ES2264003T3 - Derivados de sulfonamida como agentges antipsicoticos. - Google Patents
Derivados de sulfonamida como agentges antipsicoticos.Info
- Publication number
- ES2264003T3 ES2264003T3 ES03757936T ES03757936T ES2264003T3 ES 2264003 T3 ES2264003 T3 ES 2264003T3 ES 03757936 T ES03757936 T ES 03757936T ES 03757936 T ES03757936 T ES 03757936T ES 2264003 T3 ES2264003 T3 ES 2264003T3
- Authority
- ES
- Spain
- Prior art keywords
- sub
- sup
- alkyl
- tetrahydro
- amide
- 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.)
- Expired - Lifetime
Links
- 229940124530 sulfonamide Drugs 0.000 title description 8
- 150000003456 sulfonamides Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000004429 atom Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- -1 nitro, hydroxy Chemical group 0.000 claims description 69
- 150000001408 amides Chemical class 0.000 claims description 34
- OIPHSFTWQQESBR-UHFFFAOYSA-N 5-(4-chlorophenyl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=C(Cl)C=C1 OIPHSFTWQQESBR-UHFFFAOYSA-N 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 108050004812 Dopamine receptor Proteins 0.000 claims description 5
- 102000015554 Dopamine receptor Human genes 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- FTXXGSMYHRJVCF-UHFFFAOYSA-N 5-(4-fluorophenyl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=C(F)C=C1 FTXXGSMYHRJVCF-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 201000009032 substance abuse Diseases 0.000 claims description 4
- 231100000736 substance abuse Toxicity 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- TWJSWLCWGNKOSV-UHFFFAOYSA-N 5-(1,2-oxazol-3-yl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=NOC=C1 TWJSWLCWGNKOSV-UHFFFAOYSA-N 0.000 claims description 2
- UPDQRDIPQIYFJM-UHFFFAOYSA-N 5-(2,4-difluorophenyl)-n-[7-(dimethylamino)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-8-yl]thiophene-2-sulfonamide Chemical compound CN(C)C1=CC=2CCN(C)CCC=2C=C1NS(=O)(=O)C(S1)=CC=C1C1=CC=C(F)C=C1F UPDQRDIPQIYFJM-UHFFFAOYSA-N 0.000 claims description 2
- IZBREDCPMYVUCR-UHFFFAOYSA-N 5-(2,4-difluorophenyl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=C(F)C=C1F IZBREDCPMYVUCR-UHFFFAOYSA-N 0.000 claims description 2
- RJPWNISLJAWWRX-UHFFFAOYSA-N 5-(3,4-difluorophenyl)-n-[7-(dimethylamino)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-8-yl]thiophene-2-sulfonamide Chemical compound CN(C)C1=CC=2CCN(C)CCC=2C=C1NS(=O)(=O)C(S1)=CC=C1C1=CC=C(F)C(F)=C1 RJPWNISLJAWWRX-UHFFFAOYSA-N 0.000 claims description 2
- UBZXJTSBJNRCQD-UHFFFAOYSA-N 5-(3,4-difluorophenyl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=C(F)C(F)=C1 UBZXJTSBJNRCQD-UHFFFAOYSA-N 0.000 claims description 2
- HLGHFULNLRNZDQ-UHFFFAOYSA-N 5-(3-chlorophenyl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CC(Cl)=C1 HLGHFULNLRNZDQ-UHFFFAOYSA-N 0.000 claims description 2
- ZVMBHUVSYMQPST-UHFFFAOYSA-N 5-(3-fluorophenyl)thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CC(F)=C1 ZVMBHUVSYMQPST-UHFFFAOYSA-N 0.000 claims description 2
- YFJUWJSFDBTDJL-UHFFFAOYSA-N 5-(3-methoxyphenyl)thiophene-2-sulfonic acid Chemical compound COC1=CC=CC(C=2SC(=CC=2)S(O)(=O)=O)=C1 YFJUWJSFDBTDJL-UHFFFAOYSA-N 0.000 claims description 2
- QKEZDQKIPSHHEJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[7-(dimethylamino)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-8-yl]thiophene-2-sulfonamide Chemical compound CN(C)C1=CC=2CCN(C)CCC=2C=C1NS(=O)(=O)C(S1)=CC=C1C1=CC=C(Cl)C=C1 QKEZDQKIPSHHEJ-UHFFFAOYSA-N 0.000 claims description 2
- SZHOFKSNJARCML-UHFFFAOYSA-N 5-(4-methoxyphenyl)thiophene-2-sulfonic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(O)(=O)=O)S1 SZHOFKSNJARCML-UHFFFAOYSA-N 0.000 claims description 2
- MBPOHUCKZRTDGC-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 MBPOHUCKZRTDGC-UHFFFAOYSA-N 0.000 claims description 2
- ZPZKRWFSISJSQH-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]thiophene-2-sulfonic acid Chemical compound S1C(S(=O)(=O)O)=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZPZKRWFSISJSQH-UHFFFAOYSA-N 0.000 claims description 2
