AU2001251315A1 - Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the coagulation cascade - Google Patents
Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the coagulation cascadeInfo
- Publication number
- AU2001251315A1 AU2001251315A1 AU2001251315A AU5131501A AU2001251315A1 AU 2001251315 A1 AU2001251315 A1 AU 2001251315A1 AU 2001251315 A AU2001251315 A AU 2001251315A AU 5131501 A AU5131501 A AU 5131501A AU 2001251315 A1 AU2001251315 A1 AU 2001251315A1
- Authority
- AU
- Australia
- Prior art keywords
- group
- carbon
- amino
- hydrido
- attachment
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 125000001072 heteroaryl group Chemical group 0.000 title claims 106
- MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical class O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 title claims 9
- 230000015271 coagulation Effects 0.000 title 1
- 238000005345 coagulation Methods 0.000 title 1
- 230000005764 inhibitory process Effects 0.000 title 1
- -1 hydrido, amidino, guanidino Chemical group 0.000 claims 1784
- 229910052799 carbon Inorganic materials 0.000 claims 699
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 539
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 321
- 125000004429 atom Chemical group 0.000 claims 210
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 188
- 125000000217 alkyl group Chemical group 0.000 claims 177
- 229910052757 nitrogen Inorganic materials 0.000 claims 171
- 229910052760 oxygen Inorganic materials 0.000 claims 163
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 162
- 125000001188 haloalkyl group Chemical group 0.000 claims 134
- 229910052717 sulfur Inorganic materials 0.000 claims 131
- 125000004093 cyano group Chemical group *C#N 0.000 claims 123
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 119
- 125000005843 halogen group Chemical group 0.000 claims 110
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 106
- 125000003282 alkyl amino group Chemical group 0.000 claims 105
- 125000003545 alkoxy group Chemical group 0.000 claims 97
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 95
- 125000006850 spacer group Chemical group 0.000 claims 89
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 85
- 125000000623 heterocyclic group Chemical group 0.000 claims 84
- 125000004103 aminoalkyl group Chemical group 0.000 claims 68
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 67
- 125000001153 fluoro group Chemical group F* 0.000 claims 62
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 58
- 125000004438 haloalkoxy group Chemical group 0.000 claims 58
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 56
- 125000004414 alkyl thio group Chemical group 0.000 claims 55
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 54
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 52
- 150000001875 compounds Chemical class 0.000 claims 52
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 50
- 125000001309 chloro group Chemical group Cl* 0.000 claims 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims 47
- 125000004663 dialkyl amino group Chemical group 0.000 claims 45
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 45
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 45
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 44
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 44
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 43
- 150000003839 salts Chemical class 0.000 claims 43
- 125000003342 alkenyl group Chemical group 0.000 claims 41
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 38
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 38
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 36
- 125000005518 carboxamido group Chemical group 0.000 claims 34
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 33
- 125000000033 alkoxyamino group Chemical group 0.000 claims 33
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 33
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 32
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 31
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 30
- 125000003118 aryl group Chemical group 0.000 claims 30
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 30
- 125000001246 bromo group Chemical group Br* 0.000 claims 29
- 125000000262 haloalkenyl group Chemical group 0.000 claims 29
- 125000004995 haloalkylthio group Chemical group 0.000 claims 29
