RU2373204C2 - Бензимидазольные, бензтиазольные и бензоксазольные производные и их применение в качестве модуляторов lta4h - Google Patents
Бензимидазольные, бензтиазольные и бензоксазольные производные и их применение в качестве модуляторов lta4h Download PDFInfo
- Publication number
- RU2373204C2 RU2373204C2 RU2006102510/04A RU2006102510A RU2373204C2 RU 2373204 C2 RU2373204 C2 RU 2373204C2 RU 2006102510/04 A RU2006102510/04 A RU 2006102510/04A RU 2006102510 A RU2006102510 A RU 2006102510A RU 2373204 C2 RU2373204 C2 RU 2373204C2
- Authority
- RU
- Russia
- Prior art keywords
- ethyl
- yloxy
- benzothiazol
- phenyl
- phenoxy
- Prior art date
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims description 48
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title claims description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title description 2
- -1 1,3-dihydrobenzoimidazol-2-on-1-yl Chemical group 0.000 claims abstract description 322
- 150000001875 compounds Chemical class 0.000 claims abstract description 294
- 238000000034 method Methods 0.000 claims abstract description 168
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 136
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 112
- 150000001721 carbon Chemical group 0.000 claims abstract description 104
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 101
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 89
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
- 108010072713 leukotriene A4 hydrolase Proteins 0.000 claims abstract description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 46
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 46
- 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 claims abstract description 43
- 206010061218 Inflammation Diseases 0.000 claims abstract description 34
- 230000004054 inflammatory process Effects 0.000 claims abstract description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 32
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 28
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 230000001404 mediated effect Effects 0.000 claims abstract description 17
- 239000003112 inhibitor Substances 0.000 claims abstract description 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 15
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 12
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 9
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- PBYPGZHIAKLYFN-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-3-carboxylic acid Chemical compound C1CN(C(=O)O)CCC11CCNCC1 PBYPGZHIAKLYFN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 144
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 96
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 66
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 24
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 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 claims description 18
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 13
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 12
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 11
- 125000003368 amide group Chemical group 0.000 claims description 11
- 208000006673 asthma Diseases 0.000 claims description 11
- QFDISQIDKZUABE-UHFFFAOYSA-N 1,1'-bipiperidine Chemical compound C1CCCCN1N1CCCCC1 QFDISQIDKZUABE-UHFFFAOYSA-N 0.000 claims description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 201000004681 Psoriasis Diseases 0.000 claims description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
- YMOXSVLBXXDKHI-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YMOXSVLBXXDKHI-UHFFFAOYSA-N 0.000 claims description 9
- JFYFFICGEIKUMA-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 JFYFFICGEIKUMA-UHFFFAOYSA-N 0.000 claims description 8
- MLSPCHBWRYAMOL-UHFFFAOYSA-N 2-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]tetrazol-5-yl]butanoic acid Chemical compound C(C)C(C(=O)O)C1=NN=NN1CCOC1=CC=C(C=C1)OC=1SC2=C(N=1)C=CC=C2 MLSPCHBWRYAMOL-UHFFFAOYSA-N 0.000 claims description 8
- DHHMVJVCMLXZBO-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN1CCCCC1 DHHMVJVCMLXZBO-UHFFFAOYSA-N 0.000 claims description 8
- SBIHJWUTAGVKMS-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]butanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC(=O)O)C1CC1 SBIHJWUTAGVKMS-UHFFFAOYSA-N 0.000 claims description 8
- NJXASJKPUOBSSP-UHFFFAOYSA-N ethyl 4-[(1-acetylpiperidin-4-yl)-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]amino]butanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC(=O)OCC)C1CCN(C(C)=O)CC1 NJXASJKPUOBSSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004494 ethyl ester group Chemical group 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 8
- GWSZYUJFYKFDPN-UHFFFAOYSA-N methyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GWSZYUJFYKFDPN-UHFFFAOYSA-N 0.000 claims description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims description 8
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- ALUPMMYRKWGOJR-GOSISDBHSA-N (4r)-1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-4-hydroxypyrrolidin-2-one Chemical compound O=C1C[C@@H](O)CN1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ALUPMMYRKWGOJR-GOSISDBHSA-N 0.000 claims description 6
- YALDRDNOXRAUNF-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-3-methylbenzimidazol-2-one Chemical compound C1=CC=C2SC(OC3=CC=C(C=C3)CCN3CCC(CC3)N3C4=CC=CC=C4N(C3=O)C)=NC2=C1 YALDRDNOXRAUNF-UHFFFAOYSA-N 0.000 claims description 6
- QWCBCDWVFAMHOI-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 QWCBCDWVFAMHOI-UHFFFAOYSA-N 0.000 claims description 6
