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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Landscapes
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| WO2005102051A1 (de) * | 2004-04-21 | 2005-11-03 | Basf Aktiengesellschaft | Fungizide mischungen |
| 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 |
| 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 |
| 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 |
| TW200829244A (en) * | 2006-09-15 | 2008-07-16 | Astrazeneca Ab | Therapeutic combinations 482 |
| WO2008091592A1 (en) * | 2007-01-22 | 2008-07-31 | Targacept, Inc. | Intranasal, buccal, and sublingual administration of metanicotine analogs |
| KR20100052490A (ko) * | 2007-07-31 | 2010-05-19 | 타가셉트 인코포레이티드 | (2ｓ)-(4ｅ)-ｎ-메틸-5-(3-(5-이소프로폭시피리딘)일)-4-펜텐-2-아민의 경피투여 |
| CN103180277A (zh) | 2010-05-20 | 2013-06-26 | 塔格塞普特股份有限公司 | 制备芳基取代的烯属胺的新方法 |
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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. |
| PT1086082E (pt) * | 1998-06-16 | 2005-01-31 | Targacept Inc | Aminas olefinicas substituidas com arilo e seu uso como agonistas de receptores colinergicos |
| 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 |
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2001
- 2001-07-11 JP JP2002511731A patent/JP2004509851A/ja active Pending
- 2001-07-11 AU AU2002222909A patent/AU2002222909B2/en not_active Ceased
- 2001-07-11 IL IL15357701A patent/IL153577A0/xx unknown
- 2001-07-11 CN CNA018127924A patent/CN1468100A/zh active Pending
- 2001-07-11 BR BR0112130-8A patent/BR0112130A/pt not_active Application Discontinuation
- 2001-07-11 EP EP01984212A patent/EP1311265B1/en not_active Expired - Lifetime
- 2001-07-11 AU AU2290902A patent/AU2290902A/xx active Pending
- 2001-07-11 HU HU0301553A patent/HUP0301553A3/hu unknown
- 2001-07-11 AT AT01984212T patent/ATE285773T1/de not_active IP Right Cessation
- 2001-07-11 DE DE60108130T patent/DE60108130T2/de not_active Expired - Fee Related
- 2001-07-11 CN CNA2005100541592A patent/CN1680326A/zh active Pending
- 2001-07-11 PL PL01360532A patent/PL360532A1/xx not_active Application Discontinuation
- 2001-07-11 CA CA002415901A patent/CA2415901A1/en not_active Abandoned
- 2001-07-11 NZ NZ523606A patent/NZ523606A/xx unknown
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2002
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2003
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- 2003-01-13 NO NO20030155A patent/NO20030155L/no not_active Application Discontinuation
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2008
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|---|---|
| EP1311265B1 (en) | 2004-12-29 |
| AU2290902A (en) | 2002-01-30 |
| ATE285773T1 (de) | 2005-01-15 |
| AU2002222909B2 (en) | 2005-12-15 |
| PL360532A1 (en) | 2004-09-06 |
| BR0112130A (pt) | 2003-09-02 |
| US6432954B1 (en) | 2002-08-13 |
| JP2004509851A (ja) | 2004-04-02 |
| CA2415901A1 (en) | 2002-01-24 |
| DE60108130T2 (de) | 2006-02-23 |
| WO2002005798A2 (en) | 2002-01-24 |
| CN1468100A (zh) | 2004-01-14 |
| NO20030155L (no) | 2003-03-13 |
| IL153577A0 (en) | 2003-07-06 |
| HUP0301553A3 (en) | 2005-05-30 |
| CN1680326A (zh) | 2005-10-12 |
| NO20030155D0 (no) | 2003-01-13 |
| HUP0301553A2 (hu) | 2003-08-28 |
| WO2002005798A3 (en) | 2003-03-13 |
| IL192287A0 (en) | 2008-12-29 |
| EP1311265A2 (en) | 2003-05-21 |
| NZ523606A (en) | 2004-12-24 |
| DE60108130D1 (de) | 2005-02-03 |
| IL153577A (en) | 2009-07-20 |
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