MX2010013630A - Derivados triciclicos de indol y metodos de uso de los mismos. - Google Patents
Derivados triciclicos de indol y metodos de uso de los mismos.Info
- Publication number
- MX2010013630A MX2010013630A MX2010013630A MX2010013630A MX2010013630A MX 2010013630 A MX2010013630 A MX 2010013630A MX 2010013630 A MX2010013630 A MX 2010013630A MX 2010013630 A MX2010013630 A MX 2010013630A MX 2010013630 A MX2010013630 A MX 2010013630A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- pharmaceutically acceptable
- inhibitor
- interferon
- agent
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract description 31
- 150000002475 indoles Chemical class 0.000 title abstract description 19
- 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract description 5
- 230000009385 viral infection Effects 0.000 claims abstract description 21
- 208000036142 Viral infection Diseases 0.000 claims abstract description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 212
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
- 239000003112 inhibitor Substances 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000012453 solvate Substances 0.000 claims description 32
- 108010050904 Interferons Proteins 0.000 claims description 27
- 102000014150 Interferons Human genes 0.000 claims description 27
- 229940079322 interferon Drugs 0.000 claims description 27
- 239000000651 prodrug Substances 0.000 claims description 27
- 229940002612 prodrug Drugs 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 25
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 13
- 239000003443 antiviral agent Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 230000003612 virological effect Effects 0.000 claims description 13
- 108091005804 Peptidases Proteins 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 11
- 239000004365 Protease Substances 0.000 claims description 11
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 11
- 229960000329 ribavirin Drugs 0.000 claims description 11
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 11
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 10
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 8
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 108010078049 Interferon alpha-2 Proteins 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 230000010076 replication Effects 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 108010010648 interferon alfacon-1 Proteins 0.000 claims description 4
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 3
- 229960000517 boceprevir Drugs 0.000 claims description 3
- LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 claims description 3
- 229960003507 interferon alfa-2b Drugs 0.000 claims description 3
- 229960003358 interferon alfacon-1 Drugs 0.000 claims description 3
- MIXCUJKCXRNYFM-UHFFFAOYSA-M sodium;diiodomethanesulfonate;n-propyl-n-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide Chemical compound [Na+].[O-]S(=O)(=O)C(I)I.C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl MIXCUJKCXRNYFM-UHFFFAOYSA-M 0.000 claims description 3
- 210000002845 virion Anatomy 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229960003521 interferon alfa-2a Drugs 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 229960002935 telaprevir Drugs 0.000 claims 2
- BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 claims 2
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- 238000009175 antibody therapy Methods 0.000 claims 1
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- 239000000203 mixture Substances 0.000 abstract description 63
- 241000700605 Viruses Species 0.000 abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 121
- 238000003786 synthesis reaction Methods 0.000 description 96
- 239000000243 solution Substances 0.000 description 95
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 64
- 239000003814 drug Substances 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 46
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- 229940124597 therapeutic agent Drugs 0.000 description 44
