CA2827072C - Diaminopyrimidine derivatives and processes for the preparation thereof - Google Patents

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Publication number

CA2827072C

CA2827072C CA2827072A CA2827072A CA2827072C CA 2827072 C CA2827072 C CA 2827072C CA 2827072 A CA2827072 A CA 2827072A CA 2827072 A CA2827072 A CA 2827072A CA 2827072 C CA2827072 C CA 2827072C

Authority

CA

Canada

Prior art keywords

propylpyrimidin

group

piperidin

amine

optionally substituted

Prior art date

2011-02-25

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.)

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• 238000002360 preparation method Methods 0.000 title abstract description 144
• 238000000034 method Methods 0.000 title abstract description 96
• MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 title abstract description 12
• 230000008569 process Effects 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 331
• 150000003839 salts Chemical class 0.000 claims abstract description 76
• 206010010774 Constipation Diseases 0.000 claims abstract description 24
• 238000004519 manufacturing process Methods 0.000 claims abstract description 24
• 230000005176 gastrointestinal motility Effects 0.000 claims abstract description 23
• 230000004064 dysfunction Effects 0.000 claims abstract description 21
• 206010021518 Impaired gastric emptying Diseases 0.000 claims abstract description 16
• 239000003814 drug Substances 0.000 claims abstract description 16
• 208000021302 gastroesophageal reflux disease Diseases 0.000 claims abstract description 16
• 208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 201000006549 dyspepsia Diseases 0.000 claims abstract description 14
• 206010052105 Gastrointestinal hypomotility Diseases 0.000 claims abstract description 8
• 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 claims abstract description 8
• 230000003111 delayed effect Effects 0.000 claims abstract description 8
• 229940079593 drug Drugs 0.000 claims abstract description 8
• 208000001288 gastroparesis Diseases 0.000 claims abstract description 8
• 206010017753 Gastric atony Diseases 0.000 claims abstract description 7
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
• 206010054048 Postoperative ileus Diseases 0.000 claims abstract description 6
• -1 hydroxy, amino Chemical group 0.000 claims description 267
• 229910052736 halogen Inorganic materials 0.000 claims description 202
• 150000002367 halogens Chemical group 0.000 claims description 202
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 186
• 125000000217 alkyl group Chemical group 0.000 claims description 185
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 168
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 153
• 125000003545 alkoxy group Chemical group 0.000 claims description 141
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 133
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 127
• 125000001424 substituent group Chemical group 0.000 claims description 122
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 109
• 229910052739 hydrogen Inorganic materials 0.000 claims description 94
• 239000001257 hydrogen Substances 0.000 claims description 93
• 125000003282 alkyl amino group Chemical group 0.000 claims description 78
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
• 125000002541 furyl group Chemical group 0.000 claims description 60
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 54
• 125000003386 piperidinyl group Chemical group 0.000 claims description 54
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 51
• 125000002971 oxazolyl group Chemical group 0.000 claims description 45
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 45
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 45
• 125000004076 pyridyl group Chemical group 0.000 claims description 45
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 45
• 125000000335 thiazolyl group Chemical group 0.000 claims description 45
• 125000001544 thienyl group Chemical group 0.000 claims description 45
• 125000001425 triazolyl group Chemical group 0.000 claims description 45
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 44
• 125000002883 imidazolyl group Chemical group 0.000 claims description 43
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 39
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 37
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 33
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 31
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 30
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 30
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
• 125000001072 heteroaryl group Chemical group 0.000 claims description 30
• 125000001041 indolyl group Chemical group 0.000 claims description 30
• 125000004193 piperazinyl group Chemical group 0.000 claims description 30
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 28
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 28
• 125000004414 alkyl thio group Chemical group 0.000 claims description 25
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 24
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 24
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 19
• 230000026030 halogenation Effects 0.000 claims description 16
• 238000005658 halogenation reaction Methods 0.000 claims description 16
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 15
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 15
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 15
• 125000002393 azetidinyl group Chemical group 0.000 claims description 15
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 15
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 15
• 125000004122 cyclic group Chemical group 0.000 claims description 15
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 15
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 15
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 15
• 125000001624 naphthyl group Chemical group 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 15
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 15
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 15
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 15
• 125000006242 amine protecting group Chemical group 0.000 claims description 14
• 125000006560 (C1-C5)alkylcarbonylamino group Chemical group 0.000 claims description 13
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 13
• 125000000597 dioxinyl group Chemical group 0.000 claims description 13
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 13
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 11
• 150000007524 organic acids Chemical class 0.000 claims description 11
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 9
• 150000001266 acyl halides Chemical class 0.000 claims description 8
• 238000006268 reductive amination reaction Methods 0.000 claims description 8
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 7
• 230000029936 alkylation Effects 0.000 claims description 6
• 238000005804 alkylation reaction Methods 0.000 claims description 6
• 230000011987 methylation Effects 0.000 claims description 6
• 238000007069 methylation reaction Methods 0.000 claims description 6
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 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
• JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• VTDLCIODLRQPIM-QFIPXVFZSA-N 5-[[4-[(3s)-3-(butylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound C1[C@@H](NCCCC)CCCN1C1=CC(CCC)=NC(NC=2C=C(C(C)=CC=2)C#N)=N1 VTDLCIODLRQPIM-QFIPXVFZSA-N 0.000 claims description 3
