RU2381228C2 - Бициклические гетероциклы и их применение в качестве ингибиторов вич интегразы - Google Patents
Бициклические гетероциклы и их применение в качестве ингибиторов вич интегразы Download PDFInfo
- Publication number
- RU2381228C2 RU2381228C2 RU2006146970/04A RU2006146970A RU2381228C2 RU 2381228 C2 RU2381228 C2 RU 2381228C2 RU 2006146970/04 A RU2006146970/04 A RU 2006146970/04A RU 2006146970 A RU2006146970 A RU 2006146970A RU 2381228 C2 RU2381228 C2 RU 2381228C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- oxo
- hydroxy
- tetrahydro
- carboxamide
- Prior art date
Links
- 229940099797 HIV integrase inhibitor Drugs 0.000 title abstract 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 title abstract 2
- 239000003084 hiv integrase inhibitor Substances 0.000 title abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 24
- 239000001257 hydrogen Substances 0.000 claims abstract 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 24
- -1 dioxothiazinyl Chemical group 0.000 claims abstract 23
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract 13
- 150000003839 salts Chemical class 0.000 claims abstract 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract 11
- 150000002367 halogens Chemical group 0.000 claims abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 2
- 230000036436 anti-hiv Effects 0.000 claims abstract 2
- 125000002393 azetidinyl group Chemical group 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000002541 furyl group Chemical group 0.000 claims abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
- 125000001041 indolyl group Chemical group 0.000 claims abstract 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 2
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 2
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract 2
- 125000005429 oxyalkyl group Chemical group 0.000 claims abstract 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 2
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract 2
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 2
- 125000001544 thienyl group Chemical group 0.000 claims abstract 2
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 2
- LDSKYBVNIGKJHA-UHFFFAOYSA-N 2h-1,4-oxazine-2-carboxamide Chemical compound NC(=O)C1OC=CN=C1 LDSKYBVNIGKJHA-UHFFFAOYSA-N 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 4
- JROPBYGZSRBHDV-UHFFFAOYSA-N oxazine-2-carboxamide Chemical compound NC(=O)N1OC=CC=C1 JROPBYGZSRBHDV-UHFFFAOYSA-N 0.000 claims 4
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000004512 1,2,3-thiadiazol-4-yl group Chemical group S1N=NC(=C1)* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- HFHGVIBGEFYIFU-UHFFFAOYSA-N 3h-oxazepine-2-carboxamide Chemical compound NC(=O)N1CC=CC=CO1 HFHGVIBGEFYIFU-UHFFFAOYSA-N 0.000 claims 1
- UCULMFRTTVDHQW-UHFFFAOYSA-N 9,9-diethyl-n-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-3-hydroxy-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CCC1(CC)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1C(=O)NC UCULMFRTTVDHQW-UHFFFAOYSA-N 0.000 claims 1
- HZCDANOFLILNSA-UHFFFAOYSA-N Dimethyl hydrogen phosphite Chemical group COP(=O)OC HZCDANOFLILNSA-UHFFFAOYSA-N 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- XGMAGKLMXYOTEJ-UHFFFAOYSA-N n-[(4-fluoro-2-morpholin-4-ylphenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1CCOCC1 XGMAGKLMXYOTEJ-UHFFFAOYSA-N 0.000 claims 1
- PYYHHGCMPCSNFK-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1 PYYHHGCMPCSNFK-UHFFFAOYSA-N 0.000 claims 1
- LYTKZEQMSYFEPI-UHFFFAOYSA-N n-[[2-(dimethylsulfamoyl)-4-fluorophenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CN(C)S(=O)(=O)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 LYTKZEQMSYFEPI-UHFFFAOYSA-N 0.000 claims 1
