SK7602002A3 - Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis - Google Patents

Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis Download PDF

Info

Publication number: SK7602002A3
Authority: SK; Slovakia
Prior art keywords: pharmaceutically acceptable; substituted; compound; heterocycloalkyl; group
Prior art date: 1999-12-03

Application number

SK760-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Peter S Dragovich

Thomas J Prins

Ru Zhou

Theodore O Johnson Jr

Original Assignee

Agouron Pharma

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.)

1999-12-03

Filing date

2000-12-01

Publication date

2003-02-04

2000-12-01 Application filed by Agouron Pharma filed Critical Agouron Pharma

2003-02-04 Publication of SK7602002A3 publication Critical patent/SK7602002A3/sk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 293
239000000203 mixture Substances 0.000 title claims description 95
230000015572 biosynthetic process Effects 0.000 title description 15
239000000463 material Substances 0.000 title description 10
238000003786 synthesis reaction Methods 0.000 title description 9
108091005804 Peptidases Proteins 0.000 claims abstract description 27
239000004365 Protease Substances 0.000 claims abstract description 27
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims abstract description 26
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
241001144416 Picornavirales Species 0.000 claims abstract description 19
-1 each R k is H Chemical group 0.000 claims description 198
125000000217 alkyl group Chemical group 0.000 claims description 196
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 147
229910052739 hydrogen Inorganic materials 0.000 claims description 117
125000000753 cycloalkyl group Chemical group 0.000 claims description 106
125000003118 aryl group Chemical group 0.000 claims description 99
150000003839 salts Chemical class 0.000 claims description 99
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 95
125000001424 substituent group Chemical group 0.000 claims description 94
125000001072 heteroaryl group Chemical group 0.000 claims description 83
229940002612 prodrug Drugs 0.000 claims description 72
239000000651 prodrug Substances 0.000 claims description 72
239000012453 solvate Substances 0.000 claims description 71
239000002207 metabolite Substances 0.000 claims description 70
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
125000004429 atom Chemical group 0.000 claims description 44
125000006239 protecting group Chemical group 0.000 claims description 43
150000002367 halogens Chemical class 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 38
229910052736 halogen Inorganic materials 0.000 claims description 38
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
125000004093 cyano group Chemical group *C#N 0.000 claims description 33
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 31
229910052717 sulfur Inorganic materials 0.000 claims description 29
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 28
125000002252 acyl group Chemical group 0.000 claims description 25
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230000000694 effects Effects 0.000 claims description 25
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
125000005129 aryl carbonyl group Chemical group 0.000 claims description 22
229930194542 Keto Natural products 0.000 claims description 21
125000004104 aryloxy group Chemical group 0.000 claims description 21
229910052731 fluorine Inorganic materials 0.000 claims description 21
125000000468 ketone group Chemical group 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
125000000000 cycloalkoxy group Chemical group 0.000 claims description 20
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 19
125000004414 alkyl thio group Chemical group 0.000 claims description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
125000001183 hydrocarbyl group Chemical group 0.000 claims description 19
125000001188 haloalkyl group Chemical group 0.000 claims description 18
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230000002401 inhibitory effect Effects 0.000 claims description 17
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125000004663 dialkyl amino group Chemical group 0.000 claims description 16
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238000003556 assay Methods 0.000 claims description 11
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125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
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125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
125000005323 thioketone group Chemical group 0.000 claims description 9
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125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 8
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 8
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229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 8
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229910052757 nitrogen Inorganic materials 0.000 claims description 7
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
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125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 6
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238000004113 cell culture Methods 0.000 claims description 6
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 6
125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 6
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239000003795 chemical substances by application Substances 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000003981 vehicle Substances 0.000 claims description 4
125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 3
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims 1
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239000000543 intermediate Substances 0.000 abstract description 341
108010091324 3C proteases Proteins 0.000 abstract description 9
230000004071 biological effect Effects 0.000 abstract description 4
238000010189 synthetic method Methods 0.000 abstract description 3
241000709664 Picornaviridae Species 0.000 abstract description 2
238000002360 preparation method Methods 0.000 description 204
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 131
238000000034 method Methods 0.000 description 104
229910052799 carbon Inorganic materials 0.000 description 84
238000006243 chemical reaction Methods 0.000 description 81
241000710122 Rhinovirus B14 Species 0.000 description 72
239000000047 product Substances 0.000 description 69
239000000460 chlorine Substances 0.000 description 67
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239000011541 reaction mixture Substances 0.000 description 59
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 57
239000012267 brine Substances 0.000 description 56
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical compound CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 53
150000001412 amines Chemical class 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
239000011734 sodium Substances 0.000 description 38
150000001408 amides Chemical class 0.000 description 36
238000003818 flash chromatography Methods 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
