NO844311L - Fremgangsmaate for fremstilling av purinderivater - Google Patents
Fremgangsmaate for fremstilling av purinderivaterInfo
- Publication number
- NO844311L NO844311L NO844311A NO844311A NO844311L NO 844311 L NO844311 L NO 844311L NO 844311 A NO844311 A NO 844311A NO 844311 A NO844311 A NO 844311A NO 844311 L NO844311 L NO 844311L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- purin
- compound
- hydrogen
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title abstract 2
- 150000003212 purines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 59
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- QUXCASZWMFASPB-UHFFFAOYSA-N 2-amino-8-bromo-9-(1,3-dihydroxypropan-2-yloxymethyl)-3h-purin-6-one Chemical compound NC1=NC(O)=C2N=C(Br)N(COC(CO)CO)C2=N1 QUXCASZWMFASPB-UHFFFAOYSA-N 0.000 claims description 4
- CKJZEDCIKBGAHQ-UHFFFAOYSA-N 2-amino-9-[(1-hydroxy-3-phenoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC1=CC=CC=C1 CKJZEDCIKBGAHQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 4
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 4
- SYAUXCCCMBAREC-UHFFFAOYSA-N 2,8-diamino-9-(1,3-dihydroxypropan-2-yloxymethyl)-3h-purin-6-one Chemical compound OCC(CO)OCN1C(N)=NC2=C1NC(N)=NC2=O SYAUXCCCMBAREC-UHFFFAOYSA-N 0.000 claims description 3
- IHTYDYPDLDLGCD-UHFFFAOYSA-N 2,8-diamino-9-(2-hydroxyethoxymethyl)-3h-purin-6-one Chemical compound OCCOCN1C(N)=NC2=C1NC(N)=NC2=O IHTYDYPDLDLGCD-UHFFFAOYSA-N 0.000 claims description 3
- KWAMVYQVLMOSNY-UHFFFAOYSA-N 2,8-diamino-9-[(1-hydroxy-3-phenoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound NC1=NC(C(N=C(N)N2)=O)=C2N1COC(CO)COC1=CC=CC=C1 KWAMVYQVLMOSNY-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- NXAKVIFHJPMTMB-UHFFFAOYSA-N 2-amino-9-[(1-heptoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCCC)C=N2 NXAKVIFHJPMTMB-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- -1 cyclohexylethyl Chemical group 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 210000001744 T-lymphocyte Anatomy 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000001472 cytotoxic effect Effects 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- YKBGVTZYEHREMT-KVQBGUIXSA-N 2'-deoxyguanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 YKBGVTZYEHREMT-KVQBGUIXSA-N 0.000 description 3
- NCRYEGSJJUZVNT-UHFFFAOYSA-N 2-amino-9-[(1-hydroxy-3-octoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCCCC)C=N2 NCRYEGSJJUZVNT-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- QNXFUWFRTWSSOK-UHFFFAOYSA-N n-acetyl-n-(6-oxo-3,7-dihydropurin-2-yl)acetamide Chemical compound O=C1NC(N(C(C)=O)C(=O)C)=NC2=C1NC=N2 QNXFUWFRTWSSOK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- PGVLSKLBGSFLDK-UHFFFAOYSA-N 1-heptoxy-3-phenylmethoxypropan-2-ol Chemical compound CCCCCCCOCC(O)COCC1=CC=CC=C1 PGVLSKLBGSFLDK-UHFFFAOYSA-N 0.000 description 2
- YKBGVTZYEHREMT-UHFFFAOYSA-N 2'-deoxyguanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1CC(O)C(CO)O1 YKBGVTZYEHREMT-UHFFFAOYSA-N 0.000 description 2
