CA2550257A1 - 1-akan-2-ol substituted piperazine and piperidine compounds - Google Patents

Info

Publication number

CA2550257A1

CA2550257A1 CA002550257A CA2550257A CA2550257A1 CA 2550257 A1 CA2550257 A1 CA 2550257A1 CA 002550257 A CA002550257 A CA 002550257A CA 2550257 A CA2550257 A CA 2550257A CA 2550257 A1 CA2550257 A1 CA 2550257A1

Authority

CA

Canada

Prior art keywords

yloxy

methylbenzothiazol

piperazinyl

propyl

hydroxy

Prior art date

2003-12-18

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title description 5
• 150000004885 piperazines Chemical class 0.000 title description 3
• 150000003053 piperidines Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 259
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
• 201000010099 disease Diseases 0.000 claims abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
• 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 10
• 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 7
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 7
• 206010022562 Intermittent claudication Diseases 0.000 claims abstract description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 6
• 208000021156 intermittent vascular claudication Diseases 0.000 claims abstract description 6
• 208000010125 myocardial infarction Diseases 0.000 claims abstract description 6
• 206010003130 Arrhythmia supraventricular Diseases 0.000 claims abstract description 5
• 208000007718 Stable Angina Diseases 0.000 claims abstract description 5
• 206010047281 Ventricular arrhythmia Diseases 0.000 claims abstract description 5
• 206010002388 Angina unstable Diseases 0.000 claims abstract description 4
• 208000007814 Unstable Angina Diseases 0.000 claims abstract description 4
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims abstract description 4
• -1 azolidine-2,5-dionyl moiety Chemical group 0.000 claims description 138
• 125000004193 piperazinyl group Chemical group 0.000 claims description 137
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• 150000001412 amines Chemical class 0.000 claims description 64
• 125000001072 heteroaryl group Chemical group 0.000 claims description 46
• 238000000034 method Methods 0.000 claims description 44
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 150000002431 hydrogen Chemical class 0.000 claims description 19
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 17
• 125000002947 alkylene group Chemical group 0.000 claims description 15
• HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000003107 substituted aryl group Chemical group 0.000 claims description 8
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
• USQYEHICAINAAI-HXUWFJFHSA-N (2r)-1-[4-(4-cyclopentyloxybutyl)piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCCC1 USQYEHICAINAAI-HXUWFJFHSA-N 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• FCOVEHXMSLZUFC-LJQANCHMSA-N (2r)-1-[4-[2-(4-chlorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(Cl)C=C1 FCOVEHXMSLZUFC-LJQANCHMSA-N 0.000 claims description 4
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 4
