AU2001261828A1 - Compositions containing diacyltartaric salts of (E)-metanicotine - Google Patents
Compositions containing diacyltartaric salts of (E)-metanicotineInfo
- Publication number
- AU2001261828A1 AU2001261828A1 AU2001261828A AU6182801A AU2001261828A1 AU 2001261828 A1 AU2001261828 A1 AU 2001261828A1 AU 2001261828 A AU2001261828 A AU 2001261828A AU 6182801 A AU6182801 A AU 6182801A AU 2001261828 A1 AU2001261828 A1 AU 2001261828A1
- Authority
- AU
- Australia
- Prior art keywords
- tartaric acid
- methyl
- amine
- compounds
- compound
- 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 title claims description 36
- 239000000203 mixture Substances 0.000 title claims description 35
- JUOSGGQXEBBCJB-GORDUTHDSA-N rivanicline Chemical class CNCC\C=C\C1=CC=CN=C1 JUOSGGQXEBBCJB-GORDUTHDSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 182
- 238000000034 method Methods 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims description 31
- 229960001270 d- tartaric acid Drugs 0.000 claims description 17
- 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 description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 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 description 7
- 230000003957 neurotransmitter release Effects 0.000 claims description 7
- 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 description 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 description 4
- 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 description 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 description 4
- SNZMBGPVGUVXRP-UHFFFAOYSA-N 4,5-dichloroquinoline Chemical compound C1=CC(Cl)=C2C(Cl)=CC=CC2=N1 SNZMBGPVGUVXRP-UHFFFAOYSA-N 0.000 claims description 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 description 4
- 230000004075 alteration Effects 0.000 claims description 4
- BKLZIAYVINRQEJ-UHFFFAOYSA-K trifluoroalumane;trihydrate Chemical compound O.O.O.F[Al](F)F BKLZIAYVINRQEJ-UHFFFAOYSA-K 0.000 claims description 4
- -1 nicotinic compounds Chemical class 0.000 description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 39
- 208000035475 disorder Diseases 0.000 description 38
- 125000001424 substituent group Chemical group 0.000 description 34
- 230000000694 effects Effects 0.000 description 33
- 238000005859 coupling reaction Methods 0.000 description 31
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 29
- 239000000126 substance Substances 0.000 description 28
- 239000002253 acid Substances 0.000 description 27
- 230000008878 coupling Effects 0.000 description 27
- 238000010168 coupling process Methods 0.000 description 27
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 26
- 239000001257 hydrogen Substances 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 22
- 208000015114 central nervous system disease Diseases 0.000 description 20
- 241000894007 species Species 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 18
- 210000003169 central nervous system Anatomy 0.000 description 18
- 238000007341 Heck reaction Methods 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 102000005962 receptors Human genes 0.000 description 17
- 108020003175 receptors Proteins 0.000 description 17
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 16
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 150000001336 alkenes Chemical group 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 229910052763 palladium Inorganic materials 0.000 description 14
- 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 14
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 13
- 230000002265 prevention Effects 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 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 12
- 125000003277 amino group Chemical group 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 208000024891 symptom Diseases 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 229960002715 nicotine Drugs 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 230000004913 activation Effects 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 9
- 125000000753 cycloalkyl group Chemical group 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 9
- ASEHPOZWQJRWAD-UHFFFAOYSA-N 3-bromo-5-propan-2-yloxypyridine Chemical class CC(C)OC1=CN=CC(Br)=C1 ASEHPOZWQJRWAD-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- 229960003638 dopamine Drugs 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 230000001225 therapeutic effect Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 239000000651 prodrug Substances 0.000 description 7
- 229940002612 prodrug Drugs 0.000 description 7
