SK16242000A3 - Fenylsulfónamid-fenyletylamíny užitočné ako dopamínové receptory - Google Patents

Fenylsulfónamid-fenyletylamíny užitočné ako dopamínové receptory Download PDF

Info

Publication number: SK16242000A3
Authority: SK; Slovakia
Prior art keywords: ethyl; propylamine; phenyl; alkyl; compound
Prior art date: 1998-05-14

Application number

SK1624-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Arthur G. Romero

Jeffrey A. Leiby

Original Assignee

Pharmacia And Upjohn Company

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-05-14

Filing date

1999-05-07

Publication date

2001-06-11

1999-05-07 Application filed by Pharmacia And Upjohn Company filed Critical Pharmacia And Upjohn Company

2001-06-11 Publication of SK16242000A3 publication Critical patent/SK16242000A3/sk

Links

GNLBKOISUOPBOL-UHFFFAOYSA-N benzenesulfonamide;2-phenylethanamine Chemical class NCCC1=CC=CC=C1.NS(=O)(=O)C1=CC=CC=C1 GNLBKOISUOPBOL-UHFFFAOYSA-N 0.000 title description 2
102000015554 Dopamine receptor Human genes 0.000 title 1
108050004812 Dopamine receptor Proteins 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 47
102000004073 Dopamine D3 Receptors Human genes 0.000 claims abstract description 7
108090000525 Dopamine D3 Receptors Proteins 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
230000000694 effects Effects 0.000 claims abstract description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
208000015114 central nervous system disease Diseases 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 26
-1 4-Chlorobenzenesulfonamido Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
GCWGADZVRFZLBG-UHFFFAOYSA-N tert-butyl 2-[2-(4-aminophenyl)ethylamino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)NCCC1=CC=C(N)C=C1 GCWGADZVRFZLBG-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 5
YYOHEGJBKTVTLK-UHFFFAOYSA-N 2,4-dichloro-n-[4-[2-(propylamino)ethyl]phenyl]benzenesulfonamide Chemical compound C1=CC(CCNCCC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1Cl YYOHEGJBKTVTLK-UHFFFAOYSA-N 0.000 claims description 4
DOFFSUIUWSPOJI-UHFFFAOYSA-N 2-chloro-4-fluoro-n-[4-[2-(propylamino)ethyl]phenyl]benzenesulfonamide Chemical compound C1=CC(CCNCCC)=CC=C1NS(=O)(=O)C1=CC=C(F)C=C1Cl DOFFSUIUWSPOJI-UHFFFAOYSA-N 0.000 claims description 4
XUAUSHRTHCVYEJ-UHFFFAOYSA-N 2-fluoro-n-[3-[2-(propylamino)ethyl]phenyl]benzenesulfonamide Chemical compound CCCNCCC1=CC=CC(NS(=O)(=O)C=2C(=CC=CC=2)F)=C1 XUAUSHRTHCVYEJ-UHFFFAOYSA-N 0.000 claims description 4
GYCXCBYOHASGSD-UHFFFAOYSA-N 3-chloro-n-[3-[2-(propylamino)ethyl]phenyl]benzenesulfonamide Chemical compound CCCNCCC1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 GYCXCBYOHASGSD-UHFFFAOYSA-N 0.000 claims description 4
GLBXYJLKQWSMHH-UHFFFAOYSA-N 4-bromo-n-[4-[2-(propylamino)ethyl]phenyl]benzenesulfonamide Chemical compound C1=CC(CCNCCC)=CC=C1NS(=O)(=O)C1=CC=C(Br)C=C1 GLBXYJLKQWSMHH-UHFFFAOYSA-N 0.000 claims description 4
VCHHCUQGXMWXAM-UHFFFAOYSA-N 4-chloro-n-[4-[2-(propylamino)ethyl]phenyl]benzenesulfonamide Chemical compound C1=CC(CCNCCC)=CC=C1NS(=O)(=O)C1=CC=C(Cl)C=C1 VCHHCUQGXMWXAM-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000000217 alkyl group 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 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 claims 2
JGGQWSXZZQPZTR-UHFFFAOYSA-N n-[4-[2-(propylamino)ethyl]phenyl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound C1=CC(CCNCCC)=CC=C1NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 JGGQWSXZZQPZTR-UHFFFAOYSA-N 0.000 claims 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 abstract 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000002360 preparation method Methods 0.000 description 13
239000007787 solid Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000203 mixture Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000012267 brine Substances 0.000 description 7
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
238000003818 flash chromatography Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
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239000002552 dosage form Substances 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
208000011117 substance-related disease Diseases 0.000 description 4
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 4
238000011282 treatment Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
208000019901 Anxiety disease Diseases 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
208000018737 Parkinson disease Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000036506 anxiety Effects 0.000 description 3
150000004982 aromatic amines Chemical class 0.000 description 3
239000002775 capsule Substances 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
JVMHULJEYUQYSH-UHFFFAOYSA-N 2-(4-nitrophenyl)ethylazanium;chloride Chemical compound Cl.NCCC1=CC=C([N+]([O-])=O)C=C1 JVMHULJEYUQYSH-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
206010012289 Dementia Diseases 0.000 description 2
206010013654 Drug abuse Diseases 0.000 description 2