• YTFYLKVQTIMNDL-RIBGEGAISA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-(1,2,3,4-tetrahydronaphthalen-1-yloxy)butyl]piperazin-1-yl]propan-2-ol Chemical compound C1CCC2=CC=CC=C2C1OCCCCN(CC1)CCN1C[C@@H](O)COC1=CC=C(SC(C)=N2)C2=C1 YTFYLKVQTIMNDL-RIBGEGAISA-N 0.000 claims description 3
• ZLUCCAXVBWMFNA-RUZDIDTESA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-(5,6,7,8-tetrahydronaphthalen-2-yloxy)butyl]piperazin-1-yl]propan-2-ol Chemical compound C1CCCC2=CC(OCCCCN3CCN(CC3)C[C@@H](O)COC=3C=C4N=C(SC4=CC=3)C)=CC=C21 ZLUCCAXVBWMFNA-RUZDIDTESA-N 0.000 claims description 3
• VRJPOOAFZYANCT-LJQANCHMSA-N (2r)-1-[4-(4-cyclobutyloxybutyl)piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCC1 VRJPOOAFZYANCT-LJQANCHMSA-N 0.000 claims description 3
• XQVIZOXXEBNQFM-XMMPIXPASA-N (2r)-1-[4-[4-(2,3-dihydro-1h-inden-2-yloxy)butyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1C2=CC=CC=C2CC1OCCCCN(CC1)CCN1C[C@@H](O)COC1=CC=C(SC(C)=N2)C2=C1 XQVIZOXXEBNQFM-XMMPIXPASA-N 0.000 claims description 3
• DXWNHPIOSOCWNR-LCQOSCCDSA-N 1-(4-bromophenyl)-3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(Br)C=C1 DXWNHPIOSOCWNR-LCQOSCCDSA-N 0.000 claims description 3
• TUVWTBJCRUAICB-UFUCKMQHSA-N 1-(4-tert-butylphenyl)-3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(C(C)(C)C)C=C1 TUVWTBJCRUAICB-UFUCKMQHSA-N 0.000 claims description 3
• CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 3
• DDVQWTPOSIBXOO-ZZWBGTBQSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-[4-(trifluoromethoxy)phenyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(OC(F)(F)F)C=C1 DDVQWTPOSIBXOO-ZZWBGTBQSA-N 0.000 claims description 3
• GILJWKOYDVNXIZ-LCQOSCCDSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-[4-(trifluoromethyl)phenyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(C(F)(F)F)C=C1 GILJWKOYDVNXIZ-LCQOSCCDSA-N 0.000 claims description 3
• LWWCXHIXJNVTSN-VGAJERRHSA-N 3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]-1-phenylpyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=CC=C1 LWWCXHIXJNVTSN-VGAJERRHSA-N 0.000 claims description 3
• ZBAFSRVWQIWARD-HXUWFJFHSA-N C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNC(=O)C1=CC=C(Cl)C=C1 Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNC(=O)C1=CC=C(Cl)C=C1 ZBAFSRVWQIWARD-HXUWFJFHSA-N 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 230000006378 damage Effects 0.000 claims description 3
• LYINKTVZUSKQEQ-UHFFFAOYSA-N furan-3-one Chemical compound O=C1COC=C1 LYINKTVZUSKQEQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 208000014674 injury Diseases 0.000 claims description 3
• 230000035939 shock Effects 0.000 claims description 3
• 210000002027 skeletal muscle Anatomy 0.000 claims description 3
• 230000008733 trauma Effects 0.000 claims description 3
• RJEDNSMPHIARKY-HXUWFJFHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-(3-phenoxypropyl)piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCOC1=CC=CC=C1 RJEDNSMPHIARKY-HXUWFJFHSA-N 0.000 claims description 2
• PXXCLIPMCDDJJV-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-[4-(trifluoromethyl)phenoxy]ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(C(F)(F)F)C=C1 PXXCLIPMCDDJJV-LJQANCHMSA-N 0.000 claims description 2
• MFFJUQVPIZKLCM-ATKRNPRHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-[4-(trifluoromethyl)cyclohexyl]oxybutyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCC(C(F)(F)F)CC1 MFFJUQVPIZKLCM-ATKRNPRHSA-N 0.000 claims description 2
