ZA200610152B - Aryl-substituted piperazine derivatives - Google Patents
Aryl-substituted piperazine derivatives Download PDFInfo
- Publication number
- ZA200610152B ZA200610152B ZA200610152A ZA200610152A ZA200610152B ZA 200610152 B ZA200610152 B ZA 200610152B ZA 200610152 A ZA200610152 A ZA 200610152A ZA 200610152 A ZA200610152 A ZA 200610152A ZA 200610152 B ZA200610152 B ZA 200610152B
- Authority
- ZA
- South Africa
- Prior art keywords
- ethyl
- trifluoromethyl
- dimethyl
- phenoxy
- benzoyl
- Prior art date
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- 150000004885 piperazines Chemical class 0.000 title description 30
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims description 183
- 229910052736 halogen Inorganic materials 0.000 claims description 158
- 150000002367 halogens Chemical class 0.000 claims description 158
- 125000001424 substituent group Chemical group 0.000 claims description 136
- 229910052739 hydrogen Inorganic materials 0.000 claims description 131
- 239000001257 hydrogen Substances 0.000 claims description 131
- 150000003839 salts Chemical class 0.000 claims description 125
- -1 hydroxy, nitro, cyano, amino, aminocarbonyl Chemical group 0.000 claims description 116
- 150000002431 hydrogen Chemical class 0.000 claims description 110
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 claims description 101
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 86
- 229910052799 carbon Inorganic materials 0.000 claims description 64
- 125000004043 oxo group Chemical group O=* 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
- 230000027455 binding Effects 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 238000003556 assay Methods 0.000 claims description 19
- 210000004027 cell Anatomy 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 239000005977 Ethylene Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
- 150000002923 oximes Chemical class 0.000 claims description 13
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 12
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 241000282414 Homo sapiens Species 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 230000004913 activation Effects 0.000 claims description 10
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 8
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- 201000010099 disease Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 208000012201 sexual and gender identity disease Diseases 0.000 claims description 8
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- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 7
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 7
- 208000030814 Eating disease Diseases 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000000338 in vitro Methods 0.000 claims description 7
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- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 235000014632 disordered eating Nutrition 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 238000001727 in vivo Methods 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 208000019622 heart disease Diseases 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 240000007594 Oryza sativa Species 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 4
- 229910014033 C-OH Inorganic materials 0.000 claims description 3
- 229910014570 C—OH Inorganic materials 0.000 claims description 3
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 3
- 238000002001 electrophysiology Methods 0.000 claims description 3
- 230000007831 electrophysiology Effects 0.000 claims description 3
- 230000004634 feeding behavior Effects 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 238000000670 ligand binding assay Methods 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 claims description 3
- 210000001519 tissue Anatomy 0.000 claims description 3
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- 230000004075 alteration Effects 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000006071 cream Substances 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 49
- 125000002999 4-(trifluoromethyl)benzoyl group Chemical group FC(C1=CC=C(C(=O)*)C=C1)(F)F 0.000 claims 34
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 claims 19
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 17
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 10
- 125000005879 dioxolanyl group Chemical group 0.000 claims 8
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 8
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims 7
- 125000002757 morpholinyl group Chemical group 0.000 claims 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 5
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- ONHPOXROAPYCGT-UHFFFAOYSA-N 2,3,4,6,7,8,9,9a-octahydro-1h-pyrido[1,2-a]pyrazine Chemical compound C1CNCC2CCCCN21 ONHPOXROAPYCGT-UHFFFAOYSA-N 0.000 claims 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 3
- KGWDZPBRJBSJST-UHFFFAOYSA-N [4-[1-[4-[2-(dimethylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCN(C)C)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 KGWDZPBRJBSJST-UHFFFAOYSA-N 0.000 claims 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 3
- WAWGZWCYPBLMLU-RBBKRZOGSA-N 1-[4-[(6r,9as)-2-[6-(trifluoromethyl)pyridine-3-carbonyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-one Chemical compound CC1=C(C)C(OCC(=O)C)=CC=C1[C@@H]1N2CCN(C(=O)C=3C=NC(=CC=3)C(F)(F)F)C[C@@H]2CCC1 WAWGZWCYPBLMLU-RBBKRZOGSA-N 0.000 claims 2
- IEYBVSRQBQOXRH-XUZZJYLKSA-N 2-[4-[(6r,9as)-2-(4-fluoro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-n,n-dimethylacetamide Chemical compound C1=C(F)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(=O)N(C)C)=CC=3)C)CC2)=C1 IEYBVSRQBQOXRH-XUZZJYLKSA-N 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 210000004958 brain cell Anatomy 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 2