• 150000002576 ketones Chemical class 0.000 claims description 3
• DTTWMEHMQXHPRJ-UHFFFAOYSA-N 3-[(4-morpholin-4-yl-6-propylpyrimidin-2-yl)amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=CC(C#N)=C1 DTTWMEHMQXHPRJ-UHFFFAOYSA-N 0.000 claims description 2
• ZSQYMJMRKQITCD-QFIPXVFZSA-N 5-[[4-[(3s)-3-(2,2-dimethylpropylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCC(C)(C)C)=NC=1NC1=CC=C(C)C(C#N)=C1 ZSQYMJMRKQITCD-QFIPXVFZSA-N 0.000 claims description 2
• CXMBOYJCMCTJQE-UHFFFAOYSA-N n-(4-morpholin-4-yl-6-propylpyrimidin-2-yl)quinolin-3-amine Chemical compound N=1C(NC=2C=C3C=CC=CC3=NC=2)=NC(CCC)=CC=1N1CCOCC1 CXMBOYJCMCTJQE-UHFFFAOYSA-N 0.000 claims description 2
• ROMHTURHCWXYKB-UHFFFAOYSA-N n-(4-morpholin-4-yl-6-propylpyrimidin-2-yl)quinolin-6-amine Chemical compound N=1C(NC=2C=C3C=CC=NC3=CC=2)=NC(CCC)=CC=1N1CCOCC1 ROMHTURHCWXYKB-UHFFFAOYSA-N 0.000 claims description 2
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 6
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
• 150000002431 hydrogen Chemical class 0.000 claims 3
• DJSXNTNWFPQMLV-HXUWFJFHSA-N 5-[[4-[(3r)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC=C(C)C(C#N)=C1 DJSXNTNWFPQMLV-HXUWFJFHSA-N 0.000 claims 2
• JZJGKYLHIAZCGA-GOSISDBHSA-N 1-N-[4-[(3R)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-4-fluorobenzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC=C(F)C(N)=C1 JZJGKYLHIAZCGA-GOSISDBHSA-N 0.000 claims 1
• VLAMRXPERXHEKD-MRXNPFEDSA-N 1-N-[4-[(3R)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-4-fluorobenzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC=C(F)C(N)=C1 VLAMRXPERXHEKD-MRXNPFEDSA-N 0.000 claims 1
• MIXLENXWODMWQV-OAHLLOKOSA-N 1-N-[4-[(3R)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-2-nitrobenzene-1,4-diamine Chemical compound CN[C@H]1CN(CCC1)C1=NC(=NC(=C1)CCC)NC1=C(C=C(C=C1)N)[N+](=O)[O-] MIXLENXWODMWQV-OAHLLOKOSA-N 0.000 claims 1
• NJXHNSMNMLDJHL-OAHLLOKOSA-N 1-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]-4-methylbenzene-1,3-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(N)=C1 NJXHNSMNMLDJHL-OAHLLOKOSA-N 0.000 claims 1
• JGIJETYGTIJKSZ-GFCCVEGCSA-N 1-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]-4-chlorobenzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(Cl)C(N)=C1 JGIJETYGTIJKSZ-GFCCVEGCSA-N 0.000 claims 1
• PXDZLXOFEVKLDS-GFCCVEGCSA-N 1-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]-4-fluorobenzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(F)C(N)=C1 PXDZLXOFEVKLDS-GFCCVEGCSA-N 0.000 claims 1
• IRSMBJOSKLUYNC-MRXNPFEDSA-N 1-N-[4-butyl-6-[(3R)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]-4-fluorobenzene-1,3-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(F)C(N)=C1 IRSMBJOSKLUYNC-MRXNPFEDSA-N 0.000 claims 1
• ZSTQZMMEZPZOST-QGZVFWFLSA-N 1-N-[4-butyl-6-[(3R)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]-4-methoxybenzene-1,3-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(OC)C(N)=C1 ZSTQZMMEZPZOST-QGZVFWFLSA-N 0.000 claims 1
• ZONYRFJPQVWYJC-GOSISDBHSA-N 1-N-[4-butyl-6-[(3R)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]-4-methylbenzene-1,3-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(N)=C1 ZONYRFJPQVWYJC-GOSISDBHSA-N 0.000 claims 1
• JBTKIVLIXDOMAO-UHFFFAOYSA-N 1-[2-(4-fluoroanilino)-6-methylpyrimidin-4-yl]piperidin-3-ol Chemical compound N=1C(C)=CC(N2CC(O)CCC2)=NC=1NC1=CC=C(F)C=C1 JBTKIVLIXDOMAO-UHFFFAOYSA-N 0.000 claims 1
• GQELAAMUHGGYSK-UHFFFAOYSA-N 1-[2-(4-fluoroanilino)-6-methylpyrimidin-4-yl]piperidin-4-ol Chemical compound N=1C(C)=CC(N2CCC(O)CC2)=NC=1NC1=CC=C(F)C=C1 GQELAAMUHGGYSK-UHFFFAOYSA-N 0.000 claims 1
• PDYICWDRZJPAIL-UHFFFAOYSA-N 1-[2-(4-fluoroanilino)-6-methylpyrimidin-4-yl]piperidin-4-one Chemical compound N=1C(C)=CC(N2CCC(=O)CC2)=NC=1NC1=CC=C(F)C=C1 PDYICWDRZJPAIL-UHFFFAOYSA-N 0.000 claims 1
• COKXGCGBFBVCSG-UHFFFAOYSA-N 1-[2-(4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidin-4-one Chemical compound N=1C(CCC)=CC(N2CCC(=O)CC2)=NC=1NC1=CC=C(F)C=C1 COKXGCGBFBVCSG-UHFFFAOYSA-N 0.000 claims 1
• ROMZYERADNDFOB-UHFFFAOYSA-N 1-[2-(4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidine-4-carboxamide Chemical compound N=1C(CCC)=CC(N2CCC(CC2)C(N)=O)=NC=1NC1=CC=C(F)C=C1 ROMZYERADNDFOB-UHFFFAOYSA-N 0.000 claims 1
• FIMKUCJAGCQMFH-MRXNPFEDSA-N 2-[(2r)-1-[2-(4-amino-3-nitroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2[C@H](CCCC2)CCO)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 FIMKUCJAGCQMFH-MRXNPFEDSA-N 0.000 claims 1
• UGRQMBRSDWHIAL-UHFFFAOYSA-N 2-[1-[2-(1h-indol-5-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3C=CNC3=CC=2)=NC(CCC)=CC=1N1CCCCC1CCO UGRQMBRSDWHIAL-UHFFFAOYSA-N 0.000 claims 1
• OMNRLWYFMYFZHV-UHFFFAOYSA-N 2-[1-[2-(1h-indol-6-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3NC=CC3=CC=2)=NC(CCC)=CC=1N1CCCCC1CCO OMNRLWYFMYFZHV-UHFFFAOYSA-N 0.000 claims 1
• UKILHJWFGGDZHU-UHFFFAOYSA-N 2-[1-[2-(2,3-dihydro-1h-indol-6-ylamino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3NCCC3=CC=2)=NC(CCC)=CC=1N1CCCCC1CCO UKILHJWFGGDZHU-UHFFFAOYSA-N 0.000 claims 1
• WPHAUJIHWCYYGR-UHFFFAOYSA-N 2-[1-[2-(3-amino-4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(F)C(N)=C1 WPHAUJIHWCYYGR-UHFFFAOYSA-N 0.000 claims 1
• BMTAWLUJXQPUAX-UHFFFAOYSA-N 2-[1-[2-(3-amino-4-methylanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(C)C(N)=C1 BMTAWLUJXQPUAX-UHFFFAOYSA-N 0.000 claims 1
• RMCOYWMUBIIAMV-UHFFFAOYSA-N 2-[1-[2-(3-chloro-4-methylanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(C)C(Cl)=C1 RMCOYWMUBIIAMV-UHFFFAOYSA-N 0.000 claims 1
• QIZLHLLRVFVJKX-UHFFFAOYSA-N 2-[1-[2-(3-chloroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=CC(Cl)=C1 QIZLHLLRVFVJKX-UHFFFAOYSA-N 0.000 claims 1
• UDRPOEMTJIZTDN-UHFFFAOYSA-N 2-[1-[2-(3-methylsulfanylanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=CC(SC)=C1 UDRPOEMTJIZTDN-UHFFFAOYSA-N 0.000 claims 1
• BRHNEJFCRVERSB-UHFFFAOYSA-N 2-[1-[2-(3-nitroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=CC([N+]([O-])=O)=C1 BRHNEJFCRVERSB-UHFFFAOYSA-N 0.000 claims 1
• FIMKUCJAGCQMFH-UHFFFAOYSA-N 2-[1-[2-(4-amino-3-nitroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 FIMKUCJAGCQMFH-UHFFFAOYSA-N 0.000 claims 1
• FMPGFFJBMLKHOC-UHFFFAOYSA-N 2-[1-[2-(4-chloro-3-nitroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FMPGFFJBMLKHOC-UHFFFAOYSA-N 0.000 claims 1
• VKWRXYWZVAWSIZ-UHFFFAOYSA-N 2-[1-[2-(4-fluoro-3-nitroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(F)C([N+]([O-])=O)=C1 VKWRXYWZVAWSIZ-UHFFFAOYSA-N 0.000 claims 1
• QSFYZOIVTCGBRQ-UHFFFAOYSA-N 2-[1-[2-(4-fluoroanilino)-6-methylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(C)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(F)C=C1 QSFYZOIVTCGBRQ-UHFFFAOYSA-N 0.000 claims 1
• ICQKTEHDZGAPTJ-UHFFFAOYSA-N 2-[1-[2-(4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(F)C=C1 ICQKTEHDZGAPTJ-UHFFFAOYSA-N 0.000 claims 1
• LTYPXMVAVIHTJX-UHFFFAOYSA-N 2-[1-[2-(4-methoxyanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(OC)C=C1 LTYPXMVAVIHTJX-UHFFFAOYSA-N 0.000 claims 1
• VOAVHXLLSWDWND-UHFFFAOYSA-N 2-[1-[2-(4-methyl-3-nitroanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(C)C([N+]([O-])=O)=C1 VOAVHXLLSWDWND-UHFFFAOYSA-N 0.000 claims 1
• ZOMOGMKWHIRVHN-UHFFFAOYSA-N 2-[1-[2-(5-methoxy-2-methylanilino)-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC(OC)=CC=C1C ZOMOGMKWHIRVHN-UHFFFAOYSA-N 0.000 claims 1
• UGSIJIXBOHUBLN-UHFFFAOYSA-N 2-[1-[2-[(1-ethylindol-6-yl)amino]-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3N(CC)C=CC3=CC=2)=NC(CCC)=CC=1N1CCCCC1CCO UGSIJIXBOHUBLN-UHFFFAOYSA-N 0.000 claims 1
