JP2011524363A5

JP2011524363A5 -

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Publication number: JP2011524363A5
Authority: JP; Japan
Prior art keywords: amine; methylamino; pyrimidin; pyrrolidin; pyridin
Prior art date: 2009-06-11
Legal status : Granted

Application number

JP2011513686A

Other languages

English (en)

Japanese (ja)

Other versions

JP5658662B2 (ja

JP2011524363A (ja

Filing date

2009-06-11

Publication date

2012-07-26

2009-06-11 Application filed filed Critical

2009-06-11 Priority claimed from PCT/US2009/047033 external-priority patent/WO2009152325A1/en

2011-09-01 Publication of JP2011524363A publication Critical patent/JP2011524363A/ja

2012-07-26 Publication of JP2011524363A5 publication Critical patent/JP2011524363A5/ja

2015-01-28 Application granted granted Critical

2015-01-28 Publication of JP5658662B2 publication Critical patent/JP5658662B2/ja

Status Expired - Fee Related legal-status Critical Current

2029-06-11 Anticipated expiration legal-status Critical

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239000000126 substance Substances 0.000 claims 39
-1 4,4,4-trifluorobutyl Chemical group 0.000 claims 35
125000000217 alkyl group Chemical group 0.000 claims 16
125000000753 cycloalkyl group Chemical group 0.000 claims 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
125000001475 halogen functional group Chemical group 0.000 claims 8
229910052757 nitrogen Inorganic materials 0.000 claims 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
150000001875 compounds Chemical class 0.000 claims 6
238000004132 cross linking Methods 0.000 claims 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
125000003118 aryl group Chemical group 0.000 claims 4
229910052799 carbon Inorganic materials 0.000 claims 4
125000001072 heteroaryl group Chemical group 0.000 claims 4
229910052739 hydrogen Inorganic materials 0.000 claims 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 4
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims 4
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
229910052760 oxygen Inorganic materials 0.000 claims 4
239000008194 pharmaceutical composition Substances 0.000 claims 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
239000000651 prodrug Substances 0.000 claims 4
229940002612 prodrug Drugs 0.000 claims 4
125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 4
150000003839 salts Chemical class 0.000 claims 4
229910052717 sulfur Inorganic materials 0.000 claims 4
150000001412 amines Chemical class 0.000 claims 3
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 3
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
125000000134 2-(methylsulfanyl)ethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])[*] 0.000 claims 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
LMGMAZHTWLCFFM-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C1CC2CC1CC2NC(N=1)=NC=CC=1N1CCNCC1 LMGMAZHTWLCFFM-UHFFFAOYSA-N 0.000 claims 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
125000001424 substituent group Chemical group 0.000 claims 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
ADENFEYDTBAHFL-UHFFFAOYSA-N 1-[2-(4-aminobutyl)pyrimidin-4-yl]azetidin-3-amine Chemical compound NCCCCC1=NC=CC(N2CC(N)C2)=N1 ADENFEYDTBAHFL-UHFFFAOYSA-N 0.000 claims 1
HLUMDVKTRUIFPO-SNVBAGLBSA-N 1-[[4-[(3r)-3-aminopyrrolidin-1-yl]pyridin-2-yl]amino]-2-methylpropan-2-ol Chemical compound C1=NC(NCC(C)(O)C)=CC(N2C[C@H](N)CC2)=C1 HLUMDVKTRUIFPO-SNVBAGLBSA-N 0.000 claims 1
AKTIOUSKFDNOMX-SECBINFHSA-N 1-[[4-[(3r)-3-aminopyrrolidin-1-yl]pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound CC(C)(O)CNC1=NC=CC(N2C[C@H](N)CC2)=N1 AKTIOUSKFDNOMX-SECBINFHSA-N 0.000 claims 1
HLUMDVKTRUIFPO-JTQLQIEISA-N 1-[[4-[(3s)-3-aminopyrrolidin-1-yl]pyridin-2-yl]amino]-2-methylpropan-2-ol Chemical compound C1=NC(NCC(C)(O)C)=CC(N2C[C@@H](N)CC2)=C1 HLUMDVKTRUIFPO-JTQLQIEISA-N 0.000 claims 1
AKTIOUSKFDNOMX-VIFPVBQESA-N 1-[[4-[(3s)-3-aminopyrrolidin-1-yl]pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound CC(C)(O)CNC1=NC=CC(N2C[C@@H](N)CC2)=N1 AKTIOUSKFDNOMX-VIFPVBQESA-N 0.000 claims 1
CWMZUGCCHMXVOI-UHFFFAOYSA-N 2,2-dimethyl-3-[(4-piperazin-1-ylpyrimidin-2-yl)amino]propan-1-ol Chemical compound OCC(C)(C)CNC1=NC=CC(N2CCNCC2)=N1 CWMZUGCCHMXVOI-UHFFFAOYSA-N 0.000 claims 1
AHJGCFQAFIRCHN-UHFFFAOYSA-N 2,2-dimethyl-3-[(5-piperazin-1-ylpyridazin-3-yl)amino]propan-1-ol Chemical compound N1=NC(NCC(C)(CO)C)=CC(N2CCNCC2)=C1 AHJGCFQAFIRCHN-UHFFFAOYSA-N 0.000 claims 1
CLFVQEVOUZJKSP-LLVKDONJSA-N 2,2-dimethyl-3-[[4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC(C)(C)CO)=N1 CLFVQEVOUZJKSP-LLVKDONJSA-N 0.000 claims 1
CLFVQEVOUZJKSP-NSHDSACASA-N 2,2-dimethyl-3-[[4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC(C)(C)CO)=N1 CLFVQEVOUZJKSP-NSHDSACASA-N 0.000 claims 1
FTBIRQIQCHNUTJ-UHFFFAOYSA-N 2,2-dimethyl-3-[[4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1C(NC)CN1C1=CC=NC(NCC(C)(C)CO)=N1 FTBIRQIQCHNUTJ-UHFFFAOYSA-N 0.000 claims 1
NYUVNSLNFBXZDF-NSHDSACASA-N 2,2-dimethyl-3-[[5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-yl]amino]propan-1-ol Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC(C)(C)CO)=C1 NYUVNSLNFBXZDF-NSHDSACASA-N 0.000 claims 1
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 1
GRFAVFQZSRHRKQ-UHFFFAOYSA-N 2-methyl-1-[(4-piperazin-1-ylpyridin-2-yl)amino]propan-2-ol Chemical compound C1=NC(NCC(C)(O)C)=CC(N2CCNCC2)=C1 GRFAVFQZSRHRKQ-UHFFFAOYSA-N 0.000 claims 1
VIBQHRSADYJDNY-UHFFFAOYSA-N 2-methyl-1-[(4-piperazin-1-ylpyrimidin-2-yl)amino]propan-2-ol Chemical compound CC(C)(O)CNC1=NC=CC(N2CCNCC2)=N1 VIBQHRSADYJDNY-UHFFFAOYSA-N 0.000 claims 1
LGNKHRUBXNOYBZ-UHFFFAOYSA-N 2-methyl-1-[[4-(4-methylpiperazin-1-yl)pyridin-2-yl]amino]propan-2-ol Chemical compound C1CN(C)CCN1C1=CC=NC(NCC(C)(C)O)=C1 LGNKHRUBXNOYBZ-UHFFFAOYSA-N 0.000 claims 1
MWKSIRBIKPTHGC-UHFFFAOYSA-N 2-methyl-1-[[4-(4-methylpiperazin-1-yl)pyrimidin-2-yl]amino]propan-2-ol Chemical compound C1CN(C)CCN1C1=CC=NC(NCC(C)(C)O)=N1 MWKSIRBIKPTHGC-UHFFFAOYSA-N 0.000 claims 1
VBTQJMKRADHVRY-LLVKDONJSA-N 2-methyl-1-[[4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-yl]amino]propan-2-ol Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC(C)(C)O)=C1 VBTQJMKRADHVRY-LLVKDONJSA-N 0.000 claims 1
XIUWYDQCVIWPSQ-SNVBAGLBSA-N 2-methyl-1-[[4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-yl]amino]propan-2-ol Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC(C)(C)O)=N1 XIUWYDQCVIWPSQ-SNVBAGLBSA-N 0.000 claims 1
VBTQJMKRADHVRY-NSHDSACASA-N 2-methyl-1-[[4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-yl]amino]propan-2-ol Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC(C)(C)O)=C1 VBTQJMKRADHVRY-NSHDSACASA-N 0.000 claims 1
LDMYQCQRMNCPAV-UHFFFAOYSA-N 2-methyl-1-[[4-[3-(methylamino)azetidin-1-yl]pyridin-2-yl]amino]propan-2-ol Chemical compound C1C(NC)CN1C1=CC=NC(NCC(C)(C)O)=C1 LDMYQCQRMNCPAV-UHFFFAOYSA-N 0.000 claims 1
LHUHRQHXXOIGLB-UHFFFAOYSA-N 2-methyl-1-[[4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-yl]amino]propan-2-ol Chemical compound C1C(NC)CN1C1=CC=NC(NCC(C)(C)O)=N1 LHUHRQHXXOIGLB-UHFFFAOYSA-N 0.000 claims 1
MPKMRZDINVKRAX-UHFFFAOYSA-N 3-(2-methylpropyl)pyridin-2-amine Chemical compound CC(C)CC1=CC=CN=C1N MPKMRZDINVKRAX-UHFFFAOYSA-N 0.000 claims 1
MVWGQDLCBGQJGA-UHFFFAOYSA-N 3-[(4-piperazin-1-ylpyrimidin-2-yl)amino]propan-1-ol Chemical compound OCCCNC1=NC=CC(N2CCNCC2)=N1 MVWGQDLCBGQJGA-UHFFFAOYSA-N 0.000 claims 1
IJCAWTJJSIJZAH-UHFFFAOYSA-N 3-[(5-piperazin-1-ylpyridazin-3-yl)amino]propan-1-ol Chemical compound N1=NC(NCCCO)=CC(N2CCNCC2)=C1 IJCAWTJJSIJZAH-UHFFFAOYSA-N 0.000 claims 1
IJZKPKMOGVCHIS-UHFFFAOYSA-N 3-[[4-(3-aminoazetidin-1-yl)pyrimidin-2-yl]amino]-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CNC1=NC=CC(N2CC(N)C2)=N1 IJZKPKMOGVCHIS-UHFFFAOYSA-N 0.000 claims 1
LKFAVFRTAHUROX-UHFFFAOYSA-N 3-[[4-(3-aminoazetidin-1-yl)pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1C(N)CN1C1=CC=NC(NCCCO)=N1 LKFAVFRTAHUROX-UHFFFAOYSA-N 0.000 claims 1
NQEWETZOHINIRC-UHFFFAOYSA-N 3-[[4-(4-methylpiperazin-1-yl)pyridin-2-yl]amino]propan-1-ol Chemical compound C1CN(C)CCN1C1=CC=NC(NCCCO)=C1 NQEWETZOHINIRC-UHFFFAOYSA-N 0.000 claims 1
GECTZQBBCADNPY-UHFFFAOYSA-N 3-[[4-(4-methylpiperazin-1-yl)pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1CN(C)CCN1C1=CC=NC(NCCCO)=N1 GECTZQBBCADNPY-UHFFFAOYSA-N 0.000 claims 1
GYRGOQPJNHODBA-MNOVXSKESA-N 3-[[4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound OCCCNC1=NC=CC(N2C[C@@H]3NCC[C@@H]3C2)=N1 GYRGOQPJNHODBA-MNOVXSKESA-N 0.000 claims 1
IMXPLIRERACZNW-SNVBAGLBSA-N 3-[[4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCCCO)=N1 IMXPLIRERACZNW-SNVBAGLBSA-N 0.000 claims 1
OSUHQYONZGAWNW-SNVBAGLBSA-N 3-[[4-[(3r)-3-aminopyrrolidin-1-yl]pyrimidin-2-yl]amino]-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CNC1=NC=CC(N2C[C@H](N)CC2)=N1 OSUHQYONZGAWNW-SNVBAGLBSA-N 0.000 claims 1
USPQEUTWQXCAOA-SECBINFHSA-N 3-[[4-[(3r)-3-aminopyrrolidin-1-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCCCO)=N1 USPQEUTWQXCAOA-SECBINFHSA-N 0.000 claims 1
BDBWYPVDWSZXKH-NSHDSACASA-N 3-[[4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCCCO)=C1 BDBWYPVDWSZXKH-NSHDSACASA-N 0.000 claims 1
IMXPLIRERACZNW-JTQLQIEISA-N 3-[[4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCCCO)=N1 IMXPLIRERACZNW-JTQLQIEISA-N 0.000 claims 1
OSUHQYONZGAWNW-JTQLQIEISA-N 3-[[4-[(3s)-3-aminopyrrolidin-1-yl]pyrimidin-2-yl]amino]-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CNC1=NC=CC(N2C[C@@H](N)CC2)=N1 OSUHQYONZGAWNW-JTQLQIEISA-N 0.000 claims 1
NESCVJRGFCOWED-UHFFFAOYSA-N 3-[[4-[3-(methylamino)azetidin-1-yl]pyridin-2-yl]amino]propan-1-ol Chemical compound C1C(NC)CN1C1=CC=NC(NCCCO)=C1 NESCVJRGFCOWED-UHFFFAOYSA-N 0.000 claims 1
SLQZEOLHVUKYQJ-UHFFFAOYSA-N 3-[[4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-yl]amino]propan-1-ol Chemical compound C1C(NC)CN1C1=CC=NC(NCCCO)=N1 SLQZEOLHVUKYQJ-UHFFFAOYSA-N 0.000 claims 1