- LFJHCQIZLMISED-JYFHCDHNSA-N n-[3-[4-[(6r,9as)-2-(4-fluoro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propyl]acetamide Chemical compound C1=C(F)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCCCNC(C)=O)=CC=3)C)CC2)=C1 LFJHCQIZLMISED-JYFHCDHNSA-N 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- SFISUACWEUAPDJ-SZMVWBNQSA-N (2-chloro-5-methyl-1,3-thiazol-4-yl)-[(1s,4s)-5-[(1s)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCOC)=CC=1)C)[H])N2C(=O)C=1N=C(Cl)SC=1C SFISUACWEUAPDJ-SZMVWBNQSA-N 0.000 claims 1
- WUIIGRHMMRGGIM-AWRGLXIESA-N (2s)-1-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-3-aminopropan-2-ol Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OC[C@@H](O)CN)=CC=3)C)CC2)=C1 WUIIGRHMMRGGIM-AWRGLXIESA-N 0.000 claims 1
- SLLJNAJMBSEWJM-BPARTEKVSA-N (3s)-4-[2,3-dimethyl-4-[1-[4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl]ethyl]phenoxy]-3-hydroxybutanenitrile Chemical compound C=1C=C(OC[C@@H](O)CC#N)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 SLLJNAJMBSEWJM-BPARTEKVSA-N 0.000 claims 1
- MFGMCRWIMAJMAP-SONWIMMPSA-N (3s)-4-[4-[(6r,9as)-2-[4-(trifluoromethyl)benzoyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-3-hydroxybutanenitrile Chemical compound C1=C(OC[C@@H](O)CC#N)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 MFGMCRWIMAJMAP-SONWIMMPSA-N 0.000 claims 1
- ZKSSPONCGXHNRS-STZQEDGTSA-N (4-chlorophenyl)-[(1r,4r)-5-[(1r)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@@]1(N(C[C@@]2([H])C1)[C@H](C)C=1C(=C(C)C(OCCOC)=CC=1)C)[H])N2C(=O)C1=CC=C(Cl)C=C1 ZKSSPONCGXHNRS-STZQEDGTSA-N 0.000 claims 1
- NAGFELGVKQIKIU-UEVCKROQSA-N (4-chlorophenyl)-[(1r,4r)-5-[(1r)-1-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@@]1(N(C[C@@]2([H])C1)[C@H](C)C=1C(=C(C)C(OCCCOC)=CC=1)C)[H])N2C(=O)C1=CC=C(Cl)C=C1 NAGFELGVKQIKIU-UEVCKROQSA-N 0.000 claims 1
- PALGPXIQXBAXRO-JOCHJYFZSA-N (4-chlorophenyl)-[4-[(1r)-1-[2,3-dimethyl-4-[3-(propan-2-ylamino)propoxy]phenyl]ethyl]piperazin-1-yl]methanone Chemical compound CC1=C(C)C(OCCCNC(C)C)=CC=C1[C@@H](C)N1CCN(C(=O)C=2C=CC(Cl)=CC=2)CC1 PALGPXIQXBAXRO-JOCHJYFZSA-N 0.000 claims 1
- YMVKGNHPFVHTTM-LJQANCHMSA-N (4-chlorophenyl)-[4-[(1r)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound CC1=C(C)C(OCCOC)=CC=C1[C@@H](C)N1CCN(C(=O)C=2C=CC(Cl)=CC=2)CC1 YMVKGNHPFVHTTM-LJQANCHMSA-N 0.000 claims 1
- RSQLGKGHLVKSHV-LJQANCHMSA-N (4-chlorophenyl)-[4-[(1r)-1-[4-(3-chloropropoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCCCl)=CC=2)C)CCN1C(=O)C1=CC=C(Cl)C=C1 RSQLGKGHLVKSHV-LJQANCHMSA-N 0.000 claims 1
- PXQXCCIVSPSQGT-HXUWFJFHSA-N (4-chlorophenyl)-[4-[(1r)-1-[4-(3-hydroxy-3-methylbutoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCC(C)(C)O)=CC=2)C)CCN1C(=O)C1=CC=C(Cl)C=C1 PXQXCCIVSPSQGT-HXUWFJFHSA-N 0.000 claims 1
- DTNKUDQDQBERPL-UHFFFAOYSA-N (4-chlorophenyl)-[4-[1-[2,3-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]ethyl]piperazin-1-yl]methanone Chemical compound C=1C=C(OCCCS(C)(=O)=O)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 DTNKUDQDQBERPL-UHFFFAOYSA-N 0.000 claims 1
- KNTFYPBDGGARNI-UHFFFAOYSA-N (4-chlorophenyl)-[4-[1-[2,3-dimethyl-4-[3-(methylamino)propoxy]phenyl]ethyl]piperazin-1-yl]methanone Chemical compound CC1=C(C)C(OCCCNC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(Cl)=CC=2)CC1 KNTFYPBDGGARNI-UHFFFAOYSA-N 0.000 claims 1
- SKTCMLVTCAGHEM-UHFFFAOYSA-N (4-chlorophenyl)-[4-[1-[4-(2-hydroxy-2-methylpropoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound C=1C=C(OCC(C)(C)O)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 SKTCMLVTCAGHEM-UHFFFAOYSA-N 0.000 claims 1
- UTDNCXOUWKXBCR-UHFFFAOYSA-N (4-chlorophenyl)-[4-[1-[4-(2-hydroxyethoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound C=1C=C(OCCO)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 UTDNCXOUWKXBCR-UHFFFAOYSA-N 0.000 claims 1
- YMVKGNHPFVHTTM-UHFFFAOYSA-N (4-chlorophenyl)-[4-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(Cl)=CC=2)CC1 YMVKGNHPFVHTTM-UHFFFAOYSA-N 0.000 claims 1
- RSQLGKGHLVKSHV-UHFFFAOYSA-N (4-chlorophenyl)-[4-[1-[4-(3-chloropropoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound C=1C=C(OCCCCl)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 RSQLGKGHLVKSHV-UHFFFAOYSA-N 0.000 claims 1
- UPUGDKWJPOYAEJ-UHFFFAOYSA-N (4-chlorophenyl)-[4-[1-[4-(3-hydroxypropoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]methanone Chemical compound C=1C=C(OCCCO)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 UPUGDKWJPOYAEJ-UHFFFAOYSA-N 0.000 claims 1
- LLXGMOGIZFXJGT-IHPCNDPISA-N (6-chloropyridin-3-yl)-[(1s,4s)-5-[(1s)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCOC)=CC=1)C)[H])N2C(=O)C1=CC=C(Cl)N=C1 LLXGMOGIZFXJGT-IHPCNDPISA-N 0.000 claims 1
- KIXVZBYDOYLZRT-VJBMBRPKSA-N (6-ethylpyridin-3-yl)-[(1s,4s)-5-[(1s)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCOC)=CC=1)C)[H])N2C(=O)C1=CC=C(CC)N=C1 KIXVZBYDOYLZRT-VJBMBRPKSA-N 0.000 claims 1
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- VMSLFFVOGGOALW-WIOPSUGQSA-N (6r,9as)-2-(4-chloro-3-methoxyphenyl)-6-[2,3-dimethyl-4-(2-methylpropoxy)phenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazine Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(C)C)=CC=3)C)CC2)=C1 VMSLFFVOGGOALW-WIOPSUGQSA-N 0.000 claims 1
- YVIYRNQJDFDJMF-JYFHCDHNSA-N (6r,9as)-2-(4-chloro-3-methoxyphenyl)-6-[2,3-dimethyl-4-(2-propan-2-yloxyethoxy)phenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazine Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCCOC(C)C)=CC=3)C)CC2)=C1 YVIYRNQJDFDJMF-JYFHCDHNSA-N 0.000 claims 1
- BEXHJNOQCBQLQQ-WIOPSUGQSA-N (6r,9as)-2-(4-chloro-3-methoxyphenyl)-6-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazine Chemical compound CC1=C(C)C(OCCCOC)=CC=C1[C@@H]1N2CCN(C=3C=C(OC)C(Cl)=CC=3)C[C@@H]2CCC1 BEXHJNOQCBQLQQ-WIOPSUGQSA-N 0.000 claims 1
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- UNHJJGUSZLJBHU-JYFHCDHNSA-N (6r,9as)-2-(4-chloro-3-methoxyphenyl)-6-[4-[2-(2-methoxyethoxy)ethoxy]-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazine Chemical compound CC1=C(C)C(OCCOCCOC)=CC=C1[C@@H]1N2CCN(C=3C=C(OC)C(Cl)=CC=3)C[C@@H]2CCC1 UNHJJGUSZLJBHU-JYFHCDHNSA-N 0.000 claims 1