- DBANOIFVJPDGCN-UHFFFAOYSA-N 2,8-diamino-9-[(1-hexoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCC)C(N)=N2 DBANOIFVJPDGCN-UHFFFAOYSA-N 0.000 description 2
- QNYBOILAKBSWFG-UHFFFAOYSA-N 2-(phenylmethoxymethyl)oxirane Chemical compound C1OC1COCC1=CC=CC=C1 QNYBOILAKBSWFG-UHFFFAOYSA-N 0.000 description 2
- GBMIHDMGBMQYBU-UHFFFAOYSA-N 2-amino-8-bromo-9-(2-hydroxyethoxymethyl)-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C(Br)=N2 GBMIHDMGBMQYBU-UHFFFAOYSA-N 0.000 description 2
- BQFOFKKTQGZYBK-UHFFFAOYSA-N 2-amino-8-bromo-9-[(1-hexoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCC)C(Br)=N2 BQFOFKKTQGZYBK-UHFFFAOYSA-N 0.000 description 2
- GLBWXMZANYSQDW-UHFFFAOYSA-N 2-amino-9-(1-hydroxyheptan-2-yloxymethyl)-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)CCCCC)C=N2 GLBWXMZANYSQDW-UHFFFAOYSA-N 0.000 description 2
- FSLAUGOJXDFBDG-UHFFFAOYSA-N 2-amino-9-[(1-butoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)N=C2N(COC(CO)COCCCC)C=NC2=C1O FSLAUGOJXDFBDG-UHFFFAOYSA-N 0.000 description 2
- SRSRXZIHJUQBEV-UHFFFAOYSA-N 2-amino-9-[(1-ethoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCC)C=N2 SRSRXZIHJUQBEV-UHFFFAOYSA-N 0.000 description 2
- AIZPYPXJKSENJG-UHFFFAOYSA-N 2-amino-9-[(1-hexoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(COC(CO)COCCCCCC)C=N2 AIZPYPXJKSENJG-UHFFFAOYSA-N 0.000 description 2
- JIXVAJOIBHFGNE-UHFFFAOYSA-N 2-amino-9-[[1-(cyclohexylmethoxy)-3-hydroxypropan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COCC1CCCCC1 JIXVAJOIBHFGNE-UHFFFAOYSA-N 0.000 description 2
- JBMBVWROWJGFMG-UHFFFAOYSA-N 2-chloro-7h-purine Chemical class ClC1=NC=C2NC=NC2=N1 JBMBVWROWJGFMG-UHFFFAOYSA-N 0.000 description 2
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 101710101148 Probable 6-oxopurine nucleoside phosphorylase Proteins 0.000 description 2
- 102000030764 Purine-nucleoside phosphorylase Human genes 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- VGONTNSXDCQUGY-UHFFFAOYSA-N desoxyinosine Natural products C1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 VGONTNSXDCQUGY-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- RHCJOJOTIRDEMY-UHFFFAOYSA-N n-[9-[(1-butoxy-3-phenylmethoxypropan-2-yl)oxymethyl]-6-oxo-3h-purin-2-yl]acetamide Chemical compound C1=NC2=C(O)N=C(NC(C)=O)N=C2N1COC(COCCCC)COCC1=CC=CC=C1 RHCJOJOTIRDEMY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- BBSQDVXZFJYDOS-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-phenylmethoxypropan-2-ol Chemical compound C=1C=C(Cl)C=CC=1OCC(O)COCC1=CC=CC=C1 BBSQDVXZFJYDOS-UHFFFAOYSA-N 0.000 description 1
- SZOVYJKHSYPOJP-UHFFFAOYSA-N 1-(4-methoxyphenoxy)-3-phenylmethoxypropan-2-ol Chemical compound C1=CC(OC)=CC=C1OCC(O)COCC1=CC=CC=C1 SZOVYJKHSYPOJP-UHFFFAOYSA-N 0.000 description 1
- ILLMAKTZVKCTOM-UHFFFAOYSA-N 1-(4-methylphenoxy)-3-phenylmethoxypropan-2-ol Chemical compound C1=CC(C)=CC=C1OCC(O)COCC1=CC=CC=C1 ILLMAKTZVKCTOM-UHFFFAOYSA-N 0.000 description 1
- DUNZDKFSZGOYBX-UHFFFAOYSA-N 1-(cyclohexylmethoxy)-3-phenylmethoxypropan-2-ol Chemical compound C=1C=CC=CC=1COCC(O)COCC1CCCCC1 DUNZDKFSZGOYBX-UHFFFAOYSA-N 0.000 description 1
