JP2008519850A5 - - Google Patents
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- JP2008519850A5 JP2008519850A5 JP2007541357A JP2007541357A JP2008519850A5 JP 2008519850 A5 JP2008519850 A5 JP 2008519850A5 JP 2007541357 A JP2007541357 A JP 2007541357A JP 2007541357 A JP2007541357 A JP 2007541357A JP 2008519850 A5 JP2008519850 A5 JP 2008519850A5
- Authority
- JP
- Japan
- Prior art keywords
- morpholin
- group
- pyrimidine
- carboxylic acid
- substituent
- Prior art date
- 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.)
- Pending
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- 125000001424 substituent group Chemical group 0.000 claims 179
- -1 azuleneyl group Chemical group 0.000 claims 117
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000004122 cyclic group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 239000004202 carbamide Substances 0.000 claims 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- LCOWRLHONNLEGJ-UHFFFAOYSA-N 2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxylic acid Chemical compound N=1C(N2CCOCC2)=NC(C(=O)O)=CC=1OCCN1CCOCC1 LCOWRLHONNLEGJ-UHFFFAOYSA-N 0.000 claims 7
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 7
- NEFAZJJIHDDXKM-UHFFFAOYSA-N 2,3-dimethyl-1h-indol-5-amine Chemical compound C1=C(N)C=C2C(C)=C(C)NC2=C1 NEFAZJJIHDDXKM-UHFFFAOYSA-N 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000005945 imidazopyridyl group Chemical group 0.000 claims 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 4
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 108010065805 Interleukin-12 Proteins 0.000 claims 3
- 102000013462 Interleukin-12 Human genes 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- OOGPQRKICJQUCD-UHFFFAOYSA-N 2-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidine-4-carboxylic acid Chemical compound N=1C(N2CCOCC2)=NC(C(=O)O)=CC=1OCCC1=CC=CC=N1 OOGPQRKICJQUCD-UHFFFAOYSA-N 0.000 claims 2
- LGLNAQMPBACCGH-UHFFFAOYSA-N 2-morpholin-4-yl-6-[2-(2-oxo-1,3-oxazolidin-3-yl)ethoxy]pyrimidine-4-carboxylic acid Chemical compound N=1C(N2CCOCC2)=NC(C(=O)O)=CC=1OCCN1CCOC1=O LGLNAQMPBACCGH-UHFFFAOYSA-N 0.000 claims 2
- IFGCXSGJDCYJNX-UHFFFAOYSA-N 3-ethyl-1h-indol-5-amine Chemical compound C1=C(N)C=C2C(CC)=CNC2=C1 IFGCXSGJDCYJNX-UHFFFAOYSA-N 0.000 claims 2
- POYRLWQLOUUKAY-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-carbazol-3-amine Chemical compound C1CCCC2=C1NC1=CC=C(N)C=C12 POYRLWQLOUUKAY-UHFFFAOYSA-N 0.000 claims 2
- 206010065687 Bone loss Diseases 0.000 claims 2
- 239000005973 Carvone Substances 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000037147 Hypercalcaemia Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 230000000148 hypercalcaemia Effects 0.000 claims 2
- 208000030915 hypercalcemia disease Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 229940117681 interleukin-12 Drugs 0.000 claims 2
- 230000019734 interleukin-12 production Effects 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- NNRKUPYMNLJXNI-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-4,6-dimorpholin-4-ylpyridine-2-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=1)=CC(N2CCOCC2)=CC=1N1CCOCC1 NNRKUPYMNLJXNI-UHFFFAOYSA-N 0.000 claims 2