HCGYHAIKHDIADZ-PWSUYJOCSA-N 3-[[5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]pyridazin-3-yl]amino]propan-1-ol Chemical compound N1=NC(NCCCO)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 HCGYHAIKHDIADZ-PWSUYJOCSA-N 0.000 claims 1
HFBXVWPBZRXZSP-SNVBAGLBSA-N 3-[[5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-yl]amino]propan-1-ol Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCCCO)=C1 HFBXVWPBZRXZSP-SNVBAGLBSA-N 0.000 claims 1
TWBSIRHQWMVCAE-SNVBAGLBSA-N 3-[[5-[(3r)-3-aminopyrrolidin-1-yl]pyridazin-3-yl]amino]-2,2-dimethylpropan-1-ol Chemical compound N1=NC(NCC(C)(CO)C)=CC(N2C[C@H](N)CC2)=C1 TWBSIRHQWMVCAE-SNVBAGLBSA-N 0.000 claims 1
YTQLNMQEEMHWIH-SECBINFHSA-N 3-[[5-[(3r)-3-aminopyrrolidin-1-yl]pyridazin-3-yl]amino]propan-1-ol Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCCCO)=C1 YTQLNMQEEMHWIH-SECBINFHSA-N 0.000 claims 1
HFBXVWPBZRXZSP-JTQLQIEISA-N 3-[[5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-yl]amino]propan-1-ol Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCCCO)=C1 HFBXVWPBZRXZSP-JTQLQIEISA-N 0.000 claims 1
YTQLNMQEEMHWIH-VIFPVBQESA-N 3-[[5-[(3s)-3-aminopyrrolidin-1-yl]pyridazin-3-yl]amino]propan-1-ol Chemical compound C1[C@@H](N)CCN1C1=CN=NC(NCCCO)=C1 YTQLNMQEEMHWIH-VIFPVBQESA-N 0.000 claims 1
BLIQSCCYVTZLNG-UHFFFAOYSA-N 3-[[5-[3-(methylamino)azetidin-1-yl]pyridazin-3-yl]amino]propan-1-ol Chemical compound C1C(NC)CN1C1=CN=NC(NCCCO)=C1 BLIQSCCYVTZLNG-UHFFFAOYSA-N 0.000 claims 1
AZHUBGIQDYLZDQ-UHFFFAOYSA-N 4-(1,4-diazepan-1-yl)-n-(2,2-dimethylpropyl)pyrimidin-2-amine Chemical compound CC(C)(C)CNC1=NC=CC(N2CCNCCC2)=N1 AZHUBGIQDYLZDQ-UHFFFAOYSA-N 0.000 claims 1
SRFFZXUAMSQKLK-UHFFFAOYSA-N 4-(2-methoxyethyl)pyrimidin-2-amine Chemical compound O(C)CCC1=NC(=NC=C1)N SRFFZXUAMSQKLK-UHFFFAOYSA-N 0.000 claims 1
RVVLRORASWSUEO-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-(2,2-dimethylpropyl)pyrimidin-2-amine Chemical compound CC(C)(C)CNC1=NC=CC(N2CC(N)C2)=N1 RVVLRORASWSUEO-UHFFFAOYSA-N 0.000 claims 1
SVTHLINSGZJXDW-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CNC1=NC=CC(N2CC(N)C2)=N1 SVTHLINSGZJXDW-UHFFFAOYSA-N 0.000 claims 1
WNBLIQJREQODKT-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-(3-bicyclo[2.2.1]heptanyl)pyrimidin-2-amine Chemical compound C1C(N)CN1C1=CC=NC(NC2C3CCC(C3)C2)=N1 WNBLIQJREQODKT-UHFFFAOYSA-N 0.000 claims 1
PKRJMNGUAXOIQX-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-(cyclopropylmethyl)pyrimidin-2-amine Chemical compound C1C(N)CN1C1=CC=NC(NCC2CC2)=N1 PKRJMNGUAXOIQX-UHFFFAOYSA-N 0.000 claims 1
OMSHTPQYPMTZCH-SECBINFHSA-N 4-(3-aminoazetidin-1-yl)-n-[(3r)-oxolan-3-yl]pyrimidin-2-amine Chemical compound C1C(N)CN1C1=CC=NC(N[C@H]2COCC2)=N1 OMSHTPQYPMTZCH-SECBINFHSA-N 0.000 claims 1
LVMCEWHNJTZVJJ-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-[(4-fluorophenyl)methyl]pyrimidin-2-amine Chemical compound C1C(N)CN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=N1 LVMCEWHNJTZVJJ-UHFFFAOYSA-N 0.000 claims 1
FJXNRFRNCRCQLQ-SNVBAGLBSA-N 4-(3-aminoazetidin-1-yl)-n-[[(2r)-oxolan-2-yl]methyl]pyrimidin-2-amine Chemical compound C1C(N)CN1C1=CC=NC(NC[C@@H]2OCCC2)=N1 FJXNRFRNCRCQLQ-SNVBAGLBSA-N 0.000 claims 1
MNKAPTBUWNJXOG-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-cyclopentylpyrimidin-2-amine Chemical compound C1C(N)CN1C1=CC=NC(NC2CCCC2)=N1 MNKAPTBUWNJXOG-UHFFFAOYSA-N 0.000 claims 1
LSOAOZZKDZZWDO-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-cyclopropylpyrimidin-2-amine Chemical compound C1C(N)CN1C1=CC=NC(NC2CC2)=N1 LSOAOZZKDZZWDO-UHFFFAOYSA-N 0.000 claims 1
DJUQWVYIHYDLMI-UHFFFAOYSA-N 4-(3-aminoazetidin-1-yl)-n-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)NC1=NC=CC(N2CC(N)C2)=N1 DJUQWVYIHYDLMI-UHFFFAOYSA-N 0.000 claims 1
MYCNPPHJKZGYMD-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(2-methylpropyl)pyridin-2-amine Chemical compound C1=NC(NCC(C)C)=CC(N2CCN(C)CC2)=C1 MYCNPPHJKZGYMD-UHFFFAOYSA-N 0.000 claims 1
RMJYXDNBHRKGCM-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CNC1=NC=CC(N2CCN(C)CC2)=N1 RMJYXDNBHRKGCM-UHFFFAOYSA-N 0.000 claims 1
ABLAPYBTHCHQOW-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(2-methylsulfanylethyl)pyrimidin-2-amine Chemical compound CSCCNC1=NC=CC(N2CCN(C)CC2)=N1 ABLAPYBTHCHQOW-UHFFFAOYSA-N 0.000 claims 1
SKRVLUOFLGTORO-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(2-phenylethyl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCCC=2C=CC=CC=2)=C1 SKRVLUOFLGTORO-UHFFFAOYSA-N 0.000 claims 1
BNXNWRSVYQHTOH-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(2-phenylethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCCC=2C=CC=CC=2)=N1 BNXNWRSVYQHTOH-UHFFFAOYSA-N 0.000 claims 1
MMDFHRHBDGVWGF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(oxan-4-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC2CCOCC2)=C1 MMDFHRHBDGVWGF-UHFFFAOYSA-N 0.000 claims 1
LMCGATVYSRDOQD-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(oxolan-2-ylmethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC2OCCC2)=N1 LMCGATVYSRDOQD-UHFFFAOYSA-N 0.000 claims 1
IGHDOZUDSAZHLG-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(pyridin-2-ylmethyl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=C1 IGHDOZUDSAZHLG-UHFFFAOYSA-N 0.000 claims 1
HJFUUEJYYDZJJM-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-(pyridin-2-ylmethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=N1 HJFUUEJYYDZJJM-UHFFFAOYSA-N 0.000 claims 1
DIFGWGZGNSNLKV-SYNHAJSKSA-N 4-(4-methylpiperazin-1-yl)-n-[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]pyridin-2-amine Chemical compound N([C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)C(N=CC=1)=CC=1N1CCN(C)CC1 DIFGWGZGNSNLKV-SYNHAJSKSA-N 0.000 claims 1
PYGPJEIQBZAFSY-AUCMRZJMSA-N 4-(4-methylpiperazin-1-yl)-n-[(1r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridin-2-amine Chemical compound CC([C@@]1(C[C@](C2)(C1(C)C)[H])[H])C2NC(N=CC=1)=CC=1N1CCN(C)CC1 PYGPJEIQBZAFSY-AUCMRZJMSA-N 0.000 claims 1
FLAJYPXDGOGNFQ-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-n-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)NC1=NC=CC(N2CCN(C)CC2)=N1 FLAJYPXDGOGNFQ-UHFFFAOYSA-N 0.000 claims 1
REYXYXRKAJODBP-YSIGMKLFSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(1-adamantyl)pyridin-2-amine Chemical compound C1C(C2)CC(C3)CC2CC13NC1=CC(N2C[C@H]3CCN[C@H]3C2)=CC=N1 REYXYXRKAJODBP-YSIGMKLFSA-N 0.000 claims 1
XFQPQUIGSNARRD-OCCSQVGLSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(2,2-dimethylpropyl)pyridin-2-amine Chemical compound C1=NC(NCC(C)(C)C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 XFQPQUIGSNARRD-OCCSQVGLSA-N 0.000 claims 1
DRGLVMMQLDMWCZ-RHPFDVKYSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(2-adamantyl)pyridin-2-amine Chemical compound C1C(CC2C3)CC3CC1C2NC1=CC(N2C[C@H]3CCN[C@H]3C2)=CC=N1 DRGLVMMQLDMWCZ-RHPFDVKYSA-N 0.000 claims 1
WBHNMFPFIPPUDO-MNOVXSKESA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(2-methoxyethyl)pyrimidin-2-amine Chemical compound COCCNC1=NC=CC(N2C[C@@H]3NCC[C@@H]3C2)=N1 WBHNMFPFIPPUDO-MNOVXSKESA-N 0.000 claims 1
TVKXAXGHODHZQT-NEPJUHHUSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CNC1=NC=CC(N2C[C@@H]3NCC[C@@H]3C2)=N1 TVKXAXGHODHZQT-NEPJUHHUSA-N 0.000 claims 1
AKFJLXLGFVRKHW-WBVHZDCISA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(cyclohexylmethyl)pyridin-2-amine Chemical compound C=1C(N2C[C@@H]3NCC[C@@H]3C2)=CC=NC=1NCC1CCCCC1 AKFJLXLGFVRKHW-WBVHZDCISA-N 0.000 claims 1
HEZXAQAYFVBMBI-CABCVRRESA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(cyclohexylmethyl)pyrimidin-2-amine Chemical compound N=1C=CC(N2C[C@@H]3NCC[C@@H]3C2)=NC=1NCC1CCCCC1 HEZXAQAYFVBMBI-CABCVRRESA-N 0.000 claims 1
DEQKBYFVXAQBDL-ZBFHGGJFSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(cyclopentylmethyl)pyridin-2-amine Chemical compound C=1C(N2C[C@@H]3NCC[C@@H]3C2)=CC=NC=1NCC1CCCC1 DEQKBYFVXAQBDL-ZBFHGGJFSA-N 0.000 claims 1
MFHALQPIBQRFEQ-DOMZBBRYSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(oxan-4-yl)pyridin-2-amine Chemical compound C([C@H]1CCN[C@H]1C1)N1C(C=1)=CC=NC=1NC1CCOCC1 MFHALQPIBQRFEQ-DOMZBBRYSA-N 0.000 claims 1
NDUVCIBQCLNNPK-KYJSFNMBSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-[(1r)-1-cyclohexylethyl]pyridin-2-amine Chemical compound C1([C@H](NC=2N=CC=C(C=2)N2C[C@@H]3NCC[C@@H]3C2)C)CCCCC1 NDUVCIBQCLNNPK-KYJSFNMBSA-N 0.000 claims 1
SJNJRCKMFCAMHN-BMFZPTHFSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-[(1r)-1-cyclohexylethyl]pyrimidin-2-amine Chemical compound C1([C@H](NC=2N=C(C=CN=2)N2C[C@@H]3NCC[C@@H]3C2)C)CCCCC1 SJNJRCKMFCAMHN-BMFZPTHFSA-N 0.000 claims 1
HRAVLWRABOTGHJ-BMFZPTHFSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-[(1r)-1-phenylethyl]pyrimidin-2-amine Chemical compound C1([C@H](NC=2N=C(C=CN=2)N2C[C@@H]3NCC[C@@H]3C2)C)=CC=CC=C1 HRAVLWRABOTGHJ-BMFZPTHFSA-N 0.000 claims 1
YDCMGULTZPJOLX-PAYTZWKFSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-[(1r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridin-2-amine Chemical compound C=1C(N2C[C@@H]3NCC[C@@H]3C2)=CC=NC=1NC1C(C)[C@@]([H])(C2(C)C)C[C@]2([H])C1 YDCMGULTZPJOLX-PAYTZWKFSA-N 0.000 claims 1
YTANLRPBUGMQNT-HIFRSBDPSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-[(4-fluorophenyl)methyl]pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1CNC1=NC=CC(N2C[C@@H]3NCC[C@@H]3C2)=N1 YTANLRPBUGMQNT-HIFRSBDPSA-N 0.000 claims 1
GTQOCUNTBUOXKD-SMYFESCOSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]pyridin-2-amine Chemical compound C=1C(N2C[C@@H]3NCC[C@@H]3C2)=CC=NC=1NC[C@@H]1[C@@]([H])(C2(C)C)C[C@]2([H])CC1 GTQOCUNTBUOXKD-SMYFESCOSA-N 0.000 claims 1
IIRBZWGGHDVZIO-NRKLIOEPSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]pyrimidin-2-amine Chemical compound C1=CC(N2C[C@@H]3NCC[C@@H]3C2)=NC(NC[C@@H]2[C@@]3(C[C@](CC2)(C3(C)C)[H])[H])=N1 IIRBZWGGHDVZIO-NRKLIOEPSA-N 0.000 claims 1
KTLSRDLBYBSXOT-DOMZBBRYSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-cyclopentylpyridin-2-amine Chemical compound C1CCCC1NC1=CC(N2C[C@@H]3NCC[C@@H]3C2)=CC=N1 KTLSRDLBYBSXOT-DOMZBBRYSA-N 0.000 claims 1