- GZGNIPCWBLJDPJ-UHFFFAOYSA-N 1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3NC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 GZGNIPCWBLJDPJ-UHFFFAOYSA-N 0.000 claims description 6
- UALALAOOEVHOAE-UHFFFAOYSA-N 1-[3-[4-(1,3-benzoxazol-2-yloxy)phenoxy]-2-hydroxypropyl]-4-phenylpiperidin-4-ol Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCC(O)CN(CC1)CCC1(O)C1=CC=CC=C1 UALALAOOEVHOAE-UHFFFAOYSA-N 0.000 claims description 6
- WQRHRQZGBVOFLB-UHFFFAOYSA-N 1-[3-[4-(1,3-benzoxazol-2-yloxy)phenoxy]propyl]-4-benzylpiperidin-4-ol Chemical compound C1CN(CCCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)CC1=CC=CC=C1 WQRHRQZGBVOFLB-UHFFFAOYSA-N 0.000 claims description 6
- IZRJFWRSXHIPAP-UHFFFAOYSA-N 1-[3-[4-(1,3-benzoxazol-2-yloxy)phenoxy]propyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 IZRJFWRSXHIPAP-UHFFFAOYSA-N 0.000 claims description 6
- QDZNAVQKPOLUCJ-UHFFFAOYSA-N 1-[3-[4-(1,3-benzoxazol-2-yloxy)phenyl]propyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 QDZNAVQKPOLUCJ-UHFFFAOYSA-N 0.000 claims description 6
- ZIQGASWXUSSORV-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethoxy)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCCCC1 ZIQGASWXUSSORV-UHFFFAOYSA-N 0.000 claims description 6
- DDPDHHQNYWOFTO-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN1CCCCC1 DDPDHHQNYWOFTO-UHFFFAOYSA-N 0.000 claims description 6
- IKCVCAQFEIOACD-UHFFFAOYSA-N 4-[2-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]ethyl]morpholine Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1CCN1CCOCC1 IKCVCAQFEIOACD-UHFFFAOYSA-N 0.000 claims description 6
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 6
- MPTCZYWZERBJFR-UHFFFAOYSA-N C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCNCCC1CCCCC1 Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCNCCC1CCCCC1 MPTCZYWZERBJFR-UHFFFAOYSA-N 0.000 claims description 6
- DUOJBDYMEDTCDU-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 DUOJBDYMEDTCDU-UHFFFAOYSA-N 0.000 claims description 6
- MVWHGHDOPRCATH-UHFFFAOYSA-N [1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 MVWHGHDOPRCATH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- SVIXKYOSUKPYTE-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzoxazol-2-ylmethyl)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C=C1)=CC=C1CC1=NC2=CC=CC=C2O1 SVIXKYOSUKPYTE-UHFFFAOYSA-N 0.000 claims description 6
- CMLMEBPFTNCLDG-UHFFFAOYSA-N methyl 1-[2-[4-(1,3-benzothiazol-2-ylmethyl)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCOC(C=C1)=CC=C1CC1=NC2=CC=CC=C2S1 CMLMEBPFTNCLDG-UHFFFAOYSA-N 0.000 claims description 6
- JRXIQERDUYKZID-UHFFFAOYSA-N n-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(OCCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2O1 JRXIQERDUYKZID-UHFFFAOYSA-N 0.000 claims description 6
- ICEHPSYAPXDUNH-UHFFFAOYSA-N n-[3-[4-(1,3-benzoxazol-2-yloxy)phenyl]propyl]-n-ethylcyclohexanamine Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCCN(CC)C1CCCCC1 ICEHPSYAPXDUNH-UHFFFAOYSA-N 0.000 claims description 6
- OAUXHFPOFOZZLZ-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 OAUXHFPOFOZZLZ-UHFFFAOYSA-N 0.000 claims description 5
- GVNNEHBYBWFJRK-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-3h-indol-2-one Chemical compound C1=CC=C2SC(OC3=CC=C(C=C3)CCN3CCC(CC3)N3C4=CC=CC=C4CC3=O)=NC2=C1 GVNNEHBYBWFJRK-UHFFFAOYSA-N 0.000 claims description 5
- GIYCUMSDCASBAI-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 GIYCUMSDCASBAI-UHFFFAOYSA-N 0.000 claims description 5
- LJCQRMOXTNWQDA-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-phenylpiperidin-4-yl]ethanone Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(C(=O)C)C1=CC=CC=C1 LJCQRMOXTNWQDA-UHFFFAOYSA-N 0.000 claims description 5
- AREHXWXMLHRGGI-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-(4-bromophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Br)C=C1 AREHXWXMLHRGGI-UHFFFAOYSA-N 0.000 claims description 5
- FQIDMNGIAGRBQM-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C=C1 FQIDMNGIAGRBQM-UHFFFAOYSA-N 0.000 claims description 5
- JAAJPVQIKRVPLX-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 JAAJPVQIKRVPLX-UHFFFAOYSA-N 0.000 claims description 5
- QEEKSUQXDWTJIW-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QEEKSUQXDWTJIW-UHFFFAOYSA-N 0.000 claims description 5
- FDTVVMYDEDPLPY-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 FDTVVMYDEDPLPY-UHFFFAOYSA-N 0.000 claims description 5
- OQXYLEOVNNJHIM-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 OQXYLEOVNNJHIM-UHFFFAOYSA-N 0.000 claims description 5
- HTPHRBUADWIZAP-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HTPHRBUADWIZAP-UHFFFAOYSA-N 0.000 claims description 5
- SNAOZGAXOCNDQE-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-ylmethyl)phenoxy]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(CC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 SNAOZGAXOCNDQE-UHFFFAOYSA-N 0.000 claims description 5
- FPBJSKXLGYSYTB-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-(4-bromophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Br)C=C1 FPBJSKXLGYSYTB-UHFFFAOYSA-N 0.000 claims description 5
- ZVHUCYIDOVOMPL-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C=C1 ZVHUCYIDOVOMPL-UHFFFAOYSA-N 0.000 claims description 5
- QZUSHEKSEOJALY-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-[4-chloro-3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 QZUSHEKSEOJALY-UHFFFAOYSA-N 0.000 claims description 5
- HHLUBZRJHIJQOR-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-benzylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)CC1=CC=CC=C1 HHLUBZRJHIJQOR-UHFFFAOYSA-N 0.000 claims description 5
- DXYLCDRFEVYPSH-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 DXYLCDRFEVYPSH-UHFFFAOYSA-N 0.000 claims description 5
