FI82696C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla pteridiner. - Google Patents
Foerfarande foer framstaellning av farmakologiskt vaerdefulla pteridiner. Download PDFInfo
- Publication number
- FI82696C FI82696C FI854862A FI854862A FI82696C FI 82696 C FI82696 C FI 82696C FI 854862 A FI854862 A FI 854862A FI 854862 A FI854862 A FI 854862A FI 82696 C FI82696 C FI 82696C
- Authority
- FI
- Finland
- Prior art keywords
- group
- phenyl
- pteridine
- yield
- melting point
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000000144 pharmacologic effect Effects 0.000 title description 5
- -1 pyrrolidino, piperidino, morpholino, thiomorpholino, 1-oxidothiomorpholino Chemical group 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 150000003195 pteridines Chemical class 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- CYMCSLFWXQJBHU-UHFFFAOYSA-N n-benzyl-6-phenyl-2-piperazin-1-yl-4-thiomorpholin-4-ylpteridin-7-amine Chemical compound C=1C=CC=CC=1CNC(C(=NC1=2)C=3C=CC=CC=3)=NC1=NC(N1CCNCC1)=NC=2N1CCSCC1 CYMCSLFWXQJBHU-UHFFFAOYSA-N 0.000 claims description 3
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 135
- 238000002844 melting Methods 0.000 description 76
- 230000008018 melting Effects 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 150000002168 ethanoic acid esters Chemical class 0.000 description 11
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 10
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 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
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940093915 gynecological organic acid Drugs 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- WSYXJPXVIWXEKQ-UHFFFAOYSA-N 4-(2,7-dichloro-6-phenylpteridin-4-yl)thiomorpholine Chemical compound C=12N=C(C=3C=CC=CC=3)C(Cl)=NC2=NC(Cl)=NC=1N1CCSCC1 WSYXJPXVIWXEKQ-UHFFFAOYSA-N 0.000 description 3
- LDXZXENTEQVNJT-UHFFFAOYSA-N 4-(7-chloro-4-morpholin-4-yl-6-phenylpteridin-2-yl)piperazine-1-carbaldehyde Chemical compound C=12N=C(C=3C=CC=CC=3)C(Cl)=NC2=NC(N2CCN(CC2)C=O)=NC=1N1CCOCC1 LDXZXENTEQVNJT-UHFFFAOYSA-N 0.000 description 3
- GAWKTFFNBBOGFS-UHFFFAOYSA-N 4-[7-chloro-4-(1-oxo-1,4-thiazinan-4-yl)-6-phenylpteridin-2-yl]piperazine-1-carbaldehyde Chemical compound C=12N=C(C=3C=CC=CC=3)C(Cl)=NC2=NC(N2CCN(CC2)C=O)=NC=1N1CCS(=O)CC1 GAWKTFFNBBOGFS-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RIBWUHCWCPYSQW-UHFFFAOYSA-N 2-piperazin-1-ylpteridine Chemical class C1CNCCN1C1=NC=C(N=CC=N2)C2=N1 RIBWUHCWCPYSQW-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- GJBIGLFKYRNPRQ-UHFFFAOYSA-N 4-(2,7-dichloro-6-phenylpteridin-4-yl)morpholine Chemical compound C=12N=C(C=3C=CC=CC=3)C(Cl)=NC2=NC(Cl)=NC=1N1CCOCC1 GJBIGLFKYRNPRQ-UHFFFAOYSA-N 0.000 description 2
