NO315148B1 - Anvendelse av usubstituerte og substituerte N-(pyrrol-1-yl) pyridinaminer som antikonvulsive midler - Google Patents

Anvendelse av usubstituerte og substituerte N-(pyrrol-1-yl) pyridinaminer som antikonvulsive midler Download PDF

Info

Publication number: NO315148B1
Authority: NO; Norway
Prior art keywords: amine; pyridinyl; indol; methyl; oil
Prior art date: 1995-07-27

Application number

NO19980334A

Other languages

English (en)

Norwegian (no)

Other versions

NO980334D0 (no

NO980334L (no

Inventor

Francis P Huger

Sathapana Kongsamut

Craig Paul Smith

Lei Tang

Original Assignee

Aventis Pharma Inc

Priority date (The priority date 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 date listed.)

1995-07-27

Filing date

1998-01-26

Publication date

2003-07-21

1998-01-26 Application filed by Aventis Pharma Inc filed Critical Aventis Pharma Inc

1998-01-26 Publication of NO980334D0 publication Critical patent/NO980334D0/no

1998-03-26 Publication of NO980334L publication Critical patent/NO980334L/no

2003-07-21 Publication of NO315148B1 publication Critical patent/NO315148B1/no

Links

239000001961 anticonvulsive agent Substances 0.000 title description 10
229940125681 anticonvulsant agent Drugs 0.000 title description 3
YRDGLBYDACKRGP-UHFFFAOYSA-N n-pyrrol-1-ylpyridin-2-amine Chemical class C1=CC=CN1NC1=CC=CC=N1 YRDGLBYDACKRGP-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 101
229910052739 hydrogen Inorganic materials 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
YFXZWVUZIPQSKX-UHFFFAOYSA-N n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1NC1=CC=NC=C1 YFXZWVUZIPQSKX-UHFFFAOYSA-N 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
JZJOYDMEYCKSER-UHFFFAOYSA-N n-pyrrol-1-ylpyridin-4-amine Chemical compound C1=CC=CN1NC1=CC=NC=C1 JZJOYDMEYCKSER-UHFFFAOYSA-N 0.000 claims description 10
206010010904 Convulsion Diseases 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
TWBAZCSQSDRRLC-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-3-methylindol-1-amine Chemical compound C12=CC=CC=C2C(C)=CN1NC1=CC=NC=C1F TWBAZCSQSDRRLC-UHFFFAOYSA-N 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
UDBVCOUCZYQHIC-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)-3-methylindol-1-amine Chemical compound C12=CC=CC=C2C(C)=CN1NC1=CC=NC=C1Cl UDBVCOUCZYQHIC-UHFFFAOYSA-N 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
WHLDTCCEOJXGLT-UHFFFAOYSA-N 3-ethyl-n-methyl-n-pyridin-4-ylindol-1-amine Chemical compound C12=CC=CC=C2C(CC)=CN1N(C)C1=CC=NC=C1 WHLDTCCEOJXGLT-UHFFFAOYSA-N 0.000 claims description 4
CGFBQVYTBDDHBS-UHFFFAOYSA-N 5-bromo-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(Br)=CC=C2N1NC1=CC=NC=C1 CGFBQVYTBDDHBS-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
229910052731 fluorine Chemical group 0.000 claims description 4
239000011737 fluorine Chemical group 0.000 claims description 4
VXWBEPWNOLUBNS-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-2-methylindol-1-amine Chemical compound CC1=CC2=CC=CC=C2N1NC1=CC=NC=C1F VXWBEPWNOLUBNS-UHFFFAOYSA-N 0.000 claims description 4
FNGZDYCLVVUVNF-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)indol-1-amine Chemical compound FC1=CN=CC=C1NN1C2=CC=CC=C2C=C1 FNGZDYCLVVUVNF-UHFFFAOYSA-N 0.000 claims description 4
SPGFFOXASUPGGC-UHFFFAOYSA-N 2-methyl-n-pyridin-4-ylindol-1-amine Chemical compound CC1=CC2=CC=CC=C2N1NC1=CC=NC=C1 SPGFFOXASUPGGC-UHFFFAOYSA-N 0.000 claims description 3
BQXVTDPDTMKXAH-UHFFFAOYSA-N 3-chloro-n-pyridin-4-ylindol-1-amine Chemical compound C12=CC=CC=C2C(Cl)=CN1NC1=CC=NC=C1 BQXVTDPDTMKXAH-UHFFFAOYSA-N 0.000 claims description 3
VUAIXYZNGSCECU-UHFFFAOYSA-N 3-methyl-1-(pyridin-4-ylamino)indol-5-ol Chemical compound C12=CC=C(O)C=C2C(C)=CN1NC1=CC=NC=C1 VUAIXYZNGSCECU-UHFFFAOYSA-N 0.000 claims description 3
FOWTXXOWJKWIGY-UHFFFAOYSA-N 3-methyl-n-pyridin-4-ylindol-1-amine Chemical compound C12=CC=CC=C2C(C)=CN1NC1=CC=NC=C1 FOWTXXOWJKWIGY-UHFFFAOYSA-N 0.000 claims description 3
NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 3
SDCIJOLMGUGDKZ-UHFFFAOYSA-N 5-chloro-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(Cl)=CC=C2N1NC1=CC=NC=C1 SDCIJOLMGUGDKZ-UHFFFAOYSA-N 0.000 claims description 3
OTPPJICEBWOCKD-UHFFFAOYSA-N besipirdine Chemical compound C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 OTPPJICEBWOCKD-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
YAPFXHKGCQHAKP-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)indol-1-amine Chemical compound ClC1=CN=CC=C1NN1C2=CC=CC=C2C=C1 YAPFXHKGCQHAKP-UHFFFAOYSA-N 0.000 claims description 3
FAZLTNYKLXWNRM-UHFFFAOYSA-N n-(3-methylpyridin-4-yl)indol-1-amine Chemical compound CC1=CN=CC=C1NN1C2=CC=CC=C2C=C1 FAZLTNYKLXWNRM-UHFFFAOYSA-N 0.000 claims description 3
RBKZPZVPVZNIMS-UHFFFAOYSA-N n-ethyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(CC)C1=CC=NC=C1 RBKZPZVPVZNIMS-UHFFFAOYSA-N 0.000 claims description 3
DNJVUBHSRZPIGX-UHFFFAOYSA-N n-ethyl-n-pyrrol-1-ylpyridin-4-amine Chemical compound C1=CC=CN1N(CC)C1=CC=NC=C1 DNJVUBHSRZPIGX-UHFFFAOYSA-N 0.000 claims description 3
