AU784370B2 - Novel bisamidate phosphonate prodrugs - Google Patents
Novel bisamidate phosphonate prodrugs Download PDFInfo
- Publication number
- AU784370B2 AU784370B2 AU52447/01A AU5244701A AU784370B2 AU 784370 B2 AU784370 B2 AU 784370B2 AU 52447/01 A AU52447/01 A AU 52447/01A AU 5244701 A AU5244701 A AU 5244701A AU 784370 B2 AU784370 B2 AU 784370B2
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- Australia
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- alkyl
- aryl
- aralkyl
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- 239000000651 prodrug Substances 0.000 title description 45
- 229940002612 prodrug Drugs 0.000 title description 45
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 title description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 662
- 125000003118 aryl group Chemical group 0.000 claims description 614
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 467
- 150000001875 compounds Chemical class 0.000 claims description 359
- 125000005842 heteroatom Chemical group 0.000 claims description 277
- 125000002723 alicyclic group Chemical group 0.000 claims description 272
- 125000004429 atom Chemical group 0.000 claims description 262
- 229910052717 sulfur Inorganic materials 0.000 claims description 245
- -1 perhaloalkyl Chemical group 0.000 claims description 237
- 229910052739 hydrogen Inorganic materials 0.000 claims description 209
- 125000005843 halogen group Chemical group 0.000 claims description 197
- 125000004122 cyclic group Chemical group 0.000 claims description 178
- 229910052760 oxygen Inorganic materials 0.000 claims description 174
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 157
- 229910052757 nitrogen Inorganic materials 0.000 claims description 125
- 238000000034 method Methods 0.000 claims description 113
- 125000000304 alkynyl group Chemical group 0.000 claims description 89
- 125000003342 alkenyl group Chemical group 0.000 claims description 82
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- 229910052799 carbon Inorganic materials 0.000 claims description 80
- 150000003839 salts Chemical class 0.000 claims description 72
- 229910052698 phosphorus Inorganic materials 0.000 claims description 70
- 239000003814 drug Substances 0.000 claims description 63
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 60
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 52
- 241001465754 Metazoa Species 0.000 claims description 51
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 239000003112 inhibitor Substances 0.000 claims description 50
- 238000004519 manufacturing process Methods 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 45
- 150000002367 halogens Chemical group 0.000 claims description 43
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 38
- 125000004437 phosphorous atom Chemical group 0.000 claims description 37
- 229910052711 selenium Inorganic materials 0.000 claims description 37
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 33
- 239000011574 phosphorus Substances 0.000 claims description 33
- 125000001188 haloalkyl group Chemical group 0.000 claims description 32
- 150000001721 carbon Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
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- 230000002401 inhibitory effect Effects 0.000 claims description 26
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 25
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 238000000338 in vitro Methods 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 21
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- 125000003545 alkoxy group Chemical group 0.000 claims description 20
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- 201000010099 disease Diseases 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 125000005647 linker group Chemical group 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 16
- 125000001041 indolyl group Chemical group 0.000 claims description 16
