TW202010500A - 作為a2a受體拮抗劑的吡唑並三唑並嘧啶衍生物 - Google Patents

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Publication number

TW202010500A

TW202010500A TW108112189A TW108112189A TW202010500A TW 202010500 A TW202010500 A TW 202010500A TW 108112189 A TW108112189 A TW 108112189A TW 108112189 A TW108112189 A TW 108112189A TW 202010500 A TW202010500 A TW 202010500A

Authority

TW

Taiwan

Prior art keywords

mmol

alkyl

group

methyl

amino

Prior art date

2018-04-08

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• 101150051188 Adora2a gene Proteins 0.000 title description 14
• 238000000034 method Methods 0.000 claims abstract description 31
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 12
• 201000011510 cancer Diseases 0.000 claims abstract description 7
• -1 -C 2-6 alkynyl Chemical group 0.000 claims description 209
• 150000001875 compounds Chemical class 0.000 claims description 178
• 125000000217 alkyl group Chemical group 0.000 claims description 93
• 125000000623 heterocyclic group Chemical group 0.000 claims description 68
• 125000003118 aryl group Chemical group 0.000 claims description 67
• 125000001072 heteroaryl group Chemical group 0.000 claims description 60
• 125000005842 heteroatom Chemical group 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 25
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
• 125000002950 monocyclic group Chemical group 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• 125000002619 bicyclic group Chemical group 0.000 claims description 16
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
• 150000002431 hydrogen Chemical class 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 5
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 125000003566 oxetanyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• QMIMHUDEVKGOTQ-DVQDXYAYSA-N (e)-n-[(1s)-1-(3-morpholin-4-ylphenyl)ethyl]-3-phenylprop-2-enamide Chemical compound N([C@@H](C)C=1C=C(C=CC=1)N1CCOCC1)C(=O)\C=C\C1=CC=CC=C1 QMIMHUDEVKGOTQ-DVQDXYAYSA-N 0.000 claims 1
• 125000002009 alkene group Chemical group 0.000 claims 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
• 229940127600 A2A receptor antagonist Drugs 0.000 abstract description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 718
• 235000019439 ethyl acetate Nutrition 0.000 description 348
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 301
• 239000000203 mixture Substances 0.000 description 256
• 238000005481 NMR spectroscopy Methods 0.000 description 178
• 239000011541 reaction mixture Substances 0.000 description 166
• 239000011734 sodium Substances 0.000 description 166
• 239000007821 HATU Substances 0.000 description 159
• 239000012267 brine Substances 0.000 description 157
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 157
• 239000000047 product Substances 0.000 description 144
• 239000012044 organic layer Substances 0.000 description 127
• LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 121
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 119
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
• 238000012746 preparative thin layer chromatography Methods 0.000 description 111
• 239000000243 solution Substances 0.000 description 105
• YHAAZHXNNDGYSU-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-2-phenylpropanoic acid Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)O)(C)C1=CC=CC=C1 YHAAZHXNNDGYSU-UHFFFAOYSA-N 0.000 description 81
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
• 239000007787 solid Substances 0.000 description 60
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
• 238000004440 column chromatography Methods 0.000 description 56
• 239000004698 Polyethylene Substances 0.000 description 44
• 238000006243 chemical reaction Methods 0.000 description 40
• 239000003921 oil Substances 0.000 description 37
• 239000003208 petroleum Substances 0.000 description 34
• YHAAZHXNNDGYSU-LJQANCHMSA-N (2R)-2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-2-phenylpropanoic acid Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2[C@](C(=O)O)(C)C1=CC=CC=C1 YHAAZHXNNDGYSU-LJQANCHMSA-N 0.000 description 33
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
• FNFSGOCNXWRVDV-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-2-phenylacetic acid Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)O)C1=CC=CC=C1 FNFSGOCNXWRVDV-UHFFFAOYSA-N 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• 210000004027 cell Anatomy 0.000 description 23
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• 239000000460 chlorine Substances 0.000 description 22
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 22