206010026749 Mania Diseases 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
241000251539 Vertebrata <Metazoa> Species 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
206010013663 drug dependence Diseases 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
OOKNVVKYQLZQDC-UHFFFAOYSA-N n-[4-[2-(propylamino)ethyl]phenyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound C1=CC(CCNCCC)=CC=C1NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 OOKNVVKYQLZQDC-UHFFFAOYSA-N 0.000 description 2
PAZVJIOFFOOQLQ-UHFFFAOYSA-N n-ethyl-n-propylaniline Chemical compound CCCN(CC)C1=CC=CC=C1 PAZVJIOFFOOQLQ-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
230000033764 rhythmic process Effects 0.000 description 2
208000019116 sleep disease Diseases 0.000 description 2
239000007909 solid dosage form Substances 0.000 description 2
FDTPBIKNYWQLAE-UHFFFAOYSA-N 2,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 FDTPBIKNYWQLAE-UHFFFAOYSA-N 0.000 description 1
KWHVBVJDKLSOTB-UHFFFAOYSA-N 2-(3-methylphenyl)ethanol Chemical compound CC1=CC=CC(CCO)=C1 KWHVBVJDKLSOTB-UHFFFAOYSA-N 0.000 description 1
PWZWTSYUZQZFKE-UHFFFAOYSA-N 2-(3-nitrophenyl)ethanol Chemical compound OCCC1=CC=CC([N+]([O-])=O)=C1 PWZWTSYUZQZFKE-UHFFFAOYSA-N 0.000 description 1
FCFPJKHVCHKCMP-UHFFFAOYSA-N 2-chloro-4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C(Cl)=C1 FCFPJKHVCHKCMP-UHFFFAOYSA-N 0.000 description 1
ZSZKAQCISWFDCQ-UHFFFAOYSA-N 2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC=C1S(Cl)(=O)=O ZSZKAQCISWFDCQ-UHFFFAOYSA-N 0.000 description 1
OINWZUJVEXUHCC-UHFFFAOYSA-N 3-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=CC(S(Cl)(=O)=O)=C1 OINWZUJVEXUHCC-UHFFFAOYSA-N 0.000 description 1
UHCDBMIOLNKDHG-UHFFFAOYSA-N 4-(trifluoromethoxy)benzenesulfonyl chloride Chemical compound FC(F)(F)OC1=CC=C(S(Cl)(=O)=O)C=C1 UHCDBMIOLNKDHG-UHFFFAOYSA-N 0.000 description 1
OZDCZHDOIBUGAJ-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=C(S(Cl)(=O)=O)C=C1 OZDCZHDOIBUGAJ-UHFFFAOYSA-N 0.000 description 1
GPKATEXWKFZQRH-UHFFFAOYSA-N 4-[2-(dipropylamino)ethyl]aniline Chemical compound CCCN(CCC)CCC1=CC=C(N)C=C1 GPKATEXWKFZQRH-UHFFFAOYSA-N 0.000 description 1
GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
241000283707 Capra Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
244000248349 Citrus limon Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
208000004117 Congenital Myasthenic Syndromes Diseases 0.000 description 1
102000004980 Dopamine D2 Receptors Human genes 0.000 description 1
108090001111 Dopamine D2 Receptors Proteins 0.000 description 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
PMVSDNDAUGGCCE-TYYBGVCCSA-L Ferrous fumarate Chemical compound [Fe+2].[O-]C(=O)\C=C\C([O-])=O PMVSDNDAUGGCCE-TYYBGVCCSA-L 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
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150000007513 acids Chemical class 0.000 description 1
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036765 blood level Effects 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
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UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
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WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
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239000008176 lyophilized powder Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
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235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 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
IYHSCCCNULJSLJ-UHFFFAOYSA-N tert-butyl 2-(ethylamino)butanoate Chemical compound CCNC(CC)C(=O)OC(C)(C)C IYHSCCCNULJSLJ-UHFFFAOYSA-N 0.000 description 1
UOQRWBOYRPYPAN-UHFFFAOYSA-N tert-butyl 2-[2-(3-aminophenyl)ethylamino]butanoate Chemical compound CC(C)(C)OC(=O)C(CC)NCCC1=CC=CC(N)=C1 UOQRWBOYRPYPAN-UHFFFAOYSA-N 0.000 description 1
UIYOVVYZPVVUMJ-UHFFFAOYSA-N tert-butyl carbamoyl carbonate Chemical compound CC(C)(C)OC(=O)OC(N)=O UIYOVVYZPVVUMJ-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- 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
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—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
- A61P25/22—Anxiolytics
- 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
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- C07C311/21—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 a carbon atom of a six-membered aromatic ring
- 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
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Psychology (AREA)
Pain & Pain Management (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK1624-2000A 1998-05-14 1999-05-07 Fenylsulfónamid-fenyletylamíny užitočné ako dopamínové receptory SK16242000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8549398P	1998-05-14	1998-05-14
PCT/US1999/007023 WO1999058499A1 (en)	1998-05-14	1999-05-07	Phenylsulfonamide-phenylethylamines useful as dopamine receptors

