RU2185372C2 - Алкилзамещенные циклические амины в качестве селективных лигандов d3-допамина - Google Patents
Алкилзамещенные циклические амины в качестве селективных лигандов d3-допамина Download PDFInfo
- Publication number
- RU2185372C2 RU2185372C2 RU98123954/04A RU98123954A RU2185372C2 RU 2185372 C2 RU2185372 C2 RU 2185372C2 RU 98123954/04 A RU98123954/04 A RU 98123954/04A RU 98123954 A RU98123954 A RU 98123954A RU 2185372 C2 RU2185372 C2 RU 2185372C2
- Authority
- RU
- Russia
- Prior art keywords
- dipropylamino
- mmol
- give
- mixture
- alkyl
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title abstract 2
- VYFYYTLLBUKUHU-JJBFAFJOSA-N 4-[2-deuterio-2-(dideuterioamino)ethyl]benzene-1,2-diol Chemical compound [2H]N([2H])C([2H])CC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-JJBFAFJOSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 125000003118 aryl group Chemical group 0.000 claims abstract description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 125000005518 carboxamido group Chemical group 0.000 claims abstract description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- -1 C 1 -C 6 alkylaryl Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- VYXPNQWWRFIRQU-UHFFFAOYSA-N 2-(dipropylamino)-6-ethoxy-2,3-dihydro-1h-indene-5-carboxamide Chemical compound CCOC1=C(C(N)=O)C=C2CC(N(CCC)CCC)CC2=C1 VYXPNQWWRFIRQU-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 239000000460 chlorine Chemical group 0.000 abstract description 31
- 239000000126 substance Substances 0.000 abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 208000035475 disorder Diseases 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 3
- 229960003638 dopamine Drugs 0.000 abstract description 3
- 239000011737 fluorine Chemical group 0.000 abstract description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 277
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 266
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 181
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 178
- 238000000034 method Methods 0.000 description 150
- 239000000203 mixture Substances 0.000 description 150
- 235000019439 ethyl acetate Nutrition 0.000 description 114
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
- 239000007787 solid Substances 0.000 description 104
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- 239000003921 oil Substances 0.000 description 69
- 235000019198 oils Nutrition 0.000 description 69
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 67
- 238000000746 purification Methods 0.000 description 62
- 239000000741 silica gel Substances 0.000 description 62
- 229910002027 silica gel Inorganic materials 0.000 description 62
- 150000003840 hydrochlorides Chemical class 0.000 description 58
- 239000002904 solvent Substances 0.000 description 55
- 239000000243 solution Substances 0.000 description 54
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 239000012267 brine Substances 0.000 description 43
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000013078 crystal Substances 0.000 description 31
- 239000012265 solid product Substances 0.000 description 30
- 239000010410 layer Substances 0.000 description 29
- PTQJCZPTMMMLFD-UHFFFAOYSA-N 2-(dipropylamino)-2,3-dihydro-1H-indene-5,6-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2CC(N(CCC)CCC)CC2=C1 PTQJCZPTMMMLFD-UHFFFAOYSA-N 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 26
