OA12536A - Benzothiophene derivative compounds, process of preparation and use thereof. - Google Patents

Benzothiophene derivative compounds, process of preparation and use thereof. Download PDF

Info

Publication number: OA12536A
Authority: OA; OAPI
Prior art keywords: thiophen; piperazin; propan; compound; benzo
Prior art date: 2000-11-29

Application number

OA1200300144A

Other languages

English (en)

Inventor

Juan Carlos Del Castillo Nieto

Joaquin Del Rio Zambrana

Berta Esperanza Lasheras Aldaz

Antonio Monge Vega

Marisabel Mourelle Mancini

Original Assignee

Vita Lab

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

2000-11-29

Filing date

2001-11-19

Publication date

2006-06-05

2001-11-19 Application filed by Vita Lab filed Critical Vita Lab

2006-06-05 Publication of OA12536A publication Critical patent/OA12536A/en

Links

238000000034 method Methods 0.000 title claims description 39
230000008569 process Effects 0.000 title claims description 12
HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical class COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 49
238000004519 manufacturing process Methods 0.000 claims abstract description 8
239000003772 serotonin uptake inhibitor Substances 0.000 claims abstract description 8
208000012902 Nervous system disease Diseases 0.000 claims abstract description 6
208000025966 Neurological disease Diseases 0.000 claims abstract description 6
239000003814 drug Substances 0.000 claims abstract description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 64
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
-1 -OR Chemical group 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
235000019441 ethanol Nutrition 0.000 claims description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
230000003287 optical effect Effects 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
208000019901 Anxiety disease Diseases 0.000 claims description 4
230000036506 anxiety Effects 0.000 claims description 4
239000003638 chemical reducing agent Substances 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
101100391181 Dictyostelium discoideum forH gene Proteins 0.000 claims description 3
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
206010033664 Panic attack Diseases 0.000 claims description 3
208000028017 Psychotic disease Diseases 0.000 claims description 3
239000000556 agonist Substances 0.000 claims description 3
150000001298 alcohols Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
208000019906 panic disease Diseases 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000012279 sodium borohydride Substances 0.000 claims description 3
229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
125000003158 alcohol group Chemical group 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
229940043279 diisopropylamine Drugs 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims 2
229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 2
239000003420 antiserotonin agent Substances 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 abstract description 15
239000000203 mixture Substances 0.000 abstract description 6
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 abstract description 2
101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 abstract description 2
239000000047 product Substances 0.000 description 42
150000002576 ketones Chemical class 0.000 description 33
238000005481 NMR spectroscopy Methods 0.000 description 30
238000005160 1H NMR spectroscopy Methods 0.000 description 26
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
101150041968 CDC13 gene Proteins 0.000 description 11
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