DNMWSZJIKALJMN-YPMHNXCESA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound C1CCCC1NC1=NC=CC(N2C[C@@H]3NCC[C@@H]3C2)=N1 DNMWSZJIKALJMN-YPMHNXCESA-N 0.000 claims 1
QVFGNOOULWCILC-KOLCDFICSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-cyclopropylpyrimidin-2-amine Chemical compound C1CC1NC1=NC=CC(N2C[C@@H]3NCC[C@@H]3C2)=N1 QVFGNOOULWCILC-KOLCDFICSA-N 0.000 claims 1
WFZBQXUFLUOFRU-YPMHNXCESA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-tert-butylpyridin-2-amine Chemical compound C1=NC(NC(C)(C)C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 WFZBQXUFLUOFRU-YPMHNXCESA-N 0.000 claims 1
UAOJUVSUWLARMX-GFCCVEGCSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(2-methylpropyl)pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC(C)C)=C1 UAOJUVSUWLARMX-GFCCVEGCSA-N 0.000 claims 1
ROOXXUYZFBALHV-LLVKDONJSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(2-methylpropyl)pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC(C)C)=N1 ROOXXUYZFBALHV-LLVKDONJSA-N 0.000 claims 1
MAYCAHGKAVJRBH-OAHLLOKOSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(2-phenylethyl)pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCCC=2C=CC=CC=2)=N1 MAYCAHGKAVJRBH-OAHLLOKOSA-N 0.000 claims 1
IPWSPKPLVXGSQI-CYBMUJFWSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(oxan-4-yl)pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC2CCOCC2)=C1 IPWSPKPLVXGSQI-CYBMUJFWSA-N 0.000 claims 1
MWBRNXCGCTZRPH-AFWNMAIHSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(oxolan-2-ylmethyl)pyridin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1C1=CC=NC(NCC2OCCC2)=C1 MWBRNXCGCTZRPH-AFWNMAIHSA-N 0.000 claims 1
IZHXWKIRBWAWDT-CYBMUJFWSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=N1 IZHXWKIRBWAWDT-CYBMUJFWSA-N 0.000 claims 1
DAAIGUOFWABLPA-UKRRQHHQSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r)-1-phenylethyl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(N[C@H](C)C=2C=CC=CC=2)=N1 DAAIGUOFWABLPA-UKRRQHHQSA-N 0.000 claims 1
HFLZBUUCZOGTRI-UOSKARGWSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]pyridin-2-amine Chemical compound N([C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)C(N=CC=1)=CC=1N1CC[C@@H](NC)C1 HFLZBUUCZOGTRI-UOSKARGWSA-N 0.000 claims 1
NDWRBIGSNYGHME-CUYVQJCZSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrimidin-2-amine Chemical compound N([C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)C(N=1)=NC=CC=1N1CC[C@@H](NC)C1 NDWRBIGSNYGHME-CUYVQJCZSA-N 0.000 claims 1
FBFNSCZZANKPAN-INSJMTBZSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r,3s,4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridin-2-amine Chemical compound N([C@@H]1[C@@H](C)[C@@]2(C[C@](C1)(C2(C)C)[H])[H])C(N=CC=1)=CC=1N1CC[C@@H](NC)C1 FBFNSCZZANKPAN-INSJMTBZSA-N 0.000 claims 1
ZZOXQQOMBIZPSH-OTJKEOIZSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r,3s,4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyrimidin-2-amine Chemical compound N([C@@H]1[C@@H](C)[C@@]2(C[C@](C1)(C2(C)C)[H])[H])C(N=1)=NC=CC=1N1CC[C@@H](NC)C1 ZZOXQQOMBIZPSH-OTJKEOIZSA-N 0.000 claims 1
FBFNSCZZANKPAN-JAPOXJDPSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1s,3r,4r,5r)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridin-2-amine Chemical compound N([C@H]1[C@H](C)[C@]2(C[C@@](C1)(C2(C)C)[H])[H])C(N=CC=1)=CC=1N1CC[C@@H](NC)C1 FBFNSCZZANKPAN-JAPOXJDPSA-N 0.000 claims 1
LSQDZUMRSCAKOV-MBORUXJMSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(3r)-oxolan-3-yl]pyridin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1C1=CC=NC(N[C@H]2COCC2)=C1 LSQDZUMRSCAKOV-MBORUXJMSA-N 0.000 claims 1
BWSNZRFYBWRBAX-OAHLLOKOSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(4-methylphenyl)methyl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC=2C=CC(C)=CC=2)=N1 BWSNZRFYBWRBAX-OAHLLOKOSA-N 0.000 claims 1
XGBRAIUXWRQSGJ-CQSZACIVSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-phenylpyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC=2C=CC=CC=2)=C1 XGBRAIUXWRQSGJ-CQSZACIVSA-N 0.000 claims 1
BVMYJSFGALTWOF-LLVKDONJSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-propan-2-ylpyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC(C)C)=C1 BVMYJSFGALTWOF-LLVKDONJSA-N 0.000 claims 1
PCWWILBQNYWVFM-SNVBAGLBSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC(C)C)=N1 PCWWILBQNYWVFM-SNVBAGLBSA-N 0.000 claims 1
DQYONUZKUHTFPJ-NVJADKKVSA-N 4-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-propylpyridin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1=NC(NCCC)=CC(N2C[C@@H](CC2)NC)=C1 DQYONUZKUHTFPJ-NVJADKKVSA-N 0.000 claims 1
XOGNVWVGXPSTMU-SNVBAGLBSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(2,2-dimethylpropyl)pyrimidin-2-amine Chemical compound CC(C)(C)CNC1=NC=CC(N2C[C@H](N)CC2)=N1 XOGNVWVGXPSTMU-SNVBAGLBSA-N 0.000 claims 1
XTRSNNDFWWVAJZ-SNVBAGLBSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(2-methoxyethyl)pyridin-2-amine Chemical compound C1=NC(NCCOC)=CC(N2C[C@H](N)CC2)=C1 XTRSNNDFWWVAJZ-SNVBAGLBSA-N 0.000 claims 1
LNRVUQSIYIAQSE-SECBINFHSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(2-methoxyethyl)pyrimidin-2-amine Chemical compound COCCNC1=NC=CC(N2C[C@H](N)CC2)=N1 LNRVUQSIYIAQSE-SECBINFHSA-N 0.000 claims 1
IAPFMZATXNRZAV-LLVKDONJSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(2-methylpropyl)pyridin-2-amine Chemical compound C1=NC(NCC(C)C)=CC(N2C[C@H](N)CC2)=C1 IAPFMZATXNRZAV-LLVKDONJSA-N 0.000 claims 1
LAEDXNMMHGVCRC-CQSZACIVSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(2-phenylethyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCCC=2C=CC=CC=2)=N1 LAEDXNMMHGVCRC-CQSZACIVSA-N 0.000 claims 1
UKQITGWWTPWPJE-PYYBWGNESA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(3-bicyclo[2.2.1]heptanyl)pyridin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=C1 UKQITGWWTPWPJE-PYYBWGNESA-N 0.000 claims 1
FGJKRFYZAVCCNL-AYNROABZSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(3-bicyclo[2.2.1]heptanyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=N1 FGJKRFYZAVCCNL-AYNROABZSA-N 0.000 claims 1
GSWRPUBHOSAXNH-SECBINFHSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(4,4,4-trifluorobutyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCCCC(F)(F)F)=N1 GSWRPUBHOSAXNH-SECBINFHSA-N 0.000 claims 1
QGOCUFWNYMXSMM-CYBMUJFWSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(cyclohexylmethyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC2CCCCC2)=N1 QGOCUFWNYMXSMM-CYBMUJFWSA-N 0.000 claims 1
MSCPBDXORVNAPK-CYBMUJFWSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(cyclopentylmethyl)pyridin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC2CCCC2)=C1 MSCPBDXORVNAPK-CYBMUJFWSA-N 0.000 claims 1
YSWDEXOJFUCVOW-GFCCVEGCSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(cyclopentylmethyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC2CCCC2)=N1 YSWDEXOJFUCVOW-GFCCVEGCSA-N 0.000 claims 1
AKQLSWADFSKYCI-SNVBAGLBSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(cyclopropylmethyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC2CC2)=N1 AKQLSWADFSKYCI-SNVBAGLBSA-N 0.000 claims 1
FFQSJNCCHVEUDV-SNVBAGLBSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(oxan-4-yl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2CCOCC2)=N1 FFQSJNCCHVEUDV-SNVBAGLBSA-N 0.000 claims 1
VWADBZHEYXNXML-NFJWQWPMSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(oxolan-2-ylmethyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC2OCCC2)=N1 VWADBZHEYXNXML-NFJWQWPMSA-N 0.000 claims 1
VTXWLQGYXMOYPG-LLVKDONJSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=N1 VTXWLQGYXMOYPG-LLVKDONJSA-N 0.000 claims 1
SMSQGPKFXUYAQQ-TZMCWYRMSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(1r)-1-cyclohexylethyl]pyrimidin-2-amine Chemical compound N([C@H](C)C1CCCCC1)C(N=1)=NC=CC=1N1CC[C@@H](N)C1 SMSQGPKFXUYAQQ-TZMCWYRMSA-N 0.000 claims 1
MNAQKNMQPXWADC-TZMCWYRMSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(1r)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1N1CC[C@@H](N)C1 MNAQKNMQPXWADC-TZMCWYRMSA-N 0.000 claims 1
UPMCVXNGKMMLLC-ZXTQRBJTSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrimidin-2-amine Chemical compound N([C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)C(N=1)=NC=CC=1N1CC[C@@H](N)C1 UPMCVXNGKMMLLC-ZXTQRBJTSA-N 0.000 claims 1
QKWILBVMTJMGMW-QRTUWBSPSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(1r,3s,4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyrimidin-2-amine Chemical compound N([C@@H]1[C@@H](C)[C@@]2(C[C@](C1)(C2(C)C)[H])[H])C(N=1)=NC=CC=1N1CC[C@@H](N)C1 QKWILBVMTJMGMW-QRTUWBSPSA-N 0.000 claims 1
AKIGRHATLPZWFK-NXEZZACHSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(3r)-oxolan-3-yl]pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(N[C@H]2COCC2)=N1 AKIGRHATLPZWFK-NXEZZACHSA-N 0.000 claims 1
FWSBBVCZJMZFNK-CYBMUJFWSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(4-fluorophenyl)methyl]pyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=N1 FWSBBVCZJMZFNK-CYBMUJFWSA-N 0.000 claims 1
PHNXVPNSJHMYGL-CYBMUJFWSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(4-methoxyphenyl)methyl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NC=CC(N2C[C@H](N)CC2)=N1 PHNXVPNSJHMYGL-CYBMUJFWSA-N 0.000 claims 1
FFFNIVHJUFKADJ-CQSZACIVSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(4-methylphenyl)methyl]pyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1CNC1=NC=CC(N2C[C@H](N)CC2)=N1 FFFNIVHJUFKADJ-CQSZACIVSA-N 0.000 claims 1
BROFGQDXVACYPP-MIGSVPMKSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-[(6,6-dimethyl-4-bicyclo[3.1.1]heptanyl)methyl]pyrimidin-2-amine Chemical compound CC1(C)C(CC2)CC1C2CNC(N=1)=NC=CC=1N1CC[C@@H](N)C1 BROFGQDXVACYPP-MIGSVPMKSA-N 0.000 claims 1
SONYBPHJTWSANN-CYBMUJFWSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-benzylpyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NCC=2C=CC=CC=2)=N1 SONYBPHJTWSANN-CYBMUJFWSA-N 0.000 claims 1
