PH26924A - Excitatory amino acid antagonists - Google Patents
Excitatory amino acid antagonists Download PDFInfo
- Publication number
- PH26924A PH26924A PH40411A PH40411A PH26924A PH 26924 A PH26924 A PH 26924A PH 40411 A PH40411 A PH 40411A PH 40411 A PH40411 A PH 40411A PH 26924 A PH26924 A PH 26924A
- Authority
- PH
- Philippines
- Prior art keywords
- compound
- carboxy
- represented
- acid
- composition according
- Prior art date
Links
- 239000003194 amino acid receptor blocking agent Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 60
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 235000019260 propionic acid Nutrition 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 230000006378 damage Effects 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 230000003042 antagnostic effect Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- -1 propio Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000003556 anti-epileptic effect Effects 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 230000002461 excitatory amino acid Effects 0.000 claims description 2
- 239000003257 excitatory amino acid Substances 0.000 claims description 2
- 230000003405 preventing effect Effects 0.000 claims description 2
- 229940095574 propionic acid Drugs 0.000 claims 11
- QOQGUYAEXRBZQN-UHFFFAOYSA-N 2,3-dichloro-1h-indole Chemical compound C1=CC=C2C(Cl)=C(Cl)NC2=C1 QOQGUYAEXRBZQN-UHFFFAOYSA-N 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 claims 1
- 101000635799 Homo sapiens Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Proteins 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 abstract description 4
- 150000002475 indoles Chemical class 0.000 abstract description 4
- 235000013350 formula milk Nutrition 0.000 description 14
- 206010010904 Convulsion Diseases 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940099112 cornstarch Drugs 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 230000001146 hypoxic effect Effects 0.000 description 3
- RRBFPHJDLBGJRG-UHFFFAOYSA-N 3-(2-carboxyethyl)-6-hydroxy-1h-indole-2-carboxylic acid Chemical compound OC1=CC=C2C(CCC(=O)O)=C(C(O)=O)NC2=C1 RRBFPHJDLBGJRG-UHFFFAOYSA-N 0.000 description 2
- JDWKWISULBCGBB-UHFFFAOYSA-N 3-(2-carboxyethyl)-7-chloro-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(CCC(=O)O)=C(C(O)=O)NC2=C1Cl JDWKWISULBCGBB-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000002964 excitative effect Effects 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
- 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 1
- 206010003497 Asphyxia Diseases 0.000 description 1
- 206010049612 Autonomic seizure Diseases 0.000 description 1
- 102100026189 Beta-galactosidase Human genes 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 101150043532 CISH gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 108090001069 Chymopapain Proteins 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 238000011767 DBA/2J (JAX™ mouse strain) Methods 0.000 description 1
- 206010013647 Drowning Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 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
- 239000004471 Glycine Substances 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 1
- 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 1
- 206010061216 Infarction Diseases 0.000 description 1
- 108010059881 Lactase Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 208000037012 Psychomotor seizures Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 241001441724 Tetraodontidae Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 108010005774 beta-Galactosidase Proteins 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000006931 brain damage Effects 0.000 description 1
- 231100000874 brain damage Toxicity 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 1
- 201000008980 hyperinsulinism Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940116108 lactase Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000003140 lateral ventricle Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
- 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Organic Chemistry (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/342,498 US4960786A (en) | 1989-04-24 | 1989-04-24 | Excitatory amino acid antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PH26924A true PH26924A (en) | 1992-12-03 |
Family
ID=23342092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PH40411A PH26924A (en) | 1989-04-24 | 1990-04-24 | Excitatory amino acid antagonists |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4960786A (es) |
| EP (1) | EP0394905B1 (es) |
| JP (1) | JPH02295924A (es) |
| KR (1) | KR0164434B1 (es) |
| AT (1) | ATE126436T1 (es) |
| AU (1) | AU625998B2 (es) |
| DE (1) | DE69021618T2 (es) |
| DK (1) | DK0394905T3 (es) |
| ES (1) | ES2078257T3 (es) |
| GR (1) | GR3017792T3 (es) |
| IE (1) | IE66722B1 (es) |
| PH (1) | PH26924A (es) |
| ZA (1) | ZA902928B (es) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0347123A (ja) * | 1989-05-05 | 1991-02-28 | G D Searle & Co | インドール―２―カルボキシレート化合物類を含有するｃｎｓ疾患治療用組成物 |
| US5051442A (en) * | 1990-04-25 | 1991-09-24 | Merrell Dow Pharmaceuticals Inc. | 3-indolyl thioacetate derivatives and NMDA receptor antagonistic use thereof |
| CA2087091C (en) * | 1990-07-16 | 2001-09-11 | Francesco G. Salituro | Excitatory amino acid antagonists |
| US5189054A (en) * | 1990-11-02 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | 3-amidoindolyl derivatives and pharmaceutical compositions thereof |
| US5284862A (en) * | 1991-03-18 | 1994-02-08 | Warner-Lambert Company | Derivatives of 2-carboxyindoles having pharmaceutical activity |
| US5145845A (en) * | 1991-05-14 | 1992-09-08 | Warner-Lambert Co. | Substituted 2-carboxylindoles having pharmaceutical activity |
| US5318985A (en) * | 1991-12-20 | 1994-06-07 | Merrell Dow Pharmaceuticals Inc. | Potentiation of NMDA antagonists |
| GB9208492D0 (en) * | 1992-04-16 | 1992-06-03 | Glaxo Spa | Heterocyclic compounds |
| US5464843A (en) * | 1992-06-23 | 1995-11-07 | G.D. Searle & Co. | Imidazo[1,2-a]pyridinyldiacid compounds for cognitive enhancement and for treatment of cognitive disorders and neutrotoxic injury |
| GB9304500D0 (en) * | 1993-03-05 | 1993-04-21 | Glaxo Spa | Heterocyclic compounds |
| GB9321221D0 (en) * | 1993-10-14 | 1993-12-01 | Glaxo Spa | Heterocyclic compounds |
| TW280819B (es) * | 1993-11-17 | 1996-07-11 | Sumitomo Pharma | |
| GB9523999D0 (en) * | 1995-11-23 | 1996-01-24 | Lilly Co Eli | Indolyl neuropeptide y receptor antagonists |
| JP4603667B2 (ja) * | 2000-09-18 | 2010-12-22 | Ｊｕｋｉ株式会社 | 根巻きボタン付けミシン |
| US20030162825A1 (en) * | 2001-11-09 | 2003-08-28 | Sepracor Inc. | D-amino acid oxidase inhibitors for learning and memory |
| SE0302035D0 (sv) * | 2003-07-09 | 2003-07-09 | Biolipox Ab | New compound |
| PL380887A1 (pl) | 2003-12-29 | 2007-04-02 | Sepracor Inc. | Pirolowe i pirazolowe inhibitory DAAO |
| ATE430132T1 (de) * | 2004-06-18 | 2009-05-15 | Biolipox Ab | Zur behandlung von entzündungen geeignete indole |
| US20080188473A1 (en) * | 2004-06-18 | 2008-08-07 | Kristofer Olofsson | Indoles Useful in the Treatment of Inflammation |
| ATE405549T1 (de) * | 2004-06-18 | 2008-09-15 | Biolipox Ab | Zur behandlung von entzündungen geeignete indole |
| US20100197687A1 (en) * | 2005-01-19 | 2010-08-05 | Benjamin Pelcman | Indoles Useful in the Treatment of Inflammation |
| US20090048285A1 (en) * | 2005-01-19 | 2009-02-19 | Benjamin Pelcman | Pyrrolopyridines Useful in the Treatment of Inflammation |
| CN101142185A (zh) * | 2005-01-19 | 2008-03-12 | 比奥里波克斯公司 | 用于炎症治疗的吲哚 |
| WO2006077412A1 (en) * | 2005-01-19 | 2006-07-27 | Biolipox Ab | Thienopyrroles useful in the treatment of inflammation |
| US20080249091A1 (en) * | 2005-01-19 | 2008-10-09 | Benjamin Pelcman | Indoles Useful in the Treatment of Inflammation |
| CA2594773A1 (en) * | 2005-01-19 | 2006-07-27 | Biolipox Ab | Indoles useful in the treatment of inflammation |
| US7884124B2 (en) * | 2006-06-30 | 2011-02-08 | Sepracor Inc. | Fluoro-substituted inhibitors of D-amino acid oxidase |
| US7579370B2 (en) * | 2006-06-30 | 2009-08-25 | Sepracor Inc. | Fused heterocycles |
| EP2567698B1 (en) | 2011-09-07 | 2014-02-12 | Rheinische Friedrich-Wilhelms-Universität Bonn | GPR 17 agonists and screening assay |
| EP3427729A1 (en) | 2017-07-13 | 2019-01-16 | Paris Sciences et Lettres - Quartier Latin | Probenecid for use in treating epileptic diseases, disorders or conditions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3544563A (en) * | 1966-03-15 | 1970-12-01 | Sumitomo Chemical Co | Certain 3-indolyl-lower-alkanoic acid derivatives |
| US3578669A (en) * | 1969-09-16 | 1971-05-11 | Sterling Drug Inc | 1-((2 - substituted - 3 - indolyl) - lower-alkanoyl) - cycloalkyl - lower-alkylpiperidines and 1 - ((2 - hydroxymethyl-3 - indolyl)-lower-alkayl)-cycloalkyl-lower-alkylpiperidines |
| AT352708B (de) * | 1976-10-04 | 1979-10-10 | Frantsits Werner J Dipl Ing | Verfahren zur herstellung neuer indolderivate |
| IT1206078B (it) * | 1987-06-03 | 1989-04-14 | Polifarma Spa | Procedimento per la produzione di acido 3-indolpiruvico e suoi derivati loro uso farmaceutico |
-
1989
- 1989-04-24 US US07/342,498 patent/US4960786A/en not_active Expired - Fee Related
-
1990
- 1990-04-18 ZA ZA902928A patent/ZA902928B/xx unknown
- 1990-04-20 AU AU53780/90A patent/AU625998B2/en not_active Ceased
- 1990-04-20 JP JP2103199A patent/JPH02295924A/ja active Pending
- 1990-04-21 KR KR1019900005614A patent/KR0164434B1/ko not_active IP Right Cessation
- 1990-04-23 DE DE69021618T patent/DE69021618T2/de not_active Expired - Fee Related
- 1990-04-23 AT AT90107633T patent/ATE126436T1/de not_active IP Right Cessation
- 1990-04-23 EP EP90107633A patent/EP0394905B1/en not_active Expired - Lifetime
- 1990-04-23 DK DK90107633.1T patent/DK0394905T3/da active
- 1990-04-23 ES ES90107633T patent/ES2078257T3/es not_active Expired - Lifetime
- 1990-04-23 IE IE143790A patent/IE66722B1/en not_active IP Right Cessation
- 1990-04-24 PH PH40411A patent/PH26924A/en unknown
-
1995
- 1995-10-18 GR GR950402895T patent/GR3017792T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0394905A3 (en) | 1992-01-22 |
| DK0394905T3 (da) | 1995-09-18 |
| ATE126436T1 (de) | 1995-09-15 |
| DE69021618T2 (de) | 1996-01-18 |
| DE69021618D1 (de) | 1995-09-21 |
| AU625998B2 (en) | 1992-07-23 |
| EP0394905B1 (en) | 1995-08-16 |
| KR0164434B1 (ko) | 1999-01-15 |
| AU5378090A (en) | 1990-10-25 |
| GR3017792T3 (en) | 1996-01-31 |
| IE66722B1 (en) | 1996-01-24 |
| IE901437L (en) | 1990-10-24 |
| ES2078257T3 (es) | 1995-12-16 |
| JPH02295924A (ja) | 1990-12-06 |
| ZA902928B (en) | 1991-02-27 |
| US4960786A (en) | 1990-10-02 |
| EP0394905A2 (en) | 1990-10-31 |
| KR900015729A (ko) | 1990-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PH26924A (en) | Excitatory amino acid antagonists | |
| US5026700A (en) | Certain quinolines and thienopyridines as excitatory amino acid antagonists | |
| DE69118388T2 (de) | Substituierte bizyklische arylderivate mit selektiver leukotrien b4 antagonistischer wirkung | |
| AU646686B2 (en) | Excitatory amino acid antagonistic indole derivatives | |
| US6194428B1 (en) | Use of 5-substituted pyridine and hexahydroquinoline-3 carboxylic acid derivatives for treating diseases of the central nervous system | |
| JP3014001B2 (ja) | 興奮性アミノ酸拮抗剤 | |
| KR0178281B1 (ko) | 3-인돌릴 티오아세테이트 유도체 및 이를 함유하는 약제학적 조성물 | |
| EP0501378B1 (en) | NMDA Antagonists | |
| CN105873439A (zh) | RORγt的烷基连接的喹啉基调节剂 | |
| US5373015A (en) | Fused pyridine derivatives useful as angiotensin II antagonists | |
| JP4231107B2 (ja) | 抗ウイルス作用を有する置換キノリン誘導体 | |
| AU599829B2 (en) | 4-oxo-3-quinolinecarboxylic acids useful as antibacterial agents and preparation thereof | |
| KR930009355B1 (ko) | 피리도[1, 2-a]피리미딘 유도체의 제조법 | |
| US5547991A (en) | NMDA antagonism method | |
| US5668143A (en) | Heterocyclic benzenesulfonylimine derivatives as inhibitors of IL-1 action | |
| US5112821A (en) | Excitatory amino acid antagonists which are certain thienopyridives | |
| JPH037280A (ja) | 新規ベンゾチオピラニルアミン | |
| CZ286649B6 (cs) | 2-(aminomethyl)-3,4,7,9-tetrahydro-2H-pyrano-/2,3-e/indol-8-onové deriváty a farmaceutický prostředek s jejich obsahem | |
| US5360814A (en) | NMDA antagonists | |
| JP2001097866A (ja) | 抗ヘリコバクター・ピロリ剤 |