ZA200300286B - Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their syntheis. - Google Patents
Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their syntheis. Download PDFInfo
- Publication number
- ZA200300286B ZA200300286B ZA200300286A ZA200300286A ZA200300286B ZA 200300286 B ZA200300286 B ZA 200300286B ZA 200300286 A ZA200300286 A ZA 200300286A ZA 200300286 A ZA200300286 A ZA 200300286A ZA 200300286 B ZA200300286 B ZA 200300286B
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- ZA
- South Africa
- Prior art keywords
- alkyl
- group
- ethyl ester
- acid ethyl
- aryl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 46
- 239000000463 material Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 134
- 125000003118 aryl group Chemical group 0.000 claims description 96
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 95
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 86
- -1 each R¥is H Chemical group 0.000 claims description 80
- 125000001424 substituent group Chemical group 0.000 claims description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 239000002207 metabolite Substances 0.000 claims description 25
- 239000000651 prodrug Substances 0.000 claims description 25
- 229940002612 prodrug Drugs 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000012453 solvate Substances 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000003441 thioacyl group Chemical group 0.000 claims description 14
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 241001144416 Picornavirales Species 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 102100033668 Cartilage matrix protein Human genes 0.000 claims description 2
- 101001018382 Homo sapiens Cartilage matrix protein Proteins 0.000 claims description 2
- 238000004113 cell culture Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 4
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 102100038018 Corticotropin-releasing factor receptor 1 Human genes 0.000 claims 1
- 101000878678 Homo sapiens Corticotropin-releasing factor receptor 1 Proteins 0.000 claims 1
- 238000003556 assay Methods 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- LXYHWLQXGQTDSR-HMBFSZGFSA-N ethyl (e,4s)-4-[(6-bromo-2h-chromene-3-carbonyl)amino]-5-[(3s)-2-oxopyrrolidin-3-yl]pent-2-enoate Chemical compound C([C@@H](/C=C/C(=O)OCC)NC(=O)C=1COC2=CC=C(Br)C=C2C=1)[C@@H]1CCNC1=O LXYHWLQXGQTDSR-HMBFSZGFSA-N 0.000 claims 1
- NUDKXDHNYUAITK-UHFFFAOYSA-N ethyl 4-[(5-methyl-1h-indole-2-carbonyl)amino]-5-(2-oxopyrrolidin-3-yl)pent-2-enoate Chemical compound C=1C2=CC(C)=CC=C2NC=1C(=O)NC(C=CC(=O)OCC)CC1CCNC1=O NUDKXDHNYUAITK-UHFFFAOYSA-N 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 1
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- 239000003981 vehicle Substances 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
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- 150000003254 radicals Chemical class 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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- 241000430519 Human rhinovirus sp. Species 0.000 description 2
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- 108010076039 Polyproteins Proteins 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 125000003106 haloaryl group Chemical group 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
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- 125000006413 ring segment Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- ILWJAOPQHOZXAN-UHFFFAOYSA-N 1,3-dithianyl Chemical group [CH]1SCCCS1 ILWJAOPQHOZXAN-UHFFFAOYSA-N 0.000 description 1
- KFHQOZXAFUKFNB-UHFFFAOYSA-N 1,3-oxathiolanyl Chemical group [CH]1OCCS1 KFHQOZXAFUKFNB-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
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- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
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- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
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- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 description 1
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 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 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005347 halocycloalkyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 description 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 description 1
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 description 1
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 230000002452 interceptive effect Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005327 perimidinyl group Chemical group N1C(=NC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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Classifications
-
- 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/16—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21142400P | 2000-06-14 | 2000-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300286B true ZA200300286B (en) | 2004-04-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200300286A ZA200300286B (en) | 2000-06-14 | 2003-01-10 | Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their syntheis. |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US6632825B2 (fr) |
| EP (1) | EP1355878A2 (fr) |
| JP (1) | JP2004503533A (fr) |
| KR (1) | KR20030010718A (fr) |
| CN (1) | CN1525957A (fr) |
| AU (1) | AU2001266924A1 (fr) |
| BR (1) | BR0111727A (fr) |
| CA (1) | CA2412618A1 (fr) |
| HU (1) | HUP0301331A3 (fr) |
| IL (1) | IL153431A0 (fr) |
| MX (1) | MXPA02012456A (fr) |