Publications (1)

Publication Number	Publication Date
SK16242000A3 true SK16242000A3 (sk)	2001-06-11

Family

ID=22191975

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1624-2000A SK16242000A3 (sk)	1998-05-14	1999-05-07	Fenylsulfónamid-fenyletylamíny užitočné ako dopamínové receptory

Country Status (24)

Country	Link
US (1)	US6103766A (de)
EP (1)	EP1077935B1 (de)
JP (1)	JP2002514623A (de)
KR (1)	KR20010043546A (de)
CN (1)	CN1152857C (de)
AT (1)	ATE253045T1 (de)
AU (1)	AU752543B2 (de)
BR (1)	BR9910405A (de)
CA (1)	CA2327345A1 (de)
DE (1)	DE69912419T2 (de)
DK (1)	DK1077935T3 (de)
EA (1)	EA002918B1 (de)
ES (1)	ES2211078T3 (de)
HU (1)	HUP0101746A3 (de)
IL (1)	IL139263A0 (de)
NO (1)	NO20005732L (de)
NZ (1)	NZ508152A (de)
PL (1)	PL343891A1 (de)
PT (1)	PT1077935E (de)
SK (1)	SK16242000A3 (de)
TR (1)	TR200003325T2 (de)
TW (1)	TW450954B (de)
WO (1)	WO1999058499A1 (de)
ZA (1)	ZA200005921B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1998038156A1 (en) *	1997-02-27	1998-09-03	Takeda Chemical Industries, Ltd.	Amine compounds, their production and use as amyloid-beta production inhibitors
WO2002089740A2 (en) *	2001-05-07	2002-11-14	Smithkline Beecham Corporation	Sulfonamides
US6849635B2 (en) *	2001-05-07	2005-02-01	Smithkline Beecham Corporation	Sulfonamides
US7851463B2 (en)	2004-10-14	2010-12-14	Abbott Gmbh & Co. Kg	Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor
JP4754570B2 (ja)	2004-10-14	2011-08-24	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ザビシクロヘプチル化合物
EP2371814A1 (de) *	2004-10-14	2011-10-05	Abbott GmbH & Co. KG	Aminoethylaromatische Verbindungen zur Behandlung von Erkrankungen, die auf Dopamin-D3-Rezeptormodulation ansprechen
UY30284A1 (es)	2006-04-14	2007-11-30	Abbott Gmbh & Amp	Compuestos de ariloxietilamina apropiados para tratar trastornos que responden a la modulacion del receptor de dopamina d3
ES2360254T3 (es) *	2006-04-14	2011-06-02	ABBOTT GMBH & CO. KG	Compuestos de ariloxietilamina adecuados para tratamiento de trastornos que respondan a la modulación del receptor de dopamina d3.
TW200812961A (en)	2006-04-19	2008-03-16	Abbott Gmbh & Co Kg	Heterocyclic compounds suitable for treating disorders that respond to modulation of the serotonin 5HT6 receptor
TW200808762A (en)	2006-04-19	2008-02-16	Abbott Gmbh & Co Kg	Heterocyclic compounds suitable for treating disorders that respond to modulation of the serotonin 5HT6 receptor
WO2008026046A1 (en) *	2006-08-30	2008-03-06	Pfizer Products Inc.	Morpholine d3 dopamine antagonists

