NZ554211A - Substituted 2H-1,3-Benzoxazin-4(3H)-ones - Google Patents
Substituted 2H-1,3-Benzoxazin-4(3H)-onesInfo
- Publication number
- NZ554211A NZ554211A NZ554211A NZ55421105A NZ554211A NZ 554211 A NZ554211 A NZ 554211A NZ 554211 A NZ554211 A NZ 554211A NZ 55421105 A NZ55421105 A NZ 55421105A NZ 554211 A NZ554211 A NZ 554211A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- group
- pct
- alkoxy
- haloalkyl
- Prior art date
Links
- YBYIZRPBXCCDQW-UHFFFAOYSA-N 2,3-dihydro-1,3-benzoxazin-4-one Chemical class C1=CC=C2C(=O)NCOC2=C1 YBYIZRPBXCCDQW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000003814 drug Substances 0.000 claims abstract description 13
- 208000007536 Thrombosis Diseases 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- -1 cyano, hydroxy Chemical group 0.000 claims description 42
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000003146 anticoagulant agent Substances 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 10
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 230000000302 ischemic effect Effects 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 7
- 210000004369 blood Anatomy 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000005557 antagonist Substances 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 206010002388 Angina unstable Diseases 0.000 claims description 4
- 208000007718 Stable Angina Diseases 0.000 claims description 4
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 4
- 208000007814 Unstable Angina Diseases 0.000 claims description 4
- 238000002399 angioplasty Methods 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 4
- 230000000702 anti-platelet effect Effects 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 4
- 201000010875 transient cerebral ischemia Diseases 0.000 claims description 4
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 3
- 206010038563 Reocclusion Diseases 0.000 claims description 3
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 3
- 229940127219 anticoagulant drug Drugs 0.000 claims description 3
- 229960002897 heparin Drugs 0.000 claims description 3
- 229920000669 heparin Polymers 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
- 206010022562 Intermittent claudication Diseases 0.000 claims description 2
- 229940122388 Thrombin inhibitor Drugs 0.000 claims description 2
- 206010043647 Thrombotic Stroke Diseases 0.000 claims description 2
- 108090000300 Thromboxane Receptors Proteins 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 239000003529 anticholesteremic agent Substances 0.000 claims description 2
- 229940127226 anticholesterol agent Drugs 0.000 claims description 2
- 229940072645 coumadin Drugs 0.000 claims description 2
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 2
- 230000003480 fibrinolytic effect Effects 0.000 claims description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 2
- 230000002107 myocardial effect Effects 0.000 claims description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 2
- 239000002464 receptor antagonist Substances 0.000 claims description 2
- 229940044551 receptor antagonist Drugs 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 229940076279 serotonin Drugs 0.000 claims description 2
- 239000003868 thrombin inhibitor Substances 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims 1
- 102000003938 Thromboxane Receptors Human genes 0.000 claims 1
- 229960000610 enoxaparin Drugs 0.000 claims 1
- 230000007971 neurological deficit Effects 0.000 claims 1
- 230000002441 reversible effect Effects 0.000 claims 1
- 150000004893 oxazines Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 238000000034 method Methods 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 238000004007 reversed phase HPLC Methods 0.000 description 62
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 61
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 52
