SK281724B6 - 6-arylpyrido[2,3-d]pyrimidíny, ich použitie a farmaceutické prostriedky na ich báze - Google Patents

Info

Publication number

SK281724B6

SK281724B6 SK609-97A SK60997A SK281724B6 SK 281724 B6 SK281724 B6 SK 281724B6 SK 60997 A SK60997 A SK 60997A SK 281724 B6 SK281724 B6 SK 281724B6

Authority

SK

Slovakia

Prior art keywords

pyrido

pyrimidin

dichlorophenyl

urea

tert

Prior art date

1994-11-14

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
• 150000001875 compounds Chemical class 0.000 claims abstract description 157
• 150000003230 pyrimidines Chemical class 0.000 claims abstract description 40
• 208000037803 restenosis Diseases 0.000 claims abstract description 15
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 12
• 208000035143 Bacterial infection Diseases 0.000 claims abstract 2
• 208000022362 bacterial infectious disease Diseases 0.000 claims abstract 2
• -1 2,6-dichlorophenyl Chemical group 0.000 claims description 197
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 101
• 239000000203 mixture Substances 0.000 claims description 85
• 238000000034 method Methods 0.000 claims description 81
• 150000003839 salts Chemical class 0.000 claims description 77
• 239000002253 acid Substances 0.000 claims description 71
• 239000000243 solution Substances 0.000 claims description 54
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 239000004202 carbamide Substances 0.000 claims description 26
• 125000003118 aryl group Chemical group 0.000 claims description 25
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 23
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 125000006308 propyl amino group Chemical group 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 125000000335 thiazolyl group Chemical group 0.000 claims description 17
• 239000004480 active ingredient Substances 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 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 description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 14
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 239000011593 sulfur Substances 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• GCTRVFZGBTUDPW-UHFFFAOYSA-N 1-[6-(2,6-dichlorophenyl)-2-[4-(diethylamino)butylamino]pyrido[2,3-d]pyrimidin-7-yl]-3-ethylurea Chemical compound CCNC(=O)NC1=NC2=NC(NCCCCN(CC)CC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl GCTRVFZGBTUDPW-UHFFFAOYSA-N 0.000 claims description 10
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical group 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
• 230000002062 proliferating effect Effects 0.000 claims description 9
• 150000007513 acids Chemical class 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 7
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 7
• 229920002472 Starch Polymers 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 239000011780 sodium chloride Substances 0.000 claims description 7
• 239000008107 starch Substances 0.000 claims description 7
• 235000019698 starch Nutrition 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 239000000843 powder Substances 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 239000000829 suppository Substances 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• LYJIVFCOOJRVBF-UHFFFAOYSA-N 1-[6-(2,6-dichlorophenyl)-2-[4-(diethylamino)butylamino]pyrido[2,3-d]pyrimidin-7-yl]-3-phenylurea Chemical compound N=1C2=NC(NCCCCN(CC)CC)=NC=C2C=C(C=2C(=CC=CC=2Cl)Cl)C=1NC(=O)NC1=CC=CC=C1 LYJIVFCOOJRVBF-UHFFFAOYSA-N 0.000 claims description 4
• ZZEVABBPVKGWBW-UHFFFAOYSA-N 1-tert-butyl-3-[2-(tert-butylcarbamoylamino)-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(NC(=O)NC(C)(C)C)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl ZZEVABBPVKGWBW-UHFFFAOYSA-N 0.000 claims description 4
