NO812431L - Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-2-on-derivater. - Google Patents

Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-2-on-derivater.

Info

Publication number: NO812431L
Authority: NO; Norway
Prior art keywords: group; formula; compounds; compound; chloro
Prior art date: 1980-07-15

Application number

NO812431A

Other languages

English (en)

Norwegian (no)

Inventor

Gordon Hanley Phillipps

Christopher Williamson

Original Assignee

Glaxo Group Ltd

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.)

1980-07-15

Filing date

1981-07-15

Publication date

1982-01-18

1981-07-15 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1982-01-18 Publication of NO812431L publication Critical patent/NO812431L/no

Links

238000000034 method Methods 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims description 9
VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title description 28
230000001225 therapeutic effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 67
150000003839 salts Chemical class 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000005843 halogen group Chemical group 0.000 claims abstract description 8
230000002378 acidificating effect Effects 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
125000000468 ketone group Chemical group 0.000 claims abstract description 5
238000003683 electrophilic halogenation reaction Methods 0.000 claims abstract description 3
-1 hydroxyl- Chemical group 0.000 claims description 39
239000003795 chemical substances by application Substances 0.000 claims description 22
OCSYCDVQABSEPJ-UHFFFAOYSA-N 5-chloro-1h-pyrimidin-2-one Chemical compound OC1=NC=C(Cl)C=N1 OCSYCDVQABSEPJ-UHFFFAOYSA-N 0.000 claims description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 4
125000002843 carboxylic acid group Chemical group 0.000 claims description 3
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims 2
125000002837 carbocyclic group Chemical group 0.000 claims 1
230000002159 abnormal effect Effects 0.000 abstract description 16
230000031864 metaphase Effects 0.000 abstract description 6
125000003710 aryl alkyl group Chemical group 0.000 abstract description 5
230000022131 cell cycle Effects 0.000 abstract description 5
229940127089 cytotoxic agent Drugs 0.000 abstract description 4
239000002254 cytotoxic agent Substances 0.000 abstract description 4
238000007254 oxidation reaction Methods 0.000 abstract description 4
230000003647 oxidation Effects 0.000 abstract description 3
125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
230000029936 alkylation Effects 0.000 abstract 1
238000005804 alkylation reaction Methods 0.000 abstract 1
230000004663 cell proliferation Effects 0.000 abstract 1
238000010511 deprotection reaction Methods 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 125
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 81
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 29
239000007787 solid Substances 0.000 description 28
239000000725 suspension Substances 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
210000004027 cell Anatomy 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
230000018199 S phase Effects 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
GRLWQORZOWPFCM-UHFFFAOYSA-N 5-chloro-1h-pyrimidin-2-one;hydrochloride Chemical compound Cl.ClC=1C=NC(=O)NC=1 GRLWQORZOWPFCM-UHFFFAOYSA-N 0.000 description 5
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 description 5
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
239000000463 material Substances 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
230000010261 cell growth Effects 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
230000007306 turnover Effects 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