- CKMJGQQJLDFUBV-UHFFFAOYSA-N n-[7-(dimethylamino)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-8-yl]-5-(4-fluorophenyl)thiophene-2-sulfonamide Chemical compound CN(C)C1=CC=2CCN(C)CCC=2C=C1NS(=O)(=O)C(S1)=CC=C1C1=CC=C(F)C=C1 CKMJGQQJLDFUBV-UHFFFAOYSA-N 0.000 claims description 2
- SXASRKQBYKOCPP-UHFFFAOYSA-N 5-(4-chloro-2-methylphenyl)thiophene-2-sulfonic acid Chemical compound CC1=CC(Cl)=CC=C1C1=CC=C(S(O)(=O)=O)S1 SXASRKQBYKOCPP-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 9
- 239000000164 antipsychotic agent Substances 0.000 abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 abstract 3
- RFUAYXROQMBXQN-UHFFFAOYSA-N 7-(benzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C=1C=C2CCNCC2=CC=1S(=O)(=O)C1=CC=CC=C1 RFUAYXROQMBXQN-UHFFFAOYSA-N 0.000 abstract 1
- UZZCRYZXXODAKU-UHFFFAOYSA-N 7-(benzenesulfonyl)-1,2,3,4-tetrahydroisoquinoline;hydrochloride Chemical compound Cl.C=1C=C2CCNCC2=CC=1S(=O)(=O)C1=CC=CC=C1 UZZCRYZXXODAKU-UHFFFAOYSA-N 0.000 abstract 1
- IGVZBVVFJNXNFL-UHFFFAOYSA-N 7-(benzenesulfonyl)-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-8-ol Chemical compound C1=C2CCN(C)CCC2=CC(O)=C1S(=O)(=O)C1=CC=CC=C1 IGVZBVVFJNXNFL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 238000000034 method Methods 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 102000005962 receptors Human genes 0.000 description 13
- 108020003175 receptors Proteins 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 239000003981 vehicle Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000027455 binding Effects 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- ALRAQONDZUQFOP-UHFFFAOYSA-N 7-amino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid Chemical compound C1CN(C(O)=O)CCC2=CC(N)=CC=C21 ALRAQONDZUQFOP-UHFFFAOYSA-N 0.000 description 5
- FTMFRXMZHMLVGD-UHFFFAOYSA-N 8-amino-7-methoxy-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid Chemical compound C1CN(C(O)=O)CCC2=C1C=C(OC)C(N)=C2 FTMFRXMZHMLVGD-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229940076279 serotonin Drugs 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 108091005435 5-HT6 receptors Proteins 0.000 description 3
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 102000004073 Dopamine D3 Receptors Human genes 0.000 description 3
- 108090000525 Dopamine D3 Receptors Proteins 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- 208000028017 Psychotic disease Diseases 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- CISMAMHQCOJHQS-UHFFFAOYSA-N tert-butyl 5-[(5-bromothiophen-2-yl)sulfonylamino]-5-(dimethylamino)-2,4-dihydro-1h-3-benzazepine-3-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=CC=CC=C2C1(N(C)C)NS(=O)(=O)C1=CC=C(Br)S1 CISMAMHQCOJHQS-UHFFFAOYSA-N 0.000 description 3
- YSWFGFXKRFXHHO-UHFFFAOYSA-N tert-butyl 5-amino-5-(dimethylamino)-2,4-dihydro-1h-3-benzazepine-3-carboxylate Chemical compound CN(C)C1(N)CN(C(=O)OC(C)(C)C)CCC2=CC=CC=C12 YSWFGFXKRFXHHO-UHFFFAOYSA-N 0.000 description 3
- GFXILVCKTUAYRJ-UHFFFAOYSA-N tert-butyl 7-[(5-bromothiophen-2-yl)sulfonylamino]-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylate Chemical compound C1=C2CCN(C(=O)OC(C)(C)C)CCC2=CC=C1NS(=O)(=O)C1=CC=C(Br)S1 GFXILVCKTUAYRJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical class N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- TXJXCXSFIVCGDS-UHFFFAOYSA-N 34583-83-0 Chemical compound C1CNCCC2=CC([N+](=O)[O-])=CC=C21 TXJXCXSFIVCGDS-UHFFFAOYSA-N 0.000 description 2
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 2
- 102100024959 5-hydroxytryptamine receptor 2C Human genes 0.000 description 2
- 102100040368 5-hydroxytryptamine receptor 6 Human genes 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 208000024714 major depressive disease Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005495 pyridazyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- HFNHAPQMXICKCF-USJMABIRSA-N urotensin-ii Chemical compound N([C@@H](CC(O)=O)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@@H](C(C)C)C(O)=O)C(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@@H](N)CCC(O)=O)[C@@H](C)O HFNHAPQMXICKCF-USJMABIRSA-N 0.000 description 1
