ZA200308781B - Pyrazole derivatives as HIV reverse transcriptase inhibitors. - Google Patents
Pyrazole derivatives as HIV reverse transcriptase inhibitors. Download PDFInfo
- Publication number
- ZA200308781B ZA200308781B ZA200308781A ZA200308781A ZA200308781B ZA 200308781 B ZA200308781 B ZA 200308781B ZA 200308781 A ZA200308781 A ZA 200308781A ZA 200308781 A ZA200308781 A ZA 200308781A ZA 200308781 B ZA200308781 B ZA 200308781B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- alkyl
- substituted
- isopropyl
- pyridyl
- Prior art date
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- 150000003217 pyrazoles Chemical class 0.000 title abstract description 9
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 title abstract description 5
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 17
- 241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 9
- 230000001404 mediated effect Effects 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- -1 hydroxy, amino Chemical group 0.000 claims description 176
- 125000001424 substituent group Chemical group 0.000 claims description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 235000019000 fluorine Nutrition 0.000 claims description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 14
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 14
- 125000005002 aryl methyl group Chemical group 0.000 claims description 13
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 150000004702 methyl esters Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- DGMGBAZYKZEBCN-UHFFFAOYSA-N [cyano(hydroxy)amino] thiohypofluorite Chemical compound ON(SF)C#N DGMGBAZYKZEBCN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- HPKVLNVUKUBTGU-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-ethyl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(CC)N=C(CO)C=1CC1=CC=NC=C1 HPKVLNVUKUBTGU-UHFFFAOYSA-N 0.000 claims 1
- MSXAJIBSJLYBOY-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethoxymethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1COCC1=CC=NC=C1 MSXAJIBSJLYBOY-UHFFFAOYSA-N 0.000 claims 1
- RVAHELGGEXONEH-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethoxymethyl)pyrazol-3-yl]methyl carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(COC(N)=O)C=1COCC1=CC=NC=C1 RVAHELGGEXONEH-UHFFFAOYSA-N 0.000 claims 1
- HAUURQXLCOVNLL-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=NC=C1 HAUURQXLCOVNLL-UHFFFAOYSA-N 0.000 claims 1
- AQSLEAXCHMHJJH-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methyl carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(COC(N)=O)C=1CC1=CC=NC=C1 AQSLEAXCHMHJJH-UHFFFAOYSA-N 0.000 claims 1
- QQVBJSXOXZZXDV-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methyl n-methylcarbamate Chemical compound C=1C=NC=CC=1CC=1C(COC(=O)NC)=NN(C(C)C)C=1SC1=CC(Cl)=CC(Cl)=C1 QQVBJSXOXZZXDV-UHFFFAOYSA-N 0.000 claims 1
- CYEICROBFYOXPI-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(thiophen-2-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=CS1 CYEICROBFYOXPI-UHFFFAOYSA-N 0.000 claims 1
- IKEBYYWKPKJSSM-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(thiophen-2-ylmethyl)pyrazol-3-yl]methyl carbamate Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(COC(N)=O)C=1CC1=CC=CS1 IKEBYYWKPKJSSM-UHFFFAOYSA-N 0.000 claims 1
- HLAIHUXWSCAYHM-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-[(3,4-difluorophenyl)methyl]-1-propan-2-ylpyrazol-3-yl]methanol Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=C(F)C(F)=C1 HLAIHUXWSCAYHM-UHFFFAOYSA-N 0.000 claims 1
- ZZVUSIQKMJZFSY-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-[(3-methoxyphenyl)methyl]-1-propan-2-ylpyrazol-3-yl]methanol Chemical compound COC1=CC=CC(CC2=C(N(C(C)C)N=C2CO)SC=2C=C(Cl)C=C(Cl)C=2)=C1 ZZVUSIQKMJZFSY-UHFFFAOYSA-N 0.000 claims 1
- IFSIFGYRPVEASN-UHFFFAOYSA-N [5-(3,5-dichlorophenyl)sulfanyl-4-ethyl-1-propan-2-ylpyrazol-3-yl]methanol Chemical compound OCC1=NN(C(C)C)C(SC=2C=C(Cl)C=C(Cl)C=2)=C1CC IFSIFGYRPVEASN-UHFFFAOYSA-N 0.000 claims 1