108020003175 receptors Proteins 0.000 description 11
102000005962 receptors Human genes 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
230000000694 effects Effects 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000935 antidepressant agent Substances 0.000 description 7
125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
229940005513 antidepressants Drugs 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
239000012528 membrane Substances 0.000 description 6
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 5
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 5
229940076279 serotonin Drugs 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000007792 addition Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
230000000697 serotonin reuptake Effects 0.000 description 4
239000000243 solution Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 description 3
108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000013019 agitation Methods 0.000 description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000005605 benzo group Chemical group 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000009977 dual effect Effects 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 2
RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 2
HYPMZNIJCJSNFI-UHFFFAOYSA-N 1-benzothiophen-5-yl acetate Chemical compound CC(=O)OC1=CC=C2SC=CC2=C1 HYPMZNIJCJSNFI-UHFFFAOYSA-N 0.000 description 2
YYLZIBOTYCYRDP-UHFFFAOYSA-N 3-chloro-1-(5-methyl-1-benzothiophen-3-yl)propan-1-one Chemical compound CC1=CC=C2SC=C(C(=O)CCCl)C2=C1 YYLZIBOTYCYRDP-UHFFFAOYSA-N 0.000 description 2
DYWRDLBMWOHXSY-UHFFFAOYSA-N 3-chloro-1-(5-nitro-1-benzothiophen-3-yl)propan-1-one Chemical compound [O-][N+](=O)C1=CC=C2SC=C(C(=O)CCCl)C2=C1 DYWRDLBMWOHXSY-UHFFFAOYSA-N 0.000 description 2
YZKSXUIOKWQABW-UHFFFAOYSA-N 4-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=CC2=C1C=CN2 YZKSXUIOKWQABW-UHFFFAOYSA-N 0.000 description 2
102000007527 Autoreceptors Human genes 0.000 description 2
108010071131 Autoreceptors Proteins 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000009471 action Effects 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
229960002464 fluoxetine Drugs 0.000 description 2
238000011534 incubation Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000003446 ligand Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
229940094025 potassium bicarbonate Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
238000011160 research Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
125000006850 spacer group Chemical group 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
230000009466 transformation Effects 0.000 description 2
JEQDSBVHLKBEIZ-REOHCLBHSA-N (2s)-2-chloropropanoyl chloride Chemical compound C[C@H](Cl)C(Cl)=O JEQDSBVHLKBEIZ-REOHCLBHSA-N 0.000 description 1
KFVKNZPFYQDNAE-UHFFFAOYSA-N 1-(1-benzofuran-7-yl)piperazine Chemical compound C1CNCCN1C1=CC=CC2=C1OC=C2 KFVKNZPFYQDNAE-UHFFFAOYSA-N 0.000 description 1
QIIWIJVYPXMMIG-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-(4-quinolin-2-ylpiperazin-1-yl)propan-1-ol Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3N=C4C=CC=CC4=CC=3)O)=CSC2=C1 QIIWIJVYPXMMIG-UHFFFAOYSA-N 0.000 description 1
FFDJMJKKWSECNE-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-(4-quinolin-3-ylpiperazin-1-yl)propan-1-ol Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=C4C=CC=CC4=NC=3)O)=CSC2=C1 FFDJMJKKWSECNE-UHFFFAOYSA-N 0.000 description 1
XVEVCJAMXRITGQ-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-(4-quinolin-3-ylpiperazin-1-yl)propan-1-one Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=C4C=CC=CC4=NC=3)=O)=CSC2=C1 XVEVCJAMXRITGQ-UHFFFAOYSA-N 0.000 description 1
