CA2503471A1 - 1-acyl-pyrrolidine derivatives for the treatment of viral infections - Google Patents
1-acyl-pyrrolidine derivatives for the treatment of viral infections Download PDFInfo
- Publication number
- CA2503471A1 CA2503471A1 CA002503471A CA2503471A CA2503471A1 CA 2503471 A1 CA2503471 A1 CA 2503471A1 CA 002503471 A CA002503471 A CA 002503471A CA 2503471 A CA2503471 A CA 2503471A CA 2503471 A1 CA2503471 A1 CA 2503471A1
- Authority
- CA
- Canada
- Prior art keywords
- tert
- pyrrolidine
- butylbenzoyl
- methoxy
- isobutyl
- 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.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 29
- 208000036142 Viral infection Diseases 0.000 title claims description 10
- 230000009385 viral infection Effects 0.000 title claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 365
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 88
- 125000003118 aryl group Chemical group 0.000 claims abstract description 69
- 239000001257 hydrogen Substances 0.000 claims abstract description 66
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 65
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 58
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 45
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 35
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 150000002148 esters Chemical class 0.000 claims abstract description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000012453 solvate Substances 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 33
- 150000001875 compounds Chemical class 0.000 claims description 363
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 133
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 66
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- -1 C(O)NR2R3 Chemical group 0.000 claims description 50
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
- 125000004122 cyclic group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 14
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- BBDXRCVFTQOLNZ-OFUUFJSKSA-N (2s,4s,5r)-1-(4-tert-butyl-3-chlorobenzoyl)-4-(ethoxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1([C@@H]2N([C@@](CC(C)C)(C[C@@H]2COCC)C(O)=O)C(=O)C=2C=C(Cl)C(=CC=2)C(C)(C)C)=NC=CS1 BBDXRCVFTQOLNZ-OFUUFJSKSA-N 0.000 claims description 4
- URHNVEKBTOYPNA-OFUUFJSKSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(methoxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1([C@@H]2N([C@@](CC(C)C)(C[C@@H]2COC)C(O)=O)C(=O)C=2C=C(OC)C(=CC=2)C(C)(C)C)=NC=CS1 URHNVEKBTOYPNA-OFUUFJSKSA-N 0.000 claims description 4
- 238000013160 medical therapy Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- GNSKKEXPOIMGRA-ZOIIRCJOSA-N (2s,4r,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(2-hydroxypropan-2-yl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@H]([C@@H]2C=2SC=CN=2)C(C)(C)O)(CC(C)C)C(O)=O)=C1 GNSKKEXPOIMGRA-ZOIIRCJOSA-N 0.000 claims description 3
- DHGFOQPHLMIWIF-XCIGCYOISA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-2-(2-methylpropyl)-4-(propoxymethyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1([C@@H]2N([C@@](CC(C)C)(C[C@@H]2COCCC)C(O)=O)C(=O)C=2C=C(OC)C(=CC=2)C(C)(C)C)=NC=CS1 DHGFOQPHLMIWIF-XCIGCYOISA-N 0.000 claims description 3
