TWI222445B - Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade - Google Patents

Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade Download PDF

Info

Publication number: TWI222445B
Authority: TW; Taiwan
Prior art keywords: group; butyl; alkyl; scope; patent application
Prior art date: 1999-05-19

Application number

TW089109595A

Other languages

English (en)

Chinese (zh)

Inventor

Michael S South

Ashton T Hamme

William Neumann

Darin E Jones

Melvin L Rueppel

Original Assignee

Pharmacia Corp

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.)

1999-05-19

Filing date

2000-07-25

Publication date

2004-10-21

2000-07-25 Application filed by Pharmacia Corp filed Critical Pharmacia Corp

2004-10-21 Application granted granted Critical

2004-10-21 Publication of TWI222445B publication Critical patent/TWI222445B/zh

Links

-1 heteroaryl pyrimidinones Chemical class 0.000 title claims abstract description 749
230000015271 coagulation Effects 0.000 title abstract description 15
238000005345 coagulation Methods 0.000 title abstract description 15
230000005764 inhibitory process Effects 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 125
239000000203 mixture Substances 0.000 claims abstract description 47
238000011282 treatment Methods 0.000 claims abstract description 21
239000003146 anticoagulant agent Substances 0.000 claims abstract description 12
230000001732 thrombotic effect Effects 0.000 claims abstract description 8
230000002265 prevention Effects 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 237
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 104
150000001412 amines Chemical class 0.000 claims description 100
125000003545 alkoxy group Chemical group 0.000 claims description 99
229910052717 sulfur Inorganic materials 0.000 claims description 78
125000003282 alkyl amino group Chemical group 0.000 claims description 59
150000003839 salts Chemical class 0.000 claims description 54
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 47
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
125000003277 amino group Chemical group 0.000 claims description 35
125000004076 pyridyl group Chemical group 0.000 claims description 34
125000001424 substituent group Chemical group 0.000 claims description 29
239000011593 sulfur Substances 0.000 claims description 27
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
241000124008 Mammalia Species 0.000 claims description 20
230000015572 biosynthetic process Effects 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 20
208000007536 Thrombosis Diseases 0.000 claims description 19
239000008280 blood Substances 0.000 claims description 18
210000004369 blood Anatomy 0.000 claims description 18
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 14
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 description 12
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
230000002401 inhibitory effect Effects 0.000 claims description 11
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 10
208000024891 symptom Diseases 0.000 claims description 10
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
208000004998 Abdominal Pain Diseases 0.000 claims description 8
208000002881 Colic Diseases 0.000 claims description 8
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
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 description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
241000282412 Homo Species 0.000 claims description 6
206010038743 Restlessness Diseases 0.000 claims description 6
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 description 6
230000002792 vascular Effects 0.000 claims description 6
206010047249 Venous thrombosis Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
206010051055 Deep vein thrombosis Diseases 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
208000005189 Embolism Diseases 0.000 claims description 3
230000000747 cardiac effect Effects 0.000 claims description 3
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 3
229910052737 gold Inorganic materials 0.000 claims description 3
239000010931 gold Substances 0.000 claims description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
241000894007 species Species 0.000 claims description 3
230000002685 pulmonary effect Effects 0.000 claims description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
230000002537 thrombolytic effect Effects 0.000 claims description 2
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 14
125000001544 thienyl group Chemical group 0.000 claims 5
206010028980 Neoplasm Diseases 0.000 claims 4
201000011510 cancer Diseases 0.000 claims 4
125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 claims 3
125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 claims 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
206010014522 Embolism venous Diseases 0.000 claims 2
238000002512 chemotherapy Methods 0.000 claims 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 2
208000004043 venous thromboembolism Diseases 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 claims 1
125000002124 5'-adenosyl group Chemical group N1=CN=C2N(C=NC2=C1N)[C@H]1[C@H](O)[C@H](O)[C@H](O1)C* 0.000 claims 1
206010048620 Intracardiac thrombus Diseases 0.000 claims 1
208000010378 Pulmonary Embolism Diseases 0.000 claims 1
208000001435 Thromboembolism Diseases 0.000 claims 1
238000009534 blood test Methods 0.000 claims 1
125000002073 methionyl group Chemical group 0.000 claims 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
230000009466 transformation Effects 0.000 claims 1
238000000034 method Methods 0.000 abstract description 26
239000003112 inhibitor Substances 0.000 abstract description 11
229940127219 anticoagulant drug Drugs 0.000 abstract description 9
208000026106 cerebrovascular disease Diseases 0.000 abstract description 8