- BWSJGVKBSXUMMB-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-morpholin-4-yl-4-(2-morpholin-4-ylethoxy)pyridine-2-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=C(C=1)N2CCOCC2)=CC=1OCCN1CCOCC1 BWSJGVKBSXUMMB-UHFFFAOYSA-N 0.000 claims 2
- GNLBVDDEICCLCL-UHFFFAOYSA-N n-(3-hydroxyphenyl)-n'-[2-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidin-4-yl]oxamide Chemical compound OC1=CC=CC(NC(=O)C(=O)NC=2N=C(N=C(OCCC=3N=CC=CC=3)C=2)N2CCOCC2)=C1 GNLBVDDEICCLCL-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 210000002997 osteoclast Anatomy 0.000 claims 2
- 238000012261 overproduction Methods 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 230000035755 proliferation Effects 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000005888 tetrahydroindolyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- GBVGWHPVQBIKLE-UHFFFAOYSA-N 1-(1h-indol-5-yl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C=1C=C2NC=CC2=CC=1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 GBVGWHPVQBIKLE-UHFFFAOYSA-N 0.000 claims 1
- FWMOXLJYNWIVRP-UHFFFAOYSA-N 1-(2,3-dimethyl-1h-indol-5-yl)-3-(6-methyl-2-morpholin-4-ylpyrimidin-4-yl)urea Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)NC(N=1)=CC(C)=NC=1N1CCOCC1 FWMOXLJYNWIVRP-UHFFFAOYSA-N 0.000 claims 1
- KYODIFDANBIVQB-UHFFFAOYSA-N 1-(2,3-dimethyl-1h-indol-5-yl)-3-[2-morpholin-4-yl-6-(4-pyridin-2-ylpiperazin-1-yl)pyrimidin-4-yl]urea Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)NC(N=1)=CC(N2CCN(CC2)C=2N=CC=CC=2)=NC=1N1CCOCC1 KYODIFDANBIVQB-UHFFFAOYSA-N 0.000 claims 1
- QRKYQZBOXFRBNS-UHFFFAOYSA-N 1-(2,3-dimethyl-1h-indol-5-yl)-3-[6-[2-methoxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidin-4-yl]urea Chemical compound N=1C(N(C)CCOC)=CC(NC(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC=1N1CCOCC1 QRKYQZBOXFRBNS-UHFFFAOYSA-N 0.000 claims 1
- PKWMWKYGWUUYBT-UHFFFAOYSA-N 1-(2-bromo-4-methylphenyl)-3-[6-morpholin-4-yl-2-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]thiourea Chemical compound BrC1=CC(C)=CC=C1NC(=S)NC1=CC(N2CCOCC2)=NC(OCCN2CCOCC2)=N1 PKWMWKYGWUUYBT-UHFFFAOYSA-N 0.000 claims 1
- QDMQAJNKLTUTTP-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound ClC1=CC=CC=C1NC(=O)NC1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 QDMQAJNKLTUTTP-UHFFFAOYSA-N 0.000 claims 1
- AXNDSTYKVKENSU-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 AXNDSTYKVKENSU-UHFFFAOYSA-N 0.000 claims 1
- IDWOMFYXYMOQSB-UHFFFAOYSA-N 1-(2-methylquinolin-6-yl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=CC2=NC(C)=CC=C2C=C1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 IDWOMFYXYMOQSB-UHFFFAOYSA-N 0.000 claims 1
- SXMYRLZMSMYUQG-UHFFFAOYSA-N 1-(3-ethyl-2-methyl-1h-indol-5-yl)-3-(6-methyl-2-morpholin-4-ylpyrimidin-4-yl)urea Chemical compound C1=C2C(CC)=C(C)NC2=CC=C1NC(=O)NC(N=1)=CC(C)=NC=1N1CCOCC1 SXMYRLZMSMYUQG-UHFFFAOYSA-N 0.000 claims 1
- TYICZSKYRVGROZ-UHFFFAOYSA-N 1-(3-ethyl-2-methyl-1h-indol-5-yl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]urea Chemical compound C1=C2C(CC)=C(C)NC2=CC=C1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1NCCN1CCOCC1 TYICZSKYRVGROZ-UHFFFAOYSA-N 0.000 claims 1
