK-UHFFFAOYSA-N (2-amino-3-phenylimidazo[1,2-a]pyridin-6-yl)-(4-fluorophenyl)methanone Chemical compound NC=1N=C2C=CC(C(=O)C=3C=CC(F)=CC=3)=CN2C=1C1=CC=CC=C1 FQAWVJRQBWWDAK-UHFFFAOYSA-N 0.000 description 1
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MZKVJTZWGLDKCY-UHFFFAOYSA-N (2-amino-3-propan-2-ylsulfanylimidazo[1,2-a]pyridin-6-yl)-phenylmethanone Chemical compound C=1N2C(SC(C)C)=C(N)N=C2C=CC=1C(=O)C1=CC=CC=C1 MZKVJTZWGLDKCY-UHFFFAOYSA-N 0.000 description 1
WRSPXXSVDJXBRT-UHFFFAOYSA-N (6-chloropyridin-3-yl)-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(Cl)N=C1 WRSPXXSVDJXBRT-UHFFFAOYSA-N 0.000 description 1
KOEFYSIDTCOEBV-LFIBNONCSA-N (E)-N-methyl-3-phenyl-3-[2-[(2,2,2-trifluoroacetyl)amino]-3-(2,3,4-trifluorophenyl)imidazo[1,2-a]pyridin-6-yl]prop-2-enamide Chemical compound C1=CC2=NC(NC(=O)C(F)(F)F)=C(C=3C(=C(F)C(F)=CC=3)F)N2C=C1C(=C/C(=O)NC)/C1=CC=CC=C1 KOEFYSIDTCOEBV-LFIBNONCSA-N 0.000 description 1
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229940124597 therapeutic agent Drugs 0.000 description 1
238000004448 titration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000017105 transposition Effects 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- 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
- A61K31/435—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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Oncology (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Gastroenterology & Hepatology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

SK1748-2000A 1998-05-20 1998-05-20 Antivírusové zlúčeniny, spôsob inhibície vírusov a farmaceutický prípravok SK17482000A3 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US1998/010299 WO1999059587A1 (en)	1998-05-20	1998-05-20	Anti-viral compounds

Publications (1)

Publication Number	Publication Date
SK17482000A3 true SK17482000A3 (sk)	2005-03-04

Family

ID=22267098

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1748-2000A SK17482000A3 (sk)	1998-05-20	1998-05-20	Antivírusové zlúčeniny, spôsob inhibície vírusov a farmaceutický prípravok

Country Status (15)

Country	Link
EP (1)	EP1077701A4 (no)
JP (1)	JP2002515433A (no)
KR (1)	KR20010025055A (no)
CN (1)	CN1292697A (no)
AU (1)	AU7583098A (no)
BR (1)	BR9815899A (no)
CA (1)	CA2332403A1 (no)
CZ (1)	CZ289425B6 (no)
EA (1)	EA200001208A1 (no)
HU (1)	HUP0102117A2 (no)
IL (1)	IL139166A0 (no)
NO (1)	NO20005795L (no)
SK (1)	SK17482000A3 (no)
TR (1)	TR200003414T2 (no)
WO (1)	WO1999059587A1 (no)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
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AUPR213700A0 (en) *	2000-12-18	2001-01-25	Biota Scientific Management Pty Ltd	Antiviral agents
AR048650A1 (es) *	2004-05-04	2006-05-10	Tibotec Pharm Ltd	Derivados de (1,10b-dihidro-2-(aminocarbonil-fenil)-5h-pirazolo[1,5 c][1,3]benzoxazin-5-il)fenil metanona como inhibidores de la replicacion viral del vih
WO2006020830A2 (en)	2004-08-12	2006-02-23	Amgen Inc.	Bisaryl-sulfonamides
US7666880B2 (en)	2005-03-21	2010-02-23	S*Bio Pte Ltd.	Imidazo[1,2-A]pyridine derivatives: preparation and pharmaceutical applications
MY147647A (en) *	2005-03-21	2012-12-31	S Bio Pte Ltd	Imidazo [1,2-a] pyridine derivatives : preparation and pharmaceutical applications
WO2007081517A2 (en)	2005-12-21	2007-07-19	Abbott Laboratories	Anti-viral compounds
US7910595B2 (en)	2005-12-21	2011-03-22	Abbott Laboratories	Anti-viral compounds
EP1979349B1 (en)	2005-12-21	2010-07-28	Abbott Laboratories	Anti-viral compounds
US8236950B2 (en)	2006-12-20	2012-08-07	Abbott Laboratories	Anti-viral compounds
CN102046621B (zh) *	2008-05-27	2014-11-12	生物区科学管理控股有限公司	抗病毒盐
SG172352A1 (en)	2008-12-23	2011-07-28	Abbott Lab	Anti-viral compounds
US8546405B2 (en)	2008-12-23	2013-10-01	Abbott Laboratories	Anti-viral compounds
US9278922B2 (en)	2009-04-15	2016-03-08	Abbvie Inc.	Anti-viral compounds
WO2014060381A1 (de)	2012-10-18	2014-04-24	Bayer Cropscience Ag	Heterocyclische verbindungen als schädlingsbekämpfungsmittel
JP2016503395A (ja)	2012-10-31	2016-02-04	バイエル・クロップサイエンス・アクチェンゲゼルシャフト	病害生物防除剤としての複素環化合物
CN104370732B (zh) *	2014-01-26	2015-08-19	山东信立泰药业有限公司	一种氯吡格雷及其中间体的制备方法
CN109535405B (zh) *	2017-09-21	2021-07-30	宁波聚嘉新材料科技有限公司	一种基于2-(4-羧基苯基)-5-羟基吡啶并咪唑的聚芳酯的制备方法
CN109810085B (zh) *	2019-04-19	2019-07-19	上海皓元生物医药科技有限公司	Acc抑制剂及其中间体的制备方法
CN110746450A (zh) *	2019-09-17	2020-02-04	济南康和医药科技有限公司	一种贝前列素钠关键中间体的合成方法
CN117902992A (zh) *	2024-01-04	2024-04-19	浙江永太科技股份有限公司	一种2,4-二氟苯基甘氨酸的制备方法

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US4096264A (en) *	1975-12-09	1978-06-20	Merck & Co., Inc.	Certain substituted imidazo [1,2-a] pyridines
US4250174A (en) *	1979-05-02	1981-02-10	Merck & Co., Inc.	3-Substituted imidazo [1,2-A] pyridines
US5693661A (en) *	1995-06-07	1997-12-02	Eli Lilly And Company	Anti-viral compounds
EP0906097A4 (en) *	1996-06-05	2000-12-13	Lilly Co Eli	ANTIVIRAL COMPOUNDS
US5891874A (en) *	1996-06-05	1999-04-06	Eli Lilly And Company	Anti-viral compound
US5821242A (en) *	1996-06-06	1998-10-13	Eli Lilly And Company	Anti-viral compounds

1998
- 1998-05-20 BR BR9815899-6A patent/BR9815899A/pt not_active IP Right Cessation
- 1998-05-20 JP JP2000549252A patent/JP2002515433A/ja not_active Withdrawn
- 1998-05-20 WO PCT/US1998/010299 patent/WO1999059587A1/en not_active Ceased
- 1998-05-20 CA CA002332403A patent/CA2332403A1/en not_active Abandoned
- 1998-05-20 SK SK1748-2000A patent/SK17482000A3/sk unknown
- 1998-05-20 KR KR1020007012999A patent/KR20010025055A/ko not_active Withdrawn
- 1998-05-20 CN CN988140519A patent/CN1292697A/zh active Pending
- 1998-05-20 AU AU75830/98A patent/AU7583098A/en not_active Abandoned
- 1998-05-20 EP EP98923565A patent/EP1077701A4/en not_active Withdrawn
- 1998-05-20 HU HU0102117A patent/HUP0102117A2/hu unknown
- 1998-05-20 CZ CZ20004278A patent/CZ289425B6/cs unknown
- 1998-05-20 EA EA200001208A patent/EA200001208A1/ru unknown
- 1998-05-20 TR TR2000/03414T patent/TR200003414T2/xx unknown
- 1998-05-20 IL IL13916698A patent/IL139166A0/xx unknown
2000
- 2000-11-16 NO NO20005795A patent/NO20005795L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EA200001208A1 (ru)	2001-06-25
BR9815899A (pt)	2001-02-20
CA2332403A1 (en)	1999-11-25
AU7583098A (en)	1999-12-06
KR20010025055A (ko)	2001-03-26
NO20005795D0 (no)	2000-11-16
WO1999059587A1 (en)	1999-11-25
JP2002515433A (ja)	2002-05-28
EP1077701A4 (en)	2002-03-20
IL139166A0 (en)	2001-11-25
CN1292697A (zh)	2001-04-25
TR200003414T2 (tr)	2001-03-21
HUP0102117A2 (hu)	2001-12-28
EP1077701A1 (en)	2001-02-28
NO20005795L (no)	2001-01-18
CZ289425B6 (cs)	2002-01-16
CZ20004278A3 (en)	2001-05-16

