JP2007506744A - 抗癌剤としての６−［（置換）フェニル］トリアゾロピリミジン類 - Google Patents

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Publication number

JP2007506744A

JP2007506744A JP2006528075A JP2006528075A JP2007506744A JP 2007506744 A JP2007506744 A JP 2007506744A JP 2006528075 A JP2006528075 A JP 2006528075A JP 2006528075 A JP2006528075 A JP 2006528075A JP 2007506744 A JP2007506744 A JP 2007506744A

Authority

JP

Japan

Prior art keywords

triazolo

chloro

trifluoro

pyrimidin

methylethyl

Prior art date

2003-09-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• -1 6-[(Substituted) phenyl] triazolopyrimidines Chemical class 0.000 title claims abstract description 61
• 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 241
• 150000003839 salts Chemical class 0.000 claims abstract description 131
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 77
• 238000000034 method Methods 0.000 claims abstract description 54
• 238000011282 treatment Methods 0.000 claims abstract description 28
• 201000011510 cancer Diseases 0.000 claims abstract description 26
• 241000124008 Mammalia Species 0.000 claims abstract description 24
• 230000036457 multidrug resistance Effects 0.000 claims abstract description 23
• 201000010099 disease Diseases 0.000 claims abstract description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
• 210000004881 tumor cell Anatomy 0.000 claims abstract description 12
• 230000005764 inhibitory process Effects 0.000 claims abstract description 8
• 230000002265 prevention Effects 0.000 claims abstract description 7
• 230000004663 cell proliferation Effects 0.000 claims abstract description 5
• 230000001737 promoting effect Effects 0.000 claims abstract description 5
• 230000004565 tumor cell growth Effects 0.000 claims abstract description 5
• 102000004243 Tubulin Human genes 0.000 claims description 49
• 108090000704 Tubulin Proteins 0.000 claims description 49
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 44
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
• 102000029749 Microtubule Human genes 0.000 claims description 31
• 108091022875 Microtubule Proteins 0.000 claims description 31
• 210000004688 microtubule Anatomy 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 17
• 230000012010 growth Effects 0.000 claims description 17
• 239000002585 base Substances 0.000 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 15
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 14
• NTADARNNAPPIBY-UHFFFAOYSA-N triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=CC=NC2=CN=NN12 NTADARNNAPPIBY-UHFFFAOYSA-N 0.000 claims description 14
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 239000002904 solvent Substances 0.000 claims description 13
• QOXCEADXSTZKHA-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=CC=NC2=NC=NN12 QOXCEADXSTZKHA-UHFFFAOYSA-N 0.000 claims description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• TUXZQBYIZLWUKK-AFIAKLHKSA-N (e)-but-2-enedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound OC(=O)\C=C\C(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl TUXZQBYIZLWUKK-AFIAKLHKSA-N 0.000 claims description 9
• MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 claims description 9
• ZSLWBWNJXMEWNY-JTQLQIEISA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN(C)C)C=C1F ZSLWBWNJXMEWNY-JTQLQIEISA-N 0.000 claims description 9
• 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 9
• 150000008041 alkali metal carbonates Chemical class 0.000 claims description 9
• 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 9
• 239000000010 aprotic solvent Substances 0.000 claims description 9
• 150000004683 dihydrates Chemical class 0.000 claims description 9