- 238000002425 crystallisation Methods 0.000 description 25
- 230000008025 crystallization Effects 0.000 description 25
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
- 238000003818 flash chromatography Methods 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 23
- 239000000284 extract Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 230000027455 binding Effects 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- IIFBIBXUQRKIAF-QGZVFWFLSA-N (2r)-7-(aminomethyl)-n,n-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=C(CN)C=C2C[C@H](N(CCC)CCC)CCC2=C1 IIFBIBXUQRKIAF-QGZVFWFLSA-N 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 229910052938 sodium sulfate Inorganic materials 0.000 description 17
- 235000011152 sodium sulphate Nutrition 0.000 description 17
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- QPAXVCZGFPQHNY-UHFFFAOYSA-N n,n-dipropyl-1,2,3,5,6,7-hexahydrocyclopenta[f]isoindol-6-amine Chemical compound C1=C2CC(N(CCC)CCC)CC2=CC2=C1CNC2 QPAXVCZGFPQHNY-UHFFFAOYSA-N 0.000 description 14
- 229910004373 HOAc Inorganic materials 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 12
- 238000011097 chromatography purification Methods 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- HUIYHSMYBBZQKW-SNVBAGLBSA-N (2r)-4-(4-bromophenyl)-2-(methoxycarbonylamino)butanoic acid Chemical compound COC(=O)N[C@@H](C(O)=O)CCC1=CC=C(Br)C=C1 HUIYHSMYBBZQKW-SNVBAGLBSA-N 0.000 description 9
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 201000000980 schizophrenia Diseases 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229940124530 sulfonamide Drugs 0.000 description 7
- OLBGSXOWGPLPGQ-MRXNPFEDSA-N (2r)-7-bromo-n,n-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=C(Br)C=C2C[C@H](N(CCC)CCC)CCC2=C1 OLBGSXOWGPLPGQ-MRXNPFEDSA-N 0.000 description 6
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- 101150097070 Drd3 gene Proteins 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 150000003456 sulfonamides Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- IMJMPHINVPHZNL-SECBINFHSA-N (2r)-4-(4-bromophenyl)-2-(methoxycarbonylamino)-4-oxobutanoic acid Chemical compound COC(=O)N[C@@H](C(O)=O)CC(=O)C1=CC=C(Br)C=C1 IMJMPHINVPHZNL-SECBINFHSA-N 0.000 description 5
- XPOMHSYWYKZDHB-UHFFFAOYSA-N C(CC)N(CCC)N1C(C=2C=C3C(=CC=2C1=O)CCC3)=O Chemical compound C(CC)N(CCC)N1C(C=2C=C3C(=CC=2C1=O)CCC3)=O XPOMHSYWYKZDHB-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 235000013877 carbamide Nutrition 0.000 description 5
- 150000003857 carboxamides Chemical class 0.000 description 5
- 208000015114 central nervous system disease Diseases 0.000 description 5
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 5
- QZPOGJKACPURIZ-UHFFFAOYSA-N methyl 2-(dipropylamino)-6-ethoxy-2,3-dihydro-1h-indene-5-carboxylate Chemical compound CCOC1=C(C(=O)OC)C=C2CC(N(CCC)CCC)CC2=C1 QZPOGJKACPURIZ-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- FJBYZVUXAPGKBS-MRXNPFEDSA-N (2r)-2-n,2-n-dipropyl-1,2,3,4-tetrahydronaphthalene-2,7-diamine Chemical compound C1=C(N)C=C2C[C@H](N(CCC)CCC)CCC2=C1 FJBYZVUXAPGKBS-MRXNPFEDSA-N 0.000 description 4
- WWDRSOCNPDYSMG-QVDQXJPCSA-N (2r)-3-bromo-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC=C2CC(Br)[C@H](N)CC2=C1 WWDRSOCNPDYSMG-QVDQXJPCSA-N 0.000 description 4