DZLHSFJMKLMKMN-UHFFFAOYSA-N n-methyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(C)C1=CC=NC=C1 DZLHSFJMKLMKMN-UHFFFAOYSA-N 0.000 claims description 3
RMMHGSOMPGRWLZ-UHFFFAOYSA-N n-methyl-n-pyrrol-1-ylpyridin-4-amine Chemical compound C1=CC=CN1N(C)C1=CC=NC=C1 RMMHGSOMPGRWLZ-UHFFFAOYSA-N 0.000 claims description 3
GXSYMWSGWUUGCO-UHFFFAOYSA-N n-propyl-n-pyrrol-1-ylpyridin-4-amine Chemical compound C1=CC=CN1N(CCC)C1=CC=NC=C1 GXSYMWSGWUUGCO-UHFFFAOYSA-N 0.000 claims description 3
JULKLMOOTJHVHH-UHFFFAOYSA-N n-pyridin-2-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1NC1=CC=CC=N1 JULKLMOOTJHVHH-UHFFFAOYSA-N 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
WHQULUBXRZWECQ-UHFFFAOYSA-N 1-[3-(3-fluoropyridin-4-yl)propylamino]-3-methylindol-5-ol Chemical compound C12=CC=C(O)C=C2C(C)=CN1NCCCC1=CC=NC=C1F WHQULUBXRZWECQ-UHFFFAOYSA-N 0.000 claims description 2
OBEVLJZWTSVBGU-UHFFFAOYSA-N 2-butyl-n-methyl-n-pyrrol-1-ylpyridin-4-amine Chemical compound C1=NC(CCCC)=CC(N(C)N2C=CC=C2)=C1 OBEVLJZWTSVBGU-UHFFFAOYSA-N 0.000 claims description 2
JCEBKNUYKMFQGZ-UHFFFAOYSA-N 2-methyl-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound CC1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 JCEBKNUYKMFQGZ-UHFFFAOYSA-N 0.000 claims description 2
WYYMJBKATZOXQY-UHFFFAOYSA-N 3-(2-aminoethyl)-n-pyridin-4-ylindol-1-amine Chemical compound C12=CC=CC=C2C(CCN)=CN1NC1=CC=NC=C1 WYYMJBKATZOXQY-UHFFFAOYSA-N 0.000 claims description 2
RKBBHDYDBRVFMG-UHFFFAOYSA-N 3-(aminomethyl)-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=C(CN)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 RKBBHDYDBRVFMG-UHFFFAOYSA-N 0.000 claims description 2
ZJNNOQNHJJUAEO-UHFFFAOYSA-N 3-chloro-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=C(Cl)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 ZJNNOQNHJJUAEO-UHFFFAOYSA-N 0.000 claims description 2
KHGNFQVPPCBUSI-UHFFFAOYSA-N 3-ethyl-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=C(CC)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 KHGNFQVPPCBUSI-UHFFFAOYSA-N 0.000 claims description 2
IHMSBOIANJQTTO-UHFFFAOYSA-N 3-methyl-1-[propyl(pyridin-4-yl)amino]indol-5-ol Chemical compound C1=C(C)C2=CC(O)=CC=C2N1N(CCC)C1=CC=NC=C1 IHMSBOIANJQTTO-UHFFFAOYSA-N 0.000 claims description 2
JFXXREWKFGYUCE-UHFFFAOYSA-N 3-methyl-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=C(C)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 JFXXREWKFGYUCE-UHFFFAOYSA-N 0.000 claims description 2
ZGKKKWMQYVOFGE-UHFFFAOYSA-N 5-bromo-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(Br)=CC=C2N1N(CCC)C1=CC=NC=C1 ZGKKKWMQYVOFGE-UHFFFAOYSA-N 0.000 claims description 2
HQWVGYBVUZNQFB-UHFFFAOYSA-N 5-chloro-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(Cl)=CC=C2N1N(CCC)C1=CC=NC=C1 HQWVGYBVUZNQFB-UHFFFAOYSA-N 0.000 claims description 2
SYFFAEMYTWTOCA-UHFFFAOYSA-N 5-methoxy-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(OC)=CC=C2N1N(CCC)C1=CC=NC=C1 SYFFAEMYTWTOCA-UHFFFAOYSA-N 0.000 claims description 2
230000036461 convulsion Effects 0.000 claims description 2
OMOXURHGZXYWKA-UHFFFAOYSA-N n-(2,5-dimethylpyrrol-1-yl)-n-propylpyridin-4-amine Chemical compound CC1=CC=C(C)N1N(CCC)C1=CC=NC=C1 OMOXURHGZXYWKA-UHFFFAOYSA-N 0.000 claims description 2
PWGPOXYWHCBNEA-UHFFFAOYSA-N n-(2-chloropyrrol-1-yl)-n-ethylpyridin-4-amine Chemical compound C1=CC=C(Cl)N1N(CC)C1=CC=NC=C1 PWGPOXYWHCBNEA-UHFFFAOYSA-N 0.000 claims description 2
XQAFBPMRMMAVOI-UHFFFAOYSA-N n-(2-chloropyrrol-1-yl)-n-methylpyridin-4-amine Chemical compound C1=CC=C(Cl)N1N(C)C1=CC=NC=C1 XQAFBPMRMMAVOI-UHFFFAOYSA-N 0.000 claims description 2
DXUBLNCNQLMUAY-UHFFFAOYSA-N n-(2-chloropyrrol-1-yl)-n-propylpyridin-4-amine Chemical compound C1=CC=C(Cl)N1N(CCC)C1=CC=NC=C1 DXUBLNCNQLMUAY-UHFFFAOYSA-N 0.000 claims description 2
KCMCMBUSJHQMIC-UHFFFAOYSA-N n-(2-chloropyrrol-1-yl)pyridin-4-amine Chemical compound ClC1=CC=CN1NC1=CC=NC=C1 KCMCMBUSJHQMIC-UHFFFAOYSA-N 0.000 claims description 2
VXBJSLRTKRFLOW-UHFFFAOYSA-N n-(2-ethylpyrrol-1-yl)-n-methylpyridin-4-amine Chemical compound CCC1=CC=CN1N(C)C1=CC=NC=C1 VXBJSLRTKRFLOW-UHFFFAOYSA-N 0.000 claims description 2
KXAYGOMOYDYKSW-UHFFFAOYSA-N n-(2-methylpropyl)-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(CC(C)C)C1=CC=NC=C1 KXAYGOMOYDYKSW-UHFFFAOYSA-N 0.000 claims description 2
KMZICUNNVJIFRO-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)-3-methyl-n-propylindol-1-amine Chemical compound C1=C(C)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1Cl KMZICUNNVJIFRO-UHFFFAOYSA-N 0.000 claims description 2
CRQBEOJAVWRQAL-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-2-methyl-n-propylindol-1-amine Chemical compound CC1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1F CRQBEOJAVWRQAL-UHFFFAOYSA-N 0.000 claims description 2
BTDHTARYCBHHPJ-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-3-methyl-n-propylindol-1-amine Chemical compound C1=C(C)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1F BTDHTARYCBHHPJ-UHFFFAOYSA-N 0.000 claims description 2
LCTFOVSKAWGAQG-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-n-propylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1F LCTFOVSKAWGAQG-UHFFFAOYSA-N 0.000 claims description 2