- BSBUQUPCVMXAIX-ZHCYEPILSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(ethoxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1([C@@H]2N([C@@](CC(C)C)(C[C@@H]2COCC)C(O)=O)C(=O)C=2C=C(OC)C(=CC=2)C(C)(C)C)=NC=CS1 BSBUQUPCVMXAIX-ZHCYEPILSA-N 0.000 claims description 3
- KKYQKBYLGJRVRK-UHFFFAOYSA-N 1-(2-aminobenzoyl)-4-(1-hydroxyethyl)pyrrolidine-2,2-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC(C(O)C)CN1C(=O)C1=CC=CC=C1N KKYQKBYLGJRVRK-UHFFFAOYSA-N 0.000 claims description 3
- FEMHUBYXVPOGIA-UHFFFAOYSA-N 4-(1-hydroxyethyl)-1-(2-nitrobenzoyl)pyrrolidine-2,2-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC(C(O)C)CN1C(=O)C1=CC=CC=C1[N+]([O-])=O FEMHUBYXVPOGIA-UHFFFAOYSA-N 0.000 claims description 3
- AXYLEOVJLXMRKW-UHFFFAOYSA-N 4-ethenyl-1-(2-nitrobenzoyl)pyrrolidine-2,2-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC(C=C)CN1C(=O)C1=CC=CC=C1[N+]([O-])=O AXYLEOVJLXMRKW-UHFFFAOYSA-N 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- CNJOQLFWCMXPPG-CDPAUJCKSA-N (2s,4r,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(1-hydroxyethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@H]([C@@H]2C=2SC=CN=2)C(C)O)(CC(C)C)C(O)=O)=C1 CNJOQLFWCMXPPG-CDPAUJCKSA-N 0.000 claims description 2
- PFZUXBHTBAMAOS-OFUUFJSKSA-N (2s,4s,5r)-1-(3-bromo-4-tert-butylbenzoyl)-4-(ethoxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1([C@@H]2N([C@@](CC(C)C)(C[C@@H]2COCC)C(O)=O)C(=O)C=2C=C(Br)C(=CC=2)C(C)(C)C)=NC=CS1 PFZUXBHTBAMAOS-OFUUFJSKSA-N 0.000 claims description 2
- FECFCUYXLBBKBO-XCIGCYOISA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-2-(2-methylpropyl)-4-(prop-2-enoxymethyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@H](COCC=C)[C@@H]2C=2SC=CN=2)(CC(C)C)C(O)=O)=C1 FECFCUYXLBBKBO-XCIGCYOISA-N 0.000 claims description 2
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- QOEZPCQIFFRMAG-OFUUFJSKSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(cyanomethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC(C(=O)N2[C@](C[C@@H](CC#N)[C@@H]2C=2SC=CN=2)(CC(C)C)C(O)=O)=C1 QOEZPCQIFFRMAG-OFUUFJSKSA-N 0.000 claims description 2
- MVXLYYMOZKDDSX-GDRRSRKRSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methoxybenzoyl)-4-(methoxymethyl)-2-(2-methylpropyl)-5-pyridin-2-ylpyrrolidine-2-carboxylic acid Chemical compound C1([C@@H]2N([C@@](CC(C)C)(C[C@@H]2COC)C(O)=O)C(=O)C=2C=C(OC)C(=CC=2)C(C)(C)C)=CC=CC=N1 MVXLYYMOZKDDSX-GDRRSRKRSA-N 0.000 claims description 2
- QUEDXIIQZYWKOH-NTOOTBGVSA-N (2s,4s,5r)-1-(4-tert-butyl-3-methylbenzoyl)-4-(ethoxymethyl)-2-(2-methylpropyl)-5-(1,3-thiazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1([C@@H]2N([C@@](CC(C)C)(C[C@@H]2COCC)C(O)=O)C(=O)C=2C=C(C)C(=CC=2)C(C)(C)C)=NC=CS1 QUEDXIIQZYWKOH-NTOOTBGVSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
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- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 abstract description 3
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- UBNRVNOCFSZCLP-UHFFFAOYSA-N tert-butyl 3-phenyl-2-(1,3-thiazol-2-ylmethylideneamino)propanoate Chemical compound N=1C=CSC=1C=NC(C(=O)OC(C)(C)C)CC1=CC=CC=C1 UBNRVNOCFSZCLP-UHFFFAOYSA-N 0.000 description 1
