AU2004257260A1 - Substituted heterocyclic diarylamine analogues - Google Patents

Info

Publication number

AU2004257260A1

AU2004257260A1 AU2004257260A AU2004257260A AU2004257260A1 AU 2004257260 A1 AU2004257260 A1 AU 2004257260A1 AU 2004257260 A AU2004257260 A AU 2004257260A AU 2004257260 A AU2004257260 A AU 2004257260A AU 2004257260 A1 AU2004257260 A1 AU 2004257260A1

Authority

AU

Australia

Prior art keywords

alkyl

pharmaceutically acceptable

phenyl

acceptable form

compound

Prior art date

2003-07-10

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.)

Abandoned

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims description 348
• -1 hydroxy, amino Chemical group 0.000 claims description 210
• 229910052736 halogen Inorganic materials 0.000 claims description 123
• 150000002367 halogens Chemical class 0.000 claims description 122
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 113
• 108010062740 TRPV Cation Channels Proteins 0.000 claims description 109
• 102000011040 TRPV Cation Channels Human genes 0.000 claims description 108
• 125000000217 alkyl group Chemical group 0.000 claims description 108
• 125000001424 substituent group Chemical group 0.000 claims description 108
• 208000002193 Pain Diseases 0.000 claims description 98
• 230000036407 pain Effects 0.000 claims description 91
• 229910052739 hydrogen Inorganic materials 0.000 claims description 83
• 239000001257 hydrogen Substances 0.000 claims description 83
• YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 81
• 238000000034 method Methods 0.000 claims description 79
• 210000004027 cell Anatomy 0.000 claims description 76
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 74
• 239000000203 mixture Substances 0.000 claims description 72
• 230000000694 effects Effects 0.000 claims description 64
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
• 238000003556 assay Methods 0.000 claims description 56
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 48
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 40
• 125000004043 oxo group Chemical group O=* 0.000 claims description 39
• 229960002504 capsaicin Drugs 0.000 claims description 38
• 235000017663 capsaicin Nutrition 0.000 claims description 38
• 238000009739 binding Methods 0.000 claims description 37
• 230000027455 binding Effects 0.000 claims description 35
• 241001465754 Metazoa Species 0.000 claims description 34
• 239000000556 agonist Substances 0.000 claims description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 32
• 239000003446 ligand Substances 0.000 claims description 31
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 31
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 208000004296 neuralgia Diseases 0.000 claims description 28
• 238000000338 in vitro Methods 0.000 claims description 24
• 238000001727 in vivo Methods 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 19
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
• 208000003251 Pruritus Diseases 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 15
• 241000282414 Homo sapiens Species 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 239000011575 calcium Substances 0.000 claims description 15
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
• 206010046543 Urinary incontinence Diseases 0.000 claims description 14
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 13
• 229910052791 calcium Inorganic materials 0.000 claims description 13
• 208000021722 neuropathic pain Diseases 0.000 claims description 13
• 206010020853 Hypertonic bladder Diseases 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 claims description 12
• 208000009722 Overactive Urinary Bladder Diseases 0.000 claims description 11
• 208000020629 overactive bladder Diseases 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 206010011224 Cough Diseases 0.000 claims description 10
• 208000031361 Hiccup Diseases 0.000 claims description 10
• 206010029240 Neuritis Diseases 0.000 claims description 10
• 125000002837 carbocyclic group Chemical group 0.000 claims description 10
• 208000014674 injury Diseases 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 229910052786 argon Inorganic materials 0.000 claims description 7
• 238000001514 detection method Methods 0.000 claims description 7
• IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 claims description 7
• 239000003491 tear gas Substances 0.000 claims description 7
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
• 210000004369 blood Anatomy 0.000 claims description 6
• 239000008280 blood Substances 0.000 claims description 6
• 210000001124 body fluid Anatomy 0.000 claims description 6
• 239000010839 body fluid Substances 0.000 claims description 6
• 230000001413 cellular effect Effects 0.000 claims description 6
• 239000006071 cream Substances 0.000 claims description 6
• 238000000099 in vitro assay Methods 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 210000002569 neuron Anatomy 0.000 claims description 6
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 6
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 239000007789 gas Substances 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 230000007794 irritation Effects 0.000 claims description 5
• 201000001119 neuropathy Diseases 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 239000007921 spray Substances 0.000 claims description 5
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 208000008035 Back Pain Diseases 0.000 claims description 4
• 235000002566 Capsicum Nutrition 0.000 claims description 4
• 206010019233 Headaches Diseases 0.000 claims description 4
• 239000006002 Pepper Substances 0.000 claims description 4
• 235000016761 Piper aduncum Nutrition 0.000 claims description 4
• 235000017804 Piper guineense Nutrition 0.000 claims description 4
• 235000008184 Piper nigrum Nutrition 0.000 claims description 4
• 230000008484 agonism Effects 0.000 claims description 4
• 231100000869 headache Toxicity 0.000 claims description 4
• 230000000968 intestinal effect Effects 0.000 claims description 4
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
• 230000007823 neuropathy Effects 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 230000008733 trauma Effects 0.000 claims description 4
• 230000004580 weight loss Effects 0.000 claims description 4
• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 206010006482 Bronchospasm Diseases 0.000 claims description 3
• 206010068065 Burning mouth syndrome Diseases 0.000 claims description 3
• 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims description 3
• 208000001640 Fibromyalgia Diseases 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 208000019695 Migraine disease Diseases 0.000 claims description 3
• 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 claims description 3
• 239000000809 air pollutant Substances 0.000 claims description 3
• 231100001243 air pollutant Toxicity 0.000 claims description 3
• 208000006673 asthma Diseases 0.000 claims description 3
• 230000007885 bronchoconstriction Effects 0.000 claims description 3
• 239000002775 capsule Substances 0.000 claims description 3
• 208000004967 femoral neuropathy Diseases 0.000 claims description 3
• 239000012530 fluid Substances 0.000 claims description 3
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 3
• 208000032184 meralgia paresthetica Diseases 0.000 claims description 3
• UBTVSVNOSQWUMQ-UHFFFAOYSA-N n-(3,4-difluorophenyl)-2-(methoxymethyl)-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]pyrimidin-4-amine Chemical compound C=1C(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=NC(COC)=NC=1NC1=CC=C(F)C(F)=C1 UBTVSVNOSQWUMQ-UHFFFAOYSA-N 0.000 claims description 3
• ULHGSBJTWLEDNM-UHFFFAOYSA-N n-(4-fluorophenyl)-2-morpholin-4-yl-6-(4-pyridin-2-ylpiperazin-1-yl)pyrimidin-4-amine Chemical compound C1=CC(F)=CC=C1NC1=CC(N2CCN(CC2)C=2N=CC=CC=2)=NC(N2CCOCC2)=N1 ULHGSBJTWLEDNM-UHFFFAOYSA-N 0.000 claims description 3
• 230000001737 promoting effect Effects 0.000 claims description 3
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 208000004371 toothache Diseases 0.000 claims description 3
• HYZBAROPDBRUIR-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n,4-n-diethyl-2-n-(4-fluorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(CC)CC)=NC=1NC1=CC=C(F)C=C1 HYZBAROPDBRUIR-UHFFFAOYSA-N 0.000 claims description 2
• 208000030507 AIDS Diseases 0.000 claims description 2
• 208000001387 Causalgia Diseases 0.000 claims description 2
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
• 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 2
• 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 2
• 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 2
• 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 2
• 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 2
• 208000004983 Phantom Limb Diseases 0.000 claims description 2
• 206010056238 Phantom pain Diseases 0.000 claims description 2
• 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 2
• 239000000443 aerosol Substances 0.000 claims description 2
• 230000002146 bilateral effect Effects 0.000 claims description 2
• 208000014439 complex regional pain syndrome type 2 Diseases 0.000 claims description 2
• 201000006549 dyspepsia Diseases 0.000 claims description 2
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• 208000037805 labour Diseases 0.000 claims description 2
• 230000005906 menstruation Effects 0.000 claims description 2
• 206010027599 migraine Diseases 0.000 claims description 2
• GUFNMDKLQYLUPM-UHFFFAOYSA-N n-(3,4-difluorophenyl)-2-(morpholin-4-ylmethyl)-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]pyrimidin-4-amine Chemical compound C1=C(F)C(F)=CC=C1NC1=CC(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=NC(CN2CCOCC2)=N1 GUFNMDKLQYLUPM-UHFFFAOYSA-N 0.000 claims description 2
• UPKCNXKIZZVNAY-UHFFFAOYSA-N n-(3,4-difluorophenyl)-5-methyl-2-morpholin-4-yl-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]pyrimidin-4-amine Chemical compound N1=C(N2CCOCC2)N=C(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)C(C)=C1NC1=CC=C(F)C(F)=C1 UPKCNXKIZZVNAY-UHFFFAOYSA-N 0.000 claims description 2
• 201000009985 neuronitis Diseases 0.000 claims description 2
• 201000008482 osteoarthritis Diseases 0.000 claims description 2
• 239000006187 pill Substances 0.000 claims description 2
• 238000001356 surgical procedure Methods 0.000 claims description 2
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• 206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
• 239000002435 venom Substances 0.000 claims description 2
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• 150000002431 hydrogen Chemical class 0.000 claims 53
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 14
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 7
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 4
• 125000001589 carboacyl group Chemical group 0.000 claims 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
• CKCSYEGSCQSPBJ-UHFFFAOYSA-N 4-n-butyl-6-[4-(2-chlorophenyl)-2-methylpiperazin-1-yl]-2-n-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CC=2)Cl)C)=NC(NCCCC)=NC=1NC1=CC=C(C(F)(C(F)(F)F)C(F)(F)F)C=C1 CKCSYEGSCQSPBJ-UHFFFAOYSA-N 0.000 claims 2
• FEKKLHXJTQCTCM-UHFFFAOYSA-N 4-n-butyl-6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(NCCCC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 FEKKLHXJTQCTCM-UHFFFAOYSA-N 0.000 claims 2
• XFANHXUBPHMSBZ-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n,4-n-dimethyl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=C(N=1)N(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 XFANHXUBPHMSBZ-UHFFFAOYSA-N 0.000 claims 2
• NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 claims 2
• ZIHUFGHPYQTYIP-UHFFFAOYSA-N 1-(3-chloropyridin-2-yl)-3-methylpiperazine Chemical compound C1CNC(C)CN1C1=NC=CC=C1Cl ZIHUFGHPYQTYIP-UHFFFAOYSA-N 0.000 claims 1
• BGXLQQPPCXCWTQ-UHFFFAOYSA-N 2-(diethylaminomethyl)-n-(3,4-difluorophenyl)-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]pyrimidin-4-amine Chemical compound C=1C(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=NC(CN(CC)CC)=NC=1NC1=CC=C(F)C(F)=C1 BGXLQQPPCXCWTQ-UHFFFAOYSA-N 0.000 claims 1
• MAKKUUWCUWDLMR-UHFFFAOYSA-N 2-n,2-n-dimethyl-6-(4-phenylpiperazin-1-yl)-4-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C=CC=CC=2)=NC(N(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 MAKKUUWCUWDLMR-UHFFFAOYSA-N 0.000 claims 1
• PSUNORNAXZIHNE-UHFFFAOYSA-N 2-n-(2,5-dimethoxyphenyl)-4-n,4-n-diethyl-6-(4-pyridin-2-ylpiperazin-1-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2N=CC=CC=2)=NC(N(CC)CC)=NC=1NC1=CC(OC)=CC=C1OC PSUNORNAXZIHNE-UHFFFAOYSA-N 0.000 claims 1
• JGLBOYDPGRVVRB-UHFFFAOYSA-N 2-n-(3,4-difluorophenyl)-4-n,4-n-diethyl-6-(4-pyridin-2-ylpiperazin-1-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2N=CC=CC=2)=NC(N(CC)CC)=NC=1NC1=CC=C(F)C(F)=C1 JGLBOYDPGRVVRB-UHFFFAOYSA-N 0.000 claims 1
• WEZDJQAAKUQRMU-UHFFFAOYSA-N 2-n-(3,4-difluorophenyl)-4-n,4-n-diethyl-6-[2-methyl-4-(3-methylsulfonylpyridin-2-yl)piperazin-1-yl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)S(C)(=O)=O)C)=NC(N(CC)CC)=NC=1NC1=CC=C(F)C(F)=C1 WEZDJQAAKUQRMU-UHFFFAOYSA-N 0.000 claims 1
• SDTFNLPGNOXZSI-UHFFFAOYSA-N 2-n-(3,4-difluorophenyl)-4-n,4-n-diethyl-6-[2-methyl-4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)C(F)(F)F)C)=NC(N(CC)CC)=NC=1NC1=CC=C(F)C(F)=C1 SDTFNLPGNOXZSI-UHFFFAOYSA-N 0.000 claims 1
• RXSQCNFKEGILQO-UHFFFAOYSA-N 2-n-(3-chlorophenyl)-6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n,4-n-diethyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(CC)CC)=NC=1NC1=CC=CC(Cl)=C1 RXSQCNFKEGILQO-UHFFFAOYSA-N 0.000 claims 1
• OYYXQGQMAPKESO-UHFFFAOYSA-N 2-n-butan-2-yl-6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(NC(C)CC)=NC=1NC1=CC=C(C(F)(C(F)(F)F)C(F)(F)F)C=C1 OYYXQGQMAPKESO-UHFFFAOYSA-N 0.000 claims 1
• AGQUZLXGBIUCPH-UHFFFAOYSA-N 4,6-bis[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=N1 AGQUZLXGBIUCPH-UHFFFAOYSA-N 0.000 claims 1
• YPLFSKLRYVKWDJ-UHFFFAOYSA-N 4-(2-chlorophenyl)-6-[2-methyl-4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)C(F)(F)F)CCN1C(N=C(N=1)C=2C(=CC=CC=2)Cl)=NC=1NC1=CC=C(C(F)(F)F)C=C1 YPLFSKLRYVKWDJ-UHFFFAOYSA-N 0.000 claims 1
• AMFHFOKUUUNUDC-UHFFFAOYSA-N 4-(4-butylphenyl)-6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound C1=CC(CCCC)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=NC(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=N1 AMFHFOKUUUNUDC-UHFFFAOYSA-N 0.000 claims 1
• OJCXMWOUBGPUTF-UHFFFAOYSA-N 4-[2-methyl-4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-n,6-bis[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)C(F)(F)F)CCN1C(N=C(N=1)C=2C=CC(=CC=2)C(F)(F)F)=NC=1NC1=CC=C(C(F)(F)F)C=C1 OJCXMWOUBGPUTF-UHFFFAOYSA-N 0.000 claims 1
• FJLVYLNENYHVIV-UHFFFAOYSA-N 4-[2-methyl-4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]-6-[[2-(trifluoromethyl)phenyl]methoxy]-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)C(F)(F)F)CCN1C(N=C(OCC=1C(=CC=CC=1)C(F)(F)F)N=1)=NC=1NC1=CC=C(C(F)(F)F)C=C1 FJLVYLNENYHVIV-UHFFFAOYSA-N 0.000 claims 1
• NGBYGHKNNOMLLA-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-6-(2,4-dimethoxyphenyl)-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound COC1=CC(OC)=CC=C1C1=NC(NC=2C=CC(=CC=2)C(F)(F)F)=NC(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=N1 NGBYGHKNNOMLLA-UHFFFAOYSA-N 0.000 claims 1
• XQJXUNGPVGQKLV-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-n-(3,4-difluorophenyl)-6-morpholin-4-yl-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=C(F)C(F)=C1 XQJXUNGPVGQKLV-UHFFFAOYSA-N 0.000 claims 1
• MPZOGRXAAGXZNL-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-n-(3-fluorophenyl)-6-morpholin-4-yl-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC(F)=C1 MPZOGRXAAGXZNL-UHFFFAOYSA-N 0.000 claims 1
• LSRWWLQOTLXTAF-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]-6-[[2-(trifluoromethyl)phenyl]methoxy]-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=C(OCC=1C(=CC=CC=1)C(F)(F)F)N=1)=NC=1NC1=CC=C(C(F)(F)F)C=C1 LSRWWLQOTLXTAF-UHFFFAOYSA-N 0.000 claims 1
• VJQQEEHUMKJUDJ-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-6-methyl-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 VJQQEEHUMKJUDJ-UHFFFAOYSA-N 0.000 claims 1
• ORBZXOHCCODDCR-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-6-morpholin-4-yl-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCOCC2)=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=N1 ORBZXOHCCODDCR-UHFFFAOYSA-N 0.000 claims 1
• QUQVNDPXEIYKLX-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-6-morpholin-4-yl-n-phenyl-1,3,5-triazin-2-amine Chemical compound ClC1=CC=CN=C1N1CCN(C=2N=C(N=C(NC=3C=CC=CC=3)N=2)N2CCOCC2)CC1 QUQVNDPXEIYKLX-UHFFFAOYSA-N 0.000 claims 1
• QVLOMKBQNCBYKA-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-6-piperidin-1-yl-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCCCC2)=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=N1 QVLOMKBQNCBYKA-UHFFFAOYSA-N 0.000 claims 1
• FPGBEHVXBZWSNY-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-(3-fluorophenyl)-6-(2-methylpyrrolidin-1-yl)-1,3,5-triazin-2-amine Chemical compound CC1CCCN1C1=NC(NC=2C=C(F)C=CC=2)=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=N1 FPGBEHVXBZWSNY-UHFFFAOYSA-N 0.000 claims 1
• DAYOZAGMNWEPNN-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-(3-fluorophenyl)-6-morpholin-4-yl-1,3,5-triazin-2-amine Chemical compound FC1=CC=CC(NC=2N=C(N=C(N=2)N2CCOCC2)N2CCN(CC2)C=2C(=CC=CN=2)Cl)=C1 DAYOZAGMNWEPNN-UHFFFAOYSA-N 0.000 claims 1
• GKLMIVYLZLAKEP-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-(3-fluorophenyl)-6-piperidin-1-yl-1,3,5-triazin-2-amine Chemical compound FC1=CC=CC(NC=2N=C(N=C(N=2)N2CCCCC2)N2CCN(CC2)C=2C(=CC=CN=2)Cl)=C1 GKLMIVYLZLAKEP-UHFFFAOYSA-N 0.000 claims 1
• YHHKPMQRNFYTNK-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-(3-fluorophenyl)-6-pyrrolidin-1-yl-1,3,5-triazin-2-amine Chemical compound FC1=CC=CC(NC=2N=C(N=C(N=2)N2CCCC2)N2CCN(CC2)C=2C(=CC=CN=2)Cl)=C1 YHHKPMQRNFYTNK-UHFFFAOYSA-N 0.000 claims 1
• OIJAUMKRTCCEEN-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-(4-fluorophenyl)-6-morpholin-4-yl-1,3,5-triazin-2-amine Chemical compound C1=CC(F)=CC=C1NC1=NC(N2CCOCC2)=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=N1 OIJAUMKRTCCEEN-UHFFFAOYSA-N 0.000 claims 1
• KLGKCXJFRKRKCB-UHFFFAOYSA-N 4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-(4-methylphenyl)-6-morpholin-4-yl-1,3,5-triazin-2-amine Chemical compound C1=CC(C)=CC=C1NC1=NC(N2CCOCC2)=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=N1 KLGKCXJFRKRKCB-UHFFFAOYSA-N 0.000 claims 1
• CQUDADLWJDIRFD-UHFFFAOYSA-N 4-[[4-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-6-(diethylamino)-1,3,5-triazin-2-yl]amino]benzonitrile Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(CC)CC)=NC=1NC1=CC=C(C#N)C=C1 CQUDADLWJDIRFD-UHFFFAOYSA-N 0.000 claims 1
• FAYCKEOLDMRDQF-UHFFFAOYSA-N 4-chloro-6-[2-methyl-4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)C(F)(F)F)CCN1C(N=1)=NC(Cl)=NC=1NC1=CC=C(C(F)(F)F)C=C1 FAYCKEOLDMRDQF-UHFFFAOYSA-N 0.000 claims 1
• BSYAXBZYLVNOAP-UHFFFAOYSA-N 4-chloro-6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-n-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-1,3,5-triazin-2-amine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=1)=NC(Cl)=NC=1NC1=CC=C(C(F)(C(F)(F)F)C(F)(F)F)C=C1 BSYAXBZYLVNOAP-UHFFFAOYSA-N 0.000 claims 1
• FBECRUIXXQZJIG-UHFFFAOYSA-N 4-chloro-6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(Cl)=NC(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=N1 FBECRUIXXQZJIG-UHFFFAOYSA-N 0.000 claims 1
• UAAJGWQXIKMBES-UHFFFAOYSA-N 4-morpholin-4-yl-n-[4-(trifluoromethyl)phenyl]-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-1,3,5-triazin-2-amine Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC(N2CCOCC2)=NC(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=N1 UAAJGWQXIKMBES-UHFFFAOYSA-N 0.000 claims 1
• PKNQHXTWPKTCNO-UHFFFAOYSA-N 4-n,4-n-dibutyl-6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(N(CCCC)CCCC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 PKNQHXTWPKTCNO-UHFFFAOYSA-N 0.000 claims 1
• CXMORRPJXUQLNG-UHFFFAOYSA-N 4-n,4-n-diethyl-2-n-(4-fluorophenyl)-6-(4-pyridin-2-ylpiperazin-1-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2N=CC=CC=2)=NC(N(CC)CC)=NC=1NC1=CC=C(F)C=C1 CXMORRPJXUQLNG-UHFFFAOYSA-N 0.000 claims 1
• BUSMCRFSAOKWPO-UHFFFAOYSA-N 4-n,4-n-dimethyl-2-n-[4-(trifluoromethyl)phenyl]-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=NC(N(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 BUSMCRFSAOKWPO-UHFFFAOYSA-N 0.000 claims 1
• ZCOMVSHFGRLKRF-UHFFFAOYSA-N 4-n,4-n-dimethyl-6-(4-pyridin-2-ylpiperazin-1-yl)-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2N=CC=CC=2)=NC(N(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 ZCOMVSHFGRLKRF-UHFFFAOYSA-N 0.000 claims 1
• UXTSXCPXWJZJEA-UHFFFAOYSA-N 4-n-(3-methylbutyl)-2-n-[4-(trifluoromethyl)phenyl]-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=NC(NCCC(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 UXTSXCPXWJZJEA-UHFFFAOYSA-N 0.000 claims 1
• KVMNONQOJFCIFH-UHFFFAOYSA-N 4-n-(3-methylbutyl)-6-[2-methyl-4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)C(F)(F)F)C)=NC(NCCC(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 KVMNONQOJFCIFH-UHFFFAOYSA-N 0.000 claims 1
• GRWIWYVKPSMTJW-UHFFFAOYSA-N 4-n-benzyl-6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=C(NC=1C=CC(=CC=1)C(F)(F)F)N=1)=NC=1NCC1=CC=CC=C1 GRWIWYVKPSMTJW-UHFFFAOYSA-N 0.000 claims 1
• IVOFRNMSWYRJGQ-UHFFFAOYSA-N 4-n-butyl-6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-methyl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(N(C)CCCC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 IVOFRNMSWYRJGQ-UHFFFAOYSA-N 0.000 claims 1
• XPBCALJWTRASSO-UHFFFAOYSA-N 4-n-methyl-2-n-phenyl-4-n-propan-2-yl-6-[4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)C(F)(F)F)=NC(N(C)C(C)C)=NC=1NC1=CC=CC=C1 XPBCALJWTRASSO-UHFFFAOYSA-N 0.000 claims 1
• CWFBFDZFABJMOF-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-2-n-(3,4-difluorophenyl)-4-n,4-n-diethyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(N(CC)CC)=NC=1NC1=CC=C(F)C(F)=C1 CWFBFDZFABJMOF-UHFFFAOYSA-N 0.000 claims 1
• JQVGSNINXRKYOO-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-2-n-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)phenyl]-4-n-propyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(NCCC)=NC=1NC1=CC=C(C(F)(C(F)(F)F)C(F)(F)F)C=C1 JQVGSNINXRKYOO-UHFFFAOYSA-N 0.000 claims 1
• QSPKQSJYPKTYJD-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-2-n-[4-(trifluoromethyl)phenyl]-4-n-[[3-(trifluoromethyl)phenyl]methyl]-1,3,5-triazine-2,4-diamine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=C(NC=1C=CC(=CC=1)C(F)(F)F)N=1)=NC=1NCC1=CC=CC(C(F)(F)F)=C1 QSPKQSJYPKTYJD-UHFFFAOYSA-N 0.000 claims 1
• JHUKJCHMTQYIFW-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n,4-n-dipropyl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(N(CCC)CCC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 JHUKJCHMTQYIFW-UHFFFAOYSA-N 0.000 claims 1
• LBJMRACTLIORAP-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-(2-methylpropyl)-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(NCC(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 LBJMRACTLIORAP-UHFFFAOYSA-N 0.000 claims 1
• WNDFRUOLYSUSHE-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-(3-methylbutyl)-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(NCCC(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 WNDFRUOLYSUSHE-UHFFFAOYSA-N 0.000 claims 1