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims 28
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 27
- 125000003435 aroyl group Chemical group 0.000 claims 27
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 26
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 26
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 26
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 26
- 125000001589 carboacyl group Chemical group 0.000 claims 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 25
- 150000001721 carbon Chemical group 0.000 claims 25
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 25
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 22
- 229930192474 thiophene Natural products 0.000 claims 22
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 21
- 125000000304 alkynyl group Chemical group 0.000 claims 21
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims 21
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 21
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 20
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims 19
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 18
- SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims 18
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 18
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 18
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 18
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 17
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 17
- 125000004104 aryloxy group Chemical group 0.000 claims 17
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 16
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 16
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 16
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 16
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims 16
- 125000001769 aryl amino group Chemical group 0.000 claims 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 15
- 125000005241 heteroarylamino group Chemical group 0.000 claims 15
- 239000001301 oxygen Substances 0.000 claims 15
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 14
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 14
- 239000011593 sulfur Substances 0.000 claims 14
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 13
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 13
- 241000124008 Mammalia Species 0.000 claims 13
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 13
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 13
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 13
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 13
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 13
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 13
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 12
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 12
- 125000002252 acyl group Chemical group 0.000 claims 12
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 12
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 12
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 12
- 125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims 12
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 12
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 12
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 12
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 12
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 11
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 11
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 11
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 11
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims 11
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 11
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 11
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 11
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 11
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 10
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 10
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims 10
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 10
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 10
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 10
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 10
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 10
