MX2010012635A - Compuestos heterociclicos como inhibidores de factor ixa. - Google Patents
Compuestos heterociclicos como inhibidores de factor ixa.Info
- Publication number
- MX2010012635A MX2010012635A MX2010012635A MX2010012635A MX2010012635A MX 2010012635 A MX2010012635 A MX 2010012635A MX 2010012635 A MX2010012635 A MX 2010012635A MX 2010012635 A MX2010012635 A MX 2010012635A MX 2010012635 A MX2010012635 A MX 2010012635A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- aryl
- group
- compound according
- further characterized
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 5
- 229940123849 Factor IXa inhibitor Drugs 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 332
- 150000003839 salts Chemical class 0.000 claims abstract description 126
- 239000012453 solvate Substances 0.000 claims abstract description 47
- 150000002148 esters Chemical class 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- -1 heterocyclenyl Chemical group 0.000 claims description 240
- 125000003118 aryl group Chemical group 0.000 claims description 186
- 125000000217 alkyl group Chemical group 0.000 claims description 173
- 125000001072 heteroaryl group Chemical group 0.000 claims description 148
- 125000000623 heterocyclic group Chemical group 0.000 claims description 124
- 125000004432 carbon atom Chemical group C* 0.000 claims description 116
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 109
- 125000001424 substituent group Chemical group 0.000 claims description 106
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 125000001188 haloalkyl group Chemical group 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 27
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 108010048049 Factor IXa Proteins 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000006413 ring segment Chemical group 0.000 claims description 25
- 208000035475 disorder Diseases 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 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 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 7
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 5
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 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 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 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 2
- PQUGCKBLVKJMNT-UHFFFAOYSA-N SC560 Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 PQUGCKBLVKJMNT-UHFFFAOYSA-N 0.000 claims 1
- 125000003943 azolyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 85
- 229940002612 prodrug Drugs 0.000 abstract description 23
- 239000000651 prodrug Substances 0.000 abstract description 23
- 230000009424 thromboembolic effect Effects 0.000 abstract description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 245
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 151
- 239000000203 mixture Substances 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 113
- 235000019439 ethyl acetate Nutrition 0.000 description 96
- 239000000243 solution Substances 0.000 description 87
- 230000002829 reductive effect Effects 0.000 description 73
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- 229910001868 water Inorganic materials 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 235000002639 sodium chloride Nutrition 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 58
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
- 239000011541 reaction mixture Substances 0.000 description 53
- 239000003112 inhibitor Substances 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
- 239000002904 solvent Substances 0.000 description 42
- 239000012044 organic layer Substances 0.000 description 37
- 239000012043 crude product Substances 0.000 description 35
- 239000012267 brine Substances 0.000 description 32
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- 235000019341 magnesium sulphate Nutrition 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 108090000190 Thrombin Proteins 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 23
- 229960004072 thrombin Drugs 0.000 description 23
- 238000012360 testing method Methods 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 20
- 238000010898 silica gel chromatography Methods 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 208000007536 Thrombosis Diseases 0.000 description 19
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
- 230000004913 activation Effects 0.000 description 18
- 238000004007 reversed phase HPLC Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 16
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 229940124597 therapeutic agent Drugs 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 125000004122 cyclic group Chemical group 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- 239000007821 HATU Substances 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 239000003146 anticoagulant agent Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 108010074860 Factor Xa Proteins 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