FOSUMAIGKSQQRB-LLVKDONJSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-butylpyridin-2-amine Chemical compound C1=NC(NCCCC)=CC(N2C[C@H](N)CC2)=C1 FOSUMAIGKSQQRB-LLVKDONJSA-N 0.000 claims 1
AHIONDMBSNMOFN-SNVBAGLBSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-butylpyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(N2C[C@H](N)CC2)=N1 AHIONDMBSNMOFN-SNVBAGLBSA-N 0.000 claims 1
UFCNHUUQPKRLHV-SECBINFHSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclobutylpyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2CCC2)=N1 UFCNHUUQPKRLHV-SECBINFHSA-N 0.000 claims 1
PZHVVLSVNJFJTE-GFCCVEGCSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclohexylpyridin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2CCCCC2)=C1 PZHVVLSVNJFJTE-GFCCVEGCSA-N 0.000 claims 1
NTUREPPETJZDTC-LLVKDONJSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclohexylpyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2CCCCC2)=N1 NTUREPPETJZDTC-LLVKDONJSA-N 0.000 claims 1
RDYXIBULNAESPE-LLVKDONJSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclopentylpyridin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2CCCC2)=C1 RDYXIBULNAESPE-LLVKDONJSA-N 0.000 claims 1
GZAOBGNGKYFFHA-SNVBAGLBSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2CCCC2)=N1 GZAOBGNGKYFFHA-SNVBAGLBSA-N 0.000 claims 1
OACCOZPTVLOIMI-MRVPVSSYSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclopropylpyrimidin-2-amine Chemical compound C1[C@H](N)CCN1C1=CC=NC(NC2CC2)=N1 OACCOZPTVLOIMI-MRVPVSSYSA-N 0.000 claims 1
VQEQAMJPARUDIU-SNVBAGLBSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-propan-2-ylpyridin-2-amine Chemical compound C1=NC(NC(C)C)=CC(N2C[C@H](N)CC2)=C1 VQEQAMJPARUDIU-SNVBAGLBSA-N 0.000 claims 1
BZDMQXGVTNULAB-SECBINFHSA-N 4-[(3r)-3-aminopyrrolidin-1-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)NC1=NC=CC(N2C[C@H](N)CC2)=N1 BZDMQXGVTNULAB-SECBINFHSA-N 0.000 claims 1
UAOJUVSUWLARMX-LBPRGKRZSA-N 4-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(2-methylpropyl)pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC(C)C)=C1 UAOJUVSUWLARMX-LBPRGKRZSA-N 0.000 claims 1
ROOXXUYZFBALHV-NSHDSACASA-N 4-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(2-methylpropyl)pyrimidin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC(C)C)=N1 ROOXXUYZFBALHV-NSHDSACASA-N 0.000 claims 1
IFSGOMTUIJGDOW-INIZCTEOSA-N 4-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(2-phenylethyl)pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCCC=2C=CC=CC=2)=C1 IFSGOMTUIJGDOW-INIZCTEOSA-N 0.000 claims 1
OGZIPEKVYQCSKY-AWEZNQCLSA-N 4-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=C1 OGZIPEKVYQCSKY-AWEZNQCLSA-N 0.000 claims 1
IZHXWKIRBWAWDT-ZDUSSCGKSA-N 4-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyrimidin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=N1 IZHXWKIRBWAWDT-ZDUSSCGKSA-N 0.000 claims 1
HFLZBUUCZOGTRI-RPWFAHAXSA-N 4-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]pyridin-2-amine Chemical compound N([C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)C(N=CC=1)=CC=1N1CC[C@H](NC)C1 HFLZBUUCZOGTRI-RPWFAHAXSA-N 0.000 claims 1
FBFNSCZZANKPAN-HNJNVOIISA-N 4-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridin-2-amine Chemical compound CC([C@@]1(C[C@](C2)(C1(C)C)[H])[H])C2NC(N=CC=1)=CC=1N1CC[C@H](NC)C1 FBFNSCZZANKPAN-HNJNVOIISA-N 0.000 claims 1
XOGNVWVGXPSTMU-JTQLQIEISA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(2,2-dimethylpropyl)pyrimidin-2-amine Chemical compound CC(C)(C)CNC1=NC=CC(N2C[C@@H](N)CC2)=N1 XOGNVWVGXPSTMU-JTQLQIEISA-N 0.000 claims 1
XTRSNNDFWWVAJZ-JTQLQIEISA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(2-methoxyethyl)pyridin-2-amine Chemical compound C1=NC(NCCOC)=CC(N2C[C@@H](N)CC2)=C1 XTRSNNDFWWVAJZ-JTQLQIEISA-N 0.000 claims 1
IAPFMZATXNRZAV-NSHDSACASA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(2-methylpropyl)pyridin-2-amine Chemical compound C1=NC(NCC(C)C)=CC(N2C[C@@H](N)CC2)=C1 IAPFMZATXNRZAV-NSHDSACASA-N 0.000 claims 1
HPANPAIFSIFMPT-JTQLQIEISA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(2-methylpropyl)pyrimidin-2-amine Chemical compound CC(C)CNC1=NC=CC(N2C[C@@H](N)CC2)=N1 HPANPAIFSIFMPT-JTQLQIEISA-N 0.000 claims 1
JLZBXKHVWPYIQT-HNNXBMFYSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(2-phenylethyl)pyridin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCCC=2C=CC=CC=2)=C1 JLZBXKHVWPYIQT-HNNXBMFYSA-N 0.000 claims 1
FGJKRFYZAVCCNL-ARAJFMJPSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(3-bicyclo[2.2.1]heptanyl)pyrimidin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=N1 FGJKRFYZAVCCNL-ARAJFMJPSA-N 0.000 claims 1
YSWDEXOJFUCVOW-LBPRGKRZSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(cyclopentylmethyl)pyrimidin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCC2CCCC2)=N1 YSWDEXOJFUCVOW-LBPRGKRZSA-N 0.000 claims 1
AKQLSWADFSKYCI-JTQLQIEISA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(cyclopropylmethyl)pyrimidin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCC2CC2)=N1 AKQLSWADFSKYCI-JTQLQIEISA-N 0.000 claims 1
QELWZPBWFJCSMK-LBPRGKRZSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyridin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=C1 QELWZPBWFJCSMK-LBPRGKRZSA-N 0.000 claims 1
VTXWLQGYXMOYPG-NSHDSACASA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyrimidin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCC=2N=CC=CC=2)=N1 VTXWLQGYXMOYPG-NSHDSACASA-N 0.000 claims 1
BPQABQDDJIOQOT-AWEZNQCLSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-[(4-fluorophenyl)methyl]pyridin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=C1 BPQABQDDJIOQOT-AWEZNQCLSA-N 0.000 claims 1
FWSBBVCZJMZFNK-ZDUSSCGKSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-[(4-fluorophenyl)methyl]pyrimidin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=N1 FWSBBVCZJMZFNK-ZDUSSCGKSA-N 0.000 claims 1
KOMGWWGRLAIFNA-AWEZNQCLSA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-benzylpyridin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NCC=2C=CC=CC=2)=C1 KOMGWWGRLAIFNA-AWEZNQCLSA-N 0.000 claims 1
AHIONDMBSNMOFN-JTQLQIEISA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-butylpyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(N2C[C@@H](N)CC2)=N1 AHIONDMBSNMOFN-JTQLQIEISA-N 0.000 claims 1
NTUREPPETJZDTC-NSHDSACASA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-cyclohexylpyrimidin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NC2CCCCC2)=N1 NTUREPPETJZDTC-NSHDSACASA-N 0.000 claims 1
RDYXIBULNAESPE-NSHDSACASA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-cyclopentylpyridin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NC2CCCC2)=C1 RDYXIBULNAESPE-NSHDSACASA-N 0.000 claims 1
GZAOBGNGKYFFHA-JTQLQIEISA-N 4-[(3s)-3-aminopyrrolidin-1-yl]-n-cyclopentylpyrimidin-2-amine Chemical compound C1[C@@H](N)CCN1C1=CC=NC(NC2CCCC2)=N1 GZAOBGNGKYFFHA-JTQLQIEISA-N 0.000 claims 1
NOUHIGBJYCGKIK-UHFFFAOYSA-N 4-[3-(methylamino)azetidin-1-yl]-n-(2-methylpropyl)pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC(C)C)=C1 NOUHIGBJYCGKIK-UHFFFAOYSA-N 0.000 claims 1
YOMUIBPHLNTTBU-UHFFFAOYSA-N 4-[3-(methylamino)azetidin-1-yl]-n-(2-phenylethyl)pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCCC=2C=CC=CC=2)=C1 YOMUIBPHLNTTBU-UHFFFAOYSA-N 0.000 claims 1
FBCMFHULVCEVFM-UHFFFAOYSA-N 4-[3-(methylamino)azetidin-1-yl]-n-(oxan-4-yl)pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NC2CCOCC2)=N1 FBCMFHULVCEVFM-UHFFFAOYSA-N 0.000 claims 1
YHIXVKAXZIIUAP-UHFFFAOYSA-N 4-[3-(methylamino)azetidin-1-yl]-n-(pyridin-2-ylmethyl)pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC=2N=CC=CC=2)=C1 YHIXVKAXZIIUAP-UHFFFAOYSA-N 0.000 claims 1
KHNJUKXGARMATD-UHFFFAOYSA-N 4-[3-(methylamino)azetidin-1-yl]-n-(pyridin-2-ylmethyl)pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC=2N=CC=CC=2)=N1 KHNJUKXGARMATD-UHFFFAOYSA-N 0.000 claims 1
LJBVZCCUDASQJA-IAISJRAMSA-N 4-[3-(methylamino)azetidin-1-yl]-n-[(1r,3s,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrimidin-2-amine Chemical compound N([C@@H]1[C@@]2(CC[C@](C1)(C2(C)C)[H])C)C(N=1)=NC=CC=1N1CC(NC)C1 LJBVZCCUDASQJA-IAISJRAMSA-N 0.000 claims 1
LLHWCGCILGARLZ-FNIIMMMJSA-N 4-[3-(methylamino)azetidin-1-yl]-n-[(1r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridin-2-amine Chemical class CC([C@@]1(C[C@](C2)(C1(C)C)[H])[H])C2NC(N=CC=1)=CC=1N1CC(NC)C1 LLHWCGCILGARLZ-FNIIMMMJSA-N 0.000 claims 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
GHFIQOFGDCBBCW-UHFFFAOYSA-N 4-piperazin-1-yl-n-(4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl)pyrimidin-2-amine Chemical compound CC1C(C2(C)C)CC2CC1NC(N=1)=NC=CC=1N1CCNCC1 GHFIQOFGDCBBCW-UHFFFAOYSA-N 0.000 claims 1
RQKRTLPPVXVYGU-UHFFFAOYSA-N 4-piperazin-1-yl-n-(pyridin-2-ylmethyl)pyridin-2-amine Chemical compound C=1C=CC=NC=1CNC(N=CC=1)=CC=1N1CCNCC1 RQKRTLPPVXVYGU-UHFFFAOYSA-N 0.000 claims 1
CPWZLRUBXDGILI-UHFFFAOYSA-N 4-piperazin-1-yl-n-(pyridin-2-ylmethyl)pyrimidin-2-amine Chemical compound C=1C=CC=NC=1CNC(N=1)=NC=CC=1N1CCNCC1 CPWZLRUBXDGILI-UHFFFAOYSA-N 0.000 claims 1
GHFIQOFGDCBBCW-XGUBFFRZSA-N 4-piperazin-1-yl-n-[(1r,3s,4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyrimidin-2-amine Chemical compound N([C@@H]1[C@@H](C)[C@@]2(C[C@](C1)(C2(C)C)[H])[H])C(N=1)=NC=CC=1N1CCNCC1 GHFIQOFGDCBBCW-XGUBFFRZSA-N 0.000 claims 1
AWNJSUMHPQAKMW-HTUOJYHCSA-N 4-piperazin-1-yl-n-[(1r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridin-2-amine Chemical compound CC([C@@]1(C[C@](C2)(C1(C)C)[H])[H])C2NC(N=CC=1)=CC=1N1CCNCC1 AWNJSUMHPQAKMW-HTUOJYHCSA-N 0.000 claims 1
WZBULDQXTUCTBZ-UHFFFAOYSA-N 4-piperazin-1-yl-n-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)NC1=NC=CC(N2CCNCC2)=N1 WZBULDQXTUCTBZ-UHFFFAOYSA-N 0.000 claims 1
VTVBPMMNSULVMC-UHFFFAOYSA-N 4-piperazin-1-yl-n-propylpyridin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1=NC(NCCC)=CC(N2CCNCC2)=C1 VTVBPMMNSULVMC-UHFFFAOYSA-N 0.000 claims 1