BSTRWKXBERXYLR-UHFFFAOYSA-N n-(3-methylpyridin-4-yl)-n-propylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1C BSTRWKXBERXYLR-UHFFFAOYSA-N 0.000 claims description 2
ZUFXSGOKMZHLOL-UHFFFAOYSA-N n-butan-2-yl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(C(C)CC)C1=CC=NC=C1 ZUFXSGOKMZHLOL-UHFFFAOYSA-N 0.000 claims description 2
OSRPQIAWURAKDF-UHFFFAOYSA-N n-butyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(CCCC)C1=CC=NC=C1 OSRPQIAWURAKDF-UHFFFAOYSA-N 0.000 claims description 2
DWQZFWPOZIFTRB-UHFFFAOYSA-N n-butyl-n-pyrrol-1-ylpyridin-4-amine Chemical compound C1=CC=CN1N(CCCC)C1=CC=NC=C1 DWQZFWPOZIFTRB-UHFFFAOYSA-N 0.000 claims description 2
INRFJMBDDNXNPN-UHFFFAOYSA-N n-methyl-n-(2-propylpyrrol-1-yl)pyridin-4-amine Chemical compound CCCC1=CC=CN1N(C)C1=CC=NC=C1 INRFJMBDDNXNPN-UHFFFAOYSA-N 0.000 claims description 2
MMXQNINXIMLVLL-UHFFFAOYSA-N n-pentyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(CCCCC)C1=CC=NC=C1 MMXQNINXIMLVLL-UHFFFAOYSA-N 0.000 claims description 2
LWXMYCZRAJRIND-UHFFFAOYSA-N n-propan-2-yl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(C(C)C)C1=CC=NC=C1 LWXMYCZRAJRIND-UHFFFAOYSA-N 0.000 claims description 2
DBMDAMTYQAYQIS-UHFFFAOYSA-N n-pyridin-3-ylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1NC1=CC=CN=C1 DBMDAMTYQAYQIS-UHFFFAOYSA-N 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 210
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 195
239000003921 oil Substances 0.000 description 170
239000000243 solution Substances 0.000 description 114
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 108
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 106
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 98
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
238000004458 analytical method Methods 0.000 description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 43
239000000377 silicon dioxide Substances 0.000 description 42
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 41
239000012312 sodium hydride Substances 0.000 description 41
229910000104 sodium hydride Inorganic materials 0.000 description 41
239000013078 crystal Substances 0.000 description 36
239000000203 mixture Substances 0.000 description 35
239000011541 reaction mixture Substances 0.000 description 34
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 33
239000007787 solid Substances 0.000 description 33
239000000284 extract Substances 0.000 description 32
239000000725 suspension Substances 0.000 description 31
238000003818 flash chromatography Methods 0.000 description 30
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
238000004128 high performance liquid chromatography Methods 0.000 description 23
230000015572 biosynthetic process Effects 0.000 description 21
239000005457 ice water Substances 0.000 description 21
238000003756 stirring Methods 0.000 description 21
239000000047 product Substances 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000000463 material Substances 0.000 description 18
-1 methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy Chemical group 0.000 description 18
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
150000002688 maleic acid derivatives Chemical class 0.000 description 16
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 15
150000001450 anions Chemical class 0.000 description 14
239000011343 solid material Substances 0.000 description 14
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 12
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012267 brine Substances 0.000 description 12
229910000029 sodium carbonate Inorganic materials 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
238000012360 testing method Methods 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
230000027455 binding Effects 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000003814 drug Substances 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
HTXWKZDRDRFVHN-UHFFFAOYSA-N 2-methyloxiran-2-ol Chemical compound CC1(O)CO1 HTXWKZDRDRFVHN-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 7
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 7
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
239000004533 oil dispersion Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
VUSYGSNEEYEGGX-UHFFFAOYSA-N indol-1-amine Chemical compound C1=CC=C2N(N)C=CC2=C1 VUSYGSNEEYEGGX-UHFFFAOYSA-N 0.000 description 6
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
108010052164 Sodium Channels Proteins 0.000 description 5
102000018674 Sodium Channels Human genes 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
230000001773 anti-convulsant effect Effects 0.000 description 5
229960003965 antiepileptics Drugs 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000012528 membrane Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 5
239000003826 tablet Substances 0.000 description 5
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
239000007995 HEPES buffer Substances 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
