JPS6254315B2 - - Google Patents
Info
- Publication number
- JPS6254315B2 JPS6254315B2 JP54127271A JP12727179A JPS6254315B2 JP S6254315 B2 JPS6254315 B2 JP S6254315B2 JP 54127271 A JP54127271 A JP 54127271A JP 12727179 A JP12727179 A JP 12727179A JP S6254315 B2 JPS6254315 B2 JP S6254315B2
- Authority
- JP
- Japan
- Prior art keywords
- deoxy
- arabinofuranosyl
- acetyl
- fluoro
- bromo
- 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.)
- Expired
Links
- -1 methyl-6-azacytosine hydrochloride Chemical compound 0.000 claims description 64
- 239000002777 nucleoside Substances 0.000 claims description 41
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- GIMSJJHKKXRFGV-BYPJNBLXSA-N 4-amino-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one Chemical compound C1=C(I)C(N)=NC(=O)N1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 GIMSJJHKKXRFGV-BYPJNBLXSA-N 0.000 claims description 14
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
- 229920002554 vinyl polymer Polymers 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003435 aroyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 230000001093 anti-cancer Effects 0.000 claims description 5
- 230000000840 anti-viral effect Effects 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 229960002949 fluorouracil Drugs 0.000 claims description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000002718 pyrimidine nucleoside Substances 0.000 claims description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229960004413 flucytosine Drugs 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 229940113082 thymine Drugs 0.000 claims description 4
- QURNODSOJKSTBM-BYPJNBLXSA-N 5-fluoro-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound F[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 QURNODSOJKSTBM-BYPJNBLXSA-N 0.000 claims description 3
- NMTPBDDUXMBDJY-HLPPOEQASA-N [(2r,3r,4s,5r)-3-acetyloxy-5-(4-amino-5-bromo-2-oxopyrimidin-1-yl)-4-fluorooxolan-2-yl]methyl benzoate Chemical compound C([C@@H]1[C@H]([C@@H]([C@@H](O1)N1C(N=C(N)C(Br)=C1)=O)F)OC(=O)C)OC(=O)C1=CC=CC=C1 NMTPBDDUXMBDJY-HLPPOEQASA-N 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- JRJDWZLXLRAIBF-BYPJNBLXSA-N 1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound Br[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 JRJDWZLXLRAIBF-BYPJNBLXSA-N 0.000 claims description 2
- GBBJCSTXCAQSSJ-JVZYCSMKSA-N 1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 GBBJCSTXCAQSSJ-JVZYCSMKSA-N 0.000 claims description 2
- OWKKCDYEWVMPII-MFHVBSIWSA-N 4-amino-1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(I)C(N)=NC(=O)N1[C@H]1[C@@H](Br)[C@H](O)[C@@H](CO)O1 OWKKCDYEWVMPII-MFHVBSIWSA-N 0.000 claims description 2
- RIWZLENSSBQYGJ-MFHVBSIWSA-N 4-amino-1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(I)C(N)=NC(=O)N1[C@H]1[C@@H](Cl)[C@H](O)[C@@H](CO)O1 RIWZLENSSBQYGJ-MFHVBSIWSA-N 0.000 claims description 2
- AEEIHBCRILUCMM-BYPJNBLXSA-N 5-bromo-1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound Br[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 AEEIHBCRILUCMM-BYPJNBLXSA-N 0.000 claims description 2
- XMJADGYTDLLSPU-HLPPOEQASA-N [(2r,3r,4s,5r)-3-acetyloxy-4-fluoro-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate Chemical compound C([C@@H]1[C@H]([C@@H]([C@@H](O1)N1C(NC(=O)C(F)=C1)=O)F)OC(=O)C)OC(=O)C1=CC=CC=C1 XMJADGYTDLLSPU-HLPPOEQASA-N 0.000 claims description 2