230000010337 G2 phase Effects 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 3
231100000599 cytotoxic agent Toxicity 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000012746 preparative thin layer chromatography Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
JONTXLXRSKBEPV-UHFFFAOYSA-N 4-[2-(5-chloro-2-oxopyrimidin-1-yl)acetyl]benzonitrile Chemical compound C1=C(Cl)C=NC(=O)N1CC(=O)C1=CC=C(C#N)C=C1 JONTXLXRSKBEPV-UHFFFAOYSA-N 0.000 description 2
NCLMJMKNTKRHGE-UHFFFAOYSA-N 5-chloro-1-(5-oxo-8,9-diphenyl-1,3-benzodioxepin-4-yl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1C1C(=O)C(C=CC(C=2C=CC=CC=2)=C2C=3C=CC=CC=3)=C2OCO1 NCLMJMKNTKRHGE-UHFFFAOYSA-N 0.000 description 2
AUSZEUDSCGUWTI-UHFFFAOYSA-N 5-chloro-1-[2-(2,4-dimethylphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound CC1=CC(C)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 AUSZEUDSCGUWTI-UHFFFAOYSA-N 0.000 description 2
OOJJAACPXIBOHD-UHFFFAOYSA-N 5-chloro-1-[2-(3,4-dihydroxyphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=C(O)C(O)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 OOJJAACPXIBOHD-UHFFFAOYSA-N 0.000 description 2
BKNZGUVLXOFZGR-UHFFFAOYSA-N 5-chloro-1-[2-(3-methoxyphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound COC1=CC=CC(C(=O)CN2C(N=CC(Cl)=C2)=O)=C1 BKNZGUVLXOFZGR-UHFFFAOYSA-N 0.000 description 2
FMTLRMKZYLLTFX-UHFFFAOYSA-N 5-chloro-1-[2-(4-chlorophenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(Cl)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 FMTLRMKZYLLTFX-UHFFFAOYSA-N 0.000 description 2
XTYALVROLLFIAA-UHFFFAOYSA-N 5-chloro-1-[2-(4-fluorophenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(F)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 XTYALVROLLFIAA-UHFFFAOYSA-N 0.000 description 2
DNGCBTOMQHYYGA-UHFFFAOYSA-N 5-chloro-1-[2-(4-methylphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(C)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 DNGCBTOMQHYYGA-UHFFFAOYSA-N 0.000 description 2
FBZUUVJENGQVLF-UHFFFAOYSA-N 5-chloro-1-[2-(4-methylphenyl)-2-sulfanylideneethyl]pyrimidin-2-one Chemical compound C1=CC(C)=CC=C1C(=S)CN1C(=O)N=CC(Cl)=C1 FBZUUVJENGQVLF-UHFFFAOYSA-N 0.000 description 2
NIDSEQDHBZMPGY-UHFFFAOYSA-N 5-chloro-1-[2-(4-nitrophenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 NIDSEQDHBZMPGY-UHFFFAOYSA-N 0.000 description 2
RGAXYXZDKSJHLG-UHFFFAOYSA-N 5-chloro-1-[2-oxo-2-[4-(trifluoromethyl)phenyl]ethyl]pyrimidin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 RGAXYXZDKSJHLG-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
230000010190 G1 phase Effects 0.000 description 2
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
125000005239 aroylamino group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
230000032823 cell division Effects 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000000284 extract Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
229960001330 hydroxycarbamide Drugs 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
230000000394 mitotic effect Effects 0.000 description 2
UZDBRMWBLAQQIX-UHFFFAOYSA-N n-[4-(2-bromoacetyl)phenyl]benzamide Chemical compound C1=CC(C(=O)CBr)=CC=C1NC(=O)C1=CC=CC=C1 UZDBRMWBLAQQIX-UHFFFAOYSA-N 0.000 description 2
CIUNNIBOGAOPLH-UHFFFAOYSA-N n-[4-[2-(5-chloro-2-oxopyrimidin-1-yl)acetyl]phenyl]benzamide Chemical compound C1=C(Cl)C=NC(=O)N1CC(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1 CIUNNIBOGAOPLH-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
125000004043 oxo group Chemical group O=* 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
230000001360 synchronised effect Effects 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
150000000180 1,2-diols Chemical class 0.000 description 1