- WNBHYWNKDSMJGU-XUZZJYLKSA-N (6r,9as)-2-(4-fluoro-3-methoxyphenyl)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1[C@@H]1N2CCN(C=3C=C(OC)C(F)=CC=3)C[C@@H]2CCC1 WNBHYWNKDSMJGU-XUZZJYLKSA-N 0.000 claims 1
- YWVPRXLQXMATBJ-UWGRGZNNSA-N (e)-1-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-n-methoxypropan-2-imine Chemical compound CC1=C(C)C(OCC(/C)=N/OC)=CC=C1[C@@H]1N2CCN(C=3C=C(OC)C(Cl)=CC=3)C[C@@H]2CCC1 YWVPRXLQXMATBJ-UWGRGZNNSA-N 0.000 claims 1
- FXNOFCFCPLCUFK-YTEOQAAOSA-N (ne)-n-[1-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-ylidene]hydroxylamine Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OC\C(C)=N\O)=CC=3)C)CC2)=C1 FXNOFCFCPLCUFK-YTEOQAAOSA-N 0.000 claims 1
- IOOSNLZNFHHOSV-YTEOQAAOSA-N (ne)-n-[1-[4-[(6r,9as)-2-(4-fluoro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-ylidene]hydroxylamine Chemical compound C1=C(F)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OC\C(C)=N\O)=CC=3)C)CC2)=C1 IOOSNLZNFHHOSV-YTEOQAAOSA-N 0.000 claims 1
- YRFFXEBQXHIIPS-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-6-yl)-4-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C3OCCC3=CC=2)CC1 YRFFXEBQXHIIPS-UHFFFAOYSA-N 0.000 claims 1
- OURDXTUHLHFOFC-UHFFFAOYSA-N 1-(3,4-difluoro-5-methoxyphenyl)-4-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(F)=C(F)C=2)CC1 OURDXTUHLHFOFC-UHFFFAOYSA-N 0.000 claims 1
- TXMCHYSGLFINRM-UHFFFAOYSA-N 1-(4-bromo-3-methoxyphenyl)-4-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(Br)=CC=2)CC1 TXMCHYSGLFINRM-UHFFFAOYSA-N 0.000 claims 1
- GJJZEKOOJLWUNE-LJQANCHMSA-N 1-(4-chloro-3-methoxyphenyl)-4-[(1r)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1[C@@H](C)N1CCN(C=2C=C(OC)C(Cl)=CC=2)CC1 GJJZEKOOJLWUNE-LJQANCHMSA-N 0.000 claims 1
- GJJZEKOOJLWUNE-IBGZPJMESA-N 1-(4-chloro-3-methoxyphenyl)-4-[(1s)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1[C@H](C)N1CCN(C=2C=C(OC)C(Cl)=CC=2)CC1 GJJZEKOOJLWUNE-IBGZPJMESA-N 0.000 claims 1
- CQKIZZLRRNAATR-UHFFFAOYSA-N 1-(4-chloro-3-methoxyphenyl)-4-[1-[3-methoxy-4-(2-methoxyethoxy)phenyl]ethyl]piperazine Chemical compound C1=C(OC)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(Cl)=CC=2)CC1 CQKIZZLRRNAATR-UHFFFAOYSA-N 0.000 claims 1
- GJJZEKOOJLWUNE-UHFFFAOYSA-N 1-(4-chloro-3-methoxyphenyl)-4-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(Cl)=CC=2)CC1 GJJZEKOOJLWUNE-UHFFFAOYSA-N 0.000 claims 1
- IICSIEQDUXWKLF-UHFFFAOYSA-N 1-(4-chloro-3-methoxyphenyl)-4-[1-[4-(3-ethoxypropoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCCOCC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(Cl)=CC=2)CC1 IICSIEQDUXWKLF-UHFFFAOYSA-N 0.000 claims 1
- WVMYBERVRQRSBC-UHFFFAOYSA-N 1-(4-chloro-3-methoxyphenyl)-4-[1-[4-(cyclopropylmethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound C1=C(Cl)C(OC)=CC(N2CCN(CC2)C(C)C=2C(=C(C)C(OCC3CC3)=CC=2)C)=C1 WVMYBERVRQRSBC-UHFFFAOYSA-N 0.000 claims 1
- YKTIQVSCKDTLRI-UHFFFAOYSA-N 1-(4-chloro-3-methoxyphenyl)-4-[1-[4-(cyclopropylmethoxy)-3-methoxyphenyl]ethyl]piperazine Chemical compound C1=C(Cl)C(OC)=CC(N2CCN(CC2)C(C)C=2C=C(OC)C(OCC3CC3)=CC=2)=C1 YKTIQVSCKDTLRI-UHFFFAOYSA-N 0.000 claims 1
- RPGHTZXKDQPHIR-UHFFFAOYSA-N 1-(4-ethenyl-3-methoxyphenyl)-4-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(C=C)=CC=2)CC1 RPGHTZXKDQPHIR-UHFFFAOYSA-N 0.000 claims 1
- JKPIILKKRYQROR-UHFFFAOYSA-N 1-[1-(4-butoxy-2,3-dimethylphenyl)ethyl]-4-(4-chloro-3-methoxyphenyl)piperazine Chemical compound CC1=C(C)C(OCCCC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(Cl)=CC=2)CC1 JKPIILKKRYQROR-UHFFFAOYSA-N 0.000 claims 1
- XTXVNIVBPIEGGU-UHFFFAOYSA-N 1-[1-(4-butoxy-3-methoxyphenyl)ethyl]-4-(4-chloro-3-methoxyphenyl)piperazine Chemical compound C1=C(OC)C(OCCCC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(Cl)=CC=2)CC1 XTXVNIVBPIEGGU-UHFFFAOYSA-N 0.000 claims 1
- PNECAPGQJHDZFK-UHFFFAOYSA-N 1-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-4-(3-methoxy-4-methylphenyl)piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C(OC)C(C)=CC=2)CC1 PNECAPGQJHDZFK-UHFFFAOYSA-N 0.000 claims 1
- BVDCJOXLOPOFRH-UHFFFAOYSA-N 1-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-4-(3-methoxyphenyl)piperazine Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C=2C=C(OC)C=CC=2)CC1 BVDCJOXLOPOFRH-UHFFFAOYSA-N 0.000 claims 1
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- ZOCGQVXKVFZBBZ-XUZZJYLKSA-N 1-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-one Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(C)=O)=CC=3)C)CC2)=C1 ZOCGQVXKVFZBBZ-XUZZJYLKSA-N 0.000 claims 1
- AERISRAVNAVFAY-BHJNUDTASA-N 1-[4-[(6r,9as)-2-(4-fluoro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-ol Chemical compound C1=C(F)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(C)O)=CC=3)C)CC2)=C1 AERISRAVNAVFAY-BHJNUDTASA-N 0.000 claims 1
- QRRFXDPPJMYLPP-XUZZJYLKSA-N 1-[4-[(6r,9as)-2-(4-fluoro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-one Chemical compound C1=C(F)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(C)=O)=CC=3)C)CC2)=C1 QRRFXDPPJMYLPP-XUZZJYLKSA-N 0.000 claims 1
- GTEOIERCDMKHAL-IHPCNDPISA-N 2,1,3-benzoxadiazol-5-yl-[(1s,4s)-5-[(1s)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C1([C@H](C)N2C[C@]3(N(C(=O)C4=CC5=NON=C5C=C4)C[C@@]2(C3)[H])[H])=CC=C(OCCOC)C(C)=C1C GTEOIERCDMKHAL-IHPCNDPISA-N 0.000 claims 1
- GDIXJRIYFDKAGI-DUXKGJEZSA-N 2-[2,3-dimethyl-4-[(1r)-1-[(1r,4r)-2-[4-(trifluoromethyl)benzoyl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]ethyl]phenoxy]-n-methylacetamide Chemical compound C([C@@]1(N(C[C@@]2([H])C1)[C@H](C)C=1C(=C(C)C(OCC(=O)NC)=CC=1)C)[H])N2C(=O)C1=CC=C(C(F)(F)F)C=C1 GDIXJRIYFDKAGI-DUXKGJEZSA-N 0.000 claims 1
- YEPNJKQGZHRARU-LJQANCHMSA-N 2-[2,3-dimethyl-4-[(1r)-1-[4-[4-(trifluoromethyl)benzoyl]piperazin-1-yl]ethyl]phenoxy]-n-ethylacetamide Chemical compound CC1=C(C)C(OCC(=O)NCC)=CC=C1[C@@H](C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 YEPNJKQGZHRARU-LJQANCHMSA-N 0.000 claims 1
