JP2006516606A - Ｈｉｖインテグラーゼインヒビター、医薬組成物、およびそれらの使用 - Google Patents
Ｈｉｖインテグラーゼインヒビター、医薬組成物、およびそれらの使用 Download PDFInfo
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- JP2006516606A JP2006516606A JP2006502388A JP2006502388A JP2006516606A JP 2006516606 A JP2006516606 A JP 2006516606A JP 2006502388 A JP2006502388 A JP 2006502388A JP 2006502388 A JP2006502388 A JP 2006502388A JP 2006516606 A JP2006516606 A JP 2006516606A
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- Prior art keywords
- alkyl
- alkynyl
- alkenyl
- independently selected
- compound
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 229940099797 HIV integrase inhibitor Drugs 0.000 title description 3
- 239000003084 hiv integrase inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 246
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 52
- 125000001424 substituent group Chemical group 0.000 claims abstract description 48
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 47
- 150000002367 halogens Chemical class 0.000 claims abstract description 47
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 45
- 125000003118 aryl group Chemical group 0.000 claims abstract description 44
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 36
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 36
- 108010002459 HIV Integrase Proteins 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 29
- 201000010099 disease Diseases 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
- 230000000694 effects Effects 0.000 claims abstract description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 25
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
- 230000001404 mediated effect Effects 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
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- 150000003839 salts Chemical class 0.000 claims description 83
- 108010061833 Integrases Proteins 0.000 claims description 77
- -1 (5-chlorothien-2-yl) methyl Chemical group 0.000 claims description 58
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- 238000000034 method Methods 0.000 claims description 46
- 239000012453 solvate Substances 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
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- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 3
- UKZNDRCGTGQSLU-UHFFFAOYSA-N 9-[(3-chloro-2,6-difluorophenyl)methyl]-n-hydroxy-n-methylpyrido[3,4-b]indole-3-carboxamide Chemical compound C1=NC(C(=O)N(O)C)=CC(C2=CC=CC=C22)=C1N2CC1=C(F)C=CC(Cl)=C1F UKZNDRCGTGQSLU-UHFFFAOYSA-N 0.000 claims description 3
- BXNMCCAUNWEGSF-UHFFFAOYSA-N 9-[(3-chloro-2,6-difluorophenyl)methyl]-n-hydroxypyrido[3,4-b]indole-3-carboxamide Chemical compound C1=NC(C(=O)NO)=CC(C2=CC=CC=C22)=C1N2CC1=C(F)C=CC(Cl)=C1F BXNMCCAUNWEGSF-UHFFFAOYSA-N 0.000 claims description 3
- JBHRILBPDWAKSK-UHFFFAOYSA-N 9-[(3-chloro-2-fluorophenyl)methyl]-n-hydroxypyrido[3,4-b]indole-3-carboxamide Chemical compound C1=NC(C(=O)NO)=CC(C2=CC=CC=C22)=C1N2CC1=CC=CC(Cl)=C1F JBHRILBPDWAKSK-UHFFFAOYSA-N 0.000 claims description 3
- RYZKQKZUMWOKKS-UHFFFAOYSA-N 9-[(4-fluorophenyl)methyl]-n-hydroxy-n-methylpyrido[3,4-b]indole-3-carboxamide Chemical compound C1=NC(C(=O)N(O)C)=CC(C2=CC=CC=C22)=C1N2CC1=CC=C(F)C=C1 RYZKQKZUMWOKKS-UHFFFAOYSA-N 0.000 claims description 3
- ADHFMENDOUEJRK-UHFFFAOYSA-N 9-[(4-fluorophenyl)methyl]-n-hydroxypyrido[3,4-b]indole-3-carboxamide Chemical compound C1=NC(C(=O)NO)=CC(C2=CC=CC=C22)=C1N2CC1=CC=C(F)C=C1 ADHFMENDOUEJRK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- DOZQZHQTEWNLPV-UHFFFAOYSA-N 9-[(2,4-difluorophenyl)methyl]-n-hydroxypyrido[3,4-b]indole-3-carboxamide Chemical compound C1=NC(C(=O)NO)=CC(C2=CC=CC=C22)=C1N2CC1=CC=C(F)C=C1F DOZQZHQTEWNLPV-UHFFFAOYSA-N 0.000 claims description 2
- 125000006287 difluorobenzyl group Chemical group 0.000 claims description 2
- KUTCXBRTPRWGTL-UHFFFAOYSA-N n-benzyl-9-[(3-chloro-2,6-difluorophenyl)methyl]-n-hydroxypyrido[3,4-b]indole-3-carboxamide Chemical compound C=1C(C2=CC=CC=C2N2CC=3C(=C(Cl)C=CC=3F)F)=C2C=NC=1C(=O)N(O)CC1=CC=CC=C1 KUTCXBRTPRWGTL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 65
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- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract 1
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
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- 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 description 1
