ES2360254T3 - Compuestos de ariloxietilamina adecuados para tratamiento de trastornos que respondan a la modulación del receptor de dopamina d3. - Google Patents

Compuestos de ariloxietilamina adecuados para tratamiento de trastornos que respondan a la modulación del receptor de dopamina d3. Download PDF

Info

Publication number: ES2360254T3
Authority: ES; Spain
Prior art keywords: phenyl; alkyl; fluorinated; alkoxy; methyl
Prior art date: 2006-04-14
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.): Active

Application number

ES07728098T

Other languages

English (en)

Spanish (es)

Inventor

Roland Grandel

Wilfried Martin Braje

Andreas Haupt

Sean Colm Turner

Udo Lange

Karla Drescher

Liliane Unger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Abbott GmbH and Co KG

Original Assignee

Abbott GmbH and Co KG

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.)

2006-04-14

Filing date

2007-04-13

Publication date

2011-06-02

2007-04-13 Application filed by Abbott GmbH and Co KG filed Critical Abbott GmbH and Co KG

2011-06-02 Application granted granted Critical

2011-06-02 Publication of ES2360254T3 publication Critical patent/ES2360254T3/es

Status Active legal-status Critical Current

2027-04-13 Anticipated expiration legal-status Critical

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 145
238000011282 treatment Methods 0.000 title claims description 18
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title description 12
229960003638 dopamine Drugs 0.000 title description 5
-1 phenoxy, benzyloxy, pyridine -2- yloxy Chemical group 0.000 claims abstract description 2416
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 56
239000002253 acid Substances 0.000 claims abstract description 52
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 51
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
229910052731 fluorine Inorganic materials 0.000 claims abstract description 32
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 31
229910052736 halogen Inorganic materials 0.000 claims abstract description 31
150000002367 halogens Chemical class 0.000 claims abstract description 31
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 30
125000000217 alkyl group Chemical group 0.000 claims abstract description 29
239000011737 fluorine Substances 0.000 claims abstract description 27
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 23
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 19
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 17
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 16
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 15
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 15
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 14
125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
125000005113 hydroxyalkoxy group Chemical group 0.000 claims abstract description 13
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 12
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 12
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 7
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims abstract description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 7
125000002837 carbocyclic group Chemical group 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 5
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 4
150000003254 radicals Chemical class 0.000 claims description 115
229910052739 hydrogen Inorganic materials 0.000 claims description 48
239000001257 hydrogen Substances 0.000 claims description 39
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 23
208000035475 disorder Diseases 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 15
239000003446 ligand Substances 0.000 claims description 13
108090000525 Dopamine D3 Receptors Proteins 0.000 claims description 12
102000004073 Dopamine D3 Receptors Human genes 0.000 claims description 12
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 10
HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000006002 1,1-difluoroethyl group Chemical group 0.000 claims description 3
125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 claims description 3
125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 3
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
208000015114 central nervous system disease Diseases 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
125000000842 isoxazolyl group Chemical group 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
125000003226 pyrazolyl group Chemical group 0.000 claims 1
125000000168 pyrrolyl group Chemical group 0.000 claims 1
125000003831 tetrazolyl group Chemical group 0.000 claims 1
125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 abstract description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 3
125000005097 aminocarbonylalkyl group Chemical group 0.000 abstract 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 116
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
238000005160 1H NMR spectroscopy Methods 0.000 description 70
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
239000000203 mixture Substances 0.000 description 57
238000000034 method Methods 0.000 description 55
239000002904 solvent Substances 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
239000000047 product Substances 0.000 description 40
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 34
230000002829 reductive effect Effects 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
102000005962 receptors Human genes 0.000 description 23
108020003175 receptors Proteins 0.000 description 23
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 22
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
238000002360 preparation method Methods 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
239000003480 eluent Substances 0.000 description 19
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000543 intermediate Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
125000004429 atom Chemical group 0.000 description 14
230000027455 binding Effects 0.000 description 14
239000000460 chlorine Substances 0.000 description 14
229910052801 chlorine Inorganic materials 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 13
201000010099 disease Diseases 0.000 description 13
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 12
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
239000012043 crude product Substances 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
239000012044 organic layer Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 11
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000012360 testing method Methods 0.000 description 10
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 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 9
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 9
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
208000024891 symptom Diseases 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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 8
CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 7
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 7
PORSSVZRVASZRT-UHFFFAOYSA-N 4-(1,1,1-trifluoropropan-2-yl)benzenesulfonyl chloride Chemical compound FC(F)(F)C(C)C1=CC=C(S(Cl)(=O)=O)C=C1 PORSSVZRVASZRT-UHFFFAOYSA-N 0.000 description 6
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 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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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 6
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 6
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
239000003814 drug Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000001153 fluoro group Chemical group F* 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
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125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 5
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OMOZIEOLBBCAFW-UHFFFAOYSA-N 6-bromo-2-methoxy-3-nitropyridine Chemical compound COC1=NC(Br)=CC=C1[N+]([O-])=O OMOZIEOLBBCAFW-UHFFFAOYSA-N 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
206010012335 Dependence Diseases 0.000 description 5
102000015554 Dopamine receptor Human genes 0.000 description 5
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
230000003907 kidney function Effects 0.000 description 5
230000007257 malfunction Effects 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
150000002941 palladium compounds Chemical class 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
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238000010561 standard procedure Methods 0.000 description 5
RMSBMILECANKNX-UHFFFAOYSA-N 2-[benzyl(propyl)amino]ethanol Chemical compound CCCN(CCO)CC1=CC=CC=C1 RMSBMILECANKNX-UHFFFAOYSA-N 0.000 description 4
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238000007911 parenteral administration Methods 0.000 description 1
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239000000049 pigment Substances 0.000 description 1
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239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
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RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
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208000020016 psychiatric disease Diseases 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
150000003284 rhodium compounds Chemical class 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
208000022925 sleep disturbance Diseases 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000011343 solid material Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000015883 synaptic transmission, dopaminergic Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
230000035922 thirst Effects 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
231100000889 vertigo Toxicity 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