238000000746 purification Methods 0.000 description 34
239000007787 solid Substances 0.000 description 31
150000003254 radicals Chemical class 0.000 description 30
238000007429 general method Methods 0.000 description 29
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 28
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
150000001732 carboxylic acid derivatives Chemical class 0.000 description 25
230000002829 reductive effect Effects 0.000 description 25
241000700605 Viruses Species 0.000 description 24
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
125000004494 ethyl ester group Chemical group 0.000 description 23
241000710130 Human rhinovirus 1A Species 0.000 description 22
239000002253 acid Substances 0.000 description 22
241000710124 Human rhinovirus A2 Species 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000012074 organic phase Substances 0.000 description 21
231100001274 therapeutic index Toxicity 0.000 description 21
239000003039 volatile agent Substances 0.000 description 21
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238000010992 reflux Methods 0.000 description 20
238000003756 stirring Methods 0.000 description 20
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
XWHHYOYVRVGJJY-QMMMGPOBSA-N 4-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(F)C=C1 XWHHYOYVRVGJJY-QMMMGPOBSA-N 0.000 description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
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241000430519 Human rhinovirus sp. Species 0.000 description 14
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238000010511 deprotection reaction Methods 0.000 description 13
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239000000706 filtrate Substances 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
238000010828 elution Methods 0.000 description 11
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241001635223 Coxsackievirus B2 Species 0.000 description 10
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238000012360 testing method Methods 0.000 description 10
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238000005755 formation reaction Methods 0.000 description 9
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
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125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
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208000015181 infectious disease Diseases 0.000 description 8
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
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239000007821 HATU Substances 0.000 description 7
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JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 6
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230000008569 process Effects 0.000 description 6
238000010926 purge Methods 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
WRHZVMBBRYBTKZ-UHFFFAOYSA-N pyrrole-2-carboxylic acid Chemical compound OC(=O)C1=CC=CN1 WRHZVMBBRYBTKZ-UHFFFAOYSA-N 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
ZENPTSOBLDIRGR-UHFFFAOYSA-N (2-oxo-1h-pyridin-3-yl)carbamic acid Chemical compound OC(=O)NC1=CC=CNC1=O ZENPTSOBLDIRGR-UHFFFAOYSA-N 0.000 description 5
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238000011049 filling Methods 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
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239000012458 free base Substances 0.000 description 1
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238000005462 in vivo assay Methods 0.000 description 1
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239000011630 iodine Substances 0.000 description 1
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229910052742 iron Inorganic materials 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
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
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CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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235000019359 magnesium stearate Nutrition 0.000 description 1
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229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
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JSVBFZVPQSPVQR-UHFFFAOYSA-N methyl 5-naphthalen-1-yl-1h-pyrrole-2-carboxylate Chemical compound N1C(C(=O)OC)=CC=C1C1=CC=CC2=CC=CC=C12 JSVBFZVPQSPVQR-UHFFFAOYSA-N 0.000 description 1
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WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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SEOYNUHKXVGWFU-UHFFFAOYSA-N mu-oxidobis(oxidonitrogen) Chemical compound O=NON=O SEOYNUHKXVGWFU-UHFFFAOYSA-N 0.000 description 1
YYTWEEOFRNSTKS-UHFFFAOYSA-N n,n'-dicyclohexylmethanediimine;1-hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1.C1CCCCC1N=C=NC1CCCCC1 YYTWEEOFRNSTKS-UHFFFAOYSA-N 0.000 description 1
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125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
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GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
MJEZWXIDVVZMOU-UHFFFAOYSA-N tert-butyl 3-(2-hydroxyethyl)-5-iodo-4-methyl-1h-pyrrole-2-carboxylate Chemical compound CC1=C(I)NC(C(=O)OC(C)(C)C)=C1CCO MJEZWXIDVVZMOU-UHFFFAOYSA-N 0.000 description 1
REMFHRHKMGNSHZ-UHFFFAOYSA-N tert-butyl 5-iodo-4-methyl-3-(2-oxoethyl)-1h-pyrrole-2-carboxylate Chemical compound CC1=C(I)NC(C(=O)OC(C)(C)C)=C1CC=O REMFHRHKMGNSHZ-UHFFFAOYSA-N 0.000 description 1
FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
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CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
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IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 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
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
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GDJZZWYLFXAGFH-UHFFFAOYSA-M xylenesulfonate group Chemical group C1(C(C=CC=C1)C)(C)S(=O)(=O)[O-] GDJZZWYLFXAGFH-UHFFFAOYSA-M 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- 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
- 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
- C07D405/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur 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
- 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
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- 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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (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)
Oncology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Peptides Or Proteins (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Enzymes And Modification Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK760-2002A 1999-12-03 2000-12-01 Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis SK7602002A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US16898699P	1999-12-03	1999-12-03
US19205200P	2000-03-24	2000-03-24
PCT/US2000/032621 WO2001040189A1 (fr)	1999-12-03	2000-12-01	Composes et compositions anti-picornavirus; utilisations pharmaceutiques et materiaux employes pour leur synthese