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- 229960000885 rifabutin Drugs 0.000 description 1
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- 229960001852 saquinavir Drugs 0.000 description 1
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- 238000010512 small scale reaction Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012439 solid excipient Substances 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
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- 229930191512 spiramycin Natural products 0.000 description 1
- 235000019372 spiramycin Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000017960 syncytium formation Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 229960001355 tenofovir disoproxil Drugs 0.000 description 1
- JFVZFKDSXNQEJW-CQSZACIVSA-N tenofovir disoproxil Chemical compound N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N JFVZFKDSXNQEJW-CQSZACIVSA-N 0.000 description 1
- OQHZMGOXOOOFEE-SYQUUIDJSA-N tert-butyl n-[(2s,3r)-3-hydroxy-4-[[(2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-[4-(2-morpholin-4-yl-2-oxoethoxy)phenyl]butyl]amino]-1-phenylbutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@H](O)CNC[C@@H](O)[C@H](CC=1C=CC(OCC(=O)N2CCOCC2)=CC=1)NC(=O)OC(C)(C)C)C1=CC=CC=C1 OQHZMGOXOOOFEE-SYQUUIDJSA-N 0.000 description 1
- KKRYDPVDJYCEER-QEGGNFSNSA-N tert-butyl n-[(2s,3r)-3-hydroxy-4-[[(2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutyl]amino]-1-phenylbutan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)[C@H](O)CNC[C@@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OC(C)(C)C)C1=CC=CC=C1 KKRYDPVDJYCEER-QEGGNFSNSA-N 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- ZFEAMMNVDPDEGE-LGRGJMMZSA-N tifuvirtide Chemical compound C([C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(C)=O)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)C1=CC=C(O)C=C1 ZFEAMMNVDPDEGE-LGRGJMMZSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229950009795 tucaresol Drugs 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 230000036967 uncompetitive effect Effects 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 229940093257 valacyclovir Drugs 0.000 description 1
- 229940100050 virazole Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229960000523 zalcitabine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44322303P | 2003-01-27 | 2003-01-27 | |
| PCT/IB2004/000259 WO2004067531A1 (en) | 2003-01-27 | 2004-01-23 | Hiv-integrase inhibitors, pharmaceutical compositions, and methods for their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006516606A true JP2006516606A (ja) | 2006-07-06 |
| JP2006516606A5 JP2006516606A5 (https=) | 2006-10-19 |
Family
ID=32825309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006502388A Abandoned JP2006516606A (ja) | 2003-01-27 | 2004-01-23 | Ｈｉｖインテグラーゼインヒビター、医薬組成物、およびそれらの使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7001912B2 (https=) |
| EP (1) | EP1590349A1 (https=) |
| JP (1) | JP2006516606A (https=) |
| BR (1) | BRPI0407052A (https=) |
| CA (1) | CA2513141A1 (https=) |
| MX (1) | MXPA05007563A (https=) |
| WO (1) | WO2004067531A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006526580A (ja) * | 2003-06-02 | 2006-11-24 | 新疆華世丹薬物研究有限責任公司 | ハルミン誘導体、これらの調製において使用する中間体、調製過程およびこれらの使用 |
| JP2007534738A (ja) * | 2004-04-26 | 2007-11-29 | ファイザー・インク | Ｈｉｖインテグラーゼ酵素の阻害剤 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PA8586801A1 (es) | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| WO2004067531A1 (en) | 2003-01-27 | 2004-08-12 | Pfizer Inc. | Hiv-integrase inhibitors, pharmaceutical compositions, and methods for their use |
| EP1873155A1 (en) * | 2004-04-26 | 2008-01-02 | Pfizer Inc. | Inhibitors of the HIV integrase enzyme |
| CA2564356A1 (en) | 2004-04-26 | 2005-11-03 | Pfizer Inc. | Pyrrolopyridine derivatives and their use as hiv-integrase inhibitors |
| US7538112B2 (en) * | 2004-05-07 | 2009-05-26 | Merck & Co., Inc. | HIV integrase inhibitors |
| JP2009511463A (ja) * | 2005-10-07 | 2009-03-19 | ファイザー・プロダクツ・インク | Ｈｉｖインテグラーゼ酵素の阻害剤 |
| EP1976517A1 (en) * | 2005-12-30 | 2008-10-08 | Gilead Sciences, Inc. | Methods for improving the pharmacokinetics of hiv integrase inhibitors |
| CN105481788A (zh) * | 2006-10-28 | 2016-04-13 | 梅特希尔基因公司 | 组蛋白脱乙酰酶抑制剂 |