208000029078 coronary artery disease Diseases 0.000 abstract description 8
238000002560 therapeutic procedure Methods 0.000 abstract description 7
108010022999 Serine Proteases Proteins 0.000 abstract description 6
102000012479 Serine Proteases Human genes 0.000 abstract description 6
210000004351 coronary vessel Anatomy 0.000 abstract description 4
229910052799 carbon Inorganic materials 0.000 description 305
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 212
125000004435 hydrogen atom Chemical class [H]* 0.000 description 170
239000001257 hydrogen Substances 0.000 description 157
229910052739 hydrogen Inorganic materials 0.000 description 157
229910052757 nitrogen Inorganic materials 0.000 description 142
239000002585 base Substances 0.000 description 140
238000011049 filling Methods 0.000 description 132
125000004429 atom Chemical group 0.000 description 121
230000002079 cooperative effect Effects 0.000 description 104
125000002887 hydroxy group Chemical group [H]O* 0.000 description 98
125000003118 aryl group Chemical group 0.000 description 96
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 79
239000000243 solution Substances 0.000 description 73
125000004093 cyano group Chemical group *C#N 0.000 description 72
125000000623 heterocyclic group Chemical group 0.000 description 71
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 70
125000004433 nitrogen atom Chemical group N* 0.000 description 59
125000001072 heteroaryl group Chemical group 0.000 description 56
125000000304 alkynyl group Chemical group 0.000 description 55
125000000753 cycloalkyl group Chemical group 0.000 description 55
125000006850 spacer group Chemical group 0.000 description 54
239000002253 acid Substances 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
125000003342 alkenyl group Chemical group 0.000 description 48
125000004414 alkyl thio group Chemical group 0.000 description 44
125000002768 hydroxyalkyl group Chemical group 0.000 description 42
125000005843 halogen group Chemical group 0.000 description 41
125000004183 alkoxy alkyl group Chemical group 0.000 description 40
125000003710 aryl alkyl group Chemical group 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
125000000392 cycloalkenyl group Chemical group 0.000 description 39
235000002639 sodium chloride Nutrition 0.000 description 38
229910052760 oxygen Inorganic materials 0.000 description 34
239000001301 oxygen Substances 0.000 description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 31
125000004432 carbon atom Chemical group C* 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
125000004390 alkyl sulfonyl group Chemical group 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
125000004103 aminoalkyl group Chemical group 0.000 description 24
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 24
125000000468 ketone group Chemical group 0.000 description 23
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 22
125000002947 alkylene group Chemical group 0.000 description 21
125000001153 fluoro group Chemical group F* 0.000 description 21
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 21
150000003254 radicals Chemical class 0.000 description 21
239000007787 solid Substances 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
125000005326 heteroaryloxy alkyl group Chemical group 0.000 description 19
125000004104 aryloxy group Chemical group 0.000 description 18
150000001721 carbon Chemical group 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
125000005160 aryl oxy alkyl group Chemical group 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
125000004663 dialkyl amino group Chemical group 0.000 description 17
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 17
125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 17
125000003396 thiol group Chemical class [H]S* 0.000 description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
125000000000 cycloalkoxy group Chemical group 0.000 description 16
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
230000002829 reductive effect Effects 0.000 description 16
101150041968 CDC13 gene Proteins 0.000 description 15
125000003302 alkenyloxy group Chemical group 0.000 description 15
125000005422 alkyl sulfonamido group Chemical group 0.000 description 15
125000005110 aryl thio group Chemical group 0.000 description 15
125000001246 bromo group Chemical group Br* 0.000 description 15
125000001309 chloro group Chemical group Cl* 0.000 description 15
239000003921 oil Substances 0.000 description 15
235000019198 oils Nutrition 0.000 description 15
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 15
125000000033 alkoxyamino group Chemical group 0.000 description 14
125000004644 alkyl sulfinyl group Chemical group 0.000 description 14
125000004181 carboxyalkyl group Chemical group 0.000 description 14
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 14
239000007789 gas Substances 0.000 description 14
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 14
125000004043 oxo group Chemical group O=* 0.000 description 14
238000003756 stirring Methods 0.000 description 14
108010073385 Fibrin Proteins 0.000 description 13
102000009123 Fibrin Human genes 0.000 description 13
BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 13
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical group NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 13
125000005262 alkoxyamine group Chemical group 0.000 description 13
229950003499 fibrin Drugs 0.000 description 13
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 13
125000004446 heteroarylalkyl group Chemical group 0.000 description 13
125000001041 indolyl group Chemical group 0.000 description 13
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 13
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 13
238000006467 substitution reaction Methods 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