- XPPCRAILQKFYIY-UHFFFAOYSA-N 1-(3-ethyl-2-methyl-1h-indol-5-yl)-3-[2-morpholin-4-yl-6-(4-pyridin-2-ylpiperazin-1-yl)pyrimidin-4-yl]urea Chemical compound C1=C2C(CC)=C(C)NC2=CC=C1NC(=O)NC(N=1)=CC(N2CCN(CC2)C=2N=CC=CC=2)=NC=1N1CCOCC1 XPPCRAILQKFYIY-UHFFFAOYSA-N 0.000 claims 1
- XGMDUACBDGDNBD-UHFFFAOYSA-N 1-(3-ethylphenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound CCC1=CC=CC(NC(=O)NC=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 XGMDUACBDGDNBD-UHFFFAOYSA-N 0.000 claims 1
- UTZLPXAPQFYMJU-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound FC1=CC=CC(NC(=O)NC=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 UTZLPXAPQFYMJU-UHFFFAOYSA-N 0.000 claims 1
- CFBIJAHDOLORFT-UHFFFAOYSA-N 1-(3-imidazol-1-ylphenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C=1C(OCCN2CCOCC2)=NC(N2CCOCC2)=NC=1NC(=O)NC(C=1)=CC=CC=1N1C=CN=C1 CFBIJAHDOLORFT-UHFFFAOYSA-N 0.000 claims 1
- NSAFPTQGZCKOIP-UHFFFAOYSA-N 1-(3-iodophenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound IC1=CC=CC(NC(=O)NC=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 NSAFPTQGZCKOIP-UHFFFAOYSA-N 0.000 claims 1
- WEVNAEBXRYANLY-UHFFFAOYSA-N 1-(3-methyl-2-oxo-1,3-benzothiazol-6-yl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=C2SC(=O)N(C)C2=CC=C1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 WEVNAEBXRYANLY-UHFFFAOYSA-N 0.000 claims 1
- VHFBJCMICNRWLB-UHFFFAOYSA-N 1-(3-methyl-2-oxo-1,3-benzoxazol-6-yl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=C2OC(=O)N(C)C2=CC=C1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 VHFBJCMICNRWLB-UHFFFAOYSA-N 0.000 claims 1
- NUGDENDMQYSEKH-UHFFFAOYSA-N 1-(3-methyl-4-propan-2-ylphenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=C(C)C(C(C)C)=CC=C1NC(=O)NC1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 NUGDENDMQYSEKH-UHFFFAOYSA-N 0.000 claims 1
- PTWHVGNAXHDUHU-UHFFFAOYSA-N 1-(3-methylphenyl)-3-[2-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidin-4-yl]urea Chemical compound CC1=CC=CC(NC(=O)NC=2N=C(N=C(OCCC=3N=CC=CC=3)C=2)N2CCOCC2)=C1 PTWHVGNAXHDUHU-UHFFFAOYSA-N 0.000 claims 1
- FATIRLHASHLSPE-UHFFFAOYSA-N 1-(3-methylphenyl)-3-[4-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidin-2-yl]urea Chemical compound CC1=CC=CC(NC(=O)NC=2N=C(C=C(OCCC=3N=CC=CC=3)N=2)N2CCOCC2)=C1 FATIRLHASHLSPE-UHFFFAOYSA-N 0.000 claims 1
- YLURRNUCWRLBPH-UHFFFAOYSA-N 1-(4,6-dimorpholin-4-ylpyridin-2-yl)-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2N=C(C=C(C=2)N2CCOCC2)N2CCOCC2)=C1 YLURRNUCWRLBPH-UHFFFAOYSA-N 0.000 claims 1
- VNMXIKHVFQCNCK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 VNMXIKHVFQCNCK-UHFFFAOYSA-N 0.000 claims 1
- BORQJTFEZSFCNQ-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=CC(O)=CC=C1NC(=O)NC1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 BORQJTFEZSFCNQ-UHFFFAOYSA-N 0.000 claims 1
- IRKHJSXVOYOTMS-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 IRKHJSXVOYOTMS-UHFFFAOYSA-N 0.000 claims 1
- NBIGGIYBBGPVDU-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[6-morpholin-4-yl-2-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]thiourea Chemical compound C1=CC(C)=CC=C1NC(=S)NC1=CC(N2CCOCC2)=NC(OCCN2CCOCC2)=N1 NBIGGIYBBGPVDU-UHFFFAOYSA-N 0.000 claims 1
- TURKESGUKANEJD-UHFFFAOYSA-N 1-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C=1C(OCCN2CCOCC2)=NC(N2CCOCC2)=NC=1NC(=O)NC(S1)=NN=C1C1CC1 TURKESGUKANEJD-UHFFFAOYSA-N 0.000 claims 1
- XEEDJKPFDDNKTA-UHFFFAOYSA-N 1-(5-hydroxynaphthalen-1-yl)-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=CC=C2C(O)=CC=CC2=C1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 XEEDJKPFDDNKTA-UHFFFAOYSA-N 0.000 claims 1
- DYHDCKIGFFEAGK-UHFFFAOYSA-N 1-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]-3-(3-propan-2-ylphenyl)urea Chemical compound CC(C)C1=CC=CC(NC(=O)NC=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 DYHDCKIGFFEAGK-UHFFFAOYSA-N 0.000 claims 1
- WRLVCELUHOKNSP-UHFFFAOYSA-N 1-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]-3-(6,7,8,9-tetrahydro-5h-carbazol-3-yl)urea Chemical compound C=1C=C2NC=3CCCCC=3C2=CC=1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 WRLVCELUHOKNSP-UHFFFAOYSA-N 0.000 claims 1
- IFBIKKSLJVOHIF-UHFFFAOYSA-N 1-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]-3-phenylurea Chemical compound C=1C(OCCN2CCOCC2)=NC(N2CCOCC2)=NC=1NC(=O)NC1=CC=CC=C1 IFBIKKSLJVOHIF-UHFFFAOYSA-N 0.000 claims 1
- FEIFWSLXLLDKOB-UHFFFAOYSA-N 1-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]-3-quinolin-5-ylurea Chemical compound C=1C=CC2=NC=CC=C2C=1NC(=O)NC(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 FEIFWSLXLLDKOB-UHFFFAOYSA-N 0.000 claims 1
- ZMBHGPZBWWMLJG-UHFFFAOYSA-N 1-[4-(4-methylphenyl)-1,3-thiazol-2-yl]-3-[2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]urea Chemical compound C1=CC(C)=CC=C1C1=CSC(NC(=O)NC=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=N1 ZMBHGPZBWWMLJG-UHFFFAOYSA-N 0.000 claims 1
- WSUWPNNRWLWQOC-UHFFFAOYSA-N 1-[6-(2-hydroxy-2-methylpropoxy)-2-morpholin-4-ylpyrimidin-4-yl]-3-(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2N=C(N=C(OCC(C)(C)O)C=2)N2CCOCC2)=C1 WSUWPNNRWLWQOC-UHFFFAOYSA-N 0.000 claims 1
- LIQYKAXRYLZVAU-UHFFFAOYSA-N 1-[6-(4-acetylpiperazin-1-yl)-2-morpholin-4-ylpyrimidin-4-yl]-3-(2,3-dimethyl-1h-indol-5-yl)urea Chemical compound C1CN(C(=O)C)CCN1C1=CC(NC(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC(N2CCOCC2)=N1 LIQYKAXRYLZVAU-UHFFFAOYSA-N 0.000 claims 1
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- NGCVEHPDYVQJGB-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-(2-methoxyethoxy)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(OCCOC)=CC(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC=1N1CCOCC1 NGCVEHPDYVQJGB-UHFFFAOYSA-N 0.000 claims 1
- TXNJUYFVQQQGLE-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-(2-methoxyethylamino)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(NCCOC)=CC(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC=1N1CCOCC1 TXNJUYFVQQQGLE-UHFFFAOYSA-N 0.000 claims 1
- BVWFYTZAPUOBSA-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-(4-hydroxypiperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=1)=CC(N2CCC(O)CC2)=NC=1N1CCOCC1 BVWFYTZAPUOBSA-UHFFFAOYSA-N 0.000 claims 1
- MUWDJWLPSSDZFP-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-(4-methylpiperazin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC(N2CCOCC2)=N1 MUWDJWLPSSDZFP-UHFFFAOYSA-N 0.000 claims 1
- QWGWWSVALVOWIS-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-(methylamino)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(NC)=CC(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC=1N1CCOCC1 QWGWWSVALVOWIS-UHFFFAOYSA-N 0.000 claims 1