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3574741A (en) *	1969-04-14	1971-04-13	Mead Johnson & Co	Sulfonamidophenalkylamines
US5451677A (en) *	1993-02-09	1995-09-19	Merck & Co., Inc.	Substituted phenyl sulfonamides as selective β 3 agonists for the treatment of diabetes and obesity
GB9402197D0 (en) *	1994-02-04	1994-03-30	Smithkline Beecham Plc	Compounds
EP0793653A1 (de) *	1994-11-23	1997-09-10	Neurogen Corporation	Einige 4-aminomethyl-2-substituierte imidazolderivate und 2-aminomethyl - 4 - substituierte imidazolderivate; neue klassen von spezifischen liganden des dopaminrezeptorsubtyps
ES2191838T3 (es) *	1996-05-11	2003-09-16	Smithkline Beecham Plc	Derivados de tetrahidroisoquinoleina como moduladores de los receptores d3 de la dopamina.
EP1184370B1 (de) *	1996-07-22	2005-09-14	Novo Nordisk A/S	Verbindungen mit Wachstumshormon-freisetzenden Eigenschaften
JPH1180156A (ja) *	1997-09-04	1999-03-26	Hokuriku Seiyaku Co Ltd	１−（置換アリール）アルキル−１ｈ−イミダゾピリジン−４−アミン誘導体

1999
- 1999-04-26 TW TW088106644A patent/TW450954B/zh not_active IP Right Cessation
- 1999-05-07 AU AU37418/99A patent/AU752543B2/en not_active Ceased
- 1999-05-07 PL PL99343891A patent/PL343891A1/xx unknown
- 1999-05-07 BR BR9910405-9A patent/BR9910405A/pt not_active Application Discontinuation
- 1999-05-07 IL IL13926399A patent/IL139263A0/xx not_active IP Right Cessation
- 1999-05-07 EA EA200001184A patent/EA002918B1/ru not_active IP Right Cessation
- 1999-05-07 US US09/306,748 patent/US6103766A/en not_active Expired - Fee Related
- 1999-05-07 CN CNB998052175A patent/CN1152857C/zh not_active Expired - Fee Related
- 1999-05-07 CA CA002327345A patent/CA2327345A1/en not_active Abandoned
- 1999-05-07 NZ NZ508152A patent/NZ508152A/xx unknown
- 1999-05-07 HU HU0101746A patent/HUP0101746A3/hu unknown
- 1999-05-07 PT PT99919771T patent/PT1077935E/pt unknown
- 1999-05-07 WO PCT/US1999/007023 patent/WO1999058499A1/en not_active Ceased
- 1999-05-07 DE DE69912419T patent/DE69912419T2/de not_active Expired - Fee Related
- 1999-05-07 AT AT99919771T patent/ATE253045T1/de not_active IP Right Cessation
- 1999-05-07 SK SK1624-2000A patent/SK16242000A3/sk unknown
- 1999-05-07 EP EP99919771A patent/EP1077935B1/de not_active Expired - Lifetime
- 1999-05-07 KR KR1020007012661A patent/KR20010043546A/ko not_active Abandoned
- 1999-05-07 TR TR2000/03325T patent/TR200003325T2/xx unknown
- 1999-05-07 ES ES99919771T patent/ES2211078T3/es not_active Expired - Lifetime
- 1999-05-07 JP JP2000548303A patent/JP2002514623A/ja not_active Withdrawn
- 1999-05-07 DK DK99919771T patent/DK1077935T3/da active
2000
- 2000-10-23 ZA ZA200005921A patent/ZA200005921B/en unknown
- 2000-11-13 NO NO20005732A patent/NO20005732L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE69912419D1 (de)	2003-12-04
US6103766A (en)	2000-08-15
HUP0101746A2 (hu)	2002-03-28
IL139263A0 (en)	2001-11-25
DK1077935T3 (da)	2004-02-16
ATE253045T1 (de)	2003-11-15
DE69912419T2 (de)	2004-07-22
AU752543B2 (en)	2002-09-19
PL343891A1 (en)	2001-09-10
ZA200005921B (en)	2001-11-14
PT1077935E (pt)	2004-03-31
EP1077935A1 (de)	2001-02-28
EA002918B1 (ru)	2002-10-31
CN1297431A (zh)	2001-05-30
TR200003325T2 (tr)	2001-04-20
ES2211078T3 (es)	2004-07-01
AU3741899A (en)	1999-11-29
CA2327345A1 (en)	1999-11-18
EA200001184A1 (ru)	2001-04-23
NO20005732D0 (no)	2000-11-13
KR20010043546A (ko)	2001-05-25
EP1077935B1 (de)	2003-10-29
WO1999058499A1 (en)	1999-11-18
NO20005732L (no)	2000-11-13
TW450954B (en)	2001-08-21
HK1036049A1 (en)	2001-12-21
HUP0101746A3 (en)	2002-10-28
NZ508152A (en)	2003-03-28
BR9910405A (pt)	2001-01-09
CN1152857C (zh)	2004-06-09
JP2002514623A (ja)	2002-05-21