HVKUATGZMUFYSI-UHFFFAOYSA-N 5-(1,4-diazepan-1-yl)-n-(2,2-dimethylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)(C)C)=CC(N2CCNCCC2)=C1 HVKUATGZMUFYSI-UHFFFAOYSA-N 0.000 claims 1
YQQASZBBNAGKRN-UHFFFAOYSA-N 5-(3-aminoazetidin-1-yl)-n-(2,2-dimethylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)(C)C)=CC(N2CC(N)C2)=C1 YQQASZBBNAGKRN-UHFFFAOYSA-N 0.000 claims 1
OHEJGSBBEMQHTA-UHFFFAOYSA-N 5-(3-aminoazetidin-1-yl)-n-(2-methylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)C)=CC(N2CC(N)C2)=C1 OHEJGSBBEMQHTA-UHFFFAOYSA-N 0.000 claims 1
DKSISXNNXLOIMF-UHFFFAOYSA-N 5-(3-aminoazetidin-1-yl)-n-(3-bicyclo[2.2.1]heptanyl)pyridazin-3-amine Chemical compound C1C(N)CN1C1=CN=NC(NC2C3CCC(C3)C2)=C1 DKSISXNNXLOIMF-UHFFFAOYSA-N 0.000 claims 1
OVRCKWWMBXGJLM-UHFFFAOYSA-N 5-(3-aminoazetidin-1-yl)-n-(cyclopentylmethyl)pyridazin-3-amine Chemical compound C1C(N)CN1C1=CN=NC(NCC2CCCC2)=C1 OVRCKWWMBXGJLM-UHFFFAOYSA-N 0.000 claims 1
NQAKLOMPOPCNNQ-XUJVJEKNSA-N 5-(3-aminoazetidin-1-yl)-n-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]pyridazin-3-amine Chemical class C([C@@H]1[C@@]2(C[C@](CC1)(C2(C)C)[H])[H])NC(N=NC=1)=CC=1N1CC(N)C1 NQAKLOMPOPCNNQ-XUJVJEKNSA-N 0.000 claims 1
IINYXSNXKJFQKW-UHFFFAOYSA-N 5-(3-aminoazetidin-1-yl)-n-benzylpyridazin-3-amine Chemical compound C1C(N)CN1C1=CN=NC(NCC=2C=CC=CC=2)=C1 IINYXSNXKJFQKW-UHFFFAOYSA-N 0.000 claims 1
WALGNHZHJOLFOM-UHFFFAOYSA-N 5-(3-aminoazetidin-1-yl)-n-cyclopentylpyridazin-3-amine Chemical compound C1C(N)CN1C1=CN=NC(NC2CCCC2)=C1 WALGNHZHJOLFOM-UHFFFAOYSA-N 0.000 claims 1
DEIJZLPCDJFZSB-UHFFFAOYSA-N 5-(3-aminoazetidin-1-yl)-n-cyclopropylpyridazin-3-amine Chemical compound C1C(N)CN1C1=CN=NC(NC2CC2)=C1 DEIJZLPCDJFZSB-UHFFFAOYSA-N 0.000 claims 1
GDERZZCOGRXYBU-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)-n-(2-methylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)C)=CC(N2CCN(C)CC2)=C1 GDERZZCOGRXYBU-UHFFFAOYSA-N 0.000 claims 1
WGGXSURCZWXXHR-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)-n-(2-phenylethyl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CN=NC(NCCC=2C=CC=CC=2)=C1 WGGXSURCZWXXHR-UHFFFAOYSA-N 0.000 claims 1
ZEJKHLDTLFPIOM-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)-n-(pyridin-2-ylmethyl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CN=NC(NCC=2N=CC=CC=2)=C1 ZEJKHLDTLFPIOM-UHFFFAOYSA-N 0.000 claims 1
XBSGWINJGHFASF-YPMHNXCESA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(2-methylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)C)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 XBSGWINJGHFASF-YPMHNXCESA-N 0.000 claims 1
NWOOLRIEPSARDE-HIFRSBDPSA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-(cyclopentylmethyl)pyridazin-3-amine Chemical compound C=1C(N2C[C@@H]3NCC[C@@H]3C2)=CN=NC=1NCC1CCCC1 NWOOLRIEPSARDE-HIFRSBDPSA-N 0.000 claims 1
RUMVONQLNFJNCH-YPMHNXCESA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-butylpyridazin-3-amine Chemical compound N1=NC(NCCCC)=CC(N2C[C@@H]3NCC[C@@H]3C2)=C1 RUMVONQLNFJNCH-YPMHNXCESA-N 0.000 claims 1
ABHPVOANRZYXQV-RISCZKNCSA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-cyclopentylpyridazin-3-amine Chemical compound C1CCCC1NC1=CC(N2C[C@@H]3NCC[C@@H]3C2)=CN=N1 ABHPVOANRZYXQV-RISCZKNCSA-N 0.000 claims 1
USMZMISKJYQBQP-SKDRFNHKSA-N 5-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-n-cyclopropylpyridazin-3-amine Chemical compound C1CC1NC1=CC(N2C[C@@H]3NCC[C@@H]3C2)=CN=N1 USMZMISKJYQBQP-SKDRFNHKSA-N 0.000 claims 1
UDERFTNWMWSEFW-LLVKDONJSA-N 5-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(2-methylpropyl)pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC(C)C)=C1 UDERFTNWMWSEFW-LLVKDONJSA-N 0.000 claims 1
OQFQXILBUZIEGF-OAHLLOKOSA-N 5-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(2-phenylethyl)pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCCC=2C=CC=CC=2)=C1 OQFQXILBUZIEGF-OAHLLOKOSA-N 0.000 claims 1
HHYIGAGBKDMOQO-SNVBAGLBSA-N 5-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-(4,4,4-trifluorobutyl)pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCCCC(F)(F)F)=C1 HHYIGAGBKDMOQO-SNVBAGLBSA-N 0.000 claims 1
GUPYTDXUAWYPQU-UKRRQHHQSA-N 5-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r)-1-phenylethyl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(N[C@H](C)C=2C=CC=CC=2)=C1 GUPYTDXUAWYPQU-UKRRQHHQSA-N 0.000 claims 1
HQUQZTFSTDAGRP-ZQQZQOJVSA-N 5-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(1r,3s,4s,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridazin-3-amine Chemical compound N([C@@H]1[C@@H](C)[C@@]2(C[C@](C1)(C2(C)C)[H])[H])C(N=NC=1)=CC=1N1CC[C@@H](NC)C1 HQUQZTFSTDAGRP-ZQQZQOJVSA-N 0.000 claims 1
VMHNCPDQCIQIRN-OAHLLOKOSA-N 5-[(3r)-3-(methylamino)pyrrolidin-1-yl]-n-[(4-methylphenyl)methyl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC=2C=CC(C)=CC=2)=C1 VMHNCPDQCIQIRN-OAHLLOKOSA-N 0.000 claims 1
UUYQQIFKCXKZTA-SNVBAGLBSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(2,2-dimethylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)(C)C)=CC(N2C[C@H](N)CC2)=C1 UUYQQIFKCXKZTA-SNVBAGLBSA-N 0.000 claims 1
BRZAJFBRWPNASH-SECBINFHSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(2-methoxyethyl)pyridazin-3-amine Chemical compound N1=NC(NCCOC)=CC(N2C[C@H](N)CC2)=C1 BRZAJFBRWPNASH-SECBINFHSA-N 0.000 claims 1
TXNYEDFVFQUNGH-SNVBAGLBSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(2-methylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)C)=CC(N2C[C@H](N)CC2)=C1 TXNYEDFVFQUNGH-SNVBAGLBSA-N 0.000 claims 1
KOGDHBJVPMKXSG-CQSZACIVSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(2-phenylethyl)pyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCCC=2C=CC=CC=2)=C1 KOGDHBJVPMKXSG-CQSZACIVSA-N 0.000 claims 1
BQFYRGMWIRCYBO-SLDMJWGPSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(3-bicyclo[2.2.1]heptanylmethyl)pyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCC2C3CCC(C3)C2)=C1 BQFYRGMWIRCYBO-SLDMJWGPSA-N 0.000 claims 1
VUBBOLIUKUEIEI-GFCCVEGCSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(cyclopentylmethyl)pyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCC2CCCC2)=C1 VUBBOLIUKUEIEI-GFCCVEGCSA-N 0.000 claims 1
UIPIXOJOJVCBKW-SNVBAGLBSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(cyclopropylmethyl)pyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCC2CC2)=C1 UIPIXOJOJVCBKW-SNVBAGLBSA-N 0.000 claims 1
DMBCCWHSPHPEMB-LLVKDONJSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCC=2N=CC=CC=2)=C1 DMBCCWHSPHPEMB-LLVKDONJSA-N 0.000 claims 1
NJOITFGSDKYMBA-TZMCWYRMSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-[(1r)-1-phenylethyl]pyridazin-3-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=NC=1)=CC=1N1CC[C@@H](N)C1 NJOITFGSDKYMBA-TZMCWYRMSA-N 0.000 claims 1
LTJXSWAMNWQHGA-CYBMUJFWSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-[(4-fluorophenyl)methyl]pyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCC=2C=CC(F)=CC=2)=C1 LTJXSWAMNWQHGA-CYBMUJFWSA-N 0.000 claims 1
BVCVHDFXIMIRAP-CYBMUJFWSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-[(4-methoxyphenyl)methyl]pyridazin-3-amine Chemical compound C1=CC(OC)=CC=C1CNC1=CC(N2C[C@H](N)CC2)=CN=N1 BVCVHDFXIMIRAP-CYBMUJFWSA-N 0.000 claims 1
KGKCDGRBBJOFJS-CQSZACIVSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-[(4-methylphenyl)methyl]pyridazin-3-amine Chemical compound C1=CC(C)=CC=C1CNC1=CC(N2C[C@H](N)CC2)=CN=N1 KGKCDGRBBJOFJS-CQSZACIVSA-N 0.000 claims 1
DPDAMJGEGVJCRG-CYBMUJFWSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-benzylpyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NCC=2C=CC=CC=2)=C1 DPDAMJGEGVJCRG-CYBMUJFWSA-N 0.000 claims 1
KGUAKOJZXYPVBY-SNVBAGLBSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-butylpyridazin-3-amine Chemical compound N1=NC(NCCCC)=CC(N2C[C@H](N)CC2)=C1 KGUAKOJZXYPVBY-SNVBAGLBSA-N 0.000 claims 1
JXEHHMIXHKLLJJ-LLVKDONJSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclohexylpyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NC2CCCCC2)=C1 JXEHHMIXHKLLJJ-LLVKDONJSA-N 0.000 claims 1
URNXYHXVALXHGH-SNVBAGLBSA-N 5-[(3r)-3-aminopyrrolidin-1-yl]-n-cyclopentylpyridazin-3-amine Chemical compound C1[C@H](N)CCN1C1=CN=NC(NC2CCCC2)=C1 URNXYHXVALXHGH-SNVBAGLBSA-N 0.000 claims 1
UDERFTNWMWSEFW-NSHDSACASA-N 5-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(2-methylpropyl)pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC(C)C)=C1 UDERFTNWMWSEFW-NSHDSACASA-N 0.000 claims 1
HHYIGAGBKDMOQO-JTQLQIEISA-N 5-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(4,4,4-trifluorobutyl)pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCCCC(F)(F)F)=C1 HHYIGAGBKDMOQO-JTQLQIEISA-N 0.000 claims 1
IVOGNTTUTOJTBI-ZDUSSCGKSA-N 5-[(3s)-3-(methylamino)pyrrolidin-1-yl]-n-(pyridin-2-ylmethyl)pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC=2N=CC=CC=2)=C1 IVOGNTTUTOJTBI-ZDUSSCGKSA-N 0.000 claims 1
TXNYEDFVFQUNGH-JTQLQIEISA-N 5-[(3s)-3-aminopyrrolidin-1-yl]-n-(2-methylpropyl)pyridazin-3-amine Chemical compound N1=NC(NCC(C)C)=CC(N2C[C@@H](N)CC2)=C1 TXNYEDFVFQUNGH-JTQLQIEISA-N 0.000 claims 1
BQFYRGMWIRCYBO-XOZUOACSSA-N 5-[(3s)-3-aminopyrrolidin-1-yl]-n-(3-bicyclo[2.2.1]heptanylmethyl)pyridazin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CN=NC(NCC2C3CCC(C3)C2)=C1 BQFYRGMWIRCYBO-XOZUOACSSA-N 0.000 claims 1
VUBBOLIUKUEIEI-LBPRGKRZSA-N 5-[(3s)-3-aminopyrrolidin-1-yl]-n-(cyclopentylmethyl)pyridazin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CN=NC(NCC2CCCC2)=C1 VUBBOLIUKUEIEI-LBPRGKRZSA-N 0.000 claims 1
FPQBIXMQLINJQA-QMMMGPOBSA-N 5-[(3s)-3-aminopyrrolidin-1-yl]-n-cyclopropylpyridazin-3-amine Chemical compound C1[C@@H](N)CCN1C1=CN=NC(NC2CC2)=C1 FPQBIXMQLINJQA-QMMMGPOBSA-N 0.000 claims 1
QTNRBYAYMMTEGX-UHFFFAOYSA-N 5-[3-(methylamino)azetidin-1-yl]-n-(2-methylpropyl)pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCC(C)C)=C1 QTNRBYAYMMTEGX-UHFFFAOYSA-N 0.000 claims 1
SZERKLWLQVPGLP-UHFFFAOYSA-N 5-[3-(methylamino)azetidin-1-yl]-n-(4,4,4-trifluorobutyl)pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCCCC(F)(F)F)=C1 SZERKLWLQVPGLP-UHFFFAOYSA-N 0.000 claims 1
