HRP20030226A2 - 2,5-DIHYDRO-PYRAZOLO[3,4-d]PYRIMIDIN-4-ONES WITH AN ANTICONVULSIVE ACTION AND METHODS FOR PRODUCING THE SAME - Google Patents
2,5-DIHYDRO-PYRAZOLO[3,4-d]PYRIMIDIN-4-ONES WITH AN ANTICONVULSIVE ACTION AND METHODS FOR PRODUCING THE SAME Download PDFInfo
- Publication number
- HRP20030226A2 HRP20030226A2 HR20030226A HRP20030226A HRP20030226A2 HR P20030226 A2 HRP20030226 A2 HR P20030226A2 HR 20030226 A HR20030226 A HR 20030226A HR P20030226 A HRP20030226 A HR P20030226A HR P20030226 A2 HRP20030226 A2 HR P20030226A2
- Authority
- HR
- Croatia
- Prior art keywords
- pyrimidin
- dihydropyrazolo
- methyl
- phenyl
- difluorobenzyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 230000002082 anti-convulsion Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 35
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- FQXKRMCCAZDGMY-UHFFFAOYSA-N 5-benzyl-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC=2NN=CC=2C(=O)N1CC1=CC=CC=C1 FQXKRMCCAZDGMY-UHFFFAOYSA-N 0.000 claims description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- FBZVZUSVGKOWHG-UHFFFAOYSA-N 1,1-dimethoxy-n,n-dimethylethanamine Chemical compound COC(C)(OC)N(C)C FBZVZUSVGKOWHG-UHFFFAOYSA-N 0.000 claims description 3
- DYUCRIIUUWXRGB-UHFFFAOYSA-N 2-methyl-5-[(2-methylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1CN1C(=O)C2=CN(C)N=C2N=C1 DYUCRIIUUWXRGB-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- WJTGTXAPWHRKJU-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=CC=C1CN1C(=O)C2=CNN=C2N=C1 WJTGTXAPWHRKJU-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims description 3
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical class 0.000 claims description 2
- RRCUCKWZTGAACQ-UHFFFAOYSA-N 2,5-bis[(2-chlorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=CC=C1CN1N=C(N=CN(CC=2C(=CC=CC=2)Cl)C2=O)C2=C1 RRCUCKWZTGAACQ-UHFFFAOYSA-N 0.000 claims description 2
- OOZQCNPEQHJQBC-UHFFFAOYSA-N 2,6-dimethyl-5-[[2-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=NN(C)C=C2C(=O)N1CC1=CC=CC=C1C(F)(F)F OOZQCNPEQHJQBC-UHFFFAOYSA-N 0.000 claims description 2
- YGIFRYMSBNDQID-UHFFFAOYSA-N 2-[(2-methyl-4-oxopyrazolo[3,4-d]pyrimidin-5-yl)methyl]benzonitrile Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=C1C#N YGIFRYMSBNDQID-UHFFFAOYSA-N 0.000 claims description 2
- SHFSNBRDZVHGNV-UHFFFAOYSA-N 2-benzyl-5-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC2=NN(CC=3C=CC=CC=3)C=C2C(=O)N1CC1=CC=CC=N1 SHFSNBRDZVHGNV-UHFFFAOYSA-N 0.000 claims description 2
- AYBHOOVUHQJEJD-UHFFFAOYSA-N 2-benzyl-5-[(2-chloro-6-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(Cl)=C1CN1C(=O)C2=CN(CC=3C=CC=CC=3)N=C2N=C1 AYBHOOVUHQJEJD-UHFFFAOYSA-N 0.000 claims description 2
- MAFPHHBENANVJF-UHFFFAOYSA-N 2-butyl-5-[(2,6-difluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CCCC)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1F MAFPHHBENANVJF-UHFFFAOYSA-N 0.000 claims description 2
- NDXKGEYOKAKTNG-UHFFFAOYSA-N 2-butyl-5-[(2-chloro-6-fluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CCCC)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1Cl NDXKGEYOKAKTNG-UHFFFAOYSA-N 0.000 claims description 2