DBBUILVSAPOEBC-UHFFFAOYSA-N 1-[2-(4-bromophenyl)-2-oxoethyl]-5-chloropyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1CC(=O)C1=CC=C(Br)C=C1 DBBUILVSAPOEBC-UHFFFAOYSA-N 0.000 description 1
HEJLFBLJYFSKCE-UHFFFAOYSA-N 2',3'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1O HEJLFBLJYFSKCE-UHFFFAOYSA-N 0.000 description 1
LFCLOGJMOIWPPJ-UHFFFAOYSA-N 2-(5-chloro-2-oxopyrimidin-1-yl)-1,3-diphenylpropane-1,3-dione Chemical compound C1=C(Cl)C=NC(=O)N1C(C(=O)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 LFCLOGJMOIWPPJ-UHFFFAOYSA-N 0.000 description 1
BYAJHZYXPBREEK-UHFFFAOYSA-N 2-bromo-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(Br)C(=O)C1=CC=CC=C1 BYAJHZYXPBREEK-UHFFFAOYSA-N 0.000 description 1
GKNCPTLOPRDYMH-UHFFFAOYSA-N 2-bromo-1-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(=O)CBr GKNCPTLOPRDYMH-UHFFFAOYSA-N 0.000 description 1
IOOHBIFQNQQUFI-UHFFFAOYSA-N 2-bromo-1-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(=O)CBr)=C1 IOOHBIFQNQQUFI-UHFFFAOYSA-N 0.000 description 1
FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 1
FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 1
LJYOFQHKEWTQRH-UHFFFAOYSA-N 2-bromo-1-(4-hydroxyphenyl)ethanone Chemical compound OC1=CC=C(C(=O)CBr)C=C1 LJYOFQHKEWTQRH-UHFFFAOYSA-N 0.000 description 1
XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 description 1
RLDUDUKNOCMSQQ-UHFFFAOYSA-N 2-bromo-1-(4-methylphenyl)ethanethione Chemical compound CC1=CC=C(C(=S)CBr)C=C1 RLDUDUKNOCMSQQ-UHFFFAOYSA-N 0.000 description 1
KRVGXFREOJHJAX-UHFFFAOYSA-N 2-bromo-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)CBr)C=C1 KRVGXFREOJHJAX-UHFFFAOYSA-N 0.000 description 1
MBUPVGIGAMCMBT-UHFFFAOYSA-N 2-bromo-1-(4-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CBr)C=C1 MBUPVGIGAMCMBT-UHFFFAOYSA-N 0.000 description 1
WPDWOCRJBPXJFM-UHFFFAOYSA-N 2-bromo-1-phenylpropan-1-one Chemical compound CC(Br)C(=O)C1=CC=CC=C1 WPDWOCRJBPXJFM-UHFFFAOYSA-N 0.000 description 1
YOMBUJAFGMOIGS-UHFFFAOYSA-N 2-fluoro-1-phenylethanone Chemical compound FCC(=O)C1=CC=CC=C1 YOMBUJAFGMOIGS-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 description 1
VXPUXQMUBAYRIM-UHFFFAOYSA-N 5-bromo-1-phenacylpyrimidin-2-one Chemical compound C1=C(Br)C=NC(=O)N1CC(=O)C1=CC=CC=C1 VXPUXQMUBAYRIM-UHFFFAOYSA-N 0.000 description 1
YCVVNDGBAKEXQB-UHFFFAOYSA-N 5-bromo-1h-pyrimidin-2-one;hydrobromide Chemical compound Br.OC1=NC=C(Br)C=N1 YCVVNDGBAKEXQB-UHFFFAOYSA-N 0.000 description 1
DMMWXAZVWFDMFI-UHFFFAOYSA-N 5-chloro-1-(1-oxo-1-phenylpropan-2-yl)pyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1C(C)C(=O)C1=CC=CC=C1 DMMWXAZVWFDMFI-UHFFFAOYSA-N 0.000 description 1
BNGARCANORURIB-UHFFFAOYSA-N 5-chloro-1-[2-(2-hydroxyphenyl)ethyl]pyrimidin-2-one Chemical compound OC1=CC=CC=C1CCN1C(=O)N=CC(Cl)=C1 BNGARCANORURIB-UHFFFAOYSA-N 0.000 description 1
DOBDKCODNDMJPO-UHFFFAOYSA-N 5-chloro-1-[2-(2-methoxyphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound COC1=CC=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 DOBDKCODNDMJPO-UHFFFAOYSA-N 0.000 description 1
BVMFSTRWZBVMNO-UHFFFAOYSA-N 5-chloro-1-[2-(4-hydroxyphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(O)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 BVMFSTRWZBVMNO-UHFFFAOYSA-N 0.000 description 1
SHFHYOZEDDRLJL-UHFFFAOYSA-N 5-chloro-1-[2-(4-methoxyphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 SHFHYOZEDDRLJL-UHFFFAOYSA-N 0.000 description 1
NDJUNSAPPPFFAL-UHFFFAOYSA-N 5-chloro-1-[2-(4-methylsulfinylphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(S(=O)C)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 NDJUNSAPPPFFAL-UHFFFAOYSA-N 0.000 description 1
YETCABQWWWYBOM-UHFFFAOYSA-N 5-chloro-1-[2-(4-methylsulfonylphenyl)-2-oxoethyl]pyrimidin-2-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)CN1C(=O)N=CC(Cl)=C1 YETCABQWWWYBOM-UHFFFAOYSA-N 0.000 description 1
