AU2013260005B2 - Solubilized capsule formulation of 1,1-dimethylethyl [(1S)-1-{[(2S,4R)-4-(7-chloro-4methoxyisoquinolin-1-yloxy)-2-({(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}carbamoyl)pyrrolidin-1-yl]carbonyl}-2,2-dimethylpropyl]carbamate - Google Patents
Solubilized capsule formulation of 1,1-dimethylethyl [(1S)-1-{[(2S,4R)-4-(7-chloro-4methoxyisoquinolin-1-yloxy)-2-({(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}carbamoyl)pyrrolidin-1-yl]carbonyl}-2,2-dimethylpropyl]carbamate Download PDFInfo
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- AU2013260005B2 AU2013260005B2 AU2013260005A AU2013260005A AU2013260005B2 AU 2013260005 B2 AU2013260005 B2 AU 2013260005B2 AU 2013260005 A AU2013260005 A AU 2013260005A AU 2013260005 A AU2013260005 A AU 2013260005A AU 2013260005 B2 AU2013260005 B2 AU 2013260005B2
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- JAUGGEIKQIHSMF-UHFFFAOYSA-N dialuminum;dimagnesium;dioxido(oxo)silane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O JAUGGEIKQIHSMF-UHFFFAOYSA-N 0.000 description 1
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- SLVAPEZTBDBAPI-GDLZYMKVSA-N filibuvir Chemical compound CCC1=NC(CC)=CC(CC[C@]2(OC(=O)C(CC3=NN4C(C)=CC(C)=NC4=N3)=C(O)C2)C2CCCC2)=C1 SLVAPEZTBDBAPI-GDLZYMKVSA-N 0.000 description 1
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
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- 239000007902 hard capsule Substances 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 229940057917 medium chain triglycerides Drugs 0.000 description 1
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- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- XMZSTQYSBYEENY-RMKNXTFCSA-N n-[4-[(e)-2-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]ethenyl]phenyl]methanesulfonamide Chemical compound C1=C(N2C(NC(=O)C=C2)=O)C=C(C(C)(C)C)C(OC)=C1\C=C\C1=CC=C(NS(C)(=O)=O)C=C1 XMZSTQYSBYEENY-RMKNXTFCSA-N 0.000 description 1
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- 235000019629 palatability Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
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- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229940050929 polyethylene glycol 3350 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- RYXIBQLRUHDYEE-UHFFFAOYSA-M potassium;5-(cyclohexen-1-yl)-3-[(4-methoxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]thiophene-2-carboxylate Chemical compound [K+].C1CC(OC)CCC1N(C1=C(SC(=C1)C=1CCCCC=1)C([O-])=O)C(=O)C1CCC(C)CC1 RYXIBQLRUHDYEE-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- TTZHDVOVKQGIBA-IAAJYNJHSA-N propan-2-yl (2s)-2-[[[(2r,3r,4r,5r)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]propanoate Chemical compound N1([C@@H]2O[C@@H]([C@H]([C@]2(F)C)O)COP(=O)(N[C@@H](C)C(=O)OC(C)C)OC=2C=CC=CC=2)C=CC(=O)NC1=O TTZHDVOVKQGIBA-IAAJYNJHSA-N 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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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
- 238000009490 roller compaction Methods 0.000 description 1
- FGHMGRXAHIXTBM-TWFJNEQDSA-N s-[2-[[(2r,3r,4r,5r)-5-(2-amino-6-oxo-3h-purin-9-yl)-3,4-dihydroxy-4-methyloxolan-2-yl]methoxy-(benzylamino)phosphoryl]oxyethyl] 3-hydroxy-2,2-dimethylpropanethioate Chemical compound C([C@@H]1[C@H]([C@@](C)(O)[C@H](N2C3=C(C(NC(N)=N3)=O)N=C2)O1)O)OP(=O)(OCCSC(=O)C(C)(CO)C)NCC1=CC=CC=C1 FGHMGRXAHIXTBM-TWFJNEQDSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- DEKOYVOWOVJMPM-RLHIPHHXSA-N setrobuvir Chemical compound N1([C@H]2[C@@H]3CC[C@@H](C3)[C@H]2C(O)=C(C1=O)C=1NC2=CC=C(C=C2S(=O)(=O)N=1)NS(=O)(=O)C)CC1=CC=C(F)C=C1 DEKOYVOWOVJMPM-RLHIPHHXSA-N 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- SSERCMQZZYTNBY-UHFFFAOYSA-M sodium;3-[(4-hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)amino]-5-phenylthiophene-2-carboxylate Chemical compound [Na+].C1CC(C)CCC1C(=O)N(C1=C(SC(=C1)C=1C=CC=CC=1)C([O-])=O)C1CCC(O)CC1 SSERCMQZZYTNBY-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261643454P | 2012-05-07 | 2012-05-07 | |
| US61/643,454 | 2012-05-07 | ||
| PCT/US2013/038770 WO2013169520A1 (en) | 2012-05-07 | 2013-04-30 | Solubilized capsule formulation of 1,1-dimethylethyl [(1s)-1-{[(2s,4r)-4-(7-chloro-4methoxyisoquinolin-1-yloxy)-2-({(1r,2s)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}carbamoyl)pyrrolidin-1-yl]carbonyl}-2,2-dimethylpropyl]carbamate |
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| AU2013260005A1 AU2013260005A1 (en) | 2015-01-15 |
| AU2013260005B2 true AU2013260005B2 (en) | 2017-07-13 |
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| AU2013260005A Ceased AU2013260005B2 (en) | 2012-05-07 | 2013-04-30 | Solubilized capsule formulation of 1,1-dimethylethyl [(1S)-1-{[(2S,4R)-4-(7-chloro-4methoxyisoquinolin-1-yloxy)-2-({(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}carbamoyl)pyrrolidin-1-yl]carbonyl}-2,2-dimethylpropyl]carbamate |