- 210000001772 blood platelet Anatomy 0.000 description 41
- 238000005481 NMR spectroscopy Methods 0.000 description 37
- IVKNUIVDQMARCO-UHFFFAOYSA-N oxazin-4-one Chemical compound O=C1C=CON=C1 IVKNUIVDQMARCO-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 26
- 239000004202 carbamide Substances 0.000 description 26
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 229940093499 ethyl acetate Drugs 0.000 description 24
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000010168 coupling process Methods 0.000 description 22
- 230000008878 coupling Effects 0.000 description 20
- 238000005859 coupling reaction Methods 0.000 description 20
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 18
- 239000000543 intermediate Substances 0.000 description 16
- 229940100389 Sulfonylurea Drugs 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 12
- 102100037600 P2Y purinoceptor 1 Human genes 0.000 description 12
- 229930040373 Paraformaldehyde Natural products 0.000 description 12
- 108010085249 Purinergic P2 Receptors Proteins 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- 229920002866 paraformaldehyde Polymers 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000006073 displacement reaction Methods 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YUEDYKGJCNMJDQ-UHFFFAOYSA-N sulfonylurea;urea Chemical compound NC(N)=O.NC(=O)N=S(=O)=O YUEDYKGJCNMJDQ-UHFFFAOYSA-N 0.000 description 10
- QHIIPTWSKPGKPZ-UHFFFAOYSA-N (2-carbonochloridoyl-4,5-difluorophenyl) acetate Chemical compound CC(=O)OC1=CC(F)=C(F)C=C1C(Cl)=O QHIIPTWSKPGKPZ-UHFFFAOYSA-N 0.000 description 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
- 230000027455 binding Effects 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 230000001419 dependent effect Effects 0.000 description 8
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- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- WLMZTKAZJUWXCB-KQYNXXCUSA-N [(2r,3s,4r,5r)-5-(6-amino-2-methylsulfanylpurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphono hydrogen phosphate Chemical compound C12=NC(SC)=NC(N)=C2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O WLMZTKAZJUWXCB-KQYNXXCUSA-N 0.000 description 7
- 230000002776 aggregation Effects 0.000 description 7
- 238000004220 aggregation Methods 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
- RKLQLYBJAZBSEU-UHFFFAOYSA-N 5-chlorothiophene-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)S1 RKLQLYBJAZBSEU-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000002785 anti-thrombosis Effects 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 210000004623 platelet-rich plasma Anatomy 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000001732 thrombotic effect Effects 0.000 description 6
- 241000282326 Felis catus Species 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 239000006196 drop Substances 0.000 description 4
- XALLJMFDLUYTTF-UHFFFAOYSA-N ethyl n-(5-chlorothiophen-2-yl)sulfonylcarbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(Cl)S1 XALLJMFDLUYTTF-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- 230000000144 pharmacologic effect Effects 0.000 description 4
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- 230000002829 reductive effect Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 3
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 3
- LQPQOESULBOBBB-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C=C1O LQPQOESULBOBBB-UHFFFAOYSA-N 0.000 description 3
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical class C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 3
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 3
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229960001456 adenosine triphosphate Drugs 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
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- 239000010410 layer Substances 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