- SWQVUKRKXPTFJY-UHFFFAOYSA-N 4-(2,7-dichloropteridin-4-yl)morpholine Chemical compound N=1C(Cl)=NC2=NC(Cl)=CN=C2C=1N1CCOCC1 SWQVUKRKXPTFJY-UHFFFAOYSA-N 0.000 description 2
- CEQDHZLUCKTZDQ-UHFFFAOYSA-N 4-(2-chloro-4-morpholin-4-ylpteridin-7-yl)morpholine Chemical compound C=12N=CC(N3CCOCC3)=NC2=NC(Cl)=NC=1N1CCOCC1 CEQDHZLUCKTZDQ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- GLAMJFYGEMODFF-UHFFFAOYSA-N 4-[7-(benzylamino)-6-phenyl-4-thiomorpholin-4-ylpteridin-2-yl]piperazine-1-carbaldehyde Chemical compound C1CN(C=O)CCN1C1=NC(N2CCSCC2)=C(N=C(C(NCC=2C=CC=CC=2)=N2)C=3C=CC=CC=3)C2=N1 GLAMJFYGEMODFF-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 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 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002001 anti-metastasis Effects 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UXVXHECNJUECPO-UHFFFAOYSA-N n,n-dimethyl-6-phenyl-2-piperazin-1-yl-4-pyrrolidin-1-ylpteridin-7-amine Chemical compound C=12N=C(C=3C=CC=CC=3)C(N(C)C)=NC2=NC(N2CCNCC2)=NC=1N1CCCC1 UXVXHECNJUECPO-UHFFFAOYSA-N 0.000 description 2
- KNDYYVVEFVWOOT-UHFFFAOYSA-N n-benzyl-2-chloro-4-piperidin-1-ylpteridin-7-amine Chemical compound C=12N=CC(NCC=3C=CC=CC=3)=NC2=NC(Cl)=NC=1N1CCCCC1 KNDYYVVEFVWOOT-UHFFFAOYSA-N 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- NWBJBMHJBACYGT-UHFFFAOYSA-N 2,4,7-trichloro-6-phenylpteridine Chemical compound ClC1=NC2=NC(Cl)=NC(Cl)=C2N=C1C1=CC=CC=C1 NWBJBMHJBACYGT-UHFFFAOYSA-N 0.000 description 1
- VQPKNENUIGMHNU-UHFFFAOYSA-N 2,4,7-trichloropteridine Chemical compound ClC1=NC(Cl)=NC2=NC(Cl)=CN=C21 VQPKNENUIGMHNU-UHFFFAOYSA-N 0.000 description 1
- RGKRHWLTEUVZHM-UHFFFAOYSA-N 2,7-dichloro-6-phenyl-4-piperidin-1-ylpteridine Chemical compound C=12N=C(C=3C=CC=CC=3)C(Cl)=NC2=NC(Cl)=NC=1N1CCCCC1 RGKRHWLTEUVZHM-UHFFFAOYSA-N 0.000 description 1
- ILYDCKYNGFVQHZ-UHFFFAOYSA-N 2,7-dichloro-N,N-dimethyl-6-phenylpteridin-4-amine Chemical compound ClC1=NC2=NC(=C(N=C2C(=N1)N(C)C)C1=CC=CC=C1)Cl ILYDCKYNGFVQHZ-UHFFFAOYSA-N 0.000 description 1
- OJERFWUAMPYEMC-UHFFFAOYSA-N 2-[[7-(benzylamino)-2-chloropteridin-4-yl]-methylamino]ethanol Chemical compound C=1N=C2C(N(CCO)C)=NC(Cl)=NC2=NC=1NCC1=CC=CC=C1 OJERFWUAMPYEMC-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CKVPAYIYEWAHIB-UHFFFAOYSA-N 4-(2,7-dichloro-6-methyl-6H-pteridin-7-yl)morpholine Chemical compound ClC1=NC2=NC(C(N=C2C=N1)C)(N1CCOCC1)Cl CKVPAYIYEWAHIB-UHFFFAOYSA-N 0.000 description 1
- NSWWAJFJFVIFIY-UHFFFAOYSA-N 4-(2-chloro-6-methyl-4-morpholin-4-ylpteridin-7-yl)morpholine Chemical compound CC1=NC2=C(N3CCOCC3)N=C(Cl)N=C2N=C1N1CCOCC1 NSWWAJFJFVIFIY-UHFFFAOYSA-N 0.000 description 1
