OA11189A - Quinoxalinediones. - Google Patents

Quinoxalinediones. Download PDF

Info

Publication number: OA11189A
Authority: OA; OAPI
Prior art keywords: formula; compound; solvaté; group; acceptable sait
Prior art date: 1997-02-27

Application number

OA9900192A

Other languages

English (en)

Inventor

Robert James Crook

Elisabeth Colette Loui Gautier

Alan Stobie

David Charles Waite

Original Assignee

Pfizer

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.)

1997-02-27

Filing date

1999-08-23

Publication date

2003-05-14

1997-02-27 Priority claimed from PCT/EP1997/000995 external-priority patent/WO1997032873A1/fr

1997-07-25 Priority claimed from GBGB9715783.8A external-priority patent/GB9715783D0/en

1999-08-23 Application filed by Pfizer filed Critical Pfizer

2003-05-14 Publication of OA11189A publication Critical patent/OA11189A/en

Links

SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical class C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 title claims description 4
239000000203 mixture Substances 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 25
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 claims abstract description 11
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims abstract description 11
239000005557 antagonist Substances 0.000 claims abstract description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
208000012902 Nervous system disease Diseases 0.000 claims abstract description 4
230000001684 chronic effect Effects 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 85
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 10
238000007254 oxidation reaction Methods 0.000 claims description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
239000000377 silicon dioxide Substances 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
239000011734 sodium Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
230000000626 neurodegenerative effect Effects 0.000 claims description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 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
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
238000010626 work up procedure Methods 0.000 claims 1
230000001154 acute effect Effects 0.000 abstract description 4
ABJFBJGGLJVMAQ-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dione Chemical class C1=CC=C2NC(=O)C(=O)NC2=C1 ABJFBJGGLJVMAQ-UHFFFAOYSA-N 0.000 abstract description 2
UYDXSMVRMPWOKX-UHFFFAOYSA-N 5-(2H-triazol-4-yl)-1,4-dihydroquinoxaline-2,3-dione Chemical class C=12NC(=O)C(=O)NC2=CC=CC=1C1=CNN=N1 UYDXSMVRMPWOKX-UHFFFAOYSA-N 0.000 abstract description 2
208000025966 Neurological disease Diseases 0.000 abstract 1
230000004770 neurodegeneration Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
239000007787 solid Substances 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 23
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 0.000 description 15
229940093499 ethyl acetate Drugs 0.000 description 14
235000019439 ethyl acetate Nutrition 0.000 description 14
238000001914 filtration Methods 0.000 description 12
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 10
239000004471 Glycine Substances 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
235000011054 acetic acid Nutrition 0.000 description 9
239000000725 suspension Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
235000011167 hydrochloric acid Nutrition 0.000 description 8
229960000443 hydrochloric acid Drugs 0.000 description 8
150000003839 salts Chemical class 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
238000012360 testing method Methods 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
IEMAQDHGZOPMNI-UHFFFAOYSA-N 6,7-dichloro-5-[3-(methoxymethyl)-5-(1-oxidopyridin-1-ium-3-yl)-1,2,4-triazol-4-yl]-1,4-dihydroquinoxaline-2,3-dione Chemical compound ClC=1C(Cl)=CC=2NC(=O)C(=O)NC=2C=1N1C(COC)=NN=C1C1=CC=C[N+]([O-])=C1 IEMAQDHGZOPMNI-UHFFFAOYSA-N 0.000 description 4
YDYJCQIIFXPRMI-UHFFFAOYSA-N 6,7-dichloro-5-[3-(methoxymethyl)-5-pyridin-3-yl-1,2,4-triazol-4-yl]-1,4-dihydroquinoxaline-2,3-dione Chemical compound ClC=1C(Cl)=CC=2NC(=O)C(=O)NC=2C=1N1C(COC)=NN=C1C1=CC=CN=C1 YDYJCQIIFXPRMI-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000000499 gel Substances 0.000 description 4
229960002989 glutamic acid Drugs 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
239000000047 product Substances 0.000 description 4
-1 pyrrol-1-yl-substituted 2,3(1 H,4H)-quinoxalinedione Chemical class 0.000 description 4
FMCGSUUBYTWNDP-ONGXEEELSA-N (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol Chemical compound CN(C)[C@@H](C)[C@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-ONGXEEELSA-N 0.000 description 3
FMCGSUUBYTWNDP-MWLCHTKSSA-N (1s,2r)-2-(dimethylamino)-1-phenylpropan-1-ol Chemical compound CN(C)[C@H](C)[C@@H](O)C1=CC=CC=C1 FMCGSUUBYTWNDP-MWLCHTKSSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