- PNTPMWBRGXAFII-SNVBAGLBSA-N (2r)-7-bromo-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=C(Br)C=C2C[C@H](N)CCC2=C1 PNTPMWBRGXAFII-SNVBAGLBSA-N 0.000 description 4
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 4
- DXNRCUOAEJJDTF-UHFFFAOYSA-N 2-(dipropylamino)-6-hydroxy-2,3-dihydro-1h-indene-5-carboxamide Chemical compound OC1=C(C(N)=O)C=C2CC(N(CCC)CCC)CC2=C1 DXNRCUOAEJJDTF-UHFFFAOYSA-N 0.000 description 4
- JRMLAHCEQMZBNK-UHFFFAOYSA-N 3-(aminomethyl)-n,n-dipropyl-6,7-dihydro-5h-cyclopenta[c]pyridin-6-amine Chemical compound N1=C(CN)C=C2CC(N(CCC)CCC)CC2=C1 JRMLAHCEQMZBNK-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000006847 BOC protecting group Chemical group 0.000 description 4
- MZKCOHQOZRZIAM-UHFFFAOYSA-N C(N)(O)=O.C(C)(C)(C)C1CC(CC2=C1N=C(S2)C=O)NCCC Chemical compound C(N)(O)=O.C(C)(C)(C)C1CC(CC2=C1N=C(S2)C=O)NCCC MZKCOHQOZRZIAM-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- RRTHRFFJGGDJFZ-UHFFFAOYSA-N [2-(dipropylamino)-6-hydroxy-2,3-dihydro-1h-inden-5-yl] trifluoromethanesulfonate Chemical compound OC1=C(OS(=O)(=O)C(F)(F)F)C=C2CC(N(CCC)CCC)CC2=C1 RRTHRFFJGGDJFZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- XLQGSPCYIFYHDC-UHFFFAOYSA-N methyl 6-butoxy-2-(dipropylamino)-2,3-dihydro-1h-indene-5-carboxylate Chemical compound C1=C(C(=O)OC)C(OCCCC)=CC2=C1CC(N(CCC)CCC)C2 XLQGSPCYIFYHDC-UHFFFAOYSA-N 0.000 description 4
- NHAJAABVIJADQA-UHFFFAOYSA-N n-propyl-4,5,6,7-tetrahydro-1,3-benzothiazol-6-amine Chemical compound C1C(NCCC)CCC2=C1SC=N2 NHAJAABVIJADQA-UHFFFAOYSA-N 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
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- 229930192474 thiophene Natural products 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
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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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1879496P | 1996-05-31 | 1996-05-31 | |
| US60/018,794 | 1996-05-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98123954A RU98123954A (ru) | 2000-11-20 |
| RU2185372C2 true RU2185372C2 (ru) | 2002-07-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98123954/04A RU2185372C2 (ru) | 1996-05-31 | 1997-05-12 | Алкилзамещенные циклические амины в качестве селективных лигандов d3-допамина |
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|---|---|
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| EP (1) | EP0923542B1 (enExample) |
| JP (1) | JP2000511529A (enExample) |
| KR (1) | KR20000016147A (enExample) |
| CN (1) | CN1159292C (enExample) |
| AT (1) | ATE247639T1 (enExample) |
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| CA (1) | CA2255612A1 (enExample) |
| CZ (1) | CZ370198A3 (enExample) |
| DE (1) | DE69724259T2 (enExample) |
| DK (1) | DK0923542T3 (enExample) |
| ES (1) | ES2205227T3 (enExample) |
| FI (1) | FI982572A7 (enExample) |
| NO (1) | NO314398B1 (enExample) |
| NZ (1) | NZ332538A (enExample) |
| PL (1) | PL187296B1 (enExample) |
| PT (1) | PT923542E (enExample) |
| RU (1) | RU2185372C2 (enExample) |
| SI (1) | SI0923542T1 (enExample) |
| SK (1) | SK282725B6 (enExample) |
| WO (1) | WO1997045403A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2387638C2 (ru) * | 2004-06-02 | 2010-04-27 | Ф.Хофманн-ля Рош АГ | Производные нафталина, пригодные в качестве лигандов рецепторов 3 гистамина |
Families Citing this family (24)