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- 229960000583 acetic acid Drugs 0.000 description 11
- 125000003710 aryl alkyl group Chemical group 0.000 description 11
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- 102000002262 Thromboplastin Human genes 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 229940127219 anticoagulant drug Drugs 0.000 description 9
- 229910015845 BBr3 Inorganic materials 0.000 description 8
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 8
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 230000017531 blood circulation Effects 0.000 description 8
- 239000003114 blood coagulation factor Substances 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
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- 239000000706 filtrate Substances 0.000 description 8
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- 229960000187 tissue plasminogen activator Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
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- LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
-
- 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
- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5431008P | 2008-05-19 | 2008-05-19 | |
| PCT/US2009/044291 WO2009143039A2 (en) | 2008-05-19 | 2009-05-18 | Heterocyclic compounds as factor ixa inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2010012635A true MX2010012635A (es) | 2010-12-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010012635A MX2010012635A (es) | 2008-05-19 | 2009-05-18 | Compuestos heterociclicos como inhibidores de factor ixa. |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8148363B2 (https=) |
| EP (2) | EP2300435A2 (https=) |
| JP (1) | JP5504259B2 (https=) |
| CN (1) | CN102099340A (https=) |
| AR (1) | AR071823A1 (https=) |
| CA (1) | CA2724430A1 (https=) |
| CL (1) | CL2009001214A1 (https=) |
| MX (1) | MX2010012635A (https=) |
| PE (1) | PE20091972A1 (https=) |
| TW (1) | TW201008930A (https=) |
| WO (1) | WO2009143039A2 (https=) |
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| WO2010149755A1 (en) * | 2009-06-26 | 2010-12-29 | Novartis Ag | 1, 3-disubstituted imidazolidin-2-one derivatives as inhibitors of cyp 17 |
| US8242284B1 (en) * | 2009-09-21 | 2012-08-14 | The United States Of America As Represented By The United States Department Of Energy | Anti-cancer agents based on 6-trifluoromethoxybenzimidazole derivatives and method of making |
| CN102918034B (zh) | 2010-03-30 | 2015-06-03 | 维颂公司 | 多取代芳族化合物作为凝血酶的抑制剂 |
| CA2803695A1 (en) | 2010-06-28 | 2012-01-05 | Bayer Intellectual Property Gmbh | Heteroaryl-substituted pyridine compounds for use as pesticides |
| EP2588465B1 (en) | 2010-06-30 | 2017-01-25 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| CN107266433A (zh) | 2010-11-09 | 2017-10-20 | 铁木医药有限公司 | sGC刺激剂 |
| US9029399B2 (en) | 2011-04-28 | 2015-05-12 | Novartis Ag | 17α-hydroxylase/C17,20-lyase inhibitors |
| US9161924B2 (en) | 2011-07-08 | 2015-10-20 | Merck Sharp & Dohme Corp. | Factor IXa inhibitors |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| CN106117194A (zh) | 2011-12-27 | 2016-11-16 | 铁木医药有限公司 | 可用作sgc刺激剂的2‑苄基、3‑(嘧啶‑2‑基)取代的吡唑类 |
| CN102660253B (zh) * | 2012-03-07 | 2014-05-21 | 泰山医学院 | 一种吡唑啉衍生物类Ni2+荧光探针及其应用 |
| WO2014120346A1 (en) * | 2012-12-19 | 2014-08-07 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| WO2014099695A1 (en) * | 2012-12-19 | 2014-06-26 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| US9695198B2 (en) | 2012-12-19 | 2017-07-04 | Merck Sharp & Dohme Corp. | Factor IXa inhibitors |
| ES2791749T3 (es) | 2013-03-15 | 2020-11-05 | Verseon Corp | Halogenopirazoles como inhibidores de la trombina |
| LT2968297T (lt) | 2013-03-15 | 2019-01-10 | Verseon Corporation | Multipakeistieji aromatiniai junginiai kaip serino proteazės inhibitoriai |
| WO2015160636A1 (en) | 2014-04-16 | 2015-10-22 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| BR112017004612A2 (pt) * | 2014-09-10 | 2018-01-30 | Epizyme, Inc. | compostos, composição farmacêutica, usos de um composto, e kit |
| WO2016044645A1 (en) * | 2014-09-17 | 2016-03-24 | Elmaleh David R | Anticoagulant derivatives for cardiovascular imaging |
| CN106687445A (zh) | 2014-09-17 | 2017-05-17 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的吡唑基取代的吡啶酮化合物 |
| WO2016087615A1 (en) | 2014-12-04 | 2016-06-09 | Procomcure Biotech Gmbh | Novel imidazole-based heterocyclic compounds |
| LT3226858T (lt) | 2014-12-04 | 2021-06-10 | Procomcure Biotech Gmbh | Imidazolo pagrindo antimikrobiniai agentai |
| WO2016133793A1 (en) * | 2015-02-16 | 2016-08-25 | Merck Sharp & Dohme Corp. | FACTOR IXa INHIBITORS |
| RU2017131562A (ru) | 2015-02-27 | 2019-03-27 | Версеон Корпорейшн | Замещенные пиразольные соединения как ингибиторы сериновых протеаз |
| JP2019510802A (ja) * | 2016-04-07 | 2019-04-18 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | タンパク質調節物質として有用な複素環アミド |