• KQDIGTFJTSFMLJ-UHFFFAOYSA-N 2-[1-[2-[(2,3-dimethyl-1-benzofuran-5-yl)amino]-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3C(C)=C(C)OC3=CC=2)=NC(CCC)=CC=1N1CCCCC1CCO KQDIGTFJTSFMLJ-UHFFFAOYSA-N 0.000 claims 1
• ZVBHZRHLXKUJBV-UHFFFAOYSA-N 2-[1-[2-[4-amino-3-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 ZVBHZRHLXKUJBV-UHFFFAOYSA-N 0.000 claims 1
• ADCOPUPMIQBDAK-UHFFFAOYSA-N 2-[1-[6-butyl-2-(4-fluoroanilino)pyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(F)C=C1 ADCOPUPMIQBDAK-UHFFFAOYSA-N 0.000 claims 1
• ISMZFPAXZFFOJX-UHFFFAOYSA-N 2-[1-[6-ethyl-2-(4-fluoroanilino)pyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(F)C=C1 ISMZFPAXZFFOJX-UHFFFAOYSA-N 0.000 claims 1
• UYIAOAGPEMVSGJ-UHFFFAOYSA-N 2-[1-[6-propyl-2-(quinolin-3-ylamino)pyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3C=CC=CC3=NC=2)=NC(CCC)=CC=1N1CCCCC1CCO UYIAOAGPEMVSGJ-UHFFFAOYSA-N 0.000 claims 1
• ZLPBVHVFMADARA-UHFFFAOYSA-N 2-[1-[6-propyl-2-(quinolin-6-ylamino)pyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3C=CC=NC3=CC=2)=NC(CCC)=CC=1N1CCCCC1CCO ZLPBVHVFMADARA-UHFFFAOYSA-N 0.000 claims 1
• ADOFRJVYYWGNPN-UHFFFAOYSA-N 2-[1-[6-propyl-2-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=CC(C(F)(F)F)=C1 ADOFRJVYYWGNPN-UHFFFAOYSA-N 0.000 claims 1
• UKLCOCDKSQQQNW-UHFFFAOYSA-N 2-[1-[6-propyl-2-[[2-(trifluoromethyl)-3h-benzimidazol-5-yl]amino]pyrimidin-4-yl]piperidin-2-yl]ethanol Chemical compound N=1C(NC=2C=C3NC(=NC3=CC=2)C(F)(F)F)=NC(CCC)=CC=1N1CCCCC1CCO UKLCOCDKSQQQNW-UHFFFAOYSA-N 0.000 claims 1
• RPVNLNAMXWGUOS-CYBMUJFWSA-N 2-amino-5-[[4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(N)C(C#N)=C1 RPVNLNAMXWGUOS-CYBMUJFWSA-N 0.000 claims 1
• OUKPQBIGWXFETJ-QGZVFWFLSA-N 2-amino-5-[[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(N)C(C#N)=C1 OUKPQBIGWXFETJ-QGZVFWFLSA-N 0.000 claims 1
• WMNMDDZXRGEBIG-OAHLLOKOSA-N 2-amino-5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C(C#N)=C1 WMNMDDZXRGEBIG-OAHLLOKOSA-N 0.000 claims 1
• NTMCMRCRALBAGQ-CQSZACIVSA-N 2-amino-5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C(C#N)=C1 NTMCMRCRALBAGQ-CQSZACIVSA-N 0.000 claims 1
• KZDPFGISFODKGU-CYBMUJFWSA-N 2-fluoro-5-[[4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(F)C(C#N)=C1 KZDPFGISFODKGU-CYBMUJFWSA-N 0.000 claims 1
• CBBPCKFGPSJCSX-QGZVFWFLSA-N 2-fluoro-5-[[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(F)C(C#N)=C1 CBBPCKFGPSJCSX-QGZVFWFLSA-N 0.000 claims 1
• MGBZVZQJEHKSIF-UHFFFAOYSA-N 2-fluoro-5-[[4-[2-(2-hydroxyethyl)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=C(F)C(C#N)=C1 MGBZVZQJEHKSIF-UHFFFAOYSA-N 0.000 claims 1
• OYXKYJBLDDTJRJ-LJQANCHMSA-N 2-fluoro-5-[[4-propyl-6-[(3r)-3-(propylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound C1[C@H](NCCC)CCCN1C1=CC(CCC)=NC(NC=2C=C(C(F)=CC=2)C#N)=N1 OYXKYJBLDDTJRJ-LJQANCHMSA-N 0.000 claims 1
• SSULBKRHNALGQI-QGZVFWFLSA-N 2-hydroxy-n-[(3r)-1-[2-[4-methyl-3-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(C)C(C(F)(F)F)=C1 SSULBKRHNALGQI-QGZVFWFLSA-N 0.000 claims 1
• HKFXTVISMBZXSV-OAHLLOKOSA-N 2-methyl-5-[[4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(C)C(C#N)=C1 HKFXTVISMBZXSV-OAHLLOKOSA-N 0.000 claims 1
• NZXJQZKXZRYCCT-JOCHJYFZSA-N 2-methyl-5-[[4-[(3r)-3-(2-methylpropylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC(C)C)=NC=1NC1=CC=C(C)C(C#N)=C1 NZXJQZKXZRYCCT-JOCHJYFZSA-N 0.000 claims 1
• YTMTVUNQEJGNGP-HSZRJFAPSA-N 2-methyl-5-[[4-[(3r)-3-(3-methylbutylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCCC(C)C)=NC=1NC1=CC=C(C)C(C#N)=C1 YTMTVUNQEJGNGP-HSZRJFAPSA-N 0.000 claims 1
• FPMPMYAPEWYPFI-LJQANCHMSA-N 2-methyl-5-[[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(C#N)=C1 FPMPMYAPEWYPFI-LJQANCHMSA-N 0.000 claims 1
• DGSIKLSEJIWPAP-HSZRJFAPSA-N 2-methyl-5-[[4-[(3r)-3-(pentylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound C1[C@H](NCCCCC)CCCN1C1=CC(CCC)=NC(NC=2C=C(C(C)=CC=2)C#N)=N1 DGSIKLSEJIWPAP-HSZRJFAPSA-N 0.000 claims 1
• HPKQQZJAOJNCCE-OAQYLSRUSA-N 2-methyl-5-[[4-[(3r)-3-(propan-2-ylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)C)=NC=1NC1=CC=C(C)C(C#N)=C1 HPKQQZJAOJNCCE-OAQYLSRUSA-N 0.000 claims 1
• NZXJQZKXZRYCCT-QFIPXVFZSA-N 2-methyl-5-[[4-[(3s)-3-(2-methylpropylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCC(C)C)=NC=1NC1=CC=C(C)C(C#N)=C1 NZXJQZKXZRYCCT-QFIPXVFZSA-N 0.000 claims 1
• YTMTVUNQEJGNGP-QHCPKHFHSA-N 2-methyl-5-[[4-[(3s)-3-(3-methylbutylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCCC(C)C)=NC=1NC1=CC=C(C)C(C#N)=C1 YTMTVUNQEJGNGP-QHCPKHFHSA-N 0.000 claims 1
• WHCVMWDQQKXPTK-QFIPXVFZSA-N 2-methyl-5-[[4-[(3s)-3-(3-methylsulfanylpropylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCCCSC)=NC=1NC1=CC=C(C)C(C#N)=C1 WHCVMWDQQKXPTK-QFIPXVFZSA-N 0.000 claims 1
• DGSIKLSEJIWPAP-QHCPKHFHSA-N 2-methyl-5-[[4-[(3s)-3-(pentylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound C1[C@@H](NCCCCC)CCCN1C1=CC(CCC)=NC(NC=2C=C(C(C)=CC=2)C#N)=N1 DGSIKLSEJIWPAP-QHCPKHFHSA-N 0.000 claims 1
• NZRISDYAUFCGJF-HSZRJFAPSA-N 2-methyl-5-[[4-propyl-6-[(3r)-3-(1h-pyrrol-2-ylmethylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC=2NC=CC=2)=NC=1NC1=CC=C(C)C(C#N)=C1 NZRISDYAUFCGJF-HSZRJFAPSA-N 0.000 claims 1
• CJGPVOUIOOTEPO-OAQYLSRUSA-N 2-methyl-5-[[4-propyl-6-[(3r)-3-(propylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound C1[C@H](NCCC)CCCN1C1=CC(CCC)=NC(NC=2C=C(C(C)=CC=2)C#N)=N1 CJGPVOUIOOTEPO-OAQYLSRUSA-N 0.000 claims 1
• ORBYARYRJVHOHC-JOCHJYFZSA-N 2-methyl-5-[[4-propyl-6-[(3r)-3-(thiophen-2-ylmethylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC=2SC=CC=2)=NC=1NC1=CC=C(C)C(C#N)=C1 ORBYARYRJVHOHC-JOCHJYFZSA-N 0.000 claims 1
• NZRISDYAUFCGJF-QHCPKHFHSA-N 2-methyl-5-[[4-propyl-6-[(3s)-3-(1h-pyrrol-2-ylmethylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCC=2NC=CC=2)=NC=1NC1=CC=C(C)C(C#N)=C1 NZRISDYAUFCGJF-QHCPKHFHSA-N 0.000 claims 1
• UXQZWIZYWPFQKI-LJQANCHMSA-N 3-N-[4-[(3R)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 UXQZWIZYWPFQKI-LJQANCHMSA-N 0.000 claims 1
• HUGIIEYQKWAAJH-QGZVFWFLSA-N 3-N-[4-[(3R)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 HUGIIEYQKWAAJH-QGZVFWFLSA-N 0.000 claims 1
• PBTBOIBVYZLBAS-MRXNPFEDSA-N 3-N-[4-[(3R)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 PBTBOIBVYZLBAS-MRXNPFEDSA-N 0.000 claims 1
• OERMQHMZMZXCLV-CYBMUJFWSA-N 3-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 OERMQHMZMZXCLV-CYBMUJFWSA-N 0.000 claims 1
• DMJMWNASYODKTG-QGZVFWFLSA-N 3-N-[4-butyl-6-[(3R)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 DMJMWNASYODKTG-QGZVFWFLSA-N 0.000 claims 1
• AMKXGNBGPBHYAN-UHFFFAOYSA-N 3-[(4-piperidin-1-yl-6-propylpyrimidin-2-yl)amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=CC(C#N)=C1 AMKXGNBGPBHYAN-UHFFFAOYSA-N 0.000 claims 1
• BMGPVVBDSCRACZ-UHFFFAOYSA-N 3-[[4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=CC(C#N)=C1 BMGPVVBDSCRACZ-UHFFFAOYSA-N 0.000 claims 1
• CFESKTJZTZUODO-CYBMUJFWSA-N 3-[[4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]amino]benzamide Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=CC(C(N)=O)=C1 CFESKTJZTZUODO-CYBMUJFWSA-N 0.000 claims 1
• RRHDBHKWWMMQQK-CQSZACIVSA-N 3-[[4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=CC(C#N)=C1 RRHDBHKWWMMQQK-CQSZACIVSA-N 0.000 claims 1
• RETWOVJZNLUJTM-OAQYLSRUSA-N 3-[[4-[(3r)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC=CC(C#N)=C1 RETWOVJZNLUJTM-OAQYLSRUSA-N 0.000 claims 1
• AMYRWCPBYGYYPI-MRXNPFEDSA-N 3-[[4-[(3r)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=CC(C#N)=C1 AMYRWCPBYGYYPI-MRXNPFEDSA-N 0.000 claims 1