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| AR022230A1 (es) * | 1999-01-12 | 2002-09-04 | Abbott Gmbh & Co Kg | Compuestos de triazol, composicion farmaceutica que los comprende y uso de los mismos para preparar dicha composicion |
| EP1088821A1 (en) | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives |
| DK1257527T3 (da) * | 2000-02-22 | 2004-01-12 | Upjohn Co | (2S)-Aminoindanderivater, en fremgangsmåde til deres præparation og deres anvendelse som selektive dopamin-D3-ligander |
| AU2001288329A1 (en) | 2000-09-18 | 2002-04-02 | Pharmacia Ab | Process to prepare (2s)-2-(dipropylamino)-6-ethoxy-2,3-dihydro-1h-indene-5- carboxamide |
| EP1193268A1 (en) | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases |
| HU227543B1 (en) | 2001-09-28 | 2011-08-29 | Richter Gedeon Nyrt | N-[4-(2-piperazin- and 2-piperidin-1-yl-ethyl)-cyclohexyl]-sulfon- and sulfamides, process for their preparation, their use and pharmaceutical compositions containing them |
| EP1495004A2 (en) * | 2002-02-13 | 2005-01-12 | Glaxo Group Limited | Benzenesulfonamide derivatives and their use as dopamine d3 and d2 receptor ligands |
| JP5193602B2 (ja) * | 2004-10-14 | 2013-05-08 | アボット ゲーエムベーハー ウント カンパニー カーゲー | ドーパミンd3受容体の調節に応答する障害の治療に好適なアリールスルホニルメチルまたはアリールスルホンアミド置換芳香族化合物 |
| MX2007004358A (es) | 2004-10-14 | 2007-07-17 | Abbott Gmbh & Co Kg | Compuestos de azabicicloheptilo adecuados para tratar trastornos que responden a la modulacion del receptor de dopamina d3. |
| MX2007004354A (es) * | 2004-10-14 | 2007-07-17 | Abbot Gmbh & Co Kg | Compuestos aromaticos biciclicos sustituidos con aminometilo adecuados para tratar trastornos que responden a la modulacion del receptor de dopamina d3. |
| EP2371814A1 (en) * | 2004-10-14 | 2011-10-05 | Abbott GmbH & Co. KG | Aminoethylaromatic compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor |
| NZ555121A (en) | 2004-10-14 | 2011-01-28 | Abbott Gmbh & Co Kg | 6-amino(aza)indane compounds suitable for treating disorders that respond to modulation of the dopamine d3 recptor |
| EP2311803A1 (en) | 2004-10-14 | 2011-04-20 | Abbott GmbH & Co. KG | Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor |
| TW200800959A (en) * | 2005-06-10 | 2008-01-01 | Wyeth Corp | Piperazine-piperidine antagonists and agonists of the 5-HT1a receptor |
| GB0512099D0 (en) * | 2005-06-14 | 2005-07-20 | Glaxo Group Ltd | Compounds |
| AU2006259294A1 (en) * | 2005-06-17 | 2006-12-28 | Wyeth | Tricyclic compounds useful as serotonin inhibitors and 5-HT1A agonists and antagonists |
| US20080262228A1 (en) * | 2006-11-28 | 2008-10-23 | Wyeth | Metabolites of 5-fluoro-8- quinoline and methods of preparation and uses thereof |
| GB0721333D0 (en) * | 2007-10-31 | 2007-12-12 | Motac Neuroscience Ltd | Medicaments |
| GB0721332D0 (en) * | 2007-10-31 | 2007-12-12 | Motac Neuroscience Ltd | Medicaments |
| CN102786483B (zh) * | 2011-05-19 | 2016-03-30 | 复旦大学 | 4-(4-苯基哌嗪基)喹唑啉类衍生物的药用用途 |
| EP3174853B1 (en) * | 2014-07-30 | 2018-12-12 | F.Hoffmann-La Roche Ag | 6-amino-5,6,7,8-tetrahydronaphthalen-2-yl or 3-aminochroman-7-yl derivatives as taar modulators |
| WO2018200571A1 (en) | 2017-04-25 | 2018-11-01 | Arbutus Biopharma Corporation | Substituted 2,3-dihydro-1h-indene analogs and methods using same |
| CN110041318B (zh) * | 2018-01-17 | 2022-07-29 | 中国科学院上海药物研究所 | 一类多巴胺d5受体激动剂及其制备和应用 |
