CA2255612A1 - Aryl substituted cyclic amines as selective dopamine d3 ligands - Google Patents
Aryl substituted cyclic amines as selective dopamine d3 ligands Download PDFInfo
- Publication number
- CA2255612A1 CA2255612A1 CA002255612A CA2255612A CA2255612A1 CA 2255612 A1 CA2255612 A1 CA 2255612A1 CA 002255612 A CA002255612 A CA 002255612A CA 2255612 A CA2255612 A CA 2255612A CA 2255612 A1 CA2255612 A1 CA 2255612A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- dipropylamino
- alkyl
- mmol
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 29
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title description 8
- 229960003638 dopamine Drugs 0.000 title description 4
- 239000003446 ligand Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 102000004073 Dopamine D3 Receptors Human genes 0.000 claims abstract description 10
- 108090000525 Dopamine D3 Receptors Proteins 0.000 claims abstract description 10
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- 230000000694 effects Effects 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 147
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
- -1 C1-C6 alkylAryl Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000000460 chlorine Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 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 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 274
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 258
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 178
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 171
- 239000007787 solid Substances 0.000 description 134
- 235000019439 ethyl acetate Nutrition 0.000 description 113
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 106
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 96
- 239000000203 mixture Substances 0.000 description 82
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 82
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
- 239000000741 silica gel Substances 0.000 description 62
- 229910002027 silica gel Inorganic materials 0.000 description 62
- 229910001868 water Inorganic materials 0.000 description 62
- 238000000746 purification Methods 0.000 description 61
- 239000000243 solution Substances 0.000 description 57
- 150000003840 hydrochlorides Chemical class 0.000 description 55
- 239000002904 solvent Substances 0.000 description 53
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
- 229940093499 ethyl acetate Drugs 0.000 description 48
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 42
- 239000012267 brine Substances 0.000 description 42
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- 229960004132 diethyl ether Drugs 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 32
- 239000013078 crystal Substances 0.000 description 30
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 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 27
- 150000001412 amines Chemical class 0.000 description 27
- 239000010410 layer Substances 0.000 description 26
- 238000002425 crystallisation Methods 0.000 description 25
- 230000008025 crystallization Effects 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- 239000000284 extract Substances 0.000 description 22
- 238000003818 flash chromatography Methods 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- PWYJJQYPSILKKB-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-(1-hydroxycyclopentyl)-2-phenylacetate;hydrochloride Chemical compound Cl.C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 PWYJJQYPSILKKB-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 229910052938 sodium sulfate Inorganic materials 0.000 description 18
- 235000011152 sodium sulphate Nutrition 0.000 description 18
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- 235000017550 sodium carbonate Nutrition 0.000 description 14
- 229910004373 HOAc Inorganic materials 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- 230000002829 reductive effect Effects 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
- 238000010992 reflux Methods 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 229940124530 sulfonamide Drugs 0.000 description 10
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 9
- UEAZUOVAYXATKM-UHFFFAOYSA-N 1-propylnaphthalen-2-amine Chemical compound C(CC)C1=C(C=CC2=CC=CC=C12)N UEAZUOVAYXATKM-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 235000013877 carbamide Nutrition 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 150000003857 carboxamides Chemical class 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 150000003456 sulfonamides Chemical group 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 6
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 201000000980 schizophrenia Diseases 0.000 description 6
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 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 5
- 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 5