- DDERJJVQCHIGTA-WDSOQIARSA-N 2-[2,3-dimethyl-4-[(1s)-1-[(1s,4s)-2-[6-(trifluoromethyl)pyridine-3-carbonyl]-2,5-diazabicyclo[2.2.1]heptan-5-yl]ethyl]phenoxy]acetonitrile Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCC#N)=CC=1)C)[H])N2C(=O)C1=CC=C(C(F)(F)F)N=C1 DDERJJVQCHIGTA-WDSOQIARSA-N 0.000 claims 1
- YOFHCOFGHIAHBA-UHFFFAOYSA-N 2-[2,3-dimethyl-4-[2-[4-(trifluoromethyl)benzoyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]phenoxy]acetonitrile Chemical compound C1=C(OCC#N)C(C)=C(C)C(C2N3CCN(CC3CCC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 YOFHCOFGHIAHBA-UHFFFAOYSA-N 0.000 claims 1
- JNRCFOUJDOOJEF-UHFFFAOYSA-N 2-[2-chloro-5-[4-[1-(3,4-dimethoxyphenyl)ethyl]piperazin-1-yl]phenoxy]-n,n-dimethylethanamine Chemical compound C1=C(OC)C(OC)=CC=C1C(C)N1CCN(C=2C=C(OCCN(C)C)C(Cl)=CC=2)CC1 JNRCFOUJDOOJEF-UHFFFAOYSA-N 0.000 claims 1
- IGCBCZZMXJGYTR-XUZZJYLKSA-N 2-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-n,n-dimethylacetamide Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(=O)N(C)C)=CC=3)C)CC2)=C1 IGCBCZZMXJGYTR-XUZZJYLKSA-N 0.000 claims 1
- JHGCUTLFMRMACR-WIOPSUGQSA-N 2-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-n-(2-methoxyethyl)acetamide Chemical compound CC1=C(C)C(OCC(=O)NCCOC)=CC=C1[C@@H]1N2CCN(C=3C=C(OC)C(Cl)=CC=3)C[C@@H]2CCC1 JHGCUTLFMRMACR-WIOPSUGQSA-N 0.000 claims 1
- ZXRWKJKUNUXTTJ-JYFHCDHNSA-N 2-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-n-[2-(dimethylamino)ethyl]acetamide Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(=O)NCCN(C)C)=CC=3)C)CC2)=C1 ZXRWKJKUNUXTTJ-JYFHCDHNSA-N 0.000 claims 1
- JOPSRZVEHAIBDD-RPLLCQBOSA-N 2-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-n-butyl-n-methylacetamide Chemical compound CC1=C(C)C(OCC(=O)N(C)CCCC)=CC=C1[C@@H]1N2CCN(C=3C=C(OC)C(Cl)=CC=3)C[C@@H]2CCC1 JOPSRZVEHAIBDD-RPLLCQBOSA-N 0.000 claims 1
- CMDHCKMSOWJFLE-XUZZJYLKSA-N 2-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]-n-ethylacetamide Chemical compound CC1=C(C)C(OCC(=O)NCC)=CC=C1[C@@H]1N2CCN(C=3C=C(OC)C(Cl)=CC=3)C[C@@H]2CCC1 CMDHCKMSOWJFLE-XUZZJYLKSA-N 0.000 claims 1
- OEJSADAJQLVHKS-SIKLNZKXSA-N 2-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]ethanimidamide Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCC(N)=N)=CC=3)C)CC2)=C1 OEJSADAJQLVHKS-SIKLNZKXSA-N 0.000 claims 1
- BYGAKWCQDIKLLU-NZQKXSOJSA-N 2-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]ethanol Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OCCO)=CC=3)C)CC2)=C1 BYGAKWCQDIKLLU-NZQKXSOJSA-N 0.000 claims 1
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- YWEIHMYESBMZQL-IHPCNDPISA-N [(1s,4s)-5-[(1s)-1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]-[5-(trifluoromethyl)pyridin-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCOC)=CC=1)C)[H])N2C(=O)C1=CC=C(C(F)(F)F)C=N1 YWEIHMYESBMZQL-IHPCNDPISA-N 0.000 claims 1
- URHXYVQHJVLZIA-NYVOZVTQSA-N [(1s,4s)-5-[(1s)-1-[4-(3-aminopropoxy)-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCCN)=CC=1)C)[H])N2C(=O)C1=CC=C(C(F)(F)F)C=C1 URHXYVQHJVLZIA-NYVOZVTQSA-N 0.000 claims 1
- XVYOANZCCPBOGX-VJBMBRPKSA-N [(1s,4s)-5-[(1s)-1-[4-[2-(dimethylamino)ethoxy]-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCN(C)C)=CC=1)C)[H])N2C(=O)C1=CC=C(C(F)(F)F)C=C1 XVYOANZCCPBOGX-VJBMBRPKSA-N 0.000 claims 1
- KDEYKORXDBCMIF-OYDLWJJNSA-N [(1s,4s)-5-[(1s)-1-[4-[3-(dimethylamino)propoxy]-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCCN(C)C)=CC=1)C)[H])N2C(=O)C1=CC=C(C(F)(F)F)C=C1 KDEYKORXDBCMIF-OYDLWJJNSA-N 0.000 claims 1
- NBAZTVBCUKGCEE-TUSQITKMSA-N [(1s,4s)-5-[(1s)-1-[4-[4-(dimethylamino)butoxy]-2,3-dimethylphenyl]ethyl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)[C@@H](C)C=1C(=C(C)C(OCCCCN(C)C)=CC=1)C)[H])N2C(=O)C1=CC=C(C(F)(F)F)C=C1 NBAZTVBCUKGCEE-TUSQITKMSA-N 0.000 claims 1
- YGFRDTNRBMQIOQ-BXTSTYNKSA-N [(2r)-1-acetamido-3-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-yl] acetate Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OC[C@@H](CNC(C)=O)OC(C)=O)=CC=3)C)CC2)=C1 YGFRDTNRBMQIOQ-BXTSTYNKSA-N 0.000 claims 1
- YGFRDTNRBMQIOQ-PNIUZAESSA-N [(2s)-1-acetamido-3-[4-[(6r,9as)-2-(4-chloro-3-methoxyphenyl)-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-6-yl]-2,3-dimethylphenoxy]propan-2-yl] acetate Chemical compound C1=C(Cl)C(OC)=CC(N2C[C@H]3N([C@H](CCC3)C=3C(=C(C)C(OC[C@H](CNC(C)=O)OC(C)=O)=CC=3)C)CC2)=C1 YGFRDTNRBMQIOQ-PNIUZAESSA-N 0.000 claims 1
- VPWDHRGDEDKLPT-SIKLNZKXSA-N [(6r,9as)-6-[4-(1,3-dihydroxypropan-2-yloxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-(6-chloropyridin-3-yl)methanone Chemical compound C1=C(OC(CO)CO)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=NC(Cl)=CC=2)=C1 VPWDHRGDEDKLPT-SIKLNZKXSA-N 0.000 claims 1
- WLIMQYHHPPFOBJ-JTHBVZDNSA-N [(6r,9as)-6-[4-(2-ethoxyethoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound CC1=C(C)C(OCCOCC)=CC=C1[C@@H]1N2CCN(C(=O)C=3C=NC(=CC=3)C(F)(F)F)C[C@@H]2CCC1 WLIMQYHHPPFOBJ-JTHBVZDNSA-N 0.000 claims 1
- BJKIABRLWLAQTA-RBBKRZOGSA-N [(6r,9as)-6-[4-(2-hydroxy-2-methylpropoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-(6-chloropyridin-3-yl)methanone Chemical compound C1=C(OCC(C)(C)O)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=NC(Cl)=CC=2)=C1 BJKIABRLWLAQTA-RBBKRZOGSA-N 0.000 claims 1
- FSRMQKDIWREWON-LADGPHEKSA-N [(6r,9as)-6-[4-(2-hydroxy-2-methylpropoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=C(OCC(C)(C)O)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 FSRMQKDIWREWON-LADGPHEKSA-N 0.000 claims 1
- SIPHMRJBPQJAEM-RBBKRZOGSA-N [(6r,9as)-6-[4-(2-hydroxy-2-methylpropoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound C1=C(OCC(C)(C)O)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=NC(=CC=2)C(F)(F)F)=C1 SIPHMRJBPQJAEM-RBBKRZOGSA-N 0.000 claims 1
- LLXOFZRGQVSNAP-PZJWPPBQSA-N [(6r,9as)-6-[4-(2-hydroxyethoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound C1=C(OCCO)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=NC(=CC=2)C(F)(F)F)=C1 LLXOFZRGQVSNAP-PZJWPPBQSA-N 0.000 claims 1