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 9
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 9
- 101100001676 Emericella variicolor andK gene Proteins 0.000 claims 9
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 9
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 9
- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims 9
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 9
- 210000004369 blood Anatomy 0.000 claims 9
- 239000008280 blood Substances 0.000 claims 9
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 9
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 9
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 9
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 9
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 9
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 8
- 125000004175 fluorobenzyl group Chemical group 0.000 claims 8
- 125000006769 halocycloalkoxy group Chemical group 0.000 claims 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 8
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 8
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 8
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 7
- 125000004423 acyloxy group Chemical group 0.000 claims 7
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 125000005110 aryl thio group Chemical group 0.000 claims 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 7
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 6
- 208000007536 Thrombosis Diseases 0.000 claims 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 6
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 6
- 230000002401 inhibitory effect Effects 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 6
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims 5
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 claims 5
- 125000006024 2-pentenyl group Chemical group 0.000 claims 5
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 5
- 101100001675 Emericella variicolor andJ gene Proteins 0.000 claims 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 5
- 125000005354 acylalkyl group Chemical group 0.000 claims 5
- 125000004442 acylamino group Chemical group 0.000 claims 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 5
- 125000005466 alkylenyl group Chemical group 0.000 claims 5
- 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 claims 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 5
- DMEKUKDWAIXWSL-UHFFFAOYSA-N n,n-dimethyl-7-nitro-9h-fluoren-2-amine Chemical compound [O-][N+](=O)C1=CC=C2C3=CC=C(N(C)C)C=C3CC2=C1 DMEKUKDWAIXWSL-UHFFFAOYSA-N 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- DRTMJRDGJNCYEA-UHFFFAOYSA-N (2-amino-2-iminoethyl)-(diaminomethylideneamino)-methylsulfanium Chemical compound C(N)(=N)C[S+](C)NC(=N)N DRTMJRDGJNCYEA-UHFFFAOYSA-N 0.000 claims 4
- 125000006040 2-hexenyl group Chemical group 0.000 claims 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 4
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 4
- 125000006041 3-hexenyl group Chemical group 0.000 claims 4
- 125000006042 4-hexenyl group Chemical group 0.000 claims 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 4
- WXEHBUMAEPOYKP-UHFFFAOYSA-N methylsulfanylethane Chemical compound CCSC WXEHBUMAEPOYKP-UHFFFAOYSA-N 0.000 claims 4
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 claims 3
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 claims 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 3
- 125000003974 3-carbamimidamidopropyl group Chemical group C(N)(=N)NCCC* 0.000 claims 3
- 125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 claims 3
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 claims 3
- 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims 3
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 3
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 3
- 125000006519 CCH3 Chemical group 0.000 claims 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 3
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 3
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims 3
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 3
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 3
- 125000005368 heteroarylthio group Chemical group 0.000 claims 3
- 125000004468 heterocyclylthio group Chemical group 0.000 claims 3
- 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 3
