CA2579621A1

CA2579621A1 - Substituted piperazine compounds and their use as fatty acid oxidation inhibitors

Substituted piperazine compounds and their use as fatty acid oxidation inhibitors Download PDF

Info

Publication number: CA2579621A1
Authority: CA; Canada
Prior art keywords: compound; formula; hydrogen; methylbenzothiazol; alkyl
Prior art date: 2004-09-08
Legal status : Abandoned

Application number

CA002579621A

Other languages

English (en)

French (fr)

Inventor

Jeff Zablocki

Dmitry Koltun

Current Assignee

Gilead Palo Alto Inc

Original Assignee

Individual

Priority date

2004-09-08

Filing date

2005-09-07

Publication date

2006-03-16

2005-09-07 Application filed by Individual filed Critical Individual

2006-03-16 Publication of CA2579621A1 publication Critical patent/CA2579621A1/en

Status Abandoned legal-status Critical Current

Links

150000004885 piperazines Chemical class 0.000 title abstract description 7
230000003647 oxidation Effects 0.000 title description 29
238000007254 oxidation reaction Methods 0.000 title description 29
235000014113 dietary fatty acids Nutrition 0.000 title description 15
239000000194 fatty acid Substances 0.000 title description 15
229930195729 fatty acid Natural products 0.000 title description 15
150000004665 fatty acids Chemical class 0.000 title description 15
239000003112 inhibitor Substances 0.000 title description 9
201000010099 disease Diseases 0.000 claims abstract description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
206010002383 Angina Pectoris Diseases 0.000 claims abstract description 10
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
206010022562 Intermittent claudication Diseases 0.000 claims abstract description 7
208000010125 myocardial infarction Diseases 0.000 claims abstract description 6
206010003130 Arrhythmia supraventricular Diseases 0.000 claims abstract description 5
206010007559 Cardiac failure congestive 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
208000021156 intermittent vascular claudication 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
150000001875 compounds Chemical class 0.000 claims description 182
-1 2-methylbenzo-1,3-thiazol-5-yl Chemical group 0.000 claims description 97
125000000217 alkyl group Chemical group 0.000 claims description 67
125000001072 heteroaryl group Chemical group 0.000 claims description 51
239000001257 hydrogen Substances 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 37
238000000034 method Methods 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
125000003107 substituted aryl group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
WPLCPMCSAKSBTL-UHFFFAOYSA-N 2-[4-[2-acetamido-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-(3-phenylphenyl)acetamide Chemical compound C=1C=C2SC(C)=NC2=CC=1OCC(NC(=O)C)CN(CC1)CCN1CC(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 WPLCPMCSAKSBTL-UHFFFAOYSA-N 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
KILSHWDEQAIYCB-UHFFFAOYSA-N n-(9h-fluoren-2-yl)-4-[2-(methanesulfonamido)-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazine-1-carboxamide Chemical compound C1=C2CC3=CC=CC=C3C2=CC=C1NC(=O)N(CC1)CCN1CC(NS(C)(=O)=O)COC1=CC=C(SC(C)=N2)C2=C1 KILSHWDEQAIYCB-UHFFFAOYSA-N 0.000 claims description 4
239000000651 prodrug Substances 0.000 claims description 4
229940002612 prodrug Drugs 0.000 claims description 4
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
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
MEMHSSUPSMDUNI-OAQYLSRUSA-N 3-[[4-[(2r)-2-methoxy-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]methyl]-5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound C([C@H](COC=1C=C2N=C(C)SC2=CC=1)OC)N(CC1)CCN1CC(N=1)=NOC=1C1=CC=C(C(F)(F)F)C=C1 MEMHSSUPSMDUNI-OAQYLSRUSA-N 0.000 claims description 2
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 7
230000001746 atrial effect Effects 0.000 abstract description 6
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 76
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
125000001424 substituent group Chemical group 0.000 description 46
125000003118 aryl group Chemical group 0.000 description 43
238000002360 preparation method Methods 0.000 description 43
238000006243 chemical reaction Methods 0.000 description 36
239000000243 solution Substances 0.000 description 35
239000002904 solvent Substances 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 28
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 28
239000004480 active ingredient Substances 0.000 description 27
125000003545 alkoxy group Chemical group 0.000 description 27
239000008103 glucose Substances 0.000 description 26
229910052736 halogen Inorganic materials 0.000 description 25
150000002367 halogens Chemical class 0.000 description 25
230000002829 reductive effect Effects 0.000 description 25
125000004093 cyano group Chemical group *C#N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 21
125000000753 cycloalkyl group Chemical group 0.000 description 21
125000000623 heterocyclic group Chemical group 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
150000001412 amines Chemical class 0.000 description 20
125000004181 carboxyalkyl group Chemical group 0.000 description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
125000003342 alkenyl group Chemical group 0.000 description 19
239000003826 tablet Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
125000000392 cycloalkenyl group Chemical group 0.000 description 17
125000000304 alkynyl group Chemical group 0.000 description 16
239000000047 product Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 15
239000004615 ingredient Substances 0.000 description 15
230000010412 perfusion Effects 0.000 description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 15