• ZIVWRXRKRIZOEG-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-(3-phenylpropyl)-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound CC1CN(C=2C(=CC=CN=2)Cl)CCN1C(N=C(NC=1C=CC(=CC=1)C(F)(F)F)N=1)=NC=1NCCCC1=CC=CC=C1 ZIVWRXRKRIZOEG-UHFFFAOYSA-N 0.000 claims 1
• QNAWQOGESBFVTH-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-methyl-4-n-propan-2-yl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(N(C)C(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 QNAWQOGESBFVTH-UHFFFAOYSA-N 0.000 claims 1
• KJAYKRODNJTQHS-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-methyl-4-n-propyl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(N(C)CCC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 KJAYKRODNJTQHS-UHFFFAOYSA-N 0.000 claims 1
• HPXOUJURBAFYPL-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)-2-methylpiperazin-1-yl]-4-n-propyl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2C(CN(CC2)C=2C(=CC=CN=2)Cl)C)=NC(NCCC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 HPXOUJURBAFYPL-UHFFFAOYSA-N 0.000 claims 1
• UNDUUVFKOCVINP-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-2-n-(3,4-difluorophenyl)-4-n,4-n-diethyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(CC)CC)=NC=1NC1=CC=C(F)C(F)=C1 UNDUUVFKOCVINP-UHFFFAOYSA-N 0.000 claims 1
• ZCMLFMULJPCBGT-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-2-n-(3-fluorophenyl)-4-n,4-n-dimethyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(C)C)=NC=1NC1=CC=CC(F)=C1 ZCMLFMULJPCBGT-UHFFFAOYSA-N 0.000 claims 1
• JEGISJAEMKVQBL-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-2-n-(3-fluorophenyl)-4-n-methyl-4-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(C)C(C)C)=NC=1NC1=CC=CC(F)=C1 JEGISJAEMKVQBL-UHFFFAOYSA-N 0.000 claims 1
• DKHOACYYBZWWRV-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-2-n-(3-fluorophenyl)-4-n-methyl-4-n-propyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(C)CCC)=NC=1NC1=CC=CC(F)=C1 DKHOACYYBZWWRV-UHFFFAOYSA-N 0.000 claims 1
• GFAYNUCWGKZMJN-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-2-n-(3-fluorophenyl)-4-n-propyl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(NCCC)=NC=1NC1=CC=CC(F)=C1 GFAYNUCWGKZMJN-UHFFFAOYSA-N 0.000 claims 1
• ZOIYBUXJYDMZGL-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n,4-n-diethyl-2-n-(3-fluorophenyl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(CC)CC)=NC=1NC1=CC=CC(F)=C1 ZOIYBUXJYDMZGL-UHFFFAOYSA-N 0.000 claims 1
• SVUIQMZWEBGNDW-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n,4-n-diethyl-2-n-(3-methoxyphenyl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(CC)CC)=NC=1NC1=CC=CC(OC)=C1 SVUIQMZWEBGNDW-UHFFFAOYSA-N 0.000 claims 1
• FUHLTBJNQQVRLF-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n,4-n-dimethyl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 FUHLTBJNQQVRLF-UHFFFAOYSA-N 0.000 claims 1
• RKRBZRDGCUSPHT-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n-ethyl-4-n-propan-2-yl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(C(C)C)CC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 RKRBZRDGCUSPHT-UHFFFAOYSA-N 0.000 claims 1
• YFEMZSIFTOJHAS-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n-methyl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(NC)=NC=1NC1=CC=C(C(F)(F)F)C=C1 YFEMZSIFTOJHAS-UHFFFAOYSA-N 0.000 claims 1
• GYTTTZFNKGRGIE-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n-methyl-2-n-phenyl-4-n-propan-2-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(C)C(C)C)=NC=1NC1=CC=CC=C1 GYTTTZFNKGRGIE-UHFFFAOYSA-N 0.000 claims 1
• AXZAQOKYOQDWLX-UHFFFAOYSA-N 6-[4-(3-chloropyridin-2-yl)piperazin-1-yl]-4-n-methyl-4-n-propan-2-yl-2-n-[4-(trifluoromethyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCN(CC2)C=2C(=CC=CN=2)Cl)=NC(N(C)C(C)C)=NC=1NC1=CC=C(C(F)(F)F)C=C1 AXZAQOKYOQDWLX-UHFFFAOYSA-N 0.000 claims 1
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