- STAJYGBIAZYIRP-UHFFFAOYSA-N n-[[2-(dimethylsulfamoyl)-4-fluorophenyl]methyl]-9,9-diethyl-3-hydroxy-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CCC1(CC)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1S(=O)(=O)N(C)C STAJYGBIAZYIRP-UHFFFAOYSA-N 0.000 claims 1
- YPGPHKYNAXOSJE-UHFFFAOYSA-N n-[[4-fluoro-2-(2-oxopyrrolidin-1-yl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1N1CCCC1=O YPGPHKYNAXOSJE-UHFFFAOYSA-N 0.000 claims 1
- QOZUICSVLJMIDW-UHFFFAOYSA-N n-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CNC(=O)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 QOZUICSVLJMIDW-UHFFFAOYSA-N 0.000 claims 1
- PLWNJEHHXBQCHO-UHFFFAOYSA-N n-[[4-fluoro-2-(methylsulfamoyl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CNS(=O)(=O)C1=CC(F)=CC=C1CNC(=O)C1=C(O)C(=O)N(CCOC2(C)C)C2=N1 PLWNJEHHXBQCHO-UHFFFAOYSA-N 0.000 claims 1
- RQOGKHGPSHFOKR-UHFFFAOYSA-N n-[[4-fluoro-2-(morpholine-4-carbonyl)phenyl]methyl]-3-hydroxy-9,9-dimethyl-4-oxo-6,7-dihydropyrimido[2,1-c][1,4]oxazine-2-carboxamide Chemical compound CC1(C)OCCN(C(C=2O)=O)C1=NC=2C(=O)NCC1=CC=C(F)C=C1C(=O)N1CCOCC1 RQOGKHGPSHFOKR-UHFFFAOYSA-N 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 abstract 1
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 0 CN1C(c(cc(cc2)F)c2Br)=NN=*C1 Chemical compound CN1C(c(cc(cc2)F)c2Br)=NN=*C1 0.000 description 7
- GABSLIXZUPMMAA-ONEGZZNKSA-N C/C=C/c(cc1)cc(-c2nnn[n]2C)c1C#N Chemical compound C/C=C/c(cc1)cc(-c2nnn[n]2C)c1C#N GABSLIXZUPMMAA-ONEGZZNKSA-N 0.000 description 1
- CEXBXIDLUKOAFK-UHFFFAOYSA-N CC(C)(C1=NC(C(NCc(ccc(F)c2)c2-[n]2ncnc2)=O)=C2O)OCCCN1C2=O Chemical compound CC(C)(C1=NC(C(NCc(ccc(F)c2)c2-[n]2ncnc2)=O)=C2O)OCCCN1C2=O CEXBXIDLUKOAFK-UHFFFAOYSA-N 0.000 description 1
- YHWFNVSJZVKCNP-UHFFFAOYSA-N CC(C)(C1=NC(C(NCc(ccc(F)c2)c2S(C)(=O)=O)=O)=C2O)OCCN1C2=O Chemical compound CC(C)(C1=NC(C(NCc(ccc(F)c2)c2S(C)(=O)=O)=O)=C2O)OCCN1C2=O YHWFNVSJZVKCNP-UHFFFAOYSA-N 0.000 description 1
- SWMZNXXXSJJFDV-UHFFFAOYSA-N C[n]1nnnc1-c1c(CN)ccc(F)c1 Chemical compound C[n]1nnnc1-c1c(CN)ccc(F)c1 SWMZNXXXSJJFDV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57551304P | 2004-05-28 | 2004-05-28 | |
| US60/575,513 | 2004-05-28 | ||
| US60337104P | 2004-08-20 | 2004-08-20 | |
| US60/603,371 | 2004-08-20 | ||
| US11/126,891 | 2005-05-11 | ||
| US11/126,891 US7176196B2 (en) | 2004-05-28 | 2005-05-11 | Bicyclic heterocycles as HIV integrase inhibitors |
| PCT/US2005/016473 WO2005118593A1 (en) | 2004-05-28 | 2005-05-12 | Bicyclic heterocycles as hiv integrase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2006146970A RU2006146970A (ru) | 2008-07-10 |
| RU2381228C2 true RU2381228C2 (ru) | 2010-02-10 |
Family
ID=35456854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2006146970/04A RU2381228C2 (ru) | 2004-05-28 | 2005-05-12 | Бициклические гетероциклы и их применение в качестве ингибиторов вич интегразы |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7176196B2 (enExample) |
| EP (1) | EP1749011B1 (enExample) |
| JP (1) | JP4874959B2 (enExample) |
| KR (1) | KR101097623B1 (enExample) |
| AR (1) | AR049124A1 (enExample) |
| AT (1) | ATE412656T1 (enExample) |
| AU (1) | AU2005250356C1 (enExample) |
| BR (1) | BRPI0511623A (enExample) |
| CA (1) | CA2568356C (enExample) |
| CY (1) | CY1110266T1 (enExample) |
| DE (1) | DE602005010690D1 (enExample) |
| DK (1) | DK1749011T3 (enExample) |
| ES (1) | ES2315875T3 (enExample) |
| HR (1) | HRP20090005T3 (enExample) |
| IL (1) | IL179455A (enExample) |
| MX (1) | MXPA06013835A (enExample) |
| NO (1) | NO20065879L (enExample) |
| NZ (1) | NZ551282A (enExample) |
| PE (1) | PE20060242A1 (enExample) |
| PL (1) | PL1749011T3 (enExample) |
