SK76699A3 - Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments - Google Patents

Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments Download PDF

Info

Publication number: SK76699A3
Authority: SK; Slovakia
Prior art keywords: formula; methyl; pyrrolo; methylpropyl; naphthalenylmethyl
Prior art date: 1996-12-21

Application number

SK766-99A

Other languages

English (en)

Slovak (sk)

Inventor

Martin Cooper

David Cheshire

David Donald

Mark Furber

Matthew Perry

Richard Harrison

Nicholas Tomkinson

Original Assignee

Astra Pharma Prod

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-12-21

Filing date

1997-12-18

Publication date

2000-05-16

1997-12-18 Application filed by Astra Pharma Prod filed Critical Astra Pharma Prod

2000-05-16 Publication of SK76699A3 publication Critical patent/SK76699A3/sk

Links

239000003814 drug Substances 0.000 title claims description 3
TUWOCBICGNGPKL-UHFFFAOYSA-N pyrrolo[3,4-d]pyrimidin-2-one Chemical class O=C1N=CC2=CN=CC2=N1 TUWOCBICGNGPKL-UHFFFAOYSA-N 0.000 title 1
-1 5-substituted pyrrolo[3,4-d]pyrimidine-2,4-diones Chemical class 0.000 claims abstract description 93
238000000034 method Methods 0.000 claims abstract description 27
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 8
238000004519 manufacturing process Methods 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 141
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 59
229910052739 hydrogen Inorganic materials 0.000 claims description 54
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 25
125000003118 aryl group Chemical group 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 14
125000003107 substituted aryl group Chemical group 0.000 claims description 14
OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 13
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
QWJUXNNLZSSYIY-UHFFFAOYSA-N 5-(3-hydroxypropylsulfinyl)-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2C(CN3C=C4N(C(N(C)C(=O)C4=C3S(=O)CCCO)=O)CC(C)C)=CC=CC2=C1 QWJUXNNLZSSYIY-UHFFFAOYSA-N 0.000 claims description 8
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 7
125000003831 tetrazolyl group Chemical class 0.000 claims description 7
239000002671 adjuvant Substances 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical class 0.000 claims description 5
239000003054 catalyst Substances 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
RIBFGELHONOBMS-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)-5-pyridin-2-ylsulfanylpyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(CC(C)C)C2=CN(CC=2C3=CC=CC=C3C=CC=2)C=1SC1=CC=CC=N1 RIBFGELHONOBMS-UHFFFAOYSA-N 0.000 claims description 3
JKVBLEJNIJDLLB-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)-5-pyridin-4-ylsulfanylpyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(CC(C)C)C2=CN(CC=2C3=CC=CC=C3C=CC=2)C=1SC1=CC=NC=C1 JKVBLEJNIJDLLB-UHFFFAOYSA-N 0.000 claims description 3
RRKDJNNRHVJFBA-UHFFFAOYSA-N 5-(3-methoxyphenyl)sulfanyl-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound COC1=CC=CC(SC2=C3C(=O)N(C)C(=O)N(CC(C)C)C3=CN2CC=2C3=CC=CC=C3C=CC=2)=C1 RRKDJNNRHVJFBA-UHFFFAOYSA-N 0.000 claims description 3
CXBWQHLLEQSBPA-UHFFFAOYSA-N 5-(4-methoxyphenyl)sulfanyl-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C1=CC(OC)=CC=C1SC1=C2C(=O)N(C)C(=O)N(CC(C)C)C2=CN1CC1=CC=CC2=CC=CC=C12 CXBWQHLLEQSBPA-UHFFFAOYSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
208000027771 Obstructive airways disease Diseases 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000001273 butane Substances 0.000 claims description 3
KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 3
230000001506 immunosuppresive effect Effects 0.000 claims description 3
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 3
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 3
230000002441 reversible effect Effects 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
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 2
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 2
RFCFLBXXGNQVOS-UHFFFAOYSA-N 5-(2-hydroxyphenyl)sulfanyl-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(CC(C)C)C2=CN(CC=2C3=CC=CC=C3C=CC=2)C=1SC1=CC=CC=C1O RFCFLBXXGNQVOS-UHFFFAOYSA-N 0.000 claims description 2
JKIMVDWAUSGDSO-UHFFFAOYSA-N 5-(3-hydroxypropylsulfonyl)-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2C(CN3C=C4N(C(N(C)C(=O)C4=C3S(=O)(=O)CCCO)=O)CC(C)C)=CC=CC2=C1 JKIMVDWAUSGDSO-UHFFFAOYSA-N 0.000 claims description 2
ASRYKYHHHXCVKB-UHFFFAOYSA-N 5-(3-methoxypropylsulfanyl)-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C1=C2N(CC(C)C)C(=O)N(C)C(=O)C2=C(SCCCOC)N1CC1=CC=CC2=CC=CC=C12 ASRYKYHHHXCVKB-UHFFFAOYSA-N 0.000 claims description 2
CFYJGQPJOSKZNX-UHFFFAOYSA-N 5-(4-hydroxyphenyl)sulfanyl-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(CC(C)C)C2=CN(CC=2C3=CC=CC=C3C=CC=2)C=1SC1=CC=C(O)C=C1 CFYJGQPJOSKZNX-UHFFFAOYSA-N 0.000 claims description 2