- ODOGUYJIAWRTIQ-UHFFFAOYSA-N tert-butyl 4-methyl-2-(1,3-thiazol-2-ylmethylideneamino)pentanoate Chemical compound CC(C)(C)OC(=O)C(CC(C)C)N=CC1=NC=CS1 ODOGUYJIAWRTIQ-UHFFFAOYSA-N 0.000 description 1
- OSDQDLCUHSRSJH-UHFFFAOYSA-N tert-butyl 4-methyl-2-(pyridin-2-ylmethylideneamino)pentanoate Chemical compound CC(C)(C)OC(=O)C(CC(C)C)N=CC1=CC=CC=N1 OSDQDLCUHSRSJH-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
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- 239000010936 titanium Chemical group 0.000 description 1
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- 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
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- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
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- 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
- A61P31/18—Antivirals for RNA viruses for HIV
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- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0224774A GB0224774D0 (en) | 2002-10-24 | 2002-10-24 | Compounds |
| GB0224774.0 | 2002-10-24 | ||
| GB0229470A GB0229470D0 (en) | 2002-12-18 | 2002-12-18 | Compounds |
| GB0229470.0 | 2002-12-18 | ||
| GB0317141A GB0317141D0 (en) | 2003-07-22 | 2003-07-22 | Compounds |
| GB0317141.0 | 2003-07-22 | ||
| PCT/EP2003/011813 WO2004037818A1 (en) | 2002-10-24 | 2003-10-22 | 1-acyl-pyrrolidine derivatives for the treatment of viral infections |
Publications (1)
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|---|---|
| CA2503471A1 true CA2503471A1 (en) | 2004-05-06 |
Family
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Family Applications (1)
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|---|---|---|---|
| CA002503471A Abandoned CA2503471A1 (en) | 2002-10-24 | 2003-10-22 | 1-acyl-pyrrolidine derivatives for the treatment of viral infections |
Country Status (18)
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| EP (1) | EP1554274B1 (https=) |
| JP (1) | JP2006506455A (https=) |
| KR (1) | KR20050057670A (https=) |
| AR (1) | AR041816A1 (https=) |
| AT (1) | ATE418554T1 (https=) |
| AU (1) | AU2003276172A1 (https=) |
| BR (1) | BR0315417A (https=) |
| CA (1) | CA2503471A1 (https=) |
| CO (1) | CO5550450A2 (https=) |
| DE (1) | DE60325498D1 (https=) |
| IS (1) | IS7851A (https=) |
| MA (1) | MA27524A1 (https=) |
| MX (1) | MXPA05004435A (https=) |
| NO (1) | NO20052472L (https=) |
| PL (1) | PL376454A1 (https=) |
| TW (1) | TW200418848A (https=) |
| WO (1) | WO2004037818A1 (https=) |
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| GB0304494D0 (en) * | 2003-02-27 | 2003-04-02 | Glaxo Group Ltd | Compounds |
| GB0408995D0 (en) * | 2004-04-22 | 2004-05-26 | Glaxo Group Ltd | Compounds |
| GB0423673D0 (en) * | 2004-10-25 | 2004-11-24 | Glaxo Group Ltd | Compounds |
| GB0423672D0 (en) * | 2004-10-25 | 2004-11-24 | Glaxo Group Ltd | Compounds |
| JP4663733B2 (ja) * | 2004-10-29 | 2011-04-06 | シェーリング コーポレイション | 抗ウイルス物質としての置換５−オキソピラゾールおよび置換［１，２，４］トリアゾール |
| GB0519478D0 (en) * | 2005-09-23 | 2005-11-02 | Glaxo Group Ltd | Compounds |
| GB0519488D0 (en) * | 2005-09-23 | 2005-11-02 | Glaxo Group Ltd | Compounds |
| GB0519486D0 (en) * | 2005-09-23 | 2005-11-02 | Glaxo Group Ltd | Compounds |
| GB0519485D0 (en) * | 2005-09-23 | 2005-11-02 | Glaxo Group Ltd | Compounds |