- RHYNQIVFSMCOPW-HLPPOEQASA-N [(2r,3r,4s,5r)-3-acetyloxy-5-(4-amino-5-chloro-2-oxopyrimidin-1-yl)-4-fluorooxolan-2-yl]methyl benzoate Chemical compound C([C@@H]1[C@H]([C@@H]([C@@H](O1)N1C(N=C(N)C(Cl)=C1)=O)F)OC(=O)C)OC(=O)C1=CC=CC=C1 RHYNQIVFSMCOPW-HLPPOEQASA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- NEJVFDJYSZDPCD-BYPJNBLXSA-N 5-chloro-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound F[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Cl)=C1 NEJVFDJYSZDPCD-BYPJNBLXSA-N 0.000 claims 2
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims 2
- VDBLGGVAKLODST-BYPJNBLXSA-N 1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-chloropyrimidine-2,4-dione Chemical compound Br[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Cl)=C1 VDBLGGVAKLODST-BYPJNBLXSA-N 0.000 claims 1
- UJPBYLWDTABZDC-BYPJNBLXSA-N 1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione Chemical compound Br[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 UJPBYLWDTABZDC-BYPJNBLXSA-N 0.000 claims 1
- UTMUIPQCQMEAEI-JVZYCSMKSA-N 1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1[C@@H](Br)[C@H](O)[C@@H](CO)O1 UTMUIPQCQMEAEI-JVZYCSMKSA-N 0.000 claims 1
- MJRDOWMCKVHWFT-BYPJNBLXSA-N 1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidine-2,4-dione Chemical compound Cl[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 MJRDOWMCKVHWFT-BYPJNBLXSA-N 0.000 claims 1
- OCKSZBNSFFQFNQ-BYPJNBLXSA-N 1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound Cl[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 OCKSZBNSFFQFNQ-BYPJNBLXSA-N 0.000 claims 1
- WQMQACLYZYXSDZ-JVZYCSMKSA-N 1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1[C@@H](Cl)[C@H](O)[C@@H](CO)O1 WQMQACLYZYXSDZ-JVZYCSMKSA-N 0.000 claims 1
- VINXNBONGBUEPN-BYPJNBLXSA-N 4,5-diamino-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C(N)=CN1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 VINXNBONGBUEPN-BYPJNBLXSA-N 0.000 claims 1
- PTKHTHKPGHMPAS-MFHVBSIWSA-N 4-amino-1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-chloropyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=NC(=O)N1[C@H]1[C@@H](Br)[C@H](O)[C@@H](CO)O1 PTKHTHKPGHMPAS-MFHVBSIWSA-N 0.000 claims 1
- SKGVXZUZIRWCPT-MFHVBSIWSA-N 4-amino-1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(F)C(N)=NC(=O)N1[C@H]1[C@@H](Br)[C@H](O)[C@@H](CO)O1 SKGVXZUZIRWCPT-MFHVBSIWSA-N 0.000 claims 1
- AZVBVHYZSKSPKM-BFFMJPLYSA-N 4-amino-1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidin-2-one;hydrochloride Chemical compound Cl.O=C1N=C(N)C(C)=CN1[C@H]1[C@@H](Br)[C@H](O)[C@@H](CO)O1 AZVBVHYZSKSPKM-BFFMJPLYSA-N 0.000 claims 1
- IMZHVLIVDCRXSX-MFHVBSIWSA-N 4-amino-1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(F)C(N)=NC(=O)N1[C@H]1[C@@H](Cl)[C@H](O)[C@@H](CO)O1 IMZHVLIVDCRXSX-MFHVBSIWSA-N 0.000 claims 1
- LLYQYRHWIHEUQL-JVZYCSMKSA-N 4-amino-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)pyrimidin-2-one Chemical compound C1=C(CO)C(N)=NC(=O)N1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 LLYQYRHWIHEUQL-JVZYCSMKSA-N 0.000 claims 1
- OUUDGZZYJIHGIY-GFQSEFKGSA-N 4-amino-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-phenylpyrimidin-2-one Chemical compound NC1=NC(=O)N([C@H]2[C@H]([C@H](O)[C@@H](CO)O2)F)C=C1C1=CC=CC=C1 OUUDGZZYJIHGIY-GFQSEFKGSA-N 0.000 claims 1
- JLBSFFJDODOKDC-JVZYCSMKSA-N 4-amino-5-(aminomethyl)-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C(CN)=CN1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 JLBSFFJDODOKDC-JVZYCSMKSA-N 0.000 claims 1