- QTXSRPUYFXOHRC-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-[2-hydroxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(N(CCO)C)=CC(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC=1N1CCOCC1 QTXSRPUYFXOHRC-UHFFFAOYSA-N 0.000 claims 1
- NAHYSALBZLCFTM-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=1)=CC(N2CCN(CCO)CC2)=NC=1N1CCOCC1 NAHYSALBZLCFTM-UHFFFAOYSA-N 0.000 claims 1
- MRPIECYGFWHICL-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-[[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=C(N=1)N2CCOCC2)=CC=1NCC(=O)N1CCC(O)CC1 MRPIECYGFWHICL-UHFFFAOYSA-N 0.000 claims 1
- PNTFYIZITHQWHN-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-[[2-(4-methylpiperazin-1-yl)-2-oxoethyl]amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1CN(C)CCN1C(=O)CNC1=CC(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC(N2CCOCC2)=N1 PNTFYIZITHQWHN-UHFFFAOYSA-N 0.000 claims 1
- BDDZRZHGZSNQOV-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-[methoxy(2-morpholin-4-ylethyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C=1C(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC(N2CCOCC2)=NC=1N(OC)CCN1CCOCC1 BDDZRZHGZSNQOV-UHFFFAOYSA-N 0.000 claims 1
- FMHXOOXWOIVDNB-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-methoxy-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(OC)=CC(C(=O)NC=2C=C3C(C)=C(C)NC3=CC=2)=NC=1N1CCOCC1 FMHXOOXWOIVDNB-UHFFFAOYSA-N 0.000 claims 1
- XCHIJKWVLGRPTD-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-methyl-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=1)=CC(C)=NC=1N1CCOCC1 XCHIJKWVLGRPTD-UHFFFAOYSA-N 0.000 claims 1
- VILZEWSRZNKKPF-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-morpholin-4-yl-2-(2-pyridin-2-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=1)=CC(N2CCOCC2)=NC=1OCCC1=CC=CC=N1 VILZEWSRZNKKPF-UHFFFAOYSA-N 0.000 claims 1
- GONOACJJFGDMGS-UHFFFAOYSA-N n-(2,3-dimethyl-1h-indol-5-yl)-6-morpholin-4-ylpyridine-2-carboxamide Chemical compound C1=C2C(C)=C(C)NC2=CC=C1NC(=O)C(N=1)=CC=CC=1N1CCOCC1 GONOACJJFGDMGS-UHFFFAOYSA-N 0.000 claims 1
- CEEPDSKKLHHENW-UHFFFAOYSA-N n-(2,3-dimethylquinoxalin-6-yl)-6-[2-methoxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(N(C)CCOC)=CC(C(=O)NC=2C=C3N=C(C)C(C)=NC3=CC=2)=NC=1N1CCOCC1 CEEPDSKKLHHENW-UHFFFAOYSA-N 0.000 claims 1
- VRUNVFRTCGLUGG-UHFFFAOYSA-N n-(2,5-diethoxy-4-morpholin-4-ylphenyl)-6-[2-methoxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound CCOC=1C=C(NC(=O)C=2N=C(N=C(C=2)N(C)CCOC)N2CCOCC2)C(OCC)=CC=1N1CCOCC1 VRUNVFRTCGLUGG-UHFFFAOYSA-N 0.000 claims 1
- OWNHAPSAPRZUOI-UHFFFAOYSA-N n-(2-acetamidophenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound CC(=O)NC1=CC=CC=C1NC(=O)C1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 OWNHAPSAPRZUOI-UHFFFAOYSA-N 0.000 claims 1
- ZSVHKWNLOCPWSL-UHFFFAOYSA-N n-(2-chloropyridin-4-yl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=NC(Cl)=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 ZSVHKWNLOCPWSL-UHFFFAOYSA-N 0.000 claims 1
- BPEBMHYTKLSLAL-UHFFFAOYSA-N n-(2-methoxy-5-methylphenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound COC1=CC=C(C)C=C1NC(=O)C1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 BPEBMHYTKLSLAL-UHFFFAOYSA-N 0.000 claims 1