ALHXPDPZFWWXCS-UHFFFAOYSA-N 6-(2,3-dihydro-1h-inden-2-yl)-5-(3-hydroxypropylsulfinyl)-3-methyl-1-propan-2-ylpyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C1C2=CC=CC=C2CC1N1C=C2N(C(C)C)C(=O)N(C)C(=O)C2=C1S(=O)CCCO ALHXPDPZFWWXCS-UHFFFAOYSA-N 0.000 claims description 2
101150065749 Churc1 gene Proteins 0.000 claims description 2
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 claims description 2
206010062016 Immunosuppression Diseases 0.000 claims description 2
102100038239 Protein Churchill Human genes 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000005956 isoquinolyl group Chemical group 0.000 claims description 2
HLBHHRWDKUQESF-UHFFFAOYSA-N methyl 4-[3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)-2,4-dioxopyrrolo[3,4-d]pyrimidin-5-yl]sulfanylbutanoate Chemical compound C1=C2N(CC(C)C)C(=O)N(C)C(=O)C2=C(SCCCC(=O)OC)N1CC1=CC=CC2=CC=CC=C12 HLBHHRWDKUQESF-UHFFFAOYSA-N 0.000 claims description 2
150000002905 orthoesters Chemical class 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
125000005493 quinolyl group Chemical group 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims 2
125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
LSDQVYBIWRXOQJ-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)-5-[3-(2h-tetrazol-5-yl)propylsulfanyl]pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C=12C(=O)N(C)C(=O)N(CC(C)C)C2=CN(CC=2C3=CC=CC=C3C=CC=2)C=1SCCCC1=NN=NN1 LSDQVYBIWRXOQJ-UHFFFAOYSA-N 0.000 claims 1
QPMBKUWHQJMFBK-UHFFFAOYSA-N 5-[3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)-2,4-dioxopyrrolo[3,4-d]pyrimidin-5-yl]pentanoic acid Chemical compound C1=CC=C2C(CN3C=C4N(C(N(C)C(=O)C4=C3CCCCC(O)=O)=O)CC(C)C)=CC=CC2=C1 QPMBKUWHQJMFBK-UHFFFAOYSA-N 0.000 claims 1
206010009944 Colon cancer Diseases 0.000 claims 1
125000002947 alkylene group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
239000000243 solution Substances 0.000 description 50
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
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238000005481 NMR spectroscopy Methods 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 23
238000002844 melting Methods 0.000 description 22
230000008018 melting Effects 0.000 description 22
239000000203 mixture Substances 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
239000012267 brine Substances 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 12
235000019341 magnesium sulphate Nutrition 0.000 description 12
229910000029 sodium carbonate Inorganic materials 0.000 description 11
239000002904 solvent Substances 0.000 description 11
150000003839 salts Chemical class 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
208000006673 asthma Diseases 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
239000000284 extract Substances 0.000 description 7
239000006260 foam Substances 0.000 description 7
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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239000000460 chlorine Substances 0.000 description 6
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
HSGYYWSMLDCHQO-UHFFFAOYSA-N 3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound C1=CC=C2C(CN3C=C4N(C(N(C)C(=O)C4=C3)=O)CC(C)C)=CC=CC2=C1 HSGYYWSMLDCHQO-UHFFFAOYSA-N 0.000 description 5
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125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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125000003342 alkenyl group Chemical group 0.000 description 3
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238000007796 conventional method Methods 0.000 description 3
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000007799 mixed lymphocyte reaction assay Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
230000036473 myasthenia Effects 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
DSBOPXOKGKIRSG-UHFFFAOYSA-N pyrrolo[3,4-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C2=CN=CC2=N1 DSBOPXOKGKIRSG-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
230000006340 racemization Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
201000000306 sarcoidosis Diseases 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
238000003419 tautomerization reaction Methods 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
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- 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
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Immunology (AREA)
Dermatology (AREA)
Neurology (AREA)
Diabetes (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Neurosurgery (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Communicable Diseases (AREA)
Vascular Medicine (AREA)
Transplantation (AREA)
Hematology (AREA)
Oncology (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK766-99A 1996-12-21 1997-12-18 Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments SK76699A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9626643.2A GB9626643D0 (en)	1996-12-21	1996-12-21	Compounds
PCT/SE1997/002157 WO1998028301A1 (en)	1996-12-21	1997-12-18	Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments

Publications (1)

Publication Number	Publication Date
SK76699A3 true SK76699A3 (en)	2000-05-16

Family

ID=10804862

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK766-99A SK76699A3 (en)	1996-12-21	1997-12-18	Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments

Country Status (23)

Country	Link
US (8)	US6046204A (no)
EP (1)	EP0946562B1 (no)
JP (1)	JP2001507687A (no)
KR (1)	KR20000069605A (no)
CN (1)	CN1246119A (no)
AT (1)	ATE215088T1 (no)
AU (1)	AU717429B2 (no)
BR (1)	BR9714063A (no)
CA (1)	CA2275312A1 (no)
CZ (1)	CZ289925B6 (no)
DE (1)	DE69711430T2 (no)
EE (1)	EE9900315A (no)
GB (1)	GB9626643D0 (no)
HU (1)	HUP0002839A3 (no)
ID (1)	ID21682A (no)
IL (1)	IL130538A0 (no)
IS (1)	IS5082A (no)
NO (1)	NO993027L (no)
NZ (1)	NZ336124A (no)
PL (1)	PL334228A1 (no)
SK (1)	SK76699A3 (no)
TR (1)	TR199901433T2 (no)
WO (1)	WO1998028301A1 (no)

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SE9801399D0 (sv)	1998-04-21	1998-04-21	Astra Pharma Prod	Method and apparatus for filling containers
ATE356810T1 (de)	1999-01-15	2007-04-15	Altana Pharma Ag	Polysubstituted 6-phenylphenanthridines mit pde- iv hemmender wirkung
WO2000042034A1 (en)	1999-01-15	2000-07-20	Byk Gulden	Phenanthridine-n-oxides with pde-iv inhibiting activity
AU2107700A (en)	1999-01-15	2000-08-01	Byk Gulden Lomberg Chemische Fabrik Gmbh	Phenanthridine-n-oxides with pde-iv inhibiting activity
US6361486B1 (en) *	2000-02-29	2002-03-26	Agilent Technologies, Inc.	Coaxial-drive centrifuge providing tilt control relative to centrifugal force
AU2001281255B2 (en) *	2000-08-14	2006-07-20	Ortho-Mcneil Pharmaceutical, Inc.	Substituted pyrazoles
US20070105841A1 (en) *	2000-08-14	2007-05-10	Breitenbucher J G	Method for treating allergies using substituted pyrazoles
TW200407315A (en) *	2002-04-23	2004-05-16	Sankyo Co	Pyrimidine derivatives
CA2533534C (en) *	2003-07-24	2013-03-19	Tecomet, Inc.	Assembled non-random foams
WO2006115509A2 (en)	2004-06-24	2006-11-02	Novartis Vaccines And Diagnostics Inc.	Small molecule immunopotentiators and assays for their detection
MY140748A (en)	2004-12-06	2010-01-15	Astrazeneca Ab	Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy
US8198288B2 (en)	2006-05-04	2012-06-12	Pulmagen Therapeutics (Inflammation) Limited	Tetrahydropyrrolopyrimidinediones and their use in therapy
PT2024367E (pt)	2006-05-04	2010-12-03	Pulmagen Therapeutics Inflammation Ltd	Tetra-hidropirrolopirimidinadionas e a sua utilização a título de inibidores da elastase de neutrófilos humana
MX2008015489A (es)	2006-06-06	2009-01-13	Intra Cellular Therapies Inc	Compuestos organicos.
ES2588238T3 (es)	2007-12-06	2016-10-31	Intra-Cellular Therapies, Inc.	Derivados de pirazolopirimidin-4,6-diona y su uso como producto farmacéutico
WO2009100403A1 (en) *	2008-02-07	2009-08-13	Neurogen Corporation	Substituted aryl pyrimidinones
MA32939B1 (fr) *	2008-12-06	2012-01-02	Intra Cellular Therapies Inc	Composes organiques
US8859564B2 (en)	2008-12-06	2014-10-14	Intra-Cellular Therapies, Inc.	Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione derivatives useful as inhibitors of phosphodiesterase 1
AU2009322905A1 (en)	2008-12-06	2010-06-10	Intra-Cellular Therapies, Inc.	Organic compounds
