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
- 101710150235 5-hydroxytryptamine receptor 6 Proteins 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 101150049660 DRD2 gene Proteins 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000004479 aerosol dispenser Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000561 anti-psychotic effect Effects 0.000 description 2
- 229940005529 antipsychotics Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 208000010877 cognitive disease Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 239000007937 lozenge 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
- 239000000463 material Substances 0.000 description 2
- 239000003176 neuroleptic agent Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 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 2
- SKMJBOKCXQKYCX-UHFFFAOYSA-N tert-butyl 5-[[5-(4-chlorophenyl)thiophen-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)C(S1)=CC=C1C1=CC=C(Cl)C=C1 SKMJBOKCXQKYCX-UHFFFAOYSA-N 0.000 description 2
- ARNGAICPLMKBHO-UHFFFAOYSA-N tert-butyl 7-nitro-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC2=CC=C([N+]([O-])=O)C=C21 ARNGAICPLMKBHO-UHFFFAOYSA-N 0.000 description 2
- DOXISTIRJKWLCC-UHFFFAOYSA-N tert-butyl 8-[[5-(4-chlorophenyl)thiophen-2-yl]sulfonylamino]-7-methoxy-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylate Chemical compound COC1=CC=2CCN(C(=O)OC(C)(C)C)CCC=2C=C1NS(=O)(=O)C(S1)=CC=C1C1=CC=C(Cl)C=C1 DOXISTIRJKWLCC-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 101710138093 5-hydroxytryptamine receptor 2C Proteins 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- KEUWBUFWYYGWOU-UHFFFAOYSA-N 7-hydroxy-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid Chemical compound C1CN(C(=O)O)CCC2=CC=C(O)C=C21 KEUWBUFWYYGWOU-UHFFFAOYSA-N 0.000 description 1
- YLAVVQVRYOPMMI-UHFFFAOYSA-N 7-methoxy-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid Chemical compound C1CN(C(O)=O)CCC2=CC(OC)=CC=C21 YLAVVQVRYOPMMI-UHFFFAOYSA-N 0.000 description 1
- VWLWWBQMNIAARP-UHFFFAOYSA-N 7-methoxy-2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC(OC)=CC=C21 VWLWWBQMNIAARP-UHFFFAOYSA-N 0.000 description 1
- TZHLGBMSLAYRCH-UHFFFAOYSA-N 7-methoxy-8-nitro-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid Chemical compound C1CN(C(O)=O)CCC2=C1C=C(OC)C([N+]([O-])=O)=C2 TZHLGBMSLAYRCH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 206010003805 Autism Diseases 0.000 description 1
- 208000020706 Autistic disease Diseases 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000017164 Chronobiology disease Diseases 0.000 description 1
- 208000022497 Cocaine-Related disease Diseases 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 101150104779 HTR2A gene Proteins 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- 208000003698 Heroin Dependence Diseases 0.000 description 1
- 101150013372 Htr2c gene Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-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
- 206010026749 Mania Diseases 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 208000027099 Paranoid disease Diseases 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 201000001880 Sexual dysfunction Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 206010043903 Tobacco abuse Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 102000050488 Urotensin II Human genes 0.000 description 1
- 108010018369 Urotensin II Proteins 0.000 description 1
- 208000012886 Vertigo Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 238000009098 adjuvant therapy Methods 0.000 description 1
- 230000016571 aggressive behavior Effects 0.000 description 1
- 206010001584 alcohol abuse Diseases 0.000 description 1
- 208000025746 alcohol use disease Diseases 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 230000006986 amnesia Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical compound O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- AFYNADDZULBEJA-UHFFFAOYSA-N bicinchoninic acid Chemical compound C1=CC=CC2=NC(C=3C=C(C4=CC=CC=C4N=3)C(=O)O)=CC(C(O)=O)=C21 AFYNADDZULBEJA-UHFFFAOYSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000006143 cell culture medium Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000005957 chlorosulfonylation reaction Methods 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 201000001272 cocaine abuse Diseases 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229960002069 diamorphine Drugs 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940052760 dopamine agonists Drugs 0.000 description 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 230000000142 dyskinetic effect Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011536 extraction buffer Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000030135 gastric motility Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000012135 ice-cold extraction buffer Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 108010024941 iodothyronine deiodinase type II Proteins 0.000 description 1