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 15
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 125000001543 furan-2,5-diyl group Chemical group O1C(=CC=C1*)* 0.000 claims description 14
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 150000003462 sulfoxides Chemical class 0.000 claims description 13
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 208000007345 glycogen storage disease Diseases 0.000 claims description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
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- 239000002253 acid Substances 0.000 claims description 10
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
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- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 9
- 150000001409 amidines Chemical class 0.000 claims description 9
- 208000037906 ischaemic injury Diseases 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 8
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000001965 increasing effect Effects 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 6
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- 229910018830 PO3H Inorganic materials 0.000 claims description 5
- 230000002440 hepatic effect Effects 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
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- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
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- 101710099475 3'-phosphoadenosine 5'-phosphate phosphatase Proteins 0.000 claims 9
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- 101710198902 Fructose-1,6-bisphosphate aldolase/phosphatase Proteins 0.000 claims 9
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 4
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- 125000006366 methylene oxy carbonyl group Chemical group [H]C([H])([*:1])OC([*:2])=O 0.000 claims 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
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- A—HUMAN NECESSITIES
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4465—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2006202624A AU2006202624B2 (en) | 1999-12-22 | 2006-06-20 | Novel bisamidate phosphonate prodrugs |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17186299P | 1999-12-22 | 1999-12-22 | |
| US60/171862 | 1999-12-22 | ||
| PCT/IB2000/002071 WO2001047935A2 (en) | 1999-12-22 | 2000-12-22 | Novel bisamidate phosphonate prodrugs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006202624A Division AU2006202624B2 (en) | 1999-12-22 | 2006-06-20 | Novel bisamidate phosphonate prodrugs |
Publications (2)
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| AU5244701A AU5244701A (en) | 2001-07-09 |
| AU784370B2 true AU784370B2 (en) | 2006-03-23 |
Family
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| AU52447/01A Ceased AU784370B2 (en) | 1999-12-22 | 2000-12-22 | Novel bisamidate phosphonate prodrugs |
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| JP (1) | JP2003519154A (enExample) |
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| BR (1) | BR0017048A (enExample) |
| CA (1) | CA2396713A1 (enExample) |
| CZ (1) | CZ301401B6 (enExample) |
| HK (1) | HK1049841A1 (enExample) |
| HU (1) | HUP0204092A3 (enExample) |
| IL (1) | IL149887A0 (enExample) |
| MX (1) | MXPA02006156A (enExample) |
| NO (1) | NO20022932L (enExample) |
| NZ (1) | NZ519219A (enExample) |
| PL (1) | PL356525A1 (enExample) |
| RU (2) | RU2273642C2 (enExample) |
| SK (1) | SK8892002A3 (enExample) |
| WO (1) | WO2001047935A2 (enExample) |
| ZA (1) | ZA200204399B (enExample) |
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| KR100814426B1 (ko) * | 2001-07-14 | 2008-03-18 | 삼성전자주식회사 | 다 채널 영상 중계 처리기 및 이를 적용한 다 채널 영상보안 시스템 |
| US7015941B2 (en) * | 2001-10-12 | 2006-03-21 | Malloy Desormeaux Stephen G | Hybrid cameras that download electronic images in selected geometric formats and methods |
| JP2003304482A (ja) * | 2002-02-08 | 2003-10-24 | Nikon Corp | 電子カメラ |
| JP2004038515A (ja) * | 2002-07-03 | 2004-02-05 | Sanyo Electric Co Ltd | データ記録装置 |
| JP3781017B2 (ja) * | 2002-07-22 | 2006-05-31 | カシオ計算機株式会社 | 画像管理システム及び画像管理方法、デジタルカメラ |
| US20040156615A1 (en) * | 2002-07-25 | 2004-08-12 | Fuji Photo Film Co., Ltd | Method and apparatus for image reproduction, method and apparatus for image recording, and programs therefor |
| US20050093998A1 (en) * | 2003-11-03 | 2005-05-05 | Haas William R. | Digital camera with variable size delete buffer |
-
2000
- 2000-12-22 AU AU52447/01A patent/AU784370B2/en not_active Ceased
- 2000-12-22 EP EP00993135A patent/EP1240174A2/en not_active Withdrawn
- 2000-12-22 HU HU0204092A patent/HUP0204092A3/hu unknown
- 2000-12-22 CZ CZ20022172A patent/CZ301401B6/cs not_active IP Right Cessation
- 2000-12-22 KR KR1020027008017A patent/KR100875335B1/ko not_active Expired - Fee Related
- 2000-12-22 NZ NZ519219A patent/NZ519219A/en not_active IP Right Cessation
- 2000-12-22 WO PCT/IB2000/002071 patent/WO2001047935A2/en not_active Ceased
- 2000-12-22 RU RU2002119708/04A patent/RU2273642C2/ru not_active IP Right Cessation
- 2000-12-22 CN CNA2005100930590A patent/CN1740182A/zh active Pending
- 2000-12-22 US US09/747,182 patent/US6965033B2/en not_active Expired - Lifetime
- 2000-12-22 CA CA002396713A patent/CA2396713A1/en not_active Abandoned
- 2000-12-22 SK SK889-2002A patent/SK8892002A3/sk not_active Application Discontinuation
- 2000-12-22 BR BR0017048-8A patent/BR0017048A/pt not_active Application Discontinuation
- 2000-12-22 PL PL00356525A patent/PL356525A1/xx not_active Application Discontinuation
- 2000-12-22 CN CN00819044A patent/CN100595204C/zh not_active Expired - Fee Related
- 2000-12-22 JP JP2001549405A patent/JP2003519154A/ja active Pending
- 2000-12-22 HK HK03101952.1A patent/HK1049841A1/zh unknown
- 2000-12-22 IL IL14988700A patent/IL149887A0/xx unknown
- 2000-12-22 MX MXPA02006156A patent/MXPA02006156A/es active IP Right Grant
-
2002
- 2002-05-31 ZA ZA200204399A patent/ZA200204399B/xx unknown
- 2002-06-18 NO NO20022932A patent/NO20022932L/no not_active Application Discontinuation
-
2004
- 2004-07-28 US US10/900,718 patent/US20050004077A1/en not_active Abandoned
-
2005
- 2005-12-12 RU RU2005138719/04A patent/RU2005138719A/ru not_active Application Discontinuation
-
2009
- 2009-03-26 US US12/411,951 patent/US20090192121A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1995007920A1 (en) * | 1993-09-17 | 1995-03-23 | Gilead Sciences, Inc. | Nucleotide analogs |
| WO1998039344A1 (en) * | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel purine inhibitors of fructose-1,6-bisphosphatase |
| WO1998039343A1 (en) * | 1997-03-07 | 1998-09-11 | Metabasis Therapeutics, Inc. | Novel benzimidazole inhibitors of fructose-1,6-bisphosphatase |
Also Published As
| Publication number | Publication date |
|---|---|
| IL149887A0 (en) | 2002-11-10 |
| US6965033B2 (en) | 2005-11-15 |
| PL356525A1 (en) | 2004-06-28 |
| HUP0204092A2 (hu) | 2003-03-28 |
| US20090192121A1 (en) | 2009-07-30 |
| HK1049841A1 (zh) | 2003-05-30 |
| AU5244701A (en) | 2001-07-09 |
| JP2003519154A (ja) | 2003-06-17 |
| CN1434828A (zh) | 2003-08-06 |
| WO2001047935A2 (en) | 2001-07-05 |
| US20050004077A1 (en) | 2005-01-06 |
| NO20022932D0 (no) | 2002-06-18 |
| KR20020063248A (ko) | 2002-08-01 |
| EP1240174A2 (en) | 2002-09-18 |
| WO2001047935A3 (en) | 2002-03-21 |
| CN100595204C (zh) | 2010-03-24 |
| NO20022932L (no) | 2002-08-22 |
| US20020173490A1 (en) | 2002-11-21 |
| KR100875335B1 (ko) | 2008-12-22 |
| RU2002119708A (ru) | 2004-03-20 |
| CA2396713A1 (en) | 2001-07-05 |
| BR0017048A (pt) | 2002-11-05 |
| CZ20022172A3 (cs) | 2003-01-15 |
| RU2273642C2 (ru) | 2006-04-10 |
| ZA200204399B (en) | 2003-11-26 |
| HUP0204092A3 (en) | 2005-02-28 |
| RU2005138719A (ru) | 2007-06-20 |
| MXPA02006156A (es) | 2003-09-22 |
| SK8892002A3 (en) | 2003-04-01 |
| CN1740182A (zh) | 2006-03-01 |
| CZ301401B6 (cs) | 2010-02-17 |
| NZ519219A (en) | 2004-03-26 |
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