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• ZUZPCOQWSYNWLU-VIFPVBQESA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl ZUZPCOQWSYNWLU-VIFPVBQESA-N 0.000 claims description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 8
• ZUZPCOQWSYNWLU-SECBINFHSA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl ZUZPCOQWSYNWLU-SECBINFHSA-N 0.000 claims description 7
• HAFUDZOLFLXVIY-FVGYRXGTSA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine;hydrochloride Chemical compound Cl.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl HAFUDZOLFLXVIY-FVGYRXGTSA-N 0.000 claims description 7
• 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 7
• 150000008046 alkali metal hydrides Chemical class 0.000 claims description 7
• OVAKAPOZRCLUHN-FVGYRXGTSA-N butanedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound OC(=O)CCC(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl OVAKAPOZRCLUHN-FVGYRXGTSA-N 0.000 claims description 7
• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• VZCYOOQTPOCHFL-OWOJBTEDSA-N fumaric acid group Chemical group C(\C=C\C(=O)O)(=O)O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000004434 sulfur atom Chemical group 0.000 claims description 7
• VFFSFDFJZAYCBT-JTQLQIEISA-N 5-bromo-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound BrC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN(C)C)C=C1F VFFSFDFJZAYCBT-JTQLQIEISA-N 0.000 claims description 6
• SCUBGTBLFXCHHE-NSHDSACASA-N 5-chloro-6-[4-[4-(dimethylamino)butyl]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(CCCCN(C)C)C=C1F SCUBGTBLFXCHHE-NSHDSACASA-N 0.000 claims description 6
• 150000005690 diesters Chemical class 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• TURWXBQPPKQQIC-UHFFFAOYSA-N 4-[4-(4-oxobutylamino)butylamino]butanal Chemical compound O=CCCCNCCCCNCCCC=O TURWXBQPPKQQIC-UHFFFAOYSA-N 0.000 claims description 5
• MIZWZYPKIVHIRV-NSHDSACASA-N 5-chloro-6-[2,6-difluoro-4-(2-morpholin-4-ylethoxy)phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCN1CCOCC1 MIZWZYPKIVHIRV-NSHDSACASA-N 0.000 claims description 5
• ZYLQMJCSPMXOHL-QMMMGPOBSA-N 5-chloro-6-[2,6-difluoro-4-[2-(methylamino)ethoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl ZYLQMJCSPMXOHL-QMMMGPOBSA-N 0.000 claims description 5
• XAKKESNRKUXRPK-VIFPVBQESA-N 5-chloro-6-[3-[2-(dimethylamino)ethoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=CC(OCCN(C)C)=C1F XAKKESNRKUXRPK-VIFPVBQESA-N 0.000 claims description 5
• GXPIFHVEFPCZPS-JTQLQIEISA-N 5-chloro-6-[3-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=CC(OCCCN(C)C)=C1F GXPIFHVEFPCZPS-JTQLQIEISA-N 0.000 claims description 5
• QHBMOSBSGXNWHS-NSHDSACASA-N 5-chloro-6-[3-[4-(dimethylamino)butoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=CC(OCCCCN(C)C)=C1F QHBMOSBSGXNWHS-NSHDSACASA-N 0.000 claims description 5
• FDKOUKLCYAUQES-VIFPVBQESA-N 5-chloro-6-[4-[2-(dimethylamino)ethoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCN(C)C)C=C1F FDKOUKLCYAUQES-VIFPVBQESA-N 0.000 claims description 5
• KUPGUXGPNHKBCS-NSHDSACASA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2-fluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=CC=C(OCCCN(C)C)C=C1F KUPGUXGPNHKBCS-NSHDSACASA-N 0.000 claims description 5
• YTOAWZMMRBSRKF-JTQLQIEISA-N 5-chloro-6-[4-[3-(ethylamino)propoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNCC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl YTOAWZMMRBSRKF-JTQLQIEISA-N 0.000 claims description 5
• HAVQJWSGEOOVKZ-NSHDSACASA-N 5-chloro-6-[4-[4-(dimethylamino)butoxy]-2,6-difluorophenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCCN(C)C)C=C1F HAVQJWSGEOOVKZ-NSHDSACASA-N 0.000 claims description 5
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 5