- NLYWGPYBUHRLLS-UHFFFAOYSA-N 4-(2-chloro-6-methyl-7-thiomorpholin-4-ylpteridin-4-yl)morpholine Chemical compound CC1=NC2=C(N3CCOCC3)N=C(Cl)N=C2N=C1N1CCSCC1 NLYWGPYBUHRLLS-UHFFFAOYSA-N 0.000 description 1
- XGWVNQNSJQGULB-UHFFFAOYSA-N 4-(4-morpholin-4-yl-2-piperazin-1-ylpteridin-7-yl)morpholine Chemical compound C1CNCCN1C1=NC(N2CCOCC2)=C(N=CC(=N2)N3CCOCC3)C2=N1 XGWVNQNSJQGULB-UHFFFAOYSA-N 0.000 description 1
- DUWXBAYNTVXXPX-UHFFFAOYSA-N 4-(6-methyl-2-piperazin-1-yl-7-thiomorpholin-4-ylpteridin-4-yl)morpholine Chemical compound CC1=NC2=C(N3CCOCC3)N=C(N3CCNCC3)N=C2N=C1N1CCSCC1 DUWXBAYNTVXXPX-UHFFFAOYSA-N 0.000 description 1
- JYKRPHPHUQAIPZ-UHFFFAOYSA-N 4-(7-chloro-6-phenyl-4-pyrrolidin-1-ylpteridin-2-yl)piperazine-1-carbaldehyde Chemical compound C=12N=C(C=3C=CC=CC=3)C(Cl)=NC2=NC(N2CCN(CC2)C=O)=NC=1N1CCCC1 JYKRPHPHUQAIPZ-UHFFFAOYSA-N 0.000 description 1
- DAUCBPOTMUPLBF-UHFFFAOYSA-N 4-(7-chloro-6-phenyl-4-thiomorpholin-4-ylpteridin-2-yl)piperazine-1-carbaldehyde Chemical compound C=12N=C(C=3C=CC=CC=3)C(Cl)=NC2=NC(N2CCN(CC2)C=O)=NC=1N1CCSCC1 DAUCBPOTMUPLBF-UHFFFAOYSA-N 0.000 description 1
- QHHLKOCFSWZNRA-UHFFFAOYSA-N 4-(7-morpholin-4-yl-6-phenyl-2-piperazin-1-ylpteridin-4-yl)-1,4-thiazinane 1-oxide Chemical compound O1CCN(CC1)C1=C(N=C2C(=NC(=NC2=N1)N1CCNCC1)N1CCS(CC1)=O)C1=CC=CC=C1 QHHLKOCFSWZNRA-UHFFFAOYSA-N 0.000 description 1
- BAUOJBQIZRQWRY-UHFFFAOYSA-N 4-[4-[benzyl(methyl)amino]-7-(dimethylamino)-6-phenylpteridin-2-yl]piperazine-1-carbaldehyde Chemical compound C=12N=C(C=3C=CC=CC=3)C(N(C)C)=NC2=NC(N2CCN(CC2)C=O)=NC=1N(C)CC1=CC=CC=C1 BAUOJBQIZRQWRY-UHFFFAOYSA-N 0.000 description 1
- RQSVNURXHGGPTO-UHFFFAOYSA-N 4-[4-[benzyl(methyl)amino]-7-chloro-6-phenylpteridin-2-yl]piperazine-1-carbaldehyde Chemical compound N=1C(N2CCN(CC2)C=O)=NC2=NC(Cl)=C(C=3C=CC=CC=3)N=C2C=1N(C)CC1=CC=CC=C1 RQSVNURXHGGPTO-UHFFFAOYSA-N 0.000 description 1
- CUNLKSCXVUNDRS-UHFFFAOYSA-N 4-[4-[benzyl(methyl)amino]-7-morpholin-4-yl-6-phenylpteridin-2-yl]piperazine-1-carbaldehyde Chemical compound N=1C(N2CCN(CC2)C=O)=NC2=NC(N3CCOCC3)=C(C=3C=CC=CC=3)N=C2C=1N(C)CC1=CC=CC=C1 CUNLKSCXVUNDRS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3445298 | 1984-12-12 | ||
| DE19843445298 DE3445298A1 (de) | 1984-12-12 | 1984-12-12 | Neue pteridine, verfahren zu ihrer herstellung und deren verwendung als zwischenprodukte oder als arzneimittel |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI854862A0 FI854862A0 (fi) | 1985-12-10 |
| FI854862A7 FI854862A7 (fi) | 1986-06-13 |
| FI82696B FI82696B (fi) | 1990-12-31 |
| FI82696C true FI82696C (fi) | 1991-04-10 |
Family
ID=6252576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI854862A FI82696C (fi) | 1984-12-12 | 1985-12-10 | Foerfarande foer framstaellning av farmakologiskt vaerdefulla pteridiner. |
Country Status (15)