- ZMOVOCVQXFKQEA-UHFFFAOYSA-N 1-butoxy-3-phenylmethoxypropan-2-ol Chemical compound CCCCOCC(O)COCC1=CC=CC=C1 ZMOVOCVQXFKQEA-UHFFFAOYSA-N 0.000 description 1
- XDUMGAUEVOHWCL-UHFFFAOYSA-N 1-ethoxy-3-phenylmethoxypropan-2-ol Chemical compound CCOCC(O)COCC1=CC=CC=C1 XDUMGAUEVOHWCL-UHFFFAOYSA-N 0.000 description 1
- SKWQDODIGMJFDQ-UHFFFAOYSA-N 1-hexoxy-3-phenylmethoxypropan-2-ol Chemical compound CCCCCCOCC(O)COCC1=CC=CC=C1 SKWQDODIGMJFDQ-UHFFFAOYSA-N 0.000 description 1
- FGNFXBDLFNNANE-UHFFFAOYSA-N 1-octoxy-3-phenylmethoxypropan-2-ol Chemical compound CCCCCCCCOCC(O)COCC1=CC=CC=C1 FGNFXBDLFNNANE-UHFFFAOYSA-N 0.000 description 1
- MWRDMMHGNBRMMK-UHFFFAOYSA-N 1-pentoxy-3-phenylmethoxypropan-2-ol Chemical compound CCCCCOCC(O)COCC1=CC=CC=C1 MWRDMMHGNBRMMK-UHFFFAOYSA-N 0.000 description 1
- LMGLEIAYFYAJGL-UHFFFAOYSA-N 1-phenoxy-3-phenylmethoxypropan-2-ol Chemical compound C=1C=CC=CC=1OCC(O)COCC1=CC=CC=C1 LMGLEIAYFYAJGL-UHFFFAOYSA-N 0.000 description 1
- MHVVPWPYSVXDMW-UHFFFAOYSA-N 1-phenylmethoxydecan-2-ol Chemical compound CCCCCCCCC(O)COCC1=CC=CC=C1 MHVVPWPYSVXDMW-UHFFFAOYSA-N 0.000 description 1
- HFMJYFWNEXXMFR-UHFFFAOYSA-N 1-phenylmethoxyheptan-2-ol Chemical compound CCCCCC(O)COCC1=CC=CC=C1 HFMJYFWNEXXMFR-UHFFFAOYSA-N 0.000 description 1
- OCKMKLFLOSPCLO-UHFFFAOYSA-N 2,8-diamino-9-(1-hydroxydecan-2-yloxymethyl)-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)CCCCCCCC)C(N)=N2 OCKMKLFLOSPCLO-UHFFFAOYSA-N 0.000 description 1
- BOZIWXUAOYBIEF-UHFFFAOYSA-N 2,8-diamino-9-[(1-butoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)N=C2N(COC(CO)COCCCC)C(N)=NC2=C1O BOZIWXUAOYBIEF-UHFFFAOYSA-N 0.000 description 1
- GTJLUDFMFMQHOL-UHFFFAOYSA-N 2,8-diamino-9-[(1-heptoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCCC)C(N)=N2 GTJLUDFMFMQHOL-UHFFFAOYSA-N 0.000 description 1
- NOQRDXGPJQXJSB-UHFFFAOYSA-N 2,8-diamino-9-[(1-hydroxy-3-octoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCCCC)C(N)=N2 NOQRDXGPJQXJSB-UHFFFAOYSA-N 0.000 description 1
- IRYAWQTVDMPEBO-UHFFFAOYSA-N 2,8-diamino-9-[(1-hydroxy-3-pentoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCC)C(N)=N2 IRYAWQTVDMPEBO-UHFFFAOYSA-N 0.000 description 1
- SLARWLAMLAMAOT-UHFFFAOYSA-N 2,8-diamino-9-[1,3-bis(phenylmethoxy)propan-2-yloxymethyl]-3h-purin-6-one Chemical compound NC1=NC(C(NC(N)=N2)=O)=C2N1COC(COCC=1C=CC=CC=1)COCC1=CC=CC=C1 SLARWLAMLAMAOT-UHFFFAOYSA-N 0.000 description 1
- NZZCYHQSOVRSQM-UHFFFAOYSA-N 2,8-diamino-9-[[1-(cyclohexylmethoxy)-3-hydroxypropan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound NC1=NC(C(NC(N)=N2)=O)=C2N1COC(CO)COCC1CCCCC1 NZZCYHQSOVRSQM-UHFFFAOYSA-N 0.000 description 1
- XHXSRHOCJQXWIS-UHFFFAOYSA-N 2,8-diamino-9-[[1-hydroxy-3-(4-methoxyphenoxy)propan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound C1=CC(OC)=CC=C1OCC(CO)OCN1C(NC(N)=NC2=O)=C2N=C1N XHXSRHOCJQXWIS-UHFFFAOYSA-N 0.000 description 1
- AXRHOQUHBMGAON-UHFFFAOYSA-N 2-(2-amino-6-oxo-1h-purin-2-yl)acetamide Chemical class NC(=O)CC1(N)NC(=O)C2=NC=NC2=N1 AXRHOQUHBMGAON-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
