ZA200005921B - Phenylsulfonamide-phenylethylamines useful as dopamine receptors. - Google Patents
Phenylsulfonamide-phenylethylamines useful as dopamine receptors. Download PDFInfo
- Publication number
- ZA200005921B ZA200005921B ZA200005921A ZA200005921A ZA200005921B ZA 200005921 B ZA200005921 B ZA 200005921B ZA 200005921 A ZA200005921 A ZA 200005921A ZA 200005921 A ZA200005921 A ZA 200005921A ZA 200005921 B ZA200005921 B ZA 200005921B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- ethyl
- propylamine
- substance
- composition
- Prior art date
Links
- 108050004812 Dopamine receptor Proteins 0.000 title description 2
- 102000015554 Dopamine receptor Human genes 0.000 title description 2
- 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 1
- 150000001875 compounds Chemical class 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 36
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- -1 4-trifluoromethoxybenzenesulfonamido Chemical group 0.000 claims description 8
- 102000004073 Dopamine D3 Receptors Human genes 0.000 claims description 7
- 108090000525 Dopamine D3 Receptors Proteins 0.000 claims description 7
- 208000015114 central nervous system disease Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 1
- 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 1
- 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 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- 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
- 239000003921 oil Substances 0.000 description 15
- 235000019198 oils Nutrition 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- IOXOZOPLBFXYLM-UHFFFAOYSA-N 2-(4-nitrophenyl)ethanamine Chemical compound NCCC1=CC=C([N+]([O-])=O)C=C1 IOXOZOPLBFXYLM-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 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 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 201000000980 schizophrenia Diseases 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- 239000003826 tablet Substances 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
- PWZWTSYUZQZFKE-UHFFFAOYSA-N 2-(3-nitrophenyl)ethanol Chemical compound OCCC1=CC=CC([N+]([O-])=O)=C1 PWZWTSYUZQZFKE-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 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 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
- 241000220479 Acacia Species 0.000 description 2
- 208000017164 Chronobiology disease Diseases 0.000 description 2
- 206010012289 Dementia Diseases 0.000 description 2
- 206010013654 Drug abuse Diseases 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 206010026749 Mania Diseases 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 2
- 239000008135 aqueous vehicle Substances 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 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
- 238000010511 deprotection reaction Methods 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 206010013663 drug dependence Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000008024 pharmaceutical diluent Substances 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
- 208000019116 sleep disease Diseases 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- UIYOVVYZPVVUMJ-UHFFFAOYSA-N tert-butyl carbamoyl carbonate Chemical compound CC(C)(C)OC(=O)OC(N)=O UIYOVVYZPVVUMJ-UHFFFAOYSA-N 0.000 description 2
- 239000003981 vehicle 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
- 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
- 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 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
- HKJUOMPYMPXLFS-UHFFFAOYSA-N 4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodobenzoic acid Chemical compound IC1=CC(C(=O)O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 HKJUOMPYMPXLFS-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
- 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
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 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
- 239000003708 ampul Substances 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical class CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 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
