JP5592360B2 - イミダゾピリミジノンおよびその使用 - Google Patents

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Publication number

JP5592360B2

JP5592360B2 JP2011515027A JP2011515027A JP5592360B2 JP 5592360 B2 JP5592360 B2 JP 5592360B2 JP 2011515027 A JP2011515027 A JP 2011515027A JP 2011515027 A JP2011515027 A JP 2011515027A JP 5592360 B2 JP5592360 B2 JP 5592360B2

Authority

JP

Japan

Prior art keywords

alkyl

alkylene

group

product

oxo

Prior art date

2008-07-02

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.)

Expired - Fee Related

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• BOUNFBOFBGBYBT-UHFFFAOYSA-N purin-8-one Chemical compound C1=NC=NC2=NC(=O)N=C21 BOUNFBOFBGBYBT-UHFFFAOYSA-N 0.000 title 1
• -1 NR 3 R 4 Chemical group 0.000 claims description 143
• 125000000217 alkyl group Chemical group 0.000 claims description 117
• 150000001875 compounds Chemical class 0.000 claims description 110
• 125000002947 alkylene group Chemical group 0.000 claims description 64
• 229910052717 sulfur Inorganic materials 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 52
• 125000004432 carbon atom Chemical group C* 0.000 claims description 42
• 150000003839 salts Chemical class 0.000 claims description 39
• 238000004519 manufacturing process Methods 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 125000005843 halogen group Chemical group 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 28
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
• 239000001257 hydrogen Substances 0.000 claims description 24
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000005842 heteroatom Chemical group 0.000 claims description 23
• 241000700605 Viruses Species 0.000 claims description 22
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 21
• 230000035772 mutation Effects 0.000 claims description 20
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 208000015181 infectious disease Diseases 0.000 claims description 14
• 230000003647 oxidation Effects 0.000 claims description 14
• 238000007254 oxidation reaction Methods 0.000 claims description 14
• 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 208000036142 Viral infection Diseases 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 230000009385 viral infection Effects 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 108010002459 HIV Integrase Proteins 0.000 claims description 8
• 229940124524 integrase inhibitor Drugs 0.000 claims description 8
• 239000002850 integrase inhibitor Substances 0.000 claims description 8
• CZFFBEXEKNGXKS-UHFFFAOYSA-N raltegravir Chemical compound O1C(C)=NN=C1C(=O)NC(C)(C)C1=NC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(=O)N1C CZFFBEXEKNGXKS-UHFFFAOYSA-N 0.000 claims description 8
• 229960004742 raltegravir Drugs 0.000 claims description 8
• 229940124530 sulfonamide Drugs 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 7
• 102220076678 rs146651027 Human genes 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 230000002265 prevention Effects 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
• 150000003951 lactams Chemical class 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical group C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 2
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
• 150000003536 tetrazoles Chemical group 0.000 claims description 2
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
• 150000003852 triazoles Chemical group 0.000 claims description 2
• 239000000047 product Substances 0.000 description 256
• 238000002360 preparation method Methods 0.000 description 138
• 239000000203 mixture Substances 0.000 description 104
• 238000000034 method Methods 0.000 description 103
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
• 239000000243 solution Substances 0.000 description 55
• 230000008569 process Effects 0.000 description 31
