CA2224718A1 - Novel quinoxaline- and quinoxalinylalkane-phosphonic acids - Google Patents
Novel quinoxaline- and quinoxalinylalkane-phosphonic acids Download PDFInfo
- Publication number
- CA2224718A1 CA2224718A1 CA002224718A CA2224718A CA2224718A1 CA 2224718 A1 CA2224718 A1 CA 2224718A1 CA 002224718 A CA002224718 A CA 002224718A CA 2224718 A CA2224718 A CA 2224718A CA 2224718 A1 CA2224718 A1 CA 2224718A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- quinoxalin
- tetrahydro
- dioxo
- free
- 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.)
- Abandoned
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- 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 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 19
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
- 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
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 8
- 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 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
- 230000000903 blocking effect Effects 0.000 claims abstract description 3
- 230000001575 pathological effect Effects 0.000 claims abstract description 3
- -1 nitro, carboxy Chemical group 0.000 claims description 100
- 150000001875 compounds Chemical class 0.000 claims description 97
- 239000002253 acid Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 15
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 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
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000005109 alkynylthio group Chemical group 0.000 claims description 4
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- 208000035475 disorder Diseases 0.000 claims description 4
- 230000000302 ischemic effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 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
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000036461 convulsion Effects 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 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 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
- 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 description 2
- 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 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
- HCVMXBCSVAQMSV-UHFFFAOYSA-N 3-(2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-ynylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=CC=C2C#CCP(O)(=O)O HCVMXBCSVAQMSV-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
- APRVVQDTWFHFNQ-UHFFFAOYSA-N 3-(7-bromo-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-ynylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Br)C=C2C#CCP(O)(=O)O APRVVQDTWFHFNQ-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
- QWFWMKORGOPTMW-UHFFFAOYSA-N 3-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)prop-2-ynylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2C#CCP(O)(=O)O QWFWMKORGOPTMW-UHFFFAOYSA-N 0.000 claims description 2
- ANLZISNWTLVJFL-UHFFFAOYSA-N 3-(7-chloro-2,3-dioxo-1,4-dihydroquinoxalin-5-yl)propylphosphonic acid Chemical compound N1C(=O)C(=O)NC2=C1C=C(Cl)C=C2CCCP(O)(=O)O ANLZISNWTLVJFL-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
- 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 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
- 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 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 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 1
- 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 1
- 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 1
- 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 1
- 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 1
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- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
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- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- SEPKUNXLGWMPHL-UHFFFAOYSA-N quinoxaline-2,3-dione Chemical compound C1=CC=CC2=NC(=O)C(=O)N=C21 SEPKUNXLGWMPHL-UHFFFAOYSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—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)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Biochemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Molecular Biology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2009/95 | 1995-07-10 | ||
| CH200995 | 1995-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2224718A1 true CA2224718A1 (en) | 1997-01-30 |
Family
ID=4223780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002224718A Abandoned CA2224718A1 (en) | 1995-07-10 | 1996-07-01 | Novel quinoxaline- and quinoxalinylalkane-phosphonic acids |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0837864A1 (no) |
| JP (1) | JPH11508902A (no) |
| KR (1) | KR19990028839A (no) |
| AU (1) | AU6516296A (no) |
| BR (1) | BR9609644A (no) |
| CA (1) | CA2224718A1 (no) |
| CZ (1) | CZ5398A3 (no) |
| HU (1) | HUP9901345A3 (no) |
| IL (1) | IL122872A0 (no) |
| NO (1) | NO980095L (no) |
| PL (1) | PL324340A1 (no) |
| SK (1) | SK2798A3 (no) |
| TR (1) | TR199800022T1 (no) |
| WO (1) | WO1997003079A1 (no) |
| ZA (1) | ZA965800B (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3908790B2 (ja) * | 1996-10-24 | 2007-04-25 | ノバルティス アクチエンゲゼルシャフト | 置換アミノアルカンホスホン酸 |
| 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 SK SK27-98A patent/SK2798A3/sk unknown
- 1996-07-01 EP EP96924829A patent/EP0837864A1/en not_active Withdrawn
- 1996-07-01 AU AU65162/96A patent/AU6516296A/en not_active Abandoned
- 1996-07-01 PL PL96324340A patent/PL324340A1/xx unknown
- 1996-07-01 CA CA002224718A patent/CA2224718A1/en not_active Abandoned
- 1996-07-01 TR TR1998/00022T patent/TR199800022T1/xx unknown
- 1996-07-01 IL IL12287296A patent/IL122872A0/xx unknown
- 1996-07-01 CZ CZ9853A patent/CZ5398A3/cs unknown
- 1996-07-01 BR BR9609644A patent/BR9609644A/pt not_active Application Discontinuation
- 1996-07-01 HU HU9901345A patent/HUP9901345A3/hu unknown
- 1996-07-01 JP JP9505465A patent/JPH11508902A/ja active Pending
- 1996-07-01 WO PCT/EP1996/002866 patent/WO1997003079A1/en not_active Application Discontinuation
- 1996-07-01 KR KR1019980700140A patent/KR19990028839A/ko not_active Application Discontinuation
- 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 |
|---|---|
| JPH11508902A (ja) | 1999-08-03 |
| EP0837864A1 (en) | 1998-04-29 |
| PL324340A1 (en) | 1998-05-25 |
| KR19990028839A (ko) | 1999-04-15 |
| ZA965800B (en) | 1997-01-10 |
| TR199800022T1 (xx) | 1998-05-21 |
| SK2798A3 (en) | 1998-07-08 |
| HUP9901345A3 (en) | 2000-01-28 |
| IL122872A0 (en) | 1998-08-16 |
| CZ5398A3 (cs) | 1998-06-17 |
| HUP9901345A2 (hu) | 1999-08-30 |
| WO1997003079A1 (en) | 1997-01-30 |
| AU6516296A (en) | 1997-02-10 |
| BR9609644A (pt) | 1999-05-11 |
| NO980095D0 (no) | 1998-01-09 |
| NO980095L (no) | 1998-03-05 |
| MX9800332A (es) | 1998-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |