CA2537883A1 - Substituted bicyclic quinazolin-4-ylamine derivatives - Google Patents

Info

Publication number

CA2537883A1

CA2537883A1 CA002537883A CA2537883A CA2537883A1 CA 2537883 A1 CA2537883 A1 CA 2537883A1 CA 002537883 A CA002537883 A CA 002537883A CA 2537883 A CA2537883 A CA 2537883A CA 2537883 A1 CA2537883 A1 CA 2537883A1

Authority

CA

Canada

Prior art keywords

compound

pyridin

c6alkyl

pharmaceutically acceptable

pyrido

Prior art date

2003-09-09

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
• CIPO
• Discuss

• -1 bicyclic quinazolin-4-ylamine derivatives Chemical class 0.000 title claims abstract description 159
• 150000001875 compounds Chemical class 0.000 claims abstract description 338
• 238000000034 method Methods 0.000 claims abstract description 75
• 230000000694 effects Effects 0.000 claims abstract description 60
• 239000003446 ligand Substances 0.000 claims abstract description 37
• 241001465754 Metazoa Species 0.000 claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 238000000338 in vitro Methods 0.000 claims abstract description 14
• 238000001727 in vivo Methods 0.000 claims abstract description 11
• 150000003839 salts Chemical class 0.000 claims description 106
• 208000002193 Pain Diseases 0.000 claims description 101
• 125000001424 substituent group Chemical group 0.000 claims description 97
• 108010062740 TRPV Cation Channels Proteins 0.000 claims description 96
• 102000011040 TRPV Cation Channels Human genes 0.000 claims description 95
• 230000036407 pain Effects 0.000 claims description 89
• 239000000203 mixture Substances 0.000 claims description 79
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 210000004027 cell Anatomy 0.000 claims description 73
• 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 68
• 238000003556 assay Methods 0.000 claims description 61
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 54
• 150000002367 halogens Chemical class 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 53
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 47
• 238000009739 binding Methods 0.000 claims description 43
• 230000027455 binding Effects 0.000 claims description 41
• 229960002504 capsaicin Drugs 0.000 claims description 32
• 235000017663 capsaicin Nutrition 0.000 claims description 32
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 239000000556 agonist Substances 0.000 claims description 27
• 208000004296 neuralgia Diseases 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 208000003251 Pruritus Diseases 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 241000282414 Homo sapiens Species 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 208000021722 neuropathic pain Diseases 0.000 claims description 13
• 125000004043 oxo group Chemical group O=* 0.000 claims description 13
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 12
• 239000011575 calcium Substances 0.000 claims description 12
• 229910052791 calcium Inorganic materials 0.000 claims description 12
• 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 claims description 12
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 206010011224 Cough Diseases 0.000 claims description 10
• 208000031361 Hiccup Diseases 0.000 claims description 10
• 206010029240 Neuritis Diseases 0.000 claims description 10
• 229910052727 yttrium Inorganic materials 0.000 claims description 10
• 208000014674 injury Diseases 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 8
• 229910052721 tungsten Inorganic materials 0.000 claims description 8
• 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 7
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 7
• 125000002837 carbocyclic group Chemical group 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
• 125000004193 piperazinyl group Chemical group 0.000 claims description 7
• 239000003491 tear gas Substances 0.000 claims description 7
• 125000004765 (C1-C4) haloalkyl group Chemical group 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
• 210000002569 neuron Anatomy 0.000 claims description 6
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 6
• 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
• 125000000468 ketone group Chemical group 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
• 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
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 231100000869 headache Toxicity 0.000 claims description 4