| PT (1) | PT1749011E (enExample) |
| RS (1) | RS50700B (enExample) |
| RU (1) | RU2381228C2 (enExample) |
| SI (1) | SI1749011T1 (enExample) |
| TW (1) | TWI366567B (enExample) |
| WO (1) | WO2005118593A1 (enExample) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7115601B2 (en) | 2004-05-18 | 2006-10-03 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| EP1866313A1 (en) * | 2005-03-31 | 2007-12-19 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Hiv integrase inhibitors |
| US7494984B2 (en) * | 2005-08-31 | 2009-02-24 | Bristol-Myers Squibb Company | Substituted imidazo[1,2-a]pyrimidines as HIV viral DNA integrase inhibitors |
| JP5094725B2 (ja) | 2005-10-04 | 2012-12-12 | イステイチユート・デイ・リチエルケ・デイ・ビオロジア・モレコラーレ・ピ・アンジエレツテイ・エツセ・エルレ・エルレ | Ｈｉｖインテグラーゼ阻害剤 |
| US7902182B2 (en) * | 2005-11-16 | 2011-03-08 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2007064316A1 (en) * | 2005-11-30 | 2007-06-07 | Bristol-Myers Squibb Company | Bicyclic heterocycles as hiv integrase inhibitors |
| WO2007064502A1 (en) * | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Forms of n-[(4-fluorophenyl)methyl]-4,6,7,9-tetrahydro-3-hydroxy-9,9-dimethyl-4-oxo-pyrimido[2,1-c][1,4]oxazine-2-carboxamide |
| US20070129379A1 (en) * | 2005-12-01 | 2007-06-07 | Bristol-Myers Squibb Company | Hiv integrase inhibitors |
| US7897593B2 (en) * | 2006-05-30 | 2011-03-01 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| US7893055B2 (en) * | 2006-06-28 | 2011-02-22 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| AU2007275805A1 (en) * | 2006-07-19 | 2008-01-24 | University Of Georgia Research Foundation, Inc. | Pyridinone diketo acids: Inhibitors of HIV replication in combination therapy |
| US7763630B2 (en) * | 2007-06-06 | 2010-07-27 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| US8129398B2 (en) * | 2008-03-19 | 2012-03-06 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| WO2009120841A1 (en) * | 2008-03-27 | 2009-10-01 | Bristol-Myers Squibb Company | Crystalline form of n-[[4-fluoro-2-(5-methyl-1h-1,2,4-triazol-1-yl)phenyl]methyl]-4,6,7,9-tetrahydro-3-hydroxy-9,9-dimethyl-4-oxo-pyrimido[2,1-c][1,4]oxazine-2-carboxamide, sodium salt monohydrate |
| EP2349276B1 (en) * | 2008-10-06 | 2019-11-27 | Merck Sharp & Dohme Corp. | Hiv integrase inhibitors |
| US8143244B2 (en) * | 2009-02-26 | 2012-03-27 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
| ES2446720T3 (es) | 2009-10-13 | 2014-03-10 | Elanco Animal Health Ireland Limited | Inhibidores de la integrasa macrocíclica |
| US8383639B2 (en) * | 2009-10-15 | 2013-02-26 | Bristol-Myers Squibb Company | HIV integrase inhibitors |
| KR20120094098A (ko) | 2009-12-07 | 2012-08-23 | 유니버시티 오브 조지아 리서치 파운데이션, 인코포레이티드 | 피리디논 하이드록시사이클로펜틸 카복사미드: 치료 용도의 ｈｉｖ 인테그라제 억제제 |
| EA032868B1 (ru) | 2010-01-27 | 2019-07-31 | Вайв Хелткер Компани | Комбинация для лечения вич-инфекции |
| RU2567385C2 (ru) | 2010-04-02 | 2015-11-10 | ЯНССЕН Ар ЭНД Ди АЙРЛЭНД | Макроциклические ингибиторы интегразы |
| JP5996532B2 (ja) | 2010-07-15 | 2016-09-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 有害生物防除剤としての新規複素環式化合物 |
| US8791108B2 (en) | 2011-08-18 | 2014-07-29 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| US9089574B2 (en) | 2011-11-30 | 2015-07-28 | Emory University | Antiviral JAK inhibitors useful in treating or preventing retroviral and other viral infections |
| EP2807149A2 (en) * | 2012-01-26 | 2014-12-03 | CRO Consulting Limited | Agents for treating neurodegenerative disorders |
| WO2014099586A1 (en) | 2012-12-17 | 2014-06-26 | Merck Sharp & Dohme Corp. | 4-pyridinonetriazine derivatives as hiv integrase inhibitors |
