JPH11508902A - 新規キノキサリン−およびキノキサリンアルカン−ホスホン酸 - Google Patents
新規キノキサリン−およびキノキサリンアルカン−ホスホン酸Info
- Publication number
- JPH11508902A JPH11508902A JP9505465A JP50546597A JPH11508902A JP H11508902 A JPH11508902 A JP H11508902A JP 9505465 A JP9505465 A JP 9505465A JP 50546597 A JP50546597 A JP 50546597A JP H11508902 A JPH11508902 A JP H11508902A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- dioxo
- tetrahydro
- free
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical class 0.000 claims abstract description 23
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 claims abstract description 6
- 230000001575 pathological effect Effects 0.000 claims abstract description 3
- -1 nitro, carboxy Chemical group 0.000 claims description 133
- 150000001875 compounds Chemical class 0.000 claims description 93
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
- 239000002253 acid Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 208000005392 Spasm Diseases 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- QIKGBPGSUJXLBC-UHFFFAOYSA-N 4-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-3-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C=CCCP(O)(=O)O QIKGBPGSUJXLBC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005109 alkynylthio group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 206010010904 Convulsion Diseases 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 125000005108 alkenylthio group Chemical group 0.000 claims description 3
- 230000036461 convulsion Effects 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 claims description 3
- GZDJSOJULKHOIW-UHFFFAOYSA-N 1-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C(C)P(O)(O)=O GZDJSOJULKHOIW-UHFFFAOYSA-N 0.000 claims description 2
- KLCJLGDHDKNRFF-UHFFFAOYSA-N 1-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2C(C)P(O)(O)=O KLCJLGDHDKNRFF-UHFFFAOYSA-N 0.000 claims description 2
- BABPOUFHWOCNNS-UHFFFAOYSA-N 2-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethenylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C=CP(O)(=O)O BABPOUFHWOCNNS-UHFFFAOYSA-N 0.000 claims description 2
- OCFXRQBTOUGKRB-UHFFFAOYSA-N 2-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCP(O)(=O)O OCFXRQBTOUGKRB-UHFFFAOYSA-N 0.000 claims description 2
- ZQBFDFCRRKCWPN-UHFFFAOYSA-N 2-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethenylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2C=CP(O)(=O)O ZQBFDFCRRKCWPN-UHFFFAOYSA-N 0.000 claims description 2
- CXGBVHWGXKKZTM-UHFFFAOYSA-N 2-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CCP(O)(=O)O CXGBVHWGXKKZTM-UHFFFAOYSA-N 0.000 claims description 2
- RMDXKUMEYLOUJB-UHFFFAOYSA-N 3-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C=CCP(O)(=O)O RMDXKUMEYLOUJB-UHFFFAOYSA-N 0.000 claims description 2
- IRMAUQFNMCPNKR-UHFFFAOYSA-N 3-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)propylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCCP(O)(=O)O IRMAUQFNMCPNKR-UHFFFAOYSA-N 0.000 claims description 2
- PZKZUTUIEQATQD-UHFFFAOYSA-N 3-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2C=CCP(O)(=O)O PZKZUTUIEQATQD-UHFFFAOYSA-N 0.000 claims description 2
- UWZRCGOFRIWUQT-UHFFFAOYSA-N 3-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)propylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCCP(O)(=O)O UWZRCGOFRIWUQT-UHFFFAOYSA-N 0.000 claims description 2
- OARFPQNKOLGYHZ-UHFFFAOYSA-N 3-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-enylphosphonic acid Chemical compound ClC1=CC(=C2NC(C(NC2=C1)=O)=O)C=CCP(O)(=O)O OARFPQNKOLGYHZ-UHFFFAOYSA-N 0.000 claims description 2
- DIWCSSZWIWIHJC-UHFFFAOYSA-N 4-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-1-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCC=CP(O)(=O)O DIWCSSZWIWIHJC-UHFFFAOYSA-N 0.000 claims description 2
- WTGPQJYRMFTPLH-UHFFFAOYSA-N 4-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)butylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2CCCCP(O)(=O)O WTGPQJYRMFTPLH-UHFFFAOYSA-N 0.000 claims description 2
- GHZGLYPWKLGARA-UHFFFAOYSA-N 4-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-1-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCC=CP(O)(=O)O GHZGLYPWKLGARA-UHFFFAOYSA-N 0.000 claims description 2
- BFXXCDKGBWJVRM-UHFFFAOYSA-N 4-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-3-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2C=CCCP(O)(=O)O BFXXCDKGBWJVRM-UHFFFAOYSA-N 0.000 claims description 2
- UCOYQIJKIGUGSB-UHFFFAOYSA-N 4-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-1-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CCC=CP(O)(=O)O UCOYQIJKIGUGSB-UHFFFAOYSA-N 0.000 claims description 2
- MQGNUGIYISGXJZ-UHFFFAOYSA-N 4-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)but-3-enylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2C=CCCP(O)(=O)O MQGNUGIYISGXJZ-UHFFFAOYSA-N 0.000 claims description 2
- 201000006474 Brain Ischemia Diseases 0.000 claims description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
- 206010047163 Vasospasm Diseases 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 230000002792 vascular Effects 0.000 claims description 2
- 241000506319 Trifur Species 0.000 claims 2
- 208000023589 ischemic disease Diseases 0.000 claims 2
- AVMVKAVAFKFBNZ-UHFFFAOYSA-N 1-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2C(C)P(O)(O)=O AVMVKAVAFKFBNZ-UHFFFAOYSA-N 0.000 claims 1
- QNQPLCIZACNUQH-UHFFFAOYSA-N 2-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethenylphosphonic acid Chemical compound OP(O)(=O)C=Cc1cc(Br)cc2[nH]c(=O)c(=O)[nH]c12 QNQPLCIZACNUQH-UHFFFAOYSA-N 0.000 claims 1
- IMIQAHTWYJCSJN-UHFFFAOYSA-N 2-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)ethylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCP(O)(=O)O IMIQAHTWYJCSJN-UHFFFAOYSA-N 0.000 claims 1
- WZMNUVQQLLZLDG-UHFFFAOYSA-N 4-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)butylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2CCCCP(O)(=O)O WZMNUVQQLLZLDG-UHFFFAOYSA-N 0.000 claims 1
- BJZGWDAAMWNEPG-UHFFFAOYSA-N 4-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)butylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CCCCP(O)(=O)O BJZGWDAAMWNEPG-UHFFFAOYSA-N 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- RZJBKZOZVVCNBR-UHFFFAOYSA-N sulfamoyl bromide Chemical compound NS(Br)(=O)=O RZJBKZOZVVCNBR-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
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- 239000011541 reaction mixture Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
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- 238000010992 reflux Methods 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 235000019441 ethanol Nutrition 0.000 description 13
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
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- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 108010010803 Gelatin Proteins 0.000 description 7
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 6
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
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- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
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- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
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- 239000002511 suppository base Substances 0.000 description 4
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- 235000012222 talc Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
- C07F9/650994—Six-membered rings having the nitrogen atoms in the positions 1 and 4 condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
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- 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
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- 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
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2009/95 | 1995-07-10 | ||
| CH200995 | 1995-07-10 | ||
| PCT/EP1996/002866 WO1997003079A1 (en) | 1995-07-10 | 1996-07-01 | Novel quinoxaline- and quinoxalinylalkane-phosphonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH11508902A true JPH11508902A (ja) | 1999-08-03 |
Family
ID=4223780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9505465A Pending JPH11508902A (ja) | 1995-07-10 | 1996-07-01 | 新規キノキサリン−およびキノキサリンアルカン−ホスホン酸 |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0837864A1 (cs) |
| JP (1) | JPH11508902A (cs) |
| KR (1) | KR19990028839A (cs) |
| AU (1) | AU6516296A (cs) |
| BR (1) | BR9609644A (cs) |
| CA (1) | CA2224718A1 (cs) |
| CZ (1) | CZ5398A3 (cs) |
| HU (1) | HUP9901345A3 (cs) |
| IL (1) | IL122872A0 (cs) |
| NO (1) | NO980095L (cs) |
| PL (1) | PL324340A1 (cs) |
| SK (1) | SK2798A3 (cs) |
| TR (1) | TR199800022T1 (cs) |
| WO (1) | WO1997003079A1 (cs) |
| ZA (1) | ZA965800B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TR199900897T2 (xx) * | 1996-10-24 | 1999-07-21 | Novartis Ag | Ornat�lm�� aminoalkanfosfonik asitler. |
| US6841684B2 (en) | 1997-12-04 | 2005-01-11 | Allergan, Inc. | Imidiazoles having reduced side effects |
| US6329369B1 (en) | 1997-12-04 | 2001-12-11 | Allergan Sales, Inc. | Methods of treating pain and other conditions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5118675A (en) * | 1991-02-15 | 1992-06-02 | American Home Products Corporation | Quinoxaline phosphono-amino acids |
| IL109397A0 (en) * | 1993-04-28 | 1994-07-31 | Schering Ag | Quinoxalinedione derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same |
-
1996
- 1996-07-01 HU HU9901345A patent/HUP9901345A3/hu unknown
- 1996-07-01 TR TR1998/00022T patent/TR199800022T1/xx unknown
- 1996-07-01 SK SK27-98A patent/SK2798A3/sk unknown
- 1996-07-01 JP JP9505465A patent/JPH11508902A/ja active Pending
- 1996-07-01 WO PCT/EP1996/002866 patent/WO1997003079A1/en not_active Ceased
- 1996-07-01 AU AU65162/96A patent/AU6516296A/en not_active Abandoned
- 1996-07-01 PL PL96324340A patent/PL324340A1/xx unknown
- 1996-07-01 EP EP96924829A patent/EP0837864A1/en not_active Withdrawn
- 1996-07-01 BR BR9609644A patent/BR9609644A/pt not_active Application Discontinuation
- 1996-07-01 IL IL12287296A patent/IL122872A0/xx unknown
- 1996-07-01 CZ CZ9853A patent/CZ5398A3/cs unknown
- 1996-07-01 CA CA002224718A patent/CA2224718A1/en not_active Abandoned
- 1996-07-01 KR KR1019980700140A patent/KR19990028839A/ko not_active Withdrawn
- 1996-07-09 ZA ZA965800A patent/ZA965800B/xx unknown
-
1998
- 1998-01-09 NO NO980095A patent/NO980095L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA965800B (en) | 1997-01-10 |
| AU6516296A (en) | 1997-02-10 |
| PL324340A1 (en) | 1998-05-25 |
| BR9609644A (pt) | 1999-05-11 |
| MX9800332A (es) | 1998-07-31 |
| SK2798A3 (en) | 1998-07-08 |
| HUP9901345A3 (en) | 2000-01-28 |
| TR199800022T1 (xx) | 1998-05-21 |
| CA2224718A1 (en) | 1997-01-30 |
| NO980095L (no) | 1998-03-05 |
| HUP9901345A2 (hu) | 1999-08-30 |
| NO980095D0 (no) | 1998-01-09 |
| WO1997003079A1 (en) | 1997-01-30 |
| EP0837864A1 (en) | 1998-04-29 |
| CZ5398A3 (cs) | 1998-06-17 |
| KR19990028839A (ko) | 1999-04-15 |
| IL122872A0 (en) | 1998-08-16 |
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