• ZGQUGDSVCSKSRS-OAQYLSRUSA-N (2r)-1-[4-(4-cyclohexyloxybutyl)piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCCCC1 ZGQUGDSVCSKSRS-OAQYLSRUSA-N 0.000 claims description 2
• PFMDEVGDEAHHHN-LJQANCHMSA-N (2r)-1-[4-[2-(2-methoxyphenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound COC1=CC=CC=C1OCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 PFMDEVGDEAHHHN-LJQANCHMSA-N 0.000 claims description 2
• WEFOATARQOGEPR-QGZVFWFLSA-N (2r)-1-[4-[2-(4-bromo-3-chlorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(Br)C(Cl)=C1 WEFOATARQOGEPR-QGZVFWFLSA-N 0.000 claims description 2
• BEVFHHAVOBHUMN-LJQANCHMSA-N (2r)-1-[4-[2-(4-fluorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(F)C=C1 BEVFHHAVOBHUMN-LJQANCHMSA-N 0.000 claims description 2
• CGBXLNUGMNCNTB-LJQANCHMSA-N (2r)-1-[4-[2-(4-methoxyphenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C1=CC(OC)=CC=C1OCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 CGBXLNUGMNCNTB-LJQANCHMSA-N 0.000 claims description 2
• QYFGVPIQAZCOAF-HXUWFJFHSA-N (2r)-1-[4-[3-(4-fluorophenoxy)propyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCOC1=CC=C(F)C=C1 QYFGVPIQAZCOAF-HXUWFJFHSA-N 0.000 claims description 2
• SJWJDFCBAIMPAS-DENIHFKCSA-N (3r)-1-(2-fluorophenyl)-3-[[1-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperidin-4-yl]amino]pyrrolidin-2-one Chemical compound C([C@H](C1=O)NC2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=CC=C1F SJWJDFCBAIMPAS-DENIHFKCSA-N 0.000 claims description 2
• NCAWZBIYOSKOGR-IFMALSPDSA-N (3r)-1-(4-chlorophenyl)-3-[[1-[(2r)-3-(2-fluorophenoxy)-2-hydroxypropyl]piperidin-4-yl]amino]pyrrolidin-2-one Chemical compound C([C@H](O)CN1CCC(CC1)N[C@H]1C(N(CC1)C=1C=CC(Cl)=CC=1)=O)OC1=CC=CC=C1F NCAWZBIYOSKOGR-IFMALSPDSA-N 0.000 claims description 2
• UUHMQYDKZGABNM-FYYLOGMGSA-N (3r)-1-(4-fluorophenyl)-3-[[1-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperidin-4-yl]amino]pyrrolidin-2-one Chemical compound C([C@H](C1=O)NC2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=C(F)C=C1 UUHMQYDKZGABNM-FYYLOGMGSA-N 0.000 claims description 2
• QZGPXSCJMVWRIU-WIYYLYMNSA-N (3r)-3-[[1-[(2r)-3-(2-fluorophenoxy)-2-hydroxypropyl]piperidin-4-yl]amino]-1-(2-fluorophenyl)pyrrolidin-2-one Chemical compound C([C@H](O)CN1CCC(CC1)N[C@H]1C(N(CC1)C=1C(=CC=CC=1)F)=O)OC1=CC=CC=C1F QZGPXSCJMVWRIU-WIYYLYMNSA-N 0.000 claims description 2
• VTNAHLMVLHXHOA-IFMALSPDSA-N (3r)-3-[[1-[(2r)-3-(2-fluorophenoxy)-2-hydroxypropyl]piperidin-4-yl]amino]-1-(4-fluorophenyl)pyrrolidin-2-one Chemical compound C([C@H](O)CN1CCC(CC1)N[C@H]1C(N(CC1)C=1C=CC(F)=CC=1)=O)OC1=CC=CC=C1F VTNAHLMVLHXHOA-IFMALSPDSA-N 0.000 claims description 2
• REZNLSSYSJRPNI-OQHSHRKDSA-N 1-(1,3-benzoxazol-2-yl)-3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidine-2,5-dione Chemical compound C1=CC=C2OC(N3C(=O)CC(C3=O)N3CCN(CC3)C[C@@H](O)COC=3C=C4N=C(SC4=CC=3)C)=NC2=C1 REZNLSSYSJRPNI-OQHSHRKDSA-N 0.000 claims description 2
• IRXTUUVJFBQFHE-BDPMCISCSA-N 1-(3-fluorophenyl)-3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=CC(F)=C1 IRXTUUVJFBQFHE-BDPMCISCSA-N 0.000 claims description 2