Publication	Publication Date	Title
SK17482000A3 (sk)	2005-03-04	Antivírusové zlúčeniny, spôsob inhibície vírusov a farmaceutický prípravok
ES2750236T3 (es)	2020-03-25	Derivados heteroaromáticos bicíclicos condensados como moduladores de la actividad del TNF
RU2677696C1 (ru)	2019-01-21	Производные бензотриазола в качестве модуляторов активности tnf
AU2018269348B2 (en)	2020-12-24	Histone deacetylases (HDACs) inhibitors
AU2019373203A1 (en)	2021-06-10	Amide-substituted heterocyclic compounds for the treatment of conditions related to the modulation of IL-12, IL-23 and/or IFN-alpha
PH12015501004B1 (en)	2015-07-27	AMIDE-SUBSTITUTED HETEROCYCLIC COMPOUNDS USEFUL AS MODULATORS OF IL-12, IL-23 AND/OR IFN ALPHa RESPONSES
US20200181115A1 (en)	2020-06-11	Method for preparing 2-hydroxyl-4-(2, 3-disubstituted benzyloxy)-5-substituted benzaldehyde derivative
EP3752497B1 (en)	2024-07-17	P300/cbp hat inhibitors
CN103562200A (zh)	2014-02-05	用于治疗关节炎的新咪唑衍生物
WO1997040027A1 (en)	1997-10-30	Substituted benzylamines and their use for the treatment of depression
AU2008320718A1 (en)	2009-05-07	Indol-2-one derivatives disubstituted in the 3-position, preparation thereof and therapeutic use thereof
US6358971B1 (en)	2002-03-19	Anti-viral compounds
US6114327A (en)	2000-09-05	Anti-viral compounds
EA014233B1 (ru)	2010-10-29	Замещенные карбоксамиды
KR19990022363A (ko)	1999-03-25	항바이러스 화합물
CN106866548B (zh)	2019-08-27	6-环已甲基嘧啶酮类hiv逆转录酶抑制剂、其制备方法和用途
Zhu et al.	2005	Chemoselective Multicomponent Condensation of 1, 3-Cyclohexanedione, Urea or Thiourea with Aldehydes, One-Pot Synthesis of Two Families of Fused Heterobicyclic and Spiro-fused Heterobicyclic
JP2001502661A (ja)	2001-02-27	抗―ウイルス性化合物群
US6087374A (en)	2000-07-11	Anti-viral compounds
SU1169538A3 (ru)	1985-07-23	Способ получени трициклических соединений
JPS6137249B2 (no)	1986-08-22
US12570658B2 (en)	2026-03-10	Synthetic methods of making (2H-1, 2, 3-triazol-2-yl) phenyl compounds as orexin receptor modulators
MXPA00011173A (en)	2001-07-31	Anti-viral compounds
RU2089553C1 (ru)	1997-09-10	Производные тетрагидротиено(3,2-с)пиридина или их фуро-аналоги и способ их получения
EA046399B1 (ru)	2024-03-08	Усовершенствованные синтетические способы получения (2h-1,2,3-триазол-2-ил)фенильных соединений в качестве модуляторов рецепторов орексина