239000002480 mineral oil Substances 0.000 description 4
235000010446 mineral oil Nutrition 0.000 description 4
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 4
YNZAFFFENDLJQG-UHFFFAOYSA-N pyrrol-1-amine Chemical compound NN1C=CC=C1 YNZAFFFENDLJQG-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
YWWXNVPPEXEZPT-UHFFFAOYSA-N 4-chloro-3-fluoropyridine;hydrochloride Chemical compound Cl.FC1=CN=CC=C1Cl YWWXNVPPEXEZPT-UHFFFAOYSA-N 0.000 description 3
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
210000000548 hind-foot Anatomy 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
238000000746 purification Methods 0.000 description 3
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
CSRFMFBFJAUJDS-UHFFFAOYSA-N 2-[1-(pyridin-4-ylamino)indol-3-yl]acetonitrile Chemical compound C12=CC=CC=C2C(CC#N)=CN1NC1=CC=NC=C1 CSRFMFBFJAUJDS-UHFFFAOYSA-N 0.000 description 2
239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
ZVEGQLNQUKGLNF-UHFFFAOYSA-N 2-methylindol-1-amine Chemical compound C1=CC=C2N(N)C(C)=CC2=C1 ZVEGQLNQUKGLNF-UHFFFAOYSA-N 0.000 description 2
WHSTXSORAFCZBI-UHFFFAOYSA-N 3,4-dichloropyridine;hydrochloride Chemical compound Cl.ClC1=CC=NC=C1Cl WHSTXSORAFCZBI-UHFFFAOYSA-N 0.000 description 2
PPIMNKBXUAJCTQ-UHFFFAOYSA-N 3-methylindol-1-amine Chemical compound C1=CC=C2C(C)=CN(N)C2=C1 PPIMNKBXUAJCTQ-UHFFFAOYSA-N 0.000 description 2
WPIUSHWGBZMBHZ-UHFFFAOYSA-N 4-chloro-3-methylpyridin-1-ium;chloride Chemical compound Cl.CC1=CN=CC=C1Cl WPIUSHWGBZMBHZ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
ISNYUQWBWALXEY-UHFFFAOYSA-N Batrachotoxin Natural products C=1CC2(C3=CCC4C5(C)CCC(C4)(O)OC53C(O)C3)OCCN(C)CC32C=1C(C)OC(=O)C=1C(C)=CNC=1C ISNYUQWBWALXEY-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
235000019743 Choline chloride Nutrition 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 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
206010043994 Tonic convulsion Diseases 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 2
229960000623 carbamazepine Drugs 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
229960003178 choline chloride Drugs 0.000 description 2
230000009918 complex formation Effects 0.000 description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000010685 fatty oil Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229960002036 phenytoin Drugs 0.000 description 2
239000006187 pill Substances 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
208000028500 tonic seizure Diseases 0.000 description 2
ISNYUQWBWALXEY-OMIQOYQYSA-N tsg6xhx09r Chemical compound O([C@@H](C)C=1[C@@]23CN(C)CCO[C@]3(C3=CC[C@H]4[C@]5(C)CC[C@@](C4)(O)O[C@@]53[C@H](O)C2)CC=1)C(=O)C=1C(C)=CNC=1C ISNYUQWBWALXEY-OMIQOYQYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
102000008538 voltage-gated sodium channel activity proteins Human genes 0.000 description 2
108040002416 voltage-gated sodium channel activity proteins Proteins 0.000 description 2
YOKMPPGEVSKETG-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-ethenyl-n-methyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=C(C=C)C2=CC=CC=C2N1N(C)C1=CC=NC=C1 YOKMPPGEVSKETG-BTJKTKAUSA-N 0.000 description 1
NCSRVJSLFYUNMO-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-ethenyl-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=C(C=C)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 NCSRVJSLFYUNMO-BTJKTKAUSA-N 0.000 description 1
HPZMPUCTSBQCQD-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-ethyl-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=C(CC)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 HPZMPUCTSBQCQD-BTJKTKAUSA-N 0.000 description 1
VOFYUOXJFNBVTL-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-methyl-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=C(C)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 VOFYUOXJFNBVTL-BTJKTKAUSA-N 0.000 description 1
NFWJHYPJGRFZNW-BTJKTKAUSA-N (z)-but-2-enedioic acid;5-chloro-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC(Cl)=CC=C2N1NC1=CC=NC=C1 NFWJHYPJGRFZNW-BTJKTKAUSA-N 0.000 description 1
POKMMZFAKIOEQV-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-(2,5-dimethylpyrrol-1-yl)-n-propylpyridin-4-amine Chemical compound OC(=O)\C=C/C(O)=O.CC1=CC=C(C)N1N(CCC)C1=CC=NC=C1 POKMMZFAKIOEQV-BTJKTKAUSA-N 0.000 description 1
RNBPVGRXVUWVGL-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-(2-methylpropyl)-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC=CC=C2N1N(CC(C)C)C1=CC=NC=C1 RNBPVGRXVUWVGL-BTJKTKAUSA-N 0.000 description 1
XDNGYJKUKBJQKN-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-butyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC=CC=C2N1N(CCCC)C1=CC=NC=C1 XDNGYJKUKBJQKN-BTJKTKAUSA-N 0.000 description 1
NMNIOYNAYXTWBU-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-methyl-5-nitro-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC([N+]([O-])=O)=CC=C2N1N(C)C1=CC=NC=C1 NMNIOYNAYXTWBU-BTJKTKAUSA-N 0.000 description 1
FTOXLHHMYLTADY-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-methyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC=CC=C2N1N(C)C1=CC=NC=C1 FTOXLHHMYLTADY-BTJKTKAUSA-N 0.000 description 1