| US20100256379A1 (en) * | 2007-10-26 | 2010-10-07 | Kagoshima University | Anti-viral agent containing heterocyclic aromatic compound as active ingredient |
| US9151055B2 (en) | 2009-02-25 | 2015-10-06 | Owens Corning Intellectual Capital, Llc | Hip and ridge roofing material |
| US8580294B2 (en) | 2010-10-19 | 2013-11-12 | International Partnership For Microbicides | Platinum-catalyzed intravaginal rings |
| US10137031B2 (en) | 2013-11-14 | 2018-11-27 | International Partnership For Microbicides, Inc. | Combination therapy intravaginal rings |
| CN109369510A (zh) * | 2018-10-31 | 2019-02-22 | 云南大学 | 具有抗hiv活性的双甲氧基取代咔唑类化合物制备及用途 |
| AU2021312027A1 (en) * | 2020-07-23 | 2023-01-05 | Cancer Research Technology Ltd. | Tricyclic heterocycles |
| CN119431371A (zh) * | 2024-10-22 | 2025-02-14 | 沈阳药科大学 | 一种β-卡波林3,6,9-位修饰衍生物及其制备方法和用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ194747A (en) * | 1979-08-29 | 1988-11-29 | Schering Ag | 9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives |
| GB8720125D0 (en) * | 1987-08-26 | 1987-09-30 | Roussel Lab Ltd | Chemical compounds |
| US6057297A (en) * | 1996-08-06 | 2000-05-02 | Polifarma S.P.A. | Inhibitor compounds of zinc-dependent metalloproteinases associated with pathological conditions, and therapeutic use thereof |
| FR2754262B1 (fr) * | 1996-10-08 | 1998-10-30 | Synthelabo | Derives de 1h-pyrido[3,4-b]indole-4-carboxamide, leur preparation et leur application en therapeutique |
| HUP0302962A2 (hu) | 1998-06-12 | 2003-12-29 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A.S. | Béta-karbolinszármazékok, ezeket a vegyületeket tartalmazó gyógyászati készítmények és a vegyületek alkalmazása |
| EP1209158A1 (en) * | 2000-11-18 | 2002-05-29 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines |
| JP3616628B2 (ja) | 2001-03-01 | 2005-02-02 | 塩野義製薬株式会社 | Ｈｉｖインテグラーゼ阻害活性を有する含窒素芳香族複素環化合物 |
| JP4176477B2 (ja) | 2001-03-01 | 2008-11-05 | 塩野義製薬株式会社 | Ｈｉｖインテグラーゼ阻害活性を有する含窒素芳香族複素環誘導体 |
| JP2003171381A (ja) | 2001-09-25 | 2003-06-20 | Takeda Chem Ind Ltd | エントリー阻害剤 |
| JP2003119137A (ja) | 2001-10-10 | 2003-04-23 | Japan Tobacco Inc | Ｈｉｖ阻害剤 |
| JP2005508968A (ja) * | 2001-10-19 | 2005-04-07 | トランス テック ファーマ，インコーポレイテッド | ＰＴＰ阻害剤としてのβ−カルボリン誘導体 |
| ATE355064T1 (de) | 2001-10-26 | 2006-03-15 | Angeletti P Ist Richerche Bio | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| AU2002349675A1 (en) | 2001-12-05 | 2003-06-17 | Shionogi And Co., Ltd. | Derivative having hiv integrase inhibitory activity |
| CA2469592C (en) | 2001-12-12 | 2005-08-23 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| EP1467970B1 (en) | 2002-01-17 | 2007-08-22 | Merck & Co., Inc. | Hydroxynaphthyridinone carboxamides useful as hiv integrase inhibitors |
| ATE409187T1 (de) | 2002-03-15 | 2008-10-15 | Merck & Co Inc | N-(substituierte benzyl)-8-hydroxy-1,6- naphthyridin-7- carbonsäureamide als hiv- integrase-hemmer |
| PA8586801A1 (es) | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| WO2004067531A1 (en) | 2003-01-27 | 2004-08-12 | Pfizer Inc. | Hiv-integrase inhibitors, pharmaceutical compositions, and methods for their use |
-
2004
- 2004-01-23 WO PCT/IB2004/000259 patent/WO2004067531A1/en not_active Ceased
- 2004-01-23 JP JP2006502388A patent/JP2006516606A/ja not_active Abandoned
- 2004-01-23 BR BR0407052-6A patent/BRPI0407052A/pt not_active IP Right Cessation
- 2004-01-23 CA CA002513141A patent/CA2513141A1/en not_active Abandoned
- 2004-01-23 EP EP04704681A patent/EP1590349A1/en not_active Withdrawn
- 2004-01-23 MX MXPA05007563A patent/MXPA05007563A/es unknown
- 2004-01-26 US US10/765,227 patent/US7001912B2/en not_active Expired - Fee Related
-
2005
- 2005-10-14 US US11/251,344 patent/US7138408B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006526580A (ja) * | 2003-06-02 | 2006-11-24 | 新疆華世丹薬物研究有限責任公司 | ハルミン誘導体、これらの調製において使用する中間体、調製過程およびこれらの使用 |
| JP2007534738A (ja) * | 2004-04-26 | 2007-11-29 | ファイザー・インク | Ｈｉｖインテグラーゼ酵素の阻害剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20050165040A1 (en) | 2005-07-28 |
| US20060122211A1 (en) | 2006-06-08 |
| BRPI0407052A (pt) | 2006-01-17 |
| CA2513141A1 (en) | 2004-08-12 |
| US7138408B2 (en) | 2006-11-21 |
| MXPA05007563A (es) | 2005-09-21 |
| US7001912B2 (en) | 2006-02-21 |
| WO2004067531A1 (en) | 2004-08-12 |
| EP1590349A1 (en) | 2005-11-02 |
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