• UKIASJDTPIGRRQ-UHFFFAOYSA-N 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-(dimethylaminomethylideneamino)pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(N=CN(C)C)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl UKIASJDTPIGRRQ-UHFFFAOYSA-N 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000002837 carbocyclic group Chemical group 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• 238000002347 injection Methods 0.000 claims description 4
• 239000007924 injection Substances 0.000 claims description 4
• 235000019359 magnesium stearate Nutrition 0.000 claims description 4
• 210000002464 muscle smooth vascular Anatomy 0.000 claims description 4
• XPTLCOMGKOJZAW-UHFFFAOYSA-N n'-[6-(2,6-dichlorophenyl)-2-(dimethylaminomethylideneamino)pyrido[2,3-d]pyrimidin-7-yl]-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=NC2=NC(N=CN(C)C)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl XPTLCOMGKOJZAW-UHFFFAOYSA-N 0.000 claims description 4
• UNSVWZVINKWBKX-UHFFFAOYSA-N n-[2-acetamido-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]acetamide Chemical compound CC(=O)NC1=NC2=NC(NC(=O)C)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl UNSVWZVINKWBKX-UHFFFAOYSA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 239000011734 sodium Substances 0.000 claims description 4
• 229910052708 sodium Inorganic materials 0.000 claims description 4
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
• 239000000454 talc Substances 0.000 claims description 4
• 229910052623 talc Inorganic materials 0.000 claims description 4
• DPPREWYRSZWSKZ-UHFFFAOYSA-N 1-(2-amino-6-pyridin-3-ylpyrido[2,3-d]pyrimidin-7-yl)-3-tert-butylurea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(N)=NC=C2C=C1C1=CC=CN=C1 DPPREWYRSZWSKZ-UHFFFAOYSA-N 0.000 claims description 3
• PTLBTVSQIPIRSE-UHFFFAOYSA-N 1-(2-amino-6-pyridin-4-ylpyrido[2,3-d]pyrimidin-7-yl)-3-tert-butylurea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(N)=NC=C2C=C1C1=CC=NC=C1 PTLBTVSQIPIRSE-UHFFFAOYSA-N 0.000 claims description 3
• SMLFOSIGUQORAV-UHFFFAOYSA-N 1-[2-amino-6-(2,4,6-trimethylphenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound CC1=CC(C)=CC(C)=C1C1=CC2=CN=C(N)N=C2N=C1NC(=O)NC(C)(C)C SMLFOSIGUQORAV-UHFFFAOYSA-N 0.000 claims description 3
• ZYLRLSRJFNDDOX-UHFFFAOYSA-N 1-[2-amino-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-(3-morpholin-4-ylpropyl)thiourea Chemical compound N=1C2=NC(N)=NC=C2C=C(C=2C(=CC=CC=2Cl)Cl)C=1NC(=S)NCCCN1CCOCC1 ZYLRLSRJFNDDOX-UHFFFAOYSA-N 0.000 claims description 3
• RRWSNCZYJCOEFX-UHFFFAOYSA-N 1-[2-amino-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl RRWSNCZYJCOEFX-UHFFFAOYSA-N 0.000 claims description 3
• CYJBQAMTIYIBGY-UHFFFAOYSA-N 1-[2-amino-6-(2-bromo-6-chlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC=C1Br CYJBQAMTIYIBGY-UHFFFAOYSA-N 0.000 claims description 3
• DXAXMTYXAGATCT-UHFFFAOYSA-N 1-[2-amino-6-(3-methoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound COC1=CC=CC(C=2C(=NC3=NC(N)=NC=C3C=2)NC(=O)NC(C)(C)C)=C1 DXAXMTYXAGATCT-UHFFFAOYSA-N 0.000 claims description 3
• CRQMGAADPYRSGJ-UHFFFAOYSA-N 1-[6-(2,6-dichlorophenyl)-2-[3-(diethylamino)propylamino]pyrido[2,3-d]pyrimidin-7-yl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=NC2=NC(NCCCN(CC)CC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl CRQMGAADPYRSGJ-UHFFFAOYSA-N 0.000 claims description 3
• PAZDFSJAERQBCY-UHFFFAOYSA-N 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-[3-(4-methylpiperazin-1-yl)propylamino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CN(C)CCN1CCCNC1=NC=C(C=C(C(NC(=O)NC(C)(C)C)=N2)C=3C(=CC=CC=3Cl)Cl)C2=N1 PAZDFSJAERQBCY-UHFFFAOYSA-N 0.000 claims description 3
• ULIJLYCJYRQKBG-UHFFFAOYSA-N 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-[3-(diethylamino)propylamino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(NCCCN(CC)CC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl ULIJLYCJYRQKBG-UHFFFAOYSA-N 0.000 claims description 3
• KTQXUWCOAYRSAJ-UHFFFAOYSA-N 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-[3-(dimethylamino)propyl-methylamino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(N(C)CCCN(C)C)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl KTQXUWCOAYRSAJ-UHFFFAOYSA-N 0.000 claims description 3