BWZPKTGIFVBVJK-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-prop-2-ynyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC=CC=C2N1N(CC#C)C1=CC=NC=C1 BWZPKTGIFVBVJK-BTJKTKAUSA-N 0.000 description 1
KKPNPFIUMDXTTA-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 KKPNPFIUMDXTTA-BTJKTKAUSA-N 0.000 description 1
SGEGAKQXNTUUEZ-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-pyridin-4-ylindol-1-amine Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC=CC=C2N1NC1=CC=NC=C1 SGEGAKQXNTUUEZ-BTJKTKAUSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
ILLCAHRQXHPAIO-UHFFFAOYSA-N 1-pyrrol-1-yl-2h-pyridine Chemical compound C1C=CC=CN1N1C=CC=C1 ILLCAHRQXHPAIO-UHFFFAOYSA-N 0.000 description 1
HHABYUFFGOEFCF-UHFFFAOYSA-N 2-(1-aminoindol-3-yl)acetonitrile Chemical compound C1=CC=C2N(N)C=C(CC#N)C2=C1 HHABYUFFGOEFCF-UHFFFAOYSA-N 0.000 description 1
MDZKNBJIJHKPCL-UHFFFAOYSA-N 2-(5-chloropyridin-3-yl)indol-1-amine Chemical compound C=1C2=CC=CC=C2N(N)C=1C1=CN=CC(Cl)=C1 MDZKNBJIJHKPCL-UHFFFAOYSA-N 0.000 description 1
UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
MTAODLNXWYIKSO-UHFFFAOYSA-N 2-fluoropyridine Chemical compound FC1=CC=CC=N1 MTAODLNXWYIKSO-UHFFFAOYSA-N 0.000 description 1
WPGHPGAUFIJVJF-UHFFFAOYSA-N 3,5-dichloropyridine Chemical compound ClC1=CN=CC(Cl)=C1 WPGHPGAUFIJVJF-UHFFFAOYSA-N 0.000 description 1
SBNRHDKLCJMEHT-UHFFFAOYSA-N 3-chloro-n-pyridin-4-ylindol-1-amine;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.C12=CC=CC=C2C(Cl)=CN1NC1=CC=NC=C1 SBNRHDKLCJMEHT-UHFFFAOYSA-N 0.000 description 1
PQAJXVYSNSPYIQ-UHFFFAOYSA-N 3-chloroindol-1-amine Chemical compound C1=CC=C2N(N)C=C(Cl)C2=C1 PQAJXVYSNSPYIQ-UHFFFAOYSA-N 0.000 description 1
HGWXHWZVMGVFDH-UHFFFAOYSA-N 3-ethenyl-n-methyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=C(C=C)C2=CC=CC=C2N1N(C)C1=CC=NC=C1 HGWXHWZVMGVFDH-UHFFFAOYSA-N 0.000 description 1
DQHQVPADTYDJMD-UHFFFAOYSA-N 3-ethenyl-n-propyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=C(C=C)C2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 DQHQVPADTYDJMD-UHFFFAOYSA-N 0.000 description 1
HPNBACQUNBIKKZ-UHFFFAOYSA-N 3-fluoro-n-propyl-n-pyrrol-1-ylpyridin-4-amine Chemical compound C1=CC=CN1N(CCC)C1=CC=NC=C1F HPNBACQUNBIKKZ-UHFFFAOYSA-N 0.000 description 1
ITPBOYVJMDECCC-UHFFFAOYSA-N 3-methyl-1h-indol-2-amine Chemical compound C1=CC=C2C(C)=C(N)NC2=C1 ITPBOYVJMDECCC-UHFFFAOYSA-N 0.000 description 1
VSUPPNDBPIRTCH-UHFFFAOYSA-N 3-methyl-5-phenylmethoxy-n-pyridin-4-ylindol-1-amine Chemical compound C12=CC=C(OCC=3C=CC=CC=3)C=C2C(C)=CN1NC1=CC=NC=C1 VSUPPNDBPIRTCH-UHFFFAOYSA-N 0.000 description 1
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 1
PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 1
LCPXLRHRFOEFHQ-UHFFFAOYSA-N 5-bromo-n-methyl-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(Br)=CC=C2N1N(C)C1=CC=NC=C1 LCPXLRHRFOEFHQ-UHFFFAOYSA-N 0.000 description 1
MDICBCOGEZPNFS-BTJKTKAUSA-N 5-bromo-n-methyl-n-pyridin-4-ylindol-1-amine;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC(Br)=CC=C2N1N(C)C1=CC=NC=C1 MDICBCOGEZPNFS-BTJKTKAUSA-N 0.000 description 1
HWSAGWOPFNSJID-BTJKTKAUSA-N 5-bromo-n-propyl-n-pyridin-4-ylindol-1-amine;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC(Br)=CC=C2N1N(CCC)C1=CC=NC=C1 HWSAGWOPFNSJID-BTJKTKAUSA-N 0.000 description 1
XHRXLBKYSOGTAP-BTJKTKAUSA-N 5-bromo-n-pyridin-4-ylindol-1-amine;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC(Br)=CC=C2N1NC1=CC=NC=C1 XHRXLBKYSOGTAP-BTJKTKAUSA-N 0.000 description 1
JOHVESYHIQQIFE-UHFFFAOYSA-N 5-bromoindol-1-amine Chemical compound BrC1=CC=C2N(N)C=CC2=C1 JOHVESYHIQQIFE-UHFFFAOYSA-N 0.000 description 1
RAQJUUBNJUGZGQ-UHFFFAOYSA-N 5-chloroindol-1-amine Chemical compound ClC1=CC=C2N(N)C=CC2=C1 RAQJUUBNJUGZGQ-UHFFFAOYSA-N 0.000 description 1
OLLIUPXULGNHBZ-UHFFFAOYSA-N 5-methoxy-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC(OC)=CC=C2N1NC1=CC=NC=C1 OLLIUPXULGNHBZ-UHFFFAOYSA-N 0.000 description 1
LKXCLZURUSBJKI-UHFFFAOYSA-N 5-nitro-n-pyridin-4-ylindol-1-amine Chemical compound C1=CC2=CC([N+](=O)[O-])=CC=C2N1NC1=CC=NC=C1 LKXCLZURUSBJKI-UHFFFAOYSA-N 0.000 description 1
SBZACGHWWDTLKD-UHFFFAOYSA-N 5-nitroindol-1-amine Chemical compound [O-][N+](=O)C1=CC=C2N(N)C=CC2=C1 SBZACGHWWDTLKD-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
229910000838 Al alloy Inorganic materials 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
102000013138 Drug Receptors Human genes 0.000 description 1
108010065556 Drug Receptors Proteins 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000034308 Grand mal convulsion Diseases 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229910000990 Ni alloy Inorganic materials 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
241000124033 Salix Species 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000032683 aging Effects 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 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
239000011230 binding agent Substances 0.000 description 1