- FPNSKPWZRRQHRJ-UHFFFAOYSA-N 2-butyl-5-[(4-methylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CCCC)C=C(C2=O)C=1N=CN2CC1=CC=C(C)C=C1 FPNSKPWZRRQHRJ-UHFFFAOYSA-N 0.000 claims description 2
- LWLSSXOUTGHQQK-UHFFFAOYSA-N 2-ethyl-5-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CC)C=C(C2=O)C=1N=CN2CC1=CC=CC=N1 LWLSSXOUTGHQQK-UHFFFAOYSA-N 0.000 claims description 2
- VVIUJICXFDNDNN-UHFFFAOYSA-N 2-ethyl-5-[(4-methylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CC)C=C(C2=O)C=1N=CN2CC1=CC=C(C)C=C1 VVIUJICXFDNDNN-UHFFFAOYSA-N 0.000 claims description 2
- IMSDXMGUPCGVFA-UHFFFAOYSA-N 2-methyl-5-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=N1 IMSDXMGUPCGVFA-UHFFFAOYSA-N 0.000 claims description 2
- LZESYJSTDCRAGF-UHFFFAOYSA-N 2-methyl-5-(pyridin-4-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=NC=C1 LZESYJSTDCRAGF-UHFFFAOYSA-N 0.000 claims description 2
- SDQGENBCCSDKES-UHFFFAOYSA-N 2-methyl-5-[(2,4,6-trimethylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC(C)=CC(C)=C1CN1C(=O)C2=CN(C)N=C2N=C1 SDQGENBCCSDKES-UHFFFAOYSA-N 0.000 claims description 2
- DLKKGOVPGFVOOE-UHFFFAOYSA-N 2-methyl-5-[(2-nitrophenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=C1[N+]([O-])=O DLKKGOVPGFVOOE-UHFFFAOYSA-N 0.000 claims description 2
- FQDACLZICMVLNJ-UHFFFAOYSA-N 2-methyl-5-[(2-phenylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=C1C1=CC=CC=C1 FQDACLZICMVLNJ-UHFFFAOYSA-N 0.000 claims description 2
- BAVFPCSZADUCDT-UHFFFAOYSA-N 2-methyl-5-[(3-methylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC(CN2C(C3=CN(C)N=C3N=C2)=O)=C1 BAVFPCSZADUCDT-UHFFFAOYSA-N 0.000 claims description 2
- CQOHVQHTTXMVTG-UHFFFAOYSA-N 2-methyl-5-[(4-methylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C2=CN(C)N=C2N=C1 CQOHVQHTTXMVTG-UHFFFAOYSA-N 0.000 claims description 2
- FRSGBYWHJGCHKX-UHFFFAOYSA-N 2-methyl-5-[[2-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=C1C(F)(F)F FRSGBYWHJGCHKX-UHFFFAOYSA-N 0.000 claims description 2
- MHGKLUYLLRSBIX-UHFFFAOYSA-N 2-methyl-5-[[4-(trifluoromethyl)phenyl]methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=C(C(F)(F)F)C=C1 MHGKLUYLLRSBIX-UHFFFAOYSA-N 0.000 claims description 2
- JRFNAQLMVSMCTO-UHFFFAOYSA-N 2-phenyl-5-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC2=NN(C=3C=CC=CC=3)C=C2C(=O)N1CC1=CC=CC=N1 JRFNAQLMVSMCTO-UHFFFAOYSA-N 0.000 claims description 2
- PWPUPHKWFDZROA-UHFFFAOYSA-N 2-propan-2-yl-5-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C(C)C)C=C(C2=O)C=1N=CN2CC1=CC=CC=N1 PWPUPHKWFDZROA-UHFFFAOYSA-N 0.000 claims description 2
- GMMNYEDDZHEUPA-UHFFFAOYSA-N 2-propyl-5-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CCC)C=C(C2=O)C=1N=CN2CC1=CC=CC=N1 GMMNYEDDZHEUPA-UHFFFAOYSA-N 0.000 claims description 2
- SQXPLWUIEHGLKW-UHFFFAOYSA-N 5-(pyridin-2-ylmethyl)-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC2=NNC=C2C(=O)N1CC1=CC=CC=N1 SQXPLWUIEHGLKW-UHFFFAOYSA-N 0.000 claims description 2
- JWNMLWPGXCYXLI-UHFFFAOYSA-N 5-(pyridin-3-ylmethyl)-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC2=NNC=C2C(=O)N1CC1=CC=CN=C1 JWNMLWPGXCYXLI-UHFFFAOYSA-N 0.000 claims description 2
- XINOYZZCYJVHAI-UHFFFAOYSA-N 5-(pyridin-4-ylmethyl)-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC2=NNC=C2C(=O)N1CC1=CC=NC=C1 XINOYZZCYJVHAI-UHFFFAOYSA-N 0.000 claims description 2