- TVPIVMADGYPLGR-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-4-phenylpiperidine-4-carbonitrile Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(C#N)C1=CC=CC=C1 TVPIVMADGYPLGR-UHFFFAOYSA-N 0.000 claims description 5
- NAPJFLJCOCOANV-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenyl]ethyl]-4-phenylpiperidin-4-ol Chemical compound C1CN(CCC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=CC=C1 NAPJFLJCOCOANV-UHFFFAOYSA-N 0.000 claims description 5
- FMPGQGRECBCTKX-UHFFFAOYSA-N 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenyl]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 FMPGQGRECBCTKX-UHFFFAOYSA-N 0.000 claims description 5
- JXYJUSHUPLHJSU-UHFFFAOYSA-N 1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]-4-(4-bromophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3NC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Br)C=C1 JXYJUSHUPLHJSU-UHFFFAOYSA-N 0.000 claims description 5
- SLXLUQUQEXXURU-UHFFFAOYSA-N 1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]-4-(4-chlorophenyl)piperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3NC4=CC=CC=C4N=3)=CC=2)CCC1(O)C1=CC=C(Cl)C=C1 SLXLUQUQEXXURU-UHFFFAOYSA-N 0.000 claims description 5
- NGJLFGIXUBVPMH-UHFFFAOYSA-N 1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]-4-benzylpiperidin-4-ol Chemical compound C1CN(CCOC=2C=CC(OC=3NC4=CC=CC=C4N=3)=CC=2)CCC1(O)CC1=CC=CC=C1 NGJLFGIXUBVPMH-UHFFFAOYSA-N 0.000 claims description 5
- RGSKAUKKFAHXLD-UHFFFAOYSA-N 1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 RGSKAUKKFAHXLD-UHFFFAOYSA-N 0.000 claims description 5
- XGDQMSMNYLATFY-UHFFFAOYSA-N 1-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 XGDQMSMNYLATFY-UHFFFAOYSA-N 0.000 claims description 5
- GLTMBLQAEJWHDD-UHFFFAOYSA-N 1-[4-(1,3-benzoxazol-2-yloxy)phenoxy]-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCC(O)CN1CCCC1 GLTMBLQAEJWHDD-UHFFFAOYSA-N 0.000 claims description 5
- DEEFUNGCPNDDFM-UHFFFAOYSA-N 2-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl-benzylamino]ethanol Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN(CCO)CC1=CC=CC=C1 DEEFUNGCPNDDFM-UHFFFAOYSA-N 0.000 claims description 5
- KSTQAHVAEMPYHX-UHFFFAOYSA-N 2-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl-propylamino]ethanol Chemical compound C1=CC(OCCN(CCO)CCC)=CC=C1OC1=NC2=CC=CC=C2O1 KSTQAHVAEMPYHX-UHFFFAOYSA-N 0.000 claims description 5
- XUJPSBWIEBYUCZ-UHFFFAOYSA-N 2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]-n,n-dimethylethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1OC1=NC2=CC=CC=C2S1 XUJPSBWIEBYUCZ-UHFFFAOYSA-N 0.000 claims description 5
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- MJLBZFXLDHOOMN-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethoxy)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1CCCC1 MJLBZFXLDHOOMN-UHFFFAOYSA-N 0.000 claims description 5
- NNHHNGXLAAEJGV-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethoxy)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCCC1 NNHHNGXLAAEJGV-UHFFFAOYSA-N 0.000 claims description 5
- ICDQXKCQGHKKOJ-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethyl)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN1CCCC1 ICDQXKCQGHKKOJ-UHFFFAOYSA-N 0.000 claims description 5
- SSQAGYBYJTZVJM-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethyl)phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN1CCCC1 SSQAGYBYJTZVJM-UHFFFAOYSA-N 0.000 claims description 5
- MHONEQKAPWEUHV-UHFFFAOYSA-N 2-[4-(2-pyrrolidin-1-ylethyl)phenoxy]-1h-benzimidazole Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CCN1CCCC1 MHONEQKAPWEUHV-UHFFFAOYSA-N 0.000 claims description 5
- CXWBSAGMDCVRGR-UHFFFAOYSA-N 2-[4-[2-(2-ethylpiperidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound CCC1CCCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 CXWBSAGMDCVRGR-UHFFFAOYSA-N 0.000 claims description 5
- MOQCNLBYCQEEOO-UHFFFAOYSA-N 2-[4-[2-(4-benzylpiperidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN(CC1)CCC1CC1=CC=CC=C1 MOQCNLBYCQEEOO-UHFFFAOYSA-N 0.000 claims description 5
- FHNXSUARUMPPBX-UHFFFAOYSA-N 2-[4-[2-(4-methylpiperidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C1CC(C)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 FHNXSUARUMPPBX-UHFFFAOYSA-N 0.000 claims description 5
- ARICAWUKBOMLHN-UHFFFAOYSA-N 2-[4-[2-(4-methylpiperidin-1-yl)ethoxy]phenoxy]-1h-benzimidazole Chemical compound C1CC(C)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 ARICAWUKBOMLHN-UHFFFAOYSA-N 0.000 claims description 5
- JDZUDVCYJPNUKO-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethoxy]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1CCCCCC1 JDZUDVCYJPNUKO-UHFFFAOYSA-N 0.000 claims description 5
- RUOSQGLZVMYCMI-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCCCCC1 RUOSQGLZVMYCMI-UHFFFAOYSA-N 0.000 claims description 5
- ZCXJIZDGNNOQMQ-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethoxy]phenoxy]-6-methoxy-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1OC(C=C1)=CC=C1OCCN1CCCCCC1 ZCXJIZDGNNOQMQ-UHFFFAOYSA-N 0.000 claims description 5
- WIKXKXLDBRNVDS-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethyl]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN1CCCCCC1 WIKXKXLDBRNVDS-UHFFFAOYSA-N 0.000 claims description 5
- CWRZHUUNHAVDCE-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethyl]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN1CCCCCC1 CWRZHUUNHAVDCE-UHFFFAOYSA-N 0.000 claims description 5
- OYYUXPQRNJIYPV-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethyl]phenoxy]-1h-benzimidazole Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CCN1CCCCCC1 OYYUXPQRNJIYPV-UHFFFAOYSA-N 0.000 claims description 5
- JYGZPGXROUXHGB-UHFFFAOYSA-N 2-[4-[2-(azetidin-1-yl)ethoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN1CCC1 JYGZPGXROUXHGB-UHFFFAOYSA-N 0.000 claims description 5