• 239000007787 solid Substances 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
• 238000004440 column chromatography Methods 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• 239000002253 acid Substances 0.000 description 26
• 239000000460 chlorine Substances 0.000 description 25
• 235000019439 ethyl acetate Nutrition 0.000 description 24
• 239000012267 brine Substances 0.000 description 22
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• 102100034343 Integrase Human genes 0.000 description 21
• 210000004027 cell Anatomy 0.000 description 21
• 238000004128 high performance liquid chromatography Methods 0.000 description 21
• 108010061833 Integrases Proteins 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 230000003612 virological effect Effects 0.000 description 18
• 241000725303 Human immunodeficiency virus Species 0.000 description 17
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
• 238000006243 chemical reaction Methods 0.000 description 17
• 230000002829 reductive effect Effects 0.000 description 17
• 108020004414 DNA Proteins 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 238000003556 assay Methods 0.000 description 15
• 238000001212 derivatisation Methods 0.000 description 14
• 230000000694 effects Effects 0.000 description 14
• 239000000651 prodrug Substances 0.000 description 14
• 229940002612 prodrug Drugs 0.000 description 14
• 239000012043 crude product Substances 0.000 description 13
• 239000000284 extract Substances 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• 150000002148 esters Chemical class 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000011541 reaction mixture Substances 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• 239000011734 sodium Substances 0.000 description 10
• 229910052938 sodium sulfate Inorganic materials 0.000 description 10
• 235000011152 sodium sulphate Nutrition 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
• 238000001816 cooling Methods 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 7
• 230000010354 integration Effects 0.000 description 7
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• UHDHWOXRBRJTDM-UHFFFAOYSA-N 2-(aminomethyl)-5-fluoro-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC(F)=CC=C1CN UHDHWOXRBRJTDM-UHFFFAOYSA-N 0.000 description 6
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• 239000003480 eluent Substances 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• 230000001404 mediated effect Effects 0.000 description 6
• BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 5
• HLIPNOCMUMHICC-UHFFFAOYSA-N 1-methyl-5-oxo-6-phenylmethoxyimidazo[1,2-a]pyrimidine-7-carboxylic acid Chemical compound CN1C=CN(C2=O)C1=NC(C(O)=O)=C2OCC1=CC=CC=C1 HLIPNOCMUMHICC-UHFFFAOYSA-N 0.000 description 5
• 108091026890 Coding region Proteins 0.000 description 5
• 102000004190 Enzymes Human genes 0.000 description 5
• 108090000790 Enzymes Proteins 0.000 description 5
• 208000031886 HIV Infections Diseases 0.000 description 5
• 241000713772 Human immunodeficiency virus 1 Species 0.000 description 5
• 125000001309 chloro group Chemical group Cl* 0.000 description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000005457 ice water Substances 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• 150000004702 methyl esters Chemical class 0.000 description 5
• 230000001566 pro-viral effect Effects 0.000 description 5
• 239000013605 shuttle vector Substances 0.000 description 5
• IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 4
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 4
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
• 108060001084 Luciferase Proteins 0.000 description 4
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• BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
