JPH052670B2 - - Google Patents

Info

Publication number: JPH052670B2
Authority: JP; Japan
Prior art keywords: compound according; amino; pyrimidinol; iodo; bromo
Prior art date: 1979-03-19
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 - Lifetime

Application number

JP55035729A

Other languages

English (en)

Japanese (ja)

Other versions

JPS55127378A (en

Inventor

Uiirenga Uenderu

Aabingu Sukarunitsuku Haabei

Aran Sutoringufueroo Deeru

Iburin Fuaasuto Patorishia

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

Priority date (The priority date 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 date listed.)

1979-03-19

Filing date

1980-03-19

Publication date

1993-01-13

1980-03-19 Application filed by Upjohn Co filed Critical Upjohn Co

1980-10-02 Publication of JPS55127378A publication Critical patent/JPS55127378A/ja

1993-01-13 Publication of JPH052670B2 publication Critical patent/JPH052670B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 45
-1 monosubstituted phenyl Chemical group 0.000 claims description 32
125000004432 carbon atom Chemical group C* 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
150000002431 hydrogen Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000001153 fluoro group Chemical group F* 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000002346 iodo group Chemical group I* 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
LOQWIXAMWLMCQY-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC(F)=C1 LOQWIXAMWLMCQY-UHFFFAOYSA-N 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
CFQSIYDPHWZRTM-UHFFFAOYSA-N F[Br]Cl Chemical compound F[Br]Cl CFQSIYDPHWZRTM-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims 2
UHKUZWMIMIJLAZ-UHFFFAOYSA-N 2-amino-5-bromo-6-(2-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC=C1F UHKUZWMIMIJLAZ-UHFFFAOYSA-N 0.000 claims 1
MZYSYNKAXMNKDO-UHFFFAOYSA-N 2-amino-5-bromo-6-(2-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC=C1C1=C(Br)C(=O)N=C(N)N1 MZYSYNKAXMNKDO-UHFFFAOYSA-N 0.000 claims 1
DPRPYFUMFSDKEY-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-chlorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC(Cl)=C1 DPRPYFUMFSDKEY-UHFFFAOYSA-N 0.000 claims 1
QKSGRZHBGJWOBN-UHFFFAOYSA-N 2-amino-5-bromo-6-(3-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)N=C(N)N2)Br)=C1 QKSGRZHBGJWOBN-UHFFFAOYSA-N 0.000 claims 1
FFHKBAKFBGNHID-UHFFFAOYSA-N 2-amino-5-bromo-6-(4-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=C(F)C=C1 FFHKBAKFBGNHID-UHFFFAOYSA-N 0.000 claims 1
RUGYFOOEFABCJN-UHFFFAOYSA-N 2-amino-5-bromo-6-[3-(2-ethoxyethoxy)phenyl]-1h-pyrimidin-4-one Chemical compound CCOCCOC1=CC=CC(C2=C(C(=O)N=C(N)N2)Br)=C1 RUGYFOOEFABCJN-UHFFFAOYSA-N 0.000 claims 1
HOUWQEYUQCSILM-UHFFFAOYSA-N 2-amino-5-bromo-6-naphthalen-1-yl-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC2=CC=CC=C12 HOUWQEYUQCSILM-UHFFFAOYSA-N 0.000 claims 1
WCWMVUUWTZVWHC-UHFFFAOYSA-N 2-amino-5-bromo-6-pyridin-2-yl-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Br)=C1C1=CC=CC=N1 WCWMVUUWTZVWHC-UHFFFAOYSA-N 0.000 claims 1
SYGWERHRFAGJCA-UHFFFAOYSA-N 2-amino-5-chloro-6-(2-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC=C1F SYGWERHRFAGJCA-UHFFFAOYSA-N 0.000 claims 1
SDNLXFAKPKNJRE-UHFFFAOYSA-N 2-amino-5-chloro-6-(2-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC=C1C1=C(Cl)C(=O)N=C(N)N1 SDNLXFAKPKNJRE-UHFFFAOYSA-N 0.000 claims 1
SHRZUNZYCBOEBR-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-chlorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC(Cl)=C1 SHRZUNZYCBOEBR-UHFFFAOYSA-N 0.000 claims 1