235000015895 biscuits Nutrition 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000001713 cholinergic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000003179 convulsant agent Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000007405 data analysis Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
CHVWXAHWVABFQG-UHFFFAOYSA-N ethyl carbamate;hydrochloride Chemical compound Cl.CCOC(N)=O CHVWXAHWVABFQG-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
BWDFMLLTDVVBBA-UHFFFAOYSA-N ethyl n-pyridin-4-yl-n-pyrrol-1-ylcarbamate Chemical compound C1=CC=CN1N(C(=O)OCC)C1=CC=NC=C1 BWDFMLLTDVVBBA-UHFFFAOYSA-N 0.000 description 1
230000005284 excitation Effects 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
230000036541 health Effects 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
235000001050 hortel pimenta Nutrition 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 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
239000008101 lactose Substances 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000007074 memory dysfunction Effects 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
229960001047 methyl salicylate Drugs 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
REAXHZMYNDHUPJ-UHFFFAOYSA-N n-(2,5-dimethylpyrrol-1-yl)pyridin-4-amine Chemical compound CC1=CC=C(C)N1NC1=CC=NC=C1 REAXHZMYNDHUPJ-UHFFFAOYSA-N 0.000 description 1
PXHGLPNDFSHSHG-UHFFFAOYSA-N n-(2-chloropyrrol-1-yl)-n-methylpyridin-4-amine;hydrochloride Chemical compound Cl.C1=CC=C(Cl)N1N(C)C1=CC=NC=C1 PXHGLPNDFSHSHG-UHFFFAOYSA-N 0.000 description 1
IRNMNKGPLPIDNV-UHFFFAOYSA-N n-(2-chloropyrrol-1-yl)pyridin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC=CN1NC1=CC=NC=C1 IRNMNKGPLPIDNV-UHFFFAOYSA-N 0.000 description 1
PMRGRIKEHLCIFM-UHFFFAOYSA-N n-(2-ethenylpyrrol-1-yl)-n-methylpyridin-4-amine Chemical compound C1=CC=C(C=C)N1N(C)C1=CC=NC=C1 PMRGRIKEHLCIFM-UHFFFAOYSA-N 0.000 description 1
UHVWQGJGJHCPTJ-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)-3-methylindol-1-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(C)=CN1NC1=CC=NC=C1Cl UHVWQGJGJHCPTJ-UHFFFAOYSA-N 0.000 description 1
HSKDGAPCBQCVBH-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)-n-propylindol-1-amine Chemical compound C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1Cl HSKDGAPCBQCVBH-UHFFFAOYSA-N 0.000 description 1
YEOYISBNNCVIMR-UHFFFAOYSA-N n-(3-chloropyridin-4-yl)indol-1-amine;hydrochloride Chemical compound Cl.ClC1=CN=CC=C1NN1C2=CC=CC=C2C=C1 YEOYISBNNCVIMR-UHFFFAOYSA-N 0.000 description 1
AJXYLZARPVUQPY-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-3-methyl-n-prop-2-ynylindol-1-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(C)=CN1N(CC#C)C1=CC=NC=C1F AJXYLZARPVUQPY-UHFFFAOYSA-N 0.000 description 1
PZISXCKVPRNSQZ-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-n-prop-2-ynylindol-1-amine;hydrochloride Chemical compound Cl.FC1=CN=CC=C1N(CC#C)N1C2=CC=CC=C2C=C1 PZISXCKVPRNSQZ-UHFFFAOYSA-N 0.000 description 1
SIRKQTVUKLFZBJ-UHFFFAOYSA-N n-(3-fluoropyridin-4-yl)-n-propylindol-1-amine;hydrochloride Chemical compound Cl.C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1F SIRKQTVUKLFZBJ-UHFFFAOYSA-N 0.000 description 1
HABJTJRYZYQHNS-UHFFFAOYSA-N n-(3-nitropyridin-4-yl)indol-1-amine Chemical compound [O-][N+](=O)C1=CN=CC=C1NN1C2=CC=CC=C2C=C1 HABJTJRYZYQHNS-UHFFFAOYSA-N 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
CEAIYWQYCSIDLK-BTJKTKAUSA-N n-butan-2-yl-n-pyridin-4-ylindol-1-amine;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.C1=CC2=CC=CC=C2N1N(C(C)CC)C1=CC=NC=C1 CEAIYWQYCSIDLK-BTJKTKAUSA-N 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
ZDFVWDHZXAGROF-UHFFFAOYSA-N n-propyl-n-pyridin-4-ylindol-1-amine;hydrochloride Chemical compound Cl.C1=CC2=CC=CC=C2N1N(CCC)C1=CC=NC=C1 ZDFVWDHZXAGROF-UHFFFAOYSA-N 0.000 description 1
ZKXLBNMUYTUYPY-UHFFFAOYSA-N n-propylindol-1-amine Chemical compound C1=CC=C2N(NCCC)C=CC2=C1 ZKXLBNMUYTUYPY-UHFFFAOYSA-N 0.000 description 1
UPQBWVOMAKRBQF-UHFFFAOYSA-N n-pyridin-2-yl-2,3-dihydroindol-1-amine Chemical class C1CC2=CC=CC=C2N1NC1=CC=CC=N1 UPQBWVOMAKRBQF-UHFFFAOYSA-N 0.000 description 1
230000010807 negative regulation of binding Effects 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
239000002581 neurotoxin Substances 0.000 description 1
231100000618 neurotoxin Toxicity 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000002795 scorpion venom Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CFMYXEVWODSLAX-QOZOJKKESA-N tetrodotoxin Chemical compound O([C@@]([C@H]1O)(O)O[C@H]2[C@@]3(O)CO)[C@H]3[C@@H](O)[C@]11[C@H]2[C@@H](O)N=C(N)N1 CFMYXEVWODSLAX-QOZOJKKESA-N 0.000 description 1
229950010357 tetrodotoxin Drugs 0.000 description 1
CFMYXEVWODSLAX-UHFFFAOYSA-N tetrodotoxin Natural products C12C(O)NC(=N)NC2(C2O)C(O)C3C(CO)(O)C1OC2(O)O3 CFMYXEVWODSLAX-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 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
- A61K31/435—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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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