ZCXQOMMAIQFVIG-UHFFFAOYSA-N 5-[3-(methylamino)azetidin-1-yl]-n-(pyridin-2-ylmethyl)pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCC=2N=CC=CC=2)=C1 ZCXQOMMAIQFVIG-UHFFFAOYSA-N 0.000 claims 1
DWFOGLWBKKDYQU-MJVOBMLWSA-N 5-[3-(methylamino)azetidin-1-yl]-n-[(1r,5s)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]pyridazin-3-amine Chemical class CC([C@@]1(C[C@](C2)(C1(C)C)[H])[H])C2NC(N=NC=1)=CC=1N1CC(NC)C1 DWFOGLWBKKDYQU-MJVOBMLWSA-N 0.000 claims 1
QLMBEWNADHIWHO-UHFFFAOYSA-N 5-n-(2-aminoethyl)-3-n-(2,2-dimethylpropyl)-5-n-methylpyridazine-3,5-diamine Chemical compound NCCN(C)C1=CN=NC(NCC(C)(C)C)=C1 QLMBEWNADHIWHO-UHFFFAOYSA-N 0.000 claims 1
VXTSJHJLLDXDIV-UHFFFAOYSA-N 5-n-(2-aminoethyl)-3-n-(3-bicyclo[2.2.1]heptanyl)-5-n-methylpyridazine-3,5-diamine Chemical compound NCCN(C)C1=CN=NC(NC2C3CCC(C3)C2)=C1 VXTSJHJLLDXDIV-UHFFFAOYSA-N 0.000 claims 1
QZSUVDUZCIECLY-UHFFFAOYSA-N 5-n-(2-aminoethyl)-3-n-(cyclopentylmethyl)-5-n-methylpyridazine-3,5-diamine Chemical compound NCCN(C)C1=CN=NC(NCC2CCCC2)=C1 QZSUVDUZCIECLY-UHFFFAOYSA-N 0.000 claims 1
125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
NUJZNISZZFMSQB-UHFFFAOYSA-N n-(1-adamantyl)-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC23CC4CC(CC(C4)C2)C3)=C1 NUJZNISZZFMSQB-UHFFFAOYSA-N 0.000 claims 1
ZSNJJRDOZANNPT-VQBCORBOSA-N n-(1-adamantyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC23CC4CC(CC(C4)C2)C3)=C1 ZSNJJRDOZANNPT-VQBCORBOSA-N 0.000 claims 1
ZSNJJRDOZANNPT-FAKMSMKASA-N n-(1-adamantyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC23CC4CC(CC(C4)C2)C3)=C1 ZSNJJRDOZANNPT-FAKMSMKASA-N 0.000 claims 1
HQMCIWIVORZASE-BYQBSCIQSA-N n-(1-adamantyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1C1=CN=NC(NC23CC4CC(CC(C4)C2)C3)=C1 HQMCIWIVORZASE-BYQBSCIQSA-N 0.000 claims 1
HQMCIWIVORZASE-OHEAZXOVSA-N n-(1-adamantyl)-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1C1=CN=NC(NC23CC4CC(CC(C4)C2)C3)=C1 HQMCIWIVORZASE-OHEAZXOVSA-N 0.000 claims 1
OYFQSOGYBGQXLH-UHFFFAOYSA-N n-(1-adamantylmethyl)-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC23CC4CC(CC(C4)C2)C3)=C1 OYFQSOGYBGQXLH-UHFFFAOYSA-N 0.000 claims 1
FPEZPUOKMWVKBA-IGDKPHCXSA-N n-(1-adamantylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC23CC4CC(CC(C4)C2)C3)=C1 FPEZPUOKMWVKBA-IGDKPHCXSA-N 0.000 claims 1
FPEZPUOKMWVKBA-QQABJKMWSA-N n-(1-adamantylmethyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC23CC4CC(CC(C4)C2)C3)=C1 FPEZPUOKMWVKBA-QQABJKMWSA-N 0.000 claims 1
MKYNWNRLISLMSH-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC(C)(C)C)=N1 MKYNWNRLISLMSH-UHFFFAOYSA-N 0.000 claims 1
OPIQDPJVLXNEJR-GFCCVEGCSA-N n-(2,2-dimethylpropyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC(C)(C)C)=C1 OPIQDPJVLXNEJR-GFCCVEGCSA-N 0.000 claims 1
ZZPQCQWVWDUPSI-LLVKDONJSA-N n-(2,2-dimethylpropyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC(C)(C)C)=N1 ZZPQCQWVWDUPSI-LLVKDONJSA-N 0.000 claims 1
ZZPQCQWVWDUPSI-NSHDSACASA-N n-(2,2-dimethylpropyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC(C)(C)C)=N1 ZZPQCQWVWDUPSI-NSHDSACASA-N 0.000 claims 1
MRVWJRIQMZIMNY-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound CC(C)(C)CNC1=NC=CC(N2CCNCC2)=N1 MRVWJRIQMZIMNY-UHFFFAOYSA-N 0.000 claims 1
QBBFMKPAYRCLPC-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-5-(4-methylpiperazin-1-yl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CN=NC(NCC(C)(C)C)=C1 QBBFMKPAYRCLPC-UHFFFAOYSA-N 0.000 claims 1
OIXAZLBXUXELOS-LLVKDONJSA-N n-(2,2-dimethylpropyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC(C)(C)C)=C1 OIXAZLBXUXELOS-LLVKDONJSA-N 0.000 claims 1
OIXAZLBXUXELOS-NSHDSACASA-N n-(2,2-dimethylpropyl)-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC(C)(C)C)=C1 OIXAZLBXUXELOS-NSHDSACASA-N 0.000 claims 1
ZKOWXTVHLNSIRO-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCC(C)(C)C)=C1 ZKOWXTVHLNSIRO-UHFFFAOYSA-N 0.000 claims 1
AQFRFVCXISBJKG-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-5-piperazin-1-ylpyridazin-3-amine Chemical compound N1=NC(NCC(C)(C)C)=CC(N2CCNCC2)=C1 AQFRFVCXISBJKG-UHFFFAOYSA-N 0.000 claims 1
SPCVOQYRGOJHQR-UHFFFAOYSA-N n-(2-adamantyl)-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC2C3CC4CC(C3)CC2C4)=C1 SPCVOQYRGOJHQR-UHFFFAOYSA-N 0.000 claims 1
OCOWXBTWSNLBIN-XQYHGENGSA-N n-(2-adamantyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC2C3CC4CC(C3)CC2C4)=C1 OCOWXBTWSNLBIN-XQYHGENGSA-N 0.000 claims 1
OCOWXBTWSNLBIN-ITNKIWFMSA-N n-(2-adamantyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC2C3CC4CC(C3)CC2C4)=C1 OCOWXBTWSNLBIN-ITNKIWFMSA-N 0.000 claims 1
VPZRLVBRSWSGFF-SHKBMLEPSA-N n-(2-adamantyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1C1=CN=NC(NC2C3CC4CC(C3)CC2C4)=C1 VPZRLVBRSWSGFF-SHKBMLEPSA-N 0.000 claims 1
VPZRLVBRSWSGFF-WIXVZAKGSA-N n-(2-adamantyl)-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@@H](NC)CCN1C1=CN=NC(NC2C3CC4CC(C3)CC2C4)=C1 VPZRLVBRSWSGFF-WIXVZAKGSA-N 0.000 claims 1
QNUQBPOVDLSYRX-UHFFFAOYSA-N n-(2-methoxyethyl)-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1=NC(NCCOC)=CC(N2CCN(C)CC2)=C1 QNUQBPOVDLSYRX-UHFFFAOYSA-N 0.000 claims 1
MDYMALZCMJWQQE-UHFFFAOYSA-N n-(2-methoxyethyl)-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound COCCNC1=NC=CC(N2CCN(C)CC2)=N1 MDYMALZCMJWQQE-UHFFFAOYSA-N 0.000 claims 1
KPRUFKRDQSBXDR-LLVKDONJSA-N n-(2-methoxyethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCCOC)=C1 KPRUFKRDQSBXDR-LLVKDONJSA-N 0.000 claims 1
XNFBTAHGAJZYIN-SNVBAGLBSA-N n-(2-methoxyethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCCOC)=N1 XNFBTAHGAJZYIN-SNVBAGLBSA-N 0.000 claims 1
KPRUFKRDQSBXDR-NSHDSACASA-N n-(2-methoxyethyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCCOC)=C1 KPRUFKRDQSBXDR-NSHDSACASA-N 0.000 claims 1
XJJFRHFIJUIPRJ-UHFFFAOYSA-N n-(2-methoxyethyl)-4-[3-(methylamino)azetidin-1-yl]pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCCOC)=C1 XJJFRHFIJUIPRJ-UHFFFAOYSA-N 0.000 claims 1
QDKKKKGGHZJZMO-UHFFFAOYSA-N n-(2-methoxyethyl)-4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCCOC)=N1 QDKKKKGGHZJZMO-UHFFFAOYSA-N 0.000 claims 1
OUJZJYRNSKGYHF-UHFFFAOYSA-N n-(2-methoxyethyl)-4-piperazin-1-ylpyridin-2-amine Chemical compound C1=NC(NCCOC)=CC(N2CCNCC2)=C1 OUJZJYRNSKGYHF-UHFFFAOYSA-N 0.000 claims 1
MSEBFYWDQKIOEM-UHFFFAOYSA-N n-(2-methoxyethyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound COCCNC1=NC=CC(N2CCNCC2)=N1 MSEBFYWDQKIOEM-UHFFFAOYSA-N 0.000 claims 1
TZABPSDOIQXLMF-UHFFFAOYSA-N n-(2-methoxyethyl)-5-(4-methylpiperazin-1-yl)pyridazin-3-amine Chemical compound N1=NC(NCCOC)=CC(N2CCN(C)CC2)=C1 TZABPSDOIQXLMF-UHFFFAOYSA-N 0.000 claims 1
OLMDCLNAEFIAAG-SNVBAGLBSA-N n-(2-methoxyethyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCCOC)=C1 OLMDCLNAEFIAAG-SNVBAGLBSA-N 0.000 claims 1
OLMDCLNAEFIAAG-JTQLQIEISA-N n-(2-methoxyethyl)-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCCOC)=C1 OLMDCLNAEFIAAG-JTQLQIEISA-N 0.000 claims 1
DQCXMUOEQSHFNM-UHFFFAOYSA-N n-(2-methoxyethyl)-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCCOC)=C1 DQCXMUOEQSHFNM-UHFFFAOYSA-N 0.000 claims 1
OWYJWFDOOKMLSF-UHFFFAOYSA-N n-(2-methylpropyl)-4-piperazin-1-ylpyridin-2-amine Chemical compound C1=NC(NCC(C)C)=CC(N2CCNCC2)=C1 OWYJWFDOOKMLSF-UHFFFAOYSA-N 0.000 claims 1
HDAPAMWFKVMXKW-UHFFFAOYSA-N n-(2-methylpropyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound CC(C)CNC1=NC=CC(N2CCNCC2)=N1 HDAPAMWFKVMXKW-UHFFFAOYSA-N 0.000 claims 1
XKCUIXQGTMUHOB-UHFFFAOYSA-N n-(2-methylsulfanylethyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound CSCCNC1=NC=CC(N2CCNCC2)=N1 XKCUIXQGTMUHOB-UHFFFAOYSA-N 0.000 claims 1
DNYNNMUAEMVDJS-UHFFFAOYSA-N n-(2-phenylethyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound N=1C=CC(N2CCNCC2)=NC=1NCCC1=CC=CC=C1 DNYNNMUAEMVDJS-UHFFFAOYSA-N 0.000 claims 1
JYFDQHXGIPOHNG-UHFFFAOYSA-N n-(2-phenylethyl)-5-piperazin-1-ylpyridazin-3-amine Chemical compound C=1C(N2CCNCC2)=CN=NC=1NCCC1=CC=CC=C1 JYFDQHXGIPOHNG-UHFFFAOYSA-N 0.000 claims 1
FNLSLUQTMBZMEE-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-(1,4-diazepan-1-yl)pyridin-2-amine Chemical compound C1CC2CC1CC2NC(N=CC=1)=CC=1N1CCCNCC1 FNLSLUQTMBZMEE-UHFFFAOYSA-N 0.000 claims 1
IJFGETUFCFAEDO-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-(1,4-diazepan-1-yl)pyrimidin-2-amine Chemical compound C1CC2CC1CC2NC(N=1)=NC=CC=1N1CCCNCC1 IJFGETUFCFAEDO-UHFFFAOYSA-N 0.000 claims 1
IVFQODBYXHLMLR-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=N1 IVFQODBYXHLMLR-UHFFFAOYSA-N 0.000 claims 1
UNZZIPGSYLMDRE-SBVZSOIPSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=C1 UNZZIPGSYLMDRE-SBVZSOIPSA-N 0.000 claims 1
NZJVXVCSPDDULP-WCFLAILDSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=N1 NZJVXVCSPDDULP-WCFLAILDSA-N 0.000 claims 1
WGDVNAMQYXMAJQ-JNJRBNHSSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=C1 WGDVNAMQYXMAJQ-JNJRBNHSSA-N 0.000 claims 1
NZJVXVCSPDDULP-RFPFOJJUSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC2C3CCC(C3)C2)=N1 NZJVXVCSPDDULP-RFPFOJJUSA-N 0.000 claims 1
HYILOSFTALNHIK-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NC2C3CCC(C3)C2)=N1 HYILOSFTALNHIK-UHFFFAOYSA-N 0.000 claims 1
ODDFZMBCXMJJQX-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-(1,4-diazepan-1-yl)pyridazin-3-amine Chemical compound C1CC2CC1CC2NC(N=NC=1)=CC=1N1CCCNCC1 ODDFZMBCXMJJQX-UHFFFAOYSA-N 0.000 claims 1
QAXRJLAQFRQDQS-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-(4-methylpiperazin-1-yl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CN=NC(NC2C3CCC(C3)C2)=C1 QAXRJLAQFRQDQS-UHFFFAOYSA-N 0.000 claims 1
ACKWPAAIJCHTIB-PYYBWGNESA-N n-(3-bicyclo[2.2.1]heptanyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NC2C3CCC(C3)C2)=C1 ACKWPAAIJCHTIB-PYYBWGNESA-N 0.000 claims 1
ACKWPAAIJCHTIB-WRSKWOSUSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NC2C3CCC(C3)C2)=C1 ACKWPAAIJCHTIB-WRSKWOSUSA-N 0.000 claims 1
WXTSCNKQRKBOQP-UHFFFAOYSA-N n-(3-bicyclo[2.2.1]heptanyl)-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NC2C3CCC(C3)C2)=C1 WXTSCNKQRKBOQP-UHFFFAOYSA-N 0.000 claims 1
GKMXZHGBRJEESQ-LGGPCSOHSA-N n-(3-bicyclo[2.2.1]heptanylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC2C3CCC(C3)C2)=C1 GKMXZHGBRJEESQ-LGGPCSOHSA-N 0.000 claims 1
INYPXIANUGGEEN-MLGYPOCJSA-N n-(3-bicyclo[2.2.1]heptanylmethyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC2C3CCC(C3)C2)=C1 INYPXIANUGGEEN-MLGYPOCJSA-N 0.000 claims 1
INYPXIANUGGEEN-BOADVZGGSA-N n-(3-bicyclo[2.2.1]heptanylmethyl)-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC2C3CCC(C3)C2)=C1 INYPXIANUGGEEN-BOADVZGGSA-N 0.000 claims 1
PGMDSQKUIUCLOL-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC2CCCCC2)=C1 PGMDSQKUIUCLOL-UHFFFAOYSA-N 0.000 claims 1
VEKBSXAIEYAGSW-OAHLLOKOSA-N n-(cyclohexylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC2CCCCC2)=C1 VEKBSXAIEYAGSW-OAHLLOKOSA-N 0.000 claims 1
SUXXEXZIPKJONY-CQSZACIVSA-N n-(cyclohexylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC2CCCCC2)=N1 SUXXEXZIPKJONY-CQSZACIVSA-N 0.000 claims 1
VEKBSXAIEYAGSW-HNNXBMFYSA-N n-(cyclohexylmethyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC2CCCCC2)=C1 VEKBSXAIEYAGSW-HNNXBMFYSA-N 0.000 claims 1
VUUVWLCIEUCPDG-UHFFFAOYSA-N n-(cyclohexylmethyl)-4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC2CCCCC2)=N1 VUUVWLCIEUCPDG-UHFFFAOYSA-N 0.000 claims 1
WNACAFGPUNRMCO-CQSZACIVSA-N n-(cyclohexylmethyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC2CCCCC2)=C1 WNACAFGPUNRMCO-CQSZACIVSA-N 0.000 claims 1
WNACAFGPUNRMCO-AWEZNQCLSA-N n-(cyclohexylmethyl)-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC2CCCCC2)=C1 WNACAFGPUNRMCO-AWEZNQCLSA-N 0.000 claims 1
OBBDKTRQFPBRFX-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC2CCCC2)=C1 OBBDKTRQFPBRFX-UHFFFAOYSA-N 0.000 claims 1
SYGNAICWOYWMPX-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC2CCCC2)=N1 SYGNAICWOYWMPX-UHFFFAOYSA-N 0.000 claims 1
ASNFGXUCTAGINL-CQSZACIVSA-N n-(cyclopentylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC2CCCC2)=C1 ASNFGXUCTAGINL-CQSZACIVSA-N 0.000 claims 1
XYQSUZGSAAJUEB-CYBMUJFWSA-N n-(cyclopentylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC2CCCC2)=N1 XYQSUZGSAAJUEB-CYBMUJFWSA-N 0.000 claims 1
ASNFGXUCTAGINL-AWEZNQCLSA-N n-(cyclopentylmethyl)-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC2CCCC2)=C1 ASNFGXUCTAGINL-AWEZNQCLSA-N 0.000 claims 1
PLESHIVWLQHHAS-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-[3-(methylamino)azetidin-1-yl]pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC2CCCC2)=C1 PLESHIVWLQHHAS-UHFFFAOYSA-N 0.000 claims 1
GFMZSVWURMGHGA-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-piperazin-1-ylpyridin-2-amine Chemical compound C1CCCC1CNC(N=CC=1)=CC=1N1CCNCC1 GFMZSVWURMGHGA-UHFFFAOYSA-N 0.000 claims 1
AANJGWNIGDMXDX-UHFFFAOYSA-N n-(cyclopentylmethyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C1CCCC1CNC(N=1)=NC=CC=1N1CCNCC1 AANJGWNIGDMXDX-UHFFFAOYSA-N 0.000 claims 1
JVSZOVZMMWZCLH-UHFFFAOYSA-N n-(cyclopentylmethyl)-5-(1,4-diazepan-1-yl)pyridazin-3-amine Chemical compound C1CCCC1CNC(N=NC=1)=CC=1N1CCCNCC1 JVSZOVZMMWZCLH-UHFFFAOYSA-N 0.000 claims 1
FOGWEVHEURTTGH-UHFFFAOYSA-N n-(cyclopentylmethyl)-5-(4-methylpiperazin-1-yl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CN=NC(NCC2CCCC2)=C1 FOGWEVHEURTTGH-UHFFFAOYSA-N 0.000 claims 1
ILDWACKAYFWDNA-UHFFFAOYSA-N n-(cyclopentylmethyl)-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCC2CCCC2)=C1 ILDWACKAYFWDNA-UHFFFAOYSA-N 0.000 claims 1
ZUPSAZIJEVQXFO-UHFFFAOYSA-N n-(cyclopentylmethyl)-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1CCCC1CNC(N=NC=1)=CC=1N1CCNCC1 ZUPSAZIJEVQXFO-UHFFFAOYSA-N 0.000 claims 1
QOTNRPWYDFMVHQ-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC2CC2)=N1 QOTNRPWYDFMVHQ-UHFFFAOYSA-N 0.000 claims 1
IXWPEHPETMXXGE-CURYUGHLSA-N n-(cyclopropylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1[C@H](NC)CCN1C1=CC=NC(NCC2CC2)=C1 IXWPEHPETMXXGE-CURYUGHLSA-N 0.000 claims 1
XFYIGUHYBNCJKM-LLVKDONJSA-N n-(cyclopropylmethyl)-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC2CC2)=N1 XFYIGUHYBNCJKM-LLVKDONJSA-N 0.000 claims 1
UZLHBGZXOOPWEB-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-piperazin-1-ylpyridin-2-amine Chemical compound C1CC1CNC(N=CC=1)=CC=1N1CCNCC1 UZLHBGZXOOPWEB-UHFFFAOYSA-N 0.000 claims 1
WXWLLLPFQQBISE-UHFFFAOYSA-N n-(cyclopropylmethyl)-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C1CC1CNC(N=1)=NC=CC=1N1CCNCC1 WXWLLLPFQQBISE-UHFFFAOYSA-N 0.000 claims 1
OKCLNWPTVGLGIO-LLVKDONJSA-N n-(cyclopropylmethyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC2CC2)=C1 OKCLNWPTVGLGIO-LLVKDONJSA-N 0.000 claims 1
NVWULEXVHHFFHZ-UHFFFAOYSA-N n-(cyclopropylmethyl)-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCC2CC2)=C1 NVWULEXVHHFFHZ-UHFFFAOYSA-N 0.000 claims 1
FHKNJUJNLLCLOV-UHFFFAOYSA-N n-(cyclopropylmethyl)-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1CC1CNC(N=NC=1)=CC=1N1CCNCC1 FHKNJUJNLLCLOV-UHFFFAOYSA-N 0.000 claims 1
RVIZCVOTNCVBMC-GFCCVEGCSA-N n-(furan-3-ylmethyl)-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC2=COC=C2)=C1 RVIZCVOTNCVBMC-GFCCVEGCSA-N 0.000 claims 1
HZBAAHUNZUTCNI-UHFFFAOYSA-N n-(oxolan-2-ylmethyl)-4-piperazin-1-ylpyridin-2-amine Chemical compound C1CCOC1CNC(N=CC=1)=CC=1N1CCNCC1 HZBAAHUNZUTCNI-UHFFFAOYSA-N 0.000 claims 1
UCOTWNBYDDQGLV-OAHLLOKOSA-N n-[(1r)-1-cyclohexylethyl]-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound N([C@H](C)C1CCCCC1)C(N=CC=1)=CC=1N1CCN(C)CC1 UCOTWNBYDDQGLV-OAHLLOKOSA-N 0.000 claims 1
LJHOFYWGXSYWQI-GDBMZVCRSA-N n-[(1r)-1-cyclohexylethyl]-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(N[C@H](C)C2CCCCC2)=C1 LJHOFYWGXSYWQI-GDBMZVCRSA-N 0.000 claims 1
LJHOFYWGXSYWQI-ZBFHGGJFSA-N n-[(1r)-1-cyclohexylethyl]-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(N[C@H](C)C2CCCCC2)=C1 LJHOFYWGXSYWQI-ZBFHGGJFSA-N 0.000 claims 1
XOAYVJHOCXRDLX-GFCCVEGCSA-N n-[(1r)-1-cyclohexylethyl]-4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(N[C@H](C)C2CCCCC2)=N1 XOAYVJHOCXRDLX-GFCCVEGCSA-N 0.000 claims 1
PVPNFFBGQNNATK-UKRRQHHQSA-N n-[(1r)-1-cyclohexylethyl]-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(N[C@H](C)C2CCCCC2)=C1 PVPNFFBGQNNATK-UKRRQHHQSA-N 0.000 claims 1
PVPNFFBGQNNATK-HIFRSBDPSA-N n-[(1r)-1-cyclohexylethyl]-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(N[C@H](C)C2CCCCC2)=C1 PVPNFFBGQNNATK-HIFRSBDPSA-N 0.000 claims 1
NDQFQCMPGLOPIQ-CYBMUJFWSA-N n-[(1r)-1-phenylethyl]-5-piperazin-1-ylpyridazin-3-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=NC=1)=CC=1N1CCNCC1 NDQFQCMPGLOPIQ-CYBMUJFWSA-N 0.000 claims 1
MGNNTZCPCJESKH-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=C1 MGNNTZCPCJESKH-UHFFFAOYSA-N 0.000 claims 1
HOHXXBGSTKDJOH-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=N1 HOHXXBGSTKDJOH-UHFFFAOYSA-N 0.000 claims 1
YRHSQZZTGGRBDO-QCUBGVIVSA-N n-[(4-fluorophenyl)methyl]-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=C1 YRHSQZZTGGRBDO-QCUBGVIVSA-N 0.000 claims 1
LVGMNEWIDAHWCY-CQSZACIVSA-N n-[(4-fluorophenyl)methyl]-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=N1 LVGMNEWIDAHWCY-CQSZACIVSA-N 0.000 claims 1
QIKKIPDUTBSDFG-HNNXBMFYSA-N n-[(4-fluorophenyl)methyl]-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=C1 QIKKIPDUTBSDFG-HNNXBMFYSA-N 0.000 claims 1
BJMDRYCQEHYSTQ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[3-(methylamino)azetidin-1-yl]pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=C1 BJMDRYCQEHYSTQ-UHFFFAOYSA-N 0.000 claims 1
JBLQLUZSATWYRP-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC=2C=CC(F)=CC=2)=N1 JBLQLUZSATWYRP-UHFFFAOYSA-N 0.000 claims 1
IZPDUYKVJZFDRR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-piperazin-1-ylpyridin-2-amine Chemical compound C1=CC(F)=CC=C1CNC1=CC(N2CCNCC2)=CC=N1 IZPDUYKVJZFDRR-UHFFFAOYSA-N 0.000 claims 1
XUBUPISXNHFNNZ-CQSZACIVSA-N n-[(4-fluorophenyl)methyl]-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC=2C=CC(F)=CC=2)=C1 XUBUPISXNHFNNZ-CQSZACIVSA-N 0.000 claims 1
XUBUPISXNHFNNZ-AWEZNQCLSA-N n-[(4-fluorophenyl)methyl]-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC=2C=CC(F)=CC=2)=C1 XUBUPISXNHFNNZ-AWEZNQCLSA-N 0.000 claims 1
CAQPOUUEWMPIGV-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1=CC(F)=CC=C1CNC1=CC(N2CCNCC2)=CN=N1 CAQPOUUEWMPIGV-UHFFFAOYSA-N 0.000 claims 1
KUQLDHKHFMETPB-CQSZACIVSA-N n-[(4-methoxyphenyl)methyl]-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC=2C=CC(OC)=CC=2)=N1 KUQLDHKHFMETPB-CQSZACIVSA-N 0.000 claims 1
BFCGKEGQDOETMJ-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NC=CC(N2CCNCC2)=N1 BFCGKEGQDOETMJ-UHFFFAOYSA-N 0.000 claims 1
FDNNYBRLBKTLOP-CQSZACIVSA-N n-[(4-methoxyphenyl)methyl]-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC=2C=CC(OC)=CC=2)=C1 FDNNYBRLBKTLOP-CQSZACIVSA-N 0.000 claims 1
SJWVTGVVZLIIIC-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1=CC(OC)=CC=C1CNC1=CC(N2CCNCC2)=CN=N1 SJWVTGVVZLIIIC-UHFFFAOYSA-N 0.000 claims 1
INZGJKXYCLXKFZ-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC=2C=CC(C)=CC=2)=N1 INZGJKXYCLXKFZ-UHFFFAOYSA-N 0.000 claims 1
LNVYVURUGPIOCZ-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C1=CC(C)=CC=C1CNC1=NC=CC(N2CCNCC2)=N1 LNVYVURUGPIOCZ-UHFFFAOYSA-N 0.000 claims 1
ZRDZDHJXAIVZBR-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1=CC(C)=CC=C1CNC1=CC(N2CCNCC2)=CN=N1 ZRDZDHJXAIVZBR-UHFFFAOYSA-N 0.000 claims 1
ZAQOQQVSEAOPRO-UHFFFAOYSA-N n-[(6,6-dimethyl-4-bicyclo[3.1.1]heptanyl)methyl]-4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC2C3CC(C3(C)C)CC2)=N1 ZAQOQQVSEAOPRO-UHFFFAOYSA-N 0.000 claims 1
VGUSEASWPRWZDI-UKEPKTAJSA-N n-[(6,6-dimethyl-4-bicyclo[3.1.1]heptanyl)methyl]-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC2C3CC(C3(C)C)CC2)=C1 VGUSEASWPRWZDI-UKEPKTAJSA-N 0.000 claims 1
VGUSEASWPRWZDI-LETWWHAPSA-N n-[(6,6-dimethyl-4-bicyclo[3.1.1]heptanyl)methyl]-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NCC2C3CC(C3(C)C)CC2)=C1 VGUSEASWPRWZDI-LETWWHAPSA-N 0.000 claims 1