Publications (1)

Publication Number	Publication Date
SK7602002A3 true SK7602002A3 (en)	2003-02-04

Family

ID=26864652

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK760-2002A SK7602002A3 (en)	1999-12-03	2000-12-01	Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis

Country Status (31)

Country	Link
US (1)	US6514997B2 (fr)
EP (1)	EP1252145A1 (fr)
JP (1)	JP2003515591A (fr)
KR (1)	KR20020058076A (fr)
CN (1)	CN1402710A (fr)
AP (1)	AP2002002510A0 (fr)
AR (1)	AR030540A1 (fr)
AU (1)	AU777943B2 (fr)
BG (1)	BG106754A (fr)
BR (1)	BR0016742A (fr)
CA (1)	CA2392504A1 (fr)
CO (1)	CO5261566A1 (fr)
CZ (1)	CZ20021906A3 (fr)
DO (1)	DOP2000000108A (fr)
EA (1)	EA200200625A1 (fr)
EE (1)	EE200200281A (fr)
HK (1)	HK1052933A1 (fr)
HU (1)	HUP0204006A3 (fr)
IL (1)	IL149427A0 (fr)
IS (1)	IS6378A (fr)
MX (1)	MXPA02005124A (fr)
NO (1)	NO20022589L (fr)
NZ (1)	NZ518934A (fr)
OA (1)	OA12101A (fr)
PA (1)	PA8507801A1 (fr)
PE (1)	PE20020157A1 (fr)
PL (1)	PL356062A1 (fr)
SK (1)	SK7602002A3 (fr)
UY (1)	UY26465A1 (fr)
WO (1)	WO2001040189A1 (fr)
YU (1)	YU40002A (fr)