- APZJGOBXSUZDIO-UHFFFAOYSA-N n-(2-methyl-1,2,3,4-tetrahydroquinolin-7-yl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=C2NC(C)CCC2=CC=C1NC(=O)C(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 APZJGOBXSUZDIO-UHFFFAOYSA-N 0.000 claims 1
- UHAMTLRTSURSMP-UHFFFAOYSA-N n-(2-methyl-1,3-dioxoisoindol-5-yl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=C2C(=O)N(C)C(=O)C2=CC=C1NC(=O)C(N=C(N=1)N2CCOCC2)=CC=1OCCN1CCOCC1 UHAMTLRTSURSMP-UHFFFAOYSA-N 0.000 claims 1
- DGCPUEGADGYFMX-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2,6-dimorpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC(N2CCOCC2)=NC(N2CCOCC2)=N1 DGCPUEGADGYFMX-UHFFFAOYSA-N 0.000 claims 1
- OQKAACXYHQJGJG-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 OQKAACXYHQJGJG-UHFFFAOYSA-N 0.000 claims 1
- LQXIFKLFIOWBHM-UHFFFAOYSA-N n-(3-aminophenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound NC1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 LQXIFKLFIOWBHM-UHFFFAOYSA-N 0.000 claims 1
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- NRRDEBSSVIMAGI-UHFFFAOYSA-N n-(3-bromophenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound BrC1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 NRRDEBSSVIMAGI-UHFFFAOYSA-N 0.000 claims 1
- JMJSHQTVGAVKJV-UHFFFAOYSA-N n-(3-carbamoylphenyl)-2,6-dimorpholin-4-ylpyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=CC(NC(=O)C=2N=C(N=C(C=2)N2CCOCC2)N2CCOCC2)=C1 JMJSHQTVGAVKJV-UHFFFAOYSA-N 0.000 claims 1
- ZFAJWOOTRMMBHF-UHFFFAOYSA-N n-(3-carbamoylphenyl)-2-morpholin-4-yl-6-[2-(2-oxo-1,3-oxazolidin-3-yl)ethoxy]pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3C(OCC3)=O)C=2)N2CCOCC2)=C1 ZFAJWOOTRMMBHF-UHFFFAOYSA-N 0.000 claims 1
- QGJFBZXGEGSUIB-UHFFFAOYSA-N n-(3-chlorophenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound ClC1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 QGJFBZXGEGSUIB-UHFFFAOYSA-N 0.000 claims 1
- ZMFNKCNBCROYIG-UHFFFAOYSA-N n-(3-ethyl-1h-indol-5-yl)-2-morpholin-4-yl-6-piperidin-1-ylpyrimidine-4-carboxamide Chemical compound C1=C2C(CC)=CNC2=CC=C1NC(=O)C(N=1)=CC(N2CCCCC2)=NC=1N1CCOCC1 ZMFNKCNBCROYIG-UHFFFAOYSA-N 0.000 claims 1
- CTRMHDWGNLLPBC-UHFFFAOYSA-N n-(3-ethyl-1h-indol-5-yl)-6-(4-methylpiperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1=C2C(CC)=CNC2=CC=C1NC(=O)C(N=1)=CC(N2CCC(C)CC2)=NC=1N1CCOCC1 CTRMHDWGNLLPBC-UHFFFAOYSA-N 0.000 claims 1
- JTJLAZVVGPTBOH-UHFFFAOYSA-N n-(3-ethyl-2-methyl-1h-indol-5-yl)-6-(4-hydroxypiperidin-1-yl)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound C1=C2C(CC)=C(C)NC2=CC=C1NC(=O)C(N=1)=CC(N2CCC(O)CC2)=NC=1N1CCOCC1 JTJLAZVVGPTBOH-UHFFFAOYSA-N 0.000 claims 1
- ZKNBRZZJHJTEIL-UHFFFAOYSA-N n-(3-ethylphenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound CCC1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 ZKNBRZZJHJTEIL-UHFFFAOYSA-N 0.000 claims 1
- FELYMZIAAGRCQA-UHFFFAOYSA-N n-(3-hydroxyphenyl)-n'-[6-morpholin-4-yl-2-(2-pyridin-2-ylethoxy)pyrimidin-4-yl]oxamide Chemical compound OC1=CC=CC(NC(=O)C(=O)NC=2N=C(OCCC=3N=CC=CC=3)N=C(C=2)N2CCOCC2)=C1 FELYMZIAAGRCQA-UHFFFAOYSA-N 0.000 claims 1