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7276506B2 (en) | 1998-12-28 | 2007-10-02 | 4 Aza Bioscience Nv | Immunosuppressive effects of pteridine derivatives |
| IL159540A0 (en) * | 2001-06-28 | 2004-06-01 | Pliva D D | Heterocyclic compounds as selective bacterial dhfr inhibitors and the uses thereof |
| DE10202468A1 (de) * | 2002-01-23 | 2004-09-30 | Faustus Forschungs Cie. Translational Cancer Research Gmbh | Pteridinderivate, Verfahren zu deren Herstellung und ihre Verwendung |
| PL1658081T3 (pl) * | 2003-08-29 | 2008-03-31 | 4 Aza Ip Nv | Pochodne pterydyny o działaniu immunosupresyjnym |
| PT1673092E (pt) * | 2003-10-17 | 2007-11-23 | 4 Aza Ip Nv | ''derivados de pteridina substituídos com heterociclos e sua utilização em terapia'' |
| GB2407089A (en) * | 2003-10-17 | 2005-04-20 | 4 Aza Bioscience Nv | Pteridine derivatives |
| AU2005221614A1 (en) * | 2004-03-04 | 2005-09-22 | Neurogen Corporation | Arylalkylamino-substituted quinazoline analogues |
| DE102004057645A1 (de) * | 2004-11-29 | 2006-06-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| DE102004057594A1 (de) | 2004-11-29 | 2006-06-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substitueirte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| DE102004057618A1 (de) | 2004-11-29 | 2006-06-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| DE102004057595A1 (de) | 2004-11-29 | 2006-06-08 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Substituierte Pteridine zur Behandlung von entzündlichen Erkrankungen |
| RU2445315C2 (ru) * | 2005-11-22 | 2012-03-20 | Кудос Фармасьютиклз Лимитед | ПРОИЗВОДНЫЕ ПИРИДО-, ПИРАЗО- И ПИРИМИДО-ПИРИМИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ИНГИБИТОРОВ mTOR |
| CA2628920C (en) * | 2005-11-22 | 2015-12-29 | Kudos Pharmaceuticals Limited | Pyrido-,pyrazo- and pyrimido-pyrimidine derivatives as mtor inhibitors |
| JP5440934B2 (ja) | 2006-05-24 | 2014-03-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 置換プテリジン |
| US10144736B2 (en) | 2006-07-20 | 2018-12-04 | Gilead Sciences, Inc. | Substituted pteridines useful for the treatment and prevention of viral infections |
| WO2008009078A2 (en) | 2006-07-20 | 2008-01-24 | Gilead Sciences, Inc. | 4,6-dl- and 2,4,6-trisubstituted quinazoline derivatives useful for treating viral infections |
| CA2659851C (en) | 2006-08-23 | 2014-02-25 | Kudos Pharmaceuticals Limited | 2-methylmorpholine pyrido-, pyrazo- and pyrimido-pyrimidine derivatives as mtor inhibitors |
| CN102137860B (zh) | 2008-06-20 | 2013-08-28 | 阿斯利康(瑞典)有限公司 | 吡啶并嘧啶化合物及其制备方法 |
| LT3097102T (lt) | 2015-03-04 | 2018-01-25 | Gilead Sciences, Inc. | 4,6-diamino-pirido[3,2-d]pirimidino junginiai, moduliuojantys į toll panašius receptorius |
| US10640499B2 (en) | 2016-09-02 | 2020-05-05 | Gilead Sciences, Inc. | Toll like receptor modulator compounds |