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• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 3
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 3
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• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 3
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• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
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• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• 125000000539 amino acid group Chemical group 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
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• YJWGTNTYXLSYLM-UHFFFAOYSA-N methyl 2-(2-bromo-3-oxopropyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CC(Br)C=O YJWGTNTYXLSYLM-UHFFFAOYSA-N 0.000 description 1
• KQGQYJKAKSNBNF-UHFFFAOYSA-N methyl 2-(3-oxopropyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CCC=O KQGQYJKAKSNBNF-UHFFFAOYSA-N 0.000 description 1
• UDAQKNASVOYTOL-UHFFFAOYSA-N methyl 2-[[2-[1-[2-(2,6-dimethylmorpholin-4-yl)-2-oxoethyl]-5-oxo-6-phenylmethoxyimidazo[1,2-a]pyrimidin-7-yl]-1,3-thiazol-5-yl]methyl]-5-fluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1CC1=CN=C(C2=C(C(=O)N3C=CN(CC(=O)N4CC(C)OC(C)C4)C3=N2)OCC=2C=CC=CC=2)S1 UDAQKNASVOYTOL-UHFFFAOYSA-N 0.000 description 1
• BXXLTVBTDZXPTN-UHFFFAOYSA-N methyl 2-iodobenzoate Chemical compound COC(=O)C1=CC=CC=C1I BXXLTVBTDZXPTN-UHFFFAOYSA-N 0.000 description 1
• NJSGAMILODSGLG-UHFFFAOYSA-N methyl 3-(4-fluoro-2-methylsulfanylphenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(F)C=C1SC NJSGAMILODSGLG-UHFFFAOYSA-N 0.000 description 1
• UTEMHQAGNZTRMZ-UHFFFAOYSA-N methyl 3-(4-fluoro-2-methylsulfonylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(F)C=C1S(C)(=O)=O UTEMHQAGNZTRMZ-UHFFFAOYSA-N 0.000 description 1
• RYOUZCHYIRLCGR-UHFFFAOYSA-N methyl 3-(4-fluoro-2-morpholin-4-ylsulfonylphenyl)prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(F)C=C1S(=O)(=O)N1CCOCC1 RYOUZCHYIRLCGR-UHFFFAOYSA-N 0.000 description 1
• WUJSMHUCQVMXJF-UHFFFAOYSA-N methyl 3-(4-fluoro-2-morpholin-4-ylsulfonylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(F)C=C1S(=O)(=O)N1CCOCC1 WUJSMHUCQVMXJF-UHFFFAOYSA-N 0.000 description 1
• OLPQEVGZOOVHBX-UHFFFAOYSA-N methyl 3-[2-(dimethylsulfamoyl)-4-fluorophenyl]prop-2-enoate Chemical compound COC(=O)C=CC1=CC=C(F)C=C1S(=O)(=O)N(C)C OLPQEVGZOOVHBX-UHFFFAOYSA-N 0.000 description 1
• LCBPJEAOIOQKOE-UHFFFAOYSA-N methyl 3-[2-(dimethylsulfamoyl)-4-fluorophenyl]propanoate Chemical compound COC(=O)CCC1=CC=C(F)C=C1S(=O)(=O)N(C)C LCBPJEAOIOQKOE-UHFFFAOYSA-N 0.000 description 1
• LJKQVZJYOJLFGR-UHFFFAOYSA-N methyl 5-fluoro-2-(3-oxopropyl)benzoate Chemical compound COC(=O)C1=CC(F)=CC=C1CCC=O LJKQVZJYOJLFGR-UHFFFAOYSA-N 0.000 description 1
• DTIWOKISOJGBOZ-UHFFFAOYSA-N methyl 5-oxo-6-phenylmethoxy-1-(1,3-thiazol-2-ylmethyl)imidazo[1,2-a]pyrimidine-7-carboxylate Chemical compound C1=CN2C(=O)C(OCC=3C=CC=CC=3)=C(C(=O)OC)N=C2N1CC1=NC=CS1 DTIWOKISOJGBOZ-UHFFFAOYSA-N 0.000 description 1
• YBVVHHULAHCSJO-UHFFFAOYSA-N methyl 6-acetyloxy-1-[2-(2-methylpiperidin-1-yl)-2-oxoethyl]-5-oxoimidazo[1,2-a]pyrimidine-7-carboxylate Chemical compound C1=CN2C(=O)C(OC(C)=O)=C(C(=O)OC)N=C2N1CC(=O)N1CCCCC1C YBVVHHULAHCSJO-UHFFFAOYSA-N 0.000 description 1
• FKFMMVNYDCXYEB-UHFFFAOYSA-N methyl 6-acetyloxy-1-[2-(3,5-dimethylpiperidin-1-yl)-2-oxoethyl]-5-oxoimidazo[1,2-a]pyrimidine-7-carboxylate Chemical compound C1=CN2C(=O)C(OC(C)=O)=C(C(=O)OC)N=C2N1CC(=O)N1CC(C)CC(C)C1 FKFMMVNYDCXYEB-UHFFFAOYSA-N 0.000 description 1
• ACDPPMLZDOJFIA-UHFFFAOYSA-N methyl 6-acetyloxy-3-bromo-1-[2-(2,6-dimethylmorpholin-4-yl)-2-oxoethyl]-5-oxoimidazo[1,2-a]pyrimidine-7-carboxylate Chemical compound C1=C(Br)N2C(=O)C(OC(C)=O)=C(C(=O)OC)N=C2N1CC(=O)N1CC(C)OC(C)C1 ACDPPMLZDOJFIA-UHFFFAOYSA-N 0.000 description 1
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