ES07728098T 2006-04-14 2007-04-13 Compuestos de ariloxietilamina adecuados para tratamiento de trastornos que respondan a la modulación del receptor de dopamina d3. Active ES2360254T3 (es)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP06007923		2006-04-14
EP06007923		2006-04-14
US793671P		2006-04-20

Publications (1)

Publication Number	Publication Date
ES2360254T3 true ES2360254T3 (es)	2011-06-02

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ES07728098T Active ES2360254T3 (es)	2006-04-14	2007-04-13	Compuestos de ariloxietilamina adecuados para tratamiento de trastornos que respondan a la modulación del receptor de dopamina d3.

Country Status (6)

Country	Link
CN (1)	CN101421243B (de)
AT (1)	ATE496031T1 (de)
DE (1)	DE602007012071D1 (de)
ES (1)	ES2360254T3 (de)
PE (1)	PE20080057A1 (de)
TW (1)	TWI400233B (de)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW450954B (en) *	1998-05-14	2001-08-21	Pharmacia & Amp Upjohn Company	Phenylsulfonamide-phenylethylamines useful as dopamine receptors
WO2003068732A2 (en) *	2002-02-13	2003-08-21	Glaxo Group Limited	Benzenesulfonamide derivatives and their use as dopamine d3 and d2 receptor liga ds
GB0411421D0 (en) *	2004-05-21	2004-06-23	Glaxo Group Ltd	Novel compounds

2007
- 2007-04-13 AT AT07728098T patent/ATE496031T1/de not_active IP Right Cessation
- 2007-04-13 TW TW96113061A patent/TWI400233B/zh not_active IP Right Cessation
- 2007-04-13 CN CN2007800134447A patent/CN101421243B/zh not_active Expired - Fee Related
- 2007-04-13 PE PE2007000456A patent/PE20080057A1/es not_active Application Discontinuation
- 2007-04-13 DE DE602007012071T patent/DE602007012071D1/de active Active
- 2007-04-13 ES ES07728098T patent/ES2360254T3/es active Active

Also Published As

Publication number	Publication date
TWI400233B (zh)	2013-07-01
PE20080057A1 (es)	2008-03-10
CN101421243A (zh)	2009-04-29
TW200808727A (en)	2008-02-16
ATE496031T1 (de)	2011-02-15
DE602007012071D1 (de)	2011-03-03
CN101421243B (zh)	2012-05-30

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