Country Status (33)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104363898A (zh) * | 2012-05-07 | 2015-02-18 | 百时美施贵宝爱尔兰控股公司 | [(1s)-1-{[(2s,4r)-4-(7-氯-4-甲氧基异喹啉-1-基氧基)-2-({(1r,2s)-1-[(环丙基磺酰基)氨甲酰基]-2-乙烯基环丙基}氨甲酰基)吡咯烷-1-基]羰基}-2,2-二甲基丙基]氨基甲酸1,1-二甲基乙基酯的口服固体给药制剂 |
| SI2909205T1 (sl) | 2012-10-19 | 2017-02-28 | Bristol-Myers Squibb Company | 9-metil substituiran heksadekahidrociklopropa(e)pirolo(1,2-A)(1,4)diazaciklopentadecinil karbamat derivati kot nestrukturalni 3 (NS3) proteazni inhibitorji za zdravljenje hepatitis C virusnih infekcij |
| WO2014071007A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| US9598433B2 (en) | 2012-11-02 | 2017-03-21 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014070974A1 (en) | 2012-11-05 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9580463B2 (en) | 2013-03-07 | 2017-02-28 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2019130341A1 (en) * | 2017-12-26 | 2019-07-04 | Hetero Labs Limited | Capsule compositions comprising lopinavir and ritonavir |
| WO2019175253A1 (en) | 2018-03-14 | 2019-09-19 | KaNDy Therapeutics Limited | Novel pharmaceutical formulation comprising dual nk-1/nk-3 receptor antagonists |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1283041A1 (en) * | 1996-11-21 | 2003-02-12 | Abbott Laboratories | Pharmaceutical compositions containing HIV-protease inhibitors |
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| EA006759B1 (ru) * | 2000-10-31 | 2006-04-28 | Бёрингер Ингельхайм Фармасьютиклз, Инк. | Пероральные лекарственные самоэмульгирующиеся композиции ингибиторов протеазы из класса пиранонов |
| US6828301B2 (en) * | 2002-02-07 | 2004-12-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| MY140680A (en) | 2002-05-20 | 2010-01-15 | Bristol Myers Squibb Co | Hepatitis c virus inhibitors |
| WO2010042834A1 (en) * | 2008-10-09 | 2010-04-15 | Anadys Pharmaceuticals, Inc. | A method of inhibiting hepatitis c virus by combination of a 5,6-dihydro-1h-pyridin-2-one and one or more additional antiviral compounds |
| US8252821B2 (en) * | 2009-04-14 | 2012-08-28 | Bristol-Myers Squibb Company | Bioavailable capsule compositions of amorphous alpha-(N-sulfonamido)acetamide compound |
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2013
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- 2013-04-30 CA CA2872765A patent/CA2872765A1/en not_active Abandoned
- 2013-04-30 HR HRP20181583TT patent/HRP20181583T1/hr unknown
- 2013-04-30 JP JP2015511510A patent/JP6276756B2/ja not_active Expired - Fee Related
- 2013-04-30 MX MX2014013220A patent/MX358545B/es active IP Right Grant
- 2013-04-30 WO PCT/US2013/038770 patent/WO2013169520A1/en not_active Ceased
- 2013-04-30 EA EA201492039A patent/EA028749B1/ru not_active IP Right Cessation
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- 2013-04-30 PT PT13722217T patent/PT2846780T/pt unknown
- 2013-04-30 KR KR20147033971A patent/KR20150004921A/ko not_active Ceased
- 2013-04-30 SM SM20180506T patent/SMT201800506T1/it unknown
- 2013-04-30 AU AU2013260005A patent/AU2013260005B2/en not_active Ceased
- 2013-04-30 SG SG11201406964QA patent/SG11201406964QA/en unknown
- 2013-04-30 RS RS20181141A patent/RS57881B1/sr unknown
- 2013-04-30 SI SI201331126T patent/SI2846780T1/sl unknown
- 2013-04-30 EP EP13722217.0A patent/EP2846780B1/en active Active
- 2013-04-30 PE PE2014001988A patent/PE20142439A1/es not_active Application Discontinuation
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- 2013-04-30 CN CN201380023724.1A patent/CN104363899A/zh active Pending
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- 2013-05-06 TW TW102116102A patent/TWI577392B/zh not_active IP Right Cessation
- 2013-05-06 UY UY0001034785A patent/UY34785A/es unknown
- 2013-05-06 AR ARP130101544A patent/AR090954A1/es unknown
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2014
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- 2014-11-03 IL IL235466A patent/IL235466B/en active IP Right Grant
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1283041A1 (en) * | 1996-11-21 | 2003-02-12 | Abbott Laboratories | Pharmaceutical compositions containing HIV-protease inhibitors |
Non-Patent Citations (3)
| Title |
|---|
| ANONYMOUS: "A Multiple Ascending Dose Study of BMS-650032 in HCV Infected Subjects", CLINICALTRIALS.GOV, pages 1 - 3, XP002702909, Retrieved from the Internet <URL:http://clinicaltrials.gov/ct2/show/study/NCT00722358> [retrieved on 20130718] * |
| C Pasquinelle et al, Microbial Agents and Chemotherapy, vol 56, no 4, 1 April 2012, pages 1838-1844 * |
| Cole et al, Advanced Drug Delivery Reviews, vol 60, no 6, 21 December 2007, pages 747-756 * |
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