- 231100000889 vertigo Toxicity 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/18—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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0223226 | 2002-10-07 | ||
| GB0223226A GB0223226D0 (en) | 2002-10-07 | 2002-10-07 | Compounds |
| GB0223236 | 2002-10-07 | ||
| GB0223236A GB0223236D0 (en) | 2002-10-07 | 2002-10-07 | Compouds |
| GB0314627A GB0314627D0 (en) | 2003-06-23 | 2003-06-23 | Novel compounds |
| GB0314627 | 2003-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2264003T3 true ES2264003T3 (es) | 2006-12-16 |
Family
ID=32073912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03757936T Expired - Lifetime ES2264003T3 (es) | 2002-10-07 | 2003-10-06 | Derivados de sulfonamida como agentges antipsicoticos. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7122538B2 (https=) |
| EP (1) | EP1549639B1 (https=) |
| JP (1) | JP2006504794A (https=) |
| AT (1) | ATE327234T1 (https=) |
| AU (1) | AU2003273969A1 (https=) |
| DE (1) | DE60305519T2 (https=) |
| ES (1) | ES2264003T3 (https=) |
| WO (1) | WO2004031181A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005058328A1 (en) * | 2003-12-18 | 2005-06-30 | Abbott Gmbh & Co. Kg | Tetrahydrobenzazepines and their use in the modulation of the dopamine d3 receptor |
| US20050137186A1 (en) * | 2003-12-18 | 2005-06-23 | Abbott Gmbh & Co. Kg. | Tetrahydrobenzazepines and their use |
| WO2007022933A1 (en) * | 2005-08-22 | 2007-03-01 | Glaxo Group Limited | Triazole derivatives as modulators of dopamine d3 receptors |
| EP1837332A1 (en) * | 2006-03-23 | 2007-09-26 | Laboratorios Del Dr. Esteve, S.A. | Substituted tetrahydroisoquinoline compounds, their preparation and use in medicaments |
| WO2007140213A1 (en) | 2006-05-26 | 2007-12-06 | Forest Laboratories Holdings Limited | Pyridoazepine derivatives |
| US20070293475A1 (en) * | 2006-06-20 | 2007-12-20 | Alcon Manufacturing Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| SG11201906289YA (en) * | 2017-01-13 | 2019-08-27 | Sumitomo Dainippon Pharma Co Ltd | Therapeutic agent for non-motor symptoms associated with parkinson's disease |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA792785B (en) * | 1978-07-07 | 1980-08-27 | Smithkline Corp | Mercapto substituted-2,3,4,5-tetrahydro-1h-3-benzazepines |
| GB9926302D0 (en) | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
| WO2001045694A1 (en) * | 1999-12-21 | 2001-06-28 | Smithkline Beecham Corporation | Urotensin-ii receptor antagonists |
| DE10053799A1 (de) | 2000-10-30 | 2002-05-08 | Bayer Ag | Verwendung von Tetrahydroisochinolinsulfonamiden |
| KR20040081201A (ko) * | 2002-02-13 | 2004-09-20 | 글락소 그룹 리미티드 | 항정신병제로서 벤젠술폰아미드 유도체 |
-
2003
- 2003-10-06 DE DE60305519T patent/DE60305519T2/de not_active Expired - Fee Related
- 2003-10-06 ES ES03757936T patent/ES2264003T3/es not_active Expired - Lifetime
- 2003-10-06 WO PCT/EP2003/011174 patent/WO2004031181A1/en not_active Ceased
- 2003-10-06 AT AT03757936T patent/ATE327234T1/de not_active IP Right Cessation
- 2003-10-06 AU AU2003273969A patent/AU2003273969A1/en not_active Abandoned
- 2003-10-06 US US10/530,538 patent/US7122538B2/en not_active Expired - Fee Related
- 2003-10-06 JP JP2005500032A patent/JP2006504794A/ja active Pending
- 2003-10-06 EP EP03757936A patent/EP1549639B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1549639A1 (en) | 2005-07-06 |
| WO2004031181A1 (en) | 2004-04-15 |
| ATE327234T1 (de) | 2006-06-15 |
| AU2003273969A1 (en) | 2004-04-23 |
| EP1549639B1 (en) | 2006-05-24 |
| US20060063757A1 (en) | 2006-03-23 |
| DE60305519D1 (de) | 2006-06-29 |
| DE60305519T2 (de) | 2006-11-23 |
| US7122538B2 (en) | 2006-10-17 |
| JP2006504794A (ja) | 2006-02-09 |
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