• LFNWSAAUTCSKGX-OAHLLOKOSA-N 3-[[4-[(3r)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=CC(C#N)=C1 LFNWSAAUTCSKGX-OAHLLOKOSA-N 0.000 claims 1
• UGLJJJPGTWDUSN-GOSISDBHSA-N 3-[[4-[(3r)-3-ethylmorpholin-4-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2[C@@H](COCC2)CC)=NC=1NC1=CC=CC(C#N)=C1 UGLJJJPGTWDUSN-GOSISDBHSA-N 0.000 claims 1
• LFNWSAAUTCSKGX-HNNXBMFYSA-N 3-[[4-[(3s)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](N)CCC2)=NC=1NC1=CC=CC(C#N)=C1 LFNWSAAUTCSKGX-HNNXBMFYSA-N 0.000 claims 1
• QNSJJHCOCNDOFN-UHFFFAOYSA-N 3-[[4-[2-(2-hydroxyethyl)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CCO)=NC=1NC1=CC=CC(C#N)=C1 QNSJJHCOCNDOFN-UHFFFAOYSA-N 0.000 claims 1
• AKPNDAKISGCITC-LJQANCHMSA-N 3-[[4-butyl-6-[(3r)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=CC(C#N)=C1 AKPNDAKISGCITC-LJQANCHMSA-N 0.000 claims 1
• MNDHHNNBXGKDRE-HXUWFJFHSA-N 3-[[4-propyl-6-[(3r)-3-(propylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound C1[C@H](NCCC)CCCN1C1=CC(CCC)=NC(NC=2C=C(C=CC=2)C#N)=N1 MNDHHNNBXGKDRE-HXUWFJFHSA-N 0.000 claims 1
• MQSQTMYQRTVSHG-CYBMUJFWSA-N 3-amino-5-[[4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC(N)=CC(C#N)=C1 MQSQTMYQRTVSHG-CYBMUJFWSA-N 0.000 claims 1
• ZXSIAWGDSSIHCP-HXUWFJFHSA-N 3-amino-5-[[4-[(3r)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC(N)=CC(C#N)=C1 ZXSIAWGDSSIHCP-HXUWFJFHSA-N 0.000 claims 1
• FFJJNKVQCAHWHA-GOSISDBHSA-N 3-amino-5-[[4-[(3r)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC(N)=CC(C#N)=C1 FFJJNKVQCAHWHA-GOSISDBHSA-N 0.000 claims 1
• DYWSKPSGYRCAMP-QGZVFWFLSA-N 3-amino-5-[[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC(N)=CC(C#N)=C1 DYWSKPSGYRCAMP-QGZVFWFLSA-N 0.000 claims 1
• SWGMDLXMFBPFGG-OAHLLOKOSA-N 3-amino-5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC(N)=CC(C#N)=C1 SWGMDLXMFBPFGG-OAHLLOKOSA-N 0.000 claims 1
• HKRVOUIRBIBROJ-CQSZACIVSA-N 3-amino-5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC(N)=CC(C#N)=C1 HKRVOUIRBIBROJ-CQSZACIVSA-N 0.000 claims 1
• WKNDSDODJWIEFT-GOSISDBHSA-N 3-amino-5-[[4-butyl-6-[(3r)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]amino]benzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC(N)=CC(C#N)=C1 WKNDSDODJWIEFT-GOSISDBHSA-N 0.000 claims 1
• MXQATHQSZXKUKP-CQSZACIVSA-N 3-n-[4-[(3r)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]-5-(trifluoromethyl)benzene-1,3-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 MXQATHQSZXKUKP-CQSZACIVSA-N 0.000 claims 1
• UJAVEHGFWKOZKL-UHFFFAOYSA-N 4-(2,5-dimethylpiperazin-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound CC1CNC(C)CN1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 UJAVEHGFWKOZKL-UHFFFAOYSA-N 0.000 claims 1
• SJBWPIRTTWGAST-UHFFFAOYSA-N 4-(2,5-dimethylpiperazin-1-yl)-n-(4-fluorophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CNC(C)C2)C)=NC=1NC1=CC=C(F)C=C1 SJBWPIRTTWGAST-UHFFFAOYSA-N 0.000 claims 1
• IUCGHLDAWTWAAM-UHFFFAOYSA-N 4-(2,6-dimethylmorpholin-4-yl)-n-(4-fluorophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CC(C)OC(C)C2)=NC=1NC1=CC=C(F)C=C1 IUCGHLDAWTWAAM-UHFFFAOYSA-N 0.000 claims 1
• HSEXQXSUEHJYRM-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-6-propyl-n-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=CC(C(F)(F)F)=C1 HSEXQXSUEHJYRM-UHFFFAOYSA-N 0.000 claims 1
• CANDSARFUDVFQI-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-n-(3-methoxyphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=CC(OC)=C1 CANDSARFUDVFQI-UHFFFAOYSA-N 0.000 claims 1
• GZJIXDIUYKYSGY-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-n-(3-methylsulfanylphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=CC(SC)=C1 GZJIXDIUYKYSGY-UHFFFAOYSA-N 0.000 claims 1
• HHBUZQBCSKIABD-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-n-(3-nitrophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=CC([N+]([O-])=O)=C1 HHBUZQBCSKIABD-UHFFFAOYSA-N 0.000 claims 1
• LZERMXSZKYQHCX-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-n-(4-fluoro-3-nitrophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=C(F)C([N+]([O-])=O)=C1 LZERMXSZKYQHCX-UHFFFAOYSA-N 0.000 claims 1
• BUTWUCZOPAVIGV-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound CCC1CCCCN1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 BUTWUCZOPAVIGV-UHFFFAOYSA-N 0.000 claims 1
• SUJAIJHQMGALFC-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-n-(4-fluorophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=C(F)C=C1 SUJAIJHQMGALFC-UHFFFAOYSA-N 0.000 claims 1
• MGSDANUXROBICJ-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-n-(5-methoxy-2-methylphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC(OC)=CC=C1C MGSDANUXROBICJ-UHFFFAOYSA-N 0.000 claims 1
• JEBYBCOQWSNEAT-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound N=1C(C)=CC(N2CC3CCCCC3CC2)=NC=1NC1=CC=C(F)C=C1 JEBYBCOQWSNEAT-UHFFFAOYSA-N 0.000 claims 1
• MDZJJLSWZZOBSN-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-6-ethyl-n-(4-fluorophenyl)pyrimidin-2-amine Chemical compound N=1C(CC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=C(F)C=C1 MDZJJLSWZZOBSN-UHFFFAOYSA-N 0.000 claims 1
• SDEVEWSYQDUBQJ-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-6-propyl-n-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=CC(C(F)(F)F)=C1 SDEVEWSYQDUBQJ-UHFFFAOYSA-N 0.000 claims 1
• VQXCNXPAMRLIQW-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(3-chloro-4-methylphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=C(C)C(Cl)=C1 VQXCNXPAMRLIQW-UHFFFAOYSA-N 0.000 claims 1
• BWFOWXWVVADZSG-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(3-chlorophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=CC(Cl)=C1 BWFOWXWVVADZSG-UHFFFAOYSA-N 0.000 claims 1
• OLABFMUOXQBAED-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(3-methoxyphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=CC(OC)=C1 OLABFMUOXQBAED-UHFFFAOYSA-N 0.000 claims 1
• CBJNQFAWAOGTDK-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(3-methylsulfanylphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=CC(SC)=C1 CBJNQFAWAOGTDK-UHFFFAOYSA-N 0.000 claims 1
• LBGYNDHRRWHRCR-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(3-nitrophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=CC([N+]([O-])=O)=C1 LBGYNDHRRWHRCR-UHFFFAOYSA-N 0.000 claims 1
• FUTFTWGWNADEPD-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(4-chloro-3-nitrophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FUTFTWGWNADEPD-UHFFFAOYSA-N 0.000 claims 1
• CGZOAIIFXDODPG-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound N=1C(C)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=C(F)C=C1 CGZOAIIFXDODPG-UHFFFAOYSA-N 0.000 claims 1
• VHJOIEWACJFRGI-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(4-methoxyphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC=C(OC)C=C1 VHJOIEWACJFRGI-UHFFFAOYSA-N 0.000 claims 1
• YGAFZNODFNIGAG-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(5-chloro-2-methylphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC(Cl)=CC=C1C YGAFZNODFNIGAG-UHFFFAOYSA-N 0.000 claims 1
• KWCJIKQVJULEOP-UHFFFAOYSA-N 4-(3,4,4a,5,6,7,8,8a-octahydro-2h-quinolin-1-yl)-n-(5-methoxy-2-methylphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCCCC3CCC2)=NC=1NC1=CC(OC)=CC=C1C KWCJIKQVJULEOP-UHFFFAOYSA-N 0.000 claims 1
• LCEPLEROBKFRFX-UHFFFAOYSA-N 4-(3,5-dimethylpiperazin-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound C1C(C)NC(C)CN1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 LCEPLEROBKFRFX-UHFFFAOYSA-N 0.000 claims 1
• DIIZDWNMVLUQHB-UHFFFAOYSA-N 4-(3,6-dihydro-2h-pyridin-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound N=1C(C)=CC(N2CC=CCC2)=NC=1NC1=CC=C(F)C=C1 DIIZDWNMVLUQHB-UHFFFAOYSA-N 0.000 claims 1