- XBAUZMKFMSCWMY-UHFFFAOYSA-N [5-(3,5-dicyanophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methyl carbamate Chemical compound C=1C(C#N)=CC(C#N)=CC=1SC=1N(C(C)C)N=C(COC(N)=O)C=1CC1=CC=NC=C1 XBAUZMKFMSCWMY-UHFFFAOYSA-N 0.000 claims 1
- XKMLQNVIELJJRO-UHFFFAOYSA-N [5-(3,5-difluorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C(F)=CC(F)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=NC=C1 XKMLQNVIELJJRO-UHFFFAOYSA-N 0.000 claims 1
- FBAOEMZTRYDRBM-UHFFFAOYSA-N [5-(3-chlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methanol Chemical compound C=1C=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CO)C=1CC1=CC=NC=C1 FBAOEMZTRYDRBM-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XWZBFWRTWAQXAZ-UHFFFAOYSA-N n-[[5-(3,5-dichlorophenyl)sulfanyl-1-propan-2-yl-4-(pyridin-4-ylmethyl)pyrazol-3-yl]methyl]methanesulfonamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1SC=1N(C(C)C)N=C(CNS(C)(=O)=O)C=1CC1=CC=NC=C1 XWZBFWRTWAQXAZ-UHFFFAOYSA-N 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 8
- 230000029812 viral genome replication Effects 0.000 abstract description 3
- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 125000004076 pyridyl group Chemical group 0.000 description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 description 9
- 208000031886 HIV Infections Diseases 0.000 description 5
- 241000700605 Viruses Species 0.000 description 5
- 125000003636 chemical group Chemical group 0.000 description 5
- UIEABCXJWANXFS-UHFFFAOYSA-N 1h-pyrazol-5-ylmethanol Chemical compound OCC=1C=CNN=1 UIEABCXJWANXFS-UHFFFAOYSA-N 0.000 description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 3
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
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- 125000005842 heteroatom Chemical group 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
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- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 2
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/18—One oxygen or sulfur 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
- C07D401/02—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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- AIDS & HIV (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0113524.3A GB0113524D0 (en) | 2001-06-04 | 2001-06-04 | Pyrazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308781B true ZA200308781B (en) | 2005-02-11 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308781A ZA200308781B (en) | 2001-06-04 | 2003-11-11 | Pyrazole derivatives as HIV reverse transcriptase inhibitors. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6538015B1 (enExample) |
| EP (1) | EP1401826B1 (enExample) |
| JP (1) | JP4088249B2 (enExample) |
| KR (1) | KR100627532B1 (enExample) |
| CN (1) | CN1249052C (enExample) |
| AT (1) | ATE357439T1 (enExample) |
| AU (1) | AU2002325221B2 (enExample) |
| BR (1) | BR0210158A (enExample) |
| CA (1) | CA2448058C (enExample) |
| DE (1) | DE60219009T2 (enExample) |
| DK (1) | DK1401826T3 (enExample) |
| ES (1) | ES2282446T3 (enExample) |
| GB (1) | GB0113524D0 (enExample) |
| MX (1) | MXPA03011199A (enExample) |
| PT (1) | PT1401826E (enExample) |
| WO (1) | WO2002100853A1 (enExample) |
| ZA (1) | ZA200308781B (enExample) |
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| TW200423930A (en) * | 2003-02-18 | 2004-11-16 | Hoffmann La Roche | Non-nucleoside reverse transcriptase inhibitors |
| JP4993407B2 (ja) | 2004-08-04 | 2012-08-08 | 大正製薬株式会社 | トリアゾール誘導体 |
| WO2006072833A1 (en) * | 2005-01-06 | 2006-07-13 | Pfizer Limited | Imidazole derivatives as enzyme reverse transcriptase modulators |
| EP1988083B1 (en) | 2006-02-03 | 2014-04-02 | Taisho Pharmaceutical Co., Ltd. | Triazole derivative |
| RU2395499C2 (ru) * | 2006-02-06 | 2010-07-27 | Тайсо Фармасьютикал Ко., Лтд. | Ингибитор связывания сфингозин-1-фосфата |
| PL2057125T3 (pl) | 2006-08-16 | 2011-09-30 | Hoffmann La Roche | Nienukleozydowe inhibitory odwrotnej transkryptazy |
| BRPI0813404A2 (pt) | 2007-06-22 | 2014-12-30 | Hoffmann La Roche | Derivados de uréia e carbamato como inibidores de transcriptase reversa de não-nucleosídeo |