XLISFNGIUCGGKP-UHFFFAOYSA-N 5-chloro-1-phenacylpyrimidin-2-one Chemical compound C1=C(Cl)C=NC(=O)N1CC(=O)C1=CC=CC=C1 XLISFNGIUCGGKP-UHFFFAOYSA-N 0.000 description 1
FEVBXAHTSPONGL-UHFFFAOYSA-N 5-fluoro-1-phenacylpyrimidin-2-one Chemical compound C1=C(F)C=NC(=O)N1CC(=O)C1=CC=CC=C1 FEVBXAHTSPONGL-UHFFFAOYSA-N 0.000 description 1
HPABFFGQPLJKBP-UHFFFAOYSA-N 5-fluoro-1H-pyrimidin-2-one Chemical compound OC1=NC=C(F)C=N1 HPABFFGQPLJKBP-UHFFFAOYSA-N 0.000 description 1
CPVSADXULGIXPN-UHFFFAOYSA-N 5-iodo-1-phenacylpyrimidin-2-one Chemical compound C1=C(I)C=NC(=O)N1CC(=O)C1=CC=CC=C1 CPVSADXULGIXPN-UHFFFAOYSA-N 0.000 description 1
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208000023275 Autoimmune disease Diseases 0.000 description 1
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239000004215 Carbon black (E152) Substances 0.000 description 1
FVFQGBOUYWLBIH-UHFFFAOYSA-N ClC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1.C(CCCCCCCCC)Cl Chemical compound ClC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1.C(CCCCCCCCC)Cl FVFQGBOUYWLBIH-UHFFFAOYSA-N 0.000 description 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
230000006820 DNA synthesis Effects 0.000 description 1
206010012442 Dermatitis contact Diseases 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
230000027311 M phase Effects 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 1
125000004036 acetal group Chemical group 0.000 description 1
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125000002252 acyl group Chemical group 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
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230000031016 anaphase Effects 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical compound N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 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
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000006243 carbonyl protecting group Chemical group 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
210000000349 chromosome Anatomy 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
OPTDDWCXQQYKGU-UHFFFAOYSA-N diphenyldichloromethane Chemical compound C=1C=CC=CC=1C(Cl)(Cl)C1=CC=CC=C1 OPTDDWCXQQYKGU-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
XMIVTAOFQJBIGO-UHFFFAOYSA-N ethyl 4-(2-bromoacetyl)benzoate Chemical compound CCOC(=O)C1=CC=C(C(=O)CBr)C=C1 XMIVTAOFQJBIGO-UHFFFAOYSA-N 0.000 description 1
GLOAPLPTWAXAIG-UHFFFAOYSA-N ethyl 4-acetylbenzoate Chemical compound CCOC(=O)C1=CC=C(C(C)=O)C=C1 GLOAPLPTWAXAIG-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000006260 foam Substances 0.000 description 1
230000037406 food intake Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000012010 growth Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
YRPHNSODVHXAOP-UHFFFAOYSA-N methyl 5-(2-bromoacetyl)-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(C(=O)CBr)=CC=C1O YRPHNSODVHXAOP-UHFFFAOYSA-N 0.000 description 1
YJJWMGKEUYVMTB-UHFFFAOYSA-N methyl 5-[2-(5-chloro-2-oxopyrimidin-1-yl)acetyl]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC(C(=O)CN2C(N=CC(Cl)=C2)=O)=C1 YJJWMGKEUYVMTB-UHFFFAOYSA-N 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
230000011278 mitosis Effects 0.000 description 1
MIJZKZQWQXKSPA-UHFFFAOYSA-N n-phenacylbenzamide Chemical compound C=1C=CC=CC=1C(=O)CNC(=O)C1=CC=CC=C1 MIJZKZQWQXKSPA-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000031877 prophase Effects 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000016853 telophase Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000014616 translation Effects 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Oncology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