FOIILRNNRJKNDH-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-(4-quinolin-4-ylpiperazin-1-yl)propan-1-one Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C4=CC=CC=C4N=CC=3)=O)=CSC2=C1 FOIILRNNRJKNDH-UHFFFAOYSA-N 0.000 description 1
SMGADQUWFYVSES-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-(4-quinolin-6-ylpiperazin-1-yl)propan-1-ol Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=C4C=CC=NC4=CC=3)O)=CSC2=C1 SMGADQUWFYVSES-UHFFFAOYSA-N 0.000 description 1
JMKRGJJKCTXYOI-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-(4-quinolin-8-ylpiperazin-1-yl)propan-1-one;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(C(CCN3CCN(CC3)C=3C4=NC=CC=C4C=CC=3)=O)=CSC2=C1 JMKRGJJKCTXYOI-UHFFFAOYSA-N 0.000 description 1
RPKHPOCBEYNAKE-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-[4-(1-benzothiophen-5-yl)piperazin-1-yl]propan-1-ol;hydrochloride Chemical compound Cl.C1=CC=C2C(C(CCN3CCN(CC3)C=3C=C4C=CSC4=CC=3)O)=CSC2=C1 RPKHPOCBEYNAKE-UHFFFAOYSA-N 0.000 description 1
MJFXSLURCPJNSS-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-[4-(1-benzothiophen-5-yl)piperazin-1-yl]propan-1-one Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=C4C=CSC4=CC=3)=O)=CSC2=C1 MJFXSLURCPJNSS-UHFFFAOYSA-N 0.000 description 1
HSNTVSCVPWCYQE-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-[4-(1h-indol-4-yl)piperazin-1-yl]propan-1-one Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=4C=CNC=4C=CC=3)=O)=CSC2=C1 HSNTVSCVPWCYQE-UHFFFAOYSA-N 0.000 description 1
PFOITCMIPZMANM-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-[4-(2,3-dihydro-1-benzofuran-7-yl)piperazin-1-yl]propan-1-ol Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=4OCCC=4C=CC=3)O)=CSC2=C1 PFOITCMIPZMANM-UHFFFAOYSA-N 0.000 description 1
XBUDPMMXFAIIAA-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-[4-(2,3-dihydro-1-benzofuran-7-yl)piperazin-1-yl]propan-1-one Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=4OCCC=4C=CC=3)=O)=CSC2=C1 XBUDPMMXFAIIAA-UHFFFAOYSA-N 0.000 description 1
CUOHNPDRQSDSCS-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-[4-(2-methylquinolin-8-yl)piperazin-1-yl]propan-1-ol;hydrochloride Chemical compound Cl.C1=CC=C2C(C(O)CCN3CCN(CC3)C3=CC=CC4=CC=C(N=C43)C)=CSC2=C1 CUOHNPDRQSDSCS-UHFFFAOYSA-N 0.000 description 1
UHUWTCFZJOMQGZ-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-[4-(2-methylquinolin-8-yl)piperazin-1-yl]propan-1-one;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(C(=O)CCN3CCN(CC3)C3=CC=CC4=CC=C(N=C43)C)=CSC2=C1 UHUWTCFZJOMQGZ-UHFFFAOYSA-N 0.000 description 1
NRUAUZRCHDQERU-UHFFFAOYSA-N 1-(1-benzothiophen-3-yl)-3-chloropropan-1-one Chemical compound C1=CC=C2C(C(=O)CCCl)=CSC2=C1 NRUAUZRCHDQERU-UHFFFAOYSA-N 0.000 description 1
HOSAPRPVTWOIOP-UHFFFAOYSA-N 1-(5-fluoro-1-benzothiophen-3-yl)-3-(4-quinolin-8-ylpiperazin-1-yl)propan-1-ol Chemical compound C1=C(F)C=C2C(C(CCN3CCN(CC3)C=3C4=NC=CC=C4C=CC=3)O)=CSC2=C1 HOSAPRPVTWOIOP-UHFFFAOYSA-N 0.000 description 1
CCSUVDYTBGWFIB-UHFFFAOYSA-N 1-benzothiophen-5-ol Chemical compound OC1=CC=C2SC=CC2=C1 CCSUVDYTBGWFIB-UHFFFAOYSA-N 0.000 description 1
OMKZUMSCPRYKLV-UHFFFAOYSA-N 1h-indol-6-amine;propanoic acid Chemical compound CCC(O)=O.NC1=CC=C2C=CNC2=C1 OMKZUMSCPRYKLV-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
JHIAOWGCGNMQKA-UHFFFAOYSA-N 2-methyl-8-quinolinamine Chemical compound C1=CC=C(N)C2=NC(C)=CC=C21 JHIAOWGCGNMQKA-UHFFFAOYSA-N 0.000 description 1
LTDSCETYEUTUGS-UHFFFAOYSA-N 3-[4-(1,3-benzodioxol-5-yl)piperazin-1-yl]-1-(5-fluoro-1-benzothiophen-3-yl)propan-1-one Chemical compound C1=C2OCOC2=CC(N2CCN(CC2)CCC(=O)C2=CSC3=CC=C(C=C32)F)=C1 LTDSCETYEUTUGS-UHFFFAOYSA-N 0.000 description 1