- CGZGNJRARKJEMQ-UHFFFAOYSA-N 2-amino-8-bromo-9-(1-hydroxydecan-2-yloxymethyl)-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)CCCCCCCC)C(Br)=N2 CGZGNJRARKJEMQ-UHFFFAOYSA-N 0.000 description 1
- XKXFGZRXGAOXSS-UHFFFAOYSA-N 2-amino-8-bromo-9-[(1-butoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)N=C2N(COC(CO)COCCCC)C(Br)=NC2=C1O XKXFGZRXGAOXSS-UHFFFAOYSA-N 0.000 description 1
- SRBZUZTXBAMDNS-UHFFFAOYSA-N 2-amino-8-bromo-9-[(1-ethoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCC)C(Br)=N2 SRBZUZTXBAMDNS-UHFFFAOYSA-N 0.000 description 1
- KALUONDLANBVPG-UHFFFAOYSA-N 2-amino-8-bromo-9-[(1-heptoxy-3-hydroxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCCC)C(Br)=N2 KALUONDLANBVPG-UHFFFAOYSA-N 0.000 description 1
- WHWJPLRPVQBZJM-UHFFFAOYSA-N 2-amino-8-bromo-9-[(1-hydroxy-3-octoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCCCCC)C(Br)=N2 WHWJPLRPVQBZJM-UHFFFAOYSA-N 0.000 description 1
- JANGSIBIQQXVDD-UHFFFAOYSA-N 2-amino-8-bromo-9-[(1-hydroxy-3-pentoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCC)C(Br)=N2 JANGSIBIQQXVDD-UHFFFAOYSA-N 0.000 description 1
- YHAKHFAXROXXPZ-UHFFFAOYSA-N 2-amino-8-bromo-9-[(1-hydroxy-3-phenoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound BrC1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC1=CC=CC=C1 YHAKHFAXROXXPZ-UHFFFAOYSA-N 0.000 description 1
- GLHOVIOCJZDUCA-UHFFFAOYSA-N 2-amino-8-bromo-9-[[1-(4-chlorophenoxy)-3-hydroxypropan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=C(Br)N1COC(CO)COC1=CC=C(Cl)C=C1 GLHOVIOCJZDUCA-UHFFFAOYSA-N 0.000 description 1
- AJPCIQXOPCFGCT-UHFFFAOYSA-N 2-amino-8-bromo-9-[[1-hydroxy-3-(4-methoxyphenoxy)propan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound C1=CC(OC)=CC=C1OCC(CO)OCN1C(N=C(N)NC2=O)=C2N=C1Br AJPCIQXOPCFGCT-UHFFFAOYSA-N 0.000 description 1
- GKRSZSFWDXFHHK-UHFFFAOYSA-N 2-amino-8-bromo-9-[[1-hydroxy-3-(4-methylphenoxy)propan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound C1=CC(C)=CC=C1OCC(CO)OCN1C(N=C(N)NC2=O)=C2N=C1Br GKRSZSFWDXFHHK-UHFFFAOYSA-N 0.000 description 1
- ACGLNBCGCXQURC-UHFFFAOYSA-N 2-amino-9-(1-hydroxydecan-2-yloxymethyl)-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)CCCCCCCC)C=N2 ACGLNBCGCXQURC-UHFFFAOYSA-N 0.000 description 1
- BFESGWPOQYGMAV-UHFFFAOYSA-N 2-amino-9-[(1-hydroxy-3-pentoxypropan-2-yl)oxymethyl]-3h-purin-6-one Chemical compound N1=C(N)NC(=O)C2=C1N(COC(CO)COCCCCC)C=N2 BFESGWPOQYGMAV-UHFFFAOYSA-N 0.000 description 1
- RMRKSAOEJZMVHB-UHFFFAOYSA-N 2-amino-9-[1,3-bis(phenylmethoxy)propan-2-yloxymethyl]-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(COCC=1C=CC=CC=1)COCC1=CC=CC=C1 RMRKSAOEJZMVHB-UHFFFAOYSA-N 0.000 description 1
- GOWFIFQAUMYZRU-UHFFFAOYSA-N 2-amino-9-[[1-(4-chlorophenoxy)-3-hydroxypropan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1COC(CO)COC1=CC=C(Cl)C=C1 GOWFIFQAUMYZRU-UHFFFAOYSA-N 0.000 description 1
- MHRFOIFHXOJVSM-UHFFFAOYSA-N 2-amino-9-[[1-hydroxy-3-(4-methylphenoxy)propan-2-yl]oxymethyl]-3h-purin-6-one Chemical compound C1=CC(C)=CC=C1OCC(CO)OCN1C(N=C(N)NC2=O)=C2N=C1 MHRFOIFHXOJVSM-UHFFFAOYSA-N 0.000 description 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- DGGUDQTUJAPWME-UHFFFAOYSA-N 4-chlorobutane-1,2,3-triol Chemical compound OCC(O)C(O)CCl DGGUDQTUJAPWME-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 208000030729 Juvenile myasthenia gravis Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 208000036142 Viral infection Diseases 0.000 description 1