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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 |
|---|---|---|---|
| GB0223236A GB0223236D0 (en) | 2002-10-07 | 2002-10-07 | Compouds |
| GB0223226 | 2002-10-07 | ||
| GB0223226A GB0223226D0 (en) | 2002-10-07 | 2002-10-07 | Compounds |
| GB0223236 | 2002-10-07 | ||
| 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 (enExample) |
| EP (1) | EP1549639B1 (enExample) |
| JP (1) | JP2006504794A (enExample) |
| AT (1) | ATE327234T1 (enExample) |
| AU (1) | AU2003273969A1 (enExample) |
| DE (1) | DE60305519T2 (enExample) |
| ES (1) | ES2264003T3 (enExample) |
| WO (1) | WO2004031181A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1694334B1 (en) * | 2003-12-18 | 2011-10-19 | 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 |
| JP5237807B2 (ja) * | 2005-08-22 | 2013-07-17 | グラクソ グループ リミテッド | ドーパミンｄ３受容体の調節因子としてのトリアゾール誘導体 |
| 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 |
| WO2007149728A2 (en) * | 2006-06-20 | 2007-12-27 | Alcon Research, Ltd. | Aryl and heteroaryl tetrahydrobenzazepine derivatives and their use for treating glaucoma |
| US11576897B2 (en) * | 2017-01-13 | 2023-02-14 | Sumitomo 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 |
| AU2441801A (en) * | 1999-12-21 | 2001-07-03 | Smithkline Beecham Corporation | Urotensin-ii receptor antagonists |
| DE10053799A1 (de) | 2000-10-30 | 2002-05-08 | Bayer Ag | Verwendung von Tetrahydroisochinolinsulfonamiden |
| AU2003215558A1 (en) | 2002-02-13 | 2003-09-04 | Glaxo Group Limited | Benzenesulfonamide derivatives as antipsychotic agents |
-
2003
- 2003-10-06 AT AT03757936T patent/ATE327234T1/de not_active IP Right Cessation
- 2003-10-06 EP EP03757936A patent/EP1549639B1/en not_active Expired - Lifetime
- 2003-10-06 DE DE60305519T patent/DE60305519T2/de not_active Expired - Fee Related
- 2003-10-06 WO PCT/EP2003/011174 patent/WO2004031181A1/en not_active Ceased
- 2003-10-06 JP JP2005500032A patent/JP2006504794A/ja active Pending
- 2003-10-06 ES ES03757936T patent/ES2264003T3/es not_active Expired - Lifetime
- 2003-10-06 US US10/530,538 patent/US7122538B2/en not_active Expired - Fee Related
- 2003-10-06 AU AU2003273969A patent/AU2003273969A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US7122538B2 (en) | 2006-10-17 |
| US20060063757A1 (en) | 2006-03-23 |
| ATE327234T1 (de) | 2006-06-15 |
| EP1549639B1 (en) | 2006-05-24 |
| JP2006504794A (ja) | 2006-02-09 |
| DE60305519T2 (de) | 2006-11-23 |
| AU2003273969A1 (en) | 2004-04-23 |
| EP1549639A1 (en) | 2005-07-06 |
| DE60305519D1 (de) | 2006-06-29 |
| WO2004031181A1 (en) | 2004-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2298294T3 (es) | Derivados de tetrahidrobenzazepina utiles como modulares de los receptores d3 de dopamina (agentes antipsicoticos). | |
| ES2244082T3 (es) | Derivados de sulfonamida que son antagonistas del receptor 5-ht6 y procedimiento para su preparacion. | |
| ES2466641T3 (es) | 2,3,4,5-Tetrahidro-1H-benzo[d]azepinas 6-sustituidas como agonistas del receptor 5-HT2C | |
| ES2203831T3 (es) | Derivados de sulfonamida, procedimiento para su preparacion, y su uso como medicamentos. | |
| ES2255311T3 (es) | Derivados de tetrahidrobenzazepina utiles como moduladores de los receptores d3 de dopamina (agentes anti-psicoticos). | |
| TWI323255B (en) | N-[(1,5-diphenyl-1h-pyrazol-3-yl)methyl]sulfonamide derivatives, preparation and therapeutic application thereof | |
| MXPA04007920A (es) | Derivados de bencensulfonamida como agentes antisicoticos. | |
| WO2003011872A1 (en) | Platelet adp receptor inhibitors | |
| CZ198196A3 (en) | Bicyclic fibrinogen antagonists | |
| JP2005518414A (ja) | ドーパミン受容体のモジュレーターとしての７−スルホニル−３−ベンゾアゼピン誘導体およびｃｎｓ障害の治療のためのその使用 | |
| ES2279965T3 (es) | Sulfonas aromaticas y su uso medico. | |
| ES2333720T3 (es) | Derivados de fenilsulfona y su uso en el tratamiento de trastornos del snc. | |
| CN101600701A (zh) | 芳基磺酰胺衍生物和其使用方法 | |
| ES2264003T3 (es) | Derivados de sulfonamida como agentges antipsicoticos. | |
| ES2246721B1 (es) | Compuestos indolicos sustituidos, su preparacion y su uso como medicamentos. | |
| CN101384549B (zh) | 吡咯衍生物或其盐 | |
| ES2313002T3 (es) | Uso de derivados de sulfonamida para la fabricacion de un medicamento para la profilaxis y/o tratamiento de la ingestion de alimentos. | |
| US20050085461A1 (en) | Benzenesulfonamide derivatives | |
| BRPI0718520A2 (pt) | Composto, métodos para a modulação do receptor de adenosina a1 e para o tratamento de condições mediadas pelo receptor de adenosina a1 em mamíferos, composição farmacêutica, e, usos de uma composição e de um composto | |
| WO2012053630A1 (ja) | 変異アンドロゲン受容体拮抗薬 | |
| ES2342083T3 (es) | 3-piperidinilisocroman-5-oles como agonistas de dopamina. | |
| US20070043026A1 (en) | Dopamine receptor modulators as antipsychotic agents | |
| JP2005531580A (ja) | 抗精神病薬としての７−フェニルスルホニル−テトラヒドロ−３−ベンゾアゼピン誘導体 | |
| JP2007512285A (ja) | 抗精神病薬としての７−［４−（４−クロロベンジルオキシ）ベンゼンスルホニル］−８−メトキシ−３−メチル−２，３，４，５−テトラヒドロ−１ｈ−３−ベンゾアゼピニウムマレエートもしくはトシレート | |
| ES2240737T3 (es) | Derivados de piperazina y su uso como ligandos de 5-ht1b. |