- MCHIQGKFWOWFRH-NZQKXSOJSA-N [(6r,9as)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[5-(trifluoromethyl)pyridin-2-yl]methanone Chemical compound CC1=C(C)C(OCCOC)=CC=C1[C@@H]1N2CCN(C(=O)C=3N=CC(=CC=3)C(F)(F)F)C[C@@H]2CCC1 MCHIQGKFWOWFRH-NZQKXSOJSA-N 0.000 claims 1
- QDZYQJRLLGIERI-RBBKRZOGSA-N [(6r,9as)-6-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound CC1=C(C)C(OCCOC)=CC=C1[C@@H]1N2CCN(C(=O)C=3C=NC(=CC=3)C(F)(F)F)C[C@@H]2CCC1 QDZYQJRLLGIERI-RBBKRZOGSA-N 0.000 claims 1
- BFKICTDXOYQIHG-LADGPHEKSA-N [(6r,9as)-6-[4-(3-hydroxypropoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=C(OCCCO)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 BFKICTDXOYQIHG-LADGPHEKSA-N 0.000 claims 1
- VZFVQHSIJLMSRY-RBBKRZOGSA-N [(6r,9as)-6-[4-(3-hydroxypropoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound C1=C(OCCCO)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=NC(=CC=2)C(F)(F)F)=C1 VZFVQHSIJLMSRY-RBBKRZOGSA-N 0.000 claims 1
- FMHGYYFQJWONJS-JTHBVZDNSA-N [(6r,9as)-6-[4-(3-methoxypropoxy)-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound CC1=C(C)C(OCCCOC)=CC=C1[C@@H]1N2CCN(C(=O)C=3C=NC(=CC=3)C(F)(F)F)C[C@@H]2CCC1 FMHGYYFQJWONJS-JTHBVZDNSA-N 0.000 claims 1
- QAHFTQBJXGQLRM-QGCDCVKKSA-N [(6r,9as)-6-[4-[(2r)-2-hydroxypropoxy]-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-(6-chloropyridin-3-yl)methanone Chemical compound CC1=C(C)C(OC[C@H](O)C)=CC=C1[C@@H]1N2CCN(C(=O)C=3C=NC(Cl)=CC=3)C[C@@H]2CCC1 QAHFTQBJXGQLRM-QGCDCVKKSA-N 0.000 claims 1
- IDSYSPXIFOTVKN-WMTXJRDZSA-N [(6r,9as)-6-[4-[(2r)-3-amino-2-hydroxypropoxy]-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=C(OC[C@H](O)CN)C(C)=C(C)C([C@@H]2N3CCN(C[C@@H]3CCC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)=C1 IDSYSPXIFOTVKN-WMTXJRDZSA-N 0.000 claims 1
- QAHFTQBJXGQLRM-XUEUYAKLSA-N [(6r,9as)-6-[4-[(2s)-2-hydroxypropoxy]-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-(6-chloropyridin-3-yl)methanone Chemical compound CC1=C(C)C(OC[C@@H](O)C)=CC=C1[C@@H]1N2CCN(C(=O)C=3C=NC(Cl)=CC=3)C[C@@H]2CCC1 QAHFTQBJXGQLRM-XUEUYAKLSA-N 0.000 claims 1
- GQFVLRUQRWKMFC-XUEUYAKLSA-N [(6r,9as)-6-[4-[(2s)-2-hydroxypropoxy]-2,3-dimethylphenyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound CC1=C(C)C(OC[C@@H](O)C)=CC=C1[C@@H]1N2CCN(C(=O)C=3C=NC(=CC=3)C(F)(F)F)C[C@@H]2CCC1 GQFVLRUQRWKMFC-XUEUYAKLSA-N 0.000 claims 1
- YENXBHWUANIYDX-LJQANCHMSA-N [4-[(1r)-1-[2,3-dimethyl-4-[2-(methylamino)ethoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCNC)=CC=C1[C@@H](C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 YENXBHWUANIYDX-LJQANCHMSA-N 0.000 claims 1
- ZFGDBNKXKYDYQW-HXUWFJFHSA-N [4-[(1r)-1-[2,3-dimethyl-4-[3-(methylamino)propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNC)=CC=C1[C@@H](C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 ZFGDBNKXKYDYQW-HXUWFJFHSA-N 0.000 claims 1
- KZLHJTJUCNOPPV-GOSISDBHSA-N [4-[(1r)-1-[4-(2-aminoethoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCN)=CC=2)C)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 KZLHJTJUCNOPPV-GOSISDBHSA-N 0.000 claims 1
- IWLYQLOXGBPOFB-HXUWFJFHSA-N [4-[(1r)-1-[4-(3-amino-3-methylbutoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-(4-chlorophenyl)methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCC(C)(C)N)=CC=2)C)CCN1C(=O)C1=CC=C(Cl)C=C1 IWLYQLOXGBPOFB-HXUWFJFHSA-N 0.000 claims 1
- ISJSZYRMTNNGKO-HXUWFJFHSA-N [4-[(1r)-1-[4-(3-amino-3-methylbutoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCC(C)(C)N)=CC=2)C)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 ISJSZYRMTNNGKO-HXUWFJFHSA-N 0.000 claims 1
- ZSRLKTAVZPZTCH-LJQANCHMSA-N [4-[(1r)-1-[4-(3-aminopropoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCCN)=CC=2)C)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 ZSRLKTAVZPZTCH-LJQANCHMSA-N 0.000 claims 1
- KGWDZPBRJBSJST-HXUWFJFHSA-N [4-[(1r)-1-[4-[2-(dimethylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCN(C)C)=CC=2)C)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 KGWDZPBRJBSJST-HXUWFJFHSA-N 0.000 claims 1
- DHHVDYHDCVOZEX-OAQYLSRUSA-N [4-[(1r)-1-[4-[3-(dimethylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN([C@H](C)C=2C(=C(C)C(OCCCN(C)C)=CC=2)C)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 DHHVDYHDCVOZEX-OAQYLSRUSA-N 0.000 claims 1
- DHHVDYHDCVOZEX-NRFANRHFSA-N [4-[(1s)-1-[4-[3-(dimethylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN([C@@H](C)C=2C(=C(C)C(OCCCN(C)C)=CC=2)C)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 DHHVDYHDCVOZEX-NRFANRHFSA-N 0.000 claims 1
- MEARJWADGPMUBB-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-(2-methylsulfanylethoxy)phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCSC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 MEARJWADGPMUBB-UHFFFAOYSA-N 0.000 claims 1
- SHLJDSZOXRPXJA-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-(2-methylsulfonylethoxy)phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCS(C)(=O)=O)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 SHLJDSZOXRPXJA-UHFFFAOYSA-N 0.000 claims 1
- CYVDEBZUEAELEA-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[2-(propan-2-ylamino)ethoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCNC(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 CYVDEBZUEAELEA-UHFFFAOYSA-N 0.000 claims 1
- PRGQBBSZNGRPLK-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[2-(propylamino)ethoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCNCCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 PRGQBBSZNGRPLK-UHFFFAOYSA-N 0.000 claims 1
- LQAQMAFXAQEQJU-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[2-[(4-methylcyclohexyl)amino]ethoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCNC2CCC(C)CC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 LQAQMAFXAQEQJU-UHFFFAOYSA-N 0.000 claims 1
- SXXMCQZSSTXYLV-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[2-[methyl(propan-2-yl)amino]ethoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCN(C)C(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 SXXMCQZSSTXYLV-UHFFFAOYSA-N 0.000 claims 1
- QCCYZOLBDBJNEG-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-(2-methylbutylamino)propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNCC(C)CC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 QCCYZOLBDBJNEG-UHFFFAOYSA-N 0.000 claims 1
- AYYCZTBXHORBSB-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-(2-methylpropylamino)propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNCC(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 AYYCZTBXHORBSB-UHFFFAOYSA-N 0.000 claims 1
- XLYBTOOJGDCWBP-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-(2-propan-2-yloxyethylamino)propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNCCOC(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 XLYBTOOJGDCWBP-UHFFFAOYSA-N 0.000 claims 1
- GYDJOMVJAOGHRY-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-(3-methylbutan-2-ylamino)propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNC(C)C(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 GYDJOMVJAOGHRY-UHFFFAOYSA-N 0.000 claims 1
- RPOWKLGWWRRGDT-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-(propan-2-ylamino)propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNC(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 RPOWKLGWWRRGDT-UHFFFAOYSA-N 0.000 claims 1
- VFQITYZGUMILHH-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-(propylamino)propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNCCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 VFQITYZGUMILHH-UHFFFAOYSA-N 0.000 claims 1
- BYHINRQBNOHLNZ-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-[methyl(propan-2-yl)amino]propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCN(C)C(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 BYHINRQBNOHLNZ-UHFFFAOYSA-N 0.000 claims 1
- JTIDBZDOQLLHQY-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[3-[methyl(propyl)amino]propoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCN(C)CCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 JTIDBZDOQLLHQY-UHFFFAOYSA-N 0.000 claims 1
- GGXLOWRNEFEBLN-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-(2-methylbutylamino)butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNCC(C)CC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 GGXLOWRNEFEBLN-UHFFFAOYSA-N 0.000 claims 1
- NULMKPKIGUVVME-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-(2-methylpropylamino)butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNCC(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 NULMKPKIGUVVME-UHFFFAOYSA-N 0.000 claims 1
- QVGVGEMEOFSMEC-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-(2-propan-2-yloxyethylamino)butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNCCOC(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 QVGVGEMEOFSMEC-UHFFFAOYSA-N 0.000 claims 1
- QVHVUCWBJUQFMG-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-(propan-2-ylamino)butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNC(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 QVHVUCWBJUQFMG-UHFFFAOYSA-N 0.000 claims 1
- UPKHSUGSDFNKLN-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-(propylamino)butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNCCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 UPKHSUGSDFNKLN-UHFFFAOYSA-N 0.000 claims 1
- IYJRUTSPIFBHJZ-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-[(2-methylcyclohexyl)amino]butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCCNC2C(CCCC2)C)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 IYJRUTSPIFBHJZ-UHFFFAOYSA-N 0.000 claims 1
- NMUVJSKBGKHUHD-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-[(4-methylcyclohexyl)amino]butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCCNC2CCC(C)CC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 NMUVJSKBGKHUHD-UHFFFAOYSA-N 0.000 claims 1
- UNASFKJSCPMMNQ-UHFFFAOYSA-N [4-[1-[2,3-dimethyl-4-[4-[methyl(propan-2-yl)amino]butoxy]phenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCN(C)C(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 UNASFKJSCPMMNQ-UHFFFAOYSA-N 0.000 claims 1
- GJCVORSBBKHQHN-UHFFFAOYSA-N [4-[1-[4-(2-methoxyethoxy)-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCOC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 GJCVORSBBKHQHN-UHFFFAOYSA-N 0.000 claims 1
- YENDXWBOFKIQGM-GWQXNCQPSA-N [4-[1-[4-[(2r)-3-(dimethylamino)-2-hydroxypropoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OC[C@H](O)CN(C)C)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 YENDXWBOFKIQGM-GWQXNCQPSA-N 0.000 claims 1
- ZPNJLSRZGVPBIQ-BDPMCISCSA-N [4-[1-[4-[(2r)-3-amino-2-hydroxypropoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OC[C@H](O)CN)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 ZPNJLSRZGVPBIQ-BDPMCISCSA-N 0.000 claims 1
- PUFJRMXPPSIFAA-UHFFFAOYSA-N [4-[1-[4-[2-(2-ethoxyethylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCNCCOCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 PUFJRMXPPSIFAA-UHFFFAOYSA-N 0.000 claims 1
- UTTZSZWLPPWMCG-UHFFFAOYSA-N [4-[1-[4-[2-(cyclobutylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCNC2CCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 UTTZSZWLPPWMCG-UHFFFAOYSA-N 0.000 claims 1
- ZWTXTERYAAIKAW-UHFFFAOYSA-N [4-[1-[4-[2-(cyclohexylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCNC2CCCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 ZWTXTERYAAIKAW-UHFFFAOYSA-N 0.000 claims 1
- OVHTXTVZHBWCRS-UHFFFAOYSA-N [4-[1-[4-[2-(cyclohexylmethylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCNCC2CCCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 OVHTXTVZHBWCRS-UHFFFAOYSA-N 0.000 claims 1
- UZTSZCCTIOEJCT-UHFFFAOYSA-N [4-[1-[4-[2-(cyclopentylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCNC2CCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 UZTSZCCTIOEJCT-UHFFFAOYSA-N 0.000 claims 1