- NVTYGJCEFUGXJT-UHFFFAOYSA-N [2-(chloromethoxy)-3-heptoxypropoxy]methylbenzene Chemical compound CCCCCCCOCC(OCCl)COCC1=CC=CC=C1 NVTYGJCEFUGXJT-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- MYTMXVHNEWBFAL-UHFFFAOYSA-L dipotassium;carbonate;hydrate Chemical compound O.[K+].[K+].[O-]C([O-])=O MYTMXVHNEWBFAL-UHFFFAOYSA-L 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000007365 immunoregulation Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- BPEAWRMOOWAWLQ-UHFFFAOYSA-N n-[6-oxo-9-[(1-phenoxy-3-phenylmethoxypropan-2-yl)oxymethyl]-3h-purin-2-yl]acetamide Chemical compound C1=NC=2C(=O)NC(NC(=O)C)=NC=2N1COC(COC=1C=CC=CC=1)COCC1=CC=CC=C1 BPEAWRMOOWAWLQ-UHFFFAOYSA-N 0.000 description 1
- UUQILXHEFPLUDL-UHFFFAOYSA-N n-[9-[(1-ethoxy-3-phenylmethoxypropan-2-yl)oxymethyl]-6-oxo-3h-purin-2-yl]acetamide Chemical compound C1=NC(C(NC(NC(C)=O)=N2)=O)=C2N1COC(COCC)COCC1=CC=CC=C1 UUQILXHEFPLUDL-UHFFFAOYSA-N 0.000 description 1
- JMJSEHGFNLKHLX-UHFFFAOYSA-N n-[9-[(1-octoxy-3-phenylmethoxypropan-2-yl)oxymethyl]-6-oxo-3h-purin-2-yl]acetamide Chemical compound C1=NC(C(N=C(NC(C)=O)N2)=O)=C2N1COC(COCCCCCCCC)COCC1=CC=CC=C1 JMJSEHGFNLKHLX-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid 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
- 230000000699 topical effect Effects 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
- C07C43/1745—Unsaturated ethers containing halogen containing six-membered aromatic rings having more than one ether bound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1782—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1788—Unsaturated ethers containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54729783A | 1983-10-31 | 1983-10-31 | |
| US65721184A | 1984-10-05 | 1984-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO844311L true NO844311L (no) | 1985-05-02 |
Family
ID=27068502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO844311A NO844311L (no) | 1983-10-31 | 1984-10-30 | Fremgangsmaate for fremstilling av purinderivater |
Country Status (16)
| Country | Link |
|---|---|
| EP (4) | EP0249248A3 (ko) |
| KR (1) | KR850002982A (ko) |
| AT (2) | ATE71078T1 (ko) |
| AU (2) | AU586808B2 (ko) |
| CA (2) | CA1281323C (ko) |
| DE (2) | DE3476392D1 (ko) |
| DK (2) | DK516684A (ko) |
| ES (3) | ES8602792A1 (ko) |
| FI (1) | FI844232L (ko) |
| GR (1) | GR80793B (ko) |
| HU (1) | HUT35680A (ko) |
| IE (2) | IE842642L (ko) |
| IL (1) | IL73320A0 (ko) |
| NO (1) | NO844311L (ko) |
| NZ (1) | NZ210031A (ko) |
| PT (1) | PT79428B (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4921859A (en) * | 1983-10-31 | 1990-05-01 | Warner-Lambert Company | Purine derivatives |
| HUT39145A (en) * | 1984-12-12 | 1986-08-28 | Syntex Inc | Process for preparing alkoxy-methyl-ether and alkoxy-methyl ester derivatives |