- QNYVUEWYUZKLIR-UHFFFAOYSA-N 5-[(2,4,6-trimethylphenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC(C)=CC(C)=C1CN1C(=O)C2=CNN=C2N=C1 QNYVUEWYUZKLIR-UHFFFAOYSA-N 0.000 claims description 2
- SICHJHQFAKVBKW-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC(Cl)=CC=C1CN1C(=O)C2=CNN=C2N=C1 SICHJHQFAKVBKW-UHFFFAOYSA-N 0.000 claims description 2
- NWNSBEOJBJQELV-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C=C1Cl NWNSBEOJBJQELV-UHFFFAOYSA-N 0.000 claims description 2
- QEQZIJYLCYDSEY-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=C(Cl)C=CC=C1Cl QEQZIJYLCYDSEY-UHFFFAOYSA-N 0.000 claims description 2
- CRPNJOQSDJZOJZ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(F)=C1CN1C(=O)C2=CNN=C2N=C1 CRPNJOQSDJZOJZ-UHFFFAOYSA-N 0.000 claims description 2
- XRVREQKBLREZSK-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-2,6-dimethylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=NN(C)C=C2C(=O)N1CC1=C(F)C=CC=C1F XRVREQKBLREZSK-UHFFFAOYSA-N 0.000 claims description 2
- CGZHZRXOEAEINF-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-2-(pyridin-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(F)=C1CN1C(=O)C2=CN(CC=3N=CC=CC=3)N=C2N=C1 CGZHZRXOEAEINF-UHFFFAOYSA-N 0.000 claims description 2
- NSPYEGLHZGCGBZ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-2-ethylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CC)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1F NSPYEGLHZGCGBZ-UHFFFAOYSA-N 0.000 claims description 2
- PZECXTOQFHTQGG-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1F PZECXTOQFHTQGG-UHFFFAOYSA-N 0.000 claims description 2
- QQMKAIDOVGURLP-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-2-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(F)=C1CN1C(=O)C2=CN(C=3C=CC=CC=3)N=C2N=C1 QQMKAIDOVGURLP-UHFFFAOYSA-N 0.000 claims description 2
- TTYRJAIPAMKAMB-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-2-propan-2-ylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C(C)C)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1F TTYRJAIPAMKAMB-UHFFFAOYSA-N 0.000 claims description 2
- CWTAITURROZLHW-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-2-propylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CCC)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1F CWTAITURROZLHW-UHFFFAOYSA-N 0.000 claims description 2
- YWFMREGPHUYEDV-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methyl]-6-methyl-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=NNC=C2C(=O)N1CC1=C(F)C=CC=C1F YWFMREGPHUYEDV-UHFFFAOYSA-N 0.000 claims description 2
- DRHFWRPPGZQMBW-UHFFFAOYSA-N 5-[(2-chloro-6-fluorophenyl)methyl]-2-ethylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CC)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1Cl DRHFWRPPGZQMBW-UHFFFAOYSA-N 0.000 claims description 2
- ADFTXDJWLDNODQ-UHFFFAOYSA-N 5-[(2-chloro-6-fluorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1Cl ADFTXDJWLDNODQ-UHFFFAOYSA-N 0.000 claims description 2
- JTMWHJOJHIAEPF-UHFFFAOYSA-N 5-[(2-chloro-6-fluorophenyl)methyl]-2-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(Cl)=C1CN1C(=O)C2=CN(C=3C=CC=CC=3)N=C2N=C1 JTMWHJOJHIAEPF-UHFFFAOYSA-N 0.000 claims description 2