- BVGWDBILMRQSRK-UHFFFAOYSA-N n-(3-methoxyphenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound COC1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 BVGWDBILMRQSRK-UHFFFAOYSA-N 0.000 claims 1
- CVPHAROCZVEDOP-UHFFFAOYSA-N n-(3-methylphenyl)-n'-[2-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidin-4-yl]oxamide Chemical compound CC1=CC=CC(NC(=O)C(=O)NC=2N=C(N=C(OCCC=3N=CC=CC=3)C=2)N2CCOCC2)=C1 CVPHAROCZVEDOP-UHFFFAOYSA-N 0.000 claims 1
- YRIVBCYPWKXWHI-UHFFFAOYSA-N n-(4,6-dimethylpyridin-2-yl)-6-[2-methoxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(N(C)CCOC)=CC(C(=O)NC=2N=C(C)C=C(C)C=2)=NC=1N1CCOCC1 YRIVBCYPWKXWHI-UHFFFAOYSA-N 0.000 claims 1
- AMKXUWRIJFGLSW-UHFFFAOYSA-N n-(4-anilinophenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound C=1C(OCCN2CCOCC2)=NC(N2CCOCC2)=NC=1C(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 AMKXUWRIJFGLSW-UHFFFAOYSA-N 0.000 claims 1
- APGXTISLBJIZCJ-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)-2-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidine-4-carboxamide Chemical compound CC1=CC=NC(NC(=O)C=2N=C(N=C(OCCC=3N=CC=CC=3)C=2)N2CCOCC2)=C1 APGXTISLBJIZCJ-UHFFFAOYSA-N 0.000 claims 1
- CYNACEYBQPTFNH-UHFFFAOYSA-N n-(4-tert-butyl-1,3-thiazol-2-yl)-6-[2-methoxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(N(C)CCOC)=CC(C(=O)NC=2SC=C(N=2)C(C)(C)C)=NC=1N1CCOCC1 CYNACEYBQPTFNH-UHFFFAOYSA-N 0.000 claims 1
- ZLWYUELEEHSBFH-UHFFFAOYSA-N n-(5,6-dimethyl-1,3-benzothiazol-2-yl)-6-[2-methoxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(N(C)CCOC)=CC(C(=O)NC=2SC3=CC(C)=C(C)C=C3N=2)=NC=1N1CCOCC1 ZLWYUELEEHSBFH-UHFFFAOYSA-N 0.000 claims 1
- GKPZSFAOXQKHQQ-UHFFFAOYSA-N n-(5-carbamoylpyridin-2-yl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1NC(=O)C1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 GKPZSFAOXQKHQQ-UHFFFAOYSA-N 0.000 claims 1
- JESDGWHVKMXCLF-UHFFFAOYSA-N n-(5-methyl-1,2-oxazol-3-yl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound O1C(C)=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=N1 JESDGWHVKMXCLF-UHFFFAOYSA-N 0.000 claims 1
- XEISHXARYBOMLY-UHFFFAOYSA-N n-(5-methyl-2-nitrophenyl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound CC1=CC=C([N+]([O-])=O)C(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 XEISHXARYBOMLY-UHFFFAOYSA-N 0.000 claims 1
- HIFMBBZUEARZFA-UHFFFAOYSA-N n-(6-methyl-1,3-benzothiazol-2-yl)-2-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidine-4-carboxamide Chemical compound S1C2=CC(C)=CC=C2N=C1NC(=O)C(N=C(N=1)N2CCOCC2)=CC=1OCCC1=CC=CC=N1 HIFMBBZUEARZFA-UHFFFAOYSA-N 0.000 claims 1
- VMNPDOGVIKNSDM-UHFFFAOYSA-N n-(6-methylpyridin-3-yl)-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=NC(C)=CC=C1NC(=O)C1=CC(OCCN2CCOCC2)=NC(N2CCOCC2)=N1 VMNPDOGVIKNSDM-UHFFFAOYSA-N 0.000 claims 1
- SGAIVXJPHFMVAW-UHFFFAOYSA-N n-(9-ethylcarbazol-2-yl)-2-morpholin-4-yl-6-(2-pyridin-2-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=C2N(CC)C3=CC=CC=C3C2=CC=C1NC(=O)C(N=C(N=1)N2CCOCC2)=CC=1OCCC1=CC=CC=N1 SGAIVXJPHFMVAW-UHFFFAOYSA-N 0.000 claims 1
- RLNZPMKINQTXEQ-UHFFFAOYSA-N n-[3-(2-methylpyrimidin-4-yl)phenyl]-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound CC1=NC=CC(C=2C=C(NC(=O)C=3N=C(N=C(OCCN4CCOCC4)C=3)N3CCOCC3)C=CC=2)=N1 RLNZPMKINQTXEQ-UHFFFAOYSA-N 0.000 claims 1