229930194542 Keto Natural products 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 12
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 12
125000006350 alkyl thio alkyl group Chemical group 0.000 description 12
125000005164 aryl thioalkyl group Chemical group 0.000 description 12
125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 12
125000001188 haloalkyl group Chemical group 0.000 description 12
125000005553 heteroaryloxy group Chemical group 0.000 description 12
125000005842 heteroatom Chemical group 0.000 description 12
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 12
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 11
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 11
125000003368 amide group Chemical group 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 11
125000001769 aryl amino group Chemical group 0.000 description 11
125000005241 heteroarylamino group Chemical group 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
230000036961 partial effect Effects 0.000 description 11
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical group COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 10
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 10
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 10
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
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239000004480 active ingredient Substances 0.000 description 10
125000001691 aryl alkyl amino group Chemical group 0.000 description 10
239000003814 drug Substances 0.000 description 10
125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
208000006011 Stroke Diseases 0.000 description 9
SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
125000004465 cycloalkenyloxy group Chemical group 0.000 description 9
125000005149 cycloalkylsulfinyl group Chemical group 0.000 description 9
125000005143 heteroarylsulfonyl group Chemical group 0.000 description 9
125000004149 thio group Chemical group *S* 0.000 description 9
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 8
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
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210000004204 blood vessel Anatomy 0.000 description 8
239000012267 brine Substances 0.000 description 8
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 8
125000002757 morpholinyl group Chemical group 0.000 description 8
125000004430 oxygen atom Chemical group O* 0.000 description 8
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 7
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 7
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 7
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
230000002776 aggregation Effects 0.000 description 7
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 7
125000005140 aralkylsulfonyl group Chemical group 0.000 description 7
125000004391 aryl sulfonyl group Chemical group 0.000 description 7
239000012298 atmosphere Substances 0.000 description 7
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000011097 chromatography purification Methods 0.000 description 7
239000012043 crude product Substances 0.000 description 7
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 7
238000009472 formulation Methods 0.000 description 7
125000004995 haloalkylthio group Chemical group 0.000 description 7
125000005150 heteroarylsulfinyl group Chemical group 0.000 description 7
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
238000009434 installation Methods 0.000 description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 7
238000010992 reflux Methods 0.000 description 7
230000004044 response Effects 0.000 description 7
239000000126 substance Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
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229910052711 selenium Inorganic materials 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229920005573 silicon-containing polymer Polymers 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
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239000000661 sodium alginate Substances 0.000 description 1
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235000019333 sodium laurylsulphate Nutrition 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
229960005202 streptokinase Drugs 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000004426 substituted alkynyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
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229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
125000004354 sulfur functional group Chemical group 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
TVVPMLFGPYQGTG-UHFFFAOYSA-M tetramethylphosphanium;iodide Chemical compound [I-].C[P+](C)(C)C TVVPMLFGPYQGTG-UHFFFAOYSA-M 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
229940124591 thiazide-type diuretic Drugs 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
125000002480 thymidyl group Chemical group 0.000 description 1
PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
229960005001 ticlopidine Drugs 0.000 description 1
229960000187 tissue plasminogen activator Drugs 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
PYHOFAHZHOBVGV-UHFFFAOYSA-N triazane Chemical compound NNN PYHOFAHZHOBVGV-UHFFFAOYSA-N 0.000 description 1
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
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 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
229920001221 xylan Polymers 0.000 description 1
150000004823 xylans Chemical class 0.000 description 1
125000002256 xylenyl group Chemical group C1(C(C=CC=C1)C)(C)* 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- 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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Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pyridine Compounds (AREA)