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 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
- 230000001225 therapeutic effect Effects 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8549398P | 1998-05-14 | 1998-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200005921B true ZA200005921B (en) | 2001-11-14 |
Family
ID=22191975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200005921A ZA200005921B (en) | 1998-05-14 | 2000-10-23 | Phenylsulfonamide-phenylethylamines useful as dopamine receptors. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6103766A (zh) |
| EP (1) | EP1077935B1 (zh) |
| JP (1) | JP2002514623A (zh) |
| KR (1) | KR20010043546A (zh) |
| CN (1) | CN1152857C (zh) |
| AT (1) | ATE253045T1 (zh) |
| AU (1) | AU752543B2 (zh) |
| BR (1) | BR9910405A (zh) |
| CA (1) | CA2327345A1 (zh) |
| DE (1) | DE69912419T2 (zh) |
| DK (1) | DK1077935T3 (zh) |
| EA (1) | EA002918B1 (zh) |
| ES (1) | ES2211078T3 (zh) |
| HK (1) | HK1036049A1 (zh) |
| HU (1) | HUP0101746A3 (zh) |
| IL (1) | IL139263A0 (zh) |
| NO (1) | NO20005732L (zh) |
| NZ (1) | NZ508152A (zh) |
| PL (1) | PL343891A1 (zh) |
| PT (1) | PT1077935E (zh) |
| SK (1) | SK16242000A3 (zh) |
| TR (1) | TR200003325T2 (zh) |
| TW (1) | TW450954B (zh) |
| WO (1) | WO1999058499A1 (zh) |
| ZA (1) | ZA200005921B (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT971878E (pt) * | 1997-02-27 | 2008-07-08 | Takeda Pharmaceutical | Compostos de amina, sua produção e utilização como inibidores da produção de amilóide beta |
| JP2004535390A (ja) * | 2001-05-07 | 2004-11-25 | スミスクライン・ビーチャム・コーポレイション | スルホンアミド |
| US20050043536A1 (en) * | 2001-05-07 | 2005-02-24 | Dashyant Dhanak | Sulfonamides |
| WO2006040179A1 (en) * | 2004-10-14 | 2006-04-20 | Abbott Gmbh & Co. Kg | Aminoethylaromatic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor |
| WO2006040182A1 (en) | 2004-10-14 | 2006-04-20 | Abbott Gmbh & Co. Kg | Heterocyclic compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor |
| WO2006040176A1 (en) | 2004-10-14 | 2006-04-20 | Abbott Gmbh & Co. Kg | Azabicycloheptyl compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor |
| EP2013179B1 (en) | 2006-04-14 | 2011-01-19 | Abbott GmbH & Co. KG | Aryloxyethylamine compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor |
| 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. |
| US8642642B2 (en) | 2006-04-19 | 2014-02-04 | Abbott Laboratories | Heterocyclic arylsulphones 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)
| 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 |
| AU4368996A (en) * | 1994-11-23 | 1996-06-17 | Neurogen Corporation | Certain 4-aminomethyl-2-substituted imidazole derivatives and 2-aminomethyl-4-substituted imidazole derivatives; new classes of dopamine receptor subtype specific ligands |
| ATE232850T1 (de) * | 1996-05-11 | 2003-03-15 | Smithkline Beecham Plc | Tetrahydroisoquinoline derivate als modulatoren von dopamine d3 rezeptoren |
| DE69734215T2 (de) * | 1996-07-22 | 2006-06-29 | 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 KR KR1020007012661A patent/KR20010043546A/ko active IP Right Grant
- 1999-05-07 AU AU37418/99A patent/AU752543B2/en not_active Ceased
- 1999-05-07 NZ NZ508152A patent/NZ508152A/xx unknown
- 1999-05-07 HU HU0101746A patent/HUP0101746A3/hu unknown
- 1999-05-07 EP EP99919771A patent/EP1077935B1/en not_active Expired - Lifetime
- 1999-05-07 TR TR2000/03325T patent/TR200003325T2/xx unknown
- 1999-05-07 CN CNB998052175A patent/CN1152857C/zh not_active Expired - Fee Related
- 1999-05-07 EA EA200001184A patent/EA002918B1/ru not_active IP Right Cessation
- 1999-05-07 CA CA002327345A patent/CA2327345A1/en not_active Abandoned
- 1999-05-07 DE DE69912419T patent/DE69912419T2/de not_active Expired - Fee Related
- 1999-05-07 DK DK99919771T patent/DK1077935T3/da active
- 1999-05-07 PL PL99343891A patent/PL343891A1/xx unknown
- 1999-05-07 JP JP2000548303A patent/JP2002514623A/ja not_active Withdrawn
- 1999-05-07 IL IL13926399A patent/IL139263A0/xx not_active IP Right Cessation
- 1999-05-07 PT PT99919771T patent/PT1077935E/pt unknown
- 1999-05-07 BR BR9910405-9A patent/BR9910405A/pt not_active Application Discontinuation
- 1999-05-07 SK SK1624-2000A patent/SK16242000A3/sk unknown