XGXHJBDMQLZXKD-UHFFFAOYSA-N 3-[4-(1h-indol-4-yl)piperazin-1-yl]-1-(5-nitro-1-benzothiophen-3-yl)propan-1-ol Chemical compound C1=C([N+]([O-])=O)C=C2C(C(CCN3CCN(CC3)C=3C=4C=CNC=4C=CC=3)O)=CSC2=C1 XGXHJBDMQLZXKD-UHFFFAOYSA-N 0.000 description 1
NCPPSRQQJSJCRG-UHFFFAOYSA-N 3-[4-(1h-indol-4-yl)piperazin-1-yl]-1-(5-nitro-1-benzothiophen-3-yl)propan-1-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2SC=C1C(=O)CCN(CC1)CCN1C1=CC=CC2=C1C=CN2 NCPPSRQQJSJCRG-UHFFFAOYSA-N 0.000 description 1
HICUGZLLPZOJAH-UHFFFAOYSA-N 3-chloro-1-(5-fluoro-1-benzothiophen-3-yl)propan-1-one Chemical compound FC1=CC=C2SC=C(C(=O)CCCl)C2=C1 HICUGZLLPZOJAH-UHFFFAOYSA-N 0.000 description 1
WITJHZRCLVXYCA-UHFFFAOYSA-N 3h-1,2-benzodioxepine Chemical compound C1=CCOOC2=CC=CC=C21 WITJHZRCLVXYCA-UHFFFAOYSA-N 0.000 description 1
TWZWCQJFQURVTH-UHFFFAOYSA-N 4-[4-[3-(1-benzothiophen-3-yl)-3-hydroxypropyl]piperazin-1-yl]-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(C(CCN3CCN(CC3)C=3C=4C=C(NC=4C=CC=3)C(O)=O)O)=CSC2=C1 TWZWCQJFQURVTH-UHFFFAOYSA-N 0.000 description 1
VKBPSLNJNKFVAC-UHFFFAOYSA-N 5-fluoro-1-benzothiophene Chemical compound FC1=CC=C2SC=CC2=C1 VKBPSLNJNKFVAC-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
NOVKHIQVXQKSRL-UHFFFAOYSA-N 5-nitro-1-benzothiophene Chemical compound [O-][N+](=O)C1=CC=C2SC=CC2=C1 NOVKHIQVXQKSRL-UHFFFAOYSA-N 0.000 description 1
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
108010078791 Carrier Proteins Proteins 0.000 description 1
102000000543 Histamine Receptors Human genes 0.000 description 1
108010002059 Histamine Receptors Proteins 0.000 description 1
NYMGNSNKLVNMIA-UHFFFAOYSA-N Iproniazid Chemical compound CC(C)NNC(=O)C1=CC=NC=C1 NYMGNSNKLVNMIA-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
229910017833 NH2NH2.H2O Inorganic materials 0.000 description 1
RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
229940123445 Tricyclic antidepressant Drugs 0.000 description 1
PFKJSDBADAZVTQ-UHFFFAOYSA-N [3-(3-chloropropanoyl)-1-benzothiophen-5-yl] acetate Chemical compound CC(=O)OC1=CC=C2SC=C(C(=O)CCCl)C2=C1 PFKJSDBADAZVTQ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000004075 alteration Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229940082992 antihypertensives mao inhibitors Drugs 0.000 description 1
235000019568 aromas Nutrition 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
239000012620 biological material Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000000586 desensitisation Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
238000007429 general method Methods 0.000 description 1
230000010224 hepatic metabolism Effects 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229960004801 imipramine Drugs 0.000 description 1
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229940070023 iproniazide Drugs 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
208000030212 nutrition disease Diseases 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960002296 paroxetine Drugs 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
230000003518 presynaptic effect Effects 0.000 description 1
RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 description 1
XRXDAJYKGWNHTQ-UHFFFAOYSA-N quipazine Chemical compound C1CNCCN1C1=CC=C(C=CC=C2)C2=N1 XRXDAJYKGWNHTQ-UHFFFAOYSA-N 0.000 description 1
229950002315 quipazine Drugs 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000002295 serotoninergic effect Effects 0.000 description 1
229960002073 sertraline Drugs 0.000 description 1
VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
NZMOFYDMGFQZLS-UHFFFAOYSA-N terazosin hydrochloride dihydrate Chemical compound [H+].O.O.[Cl-].N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 NZMOFYDMGFQZLS-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms

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)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Thin Film Transistor (AREA)

OA1200300144A 2000-11-29 2001-11-19 Benzothiophene derivative compounds, process of preparation and use thereof. OA12536A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES200002914A ES2188344B1 (es)	2000-11-29	2000-11-29	Compuestos derivados de benzotiofeno, su procedimiento de obtencion y utilizacion de los mismos.

Publications (1)

Publication Number	Publication Date
OA12536A true OA12536A (en)	2006-06-05

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ID=8495887

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200300144A OA12536A (en)	2000-11-29	2001-11-19	Benzothiophene derivative compounds, process of preparation and use thereof.

Country Status (35)

Country	Link
US (1)	US20040034219A1 (no)
EP (1)	EP1337528B1 (no)
JP (1)	JP2004514719A (no)
KR (1)	KR20030066689A (no)
CN (1)	CN1478088A (no)
AP (1)	AP2003002801A0 (no)
AR (1)	AR034009A1 (no)
AT (1)	ATE272634T1 (no)
AU (1)	AU2002215157A1 (no)
BG (1)	BG107851A (no)
BR (1)	BR0115708A (no)
CA (1)	CA2429892A1 (no)
CZ (1)	CZ20031398A3 (no)
DE (1)	DE60104717T2 (no)
EA (1)	EA200300519A1 (no)
EE (1)	EE200300245A (no)
ES (2)	ES2188344B1 (no)
GE (1)	GEP20043366B (no)
HR (1)	HRP20030407A2 (no)
HU (1)	HUP0303568A3 (no)
IL (1)	IL155966A0 (no)
IS (1)	IS6824A (no)
MA (1)	MA26963A1 (no)
MX (1)	MXPA03004875A (no)
NO (1)	NO20032332D0 (no)
NZ (1)	NZ525950A (no)
OA (1)	OA12536A (no)
PE (1)	PE20020692A1 (no)
PL (1)	PL362982A1 (no)
PT (1)	PT1337528E (no)
SI (1)	SI1337528T1 (no)
SK (1)	SK6202003A3 (no)
TR (1)	TR200402779T4 (no)
WO (1)	WO2002044170A2 (no)
ZA (1)	ZA200303858B (no)