• XONLCIUTIGUCKG-UHFFFAOYSA-N 4-(3,6-dihydro-2h-pyridin-1-yl)-n-(4-fluorophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CC=CCC2)=NC=1NC1=CC=C(F)C=C1 XONLCIUTIGUCKG-UHFFFAOYSA-N 0.000 claims 1
• DNJKIRLUXSMCPL-UHFFFAOYSA-N 4-(4-ethylpiperazin-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound C1CN(CC)CCN1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 DNJKIRLUXSMCPL-UHFFFAOYSA-N 0.000 claims 1
• GIIDXWNBDWWTGM-UHFFFAOYSA-N 4-(azepan-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound N=1C(C)=CC(N2CCCCCC2)=NC=1NC1=CC=C(F)C=C1 GIIDXWNBDWWTGM-UHFFFAOYSA-N 0.000 claims 1
• AUFLKNBTJYCNTI-UHFFFAOYSA-N 4-(azepan-1-yl)-n-(4-fluorophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCCC2)=NC=1NC1=CC=C(F)C=C1 AUFLKNBTJYCNTI-UHFFFAOYSA-N 0.000 claims 1
• QWYBHQYFHSFUMF-UHFFFAOYSA-N 4-(azetidin-1-yl)-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound N=1C(C)=CC(N2CCC2)=NC=1NC1=CC=C(F)C=C1 QWYBHQYFHSFUMF-UHFFFAOYSA-N 0.000 claims 1
• CUDGWXGUBNGKLO-GFCCVEGCSA-N 4-N-[4-[(2R)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 CUDGWXGUBNGKLO-GFCCVEGCSA-N 0.000 claims 1
• KRGKPRWJWXIGKO-GFCCVEGCSA-N 4-N-[4-[(2R)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]-2-nitrobenzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 KRGKPRWJWXIGKO-GFCCVEGCSA-N 0.000 claims 1
• ZFXDXTXCUMVAMG-GOSISDBHSA-N 4-N-[4-[(3R)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 ZFXDXTXCUMVAMG-GOSISDBHSA-N 0.000 claims 1
• ZUKFHMJBXCXOJK-GOSISDBHSA-N 4-N-[4-[(3R)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-2-nitrobenzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 ZUKFHMJBXCXOJK-GOSISDBHSA-N 0.000 claims 1
• CYVOUVVPZCFSAR-MRXNPFEDSA-N 4-N-[4-[(3R)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 CYVOUVVPZCFSAR-MRXNPFEDSA-N 0.000 claims 1
• SIGVOUAJFKVQNB-MRXNPFEDSA-N 4-N-[4-[(3R)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-2-nitrobenzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 SIGVOUAJFKVQNB-MRXNPFEDSA-N 0.000 claims 1
• ZMZNDSQJZOJMNH-OAHLLOKOSA-N 4-N-[4-[(3R)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 ZMZNDSQJZOJMNH-OAHLLOKOSA-N 0.000 claims 1
• VBIHESXAHXLYHO-OAHLLOKOSA-N 4-N-[4-[(3R)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]benzene-1,2,4-triamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(N)C(N)=C1 VBIHESXAHXLYHO-OAHLLOKOSA-N 0.000 claims 1
• SXNVBZSQKSHQRT-CYBMUJFWSA-N 4-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 SXNVBZSQKSHQRT-CYBMUJFWSA-N 0.000 claims 1
• PXMHFGJMWBPHNE-CYBMUJFWSA-N 4-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]-2-nitrobenzene-1,4-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 PXMHFGJMWBPHNE-CYBMUJFWSA-N 0.000 claims 1
• SJIWGPVYXNWPSJ-CYBMUJFWSA-N 4-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]benzene-1,2,4-triamine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C(N)=C1 SJIWGPVYXNWPSJ-CYBMUJFWSA-N 0.000 claims 1
• PXFIDRRPWBYOTQ-GFCCVEGCSA-N 4-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 PXFIDRRPWBYOTQ-GFCCVEGCSA-N 0.000 claims 1
• YMKXYMHLGYRVRP-GFCCVEGCSA-N 4-N-[4-[(3R)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]-2-nitrobenzene-1,4-diamine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 YMKXYMHLGYRVRP-GFCCVEGCSA-N 0.000 claims 1
• LPBPEEYWNHZQCM-MRXNPFEDSA-N 4-N-[4-butyl-6-[(3R)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 LPBPEEYWNHZQCM-MRXNPFEDSA-N 0.000 claims 1
• NZEBUHWMUJMMTN-MRXNPFEDSA-N 4-N-[4-butyl-6-[(3R)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]-2-nitrobenzene-1,4-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 NZEBUHWMUJMMTN-MRXNPFEDSA-N 0.000 claims 1
• HVDBFFAMEYQMGF-MRXNPFEDSA-N 4-N-[4-butyl-6-[(3R)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]benzene-1,2,4-triamine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(N)C(N)=C1 HVDBFFAMEYQMGF-MRXNPFEDSA-N 0.000 claims 1
• XKSXMXDAXBZRAP-OKILXGFUSA-N 4-[(2s,6r)-2,6-dimethylpiperidin-1-yl]-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound C[C@H]1CCC[C@@H](C)N1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 XKSXMXDAXBZRAP-OKILXGFUSA-N 0.000 claims 1
• LNCKDZYVWNSWCL-QGZVFWFLSA-N 4-[(3r)-3-(methylamino)piperidin-1-yl]-n-[4-methyl-3-(trifluoromethyl)phenyl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(C(F)(F)F)=C1 LNCKDZYVWNSWCL-QGZVFWFLSA-N 0.000 claims 1
• BNKRUXRLTLCNDW-QGZVFWFLSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-(3,4-dimethylphenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(C)=C1 BNKRUXRLTLCNDW-QGZVFWFLSA-N 0.000 claims 1
• FBZDXNPRJLWRIK-OAHLLOKOSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-(3-fluoro-4-methylphenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(F)=C1 FBZDXNPRJLWRIK-OAHLLOKOSA-N 0.000 claims 1
• UCSMQDNAKCXYEA-MRXNPFEDSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-(3-methoxy-4-methylphenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(OC)=C1 UCSMQDNAKCXYEA-MRXNPFEDSA-N 0.000 claims 1
• KXKDJWDYAMREDP-CQSZACIVSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-(3-nitrophenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=CC([N+]([O-])=O)=C1 KXKDJWDYAMREDP-CQSZACIVSA-N 0.000 claims 1
• KZOSMQYGPDCVTE-CYBMUJFWSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-(4-chloro-3-nitrophenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 KZOSMQYGPDCVTE-CYBMUJFWSA-N 0.000 claims 1
• ZYXFGBLWIZXPBV-CYBMUJFWSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-(4-fluoro-3-nitrophenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(F)C([N+]([O-])=O)=C1 ZYXFGBLWIZXPBV-CYBMUJFWSA-N 0.000 claims 1
• JSQIXWHTBOENGH-OAHLLOKOSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-(4-methyl-3-nitrophenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C([N+]([O-])=O)=C1 JSQIXWHTBOENGH-OAHLLOKOSA-N 0.000 claims 1
• MDLOHZDHVXZNSL-CYBMUJFWSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-[4-fluoro-3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(F)C(C(F)(F)F)=C1 MDLOHZDHVXZNSL-CYBMUJFWSA-N 0.000 claims 1
• WPKUUGIALYYAGY-OAHLLOKOSA-N 4-[(3r)-3-aminopiperidin-1-yl]-6-butyl-n-[4-methyl-3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(C(F)(F)F)=C1 WPKUUGIALYYAGY-OAHLLOKOSA-N 0.000 claims 1
• LYVSKLMUUBSUDW-CQSZACIVSA-N 4-[(3r)-3-aminopiperidin-1-yl]-n-(3-fluoro-4-methylphenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(F)=C1 LYVSKLMUUBSUDW-CQSZACIVSA-N 0.000 claims 1
• CXOYGMXZFZTIJF-CQSZACIVSA-N 4-[(3r)-3-aminopiperidin-1-yl]-n-(4-methyl-3-nitrophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C([N+]([O-])=O)=C1 CXOYGMXZFZTIJF-CQSZACIVSA-N 0.000 claims 1
• GXJSGQBALOPVRN-CQSZACIVSA-N 4-[(3r)-3-aminopiperidin-1-yl]-n-[4-methyl-3-(trifluoromethyl)phenyl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(C(F)(F)F)=C1 GXJSGQBALOPVRN-CQSZACIVSA-N 0.000 claims 1
• VSPKZOWDEQPXGV-ZDUSSCGKSA-N 4-[(3s)-3-aminopiperidin-1-yl]-n-(3-nitrophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@@H](N)CCC2)=NC=1NC1=CC=CC([N+]([O-])=O)=C1 VSPKZOWDEQPXGV-ZDUSSCGKSA-N 0.000 claims 1
• AJVOWNOYCRCXFN-BETUJISGSA-N 4-[(3s,5r)-3,5-dimethylpiperidin-1-yl]-n-(4-fluorophenyl)-6-methylpyrimidin-2-amine Chemical compound C1[C@@H](C)C[C@@H](C)CN1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 AJVOWNOYCRCXFN-BETUJISGSA-N 0.000 claims 1
• BSJZQVHQJDCKML-UHFFFAOYSA-N 4-butyl-6-(2-ethylpiperidin-1-yl)-n-(4-fluorophenyl)pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=C(F)C=C1 BSJZQVHQJDCKML-UHFFFAOYSA-N 0.000 claims 1
• UWMHUDVNAHSQKR-GOSISDBHSA-N 4-butyl-6-[(3r)-3-(methylamino)piperidin-1-yl]-n-[4-methyl-3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(C(F)(F)F)=C1 UWMHUDVNAHSQKR-GOSISDBHSA-N 0.000 claims 1