- 238000002360 preparation method Methods 0.000 description 42
- -1 (2-dipropylamino) ethyl Chemical group 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 38
- 239000011541 reaction mixture Substances 0.000 description 38
- 238000003756 stirring Methods 0.000 description 38
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- 239000000047 product Substances 0.000 description 31
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- 239000000543 intermediate Substances 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 208000035475 disorder Diseases 0.000 description 16
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 16
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- 239000012267 brine Substances 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
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- 230000002829 reductive effect Effects 0.000 description 9
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- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 7
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 7
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 description 1
- 229960004231 thymalfasin Drugs 0.000 description 1
- 229960000838 tipranavir Drugs 0.000 description 1
- SUJUHGSWHZTSEU-FYBSXPHGSA-N tipranavir Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)=C(O)C1)CC1=CC=CC=C1 SUJUHGSWHZTSEU-FYBSXPHGSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 101150117196 tra-1 gene Proteins 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 208000027185 varicose disease Diseases 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- PNAMDJVUJCJOIX-XVZWKFLSSA-N vytorin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1.N1([C@@H]([C@H](C1=O)CC[C@@H](O)C=1C=CC(F)=CC=1)C=1C=CC(O)=CC=1)C1=CC=C(F)C=C1 PNAMDJVUJCJOIX-XVZWKFLSSA-N 0.000 description 1
- 229940009349 vytorin Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- LQUPKVMEAATBSL-UHFFFAOYSA-L zinc;2,3,4-trichlorophenolate Chemical compound [Zn+2].[O-]C1=CC=C(Cl)C(Cl)=C1Cl.[O-]C1=CC=C(Cl)C(Cl)=C1Cl LQUPKVMEAATBSL-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6134408P | 2008-06-13 | 2008-06-13 | |
| PCT/US2009/046822 WO2009152200A1 (en) | 2008-06-13 | 2009-06-10 | Tricyclic indole derivatives and methods of use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2010013630A true MX2010013630A (es) | 2010-12-21 |
Family
ID=40943627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010013630A MX2010013630A (es) | 2008-06-13 | 2009-06-10 | Derivados triciclicos de indol y metodos de uso de los mismos. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8901139B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2303893B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP5580814B2 (cg-RX-API-DMAC10.html) |
| CN (1) | CN102159579B (cg-RX-API-DMAC10.html) |
| AR (1) | AR072088A1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2727620A1 (cg-RX-API-DMAC10.html) |
| MX (1) | MX2010013630A (cg-RX-API-DMAC10.html) |
| TW (1) | TW201011030A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2009152200A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5079818B2 (ja) | 2006-12-22 | 2012-11-21 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｈｃｖおよび関連するウイルス疾患の治療または予防のための４，５−環インドール誘導体 |
| CN113943306A (zh) | 2012-09-20 | 2022-01-18 | Udc 爱尔兰有限责任公司 | 供电子应用的氮杂二苯并呋喃和包含氮杂二苯并呋喃的电子器件 |
| ES2688147T3 (es) | 2014-03-21 | 2018-10-31 | Bristol-Myers Squibb Company | Compuestos de 6H-furo[2,3-e]indol para el tratamiento de la hepatitis C |
| WO2015160636A1 (en) | 2014-04-16 | 2015-10-22 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| WO2018151239A1 (ja) * | 2017-02-17 | 2018-08-23 | 第一三共株式会社 | ３，６－ジヒドロ－２Ｈ－フロ［２，３－ｅ］インドール化合物 |
| CN116063310A (zh) * | 2022-12-23 | 2023-05-05 | 齐鲁工业大学 | 一种呋喃并[3,4-b]吲哚衍生物及其合成方法 |
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| DE648639C (de) | 1935-05-19 | 1937-08-05 | I G Farbenindustrie Akt Ges | Verfahren zur Darstellung von Dipyrrolen |