DVQFUGNOIPFJGD-RYRKJORJSA-N n-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical class C([C@@H]1[C@@]2(C[C@](CC1)(C2(C)C)[H])[H])NC(N=CC=1)=CC=1N1CCN(C)CC1 DVQFUGNOIPFJGD-RYRKJORJSA-N 0.000 claims 1
IGQIIUYYHPMBGK-QXSJWSMHSA-N n-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C([C@@H]1[C@@]2(C[C@](CC1)(C2(C)C)[H])[H])NC(N=1)=NC=CC=1N1CC[C@@H](NC)C1 IGQIIUYYHPMBGK-QXSJWSMHSA-N 0.000 claims 1
KHDJETBIAHBJSZ-CVYDXHPNSA-N n-[[(1s,4s,5s)-6,6-dimethyl-4-bicyclo[3.1.1]heptanyl]methyl]-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C([C@@H]1[C@@]2(C[C@](CC1)(C2(C)C)[H])[H])NC(N=CC=1)=CC=1N1CC[C@H](NC)C1 KHDJETBIAHBJSZ-CVYDXHPNSA-N 0.000 claims 1
FSFKGNPFUGKXLM-LLVKDONJSA-N n-[[(2r)-oxolan-2-yl]methyl]-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C([C@@H]1OCCC1)NC(N=1)=NC=CC=1N1CCNCC1 FSFKGNPFUGKXLM-LLVKDONJSA-N 0.000 claims 1
AVRFTBJJEHCANX-UHFFFAOYSA-N n-benzyl-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NCC=2C=CC=CC=2)=N1 AVRFTBJJEHCANX-UHFFFAOYSA-N 0.000 claims 1
FAQTUDDRRFDJAH-OAHLLOKOSA-N n-benzyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC=2C=CC=CC=2)=C1 FAQTUDDRRFDJAH-OAHLLOKOSA-N 0.000 claims 1
HNBFXGULFYXJSQ-CQSZACIVSA-N n-benzyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NCC=2C=CC=CC=2)=N1 HNBFXGULFYXJSQ-CQSZACIVSA-N 0.000 claims 1
FAQTUDDRRFDJAH-HNNXBMFYSA-N n-benzyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC=2C=CC=CC=2)=C1 FAQTUDDRRFDJAH-HNNXBMFYSA-N 0.000 claims 1
HNBFXGULFYXJSQ-AWEZNQCLSA-N n-benzyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NCC=2C=CC=CC=2)=N1 HNBFXGULFYXJSQ-AWEZNQCLSA-N 0.000 claims 1
RBPJCXGCTIPLQQ-UHFFFAOYSA-N n-benzyl-4-[3-(methylamino)azetidin-1-yl]pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NCC=2C=CC=CC=2)=C1 RBPJCXGCTIPLQQ-UHFFFAOYSA-N 0.000 claims 1
AERARUKCPQWTEU-UHFFFAOYSA-N n-benzyl-4-piperazin-1-ylpyridin-2-amine Chemical compound C=1C=CC=CC=1CNC(N=CC=1)=CC=1N1CCNCC1 AERARUKCPQWTEU-UHFFFAOYSA-N 0.000 claims 1
SGUBXKWIXLLZPM-UHFFFAOYSA-N n-benzyl-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C=1C=CC=CC=1CNC(N=1)=NC=CC=1N1CCNCC1 SGUBXKWIXLLZPM-UHFFFAOYSA-N 0.000 claims 1
AEQNUWCYVHVRRG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CN=NC(NCC=2C=CC=CC=2)=C1 AEQNUWCYVHVRRG-UHFFFAOYSA-N 0.000 claims 1
MOSCUYQIWFVMBQ-CQSZACIVSA-N n-benzyl-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NCC=2C=CC=CC=2)=C1 MOSCUYQIWFVMBQ-CQSZACIVSA-N 0.000 claims 1
VSDPLCKKWUGKIW-UHFFFAOYSA-N n-benzyl-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NCC=2C=CC=CC=2)=C1 VSDPLCKKWUGKIW-UHFFFAOYSA-N 0.000 claims 1
OHVBODJYDJFBCK-UHFFFAOYSA-N n-benzyl-5-piperazin-1-ylpyridazin-3-amine Chemical compound C=1C=CC=CC=1CNC(N=NC=1)=CC=1N1CCNCC1 OHVBODJYDJFBCK-UHFFFAOYSA-N 0.000 claims 1
QLBSQTJGCWXOKH-UHFFFAOYSA-N n-butyl-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(N2CCN(C)CC2)=N1 QLBSQTJGCWXOKH-UHFFFAOYSA-N 0.000 claims 1
FMAHIXYZGXPWMZ-LLVKDONJSA-N n-butyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(N2C[C@@H](CC2)NC)=N1 FMAHIXYZGXPWMZ-LLVKDONJSA-N 0.000 claims 1
LXTSAPHWFHGYGW-LBPRGKRZSA-N n-butyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1=NC(NCCCC)=CC(N2C[C@H](CC2)NC)=C1 LXTSAPHWFHGYGW-LBPRGKRZSA-N 0.000 claims 1
CYURRULFWMNYCD-UHFFFAOYSA-N n-butyl-4-piperazin-1-ylpyridin-2-amine Chemical compound C1=NC(NCCCC)=CC(N2CCNCC2)=C1 CYURRULFWMNYCD-UHFFFAOYSA-N 0.000 claims 1
LMGIKPFGVTXTIL-UHFFFAOYSA-N n-butyl-4-piperazin-1-ylpyrimidin-2-amine Chemical compound CCCCNC1=NC=CC(N2CCNCC2)=N1 LMGIKPFGVTXTIL-UHFFFAOYSA-N 0.000 claims 1
POUWOKAIFUGAOQ-LLVKDONJSA-N n-butyl-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound N1=NC(NCCCC)=CC(N2C[C@@H](CC2)NC)=C1 POUWOKAIFUGAOQ-LLVKDONJSA-N 0.000 claims 1
OKNUZJGCFLNZFG-UHFFFAOYSA-N n-butyl-5-piperazin-1-ylpyridazin-3-amine Chemical compound N1=NC(NCCCC)=CC(N2CCNCC2)=C1 OKNUZJGCFLNZFG-UHFFFAOYSA-N 0.000 claims 1
OLCSLRNVQMMCKV-UHFFFAOYSA-N n-cyclobutyl-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC2CCC2)=N1 OLCSLRNVQMMCKV-UHFFFAOYSA-N 0.000 claims 1
FZXDVCNSEYZZOS-CYBMUJFWSA-N n-cyclohexyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC2CCCCC2)=N1 FZXDVCNSEYZZOS-CYBMUJFWSA-N 0.000 claims 1
UOTQMIOCKSVCTP-CYBMUJFWSA-N n-cyclohexyl-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NC2CCCCC2)=C1 UOTQMIOCKSVCTP-CYBMUJFWSA-N 0.000 claims 1
NKAVJPGQDCNDET-UHFFFAOYSA-N n-cyclohexyl-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NC2CCCCC2)=C1 NKAVJPGQDCNDET-UHFFFAOYSA-N 0.000 claims 1
OXTPRPCOUQQSDT-UHFFFAOYSA-N n-cyclohexyl-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1CCCCC1NC1=CC(N2CCNCC2)=CN=N1 OXTPRPCOUQQSDT-UHFFFAOYSA-N 0.000 claims 1
XBACZLKOADGICX-UHFFFAOYSA-N n-cyclopentyl-4-(4-methylpiperazin-1-yl)pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC2CCCC2)=C1 XBACZLKOADGICX-UHFFFAOYSA-N 0.000 claims 1
YESREZYFRANQPJ-UHFFFAOYSA-N n-cyclopentyl-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC2CCCC2)=N1 YESREZYFRANQPJ-UHFFFAOYSA-N 0.000 claims 1
FYWWTWHYFTWIRD-CYBMUJFWSA-N n-cyclopentyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC2CCCC2)=C1 FYWWTWHYFTWIRD-CYBMUJFWSA-N 0.000 claims 1
OKIQJSAUFFVQPX-GFCCVEGCSA-N n-cyclopentyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC2CCCC2)=N1 OKIQJSAUFFVQPX-GFCCVEGCSA-N 0.000 claims 1
FYWWTWHYFTWIRD-ZDUSSCGKSA-N n-cyclopentyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC2CCCC2)=C1 FYWWTWHYFTWIRD-ZDUSSCGKSA-N 0.000 claims 1
OKIQJSAUFFVQPX-LBPRGKRZSA-N n-cyclopentyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC2CCCC2)=N1 OKIQJSAUFFVQPX-LBPRGKRZSA-N 0.000 claims 1
RVFPTQKSPQETCM-UHFFFAOYSA-N n-cyclopentyl-4-[3-(methylamino)azetidin-1-yl]pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NC2CCCC2)=C1 RVFPTQKSPQETCM-UHFFFAOYSA-N 0.000 claims 1
XVYNDQAUNOCMHK-UHFFFAOYSA-N n-cyclopentyl-4-[3-(methylamino)azetidin-1-yl]pyrimidin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NC2CCCC2)=N1 XVYNDQAUNOCMHK-UHFFFAOYSA-N 0.000 claims 1
PLCYKYHRGPJQEW-UHFFFAOYSA-N n-cyclopentyl-4-piperazin-1-ylpyridin-2-amine Chemical compound C1CCCC1NC1=CC(N2CCNCC2)=CC=N1 PLCYKYHRGPJQEW-UHFFFAOYSA-N 0.000 claims 1
QNDXNUMACXEGBZ-UHFFFAOYSA-N n-cyclopentyl-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C1CCCC1NC1=NC=CC(N2CCNCC2)=N1 QNDXNUMACXEGBZ-UHFFFAOYSA-N 0.000 claims 1
HSUNYEWDALOZSK-UHFFFAOYSA-N n-cyclopentyl-5-(4-methylpiperazin-1-yl)pyridazin-3-amine Chemical compound C1CN(C)CCN1C1=CN=NC(NC2CCCC2)=C1 HSUNYEWDALOZSK-UHFFFAOYSA-N 0.000 claims 1
QLDXTDXXBCKZJH-GFCCVEGCSA-N n-cyclopentyl-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NC2CCCC2)=C1 QLDXTDXXBCKZJH-GFCCVEGCSA-N 0.000 claims 1
QLDXTDXXBCKZJH-LBPRGKRZSA-N n-cyclopentyl-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NC2CCCC2)=C1 QLDXTDXXBCKZJH-LBPRGKRZSA-N 0.000 claims 1
VIHSRSKDQNABTB-UHFFFAOYSA-N n-cyclopentyl-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NC2CCCC2)=C1 VIHSRSKDQNABTB-UHFFFAOYSA-N 0.000 claims 1
YYHITZHSZMIVAE-UHFFFAOYSA-N n-cyclopentyl-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1CCCC1NC1=CC(N2CCNCC2)=CN=N1 YYHITZHSZMIVAE-UHFFFAOYSA-N 0.000 claims 1
YBJSEWYUEJRJCQ-UHFFFAOYSA-N n-cyclopropyl-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=CC=NC(NC2CC2)=N1 YBJSEWYUEJRJCQ-UHFFFAOYSA-N 0.000 claims 1
GNRPIXUGRUHEAY-NVJADKKVSA-N n-cyclopropyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1[C@H](NC)CCN1C1=CC=NC(NC2CC2)=C1 GNRPIXUGRUHEAY-NVJADKKVSA-N 0.000 claims 1
LZABSKVJZGMKQU-SNVBAGLBSA-N n-cyclopropyl-4-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@H](NC)CCN1C1=CC=NC(NC2CC2)=N1 LZABSKVJZGMKQU-SNVBAGLBSA-N 0.000 claims 1
PRJGDLNVUAJQRM-NSHDSACASA-N n-cyclopropyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC2CC2)=C1 PRJGDLNVUAJQRM-NSHDSACASA-N 0.000 claims 1
LZABSKVJZGMKQU-JTQLQIEISA-N n-cyclopropyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyrimidin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC2CC2)=N1 LZABSKVJZGMKQU-JTQLQIEISA-N 0.000 claims 1
XWPCNGBXQBJHHM-UHFFFAOYSA-N n-cyclopropyl-4-[3-(methylamino)azetidin-1-yl]pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NC2CC2)=C1 XWPCNGBXQBJHHM-UHFFFAOYSA-N 0.000 claims 1
ZIXWJOSJOMVIRG-UHFFFAOYSA-N n-cyclopropyl-4-piperazin-1-ylpyrimidin-2-amine Chemical compound C1CC1NC1=NC=CC(N2CCNCC2)=N1 ZIXWJOSJOMVIRG-UHFFFAOYSA-N 0.000 claims 1
CHUZWQOIKJAOGH-SNVBAGLBSA-N n-cyclopropyl-5-[(3r)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@H](NC)CCN1C1=CN=NC(NC2CC2)=C1 CHUZWQOIKJAOGH-SNVBAGLBSA-N 0.000 claims 1
CHUZWQOIKJAOGH-JTQLQIEISA-N n-cyclopropyl-5-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridazin-3-amine Chemical compound C1[C@@H](NC)CCN1C1=CN=NC(NC2CC2)=C1 CHUZWQOIKJAOGH-JTQLQIEISA-N 0.000 claims 1
NACXUAUENXAYMQ-UHFFFAOYSA-N n-cyclopropyl-5-[3-(methylamino)azetidin-1-yl]pyridazin-3-amine Chemical compound C1C(NC)CN1C1=CN=NC(NC2CC2)=C1 NACXUAUENXAYMQ-UHFFFAOYSA-N 0.000 claims 1
XFNFGISWRBRFJF-UHFFFAOYSA-N n-cyclopropyl-5-piperazin-1-ylpyridazin-3-amine Chemical compound C1CC1NC1=CC(N2CCNCC2)=CN=N1 XFNFGISWRBRFJF-UHFFFAOYSA-N 0.000 claims 1
QJNDZTXTSPPVAM-UHFFFAOYSA-N n-phenyl-4-piperazin-1-ylpyridin-2-amine Chemical compound C1CNCCN1C1=CC=NC(NC=2C=CC=CC=2)=C1 QJNDZTXTSPPVAM-UHFFFAOYSA-N 0.000 claims 1
YLWIKUFSEARYHJ-NSHDSACASA-N n-tert-butyl-4-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridin-2-amine Chemical compound C1[C@@H](NC)CCN1C1=CC=NC(NC(C)(C)C)=C1 YLWIKUFSEARYHJ-NSHDSACASA-N 0.000 claims 1
HPRVXQDCTCTNJI-UHFFFAOYSA-N n-tert-butyl-4-[3-(methylamino)azetidin-1-yl]pyridin-2-amine Chemical compound C1C(NC)CN1C1=CC=NC(NC(C)(C)C)=C1 HPRVXQDCTCTNJI-UHFFFAOYSA-N 0.000 claims 1
LETVJWLLIMJADE-UHFFFAOYSA-N pyridazin-3-amine Chemical compound NC1=CC=CN=N1 LETVJWLLIMJADE-UHFFFAOYSA-N 0.000 claims 1
0 C*(*)C1C*(C)(C)CC1 Chemical compound C*(*)C1C*(C)(C)CC1 0.000 description 7

JP2011513686A 2008-06-12 2009-06-11 ヒスタミンｈ４受容体のジアミノピリジン、ピリミジン、及びピリダジンモジュレーター Expired - Fee Related JP5658662B2 (ja)