102000003678 AMPA Receptors Human genes 0.000 description 3
108090000078 AMPA Receptors Proteins 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000013922 glutamic acid Nutrition 0.000 description 3
239000004220 glutamic acid Substances 0.000 description 3
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
239000012528 membrane Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000002287 radioligand Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000002441 reversible effect Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
GYQDMMSNDKWZLY-UHFFFAOYSA-N 2,3,6,7-tetrachloro-5-nitroquinoxaline Chemical compound ClC1=C(Cl)N=C2C([N+](=O)[O-])=C(Cl)C(Cl)=CC2=N1 GYQDMMSNDKWZLY-UHFFFAOYSA-N 0.000 description 2
DXXBFAXBSVZRKA-UHFFFAOYSA-N 2,3,6,7-tetrachloroquinoxalin-5-amine Chemical compound ClC1=C(Cl)N=C2C(N)=C(Cl)C(Cl)=CC2=N1 DXXBFAXBSVZRKA-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 2
JSFLFNPZGIDUBV-UHFFFAOYSA-N 3-(2-amino-3-hydroxy-5-methyl-3h-1,2-oxazol-4-yl)propanoic acid Chemical compound CC1=C(CCC(O)=O)C(O)N(N)O1 JSFLFNPZGIDUBV-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000006184 cosolvent Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 2
JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000010828 elution Methods 0.000 description 2
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229960002163 hydrogen peroxide Drugs 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
208000028867 ischemia Diseases 0.000 description 2
239000000463 material Substances 0.000 description 2
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
ZEXZHNILDWIHLO-UHFFFAOYSA-N n-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-2-methoxyacetamide Chemical compound COC1=C(OC)N=C2C(NC(=O)COC)=C(Cl)C(Cl)=CC2=N1 ZEXZHNILDWIHLO-UHFFFAOYSA-N 0.000 description 2
FBZLGSDHOFJDNS-UHFFFAOYSA-N n-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-2-methoxyethanethioamide Chemical compound COC1=C(OC)N=C2C(NC(=S)COC)=C(Cl)C(Cl)=CC2=N1 FBZLGSDHOFJDNS-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000012188 paraffin wax Substances 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229960001922 sodium perborate Drugs 0.000 description 2
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 2
PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
ILZYIIMHGLHXQZ-UHFFFAOYSA-N 6,7-dichloro-2,3-dimethoxy-5-[3-(methoxymethyl)-5-pyridin-3-yl-1,2,4-triazol-4-yl]quinoxaline Chemical compound ClC=1C(Cl)=CC2=NC(OC)=C(OC)N=C2C=1N1C(COC)=NN=C1C1=CC=CN=C1 ILZYIIMHGLHXQZ-UHFFFAOYSA-N 0.000 description 1
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USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
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OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
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 1
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229910003641 H2SiO3 Inorganic materials 0.000 description 1
206010019196 Head injury Diseases 0.000 description 1
208000016621 Hearing disease Diseases 0.000 description 1
208000010496 Heart Arrest Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
206010061216 Infarction Diseases 0.000 description 1
VLSMHEGGTFMBBZ-OOZYFLPDSA-M Kainate Chemical compound CC(=C)[C@H]1C[NH2+][C@H](C([O-])=O)[C@H]1CC([O-])=O VLSMHEGGTFMBBZ-OOZYFLPDSA-M 0.000 description 1
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239000008103 glucose Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
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QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
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CHFSOFHQIZKQCR-UHFFFAOYSA-N licostinel Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C(Cl)=C2[N+](=O)[O-] CHFSOFHQIZKQCR-UHFFFAOYSA-N 0.000 description 1
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230000000472 traumatic effect Effects 0.000 description 1
PIEPQKCYPFFYMG-UHFFFAOYSA-N tris acetate Chemical compound CC(O)=O.OCC(N)(CO)CO PIEPQKCYPFFYMG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
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Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Vascular Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Psychology (AREA)
Urology & Nephrology (AREA)
Addiction (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Luminescent Compositions (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

OA9900192A 1997-02-27 1999-08-23 Quinoxalinediones. OA11189A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/EP1997/000995 WO1997032873A1 (fr)	1996-03-09	1997-02-27	Quinoxalinediones
GBGB9715783.8A GB9715783D0 (en)	1997-02-27	1997-07-25	Quinoxalinediones

Publications (1)

Publication Number	Publication Date
OA11189A true OA11189A (en)	2003-05-14

Family

ID=10816496

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900192A OA11189A (en)	1997-02-27	1999-08-23	Quinoxalinediones.