• UYTDAJFFSZCAQP-LCQOSCCDSA-N 1-(4-chlorophenyl)-3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(Cl)C=C1 UYTDAJFFSZCAQP-LCQOSCCDSA-N 0.000 claims description 2
• GHXAZDGBQBOFLG-BDPMCISCSA-N 1-(4-chlorophenyl)-3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=C(Cl)C=C1 GHXAZDGBQBOFLG-BDPMCISCSA-N 0.000 claims description 2
• MKJCJYPQBDWRNP-BDPMCISCSA-N 1-(4-fluorophenyl)-3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=C(F)C=C1 MKJCJYPQBDWRNP-BDPMCISCSA-N 0.000 claims description 2
• PZMYZAZQZHAXDW-AVKWCDSFSA-N 1-(4-fluorophenyl)-4-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]pyrrolidin-2-one Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(CC1=O)CN1C1=CC=C(F)C=C1 PZMYZAZQZHAXDW-AVKWCDSFSA-N 0.000 claims description 2
• VKCFXXBGKQEMLM-CQSZACIVSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-(2,3,4,5,6-pentafluorophenyl)ethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=C(F)C(F)=C(F)C(F)=C1F VKCFXXBGKQEMLM-CQSZACIVSA-N 0.000 claims description 2
• JHXJEGFXVMLRLU-JOCHJYFZSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-(2,4,6-trimethylphenyl)ethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=C(C)C=C(C)C=C1C JHXJEGFXVMLRLU-JOCHJYFZSA-N 0.000 claims description 2
• ODWICNCODXBYOZ-JOCHJYFZSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-naphthalen-1-ylethanesulfonamide Chemical compound C1=CC=C2C(NS(=O)(=O)CCN3CCN(CC3)C[C@@H](O)COC=3C=C4N=C(SC4=CC=3)C)=CC=CC2=C1 ODWICNCODXBYOZ-JOCHJYFZSA-N 0.000 claims description 2
• UWNDAXVJJYCJRM-JOCHJYFZSA-N 2-[4-[4-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]butoxy]phenoxy]-2-methylpropanoic acid Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=C(OC(C)(C)C(O)=O)C=C1 UWNDAXVJJYCJRM-JOCHJYFZSA-N 0.000 claims description 2
• CLZUEDBYCHCYTI-JOCHJYFZSA-N 2-[4-[4-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]butoxy]phenyl]acetic acid Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=C(CC(O)=O)C=C1 CLZUEDBYCHCYTI-JOCHJYFZSA-N 0.000 claims description 2
• ZBICCANXTBNYGD-PPUHSXQSSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-(4-methylphenyl)pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(C)C=C1 ZBICCANXTBNYGD-PPUHSXQSSA-N 0.000 claims description 2
• QOEUQVNMGLTSDG-LCQOSCCDSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-[3-(trifluoromethyl)phenyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=CC(C(F)(F)F)=C1 QOEUQVNMGLTSDG-LCQOSCCDSA-N 0.000 claims description 2
• LMISYJLVJSUNTQ-PPUHSXQSSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CCN1C1=CC=C(C(F)(F)F)C=C1 LMISYJLVJSUNTQ-PPUHSXQSSA-N 0.000 claims description 2
• QDSIWXLFIZAEMO-LCQOSCCDSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-phenylpyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=CC=C1 QDSIWXLFIZAEMO-LCQOSCCDSA-N 0.000 claims description 2
• PPMDPFHZYQJNOD-BDPMCISCSA-N 3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]-1-[4-(trifluoromethyl)phenyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=C(C(F)(F)F)C=C1 PPMDPFHZYQJNOD-BDPMCISCSA-N 0.000 claims description 2
• GGZOSMGXMVPANL-LJQANCHMSA-N 4-chloro-n-[2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]ethyl]benzenesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNS(=O)(=O)C1=CC=C(Cl)C=C1 GGZOSMGXMVPANL-LJQANCHMSA-N 0.000 claims description 2