TW089109595A 1999-05-19 2000-07-25 Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade TWI222445B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US13479499P	1999-05-19	1999-05-19

Publications (1)

Publication Number	Publication Date
TWI222445B true TWI222445B (en)	2004-10-21

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ID=22465042

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Application Number	Title	Priority Date	Filing Date
TW089109595A TWI222445B (en)	1999-05-19	2000-07-25	Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade

Country Status (22)

Country	Link
EP (1)	EP1178970A1 (es)
JP (1)	JP2002544262A (es)
KR (1)	KR20010114271A (es)
CN (1)	CN1157380C (es)
AR (1)	AR030021A1 (es)
AU (2)	AU771718B2 (es)
BR (1)	BR0010758A (es)
CA (1)	CA2373614A1 (es)
CZ (1)	CZ20014116A3 (es)
EA (1)	EA004867B1 (es)
HU (1)	HUP0201242A3 (es)
IL (1)	IL146243A0 (es)
MX (1)	MXPA01011804A (es)
NO (1)	NO20015604L (es)
NZ (1)	NZ514874A (es)
PE (1)	PE20010229A1 (es)
PL (1)	PL352827A1 (es)
SK (1)	SK15852001A3 (es)
TW (1)	TWI222445B (es)
UY (1)	UY26156A1 (es)
WO (1)	WO2000069832A1 (es)
ZA (2)	ZA200109339B (es)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6750342B1 (en)	1999-05-19	2004-06-15	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
US6716838B1 (en)	1999-05-19	2004-04-06	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl uracils as anticoagulative agents
US6653316B1 (en)	1999-05-19	2003-11-25	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
KR20010113969A (ko) *	1999-05-19	2001-12-28	추후보정	항응고제로서의 치환된 폴리시클릭 아릴 및 헤테로아릴우라실
US7015230B1 (en)	1999-05-19	2006-03-21	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl uracils useful for selective inhibition of the coagulation cascade
US6664255B1 (en)	1999-05-19	2003-12-16	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyrazinones useful for selective inhibition of the coagulation cascade
US6458952B1 (en)	1999-05-19	2002-10-01	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl uracils useful for selective inhibition of the coagulation cascade
US6867217B1 (en)	1999-05-19	2005-03-15	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyridones useful for selective inhibition of the coagulation cascade
US6852761B2 (en)	2000-03-13	2005-02-08	Pharmacia Corporation	Polycyclic aryl and heteroaryl substituted benzenes useful for selective inhibition of the coagulation cascade
CA2405561A1 (en)	2000-04-05	2001-10-18	Pharmacia Corporation	Polycyclic aryl and heteroaryl substituted 4-pyrones useful for selective inhibition of the coagulation cascade