- OASLEWALRHQUOX-UHFFFAOYSA-N 2-[4-[3-(4-phenylpiperidin-1-yl)propoxy]phenoxy]-1,3-benzoxazole Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCCN(CC1)CCC1C1=CC=CC=C1 OASLEWALRHQUOX-UHFFFAOYSA-N 0.000 claims description 5
- QJLVQPXNAJBHTN-UHFFFAOYSA-N 3-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl-cyclopropylamino]propanoic acid Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CCC(=O)O)C1CC1 QJLVQPXNAJBHTN-UHFFFAOYSA-N 0.000 claims description 5
- FMVQUDIPYZBTQP-UHFFFAOYSA-N 3-[4-(1,3-benzothiazol-2-yloxy)phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1OC1=NC2=CC=CC=C2S1 FMVQUDIPYZBTQP-UHFFFAOYSA-N 0.000 claims description 5
- NAXZPROAWKTLMQ-UHFFFAOYSA-N 3-[4-(1,3-benzoxazol-2-yloxy)phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1OC1=NC2=CC=CC=C2O1 NAXZPROAWKTLMQ-UHFFFAOYSA-N 0.000 claims description 5
- GOGNXTVASAKEPB-UHFFFAOYSA-N 3-[4-(1,3-benzoxazol-2-yloxy)phenyl]-n-(cyclopropylmethyl)-n-propylpropan-1-amine Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCCN(CCC)CC1CC1 GOGNXTVASAKEPB-UHFFFAOYSA-N 0.000 claims description 5
- JNPNVLKDSZMXFQ-UHFFFAOYSA-N 4-[2-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperazin-1-yl]ethyl]morpholine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN(CC1)CCN1CCN1CCOCC1 JNPNVLKDSZMXFQ-UHFFFAOYSA-N 0.000 claims description 5
- ZKBRIYLQMSDIBH-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1NCCC11CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ZKBRIYLQMSDIBH-UHFFFAOYSA-N 0.000 claims description 5
- ZCAWZNVFLHPUNA-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-2,8-diazaspiro[4.5]decan-1-one Chemical compound O=C1NCCC11CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 ZCAWZNVFLHPUNA-UHFFFAOYSA-N 0.000 claims description 5
- YBXRXEPYGMEBCW-UHFFFAOYSA-N C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCNCCC1CCCCC1 Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCNCCC1CCCCC1 YBXRXEPYGMEBCW-UHFFFAOYSA-N 0.000 claims description 5
- UBYQAOUYHYNYEY-UHFFFAOYSA-N C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCNCCC1CCCCC1 Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCNCCC1CCCCC1 UBYQAOUYHYNYEY-UHFFFAOYSA-N 0.000 claims description 5
- BPWOKYZNXJXEDX-UHFFFAOYSA-N C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCNCCC1CCCCC1 Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCNCCC1CCCCC1 BPWOKYZNXJXEDX-UHFFFAOYSA-N 0.000 claims description 5
- CKINLPPNOXBMMZ-UHFFFAOYSA-N N-[2-[4-(1H-benzimidazol-2-yloxy)phenyl]ethyl]-2-cyclohexylethanamine Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CCNCCC1CCCCC1 CKINLPPNOXBMMZ-UHFFFAOYSA-N 0.000 claims description 5
- HCRZLGCIXFVSGX-UHFFFAOYSA-N OC(=O)CNCC(=O)C1CCN(CCOc2ccc(Oc3nc4ccccc4s3)cc2)CC1 Chemical compound OC(=O)CNCC(=O)C1CCN(CCOc2ccc(Oc3nc4ccccc4s3)cc2)CC1 HCRZLGCIXFVSGX-UHFFFAOYSA-N 0.000 claims description 5
- RJMLMGFIAISZQE-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1C(=O)N1CCCC1 RJMLMGFIAISZQE-UHFFFAOYSA-N 0.000 claims description 5
- NTOXQUBAGYBHEG-UHFFFAOYSA-N [1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NTOXQUBAGYBHEG-UHFFFAOYSA-N 0.000 claims description 5
- PTPDJDATJRANLS-UHFFFAOYSA-N [1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 PTPDJDATJRANLS-UHFFFAOYSA-N 0.000 claims description 5
- TYUINOFAKUGLOA-UHFFFAOYSA-N [1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-3-yl]methanol Chemical compound C1C(CO)CCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 TYUINOFAKUGLOA-UHFFFAOYSA-N 0.000 claims description 5
- BMZRZMPVKLUBNR-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BMZRZMPVKLUBNR-UHFFFAOYSA-N 0.000 claims description 5
- OWUKUHRUWJWPLR-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-4-phenylpiperidine-4-carboxylate Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1(C(=O)OCC)C1=CC=CC=C1 OWUKUHRUWJWPLR-UHFFFAOYSA-N 0.000 claims description 5
- YFKRUZPIKGRERG-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YFKRUZPIKGRERG-UHFFFAOYSA-N 0.000 claims description 5
- RXQCBZKSQRTWHU-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RXQCBZKSQRTWHU-UHFFFAOYSA-N 0.000 claims description 5
- OZXVXVTYNDRZCK-UHFFFAOYSA-N ethyl 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 OZXVXVTYNDRZCK-UHFFFAOYSA-N 0.000 claims description 5
- FWLUNXGSLLZGCE-UHFFFAOYSA-N ethyl 3-[[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidine-4-carbonyl]amino]propanoate Chemical compound C1CC(C(=O)NCCC(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 FWLUNXGSLLZGCE-UHFFFAOYSA-N 0.000 claims description 5
- YDSNEVLFPYRGGL-UHFFFAOYSA-N methyl 1-[2-[4-(1,3-benzoxazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2O1 YDSNEVLFPYRGGL-UHFFFAOYSA-N 0.000 claims description 5
- FYJLYIYGBKVEGO-UHFFFAOYSA-N methyl 1-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 FYJLYIYGBKVEGO-UHFFFAOYSA-N 0.000 claims description 5
- CWXLZFJMDHQVTK-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-2-phenylacetamide Chemical compound C1CN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)CC1=CC=CC=C1 CWXLZFJMDHQVTK-UHFFFAOYSA-N 0.000 claims description 5
- JAEBDNUIPXAQCD-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-2-phenylacetamide Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)CC1=CC=CC=C1 JAEBDNUIPXAQCD-UHFFFAOYSA-N 0.000 claims description 5
- VCIPSOKMDORQAZ-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-2-phenylacetamide Chemical compound C1CN(CCOC=2C=CC(OC=3OC4=CC=CC=C4N=3)=CC=2)CCC1NC(=O)CC1=CC=CC=C1 VCIPSOKMDORQAZ-UHFFFAOYSA-N 0.000 claims description 5
- FIWPKUWTMFDONG-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(OCCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2S1 FIWPKUWTMFDONG-UHFFFAOYSA-N 0.000 claims description 5
