JP2003535864A - ６−フェニルピロロピリミジンジオン誘導体 - Google Patents
６−フェニルピロロピリミジンジオン誘導体Info
- Publication number
- JP2003535864A JP2003535864A JP2002501899A JP2002501899A JP2003535864A JP 2003535864 A JP2003535864 A JP 2003535864A JP 2002501899 A JP2002501899 A JP 2002501899A JP 2002501899 A JP2002501899 A JP 2002501899A JP 2003535864 A JP2003535864 A JP 2003535864A
- Authority
- JP
- Japan
- Prior art keywords
- group
- methyl
- propyl
- unsubstituted
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- BPZYTYKVRIOQSN-UHFFFAOYSA-N 6-phenylpyrrolo[3,2-d]pyrimidine-2,4-dione Chemical class C=1C2=NC(=O)NC(=O)C2=NC=1C1=CC=CC=C1 BPZYTYKVRIOQSN-UHFFFAOYSA-N 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 238000000034 method Methods 0.000 claims abstract description 86
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 238000004519 manufacturing process Methods 0.000 claims abstract description 24
- 239000000126 substance Substances 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 6
- 241001465754 Metazoa Species 0.000 claims abstract 3
- -1 hydroxy, phenyl Chemical group 0.000 claims description 120
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004193 piperazinyl group Chemical group 0.000 claims description 16
- 238000006467 substitution reaction Methods 0.000 claims description 15
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 11
- 125000005936 piperidyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 8
- GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 6
- 206010002383 Angina Pectoris Diseases 0.000 claims description 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 5
- 206010057671 Female sexual dysfunction Diseases 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 201000001881 impotence Diseases 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- PIWJZAXXTARPEJ-UHFFFAOYSA-N 7-chloro-6-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-3-methyl-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound C1=C(C2=C(C3=C(C(N(C)C(=O)N3CCC)=O)N2)Cl)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CC)CC1 PIWJZAXXTARPEJ-UHFFFAOYSA-N 0.000 claims description 4
- TZWQIZNDDVBBTO-UHFFFAOYSA-N 7-chloro-6-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-3-methyl-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound C1=C(C2=C(C3=C(C(N(C)C(=O)N3CCC)=O)N2)Cl)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 TZWQIZNDDVBBTO-UHFFFAOYSA-N 0.000 claims description 4
- 206010002388 Angina unstable Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 208000007814 Unstable Angina Diseases 0.000 claims description 4
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 206010006451 bronchitis Diseases 0.000 claims description 4
- 208000023819 chronic asthma Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 208000002815 pulmonary hypertension Diseases 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- 208000019553 vascular disease Diseases 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- FJSAYCNNSMESMW-UHFFFAOYSA-N 6-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-3-methyl-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound N1C=2C(=O)N(C)C(=O)N(CCC)C=2C=C1C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 FJSAYCNNSMESMW-UHFFFAOYSA-N 0.000 claims description 3
- LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims description 3
- QJHZALCNLOJLPG-UHFFFAOYSA-N 7-bromo-6-[5-[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-3-methyl-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound C1=C(C2=C(C3=C(C(N(C)C(=O)N3CCC)=O)N2)Br)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 QJHZALCNLOJLPG-UHFFFAOYSA-N 0.000 claims description 3
- DDWRYJJJTASJDZ-UHFFFAOYSA-N 7-chloro-3-methyl-6-[5-(4-methylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound C1=C(C2=C(C3=C(C(N(C)C(=O)N3CCC)=O)N2)Cl)C(OCCC)=CC=C1S(=O)(=O)N1CCN(C)CC1 DDWRYJJJTASJDZ-UHFFFAOYSA-N 0.000 claims description 3
- NJNCGTQUXJETDA-UHFFFAOYSA-N 7-chloro-6-[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-3-methyl-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound N1C=2C(=O)N(C)C(=O)N(CCC)C=2C(Cl)=C1C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 NJNCGTQUXJETDA-UHFFFAOYSA-N 0.000 claims description 3