| US3632805A (en) * | 1967-12-08 | 1972-01-04 | Sumitomo Chemical Co | Process for producing 1-aminoalkyl-benzodiazepine derivatives |
| AU575854B2 (en) * | 1983-10-04 | 1988-08-11 | Shionogi & Co., Ltd. | 7beta-(carboxyalkenamido) cephalosporins |
| US5017380A (en) * | 1986-07-02 | 1991-05-21 | Shionogi & Co., Ltd. | Gelatin hard capsule containing crystalline hydrate of oral cephalosporin |
| NZ220764A (en) * | 1986-07-02 | 1989-09-27 | Shionogi & Co | Crystalline form of 7beta((z)-2-(2-aminothiazol-4-yl)-4- carboxybut-2-enoylamino)-3-cephem-4-carboxylic acid and pharmaceutical compositions |
| CA2038925A1 (en) | 1990-03-26 | 1991-09-27 | Takashi Sohda | Indole derivatives, their production and use |
| JPH04149429A (ja) | 1990-10-12 | 1992-05-22 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー反転写真感光材料およびそれを用いた画像形成方法 |
| IT1278077B1 (it) | 1995-05-25 | 1997-11-17 | Angeletti P Ist Richerche Bio | Metodologia per riprodurre in vitro le attivita' di rna polimerasi rna-dipendente e di nucleotidiltransferasi terminale codificate dal |
| US5922757A (en) | 1996-09-30 | 1999-07-13 | The Regents Of The University Of California | Treatment and prevention of hepatic disorders |
| NZ335276A (en) | 1996-10-18 | 2000-09-29 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis C virus (HCV) NS3 (Non Structural Protein 3) protease |
| GB9623908D0 (en) | 1996-11-18 | 1997-01-08 | Hoffmann La Roche | Amino acid derivatives |
| PT1012180E (pt) | 1997-08-11 | 2005-04-29 | Boehringer Ingelheim Ca Ltd | Analogos de peptidos inibidores da hepatite c |
| FR2768146B1 (fr) | 1997-09-05 | 2000-05-05 | Oreal | Nouveaux composes de la famille des indole-carboxyliques et leur utilisation |
| HK1047947A1 (zh) * | 2000-04-05 | 2003-03-14 | Schering Corporation | 包含n-环状p2部分的丙型肝炎病毒的大环ns3-丝氨酸蛋白酶抑制剂 |
| AU2001253621A1 (en) * | 2000-04-19 | 2001-11-07 | Schering Corporation | Macrocyclic NS3-serine protease inhibitors of hepatitis C virus comprising alkyl and aryl alanine P2 moieties |
| AR034127A1 (es) * | 2000-07-21 | 2004-02-04 | Schering Corp | Imidazolidinonas como inhibidores de ns3-serina proteasa del virus de hepatitis c, composicion farmaceutica, un metodo para su preparacion, y el uso de las mismas para la manufactura de un medicamento |
| SK742003A3 (en) * | 2000-07-21 | 2003-06-03 | Schering Corp | Novel peptides as NS3-serine protease inhibitors of hepatitis C virus |
| AR029851A1 (es) * | 2000-07-21 | 2003-07-16 | Dendreon Corp | Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c |
| US7012066B2 (en) * | 2000-07-21 | 2006-03-14 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| IL154981A0 (en) | 2000-10-10 | 2003-10-31 | Smithkline Beecham Corp | Substituted indoles, pharmaceutical compositions containing such indoles and their use as ppay-y-binding agents |
| AU3659102A (en) * | 2000-12-12 | 2002-06-24 | Schering Corp | Diaryl peptides as ns3-serine protease inhibitors of hepatits c virus |
| CA2430808A1 (en) * | 2000-12-18 | 2002-06-27 | Eli Lilly And Company | Cycloalkylfused [g]-indole compounds as spla2-inhibitors in the treatment of inflammatory diseases |
| US7626026B2 (en) | 2001-02-22 | 2009-12-01 | University Of Bradford | Pyrrolo-indole and pyrrolo-quinoline derivatives as prodrugs for tumour treatment |
| EP2335700A1 (en) | 2001-07-25 | 2011-06-22 | Boehringer Ingelheim (Canada) Ltd. | Hepatitis C virus polymerase inhibitors with a heterobicylic structure |
| JP2006505571A (ja) | 2002-10-15 | 2006-02-16 | リゲル ファーマシューテイカルズ、インコーポレイテッド | 置換されたインドール及びｈｃｖ阻害剤としてのその使用 |
| US20050075331A1 (en) * | 2003-10-06 | 2005-04-07 | Pratt John K. | Anti-infective agents |
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| PE20090047A1 (es) * | 2003-11-10 | 2009-01-26 | Schering Corp | Anticuerpo recombinante humanizado anti-interleuquina 10 |
| EP1714427A1 (de) | 2004-02-09 | 2006-10-25 | Hörmann KG Antriebstechnik | Torantriebssystem mit seriellem bus für kommunikation der komponenten |