| EP2986291B1 (en) | 2013-04-16 | 2020-05-27 | Merck Sharp & Dohme Corp. | 4-pyridone derivative compounds and uses thereof as hiv integrase inhibitors |
| ES2656696T3 (es) | 2013-05-17 | 2018-02-28 | Merck Sharp & Dohme Corp. | Compuestos heterocíclicos tricíclicos condensados como inhibidores de la integrasa del VIH |
| US9951079B2 (en) | 2013-06-13 | 2018-04-24 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds as HIV integrase inhibitors |
| MX367057B (es) | 2013-09-27 | 2019-08-02 | Merck Sharp & Dohme | Derivados de quinolizina sustituidos utiles como inhibidores de integrasa del vih. |
| WO2016187788A1 (en) | 2015-05-25 | 2016-12-01 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds useful for treating hiv infection |
| US10548910B2 (en) | 2015-11-17 | 2020-02-04 | Merck Sharp & Dohme Corp. | Amido-substituted pyridotriazine derivatives useful as HIV integrase inhibitors |
| US10544155B2 (en) | 2015-12-15 | 2020-01-28 | Merck Sharp & Dohme Corp. | Spirocyclic quinolizine derivatives useful as HIV integrase inhibitors |
| WO2017113288A1 (en) | 2015-12-31 | 2017-07-06 | Merck Sharp & Dohme Corp. | Fused tricyclic heterocyclic compounds as hiv integrase inhibitors |
| JOP20190130A1 (ar) | 2016-12-02 | 2019-06-02 | Merck Sharp & Dohme | مركبات حلقية غير متجانسة رباعية الحلقات مفيدة كمثبطات إنزيم مدمج لفيروس نقص المناعة البشرية (hiv) |
| AU2017367714B2 (en) | 2016-12-02 | 2020-11-12 | Merck Sharp & Dohme Corp. | Tricyclic heterocycle compounds useful as HIV integrase inhibitors |
| EP3573984A4 (en) | 2017-01-26 | 2020-07-29 | Merck Sharp & Dohme Corp. | USEFUL SUBSTITUTE QUINOLIZINE DERIVATIVES AS HIV INTEGRASE INHIBITORS |
| WO2021050555A1 (en) * | 2019-09-10 | 2021-03-18 | X-Chem, Inc. | Compositions and uses thereof |
| CN113912622B (zh) * | 2020-07-10 | 2023-12-01 | 上海纽思克生物科技有限公司 | 三环嘧啶酮类化合物、其制备方法、其组合物和用途 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU99105117A (ru) * | 1996-08-16 | 2001-01-20 | Шеринг Акциенгезелльшафт | Бициклические производные пиримидина и их применение в качестве антикоагулянтов |
| WO2003035077A1 (en) * | 2001-10-26 | 2003-05-01 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693641A (en) * | 1996-08-16 | 1997-12-02 | Berlex Laboratories Inc. | Bicyclic pyrimidine derivatives and their use as anti-coagulants |
| DE60218511T2 (de) | 2001-10-26 | 2007-10-25 | Istituto Di Richerche Di Biologia Molecolare P. Angeletti S.P.A. | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| US7094783B2 (en) * | 2002-06-26 | 2006-08-22 | Bristol-Myers Squibb Company | Bicyclic pyrimidinones as coagulation cascade inhibitors |
| AU2003292436B2 (en) | 2002-12-27 | 2009-07-30 | Msd Italia S.R.L. | Tetrahydro-4H-pyrido[1,2-A]pyrimidines and related compounds useful as HIV integrase inhibitors |
| AR046938A1 (es) | 2003-12-12 | 2006-01-04 | Merck & Co Inc | Procedimiento para preparar hexahidropirimido[1,2-a]azepin-2-carboxilatos y compuetos similares |
| TW200526635A (en) | 2003-12-22 | 2005-08-16 | Shionogi & Co | Hydroxypyrimidinone derivative having HIV integrase inhibitory activity |
| MX2007006637A (es) | 2004-12-03 | 2007-06-19 | Merck & Co Inc | Uso de atazanavir para mejorar los parametros farmacocineticos de farmacos metabolizados por isoforma 1a1 de udp-glucuronosil- transferasa. |
| EP1866313A1 (en) | 2005-03-31 | 2007-12-19 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Hiv integrase inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU99105117A (ru) * | 1996-08-16 | 2001-01-20 | Шеринг Акциенгезелльшафт | Бициклические производные пиримидина и их применение в качестве антикоагулянтов |
| WO2003035077A1 (en) * | 2001-10-26 | 2003-05-01 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
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