- QYPBHSJVIGZICE-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)propan-1-amine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCC)CC1CC1 QYPBHSJVIGZICE-UHFFFAOYSA-N 0.000 claims description 5
- NTEKFVIMRQKTFZ-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(CCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2S1 NTEKFVIMRQKTFZ-UHFFFAOYSA-N 0.000 claims description 5
- VLOWRXOWQAQHFS-UHFFFAOYSA-N n-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-n-(cyclopropylmethyl)propan-1-amine Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1OCCN(CCC)CC1CC1 VLOWRXOWQAQHFS-UHFFFAOYSA-N 0.000 claims description 5
- RMZWAMRCOZZAKM-UHFFFAOYSA-N n-[2-[4-(1,3-benzoxazol-2-yloxy)phenoxy]ethyl]-n-ethylbutan-1-amine Chemical compound C1=CC(OCCN(CC)CCCC)=CC=C1OC1=NC2=CC=CC=C2O1 RMZWAMRCOZZAKM-UHFFFAOYSA-N 0.000 claims description 5
- NFDQWFPURHXXMM-UHFFFAOYSA-N n-[2-[4-(1,3-benzoxazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)propan-1-amine Chemical compound C=1C=C(OC=2OC3=CC=CC=C3N=2)C=CC=1CCN(CCC)CC1CC1 NFDQWFPURHXXMM-UHFFFAOYSA-N 0.000 claims description 5
- NYUXYLIKMOXXIP-UHFFFAOYSA-N n-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)propan-1-amine Chemical compound C=1C=C(OC=2NC3=CC=CC=C3N=2)C=CC=1CCN(CCC)CC1CC1 NYUXYLIKMOXXIP-UHFFFAOYSA-N 0.000 claims description 5
- VSHBSVJWEDWHDZ-UHFFFAOYSA-N n-[2-[4-(1h-benzimidazol-2-yloxy)phenyl]ethyl]-n-butylbutan-1-amine Chemical compound C1=CC(CCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2N1 VSHBSVJWEDWHDZ-UHFFFAOYSA-N 0.000 claims description 5
- FAIMVYCQWFVUID-UHFFFAOYSA-N n-ethyl-n-[2-[4-(1-methylbenzimidazol-2-yl)oxyphenyl]ethyl]cyclohexanamine Chemical compound C=1C=C(OC=2N(C3=CC=CC=C3N=2)C)C=CC=1CCN(CC)C1CCCCC1 FAIMVYCQWFVUID-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
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- MVOUDSMIRONHKB-UHFFFAOYSA-N [1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 MVOUDSMIRONHKB-UHFFFAOYSA-N 0.000 claims description 4
- IVKUGUCBCYQYLC-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-(5-methylpyrazin-2-yl)methanone Chemical compound C1=NC(C)=CN=C1C(=O)N1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 IVKUGUCBCYQYLC-UHFFFAOYSA-N 0.000 claims description 4
- RHNNPEULEGUXQI-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-(oxolan-2-yl)methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CCCO1 RHNNPEULEGUXQI-UHFFFAOYSA-N 0.000 claims description 4
- KVUYDYZEJDFNHJ-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-(oxolan-3-yl)methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CCOC1 KVUYDYZEJDFNHJ-UHFFFAOYSA-N 0.000 claims description 4
- RHNNPEULEGUXQI-OAQYLSRUSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-[(2r)-oxolan-2-yl]methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)[C@H]1CCCO1 RHNNPEULEGUXQI-OAQYLSRUSA-N 0.000 claims description 4
- RHNNPEULEGUXQI-NRFANRHFSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-[(2s)-oxolan-2-yl]methanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)[C@@H]1CCCO1 RHNNPEULEGUXQI-NRFANRHFSA-N 0.000 claims description 4
- HFVJQHOAAGUSCE-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-cyclopropylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1CC1 HFVJQHOAAGUSCE-UHFFFAOYSA-N 0.000 claims description 4
- SRXPOGKYEYCPMQ-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-morpholin-4-ylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)N1CCOCC1 SRXPOGKYEYCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- JTHRNERQCUBCFR-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-pyridin-3-ylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1=CC=CN=C1 JTHRNERQCUBCFR-UHFFFAOYSA-N 0.000 claims description 4
- UHNQARHEORQPIK-UHFFFAOYSA-N [4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-pyridin-4-ylmethanone Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCN1C(=O)C1=CC=NC=C1 UHNQARHEORQPIK-UHFFFAOYSA-N 0.000 claims description 4
- 230000002255 enzymatic effect Effects 0.000 claims description 4
- BIZVFRGJJTYCDX-UHFFFAOYSA-N ethyl 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-5-oxopyrrolidine-2-carboxylate Chemical compound CCOC(=O)C1CCC(=O)N1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 BIZVFRGJJTYCDX-UHFFFAOYSA-N 0.000 claims description 4
- YPBOSXISLJYDLJ-UHFFFAOYSA-N ethyl 1-[3-[4-(1,3-benzothiazol-2-yloxy)phenyl]propyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 YPBOSXISLJYDLJ-UHFFFAOYSA-N 0.000 claims description 4
- AFPNCILRTCEMCE-UHFFFAOYSA-N ethyl 2-[[2-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-2-oxoethyl]amino]acetate Chemical compound C1CC(C(=O)CNCC(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 AFPNCILRTCEMCE-UHFFFAOYSA-N 0.000 claims description 4
- MMEFFRGZDFLOAC-UHFFFAOYSA-N ethyl 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]butanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCC(=O)OCC)CC1CC1 MMEFFRGZDFLOAC-UHFFFAOYSA-N 0.000 claims description 4
- KUZXJGBTRMWOEO-UHFFFAOYSA-N ethyl 4-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperazine-1-carbonyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C(=O)N1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 KUZXJGBTRMWOEO-UHFFFAOYSA-N 0.000 claims description 4
- XTGUVGAFFDTRHE-UHFFFAOYSA-N ethyl 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]octanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCCCC(=O)OCC)C1CC1 XTGUVGAFFDTRHE-UHFFFAOYSA-N 0.000 claims description 4
- JHAVVDDIZYSOCI-UHFFFAOYSA-N methyl 2-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperazin-1-yl]-2-oxoacetate Chemical compound C1CN(C(=O)C(=O)OC)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 JHAVVDDIZYSOCI-UHFFFAOYSA-N 0.000 claims description 4