• TYZDAGBOZJRWDW-HXUWFJFHSA-N 4-butyl-n-(3,4-dimethylphenyl)-6-[(3r)-3-(methylamino)piperidin-1-yl]pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(C)=C1 TYZDAGBOZJRWDW-HXUWFJFHSA-N 0.000 claims 1
• YRNPHNDVCYCZGO-GOSISDBHSA-N 4-butyl-n-(3-fluoro-4-methylphenyl)-6-[(3r)-3-(methylamino)piperidin-1-yl]pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(F)=C1 YRNPHNDVCYCZGO-GOSISDBHSA-N 0.000 claims 1
• LZDFYXWTGRXBBE-LJQANCHMSA-N 4-butyl-n-(3-methoxy-4-methylphenyl)-6-[(3r)-3-(methylamino)piperidin-1-yl]pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(OC)=C1 LZDFYXWTGRXBBE-LJQANCHMSA-N 0.000 claims 1
• ASNMFVQEJPGFCB-UHFFFAOYSA-N 4-butyl-n-(4-fluorophenyl)-6-morpholin-4-ylpyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2CCOCC2)=NC=1NC1=CC=C(F)C=C1 ASNMFVQEJPGFCB-UHFFFAOYSA-N 0.000 claims 1
• OIABPYLJZWQXOF-UHFFFAOYSA-N 4-butyl-n-(4-fluorophenyl)-6-piperidin-1-ylpyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2CCCCC2)=NC=1NC1=CC=C(F)C=C1 OIABPYLJZWQXOF-UHFFFAOYSA-N 0.000 claims 1
• XEZGQEPRUQTFSJ-MRXNPFEDSA-N 4-butyl-n-[4-fluoro-3-(trifluoromethyl)phenyl]-6-[(3r)-3-(methylamino)piperidin-1-yl]pyrimidin-2-amine Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(F)C(C(F)(F)F)=C1 XEZGQEPRUQTFSJ-MRXNPFEDSA-N 0.000 claims 1
• IXKVCVFJHSGMCF-OAHLLOKOSA-N 4-chloro-1-n-[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(Cl)C(N)=C1 IXKVCVFJHSGMCF-OAHLLOKOSA-N 0.000 claims 1
• IQZIFMXBOLJVEC-UHFFFAOYSA-N 4-ethyl-6-(2-ethylpiperidin-1-yl)-n-(4-fluorophenyl)pyrimidin-2-amine Chemical compound CCC1CCCCN1C1=CC(CC)=NC(NC=2C=CC(F)=CC=2)=N1 IQZIFMXBOLJVEC-UHFFFAOYSA-N 0.000 claims 1
• XQVWJRRPGSEHCQ-UHFFFAOYSA-N 4-ethyl-n-(4-fluorophenyl)-6-morpholin-4-ylpyrimidin-2-amine Chemical compound N=1C(CC)=CC(N2CCOCC2)=NC=1NC1=CC=C(F)C=C1 XQVWJRRPGSEHCQ-UHFFFAOYSA-N 0.000 claims 1
• OCJRLJUDEYCFFR-UHFFFAOYSA-N 4-ethyl-n-(4-fluorophenyl)-6-piperidin-1-ylpyrimidin-2-amine Chemical compound N=1C(CC)=CC(N2CCCCC2)=NC=1NC1=CC=C(F)C=C1 OCJRLJUDEYCFFR-UHFFFAOYSA-N 0.000 claims 1
• JQLQQQZLPNQQNK-GFCCVEGCSA-N 4-fluoro-1-n-[4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-yl]benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(F)C(N)=C1 JQLQQQZLPNQQNK-GFCCVEGCSA-N 0.000 claims 1
• CIAXEGAYZMKBEK-OAHLLOKOSA-N 4-fluoro-1-n-[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(F)C(N)=C1 CIAXEGAYZMKBEK-OAHLLOKOSA-N 0.000 claims 1
• QQKIOHYYTWCJTA-MRXNPFEDSA-N 4-methoxy-1-n-[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(OC)C(N)=C1 QQKIOHYYTWCJTA-MRXNPFEDSA-N 0.000 claims 1
• OOHJNQMMOJXDCN-QGZVFWFLSA-N 4-methyl-1-n-[4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]benzene-1,3-diamine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(N)=C1 OOHJNQMMOJXDCN-QGZVFWFLSA-N 0.000 claims 1
• CRRGDDQXWVDWQD-UHFFFAOYSA-N 4-morpholin-4-yl-6-propyl-n-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=CC(C(F)(F)F)=C1 CRRGDDQXWVDWQD-UHFFFAOYSA-N 0.000 claims 1
• CGILNTIUMLHFJS-UHFFFAOYSA-N 4-morpholin-4-yl-n-(3-nitrophenyl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=CC([N+]([O-])=O)=C1 CGILNTIUMLHFJS-UHFFFAOYSA-N 0.000 claims 1
• BGGRCVFQLYDNJZ-OAHLLOKOSA-N 4-n-[4-[(3r)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]benzene-1,4-diamine Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(N)C=C1 BGGRCVFQLYDNJZ-OAHLLOKOSA-N 0.000 claims 1
• BERLBTSAEZWZQB-UHFFFAOYSA-N 4-piperidin-1-yl-6-propyl-n-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=CC(C(F)(F)F)=C1 BERLBTSAEZWZQB-UHFFFAOYSA-N 0.000 claims 1
• ZSQYMJMRKQITCD-JOCHJYFZSA-N 5-[[4-[(3r)-3-(2,2-dimethylpropylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC(C)(C)C)=NC=1NC1=CC=C(C)C(C#N)=C1 ZSQYMJMRKQITCD-JOCHJYFZSA-N 0.000 claims 1
• VTDLCIODLRQPIM-JOCHJYFZSA-N 5-[[4-[(3r)-3-(butylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound C1[C@H](NCCCC)CCCN1C1=CC(CCC)=NC(NC=2C=C(C(C)=CC=2)C#N)=N1 VTDLCIODLRQPIM-JOCHJYFZSA-N 0.000 claims 1
• XLDVWUZRQVAQOQ-XMMPIXPASA-N 5-[[4-[(3r)-3-(cyclopentylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CCCC2)=NC=1NC1=CC=C(C)C(C#N)=C1 XLDVWUZRQVAQOQ-XMMPIXPASA-N 0.000 claims 1
• IRNIIHHJQWGTFC-HXUWFJFHSA-N 5-[[4-[(3r)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-fluorobenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC=C(F)C(C#N)=C1 IRNIIHHJQWGTFC-HXUWFJFHSA-N 0.000 claims 1
• WRQZFFIWHRECQO-JOCHJYFZSA-N 5-[[4-[(3r)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC2CC2)=NC=1NC1=CC=C(C)C(C#N)=C1 WRQZFFIWHRECQO-JOCHJYFZSA-N 0.000 claims 1
• KANYNTUJPBULNG-HXUWFJFHSA-N 5-[[4-[(3r)-3-(diethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-fluorobenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)N(CC)CC)=NC=1NC1=CC=C(F)C(C#N)=C1 KANYNTUJPBULNG-HXUWFJFHSA-N 0.000 claims 1
• YCDVTXGXHPIXAM-JOCHJYFZSA-N 5-[[4-[(3r)-3-(diethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)N(CC)CC)=NC=1NC1=CC=C(C)C(C#N)=C1 YCDVTXGXHPIXAM-JOCHJYFZSA-N 0.000 claims 1
• PEVLOJWJKLICQB-GOSISDBHSA-N 5-[[4-[(3r)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-fluorobenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC=C(F)C(C#N)=C1 PEVLOJWJKLICQB-GOSISDBHSA-N 0.000 claims 1
• AZZYBKJMCBUAEG-XMMPIXPASA-N 5-[[4-[(3r)-3-[(4-hydroxyphenyl)methylamino]piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NCC=2C=CC(O)=CC=2)=NC=1NC1=CC=C(C)C(C#N)=C1 AZZYBKJMCBUAEG-XMMPIXPASA-N 0.000 claims 1
• GWCCFFIKAIQPCZ-AREMUKBSSA-N 5-[[4-[(3r)-3-[bis(cyclopropylmethyl)amino]piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)N(CC2CC2)CC2CC2)=NC=1NC1=CC=C(C)C(C#N)=C1 GWCCFFIKAIQPCZ-AREMUKBSSA-N 0.000 claims 1
• XQHRCNSDPNTART-OAHLLOKOSA-N 5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]amino]-2-fluorobenzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(F)C(C#N)=C1 XQHRCNSDPNTART-OAHLLOKOSA-N 0.000 claims 1
• YBADPVPBXDYOQZ-QGZVFWFLSA-N 5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-butylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(C#N)=C1 YBADPVPBXDYOQZ-QGZVFWFLSA-N 0.000 claims 1
• HPWFBIVUWQXQMV-CQSZACIVSA-N 5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-fluorobenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(F)C(C#N)=C1 HPWFBIVUWQXQMV-CQSZACIVSA-N 0.000 claims 1
• QKRCOVFIRVDSPH-MRXNPFEDSA-N 5-[[4-[(3r)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](N)CCC2)=NC=1NC1=CC=C(C)C(C#N)=C1 QKRCOVFIRVDSPH-MRXNPFEDSA-N 0.000 claims 1
• WRQZFFIWHRECQO-QFIPXVFZSA-N 5-[[4-[(3s)-3-(cyclopropylmethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCC2CC2)=NC=1NC1=CC=C(C)C(C#N)=C1 WRQZFFIWHRECQO-QFIPXVFZSA-N 0.000 claims 1
• YCDVTXGXHPIXAM-QFIPXVFZSA-N 5-[[4-[(3s)-3-(diethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)N(CC)CC)=NC=1NC1=CC=C(C)C(C#N)=C1 YCDVTXGXHPIXAM-QFIPXVFZSA-N 0.000 claims 1
• DJSXNTNWFPQMLV-FQEVSTJZSA-N 5-[[4-[(3s)-3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCC)=NC=1NC1=CC=C(C)C(C#N)=C1 DJSXNTNWFPQMLV-FQEVSTJZSA-N 0.000 claims 1
• HCTVEBRHAUTJDB-DEOSSOPVSA-N 5-[[4-[(3s)-3-[(4,5-dimethylfuran-2-yl)methylamino]piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)NCC=2OC(C)=C(C)C=2)=NC=1NC1=CC=C(C)C(C#N)=C1 HCTVEBRHAUTJDB-DEOSSOPVSA-N 0.000 claims 1
• GWCCFFIKAIQPCZ-SANMLTNESA-N 5-[[4-[(3s)-3-[bis(cyclopropylmethyl)amino]piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@H](CCC2)N(CC2CC2)CC2CC2)=NC=1NC1=CC=C(C)C(C#N)=C1 GWCCFFIKAIQPCZ-SANMLTNESA-N 0.000 claims 1
• QKRCOVFIRVDSPH-INIZCTEOSA-N 5-[[4-[(3s)-3-aminopiperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2C[C@@H](N)CCC2)=NC=1NC1=CC=C(C)C(C#N)=C1 QKRCOVFIRVDSPH-INIZCTEOSA-N 0.000 claims 1