• 230000000968 intestinal effect Effects 0.000 claims description 4
• 230000007823 neuropathy Effects 0.000 claims description 4
• 239000000825 pharmaceutical preparation Substances 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
• 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 3
• 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
• 208000006545 Chronic Obstructive Pulmonary Disease 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
• 230000007885 bronchoconstriction Effects 0.000 claims description 3
• 208000004967 femoral neuropathy Diseases 0.000 claims description 3
• 238000000099 in vitro assay Methods 0.000 claims description 3
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 3
• 208000032184 meralgia paresthetica Diseases 0.000 claims description 3
• 230000001737 promoting effect Effects 0.000 claims description 3
• 208000004371 toothache Diseases 0.000 claims description 3
• 208000030507 AIDS Diseases 0.000 claims description 2
• 208000001387 Causalgia 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
• 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
• 208000014617 hemorrhoid Diseases 0.000 claims description 2
• 208000037805 labour Diseases 0.000 claims description 2
• 230000005906 menstruation Effects 0.000 claims description 2
• 206010027599 migraine Diseases 0.000 claims description 2
• 201000009985 neuronitis Diseases 0.000 claims description 2
• 201000008482 osteoarthritis Diseases 0.000 claims description 2
• 208000020431 spinal cord injury Diseases 0.000 claims description 2
• 238000001356 surgical procedure Methods 0.000 claims description 2
• 208000011580 syndromic disease Diseases 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 206010044652 trigeminal neuralgia Diseases 0.000 claims description 2
• 239000002435 venom Substances 0.000 claims description 2
• 210000001048 venom Anatomy 0.000 claims description 2
• 231100000611 venom Toxicity 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
• IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims 2
• FHTHLMOKHXEATE-UHFFFAOYSA-N 1-[3,3-dimethyl-6-[[2-(2-methylpropoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]pyrido[2,3-d]pyrimidin-4-yl]amino]-2h-indol-1-yl]ethanone Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CN4C(C)=O)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F FHTHLMOKHXEATE-UHFFFAOYSA-N 0.000 claims 1
• KTTBKTIZTKLPCG-UHFFFAOYSA-N 1-[3,3-dimethyl-6-[[2-(2-methylpropoxymethyl)-7-pyridin-2-ylpyrido[2,3-d]pyrimidin-4-yl]amino]-2h-indol-1-yl]ethanone Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CN4C(C)=O)(C)C)=CC=3)=C2C=CC=1C1=CC=CC=N1 KTTBKTIZTKLPCG-UHFFFAOYSA-N 0.000 claims 1
• FZODJOGHTDQWND-UHFFFAOYSA-N 1-[6-[[2-(methoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]pyrido[2,3-d]pyrimidin-4-yl]amino]-3,3-dimethyl-2h-indol-1-yl]ethanone Chemical compound N=1C2=NC(COC)=NC(NC=3C=C4C(C(CN4C(C)=O)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F FZODJOGHTDQWND-UHFFFAOYSA-N 0.000 claims 1
• DDHQDLDEVUBIAJ-UHFFFAOYSA-N 1-[6-[[7-(3-chloropyridin-2-yl)-2-(ethoxymethyl)pyrido[2,3-d]pyrimidin-4-yl]amino]-3,3-dimethyl-2h-indol-1-yl]ethanone Chemical compound N=1C2=NC(COCC)=NC(NC=3C=C4C(C(CN4C(C)=O)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1Cl DDHQDLDEVUBIAJ-UHFFFAOYSA-N 0.000 claims 1
• VZTYUPSGOWLVBU-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(1,3,3-trimethyl-2h-indol-6-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CN4C)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F VZTYUPSGOWLVBU-UHFFFAOYSA-N 0.000 claims 1
• XSVWHBRBBWRCSN-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F XSVWHBRBBWRCSN-UHFFFAOYSA-N 0.000 claims 1
• IOMOPRNICIERFL-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)-7-pyridin-2-yl-n-(1,3,3-trimethyl-2h-indol-6-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CN4C)(C)C)=CC=3)=C2C=CC=1C1=CC=CC=N1 IOMOPRNICIERFL-UHFFFAOYSA-N 0.000 claims 1
• QPACYHJNEDJKGO-UHFFFAOYSA-N 2-(2-methylpropoxymethyl)-7-pyridin-2-yl-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=CC=CC=N1 QPACYHJNEDJKGO-UHFFFAOYSA-N 0.000 claims 1
• QWUYTCGIPVPPBA-UHFFFAOYSA-N 2-(ethoxymethyl)-7-(3-methylpyridin-2-yl)-n-(1,3,3-trimethyl-2h-indol-6-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC)=NC(NC=3C=C4C(C(CN4C)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C QWUYTCGIPVPPBA-UHFFFAOYSA-N 0.000 claims 1