Landscapes

Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Neurology (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO19980334A 1995-07-27 1998-01-26 Anvendelse av usubstituerte og substituerte N-(pyrrol-1-yl) pyridinaminer som antikonvulsive midler NO315148B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US50807195A	1995-07-27	1995-07-27
PCT/US1996/011408 WO1997004777A1 (en)	1995-07-27	1996-07-08	Use off unsubstituted and substituted n-(pyrrol-1-yl)pyridinamines as anticonvulsant agents

Publications (3)

Publication Number	Publication Date
NO980334D0 NO980334D0 (no)	1998-01-26
NO980334L NO980334L (no)	1998-03-26
NO315148B1 true NO315148B1 (no)	2003-07-21

Family

ID=24021262

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19980334A NO315148B1 (no)	1995-07-27	1998-01-26	Anvendelse av usubstituerte og substituerte N-(pyrrol-1-yl) pyridinaminer som antikonvulsive midler

Country Status (19)

Country	Link
EP (1)	EP0840609B1 (de)
JP (1)	JP4189029B2 (de)
KR (1)	KR100445629B1 (de)
CN (1)	CN1184969C (de)
AR (1)	AR003471A1 (de)
AT (1)	ATE218343T1 (de)
AU (1)	AU696007B2 (de)
CA (1)	CA2225156C (de)
DE (1)	DE69621617T2 (de)
DK (1)	DK0840609T3 (de)
ES (1)	ES2174081T3 (de)
IL (1)	IL122845A0 (de)
MX (1)	MX9800774A (de)
NO (1)	NO315148B1 (de)
NZ (1)	NZ312577A (de)
PT (1)	PT840609E (de)
TW (1)	TW464497B (de)
WO (1)	WO1997004777A1 (de)
ZA (1)	ZA966254B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GT200500063A (es) *	2004-04-01	2005-10-14		Metodo para tratar la esquizofrenia y/o anormalidades glucoregulatorias
FR2897614B1 (fr) *	2006-02-20	2008-05-23	Urogene	Forme cristalline du chlorhydrate de la besipirdine, procedes de preparation et utilisations

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5032599A (en) *	1986-11-12	1991-07-16	Hoechst-Roussel Pharmaceuticals Inc.	N-(pyrrol-l-yl)pyridinamines
EP0287982B1 (de) *	1987-04-24	1994-12-07	Hoechst-Roussel Pharmaceuticals Incorporated	N-(Pyridinyl)-1H-indol-1-amine, Verfahren zu deren Herstellung und ihre Verwendung als Arzneimittel
US4868190A (en) *	1988-12-27	1989-09-19	Hoechst-Roussel Pharmaceuticals, Inc.	N-pyridinyl-9H-carbazol-9-amines
US5179099A (en) *	1989-08-02	1993-01-12	Hoechst-Roussel Pharmaceuticals Incorporated	2,3-dihydro-1-(pyridinylamino)-indoles
US5356910A (en) *	1993-07-19	1994-10-18	Hoechst-Roussel Pharmaceuticals Inc.	Use of N-(pyridinyl)-1H-indol-1-amines for the treatment of obsessive-compulsive disorder