NO812431A 1980-07-15 1981-07-15 Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-2-on-derivater. NO812431L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB8023063		1980-07-15

Publications (1)

Publication Number	Publication Date
NO812431L true NO812431L (no)	1982-01-18

Family

ID=10514771

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO812431A NO812431L (no)	1980-07-15	1981-07-15	Fremgangsmaate for fremstilling av terapeutisk aktive pyrimidin-2-on-derivater.

Country Status (12)

Country	Link
US (1)	US4636509A (de)
EP (1)	EP0044704B1 (de)
JP (1)	JPS5740471A (de)
AT (1)	ATE19627T1 (de)
AU (1)	AU7300381A (de)
CA (1)	CA1160226A (de)
DE (1)	DE3174554D1 (de)
DK (1)	DK315281A (de)
ES (2)	ES8301473A1 (de)
NO (1)	NO812431L (de)
NZ (1)	NZ197714A (de)
ZA (1)	ZA814845B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0087326B1 (de) *	1982-02-24	1987-05-13	Nycomed As	Substituierte Pyrimidin-2-one und deren Salze
GB2135992B (en) *	1983-01-11	1986-09-24	Nyegaard & Co As	Substituted pyrimidines and processes for their preparation
GB8420610D0 (en) *	1984-08-14	1984-09-19	Glaxo Group Ltd	Chemical compounds
US4820711A (en) *	1987-05-15	1989-04-11	Pearlman Dale L	Method for treating actinic keratosis with cytotoxic agents
US4853388A (en) *	1987-05-15	1989-08-01	Pearlman Dale L	Method for treating psoriasis with cytotoxic agents
US4849426A (en) *	1987-05-15	1989-07-18	Pearlman Dale L	Method for treating actinic keratosis with cytotoxic agents
US4855466A (en) *	1987-12-28	1989-08-08	E. R. Squibb & Sons, Inc.	Purinyl cyclobutanes
KR100477070B1 (ko) *	1994-03-25	2006-04-21	이소테크니카 인코포레이티드	중수소화작용에의한의약품의효능강화법
US6334997B1 (en) *	1994-03-25	2002-01-01	Isotechnika, Inc.	Method of using deuterated calcium channel blockers
MXPA06014131A (es) *	2004-06-04	2007-03-07	Astellas Pharma Inc	Derivado de propano-1,3-diona o su sal.
SI1864976T1 (sl) *	2005-03-31	2012-12-31	Astellas Pharma Inc.	Propan-1,3-dionski derivat ali njegova sol

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1561290A (en) *	1975-10-16	1980-02-20	Nyegaard & Co As	Pyrimid - 2 - ones
ES498337A0 (es) *	1980-01-07	1982-06-01	Nyegaard & Co As	Un procedimiento para la preparacion de 5-halo-pirimidin-2- onas
GB2080301B (en) *	1980-07-15	1984-04-18	Glaxo Group Ltd	Substituted pyrimidin-2-ones the salts thereof processes for their preparation and pharmaceutical compositions containing them
GB2080300B (en) *	1980-07-15	1984-04-26	Glaxo Group Ltd	Substituted pyrimidin-2-ones the salts thereof processes for their preparation and pharmaceutical compositions containing them

1981
- 1981-07-14 CA CA000381712A patent/CA1160226A/en not_active Expired
- 1981-07-14 NZ NZ197714A patent/NZ197714A/en unknown
- 1981-07-15 ZA ZA814845A patent/ZA814845B/xx unknown
- 1981-07-15 JP JP56110634A patent/JPS5740471A/ja active Pending
- 1981-07-15 DK DK315281A patent/DK315281A/da not_active Application Discontinuation
- 1981-07-15 AT AT81303254T patent/ATE19627T1/de not_active IP Right Cessation
- 1981-07-15 EP EP81303254A patent/EP0044704B1/de not_active Expired
- 1981-07-15 ES ES503984A patent/ES8301473A1/es not_active Expired
- 1981-07-15 DE DE8181303254T patent/DE3174554D1/de not_active Expired
- 1981-07-15 AU AU73003/81A patent/AU7300381A/en not_active Abandoned
- 1981-07-15 NO NO812431A patent/NO812431L/no unknown
1982
- 1982-06-16 ES ES513177A patent/ES8307758A1/es not_active Expired
1983
- 1983-05-27 US US06/498,723 patent/US4636509A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0044704B1 (de)	1986-05-07
ES503984A0 (es)	1982-12-01
EP0044704A1 (de)	1982-01-27
ES8301473A1 (es)	1982-12-01
JPS5740471A (en)	1982-03-06
CA1160226A (en)	1984-01-10
DE3174554D1 (en)	1986-06-12
AU7300381A (en)	1982-01-21
ZA814845B (en)	1983-02-23
ES513177A0 (es)	1983-07-01
US4636509A (en)	1987-01-13
NZ197714A (en)	1984-11-09
DK315281A (da)	1982-01-16
ES8307758A1 (es)	1983-07-01
ATE19627T1 (de)	1986-05-15

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