- XLRCREIOTYTLHC-UHFFFAOYSA-N [4-[1-[4-[2-(cyclopropylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCNC2CC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 XLRCREIOTYTLHC-UHFFFAOYSA-N 0.000 claims 1
- FQECLUHAIGZULW-UHFFFAOYSA-N [4-[1-[4-[2-(cyclopropylmethylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCNCC2CC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 FQECLUHAIGZULW-UHFFFAOYSA-N 0.000 claims 1
- MQLMDGDGLZTTIR-UHFFFAOYSA-N [4-[1-[4-[2-(diethylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCN(CC)CC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 MQLMDGDGLZTTIR-UHFFFAOYSA-N 0.000 claims 1
- OLHCGJGPQBFXGA-UHFFFAOYSA-N [4-[1-[4-[2-(dipropylamino)ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCN(CCC)CCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 OLHCGJGPQBFXGA-UHFFFAOYSA-N 0.000 claims 1
- WIGWHUIZEZVKDB-UHFFFAOYSA-N [4-[1-[4-[2-[butyl(methyl)amino]ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCN(C)CCCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 WIGWHUIZEZVKDB-UHFFFAOYSA-N 0.000 claims 1
- MSQYFAJNWCWMBT-UHFFFAOYSA-N [4-[1-[4-[2-[cyclohexyl(methyl)amino]ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCN(C)C2CCCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 MSQYFAJNWCWMBT-UHFFFAOYSA-N 0.000 claims 1
- QSWMJBYIJYOADE-UHFFFAOYSA-N [4-[1-[4-[2-[di(propan-2-yl)amino]ethoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCN(C(C)C)C(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 QSWMJBYIJYOADE-UHFFFAOYSA-N 0.000 claims 1
- VNGNJCKIFKJSAF-UHFFFAOYSA-N [4-[1-[4-[3-(1-methoxypropan-2-ylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNC(C)COC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 VNGNJCKIFKJSAF-UHFFFAOYSA-N 0.000 claims 1
- QCGHDRVUCAMBRL-UHFFFAOYSA-N [4-[1-[4-[3-(2,2-dimethylpropylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCNCC(C)(C)C)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 QCGHDRVUCAMBRL-UHFFFAOYSA-N 0.000 claims 1
- VDVJKNDCZOGPSW-UHFFFAOYSA-N [4-[1-[4-[3-(2-ethoxyethylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNCCOCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 VDVJKNDCZOGPSW-UHFFFAOYSA-N 0.000 claims 1
- YQNMZZOWMPUSFW-UHFFFAOYSA-N [4-[1-[4-[3-(butan-2-ylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCNC(C)CC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 YQNMZZOWMPUSFW-UHFFFAOYSA-N 0.000 claims 1
- ZDKGWFLQVUQOJN-UHFFFAOYSA-N [4-[1-[4-[3-(cyclohexylmethylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCNCC2CCCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 ZDKGWFLQVUQOJN-UHFFFAOYSA-N 0.000 claims 1
- URSKCGPUYWLOIB-UHFFFAOYSA-N [4-[1-[4-[3-(cyclopentylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCNC2CCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 URSKCGPUYWLOIB-UHFFFAOYSA-N 0.000 claims 1
- PATOQIYCRDSNPH-UHFFFAOYSA-N [4-[1-[4-[3-(cyclopropylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCNC2CC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 PATOQIYCRDSNPH-UHFFFAOYSA-N 0.000 claims 1
- OKXXATHMOLQJLB-UHFFFAOYSA-N [4-[1-[4-[3-(cyclopropylmethylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCNCC2CC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 OKXXATHMOLQJLB-UHFFFAOYSA-N 0.000 claims 1
- CHAZOFAMZMDVFJ-UHFFFAOYSA-N [4-[1-[4-[3-(diethylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCN(CC)CC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 CHAZOFAMZMDVFJ-UHFFFAOYSA-N 0.000 claims 1
- DHHVDYHDCVOZEX-UHFFFAOYSA-N [4-[1-[4-[3-(dimethylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCN(C)C)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 DHHVDYHDCVOZEX-UHFFFAOYSA-N 0.000 claims 1
- BQJMRPMPYXDBIX-UHFFFAOYSA-N [4-[1-[4-[3-(dipropylamino)propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCN(CCC)CCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 BQJMRPMPYXDBIX-UHFFFAOYSA-N 0.000 claims 1
- UCCWVSWLDXEKAD-UHFFFAOYSA-N [4-[1-[4-[3-[butyl(methyl)amino]propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCN(C)CCCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 UCCWVSWLDXEKAD-UHFFFAOYSA-N 0.000 claims 1
- YKXHZDXGOHSERU-UHFFFAOYSA-N [4-[1-[4-[3-[cyclohexyl(ethyl)amino]propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CCCCC1N(CC)CCCOC(C(=C1C)C)=CC=C1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 YKXHZDXGOHSERU-UHFFFAOYSA-N 0.000 claims 1
- YQUXZTQZKCXUAV-UHFFFAOYSA-N [4-[1-[4-[3-[cyclohexyl(methyl)amino]propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCN(C)C2CCCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 YQUXZTQZKCXUAV-UHFFFAOYSA-N 0.000 claims 1
- QBSADLASCNPAEE-UHFFFAOYSA-N [4-[1-[4-[3-[di(propan-2-yl)amino]propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCN(C(C)C)C(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 QBSADLASCNPAEE-UHFFFAOYSA-N 0.000 claims 1
- BCLVBSYJTDAIHK-UHFFFAOYSA-N [4-[1-[4-[3-[ethyl(propan-2-yl)amino]propoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCN(CC)C(C)C)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 BCLVBSYJTDAIHK-UHFFFAOYSA-N 0.000 claims 1
- NWXJFITXBIUMEL-UHFFFAOYSA-N [4-[1-[4-[4-(1-methoxypropan-2-ylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNC(C)COC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 NWXJFITXBIUMEL-UHFFFAOYSA-N 0.000 claims 1
- OBNZFQPEXDDAEI-UHFFFAOYSA-N [4-[1-[4-[4-(2,2-dimethylpropylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCCNCC(C)(C)C)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 OBNZFQPEXDDAEI-UHFFFAOYSA-N 0.000 claims 1
- ABYQBHGTUUKZMD-UHFFFAOYSA-N [4-[1-[4-[4-(2-ethoxyethylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNCCOCC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 ABYQBHGTUUKZMD-UHFFFAOYSA-N 0.000 claims 1
- HQUVTNTZTVWWHY-UHFFFAOYSA-N [4-[1-[4-[4-(butan-2-ylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCNC(C)CC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 HQUVTNTZTVWWHY-UHFFFAOYSA-N 0.000 claims 1