- HNCFYDRWWPOACC-UHFFFAOYSA-N methyl 5-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]pentanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCC(=O)OC)C1CC1 HNCFYDRWWPOACC-UHFFFAOYSA-N 0.000 claims description 4
- JUGPWEBBIASSJY-UHFFFAOYSA-N methyl N'-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-N-cyanocarbamimidate Chemical compound S1C(=NC2=C1C=CC=C2)OC1=CC=C(C=C1)CCN1CCC(CC1)NC(OC)=NC#N JUGPWEBBIASSJY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- XJNRXSAAVCVMPH-UHFFFAOYSA-N n-(benzenesulfonyl)-1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carboxamide;trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1C(=O)NS(=O)(=O)C1=CC=CC=C1 XJNRXSAAVCVMPH-UHFFFAOYSA-N 0.000 claims description 4
- CNJOEMGIFXKJRC-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-4-chloro-n-cyclopropylbenzenesulfonamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N(C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1)C1CC1 CNJOEMGIFXKJRC-UHFFFAOYSA-N 0.000 claims description 4
- GVHQWMPVVZCPSH-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-methylacetamide Chemical compound C1CC(N(C)C(C)=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GVHQWMPVVZCPSH-UHFFFAOYSA-N 0.000 claims description 4
- RGIJQBLXCIRDIX-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-methylmethanesulfonamide Chemical compound C1CC(N(C)S(C)(=O)=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RGIJQBLXCIRDIX-UHFFFAOYSA-N 0.000 claims description 4
- HGXCLIZMBKPLLN-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]formamide Chemical compound C1CC(NC=O)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 HGXCLIZMBKPLLN-UHFFFAOYSA-N 0.000 claims description 4
- GUKGFCRRJHTNDV-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-(cyclopropylmethyl)-3-(2h-tetrazol-5-yl)propan-1-amine Chemical compound N1=NNN=C1CCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)CC1CC1 GUKGFCRRJHTNDV-UHFFFAOYSA-N 0.000 claims description 4
- PSNFNDVIDUOKFR-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-ethylcyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CC)C1CC1 PSNFNDVIDUOKFR-UHFFFAOYSA-N 0.000 claims description 4
- PGNCKSDHQSASSK-UHFFFAOYSA-N n-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]cyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCNC1CC1 PGNCKSDHQSASSK-UHFFFAOYSA-N 0.000 claims description 4
- AFSRMHKPXBPUNT-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(cyclopropylmethyl)amino]propyl]acetamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNC(=O)C)CC1CC1 AFSRMHKPXBPUNT-UHFFFAOYSA-N 0.000 claims description 4
- ARJJEYABAHZLNG-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]-2-methylpropanamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNC(=O)C(C)C)C1CC1 ARJJEYABAHZLNG-UHFFFAOYSA-N 0.000 claims description 4
- RNQICXAMMRPUDL-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCCN(C1CC1)CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RNQICXAMMRPUDL-UHFFFAOYSA-N 0.000 claims description 4
- CKNNIXXSXJPDFK-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]acetamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNC(=O)C)C1CC1 CKNNIXXSXJPDFK-UHFFFAOYSA-N 0.000 claims description 4
- LIYJFLBFLXWRQB-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]methanesulfonamide Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCNS(=O)(=O)C)C1CC1 LIYJFLBFLXWRQB-UHFFFAOYSA-N 0.000 claims description 4
- OGPDRHICJZQAJN-UHFFFAOYSA-N n-[3-[4-(1,3-benzoxazol-2-yloxy)phenyl]propyl]-n-butylbutan-1-amine Chemical compound C1=CC(CCCN(CCCC)CCCC)=CC=C1OC1=NC2=CC=CC=C2O1 OGPDRHICJZQAJN-UHFFFAOYSA-N 0.000 claims description 4
- XPARKDXSLNZXAB-UHFFFAOYSA-N phenyl n'-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-cyanocarbamimidate Chemical compound C1CN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CCC1NC(=NC#N)OC1=CC=CC=C1 XPARKDXSLNZXAB-UHFFFAOYSA-N 0.000 claims description 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940080818 propionamide Drugs 0.000 claims description 4
- VULLJZNHYDJBOE-UHFFFAOYSA-N tert-butyl 4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]tetrazol-5-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NN=NN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 VULLJZNHYDJBOE-UHFFFAOYSA-N 0.000 claims description 4
- KEPAIVQLVJNZDB-UHFFFAOYSA-N tert-butyl 4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carbonyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 KEPAIVQLVJNZDB-UHFFFAOYSA-N 0.000 claims description 4
- GVXWUAZHXAOVSW-UHFFFAOYSA-N tert-butyl n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]-n-methylcarbamate Chemical compound C1CC(N(C)C(=O)OC(C)(C)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 GVXWUAZHXAOVSW-UHFFFAOYSA-N 0.000 claims description 4
- RLKZWNLELPUMTF-UHFFFAOYSA-N tert-butyl n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 RLKZWNLELPUMTF-UHFFFAOYSA-N 0.000 claims description 4
- HOYVUZXQBKNTGW-UHFFFAOYSA-N 1-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]-5-oxopyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CCC(=O)N1C1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 HOYVUZXQBKNTGW-UHFFFAOYSA-N 0.000 claims description 3
- MTCQVADOSPRCJN-UHFFFAOYSA-N 1-[1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound O=C1CCCN1C1CCN(CCOC=2C=CC(OC=3NC4=CC=CC=C4N=3)=CC=2)CC1 MTCQVADOSPRCJN-UHFFFAOYSA-N 0.000 claims description 3
- BNSUSWMQGUZFKD-UHFFFAOYSA-N 1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-n-methylsulfonylpiperidine-4-carboxamide;trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.C1CC(C(=O)NS(=O)(=O)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BNSUSWMQGUZFKD-UHFFFAOYSA-N 0.000 claims description 3