| PT2144604E (pt) | 2007-02-28 | 2011-10-19 | Conatus Pharmaceuticals Inc | Métodos para o tratamento da hepatite c viral crónica utilizando ro-113-0830 |
| ES2381410T3 (es) | 2007-05-04 | 2012-05-28 | Vertex Pharmceuticals Incorporated | Terapia de combinación paa el tratamiento de infecciones por VHC |
| US20090053175A1 (en) * | 2007-08-24 | 2009-02-26 | Yat Sun Or | Substitute pyrrolidine derivatives |
| EP2272832A4 (en) | 2008-04-28 | 2011-09-07 | Asahi Kasei Pharma Corp | PHENYLPROPIONIC ACID DERIVATIVE AND USE THEREOF |
| JP2011530562A (ja) | 2008-08-11 | 2011-12-22 | グラクソスミスクライン エルエルシー | アレルギー性、炎症性及び感染性疾患治療用のプリン誘導体 |
| UA103195C2 (uk) | 2008-08-11 | 2013-09-25 | Глаксосмитклайн Ллк | Похідні пурину для застосування у лікуванні алергій, запальних та інфекційних захворювань |
| SI2320905T1 (sl) | 2008-08-11 | 2017-10-30 | Glaxosmithkline Llc Corporation Service Company | Novi adeninski derivati |
| EP2534149B1 (en) | 2010-02-10 | 2014-10-15 | GlaxoSmithKline LLC | 6-amino-2-{[(1s)-1-methylbutyl]oxy}-9-[5-(1-piperidinyl)pentyl]-7,9-dihydro-8h-purin-8-one maleate |
| US8575340B2 (en) | 2010-02-10 | 2013-11-05 | Glaxosmithkline Llc | Purine derivatives and their pharmaceutical uses |
| WO2013134012A1 (en) | 2012-03-06 | 2013-09-12 | Merck Sharp & Dohme Corp. | Preparation and use of bicyclic himbacine derivatives as par-receptor antagonists |
| KR20160124157A (ko) | 2014-02-20 | 2016-10-26 | 글락소스미스클라인 인털렉츄얼 프로퍼티 (넘버 2) 리미티드 | 인간 인터페론의 유도인자로서의 피롤로[3,2]피리미딘 유도체 |
| MX2017006302A (es) | 2014-11-13 | 2018-02-16 | Glaxosmithkline Biologicals Sa | Derivados de adenina que son utiles en el tratamiento de enfermedades alergicas u otras afecciones inflamatorias. |
| TWI704154B (zh) | 2015-12-03 | 2020-09-11 | 英商葛蘭素史克智慧財產發展有限公司 | 新穎化合物 |
| HRP20220936T1 (hr) | 2016-04-07 | 2022-10-28 | Glaxosmithkline Intellectual Property Development Limited | Heterociklički amidi korisni kao modulatori proteina |
| JP2019510802A (ja) | 2016-04-07 | 2019-04-18 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | タンパク質調節物質として有用な複素環アミド |
| US20210238172A1 (en) | 2017-10-05 | 2021-08-05 | Glaxosmithkline Intellectual Property Development Limited | Heterocyclic amides useful as protein modulators and methods of using the same |
| CA3077337A1 (en) | 2017-10-05 | 2019-04-11 | Glaxosmithkline Intellectual Property Development Limited | Modulators of stimulator of interferon genes (sting) |
| GB201807924D0 (en) | 2018-05-16 | 2018-06-27 | Ctxt Pty Ltd | Compounds |
| JP2022533194A (ja) | 2019-05-16 | 2022-07-21 | スティングセラ インコーポレイテッド | ベンゾ［ｂ］［１，８］ナフチリジン酢酸誘導体および使用方法 |
| US20220227761A1 (en) | 2019-05-16 | 2022-07-21 | Stingthera, Inc. | Oxoacridinyl acetic acid derivatives and methods of use |
| GB201910304D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| GB201910305D0 (en) | 2019-07-18 | 2019-09-04 | Ctxt Pty Ltd | Compounds |
| CN114981265B (zh) | 2019-12-18 | 2025-01-03 | Ctxt私人有限公司 | 化合物 |
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| AU5687396A (en) | 1995-04-21 | 1996-11-07 | Novarits Ag | N-aroylamino acid amides as endothelin inhibitors |
| AU1804299A (en) | 1997-12-08 | 1999-06-28 | Glycomed Incorporated | Sialyl lewis x and sialyl lewis a glycomimetics |