- 1999-05-07 AT AT99919771T patent/ATE253045T1/de not_active IP Right Cessation
- 1999-05-07 WO PCT/US1999/007023 patent/WO1999058499A1/en active IP Right Grant
- 1999-05-07 US US09/306,748 patent/US6103766A/en not_active Expired - Fee Related
- 1999-05-07 ES ES99919771T patent/ES2211078T3/es not_active Expired - Lifetime
-
2000
- 2000-10-23 ZA ZA200005921A patent/ZA200005921B/en unknown
- 2000-11-13 NO NO20005732A patent/NO20005732L/no not_active Application Discontinuation
-
2001
- 2001-09-20 HK HK01106645A patent/HK1036049A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69912419T2 (de) | 2004-07-22 |
| US6103766A (en) | 2000-08-15 |
| AU3741899A (en) | 1999-11-29 |
| BR9910405A (pt) | 2001-01-09 |
| NO20005732D0 (no) | 2000-11-13 |
| JP2002514623A (ja) | 2002-05-21 |
| CN1297431A (zh) | 2001-05-30 |
| CA2327345A1 (en) | 1999-11-18 |
| PT1077935E (pt) | 2004-03-31 |
| NO20005732L (no) | 2000-11-13 |
| EP1077935A1 (en) | 2001-02-28 |
| SK16242000A3 (sk) | 2001-06-11 |
| KR20010043546A (ko) | 2001-05-25 |
| HUP0101746A2 (hu) | 2002-03-28 |
| HK1036049A1 (en) | 2001-12-21 |
| AU752543B2 (en) | 2002-09-19 |
| CN1152857C (zh) | 2004-06-09 |
| HUP0101746A3 (en) | 2002-10-28 |
| DK1077935T3 (da) | 2004-02-16 |
| EP1077935B1 (en) | 2003-10-29 |
| DE69912419D1 (de) | 2003-12-04 |
| PL343891A1 (en) | 2001-09-10 |
| TW450954B (en) | 2001-08-21 |
| ES2211078T3 (es) | 2004-07-01 |
| ATE253045T1 (de) | 2003-11-15 |
| IL139263A0 (en) | 2001-11-25 |
| TR200003325T2 (tr) | 2001-04-20 |
| NZ508152A (en) | 2003-03-28 |
| EA002918B1 (ru) | 2002-10-31 |
| WO1999058499A1 (en) | 1999-11-18 |
| EA200001184A1 (ru) | 2001-04-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8242118B2 (en) | Arylsulfonamide derivatives for use as CCR3 antagonists in the treatment of inflammatory and immunological disorders | |
| RU2114111C1 (ru) | 4-пиримидин- или пиридинильные производные индол-3-ил-алкилпиперазинов, фармацевтическая композиция | |
| US7084167B2 (en) | Calcium receptor active molecules and method for preparing same | |
| PL166582B1 (pl) | Sposób wytwarzania nowych pochodnych amin aromatycznych PL PL | |
| WO2003029199A9 (fr) | Derives de benzene et procede de preparation et d'utilisation associe | |
| JP2008518889A (ja) | 新規ブラジキニンｂ１アンタゴニスト、それらの製造方法及び薬物としてのそれらの使用 | |
| AU7235194A (en) | Piperazine compounds used in therapy | |
| US6103766A (en) | Phenylsulfonamide-phenylethylamines useful as dopamine receptors | |
| JP2004505949A (ja) | Ｃａｓｒ調節活性を有する新規ジアミン | |
| PT91417B (pt) | Processo para a preparacao de derivados indolicos | |
| TW200821299A (en) | Sulfonylpyrazole and sulfonylpyrazoline carboxamidine derivatives as 5-HT6 antagonists | |
| WO2002018333A1 (en) | Phenoxybenzylamine derivatives as selective serotonin re-uptake inhibitors | |
| JP2006111553A (ja) | スルホニルオキシインドール誘導体及びそれを含有する医薬組成物 | |
| PL195957B1 (pl) | 2-(3,5-Bis-trifluorometylofenylo)-N-metylo-N-(6-morfolin-4-ylo-4-o-tolilo-pirydyn-3-ylo)-izobutyramid, sposób jego wytwarzania i jego zastosowanie oraz lek zawierający ten związek | |
| EP1778641A1 (en) | 5-ht7 receptor antagonists | |
| BRPI0608523A2 (pt) | composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, métodos para inibir receptor de histamina h3 em um mamìfero, para tratar ou prevenir um distúrbio do sistema nervoso, para tratar ou prevenir obesidade e para tratar ou prevenir um distúrbio ou doença, e, uso de um composto ou um sal do mesmo | |
| PT94070A (pt) | Processo para a preparacao de derivados de piperazina | |
| PT594001E (pt) | Pirazolo¬4,3-c|piridinas processo para a sua preparacao e sua utilizacao como inibidores da reabsorcao de serotonina | |
| TW200800913A (en) | Azinyl-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands | |
| EA029030B1 (ru) | Пептидилнитрильные соединения в качестве ингибиторов дипептидилпептидазы i | |
| US5472966A (en) | Antidepressant heteroarylaminoalkyl derivatives of naphthyl-monazines | |
| US9359337B2 (en) | Acetamide derivatives | |
| MXPA00011147A (en) | Phenylsulfonamide-phenylethylamines useful as dopamine receptors | |
| JP2022551156A (ja) | 疼痛に対する多様な活性を有するホモピペラジニル及びホモピペリジニルキナゾリン－４（３ｈ）－オン誘導体 | |
| CZ20004173A3 (cs) | Fenylsulfonamid-fenylethylaminy užitečné jako dopaminové receptory |