239000012442 inert solvent Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 12
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
239000000843 powder Substances 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
125000002947 alkylene group Chemical group 0.000 description 11
239000002585 base Substances 0.000 description 11
230000000747 cardiac effect Effects 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
125000000547 substituted alkyl group Chemical group 0.000 description 11
239000002253 acid Substances 0.000 description 10
125000004414 alkyl thio group Chemical group 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
230000034659 glycolysis Effects 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
229930194542 Keto Natural products 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 9
125000004442 acylamino group Chemical group 0.000 description 9
125000004423 acyloxy group Chemical group 0.000 description 9
125000005110 aryl thio group Chemical group 0.000 description 9
125000004104 aryloxy group Chemical group 0.000 description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000005553 heteroaryloxy group Chemical group 0.000 description 9
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 9
125000000468 ketone group Chemical group 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
229910052760 oxygen Inorganic materials 0.000 description 9
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 9
150000003573 thiols Chemical class 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
125000000033 alkoxyamino group Chemical group 0.000 description 8
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 8
125000006598 aminocarbonylamino group Chemical group 0.000 description 8
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
125000004429 atom Chemical group 0.000 description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 8
125000005368 heteroarylthio group Chemical group 0.000 description 8
125000004470 heterocyclooxy group Chemical group 0.000 description 8
125000004468 heterocyclylthio group Chemical group 0.000 description 8
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
239000000725 suspension Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
125000001246 bromo group Chemical group Br* 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
125000002346 iodo group Chemical group I* 0.000 description 6
239000007788 liquid Substances 0.000 description 6
235000019359 magnesium stearate Nutrition 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
230000002107 myocardial effect Effects 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
238000000746 purification Methods 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
210000001519 tissue Anatomy 0.000 description 6
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238000003556 assay Methods 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
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150000002430 hydrocarbons Chemical group 0.000 description 5
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239000008108 microcrystalline cellulose Substances 0.000 description 5
229940016286 microcrystalline cellulose Drugs 0.000 description 5
IGYFXWQSOCQALS-UHFFFAOYSA-N n-[1-[(2-methyl-1,3-benzothiazol-5-yl)oxy]-3-piperazin-1-ylpropan-2-yl]acetamide Chemical compound C=1C=C2SC(C)=NC2=CC=1OCC(NC(=O)C)CN1CCNCC1 IGYFXWQSOCQALS-UHFFFAOYSA-N 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002243 precursor Substances 0.000 description 5
230000036316 preload Effects 0.000 description 5
239000008107 starch Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000005017 substituted alkenyl group Chemical group 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
229940124597 therapeutic agent Drugs 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
238000011067 equilibration Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
238000005259 measurement Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
230000036284 oxygen consumption Effects 0.000 description 4
239000006187 pill Substances 0.000 description 4
230000036470 plasma concentration Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000000523 sample Substances 0.000 description 4
229930195734 saturated hydrocarbon Natural products 0.000 description 4
239000011734 sodium Substances 0.000 description 4
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239000007787 solid Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
208000024891 symptom Diseases 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
PUKBJDJFQPEHMQ-UHFFFAOYSA-N 2-[4-[2-(methanesulfonamido)-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]piperazin-1-yl]-n-(3-phenylphenyl)acetamide Chemical compound C=1C=C2SC(C)=NC2=CC=1OCC(NS(C)(=O)=O)CN(CC1)CCN1CC(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 PUKBJDJFQPEHMQ-UHFFFAOYSA-N 0.000 description 3
YSPRCDGVFRVBED-UHFFFAOYSA-N 2-methyl-5-(oxiran-2-ylmethoxy)-1,3-benzothiazole Chemical compound C=1C=C2SC(C)=NC2=CC=1OCC1CO1 YSPRCDGVFRVBED-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
RZHAVOBIGPWQIZ-UHFFFAOYSA-N 4-[2-acetamido-3-[(2-methyl-1,3-benzothiazol-5-yl)oxy]propyl]-n-(9h-fluoren-2-yl)piperazine-1-carboxamide Chemical compound C1=C2CC3=CC=CC=C3C2=CC=C1NC(=O)N(CC1)CCN1CC(NC(=O)C)COC1=CC=C(SC(C)=N2)C2=C1 RZHAVOBIGPWQIZ-UHFFFAOYSA-N 0.000 description 3
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XKLMZUWKNUAPSZ-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide Chemical compound COC1=CC=CC=C1OCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 XKLMZUWKNUAPSZ-UHFFFAOYSA-N 0.000 description 3
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