• ULYHLTQGPSTNIH-UHFFFAOYSA-N 2-(ethoxymethyl)-7-(3-methylpyridin-2-yl)-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC)=NC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C ULYHLTQGPSTNIH-UHFFFAOYSA-N 0.000 claims 1
• DBHKMBAQFSWZDT-UHFFFAOYSA-N 2-(methoxymethyl)-7-(3-methylpyridin-2-yl)-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COC)=NC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C DBHKMBAQFSWZDT-UHFFFAOYSA-N 0.000 claims 1
• GPWJOEUJUVTTEP-UHFFFAOYSA-N 2-(methoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)-1,8-naphthyridin-4-amine Chemical compound N=1C2=NC(COC)=CC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F GPWJOEUJUVTTEP-UHFFFAOYSA-N 0.000 claims 1
• FOUNQNSFZOTUHB-UHFFFAOYSA-N 2-(methoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COC)=NC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F FOUNQNSFZOTUHB-UHFFFAOYSA-N 0.000 claims 1
• FEWLQPOQAJRPHJ-UHFFFAOYSA-N 2-(phenylmethoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)quinazolin-4-amine Chemical compound C=1C=C2C(C)(C)CN(C)CC2=CC=1NC(C1=CC=C(C=C1N=1)C=2C(=CC=CN=2)C(F)(F)F)=NC=1COCC1=CC=CC=C1 FEWLQPOQAJRPHJ-UHFFFAOYSA-N 0.000 claims 1
• PMUFZJDTZFHGMK-UHFFFAOYSA-N 2-methyl-n-[2-(2-methylpropoxymethyl)-7-(3-methylpyridin-2-yl)pyrido[2,3-d]pyrimidin-4-yl]-1,3-benzoxazol-6-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4OC(C)=NC4=CC=3)=C2C=CC=1C1=NC=CC=C1C PMUFZJDTZFHGMK-UHFFFAOYSA-N 0.000 claims 1
• VFMAIJOSEDCWII-UHFFFAOYSA-N 2-methyl-n-[2-(2-methylpropoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]pyrido[2,3-d]pyrimidin-4-yl]-1,3-benzoxazol-6-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4OC(C)=NC4=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F VFMAIJOSEDCWII-UHFFFAOYSA-N 0.000 claims 1
• BVHMUENOZZCADF-UHFFFAOYSA-N 4-methyl-n-[2-(2-methylpropoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]pyrido[2,3-d]pyrimidin-4-yl]-2,3-dihydro-1,4-benzoxazin-6-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4N(C)CCOC4=CC=3)=C2C=CC=1C1=NC=CC=C1C(F)(F)F BVHMUENOZZCADF-UHFFFAOYSA-N 0.000 claims 1
• LBYNRSNRKHMYOF-UHFFFAOYSA-N 4-methyl-n-[2-(2-methylpropoxymethyl)-7-pyridin-2-ylpyrido[2,3-d]pyrimidin-4-yl]-2,3-dihydro-1,4-benzoxazin-6-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4N(C)CCOC4=CC=3)=C2C=CC=1C1=CC=CC=N1 LBYNRSNRKHMYOF-UHFFFAOYSA-N 0.000 claims 1
• RPZSXJWMNHJINQ-UHFFFAOYSA-N 4-methyl-n-[2-(phenylmethoxymethyl)-7-[3-(trifluoromethyl)pyridin-2-yl]quinazolin-4-yl]-2,3-dihydro-1,4-benzoxazin-6-amine Chemical compound C1=C2N(C)CCOC2=CC=C1NC(C1=CC=C(C=C1N=1)C=2C(=CC=CN=2)C(F)(F)F)=NC=1COCC1=CC=CC=C1 RPZSXJWMNHJINQ-UHFFFAOYSA-N 0.000 claims 1
• VETKDCUTSMTNIN-UHFFFAOYSA-N 7-(3-chloropyridin-2-yl)-2-(2-methylpropoxymethyl)-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1Cl VETKDCUTSMTNIN-UHFFFAOYSA-N 0.000 claims 1
• BAGYILOEONTUTO-UHFFFAOYSA-N 7-(3-chloropyridin-2-yl)-2-(ethoxymethyl)-n-(1,3,3-trimethyl-2h-indol-6-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC)=NC(NC=3C=C4C(C(CN4C)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1Cl BAGYILOEONTUTO-UHFFFAOYSA-N 0.000 claims 1
• DRNCPHGTYCPFCG-UHFFFAOYSA-N 7-(3-chloropyridin-2-yl)-2-(ethoxymethyl)-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC)=NC(NC=3C=C4C(C(CN(C)C4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1Cl DRNCPHGTYCPFCG-UHFFFAOYSA-N 0.000 claims 1
• CAKUIYWZXNHBSY-UHFFFAOYSA-N 7-(3-chloropyridin-2-yl)-2-[(2,6-dimethylmorpholin-4-yl)methyl]-n-(2,4,4-trimethyl-1,3-dihydroisoquinolin-7-yl)pyrido[3,2-d]pyrimidin-4-amine Chemical compound C1C(C)OC(C)CN1CC1=NC(NC=2C=C3C(C(CN(C)C3)(C)C)=CC=2)=C(N=CC(=C2)C=3C(=CC=CN=3)Cl)C2=N1 CAKUIYWZXNHBSY-UHFFFAOYSA-N 0.000 claims 1
• OZDKRWMSINJUKE-UHFFFAOYSA-N 7-(3-chloropyridin-2-yl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(2-methylpropoxymethyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4OCCOC4=CC=3)=C2C=CC=1C1=NC=CC=C1Cl OZDKRWMSINJUKE-UHFFFAOYSA-N 0.000 claims 1
• NVHCVLVCJQEYRS-UHFFFAOYSA-N 7-(3-chloropyridin-2-yl)-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(ethoxymethyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC)=NC(NC=3C=C4OCCOC4=CC=3)=C2C=CC=1C1=NC=CC=C1Cl NVHCVLVCJQEYRS-UHFFFAOYSA-N 0.000 claims 1
• NNGGKNWKQGWMGH-UHFFFAOYSA-N 7-(3-chloropyridin-2-yl)-n-(4,4-dimethyl-2,3-dihydro-1h-quinolin-7-yl)-2-(2-methylpropoxymethyl)pyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C2=NC(COCC(C)C)=NC(NC=3C=C4C(C(CCN4)(C)C)=CC=3)=C2C=CC=1C1=NC=CC=C1Cl NNGGKNWKQGWMGH-UHFFFAOYSA-N 0.000 claims 1
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