• KOJOHFURFSDNLQ-QGZVFWFLSA-N C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNC(=O)C1=C(F)C=CC=C1F Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNC(=O)C1=C(F)C=CC=C1F KOJOHFURFSDNLQ-QGZVFWFLSA-N 0.000 claims description 2
• HRGACORIHNPPDV-XMMPIXPASA-N ethyl 2-[4-[4-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]butoxy]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OCC)=CC=C1OCCCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 HRGACORIHNPPDV-XMMPIXPASA-N 0.000 claims description 2
• YXBKIMAUEKWQHG-XMMPIXPASA-N ethyl 2-[4-[4-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]butoxy]phenyl]acetate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCCCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 YXBKIMAUEKWQHG-XMMPIXPASA-N 0.000 claims description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
• RHUJTFFWHMUORI-HXUWFJFHSA-N n-(3,4-dimethoxyphenyl)-2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]ethanesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1NS(=O)(=O)CCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 RHUJTFFWHMUORI-HXUWFJFHSA-N 0.000 claims description 2
• LOUQJGPVWQTHFF-HXUWFJFHSA-N n-(4-chlorophenyl)-2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]ethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=CC=C(Cl)C=C1 LOUQJGPVWQTHFF-HXUWFJFHSA-N 0.000 claims description 2
• YLRPALOQCRHPPQ-HXUWFJFHSA-N n-[2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]ethyl]-4-(trifluoromethyl)benzamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNC(=O)C1=CC=C(C(F)(F)F)C=C1 YLRPALOQCRHPPQ-HXUWFJFHSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 206010019280 Heart failures Diseases 0.000 claims 2
• ZZYPAHYVBGCVGZ-LJQANCHMSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-(2-phenoxyethyl)piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=CC=C1 ZZYPAHYVBGCVGZ-LJQANCHMSA-N 0.000 claims 1
• CAQVVOUVAFINPX-HXUWFJFHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-(2-methylphenoxy)ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=CC=C1C CAQVVOUVAFINPX-HXUWFJFHSA-N 0.000 claims 1
• NLJDIJWXVUOJFD-RUZDIDTESA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-(4-phenylphenoxy)ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC(C=C1)=CC=C1C1=CC=CC=C1 NLJDIJWXVUOJFD-RUZDIDTESA-N 0.000 claims 1
• XLTXRIHKLHVMHX-GOSISDBHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[2-[4-(trifluoromethoxy)phenoxy]ethyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(OC(F)(F)F)C=C1 XLTXRIHKLHVMHX-GOSISDBHSA-N 0.000 claims 1
• JCCWEXQYGWYMGT-HXUWFJFHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[3-[4-(trifluoromethyl)phenoxy]propyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCOC1=CC=C(C(F)(F)F)C=C1 JCCWEXQYGWYMGT-HXUWFJFHSA-N 0.000 claims 1
• OCYNFJYVYJHILJ-DPUSYNFFSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-[(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)oxy]butyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1C(C2(C)C)(C)CCC2C1 OCYNFJYVYJHILJ-DPUSYNFFSA-N 0.000 claims 1
• DRMDFXSPDNHEBO-GOSISDBHSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]oxybutyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC=1C=C(C(F)(F)F)N(C)N=1 DRMDFXSPDNHEBO-GOSISDBHSA-N 0.000 claims 1