| EP0193454A1 (en) * | 1985-02-25 | 1986-09-03 | Merck & Co. Inc. | 8-Substituted-9-hydroxyalkyl and hydroxyalkoxymethyl-guanines and pharmaceutical compositions containing them |
| IL78643A0 (en) * | 1985-05-02 | 1986-08-31 | Wellcome Found | Purine derivatives,their preparation and pharmaceutical compositions containing them |
| DE3627024A1 (de) * | 1985-09-24 | 1987-04-02 | Hoechst Ag | In 6- und 9-stellung substituierte 2-aminopurine, ihre verwendung, diese purine enthaltende arzneimittel und verfahren zur herstellung der purine |
| JPH0635242B2 (ja) * | 1987-09-04 | 1994-05-11 | 三菱自動車工業株式会社 | 車両用サスペンション装置 |
| JPH0725245B2 (ja) * | 1987-09-04 | 1995-03-22 | 三菱自動車工業株式会社 | 車両用サスペンション装置 |
| JPH0635245B2 (ja) * | 1987-10-15 | 1994-05-11 | 三菱自動車工業株式会社 | 車両用サスペンション装置 |
| GB8816760D0 (en) * | 1988-07-14 | 1988-08-17 | Wellcome Found | Therapeutic compounds |
| DE3906357A1 (de) * | 1989-03-01 | 1990-09-06 | Boehringer Mannheim Gmbh | Neue acyclische nucleosid-analoga, verfahren zu ihrer herstellung und verwendung dieser verbindungen als antivirale arzneimittel |
| PE32296A1 (es) * | 1994-07-28 | 1996-08-07 | Hoffmann La Roche | Ester de l-monovalina derivado de 2-(2-amino-1,6-dihidro-6-oxo-purin-9-il) metoxi-1,3-propandiol y sus sales farmaceuticamente aceptables |
| US5856481A (en) * | 1994-07-28 | 1999-01-05 | Syntex (U.S.A.) Inc. | 2-(2-amino-1,6-dihydro-6-oxo-purin-9-yl)methoxy-1,3-propanediol derivative |
| DE69638137D1 (de) | 1995-09-07 | 2010-04-15 | Univ Georgia | Therapeutische azidverbindungen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
| YU41079B (en) * | 1976-08-27 | 1986-12-31 | Wellcome Found | Process for the synthesis of substituted purine compounds |
| US4347360A (en) * | 1980-09-16 | 1982-08-31 | Ens Bio Logicals Inc. | Ring open nucleoside analogues |
| US4355032B2 (en) * | 1981-05-21 | 1990-10-30 | 9-(1,3-dihydroxy-2-propoxymethyl)guanine as antiviral agent | |
| US5250535A (en) * | 1982-02-01 | 1993-10-05 | Syntex Inc. | Substituted 9-(1 or 3-monoacyloxy or 1,3-diacyloxy-2-propoxymethyl) purines as antiviral agent |
| DE3234610A1 (de) * | 1982-09-16 | 1984-03-22 | Schering AG, 1000 Berlin und 4709 Bergkamen | Benzylaetherderivate des glycerins, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit wachstumsregulatorischer wirkung fuer pflanzen |
-
1984
- 1984-10-15 IE IE842642A patent/IE842642L/xx unknown
- 1984-10-18 CA CA000465748A patent/CA1281323C/en not_active Expired - Fee Related
- 1984-10-25 KR KR1019840006654A patent/KR850002982A/ko not_active IP Right Cessation
- 1984-10-25 IL IL73320A patent/IL73320A0/xx unknown
- 1984-10-26 DE DE8484307373T patent/DE3476392D1/de not_active Expired
- 1984-10-26 EP EP87108734A patent/EP0249248A3/en not_active Withdrawn
- 1984-10-26 EP EP84307373A patent/EP0145207B1/en not_active Expired
- 1984-10-26 AU AU34747/84A patent/AU586808B2/en not_active Ceased
- 1984-10-26 AT AT87108735T patent/ATE71078T1/de active
- 1984-10-26 DE DE8787108735T patent/DE3485419D1/de not_active Expired - Fee Related
- 1984-10-26 AT AT84307373T patent/ATE40369T1/de not_active IP Right Cessation