• 208000029578 Muscle disease Diseases 0.000 claims description 3
• 239000002202 Polyethylene glycol Substances 0.000 claims description 3
• TWSKIHWXLLKVLC-UHFFFAOYSA-N [6-(2,6-dichlorophenyl)-2-[3-(4-methylpiperazin-1-yl)propylamino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CN(C)CCN1CCCNC1=NC=C(C=C(C(NC(N)=O)=N2)C=3C(=CC=CC=3Cl)Cl)C2=N1 TWSKIHWXLLKVLC-UHFFFAOYSA-N 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 239000008187 granular material Substances 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 229920001223 polyethylene glycol Polymers 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
• NNYHIJGVHOAIGK-UHFFFAOYSA-N 1-[2-amino-6-(2,3,5,6-tetramethylphenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound CC1=CC(C)=C(C)C(C=2C(=NC3=NC(N)=NC=C3C=2)NC(=O)NC(C)(C)C)=C1C NNYHIJGVHOAIGK-UHFFFAOYSA-N 0.000 claims description 2
• QRWYSOZFHKXHIF-UHFFFAOYSA-N 1-[2-amino-6-(2,3,6-trichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(N)=NC=C2C=C1C1=C(Cl)C=CC(Cl)=C1Cl QRWYSOZFHKXHIF-UHFFFAOYSA-N 0.000 claims description 2
• RKLBPUIJSDPKOA-UHFFFAOYSA-N 1-[2-amino-6-(2,6-dichlorophenyl)pyrido[2,3-d]pyrimidin-7-yl]imidazolidin-2-one Chemical compound N=1C2=NC(N)=NC=C2C=C(C=2C(=CC=CC=2Cl)Cl)C=1N1CCNC1=O RKLBPUIJSDPKOA-UHFFFAOYSA-N 0.000 claims description 2
• DVOMFFXZBJHQPZ-UHFFFAOYSA-N 1-[2-amino-6-(2-methoxyphenyl)pyrido[2,3-d]pyrimidin-7-yl]-3-tert-butylurea Chemical compound COC1=CC=CC=C1C1=CC2=CN=C(N)N=C2N=C1NC(=O)NC(C)(C)C DVOMFFXZBJHQPZ-UHFFFAOYSA-N 0.000 claims description 2
• MKVMEJKNLUWFSQ-UHFFFAOYSA-N 1-tert-butyl-3-[6-(2,6-dichlorophenyl)-2-[4-(diethylamino)butylamino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound CC(C)(C)NC(=O)NC1=NC2=NC(NCCCCN(CC)CC)=NC=C2C=C1C1=C(Cl)C=CC=C1Cl MKVMEJKNLUWFSQ-UHFFFAOYSA-N 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000006309 butyl amino group Chemical group 0.000 claims description 2
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 238000002156 mixing Methods 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• ZAANQRSELTXKBG-UHFFFAOYSA-N 3-morpholin-4-ylpropylthiourea Chemical compound NC(=S)NCCCN1CCOCC1 ZAANQRSELTXKBG-UHFFFAOYSA-N 0.000 claims 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
• 239000001913 cellulose Substances 0.000 claims 2
• 229920002678 cellulose Polymers 0.000 claims 2
• 229920000036 polyvinylpyrrolidone Polymers 0.000 claims 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 claims 2
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims 2
• 239000013589 supplement Substances 0.000 claims 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
• NCBRFZSXMXIOAD-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[6-(2,6-dichlorophenyl)-2-[3-(4-methylpiperazin-1-yl)propylamino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CN(C)CCN1CCCNC1=NC=C(C=C(C(NC(=O)NC=2C=CC(Br)=CC=2)=N2)C=3C(=CC=CC=3Cl)Cl)C2=N1 NCBRFZSXMXIOAD-UHFFFAOYSA-N 0.000 claims 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 claims 1
• HDKFOWNECFEDEY-UHFFFAOYSA-N 1-[6-(2,6-dichlorophenyl)-2-[4-(diethylamino)butylamino]pyrido[2,3-d]pyrimidin-7-yl]-3-(3-morpholin-4-ylpropyl)thiourea Chemical compound N=1C2=NC(NCCCCN(CC)CC)=NC=C2C=C(C=2C(=CC=CC=2Cl)Cl)C=1NC(=S)NCCCN1CCOCC1 HDKFOWNECFEDEY-UHFFFAOYSA-N 0.000 claims 1
• CLVSAAPONJRSGJ-UHFFFAOYSA-N 1-cyclohexyl-3-[6-(2,6-dichlorophenyl)-2-[3-(4-methylpiperazin-1-yl)propylamino]pyrido[2,3-d]pyrimidin-7-yl]urea Chemical compound C1CN(C)CCN1CCCNC1=NC=C(C=C(C(NC(=O)NC2CCCCC2)=N2)C=3C(=CC=CC=3Cl)Cl)C2=N1 CLVSAAPONJRSGJ-UHFFFAOYSA-N 0.000 claims 1
• VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims 1
• NLMKTBGFQGKQEV-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-hexadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO NLMKTBGFQGKQEV-UHFFFAOYSA-N 0.000 claims 1
• RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 claims 1
• WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 claims 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
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