| CA3093851A1 (en) | 2018-03-29 | 2019-10-03 | Arbutus Biopharma Corporation | Substituted 1,1'-biphenyl compounds, analogues thereof, and methods using same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SU384229A3 (enExample) * | 1969-12-12 | 1973-05-23 | ||
| WO1994021608A1 (en) * | 1993-03-25 | 1994-09-29 | The Upjohn Company | Indoletetralins having dopaminergic activity |
| WO1995004713A1 (en) * | 1993-08-06 | 1995-02-16 | The Upjohn Company | 2-aminoindans as selective dopamine d3 ligands |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2752659A1 (de) * | 1976-12-07 | 1978-06-08 | Sandoz Ag | Neue tetralinderivate, ihre herstellung und verwendung |
| FR2512814A1 (fr) * | 1981-09-16 | 1983-03-18 | Synthelabo | Derives d'amino-2 tetrahydro-1,2,3,4 naphtalene, leur preparation et leur application en therapeutique |
| US4448990A (en) * | 1982-11-16 | 1984-05-15 | Eli Lilly And Company | Hydroxyaminotetralincarboxamides |
| JPS6169747A (ja) * | 1984-08-31 | 1986-04-10 | Otsuka Pharmaceut Co Ltd | 2,3―ジヒドロ―1h―インデン誘導体及びその製造法 |
| ATE45735T1 (de) * | 1984-12-22 | 1989-09-15 | Thomae Gmbh Dr K | Tetrahydro-benzthiazole, deren herstellung und deren verwendung als zwischenprodukte oder als arnzneimittel. |
| DE3719924A1 (de) * | 1986-12-22 | 1988-06-30 | Bayer Ag | 8-substituierte 2-aminotetraline |
| US5225596A (en) * | 1989-01-09 | 1993-07-06 | The Upjohn Company | Halo substituted aminotetralins |
| ES2159017T3 (es) * | 1995-02-01 | 2001-09-16 | Upjohn Co | 2-aminoindanos como ligandos selectivos de la dopamina d3. |
| US6008219A (en) * | 1995-03-27 | 1999-12-28 | Smithkline Beech P.L.C. | Bicyclic amine derivatives and their use as anti-psychotic agents |
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1997
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1998
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|---|---|---|---|---|
| SU384229A3 (enExample) * | 1969-12-12 | 1973-05-23 | ||
| WO1994021608A1 (en) * | 1993-03-25 | 1994-09-29 | The Upjohn Company | Indoletetralins having dopaminergic activity |
| WO1995004713A1 (en) * | 1993-08-06 | 1995-02-16 | The Upjohn Company | 2-aminoindans as selective dopamine d3 ligands |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2387638C2 (ru) * | 2004-06-02 | 2010-04-27 | Ф.Хофманн-ля Рош АГ | Производные нафталина, пригодные в качестве лигандов рецепторов 3 гистамина |
Also Published As
| Publication number | Publication date |
|---|---|
| SI0923542T1 (en) | 2004-02-29 |
| AU3060197A (en) | 1998-01-05 |
| US6084130A (en) | 2000-07-04 |
| CN1217711A (zh) | 1999-05-26 |
| EP0923542A1 (en) | 1999-06-23 |
| KR20000016147A (ko) | 2000-03-25 |
| NO985599L (no) | 1998-11-30 |
| NZ332538A (en) | 2001-02-23 |
| DE69724259D1 (de) | 2003-09-25 |
| ES2205227T3 (es) | 2004-05-01 |
| FI982572A0 (fi) | 1998-11-27 |
| WO1997045403A1 (en) | 1997-12-04 |
| DK0923542T3 (da) | 2003-11-17 |
| JP2000511529A (ja) | 2000-09-05 |
| HK1019326A1 (en) | 2000-02-03 |
| CN1159292C (zh) | 2004-07-28 |
| EP0923542B1 (en) | 2003-08-20 |
| AU720414B2 (en) | 2000-06-01 |
| PL330207A1 (en) | 1999-04-26 |
| PT923542E (pt) | 2003-12-31 |
| NO985599D0 (no) | 1998-11-30 |
| SK148898A3 (en) | 2000-03-13 |
| ATE247639T1 (de) | 2003-09-15 |
| CZ370198A3 (cs) | 1999-05-12 |
| FI982572A7 (fi) | 1998-11-27 |
| PL187296B1 (pl) | 2004-06-30 |
| NO314398B1 (no) | 2003-03-17 |
| DE69724259T2 (de) | 2004-06-09 |
| CA2255612A1 (en) | 1997-12-04 |
| SK282725B6 (sk) | 2002-11-06 |
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