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Classifications
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
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- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61456404P | 2004-09-29 | 2004-09-29 | |
| PCT/US2005/034246 WO2006039212A2 (en) | 2004-09-29 | 2005-09-26 | Substituted 2h-1,3-benzoxazin-4(3h)-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ554211A true NZ554211A (en) | 2010-10-29 |
Family
ID=36142983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ554211A NZ554211A (en) | 2004-09-29 | 2005-09-26 | Substituted 2H-1,3-Benzoxazin-4(3H)-ones |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7205296B2 (enExample) |
| EP (1) | EP1812429A4 (enExample) |
| JP (1) | JP2008514703A (enExample) |
| KR (1) | KR20070064356A (enExample) |
| CN (1) | CN101031565B (enExample) |
| AU (1) | AU2005292314B2 (enExample) |
| BR (1) | BRPI0516181A (enExample) |
| CA (1) | CA2581638A1 (enExample) |
| IL (1) | IL182180A0 (enExample) |
| MX (1) | MX2007003836A (enExample) |
| NZ (1) | NZ554211A (enExample) |
| WO (1) | WO2006039212A2 (enExample) |
| ZA (1) | ZA200702688B (enExample) |
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| WO2013177224A1 (en) * | 2012-05-22 | 2013-11-28 | Genentech, Inc. | N-substituted benzamides and their use in the treatment of pain |
| BR112015000187A2 (pt) | 2012-07-06 | 2017-06-27 | Genentech Inc | benzamidas substituídas com n e métodos de uso das mesmas |
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| BR112015022488A2 (pt) | 2013-03-14 | 2017-07-18 | Genentech Inc | triazolopiridinas substituídas e métodos de uso das mesmas |
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| KR102523430B1 (ko) | 2014-08-04 | 2023-04-19 | 누에볼루션 에이/에스 | 염증성, 대사성, 종양성 및 자가면역성 질환의 치료에 유용한 피리미딘의 임의적 융합 헤테로시클릴-치환 유도체 |
| RS60906B1 (sr) | 2014-10-06 | 2020-11-30 | Vertex Pharma | Modulatori regulatora transmembranske provodljivosti za cističnu fibrozu |
| PT3578547T (pt) | 2015-02-16 | 2021-06-22 | The Provost Fellows Found Scholars And Other Members Of Board Of College Of Holy And Undivided Trini | Sulfonilureias e compostos relacionados e uso dos mesmos |
| CR20170591A (es) | 2015-05-22 | 2018-05-07 | Genentech Inc | Benzamidas sustituidas y métodos para utilizarlas |
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| EP3436432B1 (en) | 2016-03-30 | 2021-01-27 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
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| PT3661925T (pt) | 2017-07-07 | 2022-01-31 | Inflazome Ltd | Novos compostos de sulfonamida-carboxamida |
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| AU2018347307A1 (en) | 2017-10-09 | 2020-04-23 | Nuvation Bio Inc. | Heterocyclic compounds and uses thereof |
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| AU2018351533B2 (en) | 2017-10-19 | 2023-02-02 | Vertex Pharmaceuticals Incorporated | Crystalline forms and compositions of CFTR modulators |
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| JP7245834B2 (ja) | 2017-12-08 | 2023-03-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | 嚢胞性線維症膜コンダクタンス制御因子のモジュレーターを作成するためのプロセス |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| WO2019165290A1 (en) | 2018-02-26 | 2019-08-29 | Genentech, Inc. | Pyridine-sulfonamide compounds and their use against pain and related conditions |
| EP3759077A1 (en) | 2018-03-02 | 2021-01-06 | Inflazome Limited | Novel compounds |
| CN111936494A (zh) | 2018-03-30 | 2020-11-13 | 豪夫迈·罗氏有限公司 | 作为钠通道抑制剂的取代的氢-吡啶并-吖嗪 |
| US11414439B2 (en) | 2018-04-13 | 2022-08-16 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| CN113939296A (zh) | 2019-04-09 | 2022-01-14 | 诺维逊生物股份有限公司 | 杂环化合物及其用途 |
| EP3952879A4 (en) * | 2019-04-09 | 2023-01-04 | Nuvation Bio Inc. | HETEROCYCLIC COMPOUNDS AND THEIR USES |
| US20220168313A1 (en) * | 2019-04-09 | 2022-06-02 | Nuvation Bio Inc. | Heterocyclic compounds and uses thereof |