- YWWDBCBWQNCYNR-UHFFFAOYSA-O trimethylphosphanium Chemical compound C[PH+](C)C YWWDBCBWQNCYNR-UHFFFAOYSA-O 0.000 claims 3
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 2
- 125000006017 1-propenyl group Chemical group 0.000 claims 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 claims 2
- 125000006043 5-hexenyl group Chemical group 0.000 claims 2
- 208000005189 Embolism Diseases 0.000 claims 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- QJGQUHMNIGDVPM-BJUDXGSMSA-N Nitrogen-13 Chemical compound [13N] QJGQUHMNIGDVPM-BJUDXGSMSA-N 0.000 claims 2
- 208000001435 Thromboembolism Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 claims 2
- 125000004967 formylalkyl group Chemical group 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 230000001732 thrombotic effect Effects 0.000 claims 2
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 claims 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 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
- 206010002388 Angina unstable Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims 1
- 206010051055 Deep vein thrombosis Diseases 0.000 claims 1
- 206010014498 Embolic stroke Diseases 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 206010047249 Venous thrombosis Diseases 0.000 claims 1
- WRWYGOVGIGCDLE-UHFFFAOYSA-N [O]c1ccccc1F Chemical group [O]c1ccccc1F WRWYGOVGIGCDLE-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 210000001772 blood platelet Anatomy 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 230000001269 cardiogenic effect Effects 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002319 fibrinogen receptor antagonist Substances 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
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
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19485100P | 2000-04-05 | 2000-04-05 | |
| US60194851 | 2000-04-05 | ||
| US25203100P | 2000-11-20 | 2000-11-20 | |
| US60252031 | 2000-11-20 | ||
| PCT/US2001/011014 WO2001077079A2 (fr) | 2000-04-05 | 2001-04-04 | Pyridones polycycliques 4-aryl et heteroaryl substituees utiles pour l'inhibition selective de la cascade de coagulation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001251315A1 true AU2001251315A1 (en) | 2001-10-23 |
Family
ID=26890461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001251315A Abandoned AU2001251315A1 (en) | 2000-04-05 | 2001-04-04 | Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the coagulation cascade |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6693121B2 (fr) |
| EP (1) | EP1268428A2 (fr) |
| JP (1) | JP2004505013A (fr) |
| AU (1) | AU2001251315A1 (fr) |
| CA (1) | CA2405306A1 (fr) |
| WO (1) | WO2001077079A2 (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030236257A1 (en) * | 2001-04-04 | 2003-12-25 | South Michael S. | Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the cogulation cascade |
| MXPA04003163A (es) * | 2001-10-03 | 2004-07-08 | Pharmacia Corp | Compuestos heterociclicos de 6 elementos utiles para inhibicion selectiva de la casdada de coagulacion. |
| CN113698386B (zh) * | 2020-05-22 | 2022-12-27 | 上海美悦生物科技发展有限公司 | 一种4(1h)-吡啶酮类化合物、其药物组合物和用途 |
Family Cites Families (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5910541A (ja) | 1982-07-09 | 1984-01-20 | Takeda Chem Ind Ltd | キノン化合物 |
| JPS60255749A (ja) | 1984-05-31 | 1985-12-17 | Univ Nagoya | キノン誘導体 |
| US5304658A (en) | 1984-08-01 | 1994-04-19 | Takeda Chemical Industries, Ltd. | Quinone derivatives, their production and use |
| IL81264A (en) | 1986-01-30 | 1990-11-05 | Takeda Chemical Industries Ltd | Quinone derivatives,their production and pharmaceutical compositions containing them |
| DE3826846A1 (de) | 1988-08-06 | 1990-02-08 | Goedecke Ag | Alkoxy-4(1h)-pyridon-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel |
| US5008267A (en) | 1988-10-29 | 1991-04-16 | Mitsui Toatsu Chemicals, Incorporated | Pyrimidinedione compounds, method of producing the same and antiarrythmic agents containing the same |
| GB9216272D0 (en) | 1991-08-15 | 1992-09-09 | Ici Plc | Substituted heterocycles |
| US5441960A (en) | 1992-04-16 | 1995-08-15 | Zeneca Limited | 1-pyrimidinylacetamide human leukocyte elastate inhibitors |
| DE69314169T2 (de) | 1992-04-16 | 1998-01-15 | Zeneca Ltd | Peptide mit eine alphaaminoboronaire gruppe and ihre verwendung als elastasehemmer |