• ATLPWOXYMCXYFK-OAQYLSRUSA-N (2r)-1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-[4-[4-[4-(trifluoromethyl)phenoxy]butyl]piperazin-1-yl]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=C(C(F)(F)F)C=C1 ATLPWOXYMCXYFK-OAQYLSRUSA-N 0.000 claims 1
• QHOSMFPDYSEGQO-LJQANCHMSA-N (2r)-1-[4-[2-(3,5-dichlorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC(Cl)=CC(Cl)=C1 QHOSMFPDYSEGQO-LJQANCHMSA-N 0.000 claims 1
• QEHXJVZSNFOQKZ-QGZVFWFLSA-N (2r)-1-[4-[2-(3-chloro-4-fluorophenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC=C(F)C(Cl)=C1 QEHXJVZSNFOQKZ-QGZVFWFLSA-N 0.000 claims 1
• GCOVAPIXCFOKLY-LJQANCHMSA-N (2r)-1-[4-[2-(4-chloro-2-methoxyphenoxy)ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound COC1=CC(Cl)=CC=C1OCCN1CCN(C[C@@H](O)COC=2C=C3N=C(C)SC3=CC=2)CC1 GCOVAPIXCFOKLY-LJQANCHMSA-N 0.000 claims 1
• VKWFULSNZYOQFY-LJQANCHMSA-N (2r)-1-[4-[2-[3,5-bis(trifluoromethyl)phenoxy]ethyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCOC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 VKWFULSNZYOQFY-LJQANCHMSA-N 0.000 claims 1
• POQATYDECVVVMK-OADZCNSWSA-N (2r)-1-[4-[4-(4-tert-butylcyclohexyl)oxybutyl]piperazin-1-yl]-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propan-2-ol Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1CCC(C(C)(C)C)CC1 POQATYDECVVVMK-OADZCNSWSA-N 0.000 claims 1
• PXYXGDHQGRXQKT-GWQXNCQPSA-N (3r)-1-(4-chlorophenyl)-3-[4-[2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidin-2-one Chemical compound C([C@H](C1=O)N2CCN(CC2)CC(O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=C(Cl)C=C1 PXYXGDHQGRXQKT-GWQXNCQPSA-N 0.000 claims 1
• SLUYYMDJMFISFC-FYYLOGMGSA-N (3r)-1-(4-chlorophenyl)-3-[[1-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperidin-4-yl]amino]pyrrolidin-2-one Chemical compound C([C@H](C1=O)NC2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=C(Cl)C=C1 SLUYYMDJMFISFC-FYYLOGMGSA-N 0.000 claims 1
• LHOJERYLNWQTFM-FYYLOGMGSA-N (3r)-3-[[1-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperidin-4-yl]amino]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C([C@H](C1=O)NC2CCN(CC2)C[C@@H](O)COC=2C=C3N=C(SC3=CC=2)C)CN1C1=CC=C(C(F)(F)F)C=C1 LHOJERYLNWQTFM-FYYLOGMGSA-N 0.000 claims 1
• METPQIIZYFLBFH-IFMALSPDSA-N (3r)-3-[[1-[(2r)-3-(2-fluorophenoxy)-2-hydroxypropyl]piperidin-4-yl]amino]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C([C@H](O)CN1CCC(CC1)N[C@H]1C(N(CC1)C=1C=CC(=CC=1)C(F)(F)F)=O)OC1=CC=CC=C1F METPQIIZYFLBFH-IFMALSPDSA-N 0.000 claims 1
• PURFTEAEBRTKHP-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidine-2,5-dione Chemical compound C=1C=C2SC(C)=NC2=CC=1OCC(O)CN(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=CC(F)=C1 PURFTEAEBRTKHP-UHFFFAOYSA-N 0.000 claims 1
• NEZJSLPQIBAXFV-LWMIZPGFSA-N 1-(3-tert-butyl-4-chlorophenyl)-3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=C(Cl)C(C(C)(C)C)=C1 NEZJSLPQIBAXFV-LWMIZPGFSA-N 0.000 claims 1
• VRPJXMGTABXXJG-CILPGNKCSA-N 1-(4-ethenylphenyl)-3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(C=C)C=C1 VRPJXMGTABXXJG-CILPGNKCSA-N 0.000 claims 1