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
• 239000002253 acid Substances 0.000 description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
• 229910052717 sulfur Inorganic materials 0.000 description 15
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 11
• 201000010099 disease Diseases 0.000 description 11
• 238000004108 freeze drying Methods 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
• 238000000926 separation method Methods 0.000 description 11
• 238000004809 thin layer chromatography Methods 0.000 description 11
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 10
• 238000002953 preparative HPLC Methods 0.000 description 10
• VJXPRLZGWQAQEX-UHFFFAOYSA-N 3-(aminomethyl)oxetan-3-ol Chemical compound NCC1(O)COC1 VJXPRLZGWQAQEX-UHFFFAOYSA-N 0.000 description 9
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 9
• 239000000706 filtrate Substances 0.000 description 9
• 238000011282 treatment Methods 0.000 description 9
• 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 8
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 239000002126 C01EB10 - Adenosine Substances 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
• 229960005305 adenosine Drugs 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 150000002430 hydrocarbons Chemical group 0.000 description 7
• 239000011593 sulfur Substances 0.000 description 7
• YHAAZHXNNDGYSU-IBGZPJMESA-N (2S)-2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-2-phenylpropanoic acid Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2[C@@](C(=O)O)(C)C1=CC=CC=C1 YHAAZHXNNDGYSU-IBGZPJMESA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 239000012065 filter cake Substances 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• YKWJNVFPKLFRRE-UHFFFAOYSA-N chembl276738 Chemical compound N=1N2C(N)=NC=3NN=CC=3C2=NC=1C1=CC=CO1 YKWJNVFPKLFRRE-UHFFFAOYSA-N 0.000 description 5
• 239000003153 chemical reaction reagent Substances 0.000 description 5
• 238000004587 chromatography analysis Methods 0.000 description 5
• 239000012043 crude product Substances 0.000 description 5
• 125000004122 cyclic group Chemical group 0.000 description 5
• 208000035475 disorder Diseases 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 208000024891 symptom Diseases 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
• KUKASNZJTIKRMH-UHFFFAOYSA-N 4-amino-1-methylcyclohexan-1-ol Chemical compound CC1(O)CCC(N)CC1 KUKASNZJTIKRMH-UHFFFAOYSA-N 0.000 description 4
• RKTQEVMZBCBOSB-UHFFFAOYSA-N 4-aminocyclohexan-1-ol;hydron;chloride Chemical compound Cl.NC1CCC(O)CC1 RKTQEVMZBCBOSB-UHFFFAOYSA-N 0.000 description 4
• 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 4
• 101150007969 ADORA1 gene Proteins 0.000 description 4
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
• 102000055025 Adenosine deaminases Human genes 0.000 description 4
• 108050000203 Adenosine receptors Proteins 0.000 description 4
• 102000009346 Adenosine receptors Human genes 0.000 description 4
• 101150078577 Adora2b gene Proteins 0.000 description 4
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
• 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
• 241001465754 Metazoa Species 0.000 description 4
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
• 230000002378 acidificating effect Effects 0.000 description 4
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 4
• 230000008499 blood brain barrier function Effects 0.000 description 4
• 210000004556 brain Anatomy 0.000 description 4
• 239000000872 buffer Substances 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
• 239000012636 effector Substances 0.000 description 4
• 239000012091 fetal bovine serum Substances 0.000 description 4
• 239000012458 free base Substances 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• 239000012528 membrane Substances 0.000 description 4
• CZDNPVLPBZNWGF-UHFFFAOYSA-N methyl 2-bromo-2-phenylbutanoate Chemical compound COC(=O)C(Br)(CC)C1=CC=CC=C1 CZDNPVLPBZNWGF-UHFFFAOYSA-N 0.000 description 4
• 125000004430 oxygen atom Chemical group O* 0.000 description 4
• 125000006413 ring segment Chemical group 0.000 description 4
• 239000012258 stirred mixture Substances 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• PQMCFTMVQORYJC-RITPCOANSA-N (1s,2r)-2-aminocyclohexan-1-ol Chemical compound N[C@@H]1CCCC[C@@H]1O PQMCFTMVQORYJC-RITPCOANSA-N 0.000 description 3
• ZFSXKSSWYSZPGQ-JBUOLDKXSA-N (1s,2r)-2-aminocyclopentan-1-ol;hydrochloride Chemical compound Cl.N[C@@H]1CCC[C@@H]1O ZFSXKSSWYSZPGQ-JBUOLDKXSA-N 0.000 description 3
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