- HSEDGKVUDQIODT-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound CCN(CC)C1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 HSEDGKVUDQIODT-UHFFFAOYSA-N 0.000 claims 1
- WGSWYQGCASIRDJ-UHFFFAOYSA-N n-[3-(dimethylamino)-4-fluorophenyl]-6-[2-methoxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(N(C)CCOC)=CC(C(=O)NC=2C=C(C(F)=CC=2)N(C)C)=NC=1N1CCOCC1 WGSWYQGCASIRDJ-UHFFFAOYSA-N 0.000 claims 1
- PTGFJZZQJLLOCI-UHFFFAOYSA-N n-[3-(dimethylamino)-4-methylphenyl]-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound C1=C(C)C(N(C)C)=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 PTGFJZZQJLLOCI-UHFFFAOYSA-N 0.000 claims 1
- QBFRLKWOCWTFEA-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]-2,6-dimorpholin-4-ylpyrimidine-4-carboxamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=2N=C(N=C(C=2)N2CCOCC2)N2CCOCC2)=C1 QBFRLKWOCWTFEA-UHFFFAOYSA-N 0.000 claims 1
- XPHMSDLLSRSGLI-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]-2-morpholin-4-yl-6-(2-morpholin-4-ylethoxy)pyrimidine-4-carboxamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=2N=C(N=C(OCCN3CCOCC3)C=2)N2CCOCC2)=C1 XPHMSDLLSRSGLI-UHFFFAOYSA-N 0.000 claims 1
- ZIQJUAKXBHRDMA-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]-6-(2-hydroxyethoxy)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=2N=C(N=C(OCCO)C=2)N2CCOCC2)=C1 ZIQJUAKXBHRDMA-UHFFFAOYSA-N 0.000 claims 1
- HDNMNDFZKGYSHI-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]-6-(methoxyamino)-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound N=1C(NOC)=CC(C(=O)NC=2C=C(C=CC=2)N(C)C)=NC=1N1CCOCC1 HDNMNDFZKGYSHI-UHFFFAOYSA-N 0.000 claims 1
- MJSKCXPVLMZALQ-UHFFFAOYSA-N n-[3-(dimethylamino)phenyl]-6-[2-hydroxyethyl(methyl)amino]-2-morpholin-4-ylpyrimidine-4-carboxamide Chemical compound CN(C)C1=CC=CC(NC(=O)C=2N=C(N=C(C=2)N(C)CCO)N2CCOCC2)=C1 MJSKCXPVLMZALQ-UHFFFAOYSA-N 0.000 claims 1
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| US20050176767A1 (en) * | 2003-10-30 | 2005-08-11 | Laval Chan Chun Kong | Pyridine carboxamide and methods for inhibiting HIV integrase |
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| AU2004289304A1 (en) | 2003-11-10 | 2005-05-26 | Synta Pharmaceuticals, Corp. | Pyridine compounds |
| TW200616974A (en) * | 2004-07-01 | 2006-06-01 | Astrazeneca Ab | Chemical compounds |
| EP1765325A4 (en) | 2004-07-01 | 2009-08-12 | Synta Pharmaceuticals Corp | HETEROARYL COMPOUNDS SUBSTITUTED IN 2 |
| EP1819341A4 (en) * | 2004-11-10 | 2011-06-29 | Synta Pharmaceuticals Corp | IL-12 MODULATORY CONNECTIONS |
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-
2005
- 2005-11-10 EP EP05820870A patent/EP1819341A4/en not_active Withdrawn
- 2005-11-10 US US11/272,509 patent/US7696202B2/en active Active
- 2005-11-10 JP JP2007541357A patent/JP2008519850A/ja active Pending
- 2005-11-10 AU AU2005304393A patent/AU2005304393B2/en not_active Ceased
- 2005-11-10 CA CA002586870A patent/CA2586870A1/en not_active Abandoned
- 2005-11-10 TW TW094139373A patent/TW200628159A/zh unknown
- 2005-11-10 WO PCT/US2005/040952 patent/WO2006053227A2/en not_active Ceased
-
2010
- 2010-03-24 US US12/731,056 patent/US8236795B2/en not_active Expired - Lifetime
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