- 206010061296 Motor dysfunction Diseases 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 230000002496 gastric effect Effects 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- PUULIDJFGBYZPM-UHFFFAOYSA-N 7-bromo-6-[5-[4-(3-hydroxypropyl)piperazin-1-yl]sulfonyl-2-propoxyphenyl]-3-methyl-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound C1=C(C2=C(C3=C(C(N(C)C(=O)N3CCC)=O)N2)Br)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCCO)CC1 PUULIDJFGBYZPM-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- IFJRBCXLSQITQK-UHFFFAOYSA-N CCCN1C2=C(CC(=N2)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCCC)C(=O)N(C1=O)C Chemical compound CCCN1C2=C(CC(=N2)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)C)OCCC)C(=O)N(C1=O)C IFJRBCXLSQITQK-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- FAWGIBHYNDVPJT-UHFFFAOYSA-N N=1C2=CN=CNC2=CC=1C1=CC=CC=C1 Chemical class N=1C2=CN=CNC2=CC=1C1=CC=CC=C1 FAWGIBHYNDVPJT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 22
- 206010059245 Angiopathy Diseases 0.000 claims 3
- 208000001647 Renal Insufficiency Diseases 0.000 claims 3
- 201000006370 kidney failure Diseases 0.000 claims 3
- 239000005864 Sulphur Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000005176 gastrointestinal motility Effects 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 7
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 7
- 101100296726 Caenorhabditis elegans pde-5 gene Proteins 0.000 abstract description 6
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 abstract description 5
- 239000003112 inhibitor Substances 0.000 abstract description 2
- LGOOLCMGKKGBHW-UHFFFAOYSA-N pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical class O=C1NC(=O)C2=NC=CC2=N1 LGOOLCMGKKGBHW-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 42
- 239000007787 solid Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 230000014759 maintenance of location Effects 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 7
- SHQYZHCVGVXICO-UHFFFAOYSA-N 6-phenyl-1,5-dihydropyrrolo[3,2-d]pyrimidine-2,4-dione Chemical class N1C=2C(=O)NC(=O)NC=2C=C1C1=CC=CC=C1 SHQYZHCVGVXICO-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 4
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- GBLNSFUQJHRVKQ-UHFFFAOYSA-N 6-[5-(4-ethylpiperazin-1-yl)sulfonyl-2-propoxyphenyl]-3-methyl-1-propyl-5h-pyrrolo[3,2-d]pyrimidine-2,4-dione Chemical compound C1=C(C=2NC=3C(=O)N(C)C(=O)N(CCC)C=3C=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CC)CC1 GBLNSFUQJHRVKQ-UHFFFAOYSA-N 0.000 description 3
- HGOSTGHMGXUZSB-UHFFFAOYSA-N 6-phenyl-1,7-dihydropyrrolo[3,2-d]pyrimidine-2,4-dione Chemical class C1(=CC=CC=C1)C=1CC=2NC(NC(C=2N=1)=O)=O HGOSTGHMGXUZSB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- GLFKEPZEPYKDJM-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)-3-(3-methyl-2,4-dioxo-1-propyl-5h-pyrrolo[3,2-d]pyrimidin-6-yl)-4-propoxybenzenesulfonamide Chemical compound CCCOC1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1C(N1)=CC2=C1C(=O)N(C)C(=O)N2CCC GLFKEPZEPYKDJM-UHFFFAOYSA-N 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008085 renal dysfunction Effects 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 239000003643 water by type 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200001436 | 2000-06-07 | ||
| ES200001436 | 2000-06-07 | ||
| PCT/EP2001/006306 WO2001094350A1 (en) | 2000-06-07 | 2001-06-01 | 6-phenylpyrrolopyrimidinedione derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003535864A true JP2003535864A (ja) | 2003-12-02 |
| JP2003535864A5 JP2003535864A5 (cg-RX-API-DMAC7.html) | 2008-07-17 |
Family
ID=8493813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002501899A Withdrawn JP2003535864A (ja) | 2000-06-07 | 2001-06-01 | ６−フェニルピロロピリミジンジオン誘導体 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6943253B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1286997B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2003535864A (cg-RX-API-DMAC7.html) |
| AR (1) | AR030424A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE273980T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2001281802A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2411013A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60105020T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2222389T3 (cg-RX-API-DMAC7.html) |
| MY (1) | MY133995A (cg-RX-API-DMAC7.html) |
| PE (1) | PE20020219A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2001094350A1 (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013503131A (ja) * | 2009-08-26 | 2013-01-31 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | メチルピロロピリミジンカルボキサミド |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2193839B1 (es) * | 2001-06-22 | 2005-02-16 | Almirall Prodesfarma, S.A. | Nuevos derivados de 6-fenildihidropirrolpirimidindiona. |