EP1268428A2 (en)	2000-04-05	2003-01-02	Pharmacia Corporation	Polycyclic aryl and heteroaryl substituted 4-pyridones useful for selective inhibition of the coagulation cascade
US6686484B2 (en)	2000-04-17	2004-02-03	Pharmacia Corporation	Polycyclic aryl and heteroaryl substituted 1,4-quinones useful for selective inhibition of the coagulation cascade
WO2001087851A1 (en) *	2000-05-18	2001-11-22	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
US6710058B2 (en)	2000-11-06	2004-03-23	Bristol-Myers Squibb Pharma Company	Monocyclic or bicyclic carbocycles and heterocycles as factor Xa inhibitors
US7015223B1 (en)	2000-11-20	2006-03-21	Pharmacia Corporation	Substituted polycyclic aryl and heteroaryl 1,2,4-triazinones useful for selective inhibition of the coagulation cascade
US7119094B1 (en)	2000-11-20	2006-10-10	Warner-Lambert Company	Substituted polycyclic aryl and heteroarpyl pyrazinones useful for selective inhibition of the coagulation cascade
MXPA03004458A (es)	2000-11-20	2005-01-25	Pharmacia Corp	Arilpiridinas y heteroarilpiridinas sustituidas utiles para inhibicion selectiva de la cascada de coagulacion.
WO2003029216A1 (en)	2001-10-03	2003-04-10	Pharmacia Corporation	6-membered heterocyclic compounds useful for selective inhibition of the coagulation cascade
WO2003029224A1 (en) *	2001-10-03	2003-04-10	Pharmacia Corporation	6-membered unsaturated heterocyclic compounds useful for selective inhibition of the coagulation cascade
AU2002367752A1 (en)	2001-10-03	2003-11-17	Pharmacia Corporation	Substituted 5-membered polycyclic compounds useful for selective inhibition of the coagulation cascade
JP2005532268A (ja)	2002-02-22	2005-10-27	ファルマシア・アンド・アップジョン・カンパニー・エルエルシー	置換されたピリミジノンおよびピリミジンチオン
TW200307667A (en)	2002-05-06	2003-12-16	Bristol Myers Squibb Co	Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors
US7217794B2 (en)	2003-04-02	2007-05-15	Daiamed, Inc.	Compounds and methods for treatment of thrombosis
US7182738B2 (en)	2003-04-23	2007-02-27	Marctec, Llc	Patient monitoring apparatus and method for orthosis and other devices
CA2610400A1 (en) *	2005-06-07	2006-12-14	Pharmacopeia, Inc.	Azinone and diazinone v3 inhibitors for depression and stress disorders
CN104311537B (zh) *	2014-09-19	2016-08-24	广东东阳光药业有限公司	含有嘧啶酮乙酰基取代基吡唑类化合物及其组合物及用途
AU2020396565C1 (en) *	2019-12-04	2025-05-15	Omeros Corporation	MASP-2 inhibitors and methods of use
CN115779953B (zh) *	2022-12-19	2024-06-21	中南大学	铜负载碳基单原子材料及其制备方法和应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5441960A (en) *	1992-04-16	1995-08-15	Zeneca Limited	1-pyrimidinylacetamide human leukocyte elastate inhibitors
US5948785A (en) *	1995-04-27	1999-09-07	The Green Cross Corporation	Heterocyclic amide compounds and pharmaceutical use of the same