| US5618792A (en) | 1994-11-21 | 1997-04-08 | Cortech, Inc. | Substituted heterocyclic compounds useful as inhibitors of (serine proteases) human neutrophil elastase |
| MX9704439A (es) | 1994-12-13 | 1997-10-31 | Corvas Int Inc | Derivados heterociclicos aromaticos como inhibidores de enzima. |
| US6011158A (en) | 1994-12-13 | 2000-01-04 | Corvas International, Inc. | Aromatic heterocyclic derivatives as enzyme inhibitors |
| US5658930A (en) | 1994-12-13 | 1997-08-19 | Corvas International, Inc. | Aromatic heterocyclic derivatives as enzyme inhibitors |
| US5656645A (en) | 1994-12-13 | 1997-08-12 | Corvas International, Inc. | Aromatic heterocyclic derivatives as enzyme inhibitors |
| KR100400639B1 (ko) | 1995-04-27 | 2003-12-31 | 미쯔비시 웰 파마 가부시키가이샤 | 복소환식아미드화합물및그의의약용도 |
| US5612378A (en) | 1995-06-06 | 1997-03-18 | 3-Dimensional Pharmaceuticals, Inc. | Bis-arylsulfonylaminobenzamide derivatives and the use thereof as factor Xa inhibitors |
| US5741819A (en) | 1995-06-07 | 1998-04-21 | 3-Dimensional Pharmaceuticals, Inc. | Arylsulfonylaminobenzene derivatives and the use thereof as factor Xa inhibitors |
| AU703744B2 (en) * | 1995-06-27 | 1999-04-01 | Merck & Co., Inc. | Pyridinone-thrombin inhibitors |
| US5964154A (en) | 1995-11-08 | 1999-10-12 | Koenig & Bauer-Albert Aktiengesellschaft | Folding device |
| AU720616B2 (en) | 1996-02-22 | 2000-06-08 | Merck & Co., Inc. | Pyridinone thrombin inhibitors |
| WO1997040024A1 (fr) | 1996-04-23 | 1997-10-30 | Merck & Co., Inc. | Inhibiteurs de thrombine a base de pyrazinone |
| US5668289A (en) | 1996-06-24 | 1997-09-16 | Merck & Co., Inc. | Pyridinone thrombin inhibitors |
| EP0934305A4 (fr) | 1996-08-29 | 2001-04-11 | Merck & Co Inc | Antagonistes de l'integrine |
| KR20000068354A (ko) | 1996-09-06 | 2000-11-25 | 다께다 가즈히꼬 | 신규 아세트아미드 유도체 및 프로테아제 저해제 |
| AU4172397A (en) | 1996-09-06 | 1998-03-26 | Biochem Pharma Inc. | Lactam inhibitors of thrombin |
| WO1998010763A1 (fr) | 1996-09-13 | 1998-03-19 | Merck & Co., Inc. | Inhibiteurs de thrombine |
| US5872138A (en) | 1996-09-13 | 1999-02-16 | Merck & Co., Inc. | Thrombin inhibitors |
| CA2268264A1 (fr) | 1996-10-11 | 1998-04-23 | Cor Therapeutics, Inc. | Inhibiteurs selectifs du facteur xa |
| CA2268381A1 (fr) | 1996-10-11 | 1998-04-23 | Cor Therapeutics, Inc. | Inhibiteurs selectifs du facteur xa |
| US5869487A (en) | 1996-10-24 | 1999-02-09 | Merck & Co., Inc. | Pyrido 3,4-B!pyrazines for use as thrombin inhibitors |
| EP0940400A4 (fr) | 1996-10-25 | 2002-10-02 | Mitsubishi Pharma Corp | Nouveaux composes d'amide heterocycliques et leur utilisation a des fins medicinales |
| AU722429B2 (en) | 1997-01-22 | 2000-08-03 | Merck & Co., Inc. | Thrombin inhibitors |
| US5792779A (en) | 1997-02-19 | 1998-08-11 | Merck & Co., Inc. | Pyridinone thrombin inhibitors |
| JP2001518932A (ja) | 1997-03-24 | 2001-10-16 | メルク エンド カンパニー インコーポレーテッド | トロンビン阻害薬 |
| US5866573A (en) | 1997-04-21 | 1999-02-02 | Merck & Co., Inc. | Pyrazinone thrombin inhibitors |
| IL123986A (en) | 1997-04-24 | 2011-10-31 | Organon Nv | Medicinal compounds |
| RU2183642C2 (ru) | 1997-05-02 | 2002-06-20 | Акцо Нобель Н.В. | Ингибиторы сериновых протеаз |
| WO1999000126A1 (fr) | 1997-06-26 | 1999-01-07 | Eli Lilly And Company | Agents antithrombotiques |
| CA2294240A1 (fr) | 1997-06-26 | 1999-01-07 | Trelia Joyce Craft | Agents antithrombotiques |
| CA2294042A1 (fr) | 1997-06-26 | 1999-01-07 | David Kent Herron | Agents antithrombotiques |
| JP2001514227A (ja) | 1997-09-05 | 2001-09-11 | メルク エンド カムパニー インコーポレーテッド | ピラジノン系トロンビン阻害薬 |
| AU1605699A (en) | 1997-11-26 | 1999-06-15 | Corvas International, Inc. | Substituted 3-amino-2-hydroxyphenylacetamide derivatives as enzyme inhibitors (ii) |
| JP2001524467A (ja) | 1997-11-26 | 2001-12-04 | ３−ディメンショナル ファーマシューティカルズ， インコーポレイテッド | ヘテロアリールアミノグアニジンおよびアルコキシグアニジンおよびプロテアーゼインヒビターとしてのこれらの使用 |
| PT1049703E (pt) | 1998-01-20 | 2003-06-30 | Warner Lambert Co | Aldeido do acido n-¬2-(5-benziloxicarbonilamino-6-oxo-2-(4-fluorofenil)-1,6-di-hidro-1-pirimidinil)acetoxil|-l-aspartico como inibidor da enzima de conversao da interleucina-1beta in vivo |
| WO1999043660A1 (fr) | 1998-02-26 | 1999-09-02 | Neurogen Corporation | Carboxamides 1,4-dihydro-4-oxonicotiniques substitues; ligands des recepteurs gaba du cerveau |
| GB9806102D0 (en) | 1998-03-20 | 1998-05-20 | Merck Sharp & Dohme | Therapeutic agents |