YFIFDYUYUNDVSO-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-fluorophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC(F)=C1 YFIFDYUYUNDVSO-UHFFFAOYSA-N 0.000 claims 1
RFNDUVABMSOPRX-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)N=C(N)N2)Cl)=C1 RFNDUVABMSOPRX-UHFFFAOYSA-N 0.000 claims 1
JDGIGSRWNIWEDC-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-nitrophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(Cl)=C1C1=CC=CC([N+]([O-])=O)=C1 JDGIGSRWNIWEDC-UHFFFAOYSA-N 0.000 claims 1
SUGLSVRAIXNUJC-UHFFFAOYSA-N 2-amino-5-chloro-6-(3-propoxyphenyl)-1h-pyrimidin-4-one Chemical compound CCCOC1=CC=CC(C2=C(C(=O)N=C(N)N2)Cl)=C1 SUGLSVRAIXNUJC-UHFFFAOYSA-N 0.000 claims 1
OTYQGLBBGSZIKY-UHFFFAOYSA-N 2-amino-5-iodo-6-(2-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC=C1C1=C(I)C(=O)N=C(N)N1 OTYQGLBBGSZIKY-UHFFFAOYSA-N 0.000 claims 1
ZUBOQFMGNULWCW-UHFFFAOYSA-N 2-amino-5-iodo-6-(3-methoxyphenyl)-1h-pyrimidin-4-one Chemical compound COC1=CC=CC(C2=C(C(=O)N=C(N)N2)I)=C1 ZUBOQFMGNULWCW-UHFFFAOYSA-N 0.000 claims 1
VXTXTXSPZIZKTK-UHFFFAOYSA-N 2-amino-5-iodo-6-(3-nitrophenyl)-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(I)=C1C1=CC=CC([N+]([O-])=O)=C1 VXTXTXSPZIZKTK-UHFFFAOYSA-N 0.000 claims 1
STOMVMLFBPMGFN-UHFFFAOYSA-N 2-amino-5-iodo-6-[3-(trifluoromethyl)phenyl]-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(I)=C1C1=CC=CC(C(F)(F)F)=C1 STOMVMLFBPMGFN-UHFFFAOYSA-N 0.000 claims 1
UJOZREWWJGVFCU-UHFFFAOYSA-N 2-amino-6-(2-fluorophenyl)-5-iodo-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(I)=C1C1=CC=CC=C1F UJOZREWWJGVFCU-UHFFFAOYSA-N 0.000 claims 1
ANNSJLJZORKOJG-UHFFFAOYSA-N 2-amino-6-(3-bromophenyl)-5-iodo-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(I)=C1C1=CC=CC(Br)=C1 ANNSJLJZORKOJG-UHFFFAOYSA-N 0.000 claims 1
DXBYKELYJFUZHI-UHFFFAOYSA-N 2-amino-6-(3-chlorophenyl)-5-iodo-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(I)=C1C1=CC=CC(Cl)=C1 DXBYKELYJFUZHI-UHFFFAOYSA-N 0.000 claims 1
OKNMQQVSQSQFEN-UHFFFAOYSA-N 2-amino-6-(3-fluorophenyl)-5-iodo-1h-pyrimidin-4-one Chemical compound N1C(N)=NC(=O)C(I)=C1C1=CC=CC(F)=C1 OKNMQQVSQSQFEN-UHFFFAOYSA-N 0.000 claims 1
SBUKLPSBNFWJCU-UHFFFAOYSA-N ClIBr Chemical compound ClIBr SBUKLPSBNFWJCU-UHFFFAOYSA-N 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
238000004519 manufacturing process Methods 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 18
239000007787 solid Substances 0.000 description 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
238000000034 method Methods 0.000 description 10
HGINADPHJQTSKN-UHFFFAOYSA-M 3-ethoxy-3-oxopropanoate Chemical compound CCOC(=O)CC([O-])=O HGINADPHJQTSKN-UHFFFAOYSA-M 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000000463 material Substances 0.000 description 7
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 6
230000000840 anti-viral effect Effects 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000002585 base Substances 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
150000003230 pyrimidines Chemical class 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000002002 slurry Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
102100023849 Glycophorin-C Human genes 0.000 description 4
101100229307 Homo sapiens GYPC gene Proteins 0.000 description 4
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 4
XCLDSQRVMMXWMS-UHFFFAOYSA-N ethyl 4-methyl-3-oxopentanoate Chemical compound CCOC(=O)CC(=O)C(C)C XCLDSQRVMMXWMS-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000005010 perfluoroalkyl group Chemical group 0.000 description 4