2000
- 2000-05-17 JP JP2000618249A patent/JP2002544262A/ja active Pending
- 2000-05-17 CN CNB008077479A patent/CN1157380C/zh not_active Expired - Fee Related
- 2000-05-17 WO PCT/US2000/009806 patent/WO2000069832A1/en not_active Ceased
- 2000-05-17 CA CA002373614A patent/CA2373614A1/en not_active Abandoned
- 2000-05-17 PL PL00352827A patent/PL352827A1/xx not_active Application Discontinuation
- 2000-05-17 AU AU49734/00A patent/AU771718B2/en not_active Ceased
- 2000-05-17 KR KR1020017014753A patent/KR20010114271A/ko not_active Withdrawn
- 2000-05-17 BR BR0010758-1A patent/BR0010758A/pt not_active IP Right Cessation
- 2000-05-17 NZ NZ514874A patent/NZ514874A/en unknown
- 2000-05-17 IL IL14624300A patent/IL146243A0/xx unknown
- 2000-05-17 EP EP00931928A patent/EP1178970A1/en not_active Withdrawn
- 2000-05-17 EA EA200101214A patent/EA004867B1/ru not_active IP Right Cessation
- 2000-05-17 SK SK1585-2001A patent/SK15852001A3/sk unknown
- 2000-05-17 HU HU0201242A patent/HUP0201242A3/hu unknown
- 2000-05-17 CZ CZ20014116A patent/CZ20014116A3/cs unknown
- 2000-05-17 MX MXPA01011804A patent/MXPA01011804A/es unknown
- 2000-05-19 AR ARP000102446A patent/AR030021A1/es unknown
- 2000-05-19 UY UY26156A patent/UY26156A1/es not_active Application Discontinuation
- 2000-06-09 PE PE2000000575A patent/PE20010229A1/es not_active Application Discontinuation
- 2000-07-25 TW TW089109595A patent/TWI222445B/zh not_active IP Right Cessation
2001
- 2001-11-13 ZA ZA200109339A patent/ZA200109339B/xx unknown
- 2001-11-16 NO NO20015604A patent/NO20015604L/no not_active Application Discontinuation
2004
- 2004-01-21 ZA ZA200400448A patent/ZA200400448B/xx unknown
- 2004-05-31 AU AU2004202375A patent/AU2004202375A1/en not_active Abandoned

Also Published As

Publication number	Publication date
AU771718B2 (en)	2004-04-01
AR030021A1 (es)	2003-08-13
UY26156A1 (es)	2000-12-29
BR0010758A (pt)	2003-06-10
HUP0201242A2 (hu)	2002-12-28
EA200101214A1 (ru)	2002-06-27
KR20010114271A (ko)	2001-12-31
NZ514874A (en)	2004-11-26
AU2004202375A1 (en)	2004-06-24
AU4973400A (en)	2000-12-05
ZA200400448B (en)	2004-09-29
EP1178970A1 (en)	2002-02-13
EA004867B1 (ru)	2004-08-26
SK15852001A3 (sk)	2003-06-03
HUP0201242A3 (en)	2003-02-28
WO2000069832A1 (en)	2000-11-23
PL352827A1 (en)	2003-09-08
NO20015604L (no)	2002-01-11
IL146243A0 (en)	2002-07-25
ZA200109339B (en)	2004-05-26
PE20010229A1 (es)	2001-03-07
CN1351593A (zh)	2002-05-29
NO20015604D0 (no)	2001-11-16
CZ20014116A3 (cs)	2002-06-12
CN1157380C (zh)	2004-07-14
CA2373614A1 (en)	2000-11-23
JP2002544262A (ja)	2002-12-24
MXPA01011804A (es)	2003-09-04

Publication	Publication Date	Title
TWI222445B (en)	2004-10-21	Substituted polycyclic aryl and heteroaryl pyrimidinones useful for selective inhibition of the coagulation cascade
AU771740B2 (en)	2004-04-01	Substituted polycyclic aryl and heteroaryl uracils as anticoagulative agents
CA2430037A1 (en)	2002-05-30	Substituted polycyclic aryl and heteroaryl pyridines useful for selective inhibition of the coagulation cascade
SK15862001A3 (sk)	2002-08-06	Substituované polycyklické aryl a heteroaryl pyridóny užitočné na selektívnu inhibíciu koagulačnej kaskády
EP1202975B1 (en)	2005-04-06	Substituted polycyclic aryl and heteroaryl pyrazinones useful for selective inhibition of the coagulation cascade
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