IL192208A - Compounds for use in improving the pharmacokinetics of HIV integrase inhibitors - Google Patents
Compounds for use in improving the pharmacokinetics of HIV integrase inhibitorsInfo
- Publication number
- IL192208A IL192208A IL192208A IL19220808A IL192208A IL 192208 A IL192208 A IL 192208A IL 192208 A IL192208 A IL 192208A IL 19220808 A IL19220808 A IL 19220808A IL 192208 A IL192208 A IL 192208A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- acceptable salt
- pharmaceutically acceptable
- group
- food
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 111
- 229940099797 HIV integrase inhibitor Drugs 0.000 title claims abstract description 16
- 239000003084 hiv integrase inhibitor Substances 0.000 title claims abstract description 16
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims abstract description 139
- 229960000311 ritonavir Drugs 0.000 claims abstract description 139
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 132
- 235000013305 food Nutrition 0.000 claims abstract description 113
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 25
- 108010002459 HIV Integrase Proteins 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims description 68
- 238000011282 treatment Methods 0.000 claims description 48
- 230000001965 increasing effect Effects 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000002850 integrase inhibitor Substances 0.000 claims description 36
- 229940124524 integrase inhibitor Drugs 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 102100034343 Integrase Human genes 0.000 claims description 26
- 108010061833 Integrases Proteins 0.000 claims description 25
- 238000010521 absorption reaction Methods 0.000 claims description 25
- 230000036470 plasma concentration Effects 0.000 claims description 24
- 208000005074 Retroviridae Infections Diseases 0.000 claims description 23
- 241001430294 unidentified retrovirus Species 0.000 claims description 23
- -1 cyano, phenyl Chemical group 0.000 claims description 21
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims description 20
- 229960002555 zidovudine Drugs 0.000 claims description 20
- DTYLXDLAOLOTKT-UHFFFAOYSA-N 1,4-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2CC(C(=O)O)=CNC2=C1 DTYLXDLAOLOTKT-UHFFFAOYSA-N 0.000 claims description 19
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 claims description 4
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- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 4
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- HSBKFSPNDWWPSL-VDTYLAMSSA-N 4-amino-5-fluoro-1-[(2s,5r)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@@H]1C=C[C@H](CO)O1 HSBKFSPNDWWPSL-VDTYLAMSSA-N 0.000 claims description 3
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 claims description 3
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 claims description 3
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- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 3
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Landscapes
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| US75503905P | 2005-12-30 | 2005-12-30 | |
| US75663106P | 2006-01-06 | 2006-01-06 | |
| US76390106P | 2006-02-01 | 2006-02-01 | |
| PCT/US2006/049668 WO2007079260A1 (en) | 2005-12-30 | 2006-12-29 | Methods for improving the pharmacokinetics of hiv integrase inhibitors |
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| IL192208A0 IL192208A0 (en) | 2009-02-11 |
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| EP (2) | EP1976517A1 (OSRAM) |
| JP (1) | JP4676536B2 (OSRAM) |
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| US20090233964A1 (en) * | 2005-12-30 | 2009-09-17 | Gilead Sciences, Inc. | Methods for improving the pharmacokinetics of hiv integrase inhibitors |
| EP2118082B1 (en) | 2007-02-23 | 2014-10-01 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
| CA2692101A1 (en) * | 2007-06-29 | 2009-01-08 | Gilead Sciences, Inc. | Combination of 6-(3-chloro-2-fluorobenzyl)-1-[(2s)-1-hydroxy-3-methylbutan-2-yl]-7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and a compound that inhibits a ugt pathway or ugt metabolism |
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| AP2008004522A0 (en) | 2008-06-30 |
| CA2635468A1 (en) | 2007-07-12 |
| KR20140082858A (ko) | 2014-07-02 |
| JP4676536B2 (ja) | 2011-04-27 |
| WO2007079260A9 (en) | 2007-08-30 |
| JP2009525265A (ja) | 2009-07-09 |
| EA200801619A1 (ru) | 2008-10-30 |
| SG170795A1 (en) | 2011-05-30 |
| CA2847871C (en) | 2016-07-26 |
| KR20160074018A (ko) | 2016-06-27 |
| CA2847871A1 (en) | 2007-07-12 |
| EA201201496A1 (ru) | 2013-07-30 |
| HRP20080313A2 (en) | 2008-11-30 |
| AU2006332664B2 (en) | 2013-03-14 |
| EA018544B1 (ru) | 2013-08-30 |
| EP1976517A1 (en) | 2008-10-08 |
| SG170796A1 (en) | 2011-05-30 |
| CA2635468C (en) | 2016-08-09 |
| NZ569576A (en) | 2011-09-30 |
| IL192208A0 (en) | 2009-02-11 |
| EP2308490A1 (en) | 2011-04-13 |
| AU2006332664A1 (en) | 2007-07-12 |
| AP2702A (en) | 2013-07-23 |
| WO2007079260A1 (en) | 2007-07-12 |
| US20070219243A1 (en) | 2007-09-20 |
| BRPI0620865A2 (pt) | 2011-11-29 |
| CN104069108A (zh) | 2014-10-01 |
| NO20083333L (no) | 2008-09-29 |
| KR20080081358A (ko) | 2008-09-09 |
| KR101524165B1 (ko) | 2015-06-01 |
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