- VNVIZFKRIWSZNQ-UHFFFAOYSA-N 5-[(2-chloro-6-fluorophenyl)methyl]-2-propan-2-ylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C(C)C)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1Cl VNVIZFKRIWSZNQ-UHFFFAOYSA-N 0.000 claims description 2
- HJFPDZQDSAWCRK-UHFFFAOYSA-N 5-[(2-chloro-6-fluorophenyl)methyl]-2-propylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CCC)C=C(C2=O)C=1N=CN2CC1=C(F)C=CC=C1Cl HJFPDZQDSAWCRK-UHFFFAOYSA-N 0.000 claims description 2
- KMRGXJWVFHNMSQ-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=C1Cl KMRGXJWVFHNMSQ-UHFFFAOYSA-N 0.000 claims description 2
- CFARRBFGZHWBSW-UHFFFAOYSA-N 5-[(2-iodophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=C1I CFARRBFGZHWBSW-UHFFFAOYSA-N 0.000 claims description 2
- FWXXCWYDEOBULT-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1CN1C(=O)C2=CNN=C2N=C1 FWXXCWYDEOBULT-UHFFFAOYSA-N 0.000 claims description 2
- HLISVYKYHKEOQW-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1CN1C(=O)C2=CN(C)N=C2N=C1 HLISVYKYHKEOQW-UHFFFAOYSA-N 0.000 claims description 2
- DCGCRXMPVSXOJY-UHFFFAOYSA-N 5-[(2-methylphenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=CC=CC=C1CN1C(=O)C2=CNN=C2N=C1 DCGCRXMPVSXOJY-UHFFFAOYSA-N 0.000 claims description 2
- FGYHLTKHSYGQMJ-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC(Cl)=C1 FGYHLTKHSYGQMJ-UHFFFAOYSA-N 0.000 claims description 2
- WYYUYPJVUXFPPM-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C2=CNN=C2N=C1 WYYUYPJVUXFPPM-UHFFFAOYSA-N 0.000 claims description 2
- XMCDIPCCKOAIGJ-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C=C1 XMCDIPCCKOAIGJ-UHFFFAOYSA-N 0.000 claims description 2
- FKBKIVNNAZQFJJ-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(F)=CC=C1CN1C(=O)C2=CNN=C2N=C1 FKBKIVNNAZQFJJ-UHFFFAOYSA-N 0.000 claims description 2
- QKIHDGHCVXBFAQ-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=C(F)C=C1 QKIHDGHCVXBFAQ-UHFFFAOYSA-N 0.000 claims description 2
- QPFNXNKOHWYGCQ-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-2-phenylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C2=CN(C=3C=CC=CC=3)N=C2N=C1 QPFNXNKOHWYGCQ-UHFFFAOYSA-N 0.000 claims description 2
- VJKPHMHEDAHJLB-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-2-propan-2-ylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C(C)C)C=C(C2=O)C=1N=CN2CC1=CC=C(C)C=C1 VJKPHMHEDAHJLB-UHFFFAOYSA-N 0.000 claims description 2
- XDHXOGLSOZJJMC-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-2-propylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(CCC)C=C(C2=O)C=1N=CN2CC1=CC=C(C)C=C1 XDHXOGLSOZJJMC-UHFFFAOYSA-N 0.000 claims description 2
- MUHJBDDCEXIXHK-UHFFFAOYSA-N 5-[[2-(trifluoromethyl)phenyl]methyl]-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC(F)(F)C1=CC=CC=C1CN1C(=O)C2=CNN=C2N=C1 MUHJBDDCEXIXHK-UHFFFAOYSA-N 0.000 claims description 2
- MRGMAASWWFCZMM-UHFFFAOYSA-N 5-benzyl-2-methylpyrazolo[3,4-d]pyrimidin-4-one Chemical compound N=1N(C)C=C(C2=O)C=1N=CN2CC1=CC=CC=C1 MRGMAASWWFCZMM-UHFFFAOYSA-N 0.000 claims description 2
- MAYUCBCSAVDUKG-UHFFFAOYSA-N orthoacetic acid Chemical class CC(O)(O)O MAYUCBCSAVDUKG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 4