| ATE391451T1 (de) | 1998-01-26 | 2008-04-15 | Massachusetts Inst Technology | Endoskop zur erfassung von fluoreszenzbilder |
| EP1315698A1 (en) | 1998-04-23 | 2003-06-04 | Abbott Laboratories | Pyrrolidines as inhibitors of neuraminidases |
| US6323180B1 (en) | 1998-08-10 | 2001-11-27 | Boehringer Ingelheim (Canada) Ltd | Hepatitis C inhibitor tri-peptides |
| EP1118287B1 (de) * | 2000-01-21 | 2004-11-24 | Alois Ing. Sampl | Steckbares Regalsystem |
| EP1278743A4 (en) * | 2000-05-05 | 2003-05-14 | Smithkline Beecham Corp | NEW ANTI-INFECTIOUS ACTIVE SUBSTANCES |
| WO2002044168A2 (en) | 2000-11-20 | 2002-06-06 | Scios Inc. | Indole-type inhibitors of p38 kinase |
| BR0213760A (pt) | 2001-10-26 | 2004-10-19 | Upjohn Co | Composto, composição farmacêutica, uso do composto e método para tratamento de doença ou condição |
| JP2005511572A (ja) | 2001-11-02 | 2005-04-28 | グラクソ グループ リミテッド | Ｈｃｖ阻害剤としてのアシルジヒドロピロール誘導体 |
| CA2490385C (en) | 2002-10-28 | 2014-05-06 | Marquage Antivol Sherlock, Inc. | Method of preventing theft of vehicles using intensive marking |
-
2003
- 2003-10-22 MX MXPA05004435A patent/MXPA05004435A/es unknown
- 2003-10-22 AR ARP030103852A patent/AR041816A1/es not_active Application Discontinuation
- 2003-10-22 US US10/531,884 patent/US7304087B2/en not_active Expired - Fee Related
- 2003-10-22 WO PCT/EP2003/011813 patent/WO2004037818A1/en not_active Ceased
- 2003-10-22 EP EP03809322A patent/EP1554274B1/en not_active Expired - Lifetime
- 2003-10-22 AU AU2003276172A patent/AU2003276172A1/en not_active Abandoned
- 2003-10-22 PL PL03376454A patent/PL376454A1/xx not_active Application Discontinuation
- 2003-10-22 AT AT03809322T patent/ATE418554T1/de not_active IP Right Cessation
- 2003-10-22 DE DE60325498T patent/DE60325498D1/de not_active Expired - Fee Related
- 2003-10-22 TW TW092129213A patent/TW200418848A/zh unknown
- 2003-10-22 CA CA002503471A patent/CA2503471A1/en not_active Abandoned
- 2003-10-22 KR KR1020057006957A patent/KR20050057670A/ko not_active Withdrawn
- 2003-10-22 BR BR0315417-3A patent/BR0315417A/pt not_active IP Right Cessation
- 2003-10-22 JP JP2005501534A patent/JP2006506455A/ja not_active Withdrawn
-
2005
- 2005-04-25 CO CO05038997A patent/CO5550450A2/es not_active Application Discontinuation
- 2005-05-06 MA MA28263A patent/MA27524A1/fr unknown
- 2005-05-19 IS IS7851A patent/IS7851A/is unknown
- 2005-05-23 NO NO20052472A patent/NO20052472L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR041816A1 (es) | 2005-06-01 |
| DE60325498D1 (de) | 2009-02-05 |
| PL376454A1 (en) | 2005-12-27 |
| ATE418554T1 (de) | 2009-01-15 |
| KR20050057670A (ko) | 2005-06-16 |
| CO5550450A2 (es) | 2005-08-31 |
| US20060258720A1 (en) | 2006-11-16 |
| EP1554274A1 (en) | 2005-07-20 |
| MA27524A1 (fr) | 2005-09-01 |
| US7304087B2 (en) | 2007-12-04 |
| TW200418848A (en) | 2004-10-01 |
| JP2006506455A (ja) | 2006-02-23 |
| AU2003276172A1 (en) | 2004-05-13 |
| EP1554274B1 (en) | 2008-12-24 |
| NO20052472L (no) | 2005-05-23 |
| WO2004037818A1 (en) | 2004-05-06 |
| MXPA05004435A (es) | 2005-07-26 |
| BR0315417A (pt) | 2005-08-16 |
| IS7851A (is) | 2005-05-19 |
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Legal Events
| Date | Code | Title | Description |
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| FZDE | Discontinued |