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BRPI0308696B8 (pt)	2002-03-27	2021-05-25	Axovant Sciences Gmbh	composto derivado de quinolina, seu processo de preparação, sua composição farmacêutica e seus usos
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US7276603B2 (en)	2003-05-02	2007-10-02	Wyeth	Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use
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DE102004023522A1 (de) *	2004-05-10	2005-12-01	Grünenthal GmbH	Substituierte Cyclohexyl-1,4-diamin-Derivate
DE102004023632A1 (de) *	2004-05-10	2005-12-08	Grünenthal GmbH	Substituierte Cyclohexylcarbonsäure-Derivate
DE102004023506A1 (de) *	2004-05-10	2005-12-01	Grünenthal GmbH	Kettenverlängerte substituierte Cyclohexyl-1,4-diamin-Derivate
DE102004023635A1 (de) *	2004-05-10	2006-04-13	Grünenthal GmbH	Heteroarylsubstituierte Cyclohexyl-1,4-diamin-Derivate
DE102004023508A1 (de) *	2004-05-10	2005-12-08	Grünenthal GmbH	Säurederivate substituierter Cyclohexyl-1,4-diamine
DE102004023501A1 (de) *	2004-05-10	2005-12-01	Grünenthal GmbH	Oxosubstituierte Cyclohexyl-1,4-diamin-Derivate
DE102004023507A1 (de) *	2004-05-10	2005-12-01	Grünenthal GmbH	Substituierte Cyclohexylessigsäure-Derivate
US7881267B2 (en) *	2004-06-04	2011-02-01	Hewlett-Packard Development Company, L.P.	Portable computing device for wireless communications and method of operation
DE102004063797A1 (de) *	2004-12-30	2006-07-13	Schwarz Pharma Ag	Sauerstoffhaltige annelierte Phenylpiperazin- und Phenyldiazepancarboxamide
US7582634B2 (en)	2005-02-18	2009-09-01	Wyeth	7-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor
US7538113B2 (en)	2005-02-18	2009-05-26	Wyeth	4-substituted imidazo[4,5-c]pyridine antagonists of gonadotropin releasing hormone receptor
US7534796B2 (en)	2005-02-18	2009-05-19	Wyeth	Imidazo[4,5-b]pyridine antagonists of gonadotropin releasing hormone receptor
TWI320783B (en)	2005-04-14	2010-02-21	Otsuka Pharma Co Ltd	Heterocyclic compound
US7531542B2 (en)	2005-05-18	2009-05-12	Wyeth	Benzooxazole and benzothiazole antagonists of gonadotropin releasing hormone receptor
US7582636B2 (en)	2005-05-26	2009-09-01	Wyeth	Piperazinylimidazopyridine and piperazinyltriazolopyridine antagonists of Gonadotropin Releasing Hormone receptor
EP2508177A1 (en)	2007-12-12	2012-10-10	Glaxo Group Limited	Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline
WO2009123714A2 (en)	2008-04-02	2009-10-08	Arena Pharmaceuticals, Inc.	Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor
CN101619056B (zh)	2008-07-02	2013-07-17	石药集团中奇制药技术（石家庄）有限公司	苯并噻吩烷醇哌嗪衍生物及其作为抗抑郁症药物的应用
WO2010062321A1 (en)	2008-10-28	2010-06-03	Arena Pharmaceuticals, Inc.	Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto
US9598401B2 (en)	2013-07-29	2017-03-21	Sunshine Lake Pharma Co., Ltd.	Substituted heteroaryl compounds and methods of use thereof
CN106243088B (zh)	2015-06-03	2019-01-04	广东东阳光药业有限公司	取代的哌嗪化合物及其使用方法和用途
WO2016201373A1 (en)	2015-06-12	2016-12-15	Axovant Sciences Ltd.	Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of rem sleep behavior disorder
WO2017011767A2 (en)	2015-07-15	2017-01-19	Axovant Sciences Ltd.	Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease

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ES2128266B1 (es) *	1997-07-08	2000-01-16	Vita Invest Sa	Compuestos derivados de tiofeno y benzotiofeno y utilizacion y composicion correspondientes.