- KOPLPJUAZXSGGH-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-2-(oxolan-2-ylmethyl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound ClC1=CC=CC=C1CN1C(=O)C2=CN(CC3OCCC3)N=C2N=C1 KOPLPJUAZXSGGH-UHFFFAOYSA-N 0.000 claims 1
- QZOHLMMPYFVKJL-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-6-methyl-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound CC1=NC2=NNC=C2C(=O)N1CC1=CC=CC=C1Cl QZOHLMMPYFVKJL-UHFFFAOYSA-N 0.000 claims 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000001961 anticonvulsive agent Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229960003965 antiepileptics Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- LEFSNWUSTYESGC-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carboxamide Chemical compound NC(=O)C1=CNN=C1N LEFSNWUSTYESGC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical class C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 2
- JZPHAJFIZZEAEK-UHFFFAOYSA-N 3-chloro-6-methoxy-2h-indazole Chemical compound COC1=CC=C2C(Cl)=NNC2=C1 JZPHAJFIZZEAEK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 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 description 2
- 206010029350 Neurotoxicity Diseases 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- 206010044221 Toxic encephalopathy Diseases 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 230000007135 neurotoxicity Effects 0.000 description 2
- 231100000228 neurotoxicity Toxicity 0.000 description 2
- -1 pyrazolopyramides Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 description 1
- STLFDTKIWQNYHR-UHFFFAOYSA-N 2-benzyl-5-[(2,6-difluorophenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(F)=C1CN1C(=O)C2=CN(CC=3C=CC=CC=3)N=C2N=C1 STLFDTKIWQNYHR-UHFFFAOYSA-N 0.000 description 1
- RMABPCNSXXKDLU-UHFFFAOYSA-N 2-benzyl-5-[(4-methylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)C2=CN(CC=3C=CC=CC=3)N=C2N=C1 RMABPCNSXXKDLU-UHFFFAOYSA-N 0.000 description 1
- GIZUAZUUKUGDLI-UHFFFAOYSA-N 5-(2-phenylethyl)-1h-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=NC=2NN=CC=2C(=O)N1CCC1=CC=CC=C1 GIZUAZUUKUGDLI-UHFFFAOYSA-N 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LHNKBXRFNPMIBR-UHFFFAOYSA-N Picrotoxin Natural products CC(C)(O)C1(O)C2OC(=O)C1C3(O)C4OC4C5C(=O)OC2C35C LHNKBXRFNPMIBR-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FJWLWIRHZOHPIY-UHFFFAOYSA-N potassium;hydroiodide Chemical compound [K].I FJWLWIRHZOHPIY-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10042092A DE10042092A1 (de) | 2000-08-26 | 2000-08-26 | Antikonvulsiv wirkende 2,5-Dihydro-pyrazolo(3,4-d)pyrimidin-4-one und Verfahren zu deren Darstellung |
| PCT/EP2001/009811 WO2002018387A1 (de) | 2000-08-26 | 2001-08-24 | Antikonvulsiv wirkende 2,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one und verfahren zu deren darstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20030226A2 true HRP20030226A2 (en) | 2003-06-30 |
Family
ID=7653967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20030226A HRP20030226A2 (en) | 2000-08-26 | 2003-03-24 | 2,5-DIHYDRO-PYRAZOLO[3,4-d]PYRIMIDIN-4-ONES WITH AN ANTICONVULSIVE ACTION AND METHODS FOR PRODUCING THE SAME |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20030186997A1 (ja) |
| EP (1) | EP1311510A1 (ja) |
| JP (1) | JP2004507547A (ja) |
| KR (1) | KR20030036734A (ja) |
| CN (1) | CN1449397A (ja) |
| AU (1) | AU2001282124A1 (ja) |
| BG (1) | BG107561A (ja) |
| BR (1) | BR0113517A (ja) |
| CA (1) | CA2420288A1 (ja) |
| DE (1) | DE10042092A1 (ja) |
| EE (1) | EE200300078A (ja) |
| HR (1) | HRP20030226A2 (ja) |
| IL (1) | IL154070A0 (ja) |
| NO (1) | NO20030687D0 (ja) |
| RU (1) | RU2003108258A (ja) |
| WO (1) | WO2002018387A1 (ja) |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3165520A (en) * | 1965-01-12 | Certificate of correction | ||
| US3939161A (en) * | 1973-10-29 | 1976-02-17 | Abbott Laboratories | 1,3-Dimethyl- 1H-pyrazolo(4,3-D) pyrimidine-7 (6H)-ones |
| US5721356A (en) * | 1989-09-15 | 1998-02-24 | Gensia, Inc. | Orally active adenosine kinase inhibitors |
| US5763596A (en) * | 1989-09-15 | 1998-06-09 | Metabasis Therapeutics, Inc. | C-4' modified adenosine kinase inhibitors |
| EP0729758A3 (en) * | 1995-03-02 | 1997-10-29 | Pfizer | Pyrazolopyrimidines and pyrrolopyrimidines to treat neuronal disorders and other diseases |
| DE19827679A1 (de) * | 1998-06-22 | 1999-12-23 | Dresden Arzneimittel | Adenosinrezeptoraffine, antikonvulsiv und antiallergisch/antiasthmatisch wirkende Pyrazolo[3,4-d]pyrimidine und Verfahren zu deren Herstellung |
-
2000
- 2000-08-26 DE DE10042092A patent/DE10042092A1/de not_active Withdrawn
-
2001
- 2001-08-24 CA CA002420288A patent/CA2420288A1/en not_active Abandoned
- 2001-08-24 EE EEP200300078A patent/EE200300078A/xx unknown
- 2001-08-24 KR KR10-2003-7002753A patent/KR20030036734A/ko not_active Application Discontinuation
- 2001-08-24 AU AU2001282124A patent/AU2001282124A1/en not_active Abandoned
- 2001-08-24 WO PCT/EP2001/009811 patent/WO2002018387A1/de not_active Application Discontinuation
- 2001-08-24 US US10/333,504 patent/US20030186997A1/en not_active Abandoned
- 2001-08-24 JP JP2002523902A patent/JP2004507547A/ja active Pending
- 2001-08-24 RU RU2003108258/04A patent/RU2003108258A/ru not_active Application Discontinuation
- 2001-08-24 BR BR0113517-1A patent/BR0113517A/pt not_active Application Discontinuation
- 2001-08-24 IL IL15407001A patent/IL154070A0/xx unknown
- 2001-08-24 EP EP01960709A patent/EP1311510A1/de not_active Withdrawn
- 2001-08-24 CN CN01814655A patent/CN1449397A/zh active Pending
-
2003
- 2003-02-12 NO NO20030687A patent/NO20030687D0/no unknown
- 2003-02-14 BG BG107561A patent/BG107561A/xx unknown
- 2003-03-24 HR HR20030226A patent/HRP20030226A2/hr not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE10042092A1 (de) | 2002-03-07 |
| EE200300078A (et) | 2004-12-15 |
| EP1311510A1 (de) | 2003-05-21 |
| WO2002018387A1 (de) | 2002-03-07 |
| BR0113517A (pt) | 2003-07-29 |
| US20030186997A1 (en) | 2003-10-02 |
| BG107561A (en) | 2003-10-31 |
| JP2004507547A (ja) | 2004-03-11 |
| RU2003108258A (ru) | 2005-01-27 |
| CA2420288A1 (en) | 2002-03-07 |
| NO20030687L (no) | 2003-02-12 |
| IL154070A0 (en) | 2003-07-31 |
| CN1449397A (zh) | 2003-10-15 |
| NO20030687D0 (no) | 2003-02-12 |
| KR20030036734A (ko) | 2003-05-09 |
| AU2001282124A1 (en) | 2002-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| OBST | Application withdrawn |