- YBVBCWYCIKAVFN-UHFFFAOYSA-N 1-[4-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidine-4-carbonyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(=O)C1CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 YBVBCWYCIKAVFN-UHFFFAOYSA-N 0.000 claims description 3
- ZFOMZVAPHUXJNT-UHFFFAOYSA-N 2-[4-(2-piperidin-1-ylethoxy)phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1CCCCC1 ZFOMZVAPHUXJNT-UHFFFAOYSA-N 0.000 claims description 3
- FMLVCMDYJKHZIN-UHFFFAOYSA-N 2-[4-[2-(5-piperidin-4-yltetrazol-1-yl)ethoxy]phenoxy]-1,3-benzothiazole Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1N=NN=C1C1CCNCC1 FMLVCMDYJKHZIN-UHFFFAOYSA-N 0.000 claims description 3
- YGWNKMJGFVIHCT-UHFFFAOYSA-N C(C)C1(C(C1)CN(C1CC1)CCC1=CC=C(C=C1)OC=1SC2=C(N=1)C=CC=C2)C(=O)O Chemical compound C(C)C1(C(C1)CN(C1CC1)CCC1=CC=C(C=C1)OC=1SC2=C(N=1)C=CC=C2)C(=O)O YGWNKMJGFVIHCT-UHFFFAOYSA-N 0.000 claims description 3
- GVOKUSYFPVQDLH-UHFFFAOYSA-N N1(CCCC1)CCCC1=CC=C(OC=2OC3=C(N=2)C=CC=C3)C=C1 Chemical compound N1(CCCC1)CCCC1=CC=C(OC=2OC3=C(N=2)C=CC=C3)C=C1 GVOKUSYFPVQDLH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- DHEMYZSPCMFSFY-UHFFFAOYSA-N n-[1-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]piperidin-4-yl]methanesulfonamide Chemical compound C1CC(NS(=O)(=O)C)CCN1CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 DHEMYZSPCMFSFY-UHFFFAOYSA-N 0.000 claims description 3
- RJNBKACGGIPZSI-UHFFFAOYSA-N n-[3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]propyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCCN(CCC=1C=CC(OC=2SC3=CC=CC=C3N=2)=CC=1)C1CC1 RJNBKACGGIPZSI-UHFFFAOYSA-N 0.000 claims description 3
- CBDDJDKBBAWXOF-UHFFFAOYSA-N 4-[4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]piperazin-1-yl]phenol Chemical compound C1=CC(O)=CC=C1N1CCN(CCOC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 CBDDJDKBBAWXOF-UHFFFAOYSA-N 0.000 claims description 2
- MMMXMWIHIHNYFE-UHFFFAOYSA-N ethyl 1-[2-[4-(1h-benzimidazol-2-yloxy)phenoxy]ethyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCOC(C=C1)=CC=C1OC1=NC2=CC=CC=C2N1 MMMXMWIHIHNYFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 6
- PGDDIFWXNLMSQQ-UHFFFAOYSA-N 2-[[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1CN(C1CC1)CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 PGDDIFWXNLMSQQ-UHFFFAOYSA-N 0.000 claims 4
- CXJOBTJPCAHMGE-UHFFFAOYSA-N 3-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-(1-methylpiperidin-4-yl)amino]propanoic acid Chemical compound C1CN(C)CCC1N(CCC(O)=O)CCC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CXJOBTJPCAHMGE-UHFFFAOYSA-N 0.000 claims 3
- XHNDRMFJEUDOIJ-UHFFFAOYSA-N 4-[2-[4-(1,3-benzothiazol-2-yloxy)phenoxy]ethyl]morpholine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1OCCN1CCOCC1 XHNDRMFJEUDOIJ-UHFFFAOYSA-N 0.000 claims 3
- XUTNRGXSOVWRQJ-UHFFFAOYSA-N N1(CCCCCC1)CCOC1=CC=C(ON2C(=NC3=C2C=CC=C3)C(=O)N)C=C1 Chemical compound N1(CCCCCC1)CCOC1=CC=C(ON2C(=NC3=C2C=CC=C3)C(=O)N)C=C1 XUTNRGXSOVWRQJ-UHFFFAOYSA-N 0.000 claims 3
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 3
- CPRMTRQPCBTSCA-UHFFFAOYSA-N ethyl 6-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl-cyclopropylamino]hexanoate Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CCN(CCCCCC(=O)OCC)C1CC1 CPRMTRQPCBTSCA-UHFFFAOYSA-N 0.000 claims 3
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 3
- WJZIPMQUKSTHLV-UHFFFAOYSA-N 2-ethyldecanoic acid Chemical compound CCCCCCCCC(CC)C(O)=O WJZIPMQUKSTHLV-UHFFFAOYSA-N 0.000 claims 2
- LHSXKZYJSBXKAB-UHFFFAOYSA-N 8-[2-[4-(1,3-benzothiazol-2-yloxy)phenyl]ethyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound N1C(=O)NC(=O)C11CCN(CCC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 LHSXKZYJSBXKAB-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- XLWFVDTXBLVKSV-UHFFFAOYSA-N CC(CCCCN(CCC(C=C1)=CC=C1OC1=NC(C=CC=C2)=C2S1)C1CC1)S(N)(=O)=O Chemical compound CC(CCCCN(CCC(C=C1)=CC=C1OC1=NC(C=CC=C2)=C2S1)C1CC1)S(N)(=O)=O XLWFVDTXBLVKSV-UHFFFAOYSA-N 0.000 claims 2
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 claims 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
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- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| CN101189012A (zh) * | 2005-03-31 | 2008-05-28 | 詹森药业有限公司 | 苯基和吡啶基lta4h调节剂 |
| ES2523565T3 (es) | 2005-04-13 | 2014-11-27 | Astex Therapeutics Limited | Derivados de hidroxibenzamida y sus usos como inhibidores de la hsp90 |
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| UA101943C2 (ru) * | 2005-09-21 | 2013-05-27 | Декод Дженетикс Ехф | Биарилзамещенные гетероциклические ингибиторы lta4h для лечения воспаления |
| AU2006333522A1 (en) * | 2005-12-21 | 2007-07-12 | Decode Genetics, Ehf. | Biaryl nitrogen heterocycle inhibitors of LTA4H for treating inflammation |
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| CA2634701C (en) | 2005-12-21 | 2014-07-29 | Decode Genetics Ehf | Biaryl substituted nitrogen containing heterocycle inhibitors of lta4h for treating inflammation |
| HUE031972T2 (en) * | 2005-12-29 | 2017-08-28 | Celtaxsys Inc | Diamine derivatives as inhibitors of leukotriene a4 hydrolase |
| JP2009525269A (ja) * | 2006-01-30 | 2009-07-09 | ユーロ−セルティーク エス.エイ. | カルシウムチャネルブロッカーとしての環状尿素化合物 |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| US7951829B2 (en) * | 2006-05-03 | 2011-05-31 | Janssen Pharmaceutica Nv | Benzimidazole modulators of VR1 |
| US8299095B2 (en) * | 2006-06-16 | 2012-10-30 | H. Lundbeck A/S | Crystalline forms of 4-[2-(4-methylphenylsulfanyl)-phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition and uses thereof |
| US7728032B2 (en) * | 2006-08-04 | 2010-06-01 | Decode Genetics Ehf | Phenoxymethylalkyne inhibitors of LTA4H for treating inflammation |