• XLILBFINWDQOPW-LCQOSCCDSA-N 1-(4-fluorophenyl)-3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CC(=O)N1C1=CC=C(F)C=C1 XLILBFINWDQOPW-LCQOSCCDSA-N 0.000 claims 1
• NBTPSNXKCBOAPU-MQNHUJCZSA-N 1-(4-tert-butylphenyl)-3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C1=O)CC(=O)N1C1=CC=C(C(C)(C)C)C=C1 NBTPSNXKCBOAPU-MQNHUJCZSA-N 0.000 claims 1
• JIVFKCMTEJHBOA-JOCHJYFZSA-N 1-[3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]naphthalen-1-yl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C=C1C=CC=CC1=1)=CC=1N1C(=O)CCC1=O JIVFKCMTEJHBOA-JOCHJYFZSA-N 0.000 claims 1
• MGLISTZAOQASOP-HSZRJFAPSA-N 1-[3-[[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]naphthalen-1-yl]pyrrolidine-2,5-dione Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CC(C=C1C=CC=CC1=1)=CC=1N1C(=O)CCC1=O MGLISTZAOQASOP-HSZRJFAPSA-N 0.000 claims 1
• HWINPJJDNBHWIY-CQSZACIVSA-N 2,3,4,5,6-pentafluoro-n-[2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]ethyl]benzenesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCNS(=O)(=O)C1=C(F)C(F)=C(F)C(F)=C1F HWINPJJDNBHWIY-CQSZACIVSA-N 0.000 claims 1
• DTNIWBZGAJTZNE-GOSISDBHSA-N 2-[2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCN(CC1)CCN1C[C@@H](O)COC1=CC=C(SC(C)=N2)C2=C1 DTNIWBZGAJTZNE-GOSISDBHSA-N 0.000 claims 1
• ZHDACXHAFFWYER-OAQYLSRUSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-(4-methylphenyl)ethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=CC=C(C)C=C1 ZHDACXHAFFWYER-OAQYLSRUSA-N 0.000 claims 1
• HWQKZPPCKDSFJT-HXUWFJFHSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-[3-(trifluoromethyl)phenyl]ethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 HWQKZPPCKDSFJT-HXUWFJFHSA-N 0.000 claims 1
• WWTREPGVZGGIGC-LJQANCHMSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-[4-(trifluoromethoxy)phenyl]ethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=CC=C(OC(F)(F)F)C=C1 WWTREPGVZGGIGC-LJQANCHMSA-N 0.000 claims 1
• SKLKYLPDORXECX-HXUWFJFHSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]ethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=CC=C(C(F)(F)F)C=C1 SKLKYLPDORXECX-HXUWFJFHSA-N 0.000 claims 1
• FAUNYVUNVRPXED-HXUWFJFHSA-N 2-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-phenylethanesulfonamide Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCS(=O)(=O)NC1=CC=CC=C1 FAUNYVUNVRPXED-HXUWFJFHSA-N 0.000 claims 1
• MNOPGXCCOJZZTM-CILPGNKCSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-(4-methylphenyl)pyrrolidin-2-one Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CCN1C1=CC=C(C)C=C1 MNOPGXCCOJZZTM-CILPGNKCSA-N 0.000 claims 1
• SGJVLWRRFDYSSZ-PPUHSXQSSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CCN1C1=CC=CC(C(F)(F)F)=C1 SGJVLWRRFDYSSZ-PPUHSXQSSA-N 0.000 claims 1
• IMTJKANBVGGKEV-PPUHSXQSSA-N 3-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-1-phenylpyrrolidin-2-one Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1C(C1=O)CCN1C1=CC=CC=C1 IMTJKANBVGGKEV-PPUHSXQSSA-N 0.000 claims 1
• GODLEYIEJQEZGS-HSZRJFAPSA-N 3-[4-[4-[4-[(2r)-2-hydroxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]butoxy]phenyl]propanoic acid Chemical compound C([C@@H](O)COC=1C=C2N=C(SC2=CC=1)C)N(CC1)CCN1CCCCOC1=CC=C(CCC(O)=O)C=C1 GODLEYIEJQEZGS-HSZRJFAPSA-N 0.000 claims 1
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