| RU2428428C9 (ru) | 2004-02-27 | 2012-03-10 | Шеринг Корпорейшн | Серусодержащие соединения, действующие как ингибиторы сериновой протеазы ns3 вируса гепатита с |
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| WO2005107745A1 (en) * | 2004-05-06 | 2005-11-17 | Schering Corporation | An inhibitor of hepatitis c |
| EP1604988A1 (en) | 2004-05-18 | 2005-12-14 | Sanofi-Aventis Deutschland GmbH | Pyridazinone derivatives, methods for producing them and their use as pharmaceuticals |
| WO2007084413A2 (en) | 2004-07-14 | 2007-07-26 | Ptc Therapeutics, Inc. | Methods for treating hepatitis c |
| US7153848B2 (en) | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
| WO2006034337A2 (en) | 2004-09-23 | 2006-03-30 | Wyeth | Carbazole and cyclopentaindole derivatives to treat infection with hepatitis c virus |
| DE102004047272A1 (de) | 2004-09-24 | 2006-04-06 | Schering Ag | Inhibitoren der löslichen Adenylatzyklase |
| RU2007119562A (ru) | 2004-10-26 | 2008-12-10 | Институто Ди Ричерке Ди Биолоджиа Молеколаре П Анджелетти Спа (It) | Тетрациклические производные индолов в качестве противовирусных агентов |
| US20110104109A1 (en) * | 2005-07-13 | 2011-05-05 | Frank Bennett | Tetracyclic indole derivatives and their use for treating or preventing viral infections |
| GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US7482360B2 (en) | 2005-09-23 | 2009-01-27 | Schering Corporation | Fused tetracyclic mGluR1 antagonists as therapeutic agents |
| JP2009523732A (ja) | 2006-01-13 | 2009-06-25 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎の治療方法 |
| MX2008010355A (es) * | 2006-02-09 | 2008-10-31 | Schering Corp | Combinaciones que comprenden inhibidores de proteasa del virus de la hepatitis c e inhibidores de polimerasa del virus de la hepatitis c, y metodos de tratamiento relacionados con los mismos. |
| KR20090106539A (ko) * | 2006-12-22 | 2009-10-09 | 쉐링 코포레이션 | Ｈｃｖ 및 관련 바이러스 감염을 치료 또는 예방하기 위한 4,5-환 환상 인돌 유도체 |
| JP5055377B2 (ja) * | 2006-12-22 | 2012-10-24 | シェーリング コーポレイション | ［５，６−環］環形成インドール誘導体およびその使用方法 |
| JP5079818B2 (ja) * | 2006-12-22 | 2012-11-21 | メルク・シャープ・アンド・ドーム・コーポレーション | Ｈｃｖおよび関連するウイルス疾患の治療または予防のための４，５−環インドール誘導体 |
| JP5179585B2 (ja) * | 2007-08-29 | 2013-04-10 | メルク・シャープ・アンド・ドーム・コーポレーション | 四環系インドール誘導体およびその使用法 |
| EP2195317B1 (en) * | 2007-08-29 | 2012-01-18 | Schering Corporation | 2,3-substituted azaindole derivatives for treating viral infections |
| WO2009032124A1 (en) * | 2007-08-29 | 2009-03-12 | Schering Corporation | Substituted indole derivatives and methods of use thereof |
| RU2010111550A (ru) * | 2007-08-29 | 2011-10-10 | Шеринг Корпорейшн (US) | 2,3-замещенные индольные производные для лечения вирусных инфекций |
| US8765757B2 (en) * | 2007-11-16 | 2014-07-01 | Merck Sharp & Dohme Corp. | 3-heterocyclic substituted indole derivatives and methods of use thereof |
| CN102317285A (zh) * | 2007-11-16 | 2012-01-11 | 先灵公司 | 3-氨基磺酰基取代的吲哚衍生物及其使用方法 |
-
2009
- 2009-06-10 JP JP2011513649A patent/JP5580814B2/ja active Active
- 2009-06-10 WO PCT/US2009/046822 patent/WO2009152200A1/en not_active Ceased
- 2009-06-10 EP EP09763490.1A patent/EP2303893B1/en not_active Not-in-force
- 2009-06-10 AR ARP090102091A patent/AR072088A1/es not_active Application Discontinuation
- 2009-06-10 CA CA2727620A patent/CA2727620A1/en not_active Abandoned
- 2009-06-10 US US12/997,654 patent/US8901139B2/en active Active
- 2009-06-10 MX MX2010013630A patent/MX2010013630A/es active IP Right Grant
- 2009-06-10 CN CN200980131569.9A patent/CN102159579B/zh active Active
- 2009-06-11 TW TW098119583A patent/TW201011030A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102159579B (zh) | 2015-03-25 |
| TW201011030A (en) | 2010-03-16 |
| AR072088A1 (es) | 2010-08-04 |
| US20110189127A1 (en) | 2011-08-04 |
| CA2727620A1 (en) | 2009-12-17 |
| EP2303893A1 (en) | 2011-04-06 |
| JP5580814B2 (ja) | 2014-08-27 |
| JP2011524359A (ja) | 2011-09-01 |
| US8901139B2 (en) | 2014-12-02 |
| WO2009152200A1 (en) | 2009-12-17 |
| CN102159579A (zh) | 2011-08-17 |
| EP2303893B1 (en) | 2016-12-07 |
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