• DJSXNTNWFPQMLV-UHFFFAOYSA-N 5-[[4-[3-(ethylamino)piperidin-1-yl]-6-propylpyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCC)=CC(N2CC(CCC2)NCC)=NC=1NC1=CC=C(C)C(C#N)=C1 DJSXNTNWFPQMLV-UHFFFAOYSA-N 0.000 claims 1
• LGKWFCPKNIXLEC-HSZRJFAPSA-N 5-[[4-butyl-6-[(3r)-3-(butylamino)piperidin-1-yl]pyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound C1[C@H](NCCCC)CCCN1C1=CC(CCCC)=NC(NC=2C=C(C(C)=CC=2)C#N)=N1 LGKWFCPKNIXLEC-HSZRJFAPSA-N 0.000 claims 1
• WCCJOYVJCAFXDZ-OAQYLSRUSA-N 5-[[4-butyl-6-[(3r)-3-(ethylamino)piperidin-1-yl]pyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NCC)=NC=1NC1=CC=C(C)C(C#N)=C1 WCCJOYVJCAFXDZ-OAQYLSRUSA-N 0.000 claims 1
• PIRYVWRLFJHIGC-HXUWFJFHSA-N 5-[[4-butyl-6-[(3r)-3-(methylamino)piperidin-1-yl]pyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(C#N)=C1 PIRYVWRLFJHIGC-HXUWFJFHSA-N 0.000 claims 1
• IRSONHVNJDDICP-XMMPIXPASA-N 5-[[4-butyl-6-[(3r)-3-(pentylamino)piperidin-1-yl]pyrimidin-2-yl]amino]-2-methylbenzonitrile Chemical compound C1[C@H](NCCCCC)CCCN1C1=CC(CCCC)=NC(NC=2C=C(C(C)=CC=2)C#N)=N1 IRSONHVNJDDICP-XMMPIXPASA-N 0.000 claims 1
• SXYFHMFSDRTCQO-UHFFFAOYSA-N 8-[2-(4-fluoroanilino)-6-propylpyrimidin-4-yl]-8-azabicyclo[3.2.1]octan-3-ol Chemical compound N=1C(CCC)=CC(N2C3CCC2CC(O)C3)=NC=1NC1=CC=C(F)C=C1 SXYFHMFSDRTCQO-UHFFFAOYSA-N 0.000 claims 1
• QHRFKMRAUPAZNF-UHFFFAOYSA-N [1-[2-(4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidin-4-yl]methanol Chemical compound N=1C(CCC)=CC(N2CCC(CO)CC2)=NC=1NC1=CC=C(F)C=C1 QHRFKMRAUPAZNF-UHFFFAOYSA-N 0.000 claims 1
• GFRTUTWSTNCEKA-UHFFFAOYSA-N ethyl 1-[2-(4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidine-2-carboxylate Chemical compound N=1C(CCC)=CC(N2C(CCCC2)C(=O)OCC)=NC=1NC1=CC=C(F)C=C1 GFRTUTWSTNCEKA-UHFFFAOYSA-N 0.000 claims 1
• PXVOKRDOLSCMBJ-LJQANCHMSA-N n-(3,4-dimethylphenyl)-4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(C)=C1 PXVOKRDOLSCMBJ-LJQANCHMSA-N 0.000 claims 1
• JZGGPRLYKHTWNL-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=C(C)C(Cl)=C1 JZGGPRLYKHTWNL-UHFFFAOYSA-N 0.000 claims 1
• IQTNEWTZQKTNOB-UHFFFAOYSA-N n-(3-chloro-4-methylphenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=C(C)C(Cl)=C1 IQTNEWTZQKTNOB-UHFFFAOYSA-N 0.000 claims 1
• YFHYQIKACRIDJQ-UHFFFAOYSA-N n-(3-chlorophenyl)-4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=CC(Cl)=C1 YFHYQIKACRIDJQ-UHFFFAOYSA-N 0.000 claims 1
• GJGNGPPLESEULP-UHFFFAOYSA-N n-(3-chlorophenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=CC(Cl)=C1 GJGNGPPLESEULP-UHFFFAOYSA-N 0.000 claims 1
• VCZYSKNCHQLMNG-UHFFFAOYSA-N n-(3-chlorophenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=CC(Cl)=C1 VCZYSKNCHQLMNG-UHFFFAOYSA-N 0.000 claims 1
• LWPMETAIWYNJBP-QGZVFWFLSA-N n-(3-fluoro-4-methylphenyl)-4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(F)=C1 LWPMETAIWYNJBP-QGZVFWFLSA-N 0.000 claims 1
• LPHPILWHPCRLKK-GOSISDBHSA-N n-(3-methoxy-4-methylphenyl)-4-[(3r)-3-(methylamino)piperidin-1-yl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC)=NC=1NC1=CC=C(C)C(OC)=C1 LPHPILWHPCRLKK-GOSISDBHSA-N 0.000 claims 1
• XWUYQGHWMBGKOL-UHFFFAOYSA-N n-(3-methoxyphenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=CC(OC)=C1 XWUYQGHWMBGKOL-UHFFFAOYSA-N 0.000 claims 1
• ABPANJGFJNGLRX-UHFFFAOYSA-N n-(3-methoxyphenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=CC(OC)=C1 ABPANJGFJNGLRX-UHFFFAOYSA-N 0.000 claims 1
• YQCHGHUWHPRLTR-UHFFFAOYSA-N n-(3-methylsulfanylphenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=CC(SC)=C1 YQCHGHUWHPRLTR-UHFFFAOYSA-N 0.000 claims 1
• XDGDGLFKHFSKSV-UHFFFAOYSA-N n-(3-methylsulfanylphenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=CC(SC)=C1 XDGDGLFKHFSKSV-UHFFFAOYSA-N 0.000 claims 1
• YNDYNFFCXGEMGZ-UHFFFAOYSA-N n-(3-nitrophenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=CC([N+]([O-])=O)=C1 YNDYNFFCXGEMGZ-UHFFFAOYSA-N 0.000 claims 1
• PDOHMSRYMYDQCP-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)-4-(2-ethylpiperidin-1-yl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)CC)=NC=1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 PDOHMSRYMYDQCP-UHFFFAOYSA-N 0.000 claims 1
• VALQAJVSLAWDGB-GFCCVEGCSA-N n-(4-chloro-3-nitrophenyl)-4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 VALQAJVSLAWDGB-GFCCVEGCSA-N 0.000 claims 1
• BPGKNBDMUQAFPE-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 BPGKNBDMUQAFPE-UHFFFAOYSA-N 0.000 claims 1
• FZHLLVYAKCKPMI-UHFFFAOYSA-N n-(4-chloro-3-nitrophenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FZHLLVYAKCKPMI-UHFFFAOYSA-N 0.000 claims 1
• QLCWYRZQZFSGMJ-GFCCVEGCSA-N n-(4-fluoro-3-nitrophenyl)-4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(F)C([N+]([O-])=O)=C1 QLCWYRZQZFSGMJ-GFCCVEGCSA-N 0.000 claims 1
• AMBUSYUBZOZESA-UHFFFAOYSA-N n-(4-fluoro-3-nitrophenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=C(F)C([N+]([O-])=O)=C1 AMBUSYUBZOZESA-UHFFFAOYSA-N 0.000 claims 1
• SXOACNWVJNCSSE-UHFFFAOYSA-N n-(4-fluoro-3-nitrophenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=C(F)C([N+]([O-])=O)=C1 SXOACNWVJNCSSE-UHFFFAOYSA-N 0.000 claims 1
• DYBYFZVTOHWVFY-UHFFFAOYSA-N n-(4-fluorophenyl)-4-(2-methylpiperidin-1-yl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C(CCCC2)C)=NC=1NC1=CC=C(F)C=C1 DYBYFZVTOHWVFY-UHFFFAOYSA-N 0.000 claims 1
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• KZCVDUQFVAFWBK-UHFFFAOYSA-N n-(4-fluorophenyl)-4-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2C3CCC2COC3)=NC=1NC1=CC=C(F)C=C1 KZCVDUQFVAFWBK-UHFFFAOYSA-N 0.000 claims 1
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• QJXZVPVGYGBGTJ-UHFFFAOYSA-N n-(4-fluorophenyl)-4-(4-phenylpiperidin-1-yl)-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCC(CC2)C=2C=CC=CC=2)=NC=1NC1=CC=C(F)C=C1 QJXZVPVGYGBGTJ-UHFFFAOYSA-N 0.000 claims 1
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• ISVKCYWVPTWBGZ-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methyl-6-(3-methylpiperidin-1-yl)pyrimidin-2-amine Chemical compound C1C(C)CCCN1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 ISVKCYWVPTWBGZ-UHFFFAOYSA-N 0.000 claims 1
• IQUUCLRDJAQTEW-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methyl-6-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC(C)=NC(NC=2C=CC(F)=CC=2)=N1 IQUUCLRDJAQTEW-UHFFFAOYSA-N 0.000 claims 1
• JJXXUECVAIRVHN-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methyl-6-(4-phenylpiperidin-1-yl)pyrimidin-2-amine Chemical compound N=1C(C)=CC(N2CCC(CC2)C=2C=CC=CC=2)=NC=1NC1=CC=C(F)C=C1 JJXXUECVAIRVHN-UHFFFAOYSA-N 0.000 claims 1
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• YYSOSBXROQYPGW-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methyl-6-piperazin-1-ylpyrimidin-2-amine Chemical compound N=1C(C)=CC(N2CCNCC2)=NC=1NC1=CC=C(F)C=C1 YYSOSBXROQYPGW-UHFFFAOYSA-N 0.000 claims 1
• NTYRDCMPKIGLNF-UHFFFAOYSA-N n-(4-fluorophenyl)-4-methyl-6-piperidin-1-ylpyrimidin-2-amine Chemical compound N=1C(C)=CC(N2CCCCC2)=NC=1NC1=CC=C(F)C=C1 NTYRDCMPKIGLNF-UHFFFAOYSA-N 0.000 claims 1
• WSSJYKKENJHHEP-UHFFFAOYSA-N n-(4-fluorophenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=C(F)C=C1 WSSJYKKENJHHEP-UHFFFAOYSA-N 0.000 claims 1
• PFZFQVZBVMSIPR-UHFFFAOYSA-N n-(4-fluorophenyl)-4-piperazin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCNCC2)=NC=1NC1=CC=C(F)C=C1 PFZFQVZBVMSIPR-UHFFFAOYSA-N 0.000 claims 1
• LJLOPSQPKOWZID-UHFFFAOYSA-N n-(4-fluorophenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=C(F)C=C1 LJLOPSQPKOWZID-UHFFFAOYSA-N 0.000 claims 1
• VGZLQEVVFYYRHO-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC=C(OC)C=C1 VGZLQEVVFYYRHO-UHFFFAOYSA-N 0.000 claims 1
• JXGLRNQBJOXNIE-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=C(OC)C=C1 JXGLRNQBJOXNIE-UHFFFAOYSA-N 0.000 claims 1