Country Status (13)

Country	Link
US (1)	US6333326B1 (fr)
KR (1)	KR100375112B1 (fr)
AP (1)	AP982A (fr)
AU (1)	AU723467B2 (fr)
DZ (1)	DZ2437A1 (fr)
EA (1)	EA001658B1 (fr)
GT (1)	GT199800045A (fr)
IL (1)	IL131120A0 (fr)
IS (1)	IS5142A (fr)
MA (1)	MA26474A1 (fr)
OA (1)	OA11189A (fr)
PL (1)	PL335501A1 (fr)
UA (1)	UA58534C2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3873746B2 (ja) *	2000-05-19	2007-01-24	アステラス製薬株式会社	トリアゾール誘導体
US20040082543A1 (en) *	2002-10-29	2004-04-29	Pharmacia Corporation	Compositions of cyclooxygenase-2 selective inhibitors and NMDA receptor antagonists for the treatment or prevention of neuropathic pain
US8603980B2 (en)	2007-01-16	2013-12-10	The Johns Hopkins University	Glutamate receptor antagonists and methods of use
CN104370834B (zh)	2007-05-17	2017-04-19	株式会社半导体能源研究所	三唑衍生物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5158846A (en)	1990-10-29	1992-10-27	Olin Corporation	Electrostatic color printing system utilizing an image transfer belt
IT1243990B (it) *	1990-10-30	1994-06-28	Minnesota Mining & Mfg	Procedimento per preparare prodotti del bisfenolo fluorene
CA2095444C (fr) *	1990-11-06	2001-06-19	Shuichi Sakamoto	Derives de condensation avec la pyrazine
GB9605027D0 (en)	1996-03-09	1996-05-08	Pfizer Ltd	Quinoxalinediones

1997
- 1997-02-27 AP APAP/P/1998/001201A patent/AP982A/en active
1998
- 1998-02-24 EA EA199900688A patent/EA001658B1/ru not_active IP Right Cessation
- 1998-02-24 PL PL98335501A patent/PL335501A1/xx unknown
- 1998-02-24 IL IL13112098A patent/IL131120A0/xx unknown
- 1998-02-24 UA UA99084653A patent/UA58534C2/uk unknown
- 1998-02-24 US US09/367,303 patent/US6333326B1/en not_active Expired - Fee Related
- 1998-02-24 AU AU68279/98A patent/AU723467B2/en not_active Ceased
- 1998-02-24 KR KR10-1999-7007786A patent/KR100375112B1/ko not_active Expired - Fee Related
- 1998-02-25 DZ DZ980047A patent/DZ2437A1/fr active
- 1998-02-25 MA MA24980A patent/MA26474A1/fr unknown
- 1998-02-26 GT GT199800045A patent/GT199800045A/es unknown
1999
- 1999-07-30 IS IS5142A patent/IS5142A/is unknown
- 1999-08-23 OA OA9900192A patent/OA11189A/en unknown

Also Published As

Publication number	Publication date
KR20000075717A (ko)	2000-12-26
AP982A (en)	2001-07-16
EA001658B1 (ru)	2001-06-25
UA58534C2 (uk)	2003-08-15
HK1025317A1 (en)	2000-11-10
IL131120A0 (en)	2001-01-28
GT199800045A (es)	1999-08-20
EA199900688A1 (ru)	2000-04-24
MA26474A1 (fr)	2004-12-20
US6333326B1 (en)	2001-12-25
AU6827998A (en)	1998-09-18
KR100375112B1 (ko)	2003-03-08
IS5142A (is)	1999-07-30
AU723467B2 (en)	2000-08-24
PL335501A1 (en)	2000-04-25
DZ2437A1 (fr)	2003-01-11

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AU2005213538A1 (en)	2005-08-25	Piperidinylcarbonyl-pyrrolidines and their use as melanocortin agonists
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