2000
- 2000-11-29 ES ES200002914A patent/ES2188344B1/es not_active Expired - Fee Related
2001
- 2001-11-19 WO PCT/IB2001/002211 patent/WO2002044170A2/en not_active Ceased
- 2001-11-19 HU HU0303568A patent/HUP0303568A3/hu unknown
- 2001-11-19 EE EEP200300245A patent/EE200300245A/xx unknown
- 2001-11-19 ES ES01983737T patent/ES2225623T3/es not_active Expired - Lifetime
- 2001-11-19 BR BR0115708-6A patent/BR0115708A/pt not_active IP Right Cessation
- 2001-11-19 NZ NZ525950A patent/NZ525950A/en unknown
- 2001-11-19 PL PL01362982A patent/PL362982A1/xx unknown
- 2001-11-19 JP JP2002546540A patent/JP2004514719A/ja active Pending
- 2001-11-19 IL IL15596601A patent/IL155966A0/xx unknown
- 2001-11-19 KR KR10-2003-7007272A patent/KR20030066689A/ko not_active Ceased
- 2001-11-19 HR HR20030407A patent/HRP20030407A2/hr not_active Application Discontinuation
- 2001-11-19 AP APAP/P/2003/002801A patent/AP2003002801A0/en unknown
- 2001-11-19 DE DE60104717T patent/DE60104717T2/de not_active Expired - Fee Related
- 2001-11-19 AU AU2002215157A patent/AU2002215157A1/en not_active Abandoned
- 2001-11-19 SI SI200130192T patent/SI1337528T1/xx unknown
- 2001-11-19 GE GE5158A patent/GEP20043366B/en unknown
- 2001-11-19 PT PT01983737T patent/PT1337528E/pt unknown
- 2001-11-19 EA EA200300519A patent/EA200300519A1/ru unknown
- 2001-11-19 CZ CZ20031398A patent/CZ20031398A3/cs unknown
- 2001-11-19 CA CA002429892A patent/CA2429892A1/en not_active Abandoned
- 2001-11-19 OA OA1200300144A patent/OA12536A/en unknown
- 2001-11-19 US US10/432,697 patent/US20040034219A1/en not_active Abandoned
- 2001-11-19 TR TR2004/02779T patent/TR200402779T4/xx unknown
- 2001-11-19 AT AT01983737T patent/ATE272634T1/de not_active IP Right Cessation
- 2001-11-19 EP EP01983737A patent/EP1337528B1/en not_active Expired - Lifetime
- 2001-11-19 CN CNA018196004A patent/CN1478088A/zh active Pending
- 2001-11-19 SK SK620-2003A patent/SK6202003A3/sk unknown
- 2001-11-19 MX MXPA03004875A patent/MXPA03004875A/es unknown
- 2001-11-26 PE PE2001001181A patent/PE20020692A1/es not_active Application Discontinuation
- 2001-11-27 AR ARP010105490A patent/AR034009A1/es not_active Application Discontinuation
2003
- 2003-05-19 ZA ZA200303858A patent/ZA200303858B/en unknown
- 2003-05-19 MA MA27164A patent/MA26963A1/fr unknown
- 2003-05-22 NO NO20032332A patent/NO20032332D0/no not_active Application Discontinuation
- 2003-05-22 IS IS6824A patent/IS6824A/is unknown
- 2003-05-27 BG BG107851A patent/BG107851A/bg unknown

Also Published As

Publication number	Publication date
HRP20030407A2 (en)	2004-08-31
MXPA03004875A (es)	2005-02-14
ES2225623T3 (es)	2005-03-16
WO2002044170A2 (en)	2002-06-06
NZ525950A (en)	2004-11-26
NO20032332L (no)	2003-05-22
US20040034219A1 (en)	2004-02-19
EP1337528B1 (en)	2004-08-04
HUP0303568A2 (hu)	2004-03-01
PT1337528E (pt)	2004-11-30
IL155966A0 (en)	2003-12-23
BG107851A (bg)	2004-06-30
DE60104717D1 (de)	2004-09-09
WO2002044170A3 (en)	2002-09-06
PL362982A1 (en)	2004-11-02
AR034009A1 (es)	2004-01-21
MA26963A1 (fr)	2004-12-20
KR20030066689A (ko)	2003-08-09
ATE272634T1 (de)	2004-08-15
EE200300245A (et)	2003-08-15
ES2188344A1 (es)	2003-06-16
TR200402779T4 (tr)	2004-11-22
PE20020692A1 (es)	2002-09-02
SK6202003A3 (en)	2004-05-04
BR0115708A (pt)	2004-02-03
IS6824A (is)	2003-05-22
CN1478088A (zh)	2004-02-25
EP1337528A2 (en)	2003-08-27
NO20032332D0 (no)	2003-05-22
ES2188344B1 (es)	2004-09-16
SI1337528T1 (en)	2005-02-28
AU2002215157A1 (en)	2002-06-11
ZA200303858B (en)	2004-05-19
JP2004514719A (ja)	2004-05-20
CZ20031398A3 (cs)	2004-01-14
AP2003002801A0 (en)	2003-06-30
EA200300519A1 (ru)	2003-12-25
GEP20043366B (en)	2004-04-13
DE60104717T2 (de)	2006-04-06
CA2429892A1 (en)	2002-06-06
HUP0303568A3 (en)	2005-02-28

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