| PT3440076T (pt) * | 2016-04-07 | 2022-07-29 | Glaxosmithkline Ip Dev Ltd | Amidas heterocíclicas úteis como modeladores de proteína |
| WO2018093716A1 (en) * | 2016-11-18 | 2018-05-24 | Merck Sharp & Dohme Corp. | FACTOR XIIa INHIBITORS |
| US11040947B2 (en) | 2017-03-22 | 2021-06-22 | The Research Foundation For The State University Of New York | Substituted quinazolines as matrix metalloproteinase-9 hemopexin domain inhibitors |
| HUE062236T2 (hu) * | 2018-04-17 | 2023-10-28 | Univ Michigan Regents | Vérlemezke funkció inhibitorok és eljárás azok alkalmazására |
| CN112457308B (zh) * | 2019-09-09 | 2024-01-02 | 上海长森药业有限公司 | 新型三环芳香杂环化合物，及其制备方法、药物组合物和应用 |
| TW202206429A (zh) | 2020-04-29 | 2022-02-16 | 美商迦舒布魯姆生物有限公司 | 雜環ｇｌｐ—１促效劑 |
| JP2023537501A (ja) | 2020-08-06 | 2023-09-01 | ガシャーブラム・バイオ・インコーポレイテッド | ヘテロ環ｇｌｐ－１アゴニスト |
| WO2022081573A1 (en) * | 2020-10-12 | 2022-04-21 | University Of Tennessee Research Foundation | Transient receptor potential canonical 3 inhibitors and methods of use thereof |
| EP4229050A4 (en) * | 2020-10-13 | 2024-12-11 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| CN114149371B (zh) * | 2021-11-26 | 2023-08-22 | 首都医科大学 | 四取代吡唑类化合物及其应用 |
| CN114478511B (zh) * | 2022-02-24 | 2023-06-20 | 中国药科大学 | 苯并恶唑类化合物及其制备方法、药物组合物和应用 |
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| EP0028489B1 (en) | 1979-11-05 | 1983-10-05 | Beecham Group Plc | Enzyme derivatives, and their preparation |
| IL106197A (en) | 1992-07-30 | 1999-11-30 | Cor Therapeutics Inc | Agagonists for the rhombin receptors and pharmaceutical preparations containing them |
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| TW536540B (en) | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| US6063847A (en) | 1997-11-25 | 2000-05-16 | Schering Corporation | Thrombin receptor antagonists |
| HUP0104634A3 (en) | 1998-07-06 | 2002-11-28 | Bristol Myers Squibb Co | Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists |
| MY125533A (en) | 1999-12-06 | 2006-08-30 | Bristol Myers Squibb Co | Heterocyclic dihydropyrimidine compounds |
| US7235567B2 (en) | 2000-06-15 | 2007-06-26 | Schering Corporation | Crystalline polymorph of a bisulfate salt of a thrombin receptor antagonist |
| US7304078B2 (en) | 2002-04-16 | 2007-12-04 | Schering Corporation | Thrombin receptor antagonists |
| ES2291323T3 (es) | 2000-06-15 | 2008-03-01 | Schering Corporation | Antagonistas de receptores de trombina. |
| BR0213967A (pt) | 2001-10-18 | 2005-08-30 | Schering Corp | Análogos de himbacina como antagonistas do receptor de trombina |
| BR0213562A (pt) * | 2001-10-26 | 2004-08-31 | Aventis Pharma Inc | Benzimidazóis e análogos e seu uso como inibidores de cinases de proteìna |
| EP1667983A4 (en) * | 2003-09-23 | 2010-07-21 | Merck Sharp & Dohme | PYRAZOL MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS |
| CN1980665A (zh) * | 2004-07-07 | 2007-06-13 | 默克公司 | 吡唑酰胺衍生物，包含这些化合物的组合物和使用方法 |
| WO2006014618A2 (en) * | 2004-07-22 | 2006-02-09 | Merck & Co., Inc. | Substituted pyrazoles, compositions containing such compounds and methods of use |
| EP1797072A4 (en) * | 2004-09-17 | 2009-09-09 | Exelixis Inc | PYRAZOLKINASE MODULATORS AND USE METHOD |
| EP1948614A2 (en) * | 2005-11-18 | 2008-07-30 | Takeda San Diego, Inc. | Glucokinase activators |
| US7968683B1 (en) * | 2008-05-07 | 2011-06-28 | Schering Corporation | Factor IXa crystals, related complexes and methods |
| WO2009140342A1 (en) * | 2008-05-16 | 2009-11-19 | Schering Corporation | Glucagon receptor antagonists, compositions, and methods for their use |
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- 2009-05-18 EP EP09751268A patent/EP2300435A2/en not_active Ceased
- 2009-05-18 MX MX2010012635A patent/MX2010012635A/es active IP Right Grant
- 2009-05-18 WO PCT/US2009/044291 patent/WO2009143039A2/en not_active Ceased
- 2009-05-18 CA CA2724430A patent/CA2724430A1/en not_active Abandoned
- 2009-05-18 TW TW098116429A patent/TW201008930A/zh unknown
- 2009-05-18 JP JP2011510610A patent/JP5504259B2/ja not_active Expired - Fee Related
- 2009-05-18 CN CN200980128238XA patent/CN102099340A/zh active Pending
- 2009-05-18 EP EP14173412.9A patent/EP2805939B1/en not_active Not-in-force
- 2009-05-18 PE PE2009000694A patent/PE20091972A1/es not_active Application Discontinuation
- 2009-05-18 US US12/993,607 patent/US8148363B2/en active Active
- 2009-05-18 AR ARP090101778A patent/AR071823A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2724430A1 (en) | 2009-11-26 |
| EP2805939B1 (en) | 2018-06-27 |
| JP5504259B2 (ja) | 2014-05-28 |
| JP2011520967A (ja) | 2011-07-21 |
| TW201008930A (en) | 2010-03-01 |
| PE20091972A1 (es) | 2010-01-15 |
| US8148363B2 (en) | 2012-04-03 |
| EP2805939A1 (en) | 2014-11-26 |
| WO2009143039A3 (en) | 2010-07-08 |
| AR071823A1 (es) | 2010-07-14 |
| US20110065682A1 (en) | 2011-03-17 |
| CL2009001214A1 (es) | 2010-12-31 |
| EP2300435A2 (en) | 2011-03-30 |
| WO2009143039A2 (en) | 2009-11-26 |
| CN102099340A (zh) | 2011-06-15 |
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