• FWNIBMRSBSSPNP-DXYFNVQQSA-N butanedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine;dihydrate Chemical compound O.O.OC(=O)CCC(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl FWNIBMRSBSSPNP-DXYFNVQQSA-N 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
• SILNEJLZHQBBBR-UHFFFAOYSA-N 3-[4-(5-chloro-7-cycloheptyl-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)-3,5-difluorophenoxy]propan-1-ol Chemical compound FC1=CC(OCCCO)=CC(F)=C1C1=C(C2CCCCCC2)N2N=CN=C2N=C1Cl SILNEJLZHQBBBR-UHFFFAOYSA-N 0.000 claims description 3
• GHMHOHRZRISOHU-UHFFFAOYSA-N 5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCNC)=CC(F)=C1C1=C(NCC(F)(F)F)N2N=CN=C2N=C1Cl GHMHOHRZRISOHU-UHFFFAOYSA-N 0.000 claims description 3
• UYUJACMPNPNLMY-UHFFFAOYSA-N 5-chloro-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-(2,2,2-trifluoroethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound FC1=CC(OCCCN(C)C)=CC(F)=C1C1=C(NCC(F)(F)F)N2N=CN=C2N=C1Cl UYUJACMPNPNLMY-UHFFFAOYSA-N 0.000 claims description 3
• 239000001530 fumaric acid Substances 0.000 claims description 3
• UUFXQPPJVCARJY-CBVSRFFLSA-N (e)-but-2-enedioic acid;5-chloro-6-[2,6-difluoro-4-[3-(methylamino)propoxy]phenyl]-n-[(2s)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine;dihydrate Chemical compound O.O.OC(=O)\C=C\C(O)=O.FC1=CC(OCCCNC)=CC(F)=C1C1=C(N[C@@H](C)C(F)(F)F)N2N=CN=C2N=C1Cl UUFXQPPJVCARJY-CBVSRFFLSA-N 0.000 claims description 2
• XHWCCWGDJRYUJN-CGCSKFHYSA-N 1-[4-[5-chloro-7-[[(2R)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenyl]-N',N'-dimethylpropane-1,3-diamine Chemical compound ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)C(CCN(C)C)N)F)N[C@@H](C(F)(F)F)C)N=CN2 XHWCCWGDJRYUJN-CGCSKFHYSA-N 0.000 claims description 2
• VKQKHTMZJLSQTG-IAPIXIRKSA-N 1-[4-[5-chloro-7-[[(2R)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenyl]-N,N',N'-trimethylpropane-1,3-diamine Chemical compound ClC1=NC=2N(C(=C1C1=C(C=C(C=C1F)C(CCN(C)C)NC)F)N[C@@H](C(F)(F)F)C)N=CN=2 VKQKHTMZJLSQTG-IAPIXIRKSA-N 0.000 claims description 2
• LQUQZWNUVMXWOH-SSDOTTSWSA-N 2-[4-[5-chloro-7-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]ethanol Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCO)C=C1F LQUQZWNUVMXWOH-SSDOTTSWSA-N 0.000 claims description 2
• PYOBBMDUGURFMC-MRVPVSSYSA-N 3-[4-[5-chloro-7-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]propan-1-ol Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCO)C=C1F PYOBBMDUGURFMC-MRVPVSSYSA-N 0.000 claims description 2
• NSIRLJFAZOCMEI-SECBINFHSA-N 4-[4-[5-chloro-7-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]-3,5-difluorophenoxy]butan-1-ol Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCCO)C=C1F NSIRLJFAZOCMEI-SECBINFHSA-N 0.000 claims description 2
• VFFSFDFJZAYCBT-SNVBAGLBSA-N 5-bromo-6-[4-[3-(dimethylamino)propoxy]-2,6-difluorophenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound BrC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C1=C(F)C=C(OCCCN(C)C)C=C1F VFFSFDFJZAYCBT-SNVBAGLBSA-N 0.000 claims description 2
• MIZWZYPKIVHIRV-LLVKDONJSA-N 5-chloro-6-[2,6-difluoro-4-(2-morpholin-4-ylethoxy)phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCN1CCOCC1 MIZWZYPKIVHIRV-LLVKDONJSA-N 0.000 claims description 2
• QKXFUKJAICMMGW-GFCCVEGCSA-N 5-chloro-6-[2,6-difluoro-4-(3-morpholin-4-ylpropoxy)phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCOCC1 QKXFUKJAICMMGW-GFCCVEGCSA-N 0.000 claims description 2
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• MEZUNAKNPOIBGG-GFCCVEGCSA-N 5-chloro-6-[2,6-difluoro-4-(3-pyrrolidin-1-ylpropoxy)phenyl]-n-[(2r)-1,1,1-trifluoropropan-2-yl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound ClC1=NC2=NC=NN2C(N[C@H](C)C(F)(F)F)=C1C(C(=C1)F)=C(F)C=C1OCCCN1CCCC1 MEZUNAKNPOIBGG-GFCCVEGCSA-N 0.000 claims description 2
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