| AU753479B2 (en) | 1998-05-19 | 2002-10-17 | Merck & Co., Inc. | Pyrazinone thrombin inhibitors |
| AU742178B2 (en) | 1998-05-26 | 2001-12-20 | Merck & Co., Inc. | Imidazopyridine thrombin inhibitors |
| WO2000032216A1 (fr) | 1998-06-03 | 2000-06-08 | Cortech Inc. | Peptoide et non-peptoide contenant des exadiaoles alpha-ceto et utilises comme inhibiteurs de protease serine |
| AU759427B2 (en) | 1998-06-11 | 2003-04-17 | 3-Dimensional Pharmaceuticals, Inc. | Pyrazinone protease inhibitors |
| ES2209337T3 (es) | 1998-08-14 | 2004-06-16 | Pfizer Inc. | Agentes antitromboticos. |
| CA2343109A1 (fr) | 1998-09-28 | 2000-04-06 | Merck & Co., Inc. | Inhibiteurs de la thrombine |
| EP1124822A4 (fr) | 1998-10-30 | 2002-04-03 | Merck & Co Inc | Inhibiteurs de la thrombine |
| JP2002528542A (ja) | 1998-10-30 | 2002-09-03 | メルク エンド カムパニー インコーポレーテッド | トロンビン阻害剤 |
| DE19851421A1 (de) | 1998-11-07 | 2000-05-11 | Boehringer Ingelheim Pharma | Neue Pyrimidine, deren Herstellung und Verwendung |
| FR2786482B1 (fr) | 1998-11-27 | 2002-08-09 | Synthelabo | Nouveaux derives de 2-pyridone, leur preparation et leur application en therapeutique |
| EP1058549A4 (fr) | 1998-12-23 | 2003-11-12 | Bristol Myers Squibb Pharma Co | INHIBITEURS DU FACTEUR Xa OU DE LA THROMBINE |
| EP1178971A1 (fr) | 1999-05-19 | 2002-02-13 | Pharmacia Corporation | Anticoagulants a base d'uracils d'aryle polycycliques et d'heteroaryles |
| SK15852001A3 (sk) | 1999-05-19 | 2003-06-03 | Pharmacia Corporation | Substituované polycyklické arylové a heteroarylové pyrimidinóny použiteľné ako antikoagulanty |
| MXPA01011805A (es) | 1999-05-19 | 2003-09-04 | Pharmacia Corp | Aril y heteroaril piridonas policiclicas, substituidas utiles para la inhibicion selectiva de la cascada de coagulacion. |
| WO2002042272A2 (fr) * | 2000-11-20 | 2002-05-30 | Pharmacia Corporation | Aryl-et-heteroaryl-pyridines polycycliques substituees utiles dans l'inhibition selective de la cascade de la coagulation |
-
2001
- 2001-04-04 US US09/826,433 patent/US6693121B2/en not_active Expired - Fee Related
- 2001-04-04 EP EP01924684A patent/EP1268428A2/fr not_active Withdrawn
- 2001-04-04 JP JP2001575554A patent/JP2004505013A/ja not_active Withdrawn
- 2001-04-04 WO PCT/US2001/011014 patent/WO2001077079A2/fr not_active Application Discontinuation
- 2001-04-04 CA CA002405306A patent/CA2405306A1/fr not_active Abandoned
- 2001-04-04 AU AU2001251315A patent/AU2001251315A1/en not_active Abandoned
-
2004
- 2004-02-02 US US10/770,384 patent/US20040162319A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2405306A1 (fr) | 2001-10-18 |
| WO2001077079A3 (fr) | 2002-04-11 |
| US20020032174A1 (en) | 2002-03-14 |
| WO2001077079A2 (fr) | 2001-10-18 |
| US20040162319A1 (en) | 2004-08-19 |
| EP1268428A2 (fr) | 2003-01-02 |
| JP2004505013A (ja) | 2004-02-19 |
| US6693121B2 (en) | 2004-02-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6624180B2 (en) | Substituted polycyclic aryl and heteroaryl pyridines useful for selective inhibition of the coagulation cascade | |
| US20050165021A1 (en) | Polycyclic aryl and heteroaryl substituted 4-pyrones useful for selective inhibition of the coagulation cascade | |
| US6852761B2 (en) | Polycyclic aryl and heteroaryl substituted benzenes useful for selective inhibition of the coagulation cascade | |
| US20040116430A1 (en) | Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade | |
| US6686484B2 (en) | Polycyclic aryl and heteroaryl substituted 1,4-quinones useful for selective inhibition of the coagulation cascade | |
| US7015230B1 (en) | Substituted polycyclic aryl and heteroaryl uracils useful for selective inhibition of the coagulation cascade | |
| WO2001087852A1 (fr) | Uracils d'heteroaryle et d'aryle polycycliques substitues utiles pour l'inhibition selective de la cascade de coagulation | |
| US6693121B2 (en) | Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the coagulation cascade | |
| WO2001087851A1 (fr) | Aryle polycyclique substitue et pyrimidinones d'heteroaryle utiles a l'inhibition selective de la coagulation | |
| US20030236257A1 (en) | Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the cogulation cascade | |
| US20040068113A1 (en) | Substituted polycyclic aryl and heteroaryl pyridines useful for selective inhibition of the coagulation cascade | |
| AU2002226902A1 (en) | Substituted polycyclic aryl and heteroaryl pyridines useful for selective inhibition of the coagulation cascade |