- XKQURBTUDPOFCK-QVHKTLOISA-N 4-amino-5-(benzylamino)-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound NC1=NC(=O)N([C@H]2[C@H]([C@H](O)[C@@H](CO)O2)F)C=C1NCC1=CC=CC=C1 XKQURBTUDPOFCK-QVHKTLOISA-N 0.000 claims 1
- CVQLOWRAJYUCGG-QVHKTLOISA-N 4-amino-5-benzyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound NC1=NC(=O)N([C@H]2[C@H]([C@H](O)[C@@H](CO)O2)F)C=C1CC1=CC=CC=C1 CVQLOWRAJYUCGG-QVHKTLOISA-N 0.000 claims 1
- QIWHJDOICMHZMH-MFHVBSIWSA-N 4-amino-5-bromo-1-[(2r,3s,4r,5r)-3-bromo-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(Br)C(N)=NC(=O)N1[C@H]1[C@@H](Br)[C@H](O)[C@@H](CO)O1 QIWHJDOICMHZMH-MFHVBSIWSA-N 0.000 claims 1
- NMTIVRMZURHSLU-MFHVBSIWSA-N 4-amino-5-bromo-1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(Br)C(N)=NC(=O)N1[C@H]1[C@@H](Cl)[C@H](O)[C@@H](CO)O1 NMTIVRMZURHSLU-MFHVBSIWSA-N 0.000 claims 1
- DPTQLSGNVUCAMZ-BYPJNBLXSA-N 4-amino-5-bromo-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(Br)C(N)=NC(=O)N1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 DPTQLSGNVUCAMZ-BYPJNBLXSA-N 0.000 claims 1
- OCQJAHDUKQSEMU-MFHVBSIWSA-N 4-amino-5-chloro-1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=NC(=O)N1[C@H]1[C@@H](Cl)[C@H](O)[C@@H](CO)O1 OCQJAHDUKQSEMU-MFHVBSIWSA-N 0.000 claims 1
- JGMINUKHOITSQF-IBCQBUCCSA-N 4-amino-5-ethenyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(C=C)C(N)=NC(=O)N1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 JGMINUKHOITSQF-IBCQBUCCSA-N 0.000 claims 1
- QBSJDBXQJJKDOI-IBCQBUCCSA-N 4-amino-5-ethyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C(CC)=CN1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 QBSJDBXQJJKDOI-IBCQBUCCSA-N 0.000 claims 1
- NJJYCPXWFZQVEP-IBCQBUCCSA-N 4-amino-5-ethynyl-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(C#C)C(N)=NC(=O)N1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 NJJYCPXWFZQVEP-IBCQBUCCSA-N 0.000 claims 1
- MNKROXHDFKZYHJ-MFHVBSIWSA-N 5-amino-2-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-1,2,4-triazin-3-one;hydrochloride Chemical compound Cl.O=C1N=C(N)C(C)=NN1[C@H]1[C@@H](Cl)[C@H](O)[C@@H](CO)O1 MNKROXHDFKZYHJ-MFHVBSIWSA-N 0.000 claims 1
- YCSLQJPNMRWEAL-BYPJNBLXSA-N 5-amino-2-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-1,2,4-triazin-3-one Chemical compound O=C1N=C(N)C(C)=NN1[C@H]1[C@@H](F)[C@H](O)[C@@H](CO)O1 YCSLQJPNMRWEAL-BYPJNBLXSA-N 0.000 claims 1
- RTWLWBAJWOUKKC-BYPJNBLXSA-N 5-bromo-1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound Cl[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 RTWLWBAJWOUKKC-BYPJNBLXSA-N 0.000 claims 1
- WFOXFPXBLFRFHB-BYPJNBLXSA-N 5-bromo-1-[(2r,3s,4r,5r)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound F[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WFOXFPXBLFRFHB-BYPJNBLXSA-N 0.000 claims 1
- XKFSDLVRRRHPKP-BYPJNBLXSA-N 5-chloro-1-[(2r,3s,4r,5r)-3-chloro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound Cl[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Cl)=C1 XKFSDLVRRRHPKP-BYPJNBLXSA-N 0.000 claims 1
- WTJIUBLHXMPWCE-ZZDJIJSSSA-N 6-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodo-1H-pyrimidine-2,4-dione Chemical compound C1([C@@H](O)[C@H](O)[C@H](O1)CO)C1=C(C(NC(N1)=O)=O)I WTJIUBLHXMPWCE-ZZDJIJSSSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 19
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 229910052794 bromium Inorganic materials 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical class NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
- 229940035893 uracil Drugs 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/12—Triazine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/948,189 US4211773A (en) | 1978-10-02 | 1978-10-02 | 5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5549395A JPS5549395A (en) | 1980-04-09 |
| JPS6254315B2 true JPS6254315B2 (online.php) | 1987-11-13 |
Family
ID=25487441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12727179A Granted JPS5549395A (en) | 1978-10-02 | 1979-10-02 | 55substituted 11*2**deoxyy2**substitutedd betaaddarabinofuranosyl*pyrimidinenucleoside |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4211773A (online.php) |
| EP (1) | EP0010205B1 (online.php) |
| JP (1) | JPS5549395A (online.php) |
| AU (1) | AU533135B2 (online.php) |
| CA (1) | CA1131626A (online.php) |
| DE (1) | DE2965318D1 (online.php) |
| ES (1) | ES484626A1 (online.php) |
| HU (1) | HU182597B (online.php) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11061285B2 (en) | 2006-05-16 | 2021-07-13 | Semiconductor Energy Laboratory Co., Ltd. | Liquid crystal display device comprising a dogleg-like shaped pixel electrode in a plane view having a plurality of dogleg-like shaped openings and semiconductor device |
Families Citing this family (74)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4418059A (en) * | 1981-07-20 | 1983-11-29 | Montefiore Medical Center | Nucleoside ester compositions |
| US4594339A (en) * | 1982-04-06 | 1986-06-10 | Sloan-Kettering Institute For Cancer Research | Anti-herpes virus compositions containing 5-substituted 1-2'(deoxy-2-'-substituted-β-d-arabinofuranosyl)pyrimedene nucleosides |
| JPS58225097A (ja) * | 1982-06-23 | 1983-12-27 | Yamasa Shoyu Co Ltd | ヌクレオシド５′−アルキルもしくはアルケニルりん酸 |
| US4526988A (en) * | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| US4625020A (en) * | 1983-11-18 | 1986-11-25 | Bristol-Myers Company | Nucleoside process |
| US4666892A (en) * | 1984-03-06 | 1987-05-19 | Sloan-Kettering Memorial Cancer Center | Method and composition for hepatitis treatment with pyrimidine nucleoside compounds |
| ZA859008B (en) * | 1984-12-04 | 1987-07-29 | Lilly Co Eli | The treatment of tumors in mammals |
| DE3587500T2 (de) * | 1984-12-04 | 1993-12-16 | Lilly Co Eli | Tumorbehandlung bei Säugetieren. |
| JPS61204193A (ja) * | 1985-03-05 | 1986-09-10 | Takeda Chem Ind Ltd | シトシンヌクレオシド類の製造法 |
| CA1295998C (en) * | 1985-07-29 | 1992-02-18 | Sai P. Sunkara | Nucleosides and their use as antineoplastic agents |
| NO170884C (no) * | 1986-08-18 | 1992-12-23 | Hoffmann La Roche | Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyrimidinderivater |
| GB8629892D0 (en) * | 1986-12-15 | 1987-01-28 | Wellcome Found | Antiviral compounds |
| DE3851889T2 (de) * | 1987-06-24 | 1995-04-13 | Florey Howard Inst | Nukleosid-derivate. |
| EP0333832B1 (en) * | 1987-09-22 | 1992-06-03 | Temple University | Artificial dna base pair analogues |
| US4908440A (en) * | 1987-11-12 | 1990-03-13 | Bristol Myers Company | 2',3'-dideoxy-2'-fluoroarabinopyrimidine nucleosides |
| EP0346108A3 (en) * | 1988-06-09 | 1991-04-24 | The Wellcome Foundation Limited | Anti-infective nucleosides |
| SE8802173D0 (sv) * | 1988-06-10 | 1988-06-10 | Astra Ab | Pyrimidine derivatives |
| GB8827339D0 (en) * | 1988-11-23 | 1988-12-29 | Wellcome Found | Antiviral compounds |
| US5006646A (en) * | 1989-02-22 | 1991-04-09 | Yuki Gosei Kogyo Co., Ltd. | Process for preparing 2'-deoxy-5-trifluoromethyl-beta-uridine |
| FI95384C (fi) * | 1989-04-06 | 1996-01-25 | Squibb Bristol Myers Co | Menetelmä 3'-deoksi-3'-substituoitujen metyylinukleosidien valmistamiseksi ja menetelmässä käytettäviä välituotteita |
| US6258360B1 (en) * | 1989-05-04 | 2001-07-10 | Igen International, Inc. | Prodrugs activated by targeted catalytic proteins |
| GB8912972D0 (en) * | 1989-06-06 | 1989-07-26 | Wellcome Found | Therapeutic nucleosides |
| IE902574A1 (en) * | 1989-07-17 | 1991-02-27 | Univ Birmingham | Antiviral pyrimidine nucleosides |
| US5134066A (en) * | 1989-08-29 | 1992-07-28 | Monsanto Company | Improved probes using nucleosides containing 3-dezauracil analogs |
| US5200514A (en) * | 1990-01-19 | 1993-04-06 | University Of Georgia Research Foundation, Inc. | Synthesis of 2'-deoxypyrimidine nucleosides |
| US5352584A (en) * | 1990-01-22 | 1994-10-04 | E. R. Squibb & Sons, Inc. | Monoclonal antibodies which bind (E)-5- (2-bromovinyl)-arabinofuranosyluracil and diagnostic methods based thereon |
| GB9009861D0 (en) * | 1990-05-02 | 1990-06-27 | Glaxo Group Ltd | Chemical compounds |
| US5817799A (en) * | 1990-07-23 | 1998-10-06 | The United States Of America As Represented By The Department Of Health And Human Services | 2'-Fluorofuranosyl derivatives and methods for preparing 2'-fluoropyrimidine and 2'-fluoropurine nucleosides |
| DE69208636T2 (de) * | 1991-06-21 | 1996-07-11 | Acic Canada Inc | Verfahren zur herstellung von zidovudine |
| US5248771A (en) * | 1991-06-26 | 1993-09-28 | Triumf | Process for preparing no-carrier-added radiohalogenated vinyl nucleosides |
| RU2085557C1 (ru) * | 1991-09-30 | 1997-07-27 | Санкио Компани Лимитед | Производные нуклеозидов пиримидина или их фармацевтически приемлемые соли и способ их получения |
| GB2260319B (en) * | 1991-10-07 | 1995-12-06 | Norsk Hydro As | Acyl derivatives of nucleosides and nucleoside analogues having anti-viral activity |
| HU207524B (en) * | 1991-11-22 | 1993-04-28 | Mta Koezponti Kemiai Kutato In | Industrial process for producing 5-alkyl-2'-deoxy-beta-uridines with stereoselective synthesis |
| FR2688003B1 (fr) * | 1992-02-28 | 1995-06-30 | Univ Limoges | Derives de nucleosides, leur preparation et leurs applications biologiques. |
| US5432165A (en) * | 1992-04-06 | 1995-07-11 | Oclassen Pharmaceuticals, Inc. | Methods for the treatment of infection caused by Hepatitis B virus (HBV) |
| US5401838A (en) * | 1992-06-22 | 1995-03-28 | Eli Lilly And Company | Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| US5821357A (en) * | 1992-06-22 | 1998-10-13 | Eli Lilly And Company | Stereoselective glycosylation process for preparing 2'-deoxy-2',2'-difluoropurine and triazole nucleosides |
| US5606048A (en) * | 1992-06-22 | 1997-02-25 | Eli Lilly And Company | Stereoselective glycosylation process for preparing 2'-Deoxy-2', 2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| US5594124A (en) * | 1992-06-22 | 1997-01-14 | Eli Lilly And Company | Stereoselective glycosylation process for preparing 2'-Deoxy-2',2'-difluoropyrimidine nucleosides and 2'-deoxy-2'-fluoropyrimidine nucleosides and intermediates thereof |
| US5426183A (en) * | 1992-06-22 | 1995-06-20 | Eli Lilly And Company | Catalytic stereoselective glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| ES2101231T3 (es) * | 1992-06-22 | 1997-07-01 | Lilly Co Eli | Procedimiento estereoselectivo de glicosilacion de anion. |
| US5371210A (en) * | 1992-06-22 | 1994-12-06 | Eli Lilly And Company | Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| US6040298A (en) * | 1992-12-23 | 2000-03-21 | Oclassen Pharmaceuticals, Inc. | Methods for treatment with compositions effective against acyclovir-resistant strains of herpes viruses |
| US5424416A (en) * | 1993-08-25 | 1995-06-13 | Eli Lilly And Company | Process for preparation of 2-deoxy-2,2-difluoro-D-ribofuranosyl-3,5-hydroxy protected-1-alkyl and aryl sulfonates and their use in preparation of 2',2'-difluoro-2'-deoxy nucleosides |
| US5811073A (en) * | 1995-06-19 | 1998-09-22 | President And Fellows Of Harvard College | Method for radioisotopic detection and localization of inflammation in a host |
| US6331287B1 (en) * | 1995-08-23 | 2001-12-18 | University Advanced Bio-Imaging Associates | 2′-deoxy-2′-fluoro-d-arabinofuranosyl pyrimidine nucleoside |
| US6001994A (en) * | 1995-12-13 | 1999-12-14 | Eli Lilly And Company | Process for making gemcitabine hydrochloride |
| US5756775A (en) * | 1995-12-13 | 1998-05-26 | Eli Lilly And Company | Process to make α,α-difluoro-β-hydroxyl thiol esters |
| JP4352115B2 (ja) * | 1997-01-24 | 2009-10-28 | クラヴィス・ファルマ・アーエスアー | ゲムシタビン誘導体 |
| EP1058686B1 (en) * | 1998-02-25 | 2006-11-02 | Emory University | 2'-fluoronucleosides |
| JP2004533406A (ja) | 2000-10-18 | 2004-11-04 | フアーマセツト・リミテツド | ウイルス感染症および異常細胞増殖を治療するための修飾ヌクレオシド |
| US8481712B2 (en) | 2001-01-22 | 2013-07-09 | Merck Sharp & Dohme Corp. | Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase |
| US6949522B2 (en) | 2001-06-22 | 2005-09-27 | Pharmasset, Inc. | β-2′- or 3′-halonucleosides |
| AU2003278904A1 (en) * | 2002-09-24 | 2004-04-19 | Kornis Pharmaceuticals, Incorporated | 1, 3, 5-triazines for treatment of viral diseases |
| US8895531B2 (en) * | 2006-03-23 | 2014-11-25 | Rfs Pharma Llc | 2′-fluoronucleoside phosphonates as antiviral agents |
| US20090274686A1 (en) * | 2008-05-02 | 2009-11-05 | Yat Sun Or | Nucleoside phosphonate derivatives |
| US9011817B2 (en) * | 2009-09-03 | 2015-04-21 | The Board Of Trustees Of The Leland Stanford Junior University | Compounds and methods of making compounds |
| JP2014511875A (ja) | 2011-04-13 | 2014-05-19 | メルク・シャープ・アンド・ドーム・コーポレーション | ２’−シアノ置換ヌクレオシド誘導体およびウイルス疾患の治療のためのその使用方法 |
| US9156872B2 (en) | 2011-04-13 | 2015-10-13 | Merck Sharp & Dohme Corp. | 2′-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| EP2696681B1 (en) | 2011-04-13 | 2018-10-03 | Merck Sharp & Dohme Corp. | 2'-substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| US9416154B2 (en) | 2011-07-13 | 2016-08-16 | Merck Sharp & Dohme Corp. | 5′-substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases |
| WO2013009737A1 (en) | 2011-07-13 | 2013-01-17 | Merck Sharp & Dohme Corp. | 5'-substituted nucleoside analogs and methods of use thereof for the treatment of viral diseases |
| SG10201610936RA (en) | 2011-12-22 | 2017-02-27 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| SG10201603288XA (en) * | 2012-03-28 | 2016-05-30 | Fujifilm Corp | Salt Of 1-(2-Deoxy-2-Fluoro-4-Thio-beta-D-Arabinofuranosyl)Cytosine |
| KR20170001722A (ko) | 2012-08-13 | 2017-01-04 | 후지필름 가부시키가이샤 | 1-(2-데옥시-2-플루오로-4-티오-β-D-아라비노푸라노실)시토신의 합성 중간체, 티오뉴클레오시드의 합성 중간체, 및 그들의 제조법 |
| EP2992107B1 (en) * | 2013-04-29 | 2019-12-11 | Plasmia Biotech, S.L. | Biocatalytic production of nucleoside analogues as active pharmaceutical ingredients |
| JP6175553B2 (ja) | 2014-02-18 | 2017-08-09 | 富士フイルム株式会社 | チオラン骨格型糖化合物の製造方法およびチオラン骨格型糖化合物 |
| JP6204223B2 (ja) | 2014-02-19 | 2017-09-27 | 富士フイルム株式会社 | チオピラノース化合物等の製造方法 |
| TWI678373B (zh) | 2014-10-31 | 2019-12-01 | 日商富士軟片股份有限公司 | 硫代核苷衍生物或其鹽及醫藥組合物 |
| BR112019003946A2 (pt) | 2016-08-31 | 2019-05-21 | Fujifilm Corporation | agente antitumoral, reforçador do efeito antitumoral e kit antitumoral |
| MX2018002611A (es) | 2018-01-29 | 2019-07-30 | Fujifilm Corp | Agente antitumoral para cancer del tracto biliar y metodo para tratar cancer del tracto biliar. |
| WO2022008025A1 (en) * | 2020-07-05 | 2022-01-13 | Since & Technology Development Fund Authority | 2-hydroxyiminopyrimidine nucleosides and derivitives and antiviral uses thereto |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3155646A (en) * | 1960-08-23 | 1964-11-03 | Upjohn Co | 1-arabinofuranosyl-5-halouracil and process for the preparation thereof |
| US3282921A (en) * | 1964-06-04 | 1966-11-01 | Syntex Corp | Halo-deoxynucleosides and processes for the preparation thereof |
| US3539550A (en) * | 1967-01-23 | 1970-11-10 | Syntex Corp | Process for the preparation of 2'-halo-2'-deoxy pyrimidine nucleosides |
| US3721664A (en) * | 1970-01-27 | 1973-03-20 | Hoffmann La Roche | Preparation of 5-cytosine nucleosides |
| US3687931A (en) * | 1970-03-19 | 1972-08-29 | Syntex Corp | Halogenated purine and pyrimidine nucleosides and process therefor |
| US3817982A (en) * | 1971-12-29 | 1974-06-18 | Syntex Inc | 2{40 ,3{40 -unsaturated nucleosides and method of making |
| US3870700A (en) * | 1973-05-29 | 1975-03-11 | Miles Lab | 2-halogeno-2-deoxy-5-(substituted)uridines |
| US3873516A (en) * | 1973-05-29 | 1975-03-25 | Miles Lab | Process for the preparation of 1-{8 {62 -D-2-substituted-2-deoxyribofuranosyl{9 -pyrimidines |
-
1978
- 1978-10-02 US US05/948,189 patent/US4211773A/en not_active Expired - Lifetime
-
1979
- 1979-09-12 AU AU50757/79A patent/AU533135B2/en not_active Expired
- 1979-09-26 CA CA336,359A patent/CA1131626A/en not_active Expired
- 1979-09-27 EP EP79103673A patent/EP0010205B1/en not_active Expired
- 1979-09-27 DE DE7979103673T patent/DE2965318D1/de not_active Expired
- 1979-10-01 ES ES484626A patent/ES484626A1/es not_active Expired
- 1979-10-01 HU HU79SO1262A patent/HU182597B/hu unknown
- 1979-10-02 JP JP12727179A patent/JPS5549395A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11061285B2 (en) | 2006-05-16 | 2021-07-13 | Semiconductor Energy Laboratory Co., Ltd. | Liquid crystal display device comprising a dogleg-like shaped pixel electrode in a plane view having a plurality of dogleg-like shaped openings and semiconductor device |
| US11106096B2 (en) | 2006-05-16 | 2021-08-31 | Semiconductor Energy Laboratory Co., Ltd. | Liquid crystal display device and semiconductor device |
| US11435626B2 (en) | 2006-05-16 | 2022-09-06 | Semiconductor Energy Laboratory Co., Ltd. | Liquid crystal display device and semiconductor device |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0010205A1 (en) | 1980-04-30 |
| JPS5549395A (en) | 1980-04-09 |
| US4211773A (en) | 1980-07-08 |
| ES484626A1 (es) | 1980-05-16 |
| AU533135B2 (en) | 1983-11-03 |
| EP0010205B1 (en) | 1983-05-04 |
| CA1131626A (en) | 1982-09-14 |
| DE2965318D1 (en) | 1983-06-09 |
| HU182597B (en) | 1984-02-28 |
| AU5075779A (en) | 1980-04-17 |
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