• SRSRZKUVMCXKSF-CQSZACIVSA-N n-(4-methyl-3-nitrophenyl)-4-[(2r)-2-methylpiperazin-1-yl]-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2[C@@H](CNCC2)C)=NC=1NC1=CC=C(C)C([N+]([O-])=O)=C1 SRSRZKUVMCXKSF-CQSZACIVSA-N 0.000 claims 1
• WYPAPLXXWGJUBN-UHFFFAOYSA-N n-(4-methyl-3-nitrophenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC=C(C)C([N+]([O-])=O)=C1 WYPAPLXXWGJUBN-UHFFFAOYSA-N 0.000 claims 1
• RXOGAPBBYWPNCU-UHFFFAOYSA-N n-(4-morpholin-4-yl-6-propylpyrimidin-2-yl)-1h-indol-5-amine Chemical compound N=1C(NC=2C=C3C=CNC3=CC=2)=NC(CCC)=CC=1N1CCOCC1 RXOGAPBBYWPNCU-UHFFFAOYSA-N 0.000 claims 1
• ILBULJWWNCLUDY-UHFFFAOYSA-N n-(4-morpholin-4-yl-6-propylpyrimidin-2-yl)-1h-indol-6-amine Chemical compound N=1C(NC=2C=C3NC=CC3=CC=2)=NC(CCC)=CC=1N1CCOCC1 ILBULJWWNCLUDY-UHFFFAOYSA-N 0.000 claims 1
• WELLDQJAJOMWDT-UHFFFAOYSA-N n-(4-morpholin-4-yl-6-propylpyrimidin-2-yl)-2-(trifluoromethyl)-3h-benzimidazol-5-amine Chemical compound N=1C(NC=2C=C3NC(=NC3=CC=2)C(F)(F)F)=NC(CCC)=CC=1N1CCOCC1 WELLDQJAJOMWDT-UHFFFAOYSA-N 0.000 claims 1
• YYJKIQAOQINACH-UHFFFAOYSA-N n-(4-piperidin-1-yl-6-propylpyrimidin-2-yl)-1h-indol-5-amine Chemical compound N=1C(NC=2C=C3C=CNC3=CC=2)=NC(CCC)=CC=1N1CCCCC1 YYJKIQAOQINACH-UHFFFAOYSA-N 0.000 claims 1
• WZPLUZCCBIFWGO-UHFFFAOYSA-N n-(4-piperidin-1-yl-6-propylpyrimidin-2-yl)-1h-indol-6-amine Chemical compound N=1C(NC=2C=C3NC=CC3=CC=2)=NC(CCC)=CC=1N1CCCCC1 WZPLUZCCBIFWGO-UHFFFAOYSA-N 0.000 claims 1
• MHOFIRQGVQCRSY-UHFFFAOYSA-N n-(4-piperidin-1-yl-6-propylpyrimidin-2-yl)-2-(trifluoromethyl)-3h-benzimidazol-5-amine Chemical compound N=1C(NC=2C=C3N=C(NC3=CC=2)C(F)(F)F)=NC(CCC)=CC=1N1CCCCC1 MHOFIRQGVQCRSY-UHFFFAOYSA-N 0.000 claims 1
• RZQCTDJMWCSRNU-UHFFFAOYSA-N n-(4-piperidin-1-yl-6-propylpyrimidin-2-yl)quinolin-6-amine Chemical compound N=1C(NC=2C=C3C=CC=NC3=CC=2)=NC(CCC)=CC=1N1CCCCC1 RZQCTDJMWCSRNU-UHFFFAOYSA-N 0.000 claims 1
• SBKYFNGLEBKMHR-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC(Cl)=CC=C1C SBKYFNGLEBKMHR-UHFFFAOYSA-N 0.000 claims 1
• ZLNFIVYAQNEVLM-UHFFFAOYSA-N n-(5-chloro-2-methylphenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC(Cl)=CC=C1C ZLNFIVYAQNEVLM-UHFFFAOYSA-N 0.000 claims 1
• CAXSMDXECQDBPL-UHFFFAOYSA-N n-(5-methoxy-2-methylphenyl)-4-morpholin-4-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCOCC2)=NC=1NC1=CC(OC)=CC=C1C CAXSMDXECQDBPL-UHFFFAOYSA-N 0.000 claims 1
• ZPIXTIYUGVQFNK-UHFFFAOYSA-N n-(5-methoxy-2-methylphenyl)-4-piperidin-1-yl-6-propylpyrimidin-2-amine Chemical compound N=1C(CCC)=CC(N2CCCCC2)=NC=1NC1=CC(OC)=CC=C1C ZPIXTIYUGVQFNK-UHFFFAOYSA-N 0.000 claims 1
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• JCIUYNSXJLYOPG-OAHLLOKOSA-N n-[(3r)-1-[2-(3-amino-4-chloroanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(Cl)C(N)=C1 JCIUYNSXJLYOPG-OAHLLOKOSA-N 0.000 claims 1
• DFEWPTBUXAXIPY-QGZVFWFLSA-N n-[(3r)-1-[2-(3-amino-4-fluoroanilino)-6-butylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(F)C(N)=C1 DFEWPTBUXAXIPY-QGZVFWFLSA-N 0.000 claims 1
• HLPVCWIEWAPSSL-OAHLLOKOSA-N n-[(3r)-1-[2-(3-amino-4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(F)C(N)=C1 HLPVCWIEWAPSSL-OAHLLOKOSA-N 0.000 claims 1
• UCMSWOPNQUIILY-QGZVFWFLSA-N n-[(3r)-1-[2-(3-amino-4-methylanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(C)C(N)=C1 UCMSWOPNQUIILY-QGZVFWFLSA-N 0.000 claims 1
• RMPHNSZRRBIRKQ-LJQANCHMSA-N n-[(3r)-1-[2-(3-amino-5-cyanoanilino)-6-butylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC(N)=CC(C#N)=C1 RMPHNSZRRBIRKQ-LJQANCHMSA-N 0.000 claims 1
• RFYPZIOHWLIDPN-QGZVFWFLSA-N n-[(3r)-1-[2-(3-amino-5-cyanoanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC(N)=CC(C#N)=C1 RFYPZIOHWLIDPN-QGZVFWFLSA-N 0.000 claims 1
• IBBXWOJYXBJLIZ-GOSISDBHSA-N n-[(3r)-1-[2-(3-amino-5-cyanoanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC(N)=CC(C#N)=C1 IBBXWOJYXBJLIZ-GOSISDBHSA-N 0.000 claims 1
• VHRPLYHAWICUKY-QGZVFWFLSA-N n-[(3r)-1-[2-(3-chloro-4-methylanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(C)C(Cl)=C1 VHRPLYHAWICUKY-QGZVFWFLSA-N 0.000 claims 1
• UPIJGSRWGDJXNY-QGZVFWFLSA-N n-[(3r)-1-[2-(3-cyano-4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(F)C(C#N)=C1 UPIJGSRWGDJXNY-QGZVFWFLSA-N 0.000 claims 1
• UDNNKBPZIZBIKL-GOSISDBHSA-N n-[(3r)-1-[2-(3-cyano-4-fluoroanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(F)C(C#N)=C1 UDNNKBPZIZBIKL-GOSISDBHSA-N 0.000 claims 1
• HLKMYONXBGTFCI-LJQANCHMSA-N n-[(3r)-1-[2-(3-cyano-4-methylanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(C)C(C#N)=C1 HLKMYONXBGTFCI-LJQANCHMSA-N 0.000 claims 1
• GUXZRBCATZAVRR-HXUWFJFHSA-N n-[(3r)-1-[2-(3-cyano-4-methylanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(C)C(C#N)=C1 GUXZRBCATZAVRR-HXUWFJFHSA-N 0.000 claims 1
• IECPUVBFIBJIAH-GOSISDBHSA-N n-[(3r)-1-[2-(3-cyanoanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=CC(C#N)=C1 IECPUVBFIBJIAH-GOSISDBHSA-N 0.000 claims 1
• OGJQGXBTZPYIHN-LJQANCHMSA-N n-[(3r)-1-[2-(3-cyanoanilino)-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=CC(C#N)=C1 OGJQGXBTZPYIHN-LJQANCHMSA-N 0.000 claims 1
• ISKDOERNYOFWFH-LJQANCHMSA-N n-[(3r)-1-[2-(4-amino-3-cyanoanilino)-6-butylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(N)C(C#N)=C1 ISKDOERNYOFWFH-LJQANCHMSA-N 0.000 claims 1
• LOYIBBBEEYHDJS-QGZVFWFLSA-N n-[(3r)-1-[2-(4-amino-3-nitroanilino)-6-butylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(N)C([N+]([O-])=O)=C1 LOYIBBBEEYHDJS-QGZVFWFLSA-N 0.000 claims 1
• IUMIATLGMQFZNC-GOSISDBHSA-N n-[(3r)-1-[2-[3-amino-5-(trifluoromethyl)anilino]-6-butylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 IUMIATLGMQFZNC-GOSISDBHSA-N 0.000 claims 1
• UIUUTJKRMBSDJA-MRXNPFEDSA-N n-[(3r)-1-[2-[3-amino-5-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 UIUUTJKRMBSDJA-MRXNPFEDSA-N 0.000 claims 1
• VPEWHPNGCRMSPA-QGZVFWFLSA-N n-[(3r)-1-[2-[3-amino-5-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC(N)=CC(C(F)(F)F)=C1 VPEWHPNGCRMSPA-QGZVFWFLSA-N 0.000 claims 1
• WQSWMKLTWORPGT-QGZVFWFLSA-N n-[(3r)-1-[2-[4-amino-3-(trifluoromethyl)anilino]-6-butylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 WQSWMKLTWORPGT-QGZVFWFLSA-N 0.000 claims 1
• ACBWJPORSVGXAT-OAHLLOKOSA-N n-[(3r)-1-[2-[4-amino-3-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 ACBWJPORSVGXAT-OAHLLOKOSA-N 0.000 claims 1
• RBLVBDHGUQWYSM-MRXNPFEDSA-N n-[(3r)-1-[2-[4-amino-3-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(N)C(C(F)(F)F)=C1 RBLVBDHGUQWYSM-MRXNPFEDSA-N 0.000 claims 1
• OWUCLTCVSZJHAS-OAHLLOKOSA-N n-[(3r)-1-[2-[4-fluoro-3-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-3-yl]-2-hydroxyacetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(=O)CO)=NC=1NC1=CC=C(F)C(C(F)(F)F)=C1 OWUCLTCVSZJHAS-OAHLLOKOSA-N 0.000 claims 1
• JPZILBXSKGXKPK-MRXNPFEDSA-N n-[(3r)-1-[2-[4-fluoro-3-(trifluoromethyl)anilino]-6-propylpyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(F)C(C(F)(F)F)=C1 JPZILBXSKGXKPK-MRXNPFEDSA-N 0.000 claims 1
• IQGTVLOYJIDAQG-LJQANCHMSA-N n-[(3r)-1-[6-butyl-2-(3-cyano-4-fluoroanilino)pyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(F)C(C#N)=C1 IQGTVLOYJIDAQG-LJQANCHMSA-N 0.000 claims 1
• NMQJLXBSBUNKKR-OAQYLSRUSA-N n-[(3r)-1-[6-butyl-2-(3-cyano-4-methylanilino)pyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=C(C)C(C#N)=C1 NMQJLXBSBUNKKR-OAQYLSRUSA-N 0.000 claims 1
• GXUNVEFGZZDYGE-HXUWFJFHSA-N n-[(3r)-1-[6-butyl-2-(3-cyanoanilino)pyrimidin-4-yl]piperidin-3-yl]acetamide Chemical compound N=1C(CCCC)=CC(N2C[C@@H](CCC2)NC(C)=O)=NC=1NC1=CC=CC(C#N)=C1 GXUNVEFGZZDYGE-HXUWFJFHSA-N 0.000 claims 1
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