- 1984-10-26 EP EP87108735A patent/EP0249249B1/en not_active Expired - Lifetime
- 1984-10-26 EP EP87108733A patent/EP0249247A3/en not_active Withdrawn
- 1984-10-29 FI FI844232A patent/FI844232L/fi not_active Application Discontinuation
- 1984-10-29 GR GR80793A patent/GR80793B/el unknown
- 1984-10-30 HU HU844020A patent/HUT35680A/hu unknown
- 1984-10-30 ES ES537205A patent/ES8602792A1/es not_active Expired
- 1984-10-30 PT PT79428A patent/PT79428B/pt not_active IP Right Cessation
- 1984-10-30 NO NO844311A patent/NO844311L/no unknown
- 1984-10-30 DK DK516684A patent/DK516684A/da not_active Application Discontinuation
- 1984-10-30 NZ NZ210031A patent/NZ210031A/en unknown
-
1985
- 1985-07-15 ES ES545195A patent/ES8604223A1/es not_active Expired
- 1985-07-15 ES ES545194A patent/ES8606347A1/es not_active Expired
-
1987
- 1987-11-24 CA CA000552674A patent/CA1284509C/en not_active Expired - Fee Related
-
1989
- 1989-04-25 IE IE891346A patent/IE891346L/xx unknown
- 1989-05-02 AU AU33956/89A patent/AU3395689A/en not_active Withdrawn
-
1992
- 1992-08-19 DK DK921028A patent/DK102892D0/da not_active Application Discontinuation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5807862A (en) | Therapeutic compounds containing pyrimidinyl moieties | |
| US5981535A (en) | Substituted xanthines and their use in the treatment of cerebrovascular disorders and other diseases | |
| EP0074256B1 (en) | Camptothecin derivatives, processes for preparing same, formulations containing such derivatives and their use | |
| US4855466A (en) | Purinyl cyclobutanes | |
| US6573378B1 (en) | Antiviral guanine derivatives | |
| KR880002276B1 (ko) | 항비루스성 화합물의 제조방법 | |
| US5723609A (en) | Bis (hydroxymethyl) cyclobutyl purines | |
| US5470878A (en) | Cell signaling inhibitors | |
| US4495190A (en) | Derivatives of guanine for combating herpes virus infections | |
| EP0022317B1 (en) | 2-oxo-benzothiazoline, benzoxazoline or indoline derivatives, their preparation, and pharmaceutical compositions comprising such derivatives | |
| NO844311L (no) | Fremgangsmaate for fremstilling av purinderivater | |
| US5017701A (en) | Process for the preparation of purine derivatives | |
| IE913350A1 (en) | Novel compounds | |
| CZ305197A3 (cs) | Inhibitor proteinu kinasa C, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje | |
| JPS63297381A (ja) | ９−〔２−（ヒドロキシメチル）シクロアルキルメチル〕グアニン類 | |
| US5126345A (en) | Bis (hydroxymethyl) cyclobutyl triazolopyrimidines | |
| US4806642A (en) | Purine derivatives | |
| BG61729B1 (bg) | 9-заместени-2-(2-норм-алкоксифенил)пурин-6-они | |
| US5098906A (en) | Purine derivatives | |
| EP2170840A1 (en) | An improved process for preparing purine derivative | |
| EP0044704B1 (en) | Substituted pyrimidin-2-ones, the salts thereof, processes for their preparation, and pharmaceutical compositions containing them | |
| WO1994024133A1 (en) | Ring-substituted cell signaling inhibitors | |
| EP0173279B1 (en) | 2-(3,5-dialkyl-4-hydroxyphenyl)indole derivatives | |
| US4921859A (en) | Purine derivatives | |
| CA1075237A (en) | Purine derivatives |