| JP7450980B2 (ja) * | 2019-12-10 | 2024-03-18 | シャンハイ ジムン バイオファーマ，インコーポレーテッド | 神経保護効果を有する化合物およびその調製方法と用途 |
| US11447479B2 (en) | 2019-12-20 | 2022-09-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| UY38994A (es) | 2019-12-20 | 2021-07-30 | Nuevolution As | Compuestos activos frente a receptores nucleares |
| AU2021245397A1 (en) | 2020-03-31 | 2022-10-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
| EP4126875A1 (en) | 2020-03-31 | 2023-02-08 | Nuevolution A/S | Compounds active towards nuclear receptors |
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| FI101150B (fi) | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
| FR2702477B1 (fr) * | 1993-03-08 | 1995-04-28 | Synthelabo | Dérivés de benzoxazine, leur préparation et leur application en thérapeutique. |
| JP3814742B2 (ja) * | 1996-10-18 | 2006-08-30 | イハラケミカル工業株式会社 | ４−フルオロサリチル酸類 |
| SE9702774D0 (sv) | 1997-07-22 | 1997-07-22 | Astra Pharma Prod | Novel compounds |
| JP2002509152A (ja) | 1998-01-15 | 2002-03-26 | シーオーアール セラピューティクス インコーポレイテッド | 血小板ａｄｐ受容体阻害剤 |
| CA2332608C (en) | 1998-06-17 | 2010-03-23 | Bristol-Myers Squibb Company | Preventing cerebral infarction through administration of adp-receptor antiplatelet and antihypertensive drugs in combination |
| US6509348B1 (en) | 1998-11-03 | 2003-01-21 | Bristol-Myers Squibb Company | Combination of an ADP-receptor blocking antiplatelet drug and a thromboxane A2 receptor antagonist and a method for inhibiting thrombus formation employing such combination |
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| ATE309999T1 (de) | 2000-02-04 | 2005-12-15 | Portola Pharm Inc | Blutplättchen-adp-rezeptor-inhibitoren |
| ATE357457T1 (de) | 2000-11-01 | 2007-04-15 | Astellas Pharma Inc | Verfahren zum screenen eines plättchenhemmers |
| US6861424B2 (en) | 2001-06-06 | 2005-03-01 | Schering Aktiengesellschaft | Platelet adenosine diphosphate receptor antagonists |
| JPWO2004052871A1 (ja) * | 2002-12-06 | 2006-04-13 | 東レ株式会社 | ベンゾモルホリン誘導体 |
| CN1863789B (zh) * | 2003-10-03 | 2010-06-09 | 博尔托拉制药公司 | 取代的异喹啉酮 |
| DE602004024093D1 (de) * | 2003-10-03 | 2009-12-24 | Portola Pharm Inc | 2,4-dioxo-3-chinazolinylarylsulfonylharnstoffe |
-
2005
- 2005-09-26 EP EP05798632A patent/EP1812429A4/en not_active Withdrawn
- 2005-09-26 BR BRPI0516181-9A patent/BRPI0516181A/pt not_active IP Right Cessation
- 2005-09-26 AU AU2005292314A patent/AU2005292314B2/en not_active Ceased
- 2005-09-26 MX MX2007003836A patent/MX2007003836A/es active IP Right Grant
- 2005-09-26 CN CN2005800328848A patent/CN101031565B/zh not_active Expired - Fee Related
- 2005-09-26 NZ NZ554211A patent/NZ554211A/en not_active IP Right Cessation
- 2005-09-26 KR KR1020077009902A patent/KR20070064356A/ko not_active Ceased
- 2005-09-26 US US11/236,051 patent/US7205296B2/en not_active Expired - Lifetime
- 2005-09-26 JP JP2007534673A patent/JP2008514703A/ja not_active Ceased
- 2005-09-26 WO PCT/US2005/034246 patent/WO2006039212A2/en not_active Ceased
- 2005-09-26 ZA ZA200702688A patent/ZA200702688B/en unknown
- 2005-09-26 CA CA002581638A patent/CA2581638A1/en not_active Abandoned
-
2007
- 2007-03-26 IL IL182180A patent/IL182180A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007003836A (es) | 2007-08-20 |
| BRPI0516181A (pt) | 2008-08-26 |
| ZA200702688B (en) | 2008-06-25 |
| WO2006039212A3 (en) | 2007-01-25 |
| AU2005292314A1 (en) | 2006-04-13 |
| US7205296B2 (en) | 2007-04-17 |
| JP2008514703A (ja) | 2008-05-08 |
| CN101031565B (zh) | 2010-09-29 |
| US20060069093A1 (en) | 2006-03-30 |
| CN101031565A (zh) | 2007-09-05 |
| AU2005292314B2 (en) | 2011-11-03 |
| WO2006039212A2 (en) | 2006-04-13 |
| IL182180A0 (en) | 2007-07-24 |
| HK1111414A1 (en) | 2008-08-08 |
| CA2581638A1 (en) | 2006-04-13 |
| EP1812429A2 (en) | 2007-08-01 |
| KR20070064356A (ko) | 2007-06-20 |
| EP1812429A4 (en) | 2010-07-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) | ||
| LAPS | Patent lapsed |