- JFLHSTXRVFMCGC-UHFFFAOYSA-N [4-[1-[4-[4-(cyclobutylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCCNC2CCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 JFLHSTXRVFMCGC-UHFFFAOYSA-N 0.000 claims 1
- VOAKLUUWLUHHGQ-UHFFFAOYSA-N [4-[1-[4-[4-(cyclohexylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCCNC2CCCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 VOAKLUUWLUHHGQ-UHFFFAOYSA-N 0.000 claims 1
- VQNPALBBFYPBCY-UHFFFAOYSA-N [4-[1-[4-[4-(cyclohexylmethylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCCNCC2CCCCC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 VQNPALBBFYPBCY-UHFFFAOYSA-N 0.000 claims 1
- AXVUKTPBINVMPU-UHFFFAOYSA-N [4-[1-[4-[4-(cyclopropylmethylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=C(OCCCCNCC2CC2)C(C)=C(C)C=1C(C)N(CC1)CCN1C(=O)C1=CC=C(C(F)(F)F)C=C1 AXVUKTPBINVMPU-UHFFFAOYSA-N 0.000 claims 1
- IDVWEVATSAFLBQ-UHFFFAOYSA-N [4-[1-[4-[4-(diethylamino)butoxy]-2,3-dimethylphenyl]ethyl]piperazin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(C)C(OCCCCN(CC)CC)=CC=C1C(C)N1CCN(C(=O)C=2C=CC(=CC=2)C(F)(F)F)CC1 IDVWEVATSAFLBQ-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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US58095804P | 2004-06-17 | 2004-06-17 |
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ZA200610152B true ZA200610152B (en) | 2008-01-30 |
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ZA200610152A ZA200610152B (en) | 2004-06-17 | 2006-12-05 | Aryl-substituted piperazine derivatives |
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US (1) | US20060009456A1 (pt) |
EP (1) | EP1756107A2 (pt) |
JP (1) | JP2008503477A (pt) |
KR (1) | KR20070027600A (pt) |
CN (1) | CN101048405A (pt) |
AU (1) | AU2005265051A1 (pt) |
BR (1) | BRPI0512274A (pt) |
CA (1) | CA2567604A1 (pt) |
IL (1) | IL179350A0 (pt) |
MX (1) | MXPA06014748A (pt) |
NO (1) | NO20070293L (pt) |
RU (1) | RU2007101501A (pt) |
SG (1) | SG155958A1 (pt) |
TW (1) | TW200609219A (pt) |
WO (1) | WO2006009789A2 (pt) |
ZA (1) | ZA200610152B (pt) |
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CA2462200A1 (en) * | 2001-08-10 | 2003-02-20 | Palatin Technologies, Inc. | Peptidomimetics of biologically active metallopeptides |
US7732451B2 (en) * | 2001-08-10 | 2010-06-08 | Palatin Technologies, Inc. | Naphthalene-containing melanocortin receptor-specific small molecule |
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US7727990B2 (en) | 2003-05-01 | 2010-06-01 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine and keto-piperazine compounds |
US7968548B2 (en) * | 2003-05-01 | 2011-06-28 | Palatin Technologies, Inc. | Melanocortin receptor-specific piperazine compounds with diamine groups |
US7709484B1 (en) | 2004-04-19 | 2010-05-04 | Palatin Technologies, Inc. | Substituted melanocortin receptor-specific piperazine compounds |
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JP5121346B2 (ja) * | 2007-08-07 | 2013-01-16 | 国立大学法人 長崎大学 | 光学活性プロリンエステル誘導体およびn−ホルミル光学活性プロリン誘導体の製造方法 |
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WO2010075356A1 (en) * | 2008-12-23 | 2010-07-01 | Forest Laboratories Holdings Limited | Novel piperazine derivatives as inhibitors of stearoyl-coa desaturase |
EP2419413B1 (en) * | 2009-04-16 | 2016-11-23 | Takeda Pharmaceutical Company Limited | Derivatives of n-acyl-n'-phenylpiperazine useful (inter alia) for the prophylaxis or treatment of diabetes |
CA2900335C (en) * | 2012-10-22 | 2021-10-26 | City Of Hope | Synthetic analogs of epipolythiodioxopiperazines and uses thereof |
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JP7088912B2 (ja) | 2016-09-15 | 2022-06-21 | シティ・オブ・ホープ | ジチオetp誘導体 |
JP7297214B2 (ja) * | 2017-09-28 | 2023-06-26 | 国立大学法人京都大学 | 魚類および魚類の生産方法 |
EP4076527A4 (en) * | 2020-01-10 | 2024-05-15 | Consynance Therapeutics Inc | COMBINATION DRUG THERAPIES AND THEIR METHODS OF USE |
HUP2200222A1 (hu) | 2022-06-17 | 2023-12-28 | Richter Gedeon Nyrt | MCHR1 antagonisták a Prader-Willi szindróma kezelésére |
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-
2005
- 2005-06-15 TW TW094119884A patent/TW200609219A/zh unknown
- 2005-06-16 US US11/154,986 patent/US20060009456A1/en not_active Abandoned
- 2005-06-16 JP JP2007516747A patent/JP2008503477A/ja not_active Withdrawn
- 2005-06-16 CA CA002567604A patent/CA2567604A1/en not_active Abandoned
- 2005-06-16 WO PCT/US2005/021340 patent/WO2006009789A2/en active Application Filing
- 2005-06-16 KR KR1020067026695A patent/KR20070027600A/ko not_active Application Discontinuation
- 2005-06-16 MX MXPA06014748A patent/MXPA06014748A/es not_active Application Discontinuation
- 2005-06-16 RU RU2007101501/04A patent/RU2007101501A/ru not_active Application Discontinuation
- 2005-06-16 EP EP05760258A patent/EP1756107A2/en not_active Withdrawn
- 2005-06-16 CN CNA2005800199546A patent/CN101048405A/zh active Pending
- 2005-06-16 AU AU2005265051A patent/AU2005265051A1/en not_active Abandoned
- 2005-06-16 BR BRPI0512274-0A patent/BRPI0512274A/pt not_active IP Right Cessation
- 2005-06-16 SG SG200906325-6A patent/SG155958A1/en unknown
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2006
- 2006-11-16 IL IL179350A patent/IL179350A0/en unknown
- 2006-12-05 ZA ZA200610152A patent/ZA200610152B/en unknown
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2007
- 2007-01-16 NO NO20070293A patent/NO20070293L/no not_active Application Discontinuation
Also Published As
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WO2006009789A2 (en) | 2006-01-26 |
WO2006009789A3 (en) | 2006-12-28 |
CA2567604A1 (en) | 2006-01-26 |
BRPI0512274A (pt) | 2008-02-19 |
US20060009456A1 (en) | 2006-01-12 |
TW200609219A (en) | 2006-03-16 |
AU2005265051A1 (en) | 2006-01-26 |
EP1756107A2 (en) | 2007-02-28 |
RU2007101501A (ru) | 2008-08-10 |
CN101048405A (zh) | 2007-10-03 |
IL179350A0 (en) | 2007-03-08 |
KR20070027600A (ko) | 2007-03-09 |
NO20070293L (no) | 2007-03-15 |
SG155958A1 (en) | 2009-10-29 |
JP2008503477A (ja) | 2008-02-07 |
MXPA06014748A (es) | 2007-03-21 |
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