- 150000003222 pyridines Chemical class 0.000 description 7
- 230000028327 secretion Effects 0.000 description 7
- SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 6
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 6
- YRGMYJUKFJPNPD-UHFFFAOYSA-N 5-bromopyridine-2,3-diamine Chemical compound NC1=CC(Br)=CN=C1N YRGMYJUKFJPNPD-UHFFFAOYSA-N 0.000 description 6
- 208000024827 Alzheimer disease Diseases 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- 230000016396 cytokine production Effects 0.000 description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000002858 neurotransmitter agent Substances 0.000 description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 6
- ZUBFDFTWPBWMPD-UHFFFAOYSA-N tert-butyl n-methyl-n-(5-oxopentan-2-yl)carbamate Chemical compound O=CCCC(C)N(C)C(=O)OC(C)(C)C ZUBFDFTWPBWMPD-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 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 6
- NTOIKDYVJIWVSU-WOJBJXKFSA-N (2r,3r)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical group C1=CC(C)=CC=C1C(=O)[C@@](O)(C(O)=O)[C@](O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-WOJBJXKFSA-N 0.000 description 5
- KXBXUHWCODHRHK-UHFFFAOYSA-N 5-bromo-3-hydroxy-1h-pyridin-2-one Chemical compound OC1=CC(Br)=CNC1=O KXBXUHWCODHRHK-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 238000013459 approach Methods 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 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 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
- 238000010511 deprotection reaction Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000000547 substituted alkyl group Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 4
- FILVIKOEJGORQS-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C FILVIKOEJGORQS-UHFFFAOYSA-N 0.000 description 4
- IFMHNXABCSMTFF-UHFFFAOYSA-N 2,3-dihydrofuro[2,3-b]pyridine Chemical compound C1=CN=C2OCCC2=C1 IFMHNXABCSMTFF-UHFFFAOYSA-N 0.000 description 4
- KQSQZCCLUXPANQ-UHFFFAOYSA-N 2,3-dihydropyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2[N]CCC2=C1 KQSQZCCLUXPANQ-UHFFFAOYSA-N 0.000 description 4
- FZWUIWQMJFAWJW-UHFFFAOYSA-N 3-bromo-5-methoxypyridine Chemical class COC1=CN=CC(Br)=C1 FZWUIWQMJFAWJW-UHFFFAOYSA-N 0.000 description 4
- KTXDLMQWUZXRPA-UHFFFAOYSA-N 5-bromo-2-methylpyridin-3-ol Chemical compound CC1=NC=C(Br)C=C1O KTXDLMQWUZXRPA-UHFFFAOYSA-N 0.000 description 4
- AOLQXGYCKFKIPQ-UHFFFAOYSA-N 6-bromo-1,3-dihydroimidazo[4,5-b]pyridine-2-thione Chemical compound BrC1=CN=C2NC(=S)NC2=C1 AOLQXGYCKFKIPQ-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- LCKIPSGLXMCAOF-UHFFFAOYSA-N dibenzyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(O)C(O)C(=O)OCC1=CC=CC=C1 LCKIPSGLXMCAOF-UHFFFAOYSA-N 0.000 description 4
- 208000037765 diseases and disorders Diseases 0.000 description 4
- 238000006073 displacement reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N methylpyrazine Chemical compound CC1=CN=CC=N1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 4
- 230000004770 neurodegeneration Effects 0.000 description 4
- 208000015122 neurodegenerative disease Diseases 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- ZHZCYWWNFQUZOR-UHFFFAOYSA-N pent-4-en-2-ol Chemical compound CC(O)CC=C ZHZCYWWNFQUZOR-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000002244 precipitate Substances 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
- 230000002829 reductive effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 210000002027 skeletal muscle Anatomy 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZHZCYWWNFQUZOR-RXMQYKEDSA-N (2r)-pent-4-en-2-ol Chemical compound C[C@@H](O)CC=C ZHZCYWWNFQUZOR-RXMQYKEDSA-N 0.000 description 3
- 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 3
- YQADLKDQAXAIKW-UHFFFAOYSA-N 2-amino-5-bromopyridin-3-ol Chemical compound NC1=NC=C(Br)C=C1O YQADLKDQAXAIKW-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QOOCOFOGYRQPPN-UHFFFAOYSA-N 5-bromo-3-nitropyridin-2-amine Chemical compound NC1=NC=C(Br)C=C1[N+]([O-])=O QOOCOFOGYRQPPN-UHFFFAOYSA-N 0.000 description 3
- LUCOFXKHJMMXQZ-UHFFFAOYSA-N 6-bromo-[1,3]oxazolo[4,5-b]pyridine Chemical compound BrC1=CN=C2N=COC2=C1 LUCOFXKHJMMXQZ-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 102000009660 Cholinergic Receptors Human genes 0.000 description 3
- 108010009685 Cholinergic Receptors Proteins 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 102000004108 Neurotransmitter Receptors Human genes 0.000 description 3
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Classifications