238000003756 stirring Methods 0.000 description 4
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
101000722960 Onchocerca volvulus Onchocystatin Proteins 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
230000016396 cytokine production Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
DGCZHKABHPDNCC-UHFFFAOYSA-N ethyl 3-(4-chlorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)C=C1 DGCZHKABHPDNCC-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
PRRBQHNMYJRHFW-UHFFFAOYSA-M 3-oxoheptanoate Chemical compound CCCCC(=O)CC([O-])=O PRRBQHNMYJRHFW-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
208000036142 Viral infection Diseases 0.000 description 2
WRQMAGMYXHWRRQ-UHFFFAOYSA-N acetyl 2-ethyl-4-methoxybenzoate Chemical compound CCC1=CC(OC)=CC=C1C(=O)OC(C)=O WRQMAGMYXHWRRQ-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
NZRZNJONGRRTNF-UHFFFAOYSA-N ethyl 2-benzoylbutanoate Chemical compound CCOC(=O)C(CC)C(=O)C1=CC=CC=C1 NZRZNJONGRRTNF-UHFFFAOYSA-N 0.000 description 2
BOZNWXQZCYZCSH-UHFFFAOYSA-N ethyl 3-oxo-4-phenylbutanoate Chemical compound CCOC(=O)CC(=O)CC1=CC=CC=C1 BOZNWXQZCYZCSH-UHFFFAOYSA-N 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
230000026045 iodination Effects 0.000 description 2
238000006192 iodination reaction Methods 0.000 description 2
239000010410 layer Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000009385 viral infection Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical compound NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 description 1
ADLWOFHKMXUDKF-UHFFFAOYSA-N 2-amino-5-bromo-6-methyl-1h-pyrimidin-4-one Chemical compound CC=1NC(N)=NC(=O)C=1Br ADLWOFHKMXUDKF-UHFFFAOYSA-N 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 1
JKQFDNYBLVSFRW-UHFFFAOYSA-N 5-bromo-2-(dimethylamino)-6-methyl-1h-pyrimidin-4-one Chemical compound CN(C)C1=NC(C)=C(Br)C(O)=N1 JKQFDNYBLVSFRW-UHFFFAOYSA-N 0.000 description 1
DNWRLMRKDSGSPL-UHFFFAOYSA-N 5-iodopyrimidine Chemical compound IC1=CN=CN=C1 DNWRLMRKDSGSPL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CIUUIPMOFZIWIZ-UHFFFAOYSA-N Bropirimine Chemical compound NC1=NC(O)=C(Br)C(C=2C=CC=CC=2)=N1 CIUUIPMOFZIWIZ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 1
DIGGWMOTBUMCTG-UHFFFAOYSA-N P.[C] Chemical compound P.[C] DIGGWMOTBUMCTG-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
BAOWVDHYZBLYMB-UHFFFAOYSA-N [F].C1=CC=NC=C1 Chemical compound [F].C1=CC=NC=C1 BAOWVDHYZBLYMB-UHFFFAOYSA-N 0.000 description 1
XWVQUTJNAVUFRL-UHFFFAOYSA-N acetyl 2-ethyl-6-methylbenzoate Chemical compound CCC1=CC=CC(C)=C1C(=O)OC(C)=O XWVQUTJNAVUFRL-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
SIWICBKMMHBCSU-UHFFFAOYSA-N ethyl 3-(3,4-dichlorophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)C(Cl)=C1 SIWICBKMMHBCSU-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000003682 fluorination reaction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
TYRDEZUMAVRTEO-UHFFFAOYSA-N pyrimidin-5-ylmethanol Chemical compound OCC1=CN=CN=C1 TYRDEZUMAVRTEO-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000012546 transfer Methods 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000001665 trituration Methods 0.000 description 1
210000002700 urine Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Tropical Medicine & Parasitology (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP3572980A 1979-03-19 1980-03-19 66arylpyrimidines Granted JPS55127378A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US2220579A	1979-03-19	1979-03-19