1996
- 1996-07-08 CN CNB961957808A patent/CN1184969C/zh not_active Expired - Fee Related
- 1996-07-08 DK DK96923693T patent/DK0840609T3/da active
- 1996-07-08 AT AT96923693T patent/ATE218343T1/de not_active IP Right Cessation
- 1996-07-08 ES ES96923693T patent/ES2174081T3/es not_active Expired - Lifetime
- 1996-07-08 NZ NZ312577A patent/NZ312577A/en not_active IP Right Cessation
- 1996-07-08 MX MX9800774A patent/MX9800774A/es not_active IP Right Cessation
- 1996-07-08 EP EP96923693A patent/EP0840609B1/de not_active Expired - Lifetime
- 1996-07-08 DE DE69621617T patent/DE69621617T2/de not_active Expired - Lifetime
- 1996-07-08 IL IL12284596A patent/IL122845A0/xx not_active IP Right Cessation
- 1996-07-08 JP JP50760297A patent/JP4189029B2/ja not_active Expired - Lifetime
- 1996-07-08 WO PCT/US1996/011408 patent/WO1997004777A1/en not_active Ceased
- 1996-07-08 PT PT96923693T patent/PT840609E/pt unknown
- 1996-07-08 CA CA002225156A patent/CA2225156C/en not_active Expired - Fee Related
- 1996-07-08 AU AU64547/96A patent/AU696007B2/en not_active Ceased
- 1996-07-08 KR KR10-1998-0700634A patent/KR100445629B1/ko not_active Expired - Fee Related
- 1996-07-23 ZA ZA9606254A patent/ZA966254B/xx unknown
- 1996-07-24 TW TW085109038A patent/TW464497B/zh not_active IP Right Cessation
- 1996-07-26 AR ARP960103787A patent/AR003471A1/es not_active Application Discontinuation
1998
- 1998-01-26 NO NO19980334A patent/NO315148B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR19990035973A (ko)	1999-05-25
IL122845A0 (en)	1998-08-16
EP0840609B1 (de)	2002-06-05
CA2225156A1 (en)	1997-02-13
WO1997004777A1 (en)	1997-02-13
JP4189029B2 (ja)	2008-12-03
KR100445629B1 (ko)	2004-10-14
NO980334D0 (no)	1998-01-26
DE69621617T2 (de)	2003-01-02
PT840609E (pt)	2002-10-31
DE69621617D1 (de)	2002-07-11
EP0840609A1 (de)	1998-05-13
AU696007B2 (en)	1998-08-27
AR003471A1 (es)	1998-08-05
CN1184969C (zh)	2005-01-19
NO980334L (no)	1998-03-26
JPH11510159A (ja)	1999-09-07
ZA966254B (en)	1997-02-11
ES2174081T3 (es)	2002-11-01
DK0840609T3 (da)	2002-09-30
CN1191486A (zh)	1998-08-26
NZ312577A (en)	1999-08-30
ATE218343T1 (de)	2002-06-15
TW464497B (en)	2001-11-21
AU6454796A (en)	1997-02-26
HK1015687A1 (en)	1999-10-22
MX9800774A (es)	1998-04-30
CA2225156C (en)	2003-06-10

Legal Events

Date	Code	Title	Description
2010-03-01	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US5929120A (en)	1999-07-27	Guainidino, formamidino, amino and related compounds for inhibiting osteoclast-mediated bone resorption
DE69522718T2 (de)	2002-02-07	Substituierte n-(indol-2-carbonyl)-amide und derivate als glycogen phosphorylase inhibitoren
TWI549676B (zh)	2016-09-21	組織蛋白去乙醯基酶之抑制劑
WO1996032383A1 (en)	1996-10-17	Acetamide derivatives, process for producing the same, and medicinal composition containing the same
EP0901373A1 (de)	1999-03-17	Alpha v Beta 3 ANTAGONISTEN
US20110212973A1 (en)	2011-09-01	Carbamate compound or salt thereof
NO310236B1 (no)	2001-06-11	Nye 2,3-diokso-1,2,3,4-tetrahydro-quinoksalinylderivater og farmasöytisk sammensetning omfattende samme
PT87308B (pt)	1992-08-31	Processo para a preparacao de n-(piridinil)-1h-indol-1-aminas e de composicoes farmaceuticas que os contem
JPH0568474B2 (de)	1993-09-29
US8022071B2 (en)	2011-09-20	Nitrogenous heterocyclic compounds
US5925655A (en)	1999-07-20	αv β3 antagonists
WO1998009960A1 (en)	1998-03-12	2,4-disubstituted pyrimidine derivatives, process for producing the same, and medicinal compositions containing the same
KR20100081349A (ko)	2010-07-14	브라디키닌 ｂ１ 길항제인 신규 비펩티드 유도체
KR101027623B1 (ko)	2011-04-06	브라디키닌 길항물질인 신규 페난트리딘 유도체
JP2807633B2 (ja)	1998-10-08	Ｎ−（ピリジニル）−ｉｈ−インドール−１−アミンを含有する強迫疾患治療剤
EP0840609B1 (de)	2002-06-05	Verwendung von substituierten und nichtsubstituierten n-(pyrrol-1-yl)pyridinaminen als antikonvulsiva
NO323263B1 (no)	2007-02-19	Heterosyklisk derivat, fremgangsmater for dets fremstilling, farmasoytiske sammensetninger som inneholder dette, anvendelse av dette for fremstilling av et preparat for medisinsk bruk samt nevnte derivat til bruk som medikament
US5776955A (en)	1998-07-07	Use of unsubstituted and substituted n-(pyrrol-1-yl)pyridinamines as anticonvulsant agents
IL151521A (en)	2004-09-27	Use of unsubstituted and substituted n-(pyrrol-1-yl) pyridinamines in the preparation of anticonvulsant pharmaceutical compositions, and pharmaceutical compositions comprising them
KR100556559B1 (ko)	2006-03-06	2-(4-(4-(4,5-디클로로-2-메틸이미다졸-1-일)부틸)-1-피페라지닐)-5-플루오로피리미딘, 이것의 제조 방법 및 이것의치료적 용도
AU2003221394A1 (en)	2003-09-29	Novel pyridone derivative