| NZ (1) | NZ523134A (fr) |
| PL (1) | PL365470A1 (fr) |
| WO (1) | WO2001096297A2 (fr) |
| ZA (1) | ZA200300286B (fr) |
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| PE20011277A1 (es) * | 2000-04-14 | 2002-01-07 | Agouron Pharma | Compuestos y composiciones antipicornavirales, sus usos farmaceuticos y los materiales para su sintesis |
| SI2281801T1 (sl) | 2009-07-27 | 2014-04-30 | Crystal Pharma, S.A.U. | Postopek za pridobivanje 3,3-diphenilpropilamina |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4652676A (en) | 1985-05-06 | 1987-03-24 | General Foods Corporation | L-aminodicarboxylic acid alkenes |
| WO1992022570A1 (fr) | 1991-06-14 | 1992-12-23 | Chiron Corporation | Inhibiteurs de proteases picornavirales |
| US5374623A (en) | 1992-08-20 | 1994-12-20 | Prototek, Inc. | Cysteine protease inhibitors effective for in vivo use |
| US5514778A (en) | 1993-07-01 | 1996-05-07 | Eli Lilly And Company | Anti-picornaviral agents |
| US5486623A (en) | 1993-12-08 | 1996-01-23 | Prototek, Inc. | Cysteine protease inhibitors containing heterocyclic leaving groups |
| IL112759A0 (en) | 1994-02-25 | 1995-05-26 | Khepri Pharmaceuticals Inc | Novel cysteine protease inhibitors |
| IT1269511B (it) | 1994-05-17 | 1997-04-01 | Univ Degli Studi Milano | Derivati di acidi ammino-solfonici , loro impiego nella sintesi di pseudopeptidi e procedimento per la loro preparazione |
| US5498616A (en) | 1994-11-04 | 1996-03-12 | Cephalon, Inc. | Cysteine protease and serine protease inhibitors |
| CA2215211A1 (fr) | 1995-03-31 | 1996-10-03 | Takeda Chemical Industries, Ltd. | Inhibiteur de la protease de cysteine |
| IL120310A (en) | 1996-03-01 | 2002-02-10 | Akzo Nobel Nv | Serine protease inhibitors and pharmaceuticals containing them |
| US5856530A (en) | 1996-05-14 | 1999-01-05 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds and methods for their use and preparation |
| ES2242225T3 (es) | 1996-05-14 | 2005-11-01 | Agouron Pharmaceuticals, Inc. | Inhibidores de proteasas 3c antipicornavirales y procedimientos correspondientes de utilizacion y de preparacion. |
| WO1997049668A1 (fr) | 1996-06-13 | 1997-12-31 | Smithkline Beecham Corporation | Inhibiteurs de cysteine protease |
| US6331554B1 (en) | 1997-03-28 | 2001-12-18 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds, compositions containing them, and methods for their use |
| EP0975588B1 (fr) * | 1997-03-28 | 2003-09-03 | Agouron Pharmaceuticals, Inc. | Composes anti-picornavirus, compositions contenant ces composes et leurs procedes d'utilisation |
| US6020371A (en) | 1997-03-28 | 2000-02-01 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds compositions containing them and methods for their use |
| US5962487A (en) | 1997-12-16 | 1999-10-05 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds and methods for their use and preparation |
| ES2205760T3 (es) | 1998-04-30 | 2004-05-01 | Agouron Pharmaceuticals, Inc. | Compuestos antipicornavirales, su preparacion y su utilizacion. |
| US6369226B1 (en) | 1999-06-21 | 2002-04-09 | Agouron Pharmaceuticals, Inc. | Substituted benzamide inhibitors of rhinovirus 3C protease |
| DK1206484T3 (da) | 1999-08-04 | 2005-01-24 | Agouron Pharma | Antipicornavirale forbindelser og sammensætninger, deres farmaceutiske anvendelser og materialer til deres syntese |
| 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 |
| HUP0203315A3 (en) | 1999-08-24 | 2003-12-29 | Agouron Pharmaceuticals Inc La | Process and intermediates for the preparation of isoxazolecaroxamides and analogues |
| PE20020157A1 (es) * | 1999-12-03 | 2002-02-22 | Agouron Pharma | Compuestos derivados de piridona como inhibidores de proteasas de picornaviral 3c, composiciones, sus usos farmaceuticos y materiales para su sintesis |
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2001
- 2001-06-13 JP JP2002510441A patent/JP2004503533A/ja active Pending
- 2001-06-13 KR KR1020027017071A patent/KR20030010718A/ko not_active Withdrawn
- 2001-06-13 BR BR0111727-0A patent/BR0111727A/pt not_active IP Right Cessation
- 2001-06-13 NZ NZ523134A patent/NZ523134A/en unknown
- 2001-06-13 CA CA002412618A patent/CA2412618A1/fr not_active Abandoned
- 2001-06-13 EP EP01944519A patent/EP1355878A2/fr not_active Withdrawn
- 2001-06-13 CN CNA018131417A patent/CN1525957A/zh active Pending
- 2001-06-13 US US09/882,345 patent/US6632825B2/en not_active Expired - Fee Related
- 2001-06-13 WO PCT/US2001/019139 patent/WO2001096297A2/fr not_active Ceased
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- 2001-06-13 PL PL01365470A patent/PL365470A1/xx not_active Application Discontinuation
- 2001-06-13 HU HU0301331A patent/HUP0301331A3/hu unknown
- 2001-06-13 AU AU2001266924A patent/AU2001266924A1/en not_active Abandoned
- 2001-06-13 IL IL15343101A patent/IL153431A0/xx unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| AU2001266924A1 (en) | 2001-12-24 |
| WO2001096297A3 (fr) | 2003-07-10 |
| CA2412618A1 (fr) | 2001-12-20 |
| US6989384B2 (en) | 2006-01-24 |
| IL153431A0 (en) | 2003-07-06 |
| US20050080121A1 (en) | 2005-04-14 |
| KR20030010718A (ko) | 2003-02-05 |
| BR0111727A (pt) | 2003-05-27 |
| HUP0301331A3 (en) | 2004-03-01 |
| WO2001096297A2 (fr) | 2001-12-20 |
| CN1525957A (zh) | 2004-09-01 |
| JP2004503533A (ja) | 2004-02-05 |
| US20020061916A1 (en) | 2002-05-23 |
| HUP0301331A2 (hu) | 2003-11-28 |
| MXPA02012456A (es) | 2004-01-26 |
| NZ523134A (en) | 2004-08-27 |
| US6632825B2 (en) | 2003-10-14 |
| EP1355878A2 (fr) | 2003-10-29 |
| PL365470A1 (en) | 2005-01-10 |
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