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3201754A Division JPH0627070B2 (ja)	1979-03-19	1991-08-12	ウイルス感染の予防治療およびインターフェロン生成誘導用医薬組成物

Publications (2)

Publication Number	Publication Date
JPS55127378A JPS55127378A (en)	1980-10-02
JPH052670B2 true JPH052670B2 (fr)	1993-01-13

Family

ID=21808376

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3572980A Granted JPS55127378A (en)	1979-03-19	1980-03-19	66arylpyrimidines

Country Status (2)

Country	Link
JP (1)	JPS55127378A (fr)
BE (1)	BE882315A (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4507302A (en) *	1979-03-19	1985-03-26	The Upjohn Company	Method for treating arthritis with 6-aryl pyrimidine compounds
US5554617A (en) *	1979-09-28	1996-09-10	The Upjohn Company	Method for treating cancer with 6-aryl pyrimidine compounds
US4460589A (en) *	1980-10-03	1984-07-17	The Upjohn Company	Process for treating hypertension
US4593096A (en) *	1982-06-09	1986-06-03	The Upjohn Company	Novel compounds and process for treating hypertension
US4578466A (en) *	1983-07-11	1986-03-25	The Upjohn Company	Processes for the preparation of 6-aryluracils
US4495349A (en) *	1983-07-11	1985-01-22	The Upjohn Company	6-Aryluracils
US4593030A (en) *	1983-07-11	1986-06-03	The Upjohn Company	Use of 6-aryluracils as antiinflammatory and antiarthritic agents
US4625028A (en) *	1983-07-11	1986-11-25	The Upjohn Company	6-aryluracils and selected novel intermediates used in the preparation thereof
US4521599A (en) *	1983-07-11	1985-06-04	The Upjohn Company	Process for the preparation of 1,3-oxazine-4-ones
WO2001068613A1 (fr) *	2000-03-17	2001-09-20	Nissan Chemical Industries, Ltd.	Dérivés pyrimidinone et herbicides

1980
- 1980-03-19 JP JP3572980A patent/JPS55127378A/ja active Granted
- 1980-03-19 BE BE0/199861A patent/BE882315A/fr not_active IP Right Cessation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF THE CHEMICAL SOCIETY RERKIN TRANSACTIONS 1=1975 *

Also Published As

Publication number	Publication date
JPS55127378A (en)	1980-10-02
BE882315A (fr)	1980-09-19

Publication	Publication Date	Title
HU213186B (en)	1997-03-28	Process for the preparation of fenoxy-pyrimidine derivatives
JPH04502473A (ja)	1992-05-07	ヘテロ環式化合物
JPH052670B2 (fr)	1993-01-13
CZ301563B6 (cs)	2010-04-14	Zpusob prípravy pyrrolopyrimidinových derivátu
JPH0140830B2 (fr)	1989-08-31
Southwick et al.	1949	The Ring Closure of N-Alkoxalyl-β-anilinopropionic Acids
HU185982B (en)	1985-04-28	Process for producing 1,dihydro-3h-pyrrolo-bracket-1,2-a-bracket closed-pyrolle-1-carboxylic acids and esters thereof
EP0150996B1 (fr)	1988-01-07	Préparation des dérivés d'acide heptanoique
JPS634544B2 (fr)	1988-01-29
JP3252502B2 (ja)	2002-02-04	Ｎ−５保護した２，５−ジアミノ−４，６−ジクロロピリミジンおよびその製造方法
JP2780843B2 (ja)	1998-07-30	プリニルおよびピリミジニルテトラヒドロフラン類
JP4026233B2 (ja)	2007-12-26	４，５−ジクロロ−６−（α−フルオロアルキル）ピリミジンの製法
JPH05194423A (ja)	1993-08-03	２−置換−４，６−ジアルコキシピリミジンの製造方法
US2344459A (en)	1944-03-14	Method of preparing i
JPH01299272A (ja)	1989-12-04	置換ピリジン類の製造方法
JPS6243993B2 (fr)	1987-09-17
SU900810A3 (ru)	1982-01-23	Способ получени 4-арилхиназолин-2/1н/-онов
JPH0522709B2 (fr)	1993-03-30
KR850000096B1 (ko)	1985-02-22	5-치환된 디 알루르산의 제조방법
JPH083143A (ja)	1996-01-09	６−アラルキル置換ピリミジン誘導体の製造方法
Dimsdale	1979	The formation of 2‐alkoxyquinolines from quinoline N‐oxides in alcoholic media
US3703597A (en)	1972-11-21	Preparation of benzilic acid compounds
Whale et al.	1992	The synthesis of 5-substituted-2, 4-dimethoxypyrimidines and some related nucleoside analogues
US2698846A (en)	1955-01-04	Heterocyclic compounds
Cheney et al.	1945	Some Tetrahydrothiophene β-Keto Ester Derivatives