ZA200300135B - Pharmaceutical compositions for treating neurological disorders. - Google Patents
Pharmaceutical compositions for treating neurological disorders. Download PDFInfo
- Publication number
- ZA200300135B ZA200300135B ZA200300135A ZA200300135A ZA200300135B ZA 200300135 B ZA200300135 B ZA 200300135B ZA 200300135 A ZA200300135 A ZA 200300135A ZA 200300135 A ZA200300135 A ZA 200300135A ZA 200300135 B ZA200300135 B ZA 200300135B
- Authority
- ZA
- South Africa
- Prior art keywords
- tartaric acid
- substituted
- composition
- compound
- alkyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 24
- 208000012902 Nervous system disease Diseases 0.000 title description 3
- 208000025966 Neurological disease Diseases 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 104
- -1 bromobenzoyl-D-tartaric acid Chemical compound 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 229910052799 carbon Chemical group 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 230000003957 neurotransmitter release Effects 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 8
- 230000004075 alteration Effects 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229960001270 d- tartaric acid Drugs 0.000 claims 28
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 12
- NNNQNUXYOQZVDB-ZIAGYGMSSA-N (2r,3r)-2,3-bis(2,2-dimethylpropanoyl)-2,3-dihydroxybutanedioic acid Chemical compound CC(C)(C)C(=O)[C@@](O)(C(O)=O)[C@](O)(C(O)=O)C(=O)C(C)(C)C NNNQNUXYOQZVDB-ZIAGYGMSSA-N 0.000 claims 5
- OCQAXYHNMWVLRH-ROUUACIJSA-N (2s,3s)-2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound O=C([C@](O)(C(=O)O)[C@@](O)(C(O)=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 OCQAXYHNMWVLRH-ROUUACIJSA-N 0.000 claims 5
- BKLZIAYVINRQEJ-UHFFFAOYSA-K trifluoroalumane;trihydrate Chemical compound O.O.O.F[Al](F)F BKLZIAYVINRQEJ-UHFFFAOYSA-K 0.000 claims 5
- CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 claims 4
- OCQAXYHNMWVLRH-QZTJIDSGSA-N (2r,3r)-2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound O=C([C@@](O)(C(=O)O)[C@](O)(C(O)=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 OCQAXYHNMWVLRH-QZTJIDSGSA-N 0.000 claims 4
- CMIBUZBMZCBCAT-HOTGVXAUSA-N (2s,3s)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@H](C(O)=O)[C@@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HOTGVXAUSA-N 0.000 claims 4
- PEOCCFXRLGYKBM-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(OCO2)C2=C1 PEOCCFXRLGYKBM-UHFFFAOYSA-N 0.000 claims 4
- SNZMBGPVGUVXRP-UHFFFAOYSA-N 4,5-dichloroquinoline Chemical compound C1=CC(Cl)=C2C(Cl)=CC=CC2=N1 SNZMBGPVGUVXRP-UHFFFAOYSA-N 0.000 claims 4
- DVMNOSBSAVUYEU-WOJBJXKFSA-N C1(=CC(=CC=C1)C(=O)[C@@]([C@@](C(=O)O)(O)C(=O)C=1C=C(C=CC1)C)(O)C(=O)O)C Chemical compound C1(=CC(=CC=C1)C(=O)[C@@]([C@@](C(=O)O)(O)C(=O)C=1C=C(C=CC1)C)(O)C(=O)O)C DVMNOSBSAVUYEU-WOJBJXKFSA-N 0.000 claims 4
- 229960003753 nitric oxide Drugs 0.000 claims 4
- 235000019391 nitrogen oxide Nutrition 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229940125904 compound 1 Drugs 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
- 208000035475 disorder Diseases 0.000 description 23
- 241000894007 species Species 0.000 description 20
- 238000005859 coupling reaction Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 8
- 150000001336 alkenes Chemical group 0.000 description 8
- 210000003169 central nervous system Anatomy 0.000 description 8
- 208000015114 central nervous system disease Diseases 0.000 description 8
- 229960002715 nicotine Drugs 0.000 description 8
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 8
- ASEHPOZWQJRWAD-UHFFFAOYSA-N 3-bromo-5-propan-2-yloxypyridine Chemical class CC(C)OC1=CN=CC(Br)=C1 ASEHPOZWQJRWAD-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 5
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- FZWUIWQMJFAWJW-UHFFFAOYSA-N 3-bromo-5-methoxypyridine Chemical class COC1=CN=CC(Br)=C1 FZWUIWQMJFAWJW-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 210000002569 neuron Anatomy 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 150000003222 pyridines Chemical class 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 108010009685 Cholinergic Receptors Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 102000004108 Neurotransmitter Receptors Human genes 0.000 description 3
- 108090000590 Neurotransmitter Receptors Proteins 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 102000034337 acetylcholine receptors Human genes 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000006399 behavior Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000004064 dysfunction Effects 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- ZHZCYWWNFQUZOR-UHFFFAOYSA-N pent-4-en-2-ol Chemical compound CC(O)CC=C ZHZCYWWNFQUZOR-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000003386 piperidinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- MGFRWLSGAABYES-UHFFFAOYSA-N tert-butyl n-methyl-n-pent-4-en-2-ylcarbamate Chemical compound C=CCC(C)N(C)C(=O)OC(C)(C)C MGFRWLSGAABYES-UHFFFAOYSA-N 0.000 description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- RPCVIAXDAUMJJP-FNORWQNLSA-N (e)-n-methyl-5-(5-propan-2-yloxypyridin-3-yl)pent-4-en-2-amine Chemical compound CNC(C)C\C=C\C1=CN=CC(OC(C)C)=C1 RPCVIAXDAUMJJP-FNORWQNLSA-N 0.000 description 2
- YOQRXZIMSKLRCY-UHFFFAOYSA-N 5-bromonicotinamide Chemical compound NC(=O)C1=CN=CC(Br)=C1 YOQRXZIMSKLRCY-UHFFFAOYSA-N 0.000 description 2
- FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 238000007341 Heck reaction Methods 0.000 description 2
- 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 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000002393 azetidinyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- HXZJTUDXVFHWOB-GQCTYLIASA-N (e)-5-(5-methoxypyridin-3-yl)-n-methylpent-4-en-2-amine Chemical compound CNC(C)C\C=C\C1=CN=CC(OC)=C1 HXZJTUDXVFHWOB-GQCTYLIASA-N 0.000 description 1
- LWFLVOBZYLXRMP-UHFFFAOYSA-N 1,1,1-trifluoropent-4-en-2-ol Chemical compound FC(F)(F)C(O)CC=C LWFLVOBZYLXRMP-UHFFFAOYSA-N 0.000 description 1
- KLXJPQNHFFMLIG-UHFFFAOYSA-N 1-ethoxy-2,2,2-trifluoroethanol Chemical compound CCOC(O)C(F)(F)F KLXJPQNHFFMLIG-UHFFFAOYSA-N 0.000 description 1
- NVGOATMUHKIQQG-UHFFFAOYSA-N 2-Methyl-3-buten-1-ol Chemical compound OCC(C)C=C NVGOATMUHKIQQG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ZSPTYLOMNJNZNG-UHFFFAOYSA-N 3-Buten-1-ol Chemical compound OCCC=C ZSPTYLOMNJNZNG-UHFFFAOYSA-N 0.000 description 1
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- XDELKSRGBLWMBA-UHFFFAOYSA-N 3-iodopyridine Chemical compound IC1=CC=CN=C1 XDELKSRGBLWMBA-UHFFFAOYSA-N 0.000 description 1
- RKXRAFMFAMIVLI-UHFFFAOYSA-N 4-methylhex-5-en-2-ol Chemical compound CC(O)CC(C)C=C RKXRAFMFAMIVLI-UHFFFAOYSA-N 0.000 description 1
- LOFHPLKGPULNQP-UHFFFAOYSA-N 4-methylpent-4-en-1-ol Chemical compound CC(=C)CCCO LOFHPLKGPULNQP-UHFFFAOYSA-N 0.000 description 1
- KPHPTSMXBAVNPX-UHFFFAOYSA-N 4-methylpent-4-en-2-ol Chemical compound CC(O)CC(C)=C KPHPTSMXBAVNPX-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61P25/08—Antiepileptics; Anticonvulsants
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- 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
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- 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
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- 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
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Neurosurgery (AREA)
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- Biomedical Technology (AREA)
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- Psychology (AREA)
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- Psychiatry (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
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| US09/616,743 US6432954B1 (en) | 2000-07-14 | 2000-07-14 | Pharmaceutical compositions and methods for use |
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| ZA200300135B true ZA200300135B (en) | 2004-04-06 |
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| ZA200300135A ZA200300135B (en) | 2000-07-14 | 2003-01-06 | Pharmaceutical compositions for treating neurological disorders. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6432954B1 (fr) |
| EP (1) | EP1311265B1 (fr) |
| JP (1) | JP2004509851A (fr) |
| CN (2) | CN1680326A (fr) |
| AT (1) | ATE285773T1 (fr) |
| AU (2) | AU2290902A (fr) |
| BR (1) | BR0112130A (fr) |
| CA (1) | CA2415901A1 (fr) |
| DE (1) | DE60108130T2 (fr) |
| HU (1) | HUP0301553A3 (fr) |
| IL (3) | IL153577A0 (fr) |
| NO (1) | NO20030155L (fr) |
| NZ (1) | NZ523606A (fr) |
| PL (1) | PL360532A1 (fr) |
| WO (1) | WO2002005798A2 (fr) |
| ZA (1) | ZA200300135B (fr) |
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| US6979695B2 (en) * | 1996-04-23 | 2005-12-27 | Targacept, Inc. | Compounds capable of activating cholinergic receptors |
| EA200601839A1 (ru) * | 2004-04-21 | 2007-04-27 | Басф Акциенгезельшафт | Фунгицидные смеси |
| US7459469B2 (en) * | 2004-11-10 | 2008-12-02 | Targacept, Inc. | Hydroxybenzoate salts of metanicotine compounds |
| UA88792C2 (ru) * | 2004-11-10 | 2009-11-25 | Таргасепт, Інк. | Гидроксибензоатные соли метаникотиновых соединений |
| TWI389889B (zh) * | 2006-05-09 | 2013-03-21 | Targacept Inc | （２ｓ）-（４ｅ）-ｎ-甲基-５-〔３-（５-異丙氧基吡啶）基〕-４-戊烯-２-胺之新穎多晶型 |
| CN101528698A (zh) * | 2006-05-09 | 2009-09-09 | 阿斯利康公司 | (2s)-(4e)-n-甲基-5-[3-(5-异丙氧基吡啶)基]-4-戊烯-2-胺的盐形式 |
| CL2007002684A1 (es) * | 2006-09-15 | 2008-06-27 | Astrazeneca Ab Targacept Inc | Combinacion que comprende un antipsicotico y (2s)-(4e)-n-metil-5-[3-(5-isopropoxipiridin)il]-4-penten-2-amina; composicion farmaceutica que la comprende; kit farmaceutico; y uso para tratar perjuicio cognitivo y/o trastorno psicoticos. |
| EP2112923A1 (fr) * | 2007-01-22 | 2009-11-04 | Targacept Inc. | Administration intranasale, buccale ou sublinguale d'analogues de métanicotine |
| KR20100052490A (ko) * | 2007-07-31 | 2010-05-19 | 타가셉트 인코포레이티드 | (2ｓ)-(4ｅ)-ｎ-메틸-5-(3-(5-이소프로폭시피리딘)일)-4-펜텐-2-아민의 경피투여 |
| JP2013528601A (ja) | 2010-05-20 | 2013-07-11 | アストラゼネカ・アクチエボラーグ | アリール置換オレフィン系アミンの新規な製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1409551A (en) | 1972-04-14 | 1975-10-08 | Allen & Hanburys Ltd | Cyclopent a indene derivatives |
| US4528290A (en) | 1984-01-30 | 1985-07-09 | Eli Lilly And Company | Stimulating dopamine D-1 receptors |
| GB8606254D0 (en) | 1986-03-13 | 1986-04-16 | Wyeth John & Brother Ltd | Substituted pyrimidoindoles |
| FR2664600B1 (fr) | 1990-07-16 | 1994-09-02 | Rhone Poulenc Sante | Nouveau sel derive de la dialcoylaminoalcoyl-sulfonyl-26 pristinamycine iib. |
| US5278176A (en) * | 1992-08-21 | 1994-01-11 | Abbott Laboratories | Nicotine derivatives that enhance cognitive function |
| IL115305A0 (en) * | 1994-09-14 | 1995-12-31 | Lundbeck & Co As H | Carbamolyloxy amine compounds |
| US5597919A (en) * | 1995-01-06 | 1997-01-28 | Dull; Gary M. | Pyrimidinyl or Pyridinyl alkenyl amine compounds |
| US5616716A (en) * | 1996-01-06 | 1997-04-01 | Dull; Gary M. | (3-(5-ethoxypyridin)yl)-alkenyl 1 amine compounds |
| US5663356A (en) * | 1996-04-23 | 1997-09-02 | Ruecroft; Graham | Method for preparation of aryl substituted alefinic secondary amino compounds |
| JP3603177B2 (ja) * | 1998-03-26 | 2004-12-22 | 参天製薬株式会社 | 新規ウレア誘導体 |
| ES2150353B1 (es) * | 1998-04-15 | 2001-07-01 | Esteve Labor Dr | Tienilazolilalcoxietanaminas, su preparacion y su aplicacion como medicamentos. |
| ATE273956T1 (de) * | 1998-06-16 | 2004-09-15 | Targacept Inc | Arylsubstituierte olefinische amine und ihre verwendung als cholinergische rezeptoragonisten |
| DE10032456A1 (de) * | 2000-07-04 | 2002-01-31 | Lohmann Therapie Syst Lts | Schnell zerfallende Darreichungsform zur Freisetzung von Wirkstoffen im Mundraum oder in Körperhöhlen |
| US6743812B1 (en) * | 2000-07-14 | 2004-06-01 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
-
2000
- 2000-07-14 US US09/616,743 patent/US6432954B1/en not_active Expired - Fee Related
-
2001
- 2001-07-11 BR BR0112130-8A patent/BR0112130A/pt not_active Application Discontinuation
- 2001-07-11 AT AT01984212T patent/ATE285773T1/de not_active IP Right Cessation
- 2001-07-11 JP JP2002511731A patent/JP2004509851A/ja active Pending
- 2001-07-11 CN CNA2005100541592A patent/CN1680326A/zh active Pending
- 2001-07-11 AU AU2290902A patent/AU2290902A/xx active Pending
- 2001-07-11 DE DE60108130T patent/DE60108130T2/de not_active Expired - Fee Related
- 2001-07-11 WO PCT/US2001/021872 patent/WO2002005798A2/fr not_active Ceased
- 2001-07-11 NZ NZ523606A patent/NZ523606A/xx unknown
- 2001-07-11 PL PL01360532A patent/PL360532A1/xx not_active Application Discontinuation
- 2001-07-11 HU HU0301553A patent/HUP0301553A3/hu unknown
- 2001-07-11 AU AU2002222909A patent/AU2002222909B2/en not_active Ceased
- 2001-07-11 EP EP01984212A patent/EP1311265B1/fr not_active Expired - Lifetime
- 2001-07-11 IL IL15357701A patent/IL153577A0/xx unknown
- 2001-07-11 CA CA002415901A patent/CA2415901A1/fr not_active Abandoned
- 2001-07-11 CN CNA018127924A patent/CN1468100A/zh active Pending
-
2002
- 2002-12-22 IL IL153577A patent/IL153577A/en not_active IP Right Cessation
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2003
- 2003-01-06 ZA ZA200300135A patent/ZA200300135B/en unknown
- 2003-01-13 NO NO20030155A patent/NO20030155L/no not_active Application Discontinuation
-
2008
- 2008-06-18 IL IL192287A patent/IL192287A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20030155D0 (no) | 2003-01-13 |
| CN1680326A (zh) | 2005-10-12 |
| AU2002222909B2 (en) | 2005-12-15 |
| NO20030155L (no) | 2003-03-13 |
| NZ523606A (en) | 2004-12-24 |
| IL192287A0 (en) | 2008-12-29 |
| PL360532A1 (en) | 2004-09-06 |
| WO2002005798A3 (fr) | 2003-03-13 |
| HUP0301553A2 (hu) | 2003-08-28 |
| DE60108130T2 (de) | 2006-02-23 |
| DE60108130D1 (de) | 2005-02-03 |
| CN1468100A (zh) | 2004-01-14 |
| HUP0301553A3 (en) | 2005-05-30 |
| EP1311265B1 (fr) | 2004-12-29 |
| EP1311265A2 (fr) | 2003-05-21 |
| CA2415901A1 (fr) | 2002-01-24 |
| BR0112130A (pt) | 2003-09-02 |
| WO2002005798A2 (fr) | 2002-01-24 |
| IL153577A0 (en) | 2003-07-06 |
| ATE285773T1 (de) | 2005-01-15 |
| AU2290902A (en) | 2002-01-30 |
| US6432954B1 (en) | 2002-08-13 |
| JP2004509851A (ja) | 2004-04-02 |
| IL153577A (en) | 2009-07-20 |
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