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/465—Nicotine; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09616187 | 2000-07-14 | ||
| US09/616,187 US6743812B1 (en) | 2000-07-14 | 2000-07-14 | Pharmaceutical compositions and methods for use |
| PCT/US2001/040689 WO2002005801A2 (en) | 2000-07-14 | 2001-05-04 | Compositions containing diacyltartaric salts of (e)-metanicotine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001261828A1 true AU2001261828A1 (en) | 2002-01-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001261828A Abandoned AU2001261828A1 (en) | 2000-07-14 | 2001-05-04 | Compositions containing diacyltartaric salts of (E)-metanicotine |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6743812B1 (no) |
| EP (1) | EP1317267A2 (no) |
| JP (1) | JP2004503589A (no) |
| CN (1) | CN1452486A (no) |
| AU (1) | AU2001261828A1 (no) |
| BR (1) | BR0112131A (no) |
| CA (1) | CA2415906A1 (no) |
| HU (1) | HUP0301594A2 (no) |
| IL (1) | IL153487A0 (no) |
| NO (1) | NO20030156L (no) |
| PL (1) | PL365602A1 (no) |
| WO (1) | WO2002005801A2 (no) |
| ZA (1) | ZA200300132B (no) |
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| US6979695B2 (en) * | 1996-04-23 | 2005-12-27 | Targacept, Inc. | Compounds capable of activating cholinergic receptors |
| US6708064B2 (en) * | 2000-02-24 | 2004-03-16 | Ali R. Rezai | Modulation of the brain to affect psychiatric disorders |
| US6432954B1 (en) * | 2000-07-14 | 2002-08-13 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| 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 |
| EP2021325A2 (en) * | 2006-05-09 | 2009-02-11 | AstraZeneca AB | Salt forms of (2s)-(4e)-n-methyl-5-[3-(5-isopropoxypyridin)yl]-4-penten-2-amine |
| AR062860A1 (es) * | 2006-09-15 | 2008-12-10 | Astrazeneca Ab | Combinaciones terapeuticas 482 |
| US20100028447A1 (en) * | 2007-01-22 | 2010-02-04 | Targacept, Inc. | Intranasal, Buccal, And Sublingual Administration Of Metanicotine Analogs |
| AU2008282205A1 (en) * | 2007-07-31 | 2009-02-05 | Astrazeneca Ab | Transdermal administration of (2S)-(4E)-N-methyl-5-(3-( 5-isopropoxypyridin)yl)-4-penten-2-amine |
| EP2574188A4 (en) * | 2010-05-20 | 2015-09-02 | Targacept Inc | NOVEL PROCESS FOR THE PREPARATION OF ARYL SUBSTITUTED OLEFIN AMINES |
Family Cites Families (9)
| 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. |
| US5723477A (en) | 1994-11-10 | 1998-03-03 | Sibia Neurosciences, Inc. | Modulators of acetylcholine receptors |
| ES2377126T3 (es) * | 1994-12-12 | 2012-03-22 | Omeros Corporation | Solución de irrigación y utilización de la misma para la inhibición perioperatoria del dolor, la inflamación y/o los espasmos en una estructura vascular |
| EP0801527B1 (en) | 1995-01-06 | 2006-07-26 | Targacept, Inc. | Pharmaceutical compositions for prevention and treatment of central nervous system disorders |
| CA2197838C (en) * | 1996-03-01 | 2004-09-28 | Mark S. Miller | Mouthfeel and lubricity enhancing composition |
| US5663356A (en) | 1996-04-23 | 1997-09-02 | Ruecroft; Graham | Method for preparation of aryl substituted alefinic secondary amino compounds |
-
2000
- 2000-07-14 US US09/616,187 patent/US6743812B1/en not_active Expired - Fee Related
-
2001
- 2001-05-04 CN CN01812810A patent/CN1452486A/zh active Pending
- 2001-05-04 IL IL15348701A patent/IL153487A0/xx unknown
- 2001-05-04 AU AU2001261828A patent/AU2001261828A1/en not_active Abandoned
- 2001-05-04 WO PCT/US2001/040689 patent/WO2002005801A2/en not_active Ceased
- 2001-05-04 EP EP01935766A patent/EP1317267A2/en not_active Withdrawn
- 2001-05-04 PL PL01365602A patent/PL365602A1/xx unknown
- 2001-05-04 JP JP2002511734A patent/JP2004503589A/ja not_active Withdrawn
- 2001-05-04 HU HU0301594A patent/HUP0301594A2/hu unknown
- 2001-05-04 CA CA002415906A patent/CA2415906A1/en not_active Abandoned
- 2001-05-04 BR BR0112131-6A patent/BR0112131A/pt not_active Application Discontinuation
-
2003
- 2003-01-06 ZA ZA200300132A patent/ZA200300132B/en unknown
- 2003-01-13 NO NO20030156A patent/NO20030156L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL153487A0 (en) | 2003-07-06 |
| ZA200300132B (en) | 2004-04-06 |
| WO2002005801A2 (en) | 2002-01-24 |
| WO2002005801A3 (en) | 2002-08-08 |
| CN1452486A (zh) | 2003-10-29 |
| BR0112131A (pt) | 2003-09-02 |
| NO20030156L (no) | 2003-03-13 |
| CA2415906A1 (en) | 2002-01-24 |
| PL365602A1 (en) | 2005-01-10 |
| JP2004503589A (ja) | 2004-02-05 |
| EP1317267A2 (en) | 2003-06-11 |
| HUP0301594A2 (hu) | 2003-08-28 |
| NO20030156D0 (no) | 2003-01-13 |
| US6743812B1 (en) | 2004-06-01 |
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