| SI2177512T1 (sl) | 2007-08-01 | 2012-06-29 | Taisho Pharmaceutical Co Ltd | Inhibitor vezave S1P1 |
| RU2495878C2 (ru) | 2007-12-21 | 2013-10-20 | Ф.Хоффманн-Ля Рош Аг | Гетероциклические антивирусные соединения |
| DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
| DE102008015033A1 (de) * | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
| DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
| EP2295038B1 (en) * | 2009-09-11 | 2013-05-29 | AiCuris GmbH & Co. KG | Solid dispersion comprising an anti-HIV agent |
| ES2528646T3 (es) * | 2010-05-20 | 2015-02-11 | Bayer Intellectual Property Gmbh | Procedimiento para la fabricación de 1-alquil-3-difluorometil-5-hidroxipirazoles |
| JP5722891B2 (ja) | 2010-07-15 | 2015-05-27 | 大日本住友製薬株式会社 | ピラゾール化合物 |
| WO2014074628A1 (en) * | 2012-11-08 | 2014-05-15 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Compounds for treating hiv and methods for using the compounds |
| US9925190B2 (en) | 2015-02-16 | 2018-03-27 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecules targeting HIV-1 Nef |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0627423A4 (en) | 1992-01-22 | 1995-02-15 | Nissan Chemical Ind Ltd | SUBSTITUTED PYRAZOLE DERIVATIVES AND BACTERICIDES FOR AGRICULTURE AND GARDENING. |
| US6005109A (en) | 1997-10-30 | 1999-12-21 | Pflizer Inc. | Pyrazoles and pyrazolopyrimidines having CRF antagonistic activity |
| DK0786455T3 (da) | 1994-09-26 | 2004-03-29 | Shionogi & Co | Imidazolderivater |
| US5698495A (en) | 1995-11-15 | 1997-12-16 | Zeneca Limited | Herbicidal substituted pyrazole compounds |
| GB0016787D0 (en) | 2000-07-07 | 2000-08-30 | Pfizer Ltd | Compounds useful in therapy |
| GB0024795D0 (en) | 2000-10-10 | 2000-11-22 | Hoffmann La Roche | Pyrazole derivatives for the treatment of viral diseases |
-
2001
- 2001-06-04 GB GBGB0113524.3A patent/GB0113524D0/en not_active Ceased
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2002
- 2002-05-24 US US10/154,585 patent/US6538015B1/en not_active Expired - Fee Related
- 2002-05-29 JP JP2003503620A patent/JP4088249B2/ja not_active Expired - Fee Related
- 2002-05-29 WO PCT/EP2002/005898 patent/WO2002100853A1/en not_active Ceased
- 2002-05-29 PT PT02758207T patent/PT1401826E/pt unknown
- 2002-05-29 AT AT02758207T patent/ATE357439T1/de not_active IP Right Cessation
- 2002-05-29 KR KR1020037015833A patent/KR100627532B1/ko not_active Expired - Fee Related
- 2002-05-29 BR BR0210158-0A patent/BR0210158A/pt not_active IP Right Cessation
- 2002-05-29 CA CA002448058A patent/CA2448058C/en not_active Expired - Fee Related
- 2002-05-29 CN CNB028111974A patent/CN1249052C/zh not_active Expired - Fee Related
- 2002-05-29 AU AU2002325221A patent/AU2002325221B2/en not_active Ceased
- 2002-05-29 EP EP02758207A patent/EP1401826B1/en not_active Expired - Lifetime
- 2002-05-29 MX MXPA03011199A patent/MXPA03011199A/es active IP Right Grant
- 2002-05-29 DK DK02758207T patent/DK1401826T3/da active
- 2002-05-29 DE DE60219009T patent/DE60219009T2/de not_active Expired - Fee Related
- 2002-05-29 ES ES02758207T patent/ES2282446T3/es not_active Expired - Lifetime
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2003
- 2003-11-11 ZA ZA200308781A patent/ZA200308781B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1401826E (pt) | 2007-06-19 |
| AU2002325221B2 (en) | 2008-07-31 |
| JP4088249B2 (ja) | 2008-05-21 |
| CN1527829A (zh) | 2004-09-08 |
| WO2002100853A1 (en) | 2002-12-19 |
| CN1249052C (zh) | 2006-04-05 |
| MXPA03011199A (es) | 2004-02-26 |
| US6538015B1 (en) | 2003-03-25 |
| DE60219009T2 (de) | 2007-12-13 |
| EP1401826A1 (en) | 2004-03-31 |
| ATE357439T1 (de) | 2007-04-15 |
| JP2004532276A (ja) | 2004-10-21 |
| CA2448058C (en) | 2008-12-23 |
| GB0113524D0 (en) | 2001-07-25 |
| CA2448058A1 (en) | 2002-12-19 |
| DK1401826T3 (da) | 2007-07-30 |
| EP1401826B1 (en) | 2007-03-21 |
| BR0210158A (pt) | 2004-06-08 |
| DE60219009D1 (de) | 2007-05-03 |
| KR20040003050A (ko) | 2004-01-07 |
| KR100627532B1 (ko) | 2006-09-21 |
| ES2282446T3 (es) | 2007-10-16 |
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