| MA46093A (fr) | 2016-09-02 | 2021-05-19 | Gilead Sciences Inc | Composés modulateurs du recepteur de type toll |
| TW202212339A (zh) | 2019-04-17 | 2022-04-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TWI751516B (zh) | 2019-04-17 | 2022-01-01 | 美商基利科學股份有限公司 | 類鐸受體調節劑之固體形式 |
| TWI879779B (zh) | 2019-06-28 | 2025-04-11 | 美商基利科學股份有限公司 | 類鐸受體調節劑化合物的製備方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3159628A (en) * | 1962-05-28 | 1964-12-01 | Smith Kline French Lab | Pteridine-5-oxide derivatives |
| DE3323932A1 (de) * | 1983-07-02 | 1985-01-10 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue 2-piperazino-pteridine, verfahren zu ihrer herstellung und diese verbindung enthaltende arzneimittel |
-
1984
- 1984-12-12 DE DE19843445298 patent/DE3445298A1/de not_active Withdrawn
-
1985
- 1985-12-05 EP EP85115459A patent/EP0185259A3/de not_active Ceased
- 1985-12-10 FI FI854862A patent/FI82696C/fi not_active IP Right Cessation
- 1985-12-11 ZA ZA859462A patent/ZA859462B/xx unknown
- 1985-12-11 ES ES549806A patent/ES8707238A1/es not_active Expired
- 1985-12-11 NO NO854965A patent/NO161373C/no unknown
- 1985-12-11 IL IL77294A patent/IL77294A/xx unknown
- 1985-12-11 DK DK572685A patent/DK161327C/da not_active IP Right Cessation
- 1985-12-11 JP JP60278859A patent/JPS61140585A/ja active Pending
- 1985-12-11 NZ NZ214522A patent/NZ214522A/xx unknown
- 1985-12-11 CA CA000497336A patent/CA1252783A/en not_active Expired
- 1985-12-11 PH PH33161A patent/PH24451A/en unknown
- 1985-12-11 PT PT81650A patent/PT81650B/pt not_active IP Right Cessation
- 1985-12-12 GR GR852996A patent/GR852996B/el unknown
- 1985-12-12 AU AU51232/85A patent/AU576924B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| IL77294A (en) | 1989-02-28 |
| GR852996B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-04-16 |
| DK161327B (da) | 1991-06-24 |
| NO854965L (no) | 1986-06-13 |
| PH24451A (en) | 1990-06-25 |
| EP0185259A3 (de) | 1989-03-01 |
| FI854862A7 (fi) | 1986-06-13 |
| JPS61140585A (ja) | 1986-06-27 |
| ZA859462B (en) | 1987-07-29 |
| NO161373C (no) | 1989-08-09 |
| DK161327C (da) | 1991-12-09 |
| PT81650B (pt) | 1988-04-21 |
| AU576924B2 (en) | 1988-09-08 |
| DK572685A (da) | 1986-06-13 |
| DK572685D0 (da) | 1985-12-11 |
| FI854862A0 (fi) | 1985-12-10 |
| CA1252783A (en) | 1989-04-18 |
| EP0185259A2 (de) | 1986-06-25 |
| AU5123285A (en) | 1986-06-19 |
| PT81650A (de) | 1986-01-01 |
| FI82696B (fi) | 1990-12-31 |
| ES549806A0 (es) | 1987-07-16 |
| ES8707238A1 (es) | 1987-07-16 |
| NO161373B (no) | 1989-05-02 |
| DE3445298A1 (de) | 1986-06-12 |
| NZ214522A (en) | 1988-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DR. KARL THOMAE GESELLSCHAFT MIT |