| WO2008019302A1 (en) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Pyrazolylphenyl and pyrrolylphenyl inhibitors of lta4h for treating inflammation |
| EP2066800A2 (en) * | 2006-08-04 | 2009-06-10 | Decode Genetics EHF | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5518478B2 (ja) | 2006-10-12 | 2014-06-11 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| WO2008044029A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
| US20100120807A1 (en) * | 2007-03-08 | 2010-05-13 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
| WO2008120710A1 (ja) * | 2007-03-30 | 2008-10-09 | Panasonic Electric Works Co., Ltd. | 活動強度計 |
| UY31443A1 (es) * | 2007-10-31 | 2009-04-30 | Diaminas en puente o fusionadas sustituidas con arilo como moduladores de leucotrieno a4 hidrolasa | |
| US20090176785A1 (en) * | 2007-11-16 | 2009-07-09 | Abbott Laboratories | Method of treating arthritis |
| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| MX2010011154A (es) * | 2008-04-11 | 2010-12-21 | Janssen Pharmaceutica Nv | Tiazolopiridin-2-iloxi-fenilo y tiazolopirazin-2-iloxifenilaminas como moduladores de la leucotrieno a4 hidrolasa. |
| PT2294066E (pt) | 2008-04-28 | 2014-11-21 | Janssen Pharmaceutica Nv | Benzoimidazoles como inibidores da prolil-hidroxilase |
| AU2010249041B2 (en) | 2009-05-14 | 2014-11-13 | Janssen Pharmaceutica Nv | Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene A4 hydrolase |
| CN102442962A (zh) * | 2010-11-10 | 2012-05-09 | 江苏德峰药业有限公司 | 1-烷基四氮唑的生产方法 |
| CN102442961A (zh) * | 2010-11-10 | 2012-05-09 | 江苏德峰药业有限公司 | 1-甲基四氮唑的生产方法 |
| EP2776023B1 (en) | 2011-10-25 | 2016-03-09 | Janssen Pharmaceutica, N.V. | Meglumine salt formulations of 1-(5,6-dichloro-1h-benzo[d]imidazol-2-yl)-1h-pyrazole-4-carboxylic acid |
| CA2905340C (en) | 2013-03-12 | 2022-05-31 | Celtaxsys, Inc. | Low dose oral formulations of acebilustat |
| BR112015022226A2 (pt) | 2013-03-14 | 2017-07-18 | Celtaxsys Inc | inibidores de leucotrieno a4 hidrolase |
| KR20150131211A (ko) * | 2013-03-14 | 2015-11-24 | 켈탁시스, 인코퍼레이티드 | 류코트라이엔 a4 가수분해효소의 저해제 |
| BR112015022864A8 (pt) | 2013-03-14 | 2019-11-26 | Celtaxsys Inc | composto, composição farmacêutica e uso dos mesmos |
| WO2015094902A1 (en) * | 2013-12-17 | 2015-06-25 | Eli Lilly And Company | Phenoxyethyl cyclic amine derivatives and their activity as ep4 receptor modulators |
| EP3233077A4 (en) | 2014-12-19 | 2018-08-08 | The Broad Institute Inc. | Dopamine d2 receptor ligands |
| EP3233799B1 (en) | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| RU2715897C2 (ru) | 2015-06-09 | 2020-03-04 | Эббви Инк. | Модуляторы ядерных рецепторов |
| IL267352B2 (en) | 2016-12-21 | 2023-10-01 | Hoffmann La Roche | Method for in vitro glycoengineering of antibodies |
| WO2018114878A1 (en) | 2016-12-21 | 2018-06-28 | F. Hoffmann-La Roche Ag | Re-use of enzymes in in vitro glycoengineering of antibodies |
| CN107663192B (zh) * | 2017-11-03 | 2019-05-10 | 梯尔希(南京)药物研发有限公司 | 一种雷贝拉唑杂质的制备方法 |
| JP7386815B2 (ja) | 2018-05-31 | 2023-11-27 | セルタクシー、エルエルシー | 呼吸器疾患患者の肺増悪を軽減する方法 |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN113784713A (zh) * | 2019-01-11 | 2021-12-10 | 纳吉斯制药股份有限公司 | 白三烯合成抑制剂 |
| CN110026557B (zh) * | 2019-05-28 | 2021-08-27 | 南方科技大学 | 一种混合固体颗粒重熔的直写装置及成型方法 |
| TW202235071A (zh) * | 2020-11-19 | 2022-09-16 | 美商特洛治療公司 | 小分子化合物及組成物 |
| US11932630B2 (en) * | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
| CN113683491A (zh) * | 2021-09-01 | 2021-11-23 | 王传良 | 一种4-(2-溴乙基)苯酚的制备方法 |
| CN113735798B (zh) * | 2021-09-27 | 2022-07-12 | 安徽美致诚药业有限公司 | 一种盐酸罗沙替丁醋酸酯的制备方法 |
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| SU1681728A3 (ru) * | 1988-05-24 | 1991-09-30 | Пфайзер Инк. (Фирма) | Способ получени производных N-(бензтиазолил-2)амидов бензойной или тиазол-4-карбоновой кислоты |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4873346A (en) * | 1985-09-20 | 1989-10-10 | The Upjohn Company | Substituted benzothiazoles, benzimidazoles, and benzoxazoles |
| DK171349B1 (da) * | 1986-11-14 | 1996-09-16 | Hoffmann La Roche | Tetrahydronaphthalenderivater, fremgangsmåde til fremstilling deraf, lægemidler indeholdende forbindelserne samt anvendelse af forbindelserne til fremstilling af lægemidler |
| IT1240598B (it) * | 1990-03-13 | 1993-12-17 | Mini Ricerca Scient Tecnolog | Derivati amminici ad azione antifungina |
| US5585492A (en) * | 1994-10-11 | 1996-12-17 | G. D. Searle & Co. | LTA4 Hydrolase inhibitors |
| IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
| US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
| US5925654A (en) * | 1997-03-12 | 1999-07-20 | G.D. Searle & Co. | LTA4 , hydrolase inhibitors |
| EP1062216A1 (en) * | 1998-02-25 | 2000-12-27 | Genetics Institute, Inc. | Inhibitors of phospholipase a2 |
| US6514964B1 (en) * | 1999-09-27 | 2003-02-04 | Amgen Inc. | Fused cycloheptane and fused azacycloheptane compounds and their methods of use |
| US20040110757A1 (en) * | 2002-03-21 | 2004-06-10 | Thomas Arrhenius | Flt-1 ligands and their uses in the treatment of diseases regulatable by angiogenesis |
| CN100591679C (zh) * | 2003-07-28 | 2010-02-24 | 詹森药业有限公司 | 苯并咪唑、苯并噻唑和苯并唑衍生物及其作为lta4h调节剂的应用 |
| US7541466B2 (en) * | 2003-12-23 | 2009-06-02 | Genzyme Corporation | Tetrahydroisoquinoline derivatives for treating protein trafficking diseases |
| HRP20160373T1 (hr) * | 2005-03-16 | 2016-05-06 | Meda Pharma Gmbh & Co. Kg | Kombinacija antikolinergika i antagonista leukotrien receptora za liječenje bolesti dišnog sustava |
| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SU1681728A3 (ru) * | 1988-05-24 | 1991-09-30 | Пфайзер Инк. (Фирма) | Способ получени производных N-(бензтиазолил-2)амидов бензойной или тиазол-4-карбоновой кислоты |
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