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- STIYIFOPYJOPRS-SNVBAGLBSA-N methyl n-[(2r)-7-bromo-1-oxo-3,4-dihydro-2h-naphthalen-2-yl]carbamate Chemical compound C1=C(Br)C=C2C(=O)[C@H](NC(=O)OC)CCC2=C1 STIYIFOPYJOPRS-SNVBAGLBSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 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
- 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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 4
- CTZXVGSIGHCXGQ-UHFFFAOYSA-N 5,7-dihydro-4h-1,3-benzothiazol-6-one Chemical compound C1C(=O)CCC2=C1SC=N2 CTZXVGSIGHCXGQ-UHFFFAOYSA-N 0.000 description 4
- FGPLHVMQLSBGSR-UHFFFAOYSA-N C1C(NCCC)CCC2=C1SC(C=O)=N2 Chemical compound C1C(NCCC)CCC2=C1SC(C=O)=N2 FGPLHVMQLSBGSR-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 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
- 239000002552 dosage form Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- ZOTLHZNARGTDSZ-LLVKDONJSA-N methyl N-[(2R)-7-bromo-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C1=C(Br)C=C2C[C@H](NC(=O)OC)CCC2=C1 ZOTLHZNARGTDSZ-LLVKDONJSA-N 0.000 description 4
- JPEHNUYVLFKKGY-GSVOUGTGSA-N methyl n-[(3r)-2,5-dioxooxolan-3-yl]carbamate Chemical compound COC(=O)N[C@@H]1CC(=O)OC1=O JPEHNUYVLFKKGY-GSVOUGTGSA-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
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-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 3
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- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000006513 pyridinyl methyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 239000008215 water for injection Substances 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/28—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
-
- 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)
- General Chemical & Material Sciences (AREA)
- 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1879496P | 1996-05-31 | 1996-05-31 | |
| US60/018,794 | 1996-05-31 | ||
| PCT/US1997/007650 WO1997045403A1 (en) | 1996-05-31 | 1997-05-12 | Aryl substituted cyclic amines as selective dopamine d3 ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2255612A1 true CA2255612A1 (en) | 1997-12-04 |
Family
ID=21789817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002255612A Abandoned CA2255612A1 (en) | 1996-05-31 | 1997-05-12 | Aryl substituted cyclic amines as selective dopamine d3 ligands |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6084130A (enExample) |
| EP (1) | EP0923542B1 (enExample) |
| JP (1) | JP2000511529A (enExample) |
| KR (1) | KR20000016147A (enExample) |
| CN (1) | CN1159292C (enExample) |
| AT (1) | ATE247639T1 (enExample) |
| AU (1) | AU720414B2 (enExample) |
| 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) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP4594386B2 (ja) * | 2004-06-02 | 2010-12-08 | エフ.ホフマン−ラ ロシュ アーゲー | ヒスタミン3受容体のリガンドとして有用なナフタレン誘導体 |
| 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 |
Family Cites Families (11)
| 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 |
| DK0690843T3 (da) * | 1993-03-25 | 2000-11-13 | Upjohn Co | Fornyl- eller cyanosubstituerede indolderivater med dopaninerg aktivitet |
| AU7513494A (en) * | 1993-08-06 | 1995-02-28 | Upjohn Company, The | 2-aminoindans as selective dopamine d3 ligands |
| 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 |
-
1997
- 1997-05-12 EP EP97925470A patent/EP0923542B1/en not_active Expired - Lifetime
- 1997-05-12 SK SK1488-98A patent/SK282725B6/sk unknown
- 1997-05-12 KR KR1019980709715A patent/KR20000016147A/ko not_active Ceased
- 1997-05-12 RU RU98123954/04A patent/RU2185372C2/ru not_active IP Right Cessation
- 1997-05-12 AU AU30601/97A patent/AU720414B2/en not_active Ceased
- 1997-05-12 DE DE69724259T patent/DE69724259T2/de not_active Expired - Fee Related
- 1997-05-12 ES ES97925470T patent/ES2205227T3/es not_active Expired - Lifetime
- 1997-05-12 DK DK97925470T patent/DK0923542T3/da active
- 1997-05-12 CN CNB971943265A patent/CN1159292C/zh not_active Expired - Fee Related
- 1997-05-12 CZ CZ983701A patent/CZ370198A3/cs unknown
- 1997-05-12 WO PCT/US1997/007650 patent/WO1997045403A1/en not_active Ceased
- 1997-05-12 AT AT97925470T patent/ATE247639T1/de not_active IP Right Cessation
- 1997-05-12 CA CA002255612A patent/CA2255612A1/en not_active Abandoned
- 1997-05-12 SI SI9730586T patent/SI0923542T1/xx unknown
- 1997-05-12 PT PT97925470T patent/PT923542E/pt unknown
- 1997-05-12 JP JP09542424A patent/JP2000511529A/ja not_active Ceased
- 1997-05-20 US US08/859,587 patent/US6084130A/en not_active Expired - Fee Related
-
1998
- 1998-11-02 NZ NZ332538A patent/NZ332538A/en unknown
- 1998-11-02 PL PL97330207A patent/PL187296B1/pl not_active IP Right Cessation
- 1998-11-27 FI FI982572A patent/FI982572A7/fi not_active IP Right Cessation
- 1998-11-30 NO NO19985599A patent/NO314398B1/no not_active Application Discontinuation
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 |
| RU2185372C2 (ru) | 2002-07-20 |
| 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 |
| SK282725B6 (sk) | 2002-11-06 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |