TWI496784B - 嘌呤類似物之環丙烷羧酸酯 - Google Patents
嘌呤類似物之環丙烷羧酸酯 Download PDFInfo
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- TWI496784B TWI496784B TW102113981A TW102113981A TWI496784B TW I496784 B TWI496784 B TW I496784B TW 102113981 A TW102113981 A TW 102113981A TW 102113981 A TW102113981 A TW 102113981A TW I496784 B TWI496784 B TW I496784B
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- compound
- alkyl
- amino
- halogenated
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- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 3
- 229940045686 antimetabolites antineoplastic purine analogs Drugs 0.000 title 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 110
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 208000009889 Herpes Simplex Diseases 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- WCSASARZTXJEJS-UHFFFAOYSA-N 1-amino-2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1(N)C(O)=O WCSASARZTXJEJS-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
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- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- MIZHFVXTEOEHQZ-UHFFFAOYSA-N 1-amino-2-(4-bromophenyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(N)CC1C1=CC=C(Br)C=C1 MIZHFVXTEOEHQZ-UHFFFAOYSA-N 0.000 claims description 2
- YCPRVMISNDOCQH-UHFFFAOYSA-N 1-amino-2-(furan-2-yl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(N)CC1C1=CC=CO1 YCPRVMISNDOCQH-UHFFFAOYSA-N 0.000 claims description 2
- MRUPFDZGTJQLCH-UHFFFAOYSA-N 1-amino-2-phenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(N)CC1C1=CC=CC=C1 MRUPFDZGTJQLCH-UHFFFAOYSA-N 0.000 claims description 2
- RWDTZPMFXSAITL-UHFFFAOYSA-N 1-amino-2-pyridin-2-ylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(N)CC1C1=CC=CC=N1 RWDTZPMFXSAITL-UHFFFAOYSA-N 0.000 claims description 2
- XYADPSWBCYPNKY-UHFFFAOYSA-N 1-azaniumyl-2-(trifluoromethyl)cyclopropane-1-carboxylate Chemical compound OC(=O)C1(N)CC1C(F)(F)F XYADPSWBCYPNKY-UHFFFAOYSA-N 0.000 claims description 2
- CUDYUNNRMLWYTR-UHFFFAOYSA-N 1-amino-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1(N)C(O)=O CUDYUNNRMLWYTR-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- -1 ganciclovir cyclopropanecarboxylate derivatives Chemical class 0.000 description 40
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- 229960002963 ganciclovir Drugs 0.000 description 30
- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 28
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- 239000002904 solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 230000000120 cytopathologic effect Effects 0.000 description 8
- 239000002207 metabolite Substances 0.000 description 8
- 239000012453 solvate Substances 0.000 description 8
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- 210000004027 cell Anatomy 0.000 description 6
- 238000004896 high resolution mass spectrometry Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 206010023332 keratitis Diseases 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 239000002504 physiological saline solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 208000006069 Corneal Opacity Diseases 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000006242 amine protecting group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 231100000269 corneal opacity Toxicity 0.000 description 4
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 description 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
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- 229960002149 valganciclovir Drugs 0.000 description 1
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- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
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- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/43—Enzymes; Proenzymes; Derivatives thereof
- A61K38/45—Transferases (2)
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Oncology (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
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| US201261635931P | 2012-04-20 | 2012-04-20 |
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| TWI496784B true TWI496784B (zh) | 2015-08-21 |
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| TW102113856A TWI458709B (zh) | 2012-04-20 | 2013-04-19 | 作為蛋白質激酶抑制劑之吲哚啉－２－酮衍生物 |
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| EP (2) | EP2838538B1 (instruction) |
| JP (2) | JP6177879B2 (instruction) |
| KR (2) | KR101774861B1 (instruction) |
| CN (2) | CN104394868A (instruction) |
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| BR (1) | BR112014026182A2 (instruction) |
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| IL (2) | IL235098A0 (instruction) |
| IN (2) | IN2014MN02105A (instruction) |
| RU (2) | RU2642463C2 (instruction) |
| TW (2) | TWI496784B (instruction) |
| WO (2) | WO2013158367A1 (instruction) |
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| WO2014155301A1 (en) * | 2013-03-26 | 2014-10-02 | Piramal Enterprises Limited | Substituted bicyclic compounds as inhibitors of ezh2 |
| HRP20201158T1 (hr) * | 2015-11-06 | 2020-11-13 | F. Hoffmann - La Roche Ag | Derivati indolin-2-ona |
| CN106831707B (zh) * | 2016-12-28 | 2019-09-20 | 杭州市西溪医院 | 作为c-Met激酶抑制剂的苯并杂环类衍生物及其医疗用途 |
| GB201709456D0 (en) * | 2017-06-14 | 2017-07-26 | Ucb Biopharma Sprl | Therapeutic agents |
| US20240067771A1 (en) | 2020-12-23 | 2024-02-29 | Basf Se | New catalyst for producing polyurethanes |
| CN113307799B (zh) * | 2021-05-21 | 2022-07-19 | 大连医科大学 | 一种检测葡萄糖醛酸转移酶1a1荧光探针及其应用 |
| CN113999221B (zh) * | 2021-11-04 | 2024-04-05 | 南京中医药大学 | 6-位取代的吲哚酮衍生物及其医药用途 |
| CN114380802B (zh) * | 2022-01-07 | 2023-11-17 | 贵州大学 | 一类含咔唑基咪唑盐类化合物及其制备方法和应用 |
| CN120359252A (zh) | 2022-11-24 | 2025-07-22 | 巴斯夫欧洲公司 | 用于制备聚氨酯的含胺多元醇组分中的氢氟烯烃的储存稳定性的改善 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5543414A (en) * | 1994-07-28 | 1996-08-06 | Syntex (Usa) Inc. | Achiral amino acid acyl esters of ganciclovir and its derivatives |
| WO2006127217A2 (en) * | 2005-05-25 | 2006-11-30 | Eli Lilly And Company | Cyclopropanecarboxylate esters of acyclovir |
| WO2009142827A2 (en) * | 2008-03-28 | 2009-11-26 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Compounds and methods for the treatment of viral infection |
| CN102083437A (zh) * | 2008-03-07 | 2011-06-01 | 雷·W·埃克斯利 | 疱疹病毒相关疾病的治疗 |
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| AT351865B (de) | 1977-04-01 | 1979-08-27 | Hoffmann La Roche | Akarizide mittel |
| KR100743287B1 (ko) * | 1998-05-29 | 2007-07-26 | 수젠, 인크. | 피롤기로 치환된 2-인돌리논 단백질 인산화 효소 억제제 |
| AU2001239770B2 (en) | 2000-02-15 | 2006-01-05 | Pharmacia & Upjohn Company | Pyrrole substituted 2-indolinone protein kinase inhibitors |
| US20090264494A1 (en) * | 2002-10-18 | 2009-10-22 | Board Of Regents, The University Of Texas System | Use of neuroprotective 3-substituted indolone compositions |
| CA2541460A1 (en) | 2003-10-24 | 2005-05-06 | Schering Aktiengesellschaft | Indolinone derivatives and their use in treating disease-states such as cancer |
| GT200500321A (es) * | 2004-11-09 | 2006-09-04 | Compuestos y composiciones como inhibidores de proteina kinase. | |
| AU2006294600A1 (en) | 2005-09-22 | 2007-04-05 | The Scripps Research Institute | Alkoxy indolinone based protein kinase inhibitors |
| CN1850794A (zh) * | 2006-05-30 | 2006-10-25 | 中国医学科学院医药生物技术研究所 | 3－酰胺基取代苯甲酰脲类化合物及其抗肿瘤作用 |
| AU2007333536A1 (en) | 2006-12-11 | 2008-06-19 | Irm Llc | Compounds and compositions as kinase inhibitors |
| ES2391912T3 (es) * | 2006-12-13 | 2012-12-03 | F. Hoffmann-La Roche Ag | Formulación en polvo del valganciclovir |
| CA2690569A1 (en) | 2007-06-12 | 2008-12-18 | Boehringer Ingelheim International Gmbh | Indolinone derivatives and their use in treating disease-states such as cancer |
| US7846793B2 (en) | 2007-10-03 | 2010-12-07 | Applied Materials, Inc. | Plasma surface treatment for SI and metal nanocrystal nucleation |
| PE20100087A1 (es) * | 2008-06-25 | 2010-02-08 | Irm Llc | Compuestos y composiciones como inhibidores de cinasa |
| RU2011103189A (ru) * | 2008-06-30 | 2012-08-10 | Силин Фармасьютикалз, Инк. (Us) | Производные оксиндола |
| US20100298376A1 (en) * | 2009-05-13 | 2010-11-25 | Board Of Regents, The University Of Texas System | Use of novel neuroprotective 3-substituted indolone compositions |
| GB201014374D0 (en) * | 2010-08-27 | 2010-10-13 | Univ Greenwich | Novel hybrid compounds |
| BR112013008510A2 (pt) * | 2010-10-08 | 2016-07-05 | Novartis Ag | vitamina e formulações de inibidores de sulfamida ns3 |
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Patent Citations (4)
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|---|---|---|---|---|
| US5543414A (en) * | 1994-07-28 | 1996-08-06 | Syntex (Usa) Inc. | Achiral amino acid acyl esters of ganciclovir and its derivatives |
| WO2006127217A2 (en) * | 2005-05-25 | 2006-11-30 | Eli Lilly And Company | Cyclopropanecarboxylate esters of acyclovir |
| CN102083437A (zh) * | 2008-03-07 | 2011-06-01 | 雷·W·埃克斯利 | 疱疹病毒相关疾病的治疗 |
| WO2009142827A2 (en) * | 2008-03-28 | 2009-11-26 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Compounds and methods for the treatment of viral infection |
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