Publication	Publication Date	Title
PL166565B1 (pl)	1995-06-30	Sposób wytwarzania nowych pochodnych amin aromatycznych PL PL
RU2089547C1 (ru)	1997-09-10	Производные n-алкиленпиперидина, способ их получения, фармацевтическая композиция на их основе, оптически чистые производные n-алкиленпиперидина
AU657272B2 (en)	1995-03-09	Arylalkylamines, process for preparing them and pharmaceutical compositions containing them
AU2005225632B2 (en)	2011-08-04	Formamide derivatives useful as adrenoceptor
PT763031E (pt)	2000-10-31	Derivados da piperazina como antagonistas 5ht1a
DE3700408A1 (de)	1987-07-09	Indolderivate, sie enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung
PL210131B1 (pl)	2011-12-30	Pochodne sulfonoamidowe, sposób ich wytwarzania, środek farmaceutyczny i zastosowanie tych pochodnych
EP0505376A1 (de)	1992-09-30	Muscarin-rezeptor-antagonisten.
CZ362599A3 (cs)	2000-04-12	Indazolamidové sloučeniny jako serotoninergní přípravky
JPS60239458A (ja)	1985-11-28	新規化合物およびそれを含有する抗不整脈剤医薬組成物
DE3542698A1 (de)	1986-06-05	Indolderivate, verfahren zu ihrer herstellung und sie enthaltende, pharmazeutische zubereitungen
US6103766A (en)	2000-08-15	Phenylsulfonamide-phenylethylamines useful as dopamine receptors
DE69329084T2 (de)	2000-12-21	Benzoxazepin-Derivate als Cholinesterase-Inhibitoren
PL165842B1 (pl)	1995-02-28	Sposób wytwarzania nowych pochodnych heksahydroazepiny PL PL PL PL PL PL
KR20030024919A (ko)	2003-03-26	Ｎ-(3,5-디클로로-2-메톡시페닐)-4-메톡시-3-피페라진-1-일-벤젠술폰아미드
US4652584A (en)	1987-03-24	Acetylenic phenoxypropanol derivatives and pharmaceutical compositions for the treatment of hypertension
US20070099986A1 (en)	2007-05-03	Preventives/remedies for urinary disturbance
EP0443862A1 (de)	1991-08-28	Triaminderivate und deren Säureadditionssalze
CZ20004173A3 (cs)	2001-03-14	Fenylsulfonamid-fenylethylaminy užitečné jako dopaminové receptory
MXPA00011147A (en)	2001-07-31	Phenylsulfonamide-phenylethylamines useful as dopamine receptors
FR2663329A1 (fr)	1991-12-20	Composes aromatiques amines, procede pour leur preparation et compositions pharmaceutiques les contenant.
HK1036049B (en)	2005-03-24	Phenylsulfonamide-phenylethylamines useful as dopamine receptors
JP2005523936A (ja)	2005-08-11	タムスロシン誘導体
FR2654100A1 (fr)	1991-05-10	Arylalkylenediamines, procede pour leur preparation et compositions pharmaceutiques les contenant.
HK1102665A (en)	2007-11-30	Sulfonamide compounds for the treatment of neurodegenerative disorders