ZA200108641B - Improved pharmaceutical formulations. - Google Patents
Improved pharmaceutical formulations. Download PDFInfo
- Publication number
- ZA200108641B ZA200108641B ZA200108641A ZA200108641A ZA200108641B ZA 200108641 B ZA200108641 B ZA 200108641B ZA 200108641 A ZA200108641 A ZA 200108641A ZA 200108641 A ZA200108641 A ZA 200108641A ZA 200108641 B ZA200108641 B ZA 200108641B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino
- ritonavir
- weight
- amount
- hydroxy
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 10
- 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 description 84
- 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 description 73
- 229960000311 ritonavir Drugs 0.000 claims description 73
- 150000001875 compounds Chemical class 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 71
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 108010010369 HIV Protease Proteins 0.000 claims description 27
- 230000002401 inhibitory effect Effects 0.000 claims description 26
- 239000007905 soft elastic gelatin capsule Substances 0.000 claims description 18
- 150000004668 long chain fatty acids Chemical class 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 14
- -1 (N-methyl-N- ((2-isopropyl-4- thiazolyl)methyl)amino) carbonyl Chemical group 0.000 claims description 14
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 14
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 14
- 239000005642 Oleic acid Substances 0.000 claims description 14
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 14
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 14
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 14
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 claims description 13
- 239000007903 gelatin capsule Substances 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 10
- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 10
- 229960000884 nelfinavir Drugs 0.000 claims description 10
- 229960001936 indinavir Drugs 0.000 claims description 8
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 8
- 229960001852 saquinavir Drugs 0.000 claims description 8
- 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 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000008180 pharmaceutical surfactant Substances 0.000 claims description 7
- AMPWQTJNJASABL-UHFFFAOYSA-N 1,6-diphenylhexan-1-amine Chemical compound C=1C=CC=CC=1C(N)CCCCCC1=CC=CC=C1 AMPWQTJNJASABL-UHFFFAOYSA-N 0.000 claims description 5
- WBCWVCYZBFONPT-UHFFFAOYSA-N CN(CC=1N=C(SC1)C(C)C)C(=O)NC(CC(CCCC1=CC=CC=C1)O)C1=CC=CC=C1 Chemical compound CN(CC=1N=C(SC1)C(C)C)C(=O)NC(CC(CCCC1=CC=CC=C1)O)C1=CC=CC=C1 WBCWVCYZBFONPT-UHFFFAOYSA-N 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 5
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- XCVGQMUMMDXKCY-WZJLIZBTSA-N (4R,5S,6S,7R)-4,7-dibenzyl-5,6-dihydroxy-1,3-bis[4-(hydroxymethyl)benzyl]-1,3-diazepan-2-one Chemical compound C1=CC(CO)=CC=C1CN1C(=O)N(CC=2C=CC(CO)=CC=2)[C@H](CC=2C=CC=CC=2)[C@H](O)[C@@H](O)[C@H]1CC1=CC=CC=C1 XCVGQMUMMDXKCY-WZJLIZBTSA-N 0.000 claims description 3
- HINZVVDZPLARRP-YSVIXOAZSA-N (4r,5s,6s,7r)-1,3-bis[(3-aminophenyl)methyl]-4,7-dibenzyl-5,6-dihydroxy-1,3-diazepan-2-one;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.NC1=CC=CC(CN2C(N(CC=3C=C(N)C=CC=3)[C@H](CC=3C=CC=CC=3)[C@H](O)[C@@H](O)[C@H]2CC=2C=CC=CC=2)=O)=C1 HINZVVDZPLARRP-YSVIXOAZSA-N 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 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 claims description 2
- 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 3
- ZXNDTHXXZRQCTC-UHFFFAOYSA-N 2-[4-[tert-butylcarbamoyl(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]-2-(quinoline-2-carbonylamino)butanediamide Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)NC(CC(N)=O)(C(N)=O)C(C(O)CN(CC(C)C)C(=O)NC(C)(C)C)CC1=CC=CC=C1 ZXNDTHXXZRQCTC-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- 238000002360 preparation method Methods 0.000 description 16
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- 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)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
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US32582699A | 1999-06-04 | 1999-06-04 |
Publications (1)
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ZA200108641B true ZA200108641B (en) | 2003-01-20 |
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ZA200108641A ZA200108641B (en) | 1999-06-04 | 2001-10-19 | Improved pharmaceutical formulations. |
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EP (2) | EP1183026B1 (sl) |
JP (1) | JP4753511B2 (sl) |
KR (1) | KR100815412B1 (sl) |
CN (2) | CN100418527C (sl) |
AR (2) | AR032586A1 (sl) |
AT (2) | ATE332132T1 (sl) |
AU (1) | AU778198B2 (sl) |
BG (1) | BG65445B1 (sl) |
BR (1) | BR0007294A (sl) |
CA (1) | CA2371109C (sl) |
CL (1) | CL2008003491A1 (sl) |
CO (1) | CO5160323A1 (sl) |
CY (2) | CY1105237T1 (sl) |
CZ (1) | CZ301308B6 (sl) |
DE (2) | DE60029219T2 (sl) |
DK (2) | DK1183026T3 (sl) |
ES (2) | ES2324549T5 (sl) |
HK (1) | HK1045804A1 (sl) |
HU (1) | HU229501B1 (sl) |
IL (3) | IL146025A0 (sl) |
MX (1) | MXPA01012478A (sl) |
MY (1) | MY127908A (sl) |
NO (1) | NO328968B1 (sl) |
NZ (1) | NZ515016A (sl) |
PL (1) | PL197671B1 (sl) |
PT (2) | PT1733725E (sl) |
SA (1) | SA00210237B1 (sl) |
SI (2) | SI1183026T1 (sl) |
SK (2) | SK287185B6 (sl) |
TR (1) | TR200103488T2 (sl) |
TW (1) | TWI244390B (sl) |
WO (1) | WO2000074677A2 (sl) |
ZA (1) | ZA200108641B (sl) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
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MY145265A (en) * | 1998-07-20 | 2012-01-13 | Abbott Lab | Amorphous ritonavir |
JP4753511B2 (ja) * | 1999-06-04 | 2011-08-24 | アボット・ラボラトリーズ | 改良された医薬製剤 |
US7141593B1 (en) | 1999-06-04 | 2006-11-28 | Abbott Laboratories | Pharmaceutical formulations |
DE60028754T2 (de) | 1999-11-12 | 2007-05-31 | Abbott Laboratories, Abbott Park | Feste dispersion mit ritonavir, fenofibrat oder griseofulvin |
JP4769400B2 (ja) * | 2000-01-19 | 2011-09-07 | アボット・ラボラトリーズ | 改良された医薬配合物 |
CA2448438A1 (en) * | 2001-05-25 | 2002-12-05 | Abbott Laboratories | Soft elastic capsules comprising ritonavir and/or lopinavir |
US20050048112A1 (en) | 2003-08-28 | 2005-03-03 | Jorg Breitenbach | Solid pharmaceutical dosage form |
US8025899B2 (en) | 2003-08-28 | 2011-09-27 | Abbott Laboratories | Solid pharmaceutical dosage form |
KR20160074018A (ko) * | 2005-12-30 | 2016-06-27 | 길리애드 사이언시즈, 인코포레이티드 | Hiv 인테그라제 억제제의 약동학을 개선하기 위한 방법 |
AU2015258296B2 (en) * | 2006-07-07 | 2017-08-17 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
AU2007275860C1 (en) | 2006-07-07 | 2014-06-12 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
AU2013204805C1 (en) * | 2006-07-07 | 2017-03-09 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
NO345893B1 (no) * | 2006-07-07 | 2021-09-27 | Gilead Sciences Inc | Modulatorer av farmakokinetikkegenskaper til terapeutika |
AU2015234299B2 (en) * | 2006-07-07 | 2017-03-09 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
WO2008067164A2 (en) | 2006-11-15 | 2008-06-05 | Abbott Laboratories | Solid pharmaceutical dosage formulations |
RS55351B1 (sr) | 2007-02-23 | 2017-03-31 | Gilead Sciences | Modulatori farmakokinetičkih svojstava lekova |
AU2015204378B2 (en) * | 2007-02-23 | 2017-03-09 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
AU2013204817B2 (en) * | 2007-02-23 | 2015-05-07 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
SG183059A1 (en) | 2007-02-23 | 2012-08-30 | Gilead Sciences Inc | Modulators of pharmacokinetic properties of therapeutics |
AU2008275744A1 (en) * | 2007-07-06 | 2009-01-15 | Gilead Sciences, Inc. | Modulators of pharmacokinetic properties of therapeutics |
WO2009088719A1 (en) | 2008-01-04 | 2009-07-16 | Gilead Sciences, Inc. | Inhibitors of cytochrome p450 |
UA108738C2 (uk) * | 2009-04-03 | 2015-06-10 | Спосіб одержання інгібітора цитохром р450 монооксигенази та залучені проміжні сполуки |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
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US5552558A (en) * | 1989-05-23 | 1996-09-03 | Abbott Laboratories | Retroviral protease inhibiting compounds |
GB8927913D0 (en) * | 1989-12-11 | 1990-02-14 | Hoffmann La Roche | Amino acid derivatives |
US5413999A (en) * | 1991-11-08 | 1995-05-09 | Merck & Co., Inc. | HIV protease inhibitors useful for the treatment of AIDS |
IL110752A (en) † | 1993-09-13 | 2000-07-26 | Abbott Lab | Liquid semi-solid or solid pharmaceutical composition for an HIV protease inhibitor |
US5559158A (en) * | 1993-10-01 | 1996-09-24 | Abbott Laboratories | Pharmaceutical composition |
IL111991A (en) † | 1994-01-28 | 2000-07-26 | Abbott Lab | Liquid pharmaceutical composition of HIV protease inhibitors in organic solvent |
EP0788346B9 (en) * | 1994-03-18 | 2007-02-14 | Supernus Pharmaceuticals, Inc. | Emulsified drug delivery systems |
DE4431489A1 (de) * | 1994-09-03 | 1996-03-07 | Heidelberger Baustofftech Gmbh | Schnellhärtende aminosilanvernetzende Silikonmassen |
US5567823A (en) * | 1995-06-06 | 1996-10-22 | Abbott Laboratories | Process for the preparation of an HIV protease inhibiting compound |
US6037157A (en) * | 1995-06-29 | 2000-03-14 | Abbott Laboratories | Method for improving pharmacokinetics |
US5914332A (en) * | 1995-12-13 | 1999-06-22 | Abbott Laboratories | Retroviral protease inhibiting compounds |
CA2238977A1 (en) * | 1995-12-13 | 1997-06-19 | Abbott Laboratories | Retroviral protease inhibiting compounds |
ZA9710071B (en) * | 1996-11-21 | 1998-05-25 | Abbott Lab | Pharmaceutical composition. |
MY145265A (en) * | 1998-07-20 | 2012-01-13 | Abbott Lab | Amorphous ritonavir |
JP4753511B2 (ja) * | 1999-06-04 | 2011-08-24 | アボット・ラボラトリーズ | 改良された医薬製剤 |
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2000
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- 2000-05-25 EP EP06114684A patent/EP1733725B2/en not_active Revoked
- 2000-05-25 AT AT06114684T patent/ATE429224T1/de active
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2001
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2002
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2006
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2007
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2008
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2009
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2011
- 2011-11-29 IL IL216686A patent/IL216686A/en active IP Right Grant
Also Published As
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