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WO2004093860A1 (fr) *	2003-04-21	2004-11-04	Pfizer Inc.	Inhibiteurs de proteinase de coronavirus apparente au virus du sras
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JP2023522990A (ja) *	2020-04-23	2023-06-01	パーデュー・リサーチ・ファウンデーション	Ｓａｒｓの治療のための化合物
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2000
- 2000-11-30 PA PA20008507801A patent/PA8507801A1/es unknown
- 2000-11-30 PE PE2000001276A patent/PE20020157A1/es not_active Application Discontinuation
- 2000-12-01 EP EP00980893A patent/EP1252145A1/fr not_active Withdrawn
- 2000-12-01 WO PCT/US2000/032621 patent/WO2001040189A1/fr not_active Ceased
- 2000-12-01 AP APAP/P/2002/002510A patent/AP2002002510A0/en unknown
- 2000-12-01 JP JP2001541874A patent/JP2003515591A/ja not_active Withdrawn
- 2000-12-01 HK HK03104911.5A patent/HK1052933A1/zh unknown
- 2000-12-01 UY UY26465A patent/UY26465A1/es not_active Application Discontinuation
- 2000-12-01 EE EEP200200281A patent/EE200200281A/xx unknown
- 2000-12-01 CZ CZ20021906A patent/CZ20021906A3/cs unknown
- 2000-12-01 AU AU18094/01A patent/AU777943B2/en not_active Ceased
- 2000-12-01 US US09/726,376 patent/US6514997B2/en not_active Expired - Fee Related
- 2000-12-01 DO DO2000000108A patent/DOP2000000108A/es unknown
- 2000-12-01 YU YU40002A patent/YU40002A/sh unknown
- 2000-12-01 IL IL14942700A patent/IL149427A0/xx unknown
- 2000-12-01 NZ NZ518934A patent/NZ518934A/en unknown
- 2000-12-01 KR KR1020027007099A patent/KR20020058076A/ko not_active Withdrawn
- 2000-12-01 OA OA1200200160A patent/OA12101A/en unknown
- 2000-12-01 HU HU0204006A patent/HUP0204006A3/hu unknown
- 2000-12-01 EA EA200200625A patent/EA200200625A1/ru unknown
- 2000-12-01 CA CA002392504A patent/CA2392504A1/fr not_active Abandoned
- 2000-12-01 MX MXPA02005124A patent/MXPA02005124A/es not_active Application Discontinuation
- 2000-12-01 BR BR0016742-8A patent/BR0016742A/pt not_active IP Right Cessation
- 2000-12-01 PL PL00356062A patent/PL356062A1/xx not_active Application Discontinuation
- 2000-12-01 SK SK760-2002A patent/SK7602002A3/sk unknown
- 2000-12-01 CN CN00816602A patent/CN1402710A/zh active Pending
- 2000-12-04 CO CO00092264A patent/CO5261566A1/es not_active Application Discontinuation
- 2000-12-04 AR ARP000106412A patent/AR030540A1/es unknown
2002
- 2002-05-10 IS IS6378A patent/IS6378A/is unknown
- 2002-05-30 BG BG106754A patent/BG106754A/bg unknown
- 2002-05-31 NO NO20022589A patent/NO20022589L/no unknown

Also Published As

Publication number	Publication date
AU777943B2 (en)	2004-11-04
IL149427A0 (en)	2002-11-10
HUP0204006A3 (en)	2004-11-29
DOP2000000108A (es)	2003-03-15
WO2001040189A1 (fr)	2001-06-07
JP2003515591A (ja)	2003-05-07
PE20020157A1 (es)	2002-02-22
UY26465A1 (es)	2001-06-29
MXPA02005124A (es)	2003-01-28
KR20020058076A (ko)	2002-07-12
BR0016742A (pt)	2002-09-03
NZ518934A (en)	2003-11-28
US6514997B2 (en)	2003-02-04
IS6378A (is)	2002-05-10
EE200200281A (et)	2003-06-16
NO20022589D0 (no)	2002-05-31
EA200200625A1 (ru)	2002-12-26
YU40002A (sh)	2006-01-16
BG106754A (bg)	2003-07-31
HUP0204006A2 (hu)	2003-03-28
CO5261566A1 (es)	2003-03-31
AR030540A1 (es)	2003-08-27
HK1052933A1 (zh)	2003-10-03
PA8507801A1 (es)	2002-08-26
AP2002002510A0 (en)	2002-06-30
EP1252145A1 (fr)	2002-10-30
US20010047006A1 (en)	2001-11-29
OA12101A (en)	2006-05-04
PL356062A1 (en)	2004-06-14
AU1809401A (en)	2001-06-12
CN1402710A (zh)	2003-03-12
NO20022589L (no)	2002-07-31
CZ20021906A3 (cs)	2003-02-12
CA2392504A1 (fr)	2001-06-07

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