IN2012DN00719A (no)	2009-08-10	2015-06-19	Univ California
US9371327B2 (en)	2010-05-31	2016-06-21	Intra-Cellular Therapies, Inc.	PDE1 inhibitor compounds
JP5879336B2 (ja)	2010-05-31	2016-03-08	イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−ＣｅｌｌｕｌａｒＴｈｅｒａｐｉｅｓ，Ｉｎｃ．	有機化合物
US9062073B2 (en)	2011-05-27	2015-06-23	The Regents Of The University Of California	Pyrimido-pyrrolo-oxazine-dione compound inhibitors of the cystic fibrosis transmembrane conductance regulator protein and uses therefor
US9546175B2 (en)	2014-08-07	2017-01-17	Intra-Cellular Therapies, Inc.	Organic compounds
CN108129486B (zh) *	2018-01-25	2020-06-05	华东理工大学	嘧啶酮衍生物及其用途

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WO1993004047A1 (en) *	1991-08-16	1993-03-04	Merck & Co., Inc.	Quinazoline derivatives as inhibitors of hiv reverse transcriptase
GB9424842D0 (en) *	1994-12-09	1995-02-08	British Tech Group	Pharmaceutical compositions

1996
- 1996-12-21 GB GBGB9626643.2A patent/GB9626643D0/en active Pending
1997
- 1997-12-18 IL IL13053897A patent/IL130538A0/xx unknown
- 1997-12-18 CZ CZ19992204A patent/CZ289925B6/cs not_active IP Right Cessation
- 1997-12-18 KR KR1019997005595A patent/KR20000069605A/ko not_active Application Discontinuation
- 1997-12-18 EP EP97952146A patent/EP0946562B1/en not_active Expired - Lifetime
- 1997-12-18 PL PL97334228A patent/PL334228A1/xx unknown
- 1997-12-18 WO PCT/SE1997/002157 patent/WO1998028301A1/en not_active Application Discontinuation
- 1997-12-18 SK SK766-99A patent/SK76699A3/sk unknown
- 1997-12-18 TR TR1999/01433T patent/TR199901433T2/xx unknown
- 1997-12-18 HU HU0002839A patent/HUP0002839A3/hu unknown
- 1997-12-18 DE DE69711430T patent/DE69711430T2/de not_active Expired - Fee Related
- 1997-12-18 JP JP52869798A patent/JP2001507687A/ja not_active Ceased
- 1997-12-18 EE EEP199900315A patent/EE9900315A/xx unknown
- 1997-12-18 BR BR9714063-5A patent/BR9714063A/pt not_active IP Right Cessation
- 1997-12-18 AU AU55809/98A patent/AU717429B2/en not_active Ceased
- 1997-12-18 AT AT97952146T patent/ATE215088T1/de active
- 1997-12-18 CA CA002275312A patent/CA2275312A1/en not_active Abandoned
- 1997-12-18 NZ NZ336124A patent/NZ336124A/en unknown
- 1997-12-18 CN CN97181811A patent/CN1246119A/zh active Pending
- 1997-12-18 US US09/011,780 patent/US6046204A/en not_active Expired - Fee Related
- 1997-12-18 ID IDW990507A patent/ID21682A/id unknown
1999
- 1999-06-14 IS IS5082A patent/IS5082A/is unknown
- 1999-06-18 NO NO993027A patent/NO993027L/no not_active Application Discontinuation
2000
- 2000-02-17 US US09/506,090 patent/US6166206A/en not_active Expired - Fee Related
- 2000-02-17 US US09/505,857 patent/US6136974A/en not_active Expired - Fee Related
- 2000-02-17 US US09/506,091 patent/US6229013B1/en not_active Expired - Fee Related
- 2000-02-17 US US09/505,862 patent/US6211368B1/en not_active Expired - Fee Related
- 2000-11-08 US US09/707,880 patent/US6306863B1/en not_active Expired - Fee Related
2001
- 2001-10-09 US US09/971,709 patent/US20020025966A1/en not_active Abandoned
2003
- 2003-03-05 US US10/378,913 patent/US20030162798A1/en not_active Abandoned