| ES2208063B1 (es) | 2002-04-01 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de la 4-(pirrolopirimidin-6-il)bencenosulfonamida. |
| DE10229778A1 (de) * | 2002-07-03 | 2004-01-29 | Bayer Ag | Neue Verwendung von Imidazotriazinonen |
| US20070010450A1 (en) * | 2003-06-13 | 2007-01-11 | Microbia, Inc., A Massachusetts Corporation | Methods and compositions for the treatment of gastrointestinal disorders |
| KR20060111467A (ko) | 2003-10-31 | 2006-10-27 | 씨브이 쎄러퓨틱스, 인코포레이티드 | Ａ2ｂ 아데노신 수용체 안타고니스트 |
| EP2258357A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| WO2007053596A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| JP2009536667A (ja) | 2006-05-09 | 2009-10-15 | ブレインセルス，インコーポレイティド | ５ｈｔ受容体介在性の神経新生 |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| KR20090064418A (ko) | 2006-09-08 | 2009-06-18 | 브레인셀즈 인코퍼레이션 | 4-아실아미노피리딘 유도체 포함 조합물 |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| AR079451A1 (es) | 2009-12-18 | 2012-01-25 | Nycomed Gmbh | Compuestos 3,4,4a,10b-tetrahidro-1h-tiopirano[4,3-c]isoquinolina |
| AT512084A1 (de) * | 2011-10-20 | 2013-05-15 | Univ Wien Tech | Diazabicyclo- und diazaspiro-alkanderivate als phosphodiesterase-5 inhibitoren |
| EP2804603A1 (en) | 2012-01-10 | 2014-11-26 | President and Fellows of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| AR103297A1 (es) | 2014-12-30 | 2017-05-03 | Forma Therapeutics Inc | Pirrolo y pirazolopirimidinas como inhibidores de la proteasa 7 específica de ubiquitina |
| MA41291A (fr) | 2014-12-30 | 2017-11-07 | Forma Therapeutics Inc | Dérivés de la pyrrolotriazinone et de l'imidazotriazinone en tant qu'inhibiteurs de la protéase spécifique de l'ubiquitine n° 7 (usp7) pour le traitement d'un cancer |
| JP2018504432A (ja) | 2015-02-05 | 2018-02-15 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的プロテアーゼ７阻害物質としてのイソチアゾロピリミジノン、ピラゾロピリミジノン及びピロロピリミジノン |
| EP3253738A1 (en) | 2015-02-05 | 2017-12-13 | Forma Therapeutics, Inc. | Quinazolinones and azaquinazolinones as ubiquitin-specific protease 7 inhibitors |
| EP3253765A1 (en) | 2015-02-05 | 2017-12-13 | Forma Therapeutics, Inc. | Thienopyrimidinones as ubiquitin-specific protease 7 inhibitors |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5260322A (en) | 1990-10-08 | 1993-11-09 | Merck & Co., Inc. | Angiotension II antagonists in the treatment of hyperuricemia |
| FR2737494B1 (fr) * | 1995-08-04 | 1997-08-29 | Synthelabo | Derives de benzenesulfonamide, leur preparation et leur application en therapeutique |
| AU4501199A (en) * | 1998-06-03 | 1999-12-20 | Almirall Prodesfarma S.A. | 8-phenylxanthine derivatives and their use as phosphodiesterase inhibitors |
-
2001
- 2001-06-01 WO PCT/EP2001/006306 patent/WO2001094350A1/en not_active Ceased
- 2001-06-01 JP JP2002501899A patent/JP2003535864A/ja not_active Withdrawn
- 2001-06-01 AT AT01960264T patent/ATE273980T1/de not_active IP Right Cessation
- 2001-06-01 AU AU2001281802A patent/AU2001281802A1/en not_active Abandoned
- 2001-06-01 DE DE60105020T patent/DE60105020T2/de not_active Expired - Lifetime
- 2001-06-01 ES ES01960264T patent/ES2222389T3/es not_active Expired - Lifetime
- 2001-06-01 EP EP01960264A patent/EP1286997B1/en not_active Expired - Lifetime
- 2001-06-01 CA CA002411013A patent/CA2411013A1/en not_active Abandoned
- 2001-06-06 AR ARP010102696A patent/AR030424A1/es unknown
- 2001-06-06 MY MYPI20012656 patent/MY133995A/en unknown
- 2001-06-06 PE PE2001000521A patent/PE20020219A1/es not_active Application Discontinuation
-
2002
- 2002-12-06 US US10/313,922 patent/US6943253B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013503131A (ja) * | 2009-08-26 | 2013-01-31 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | メチルピロロピリミジンカルボキサミド |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60105020T2 (de) | 2005-08-18 |
| AR030424A1 (es) | 2003-08-20 |
| US6943253B2 (en) | 2005-09-13 |
| ATE273980T1 (de) | 2004-09-15 |
| WO2001094350A1 (en) | 2001-12-13 |
| PE20020219A1 (es) | 2002-04-17 |
| ES2222389T3 (es) | 2005-02-01 |
| MY133995A (en) | 2007-11-30 |
| US20030232838A1 (en) | 2003-12-18 |
| CA2411013A1 (en) | 2001-12-13 |
| EP1286997B1 (en) | 2004-08-18 |
| EP1286997A1 (en) | 2003-03-05 |
| DE60105020D1 (de) | 2004-09-23 |
| AU2001281802A1 (en) | 2001-12-17 |
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