Also Published As

Publication number	Publication date
US6229013B1 (en)	2001-05-08
IS5082A (is)	1999-06-14
DE69711430T2 (de)	2002-10-31
HUP0002839A3 (en)	2001-04-28
CA2275312A1 (en)	1998-07-02
ID21682A (id)	1999-07-08
NO993027L (no)	1999-08-20
GB9626643D0 (en)	1997-02-12
BR9714063A (pt)	2002-01-02
EE9900315A (et)	2000-02-15
EP0946562B1 (en)	2002-03-27
PL334228A1 (en)	2000-02-14
KR20000069605A (ko)	2000-11-25
CZ289925B6 (cs)	2002-04-17
CN1246119A (zh)	2000-03-01
AU5580998A (en)	1998-07-17
US6136974A (en)	2000-10-24
US6166206A (en)	2000-12-26
DE69711430D1 (de)	2002-05-02
HUP0002839A2 (hu)	2001-02-28
US6046204A (en)	2000-04-04
NO993027D0 (no)	1999-06-18
US20020025966A1 (en)	2002-02-28
WO1998028301A1 (en)	1998-07-02
AU717429B2 (en)	2000-03-23
US20030162798A1 (en)	2003-08-28
ATE215088T1 (de)	2002-04-15
IL130538A0 (en)	2000-06-01
US6211368B1 (en)	2001-04-03
NZ336124A (en)	2001-03-30
CZ220499A3 (cs)	2000-02-16
EP0946562A1 (en)	1999-10-06
JP2001507687A (ja)	2001-06-12
US6306863B1 (en)	2001-10-23
TR199901433T2 (xx)	1999-09-21

Publication	Publication Date	Title
SK76699A3 (en)	2000-05-16	Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments
CA2150709C (en)	1999-03-16	Pyrazolopyrimidines
US20050032808A1 (en)	2005-02-10	5 6-diaryl-pyrazine-2-amide derivatives as cb1 antagonists
EP3983064B1 (en)	2024-03-06	Cot modulators and methods of use thereof
SK151399A3 (en)	2000-05-16	Thieno[2,3-d]pyrimidine diones, preparation method thereof, pharmaceutical compositions containing the same and their use
KR20010006350A (ko)	2001-01-26	신규 화합물
CZ20021743A3 (cs)	2002-08-14	Bicyklické dusíkové heterocykly substituované alkylaminoskupinou jako inhibitory P38 proteinkinázy
WO1995028387A1 (fr)	1995-10-26	Compose benzamide et utilisation medicale dudit compose
US9260448B2 (en)	2016-02-16	Thienopyrimidinone derivatives as mGluR1 antagonists
KR19980039641A (ko)	1998-08-17	4,5-디아미노 피리미딘 유도체 및 이의 제조방법
SK118798A3 (en)	1999-03-12	Pharmaceutically useful compounds
CA1293727C (en)	1991-12-31	9-deazaguanines
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