NO329676B1 - Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat - Google Patents

Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat Download PDF

Info

Publication number: NO329676B1
Authority: NO; Norway
Prior art keywords: compound; formula; water; producing; solvent
Prior art date: 1998-07-18

Application number

NO20010282A

Other languages

English (en)

Norwegian (no)

Other versions

NO20010282L (no

NO20010282D0 (no

Inventor

Andrew David Searle

Hardev Singh

Ian Gordon Armitage

Original Assignee

Glaxo Group Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-07-18

Filing date

2001-01-17

Publication date

2010-11-29

2001-01-17 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2001-01-17 Publication of NO20010282D0 publication Critical patent/NO20010282D0/no

2001-03-07 Publication of NO20010282L publication Critical patent/NO20010282L/no

2010-11-29 Publication of NO329676B1 publication Critical patent/NO329676B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 11
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-1 (4-aminophenyl) sulfonyl Chemical group 0.000 title description 11
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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 description 1
239000003701 inert diluent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
KELNNWMENBUHNS-NSHDSACASA-N isopropyl (2s)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxaline-1(2h)-carboxylate Chemical compound FC1=CC=C2NC(=O)[C@H](CC)N(C(=O)OC(C)C)C2=C1 KELNNWMENBUHNS-NSHDSACASA-N 0.000 description 1
229960001627 lamivudine Drugs 0.000 description 1
239000008141 laxative Substances 0.000 description 1
230000002475 laxative effect Effects 0.000 description 1
CJPLEFFCVDQQFZ-UHFFFAOYSA-N loviride Chemical compound CC(=O)C1=CC=C(C)C=C1NC(C(N)=O)C1=C(Cl)C=CC=C1Cl CJPLEFFCVDQQFZ-UHFFFAOYSA-N 0.000 description 1
229950006243 loviride Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
229960000884 nelfinavir Drugs 0.000 description 1
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 description 1
230000000926 neurological effect Effects 0.000 description 1
229960000689 nevirapine Drugs 0.000 description 1
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 1
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000003305 oral gavage Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical class C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
229960000311 ritonavir Drugs 0.000 description 1
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 description 1
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
239000002002 slurry Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000006068 taste-masking agent Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000006514 viral protein processing Effects 0.000 description 1
229960002555 zidovudine Drugs 0.000 description 1
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 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Virology (AREA)
Molecular Biology (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Biochemistry (AREA)
Immunology (AREA)
Epidemiology (AREA)
Tropical Medicine & Parasitology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
AIDS & HIV (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO20010282A 1998-07-18 2001-01-17 Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat NO329676B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9815567.4A GB9815567D0 (en)	1998-07-18	1998-07-18	Antiviral compound
PCT/EP1999/004991 WO2000004033A1 (en)	1998-07-18	1999-07-15	Calcium (3s) tetrahydro-3-furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino] -1-benzyl-2- (phosphonooxy) propylcarbamate

Publications (3)

Publication Number	Publication Date
NO20010282D0 NO20010282D0 (no)	2001-01-17
NO20010282L NO20010282L (no)	2001-03-07
NO329676B1 true NO329676B1 (no)	2010-11-29

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ID=10835689

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20010282A NO329676B1 (no)	1998-07-18	2001-01-17	Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat

Country Status (47)

Country	Link
US (3)	US6514953B1 (pl)
EP (2)	EP1098898B1 (pl)
JP (1)	JP3437553B2 (pl)
KR (1)	KR100694721B1 (pl)
CN (1)	CN1188422C (pl)
AP (1)	AP2001002039A0 (pl)
AR (1)	AR019388A1 (pl)
AT (1)	ATE229964T1 (pl)
AU (1)	AU766056B2 (pl)
BG (1)	BG105253A (pl)
BR (1)	BRPI9912156B8 (pl)
CA (1)	CA2337857C (pl)
CO (1)	CO5090836A1 (pl)
CZ (1)	CZ300447B6 (pl)
DE (1)	DE69904600T2 (pl)
DK (1)	DK1098898T3 (pl)
DZ (1)	DZ2845A1 (pl)
EA (1)	EA003191B1 (pl)
EE (1)	EE200100038A (pl)
ES (1)	ES2189450T3 (pl)
GB (1)	GB9815567D0 (pl)
GC (1)	GC0000105A (pl)
GE (1)	GEP20033030B (pl)
GT (1)	GT199900111A (pl)
HR (1)	HRP20010046A2 (pl)
HU (1)	HU229700B1 (pl)
ID (1)	ID28070A (pl)
IL (1)	IL140824A (pl)
IS (1)	IS5808A (pl)
JO (1)	JO2114B1 (pl)
MA (1)	MA26660A1 (pl)
MY (1)	MY122323A (pl)
NO (1)	NO329676B1 (pl)
NZ (1)	NZ509291A (pl)
OA (1)	OA11706A (pl)
PA (1)	PA8477801A1 (pl)
PE (1)	PE20000869A1 (pl)
PL (1)	PL195736B1 (pl)
PT (1)	PT1098898E (pl)
SK (1)	SK285311B6 (pl)
SV (1)	SV1999000096A (pl)
TN (1)	TNSN99145A1 (pl)
TR (1)	TR200100111T2 (pl)
TW (1)	TWI245770B (pl)
WO (1)	WO2000004033A1 (pl)
YU (1)	YU3401A (pl)
ZA (1)	ZA200100417B (pl)

Families Citing this family (57)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9914821D0 (en) *	1999-06-24	1999-08-25	Glaxo Group Ltd	Compounds
EP1222192B8 (en) *	1999-10-06	2008-10-01	Tibotec Pharmaceuticals Ltd.	Hexahydrofuro¬2,3-b furan-3-yl-n- 3-¬(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino -1-benzyl-2-hydroxypropyl carbamate as retroviral protease inhibitor
ATE285821T1 (de) *	1999-10-08	2005-01-15	Affinium Pharm Inc	Fab i inhibitoren
CA2444597A1 (en) *	2001-04-06	2002-10-06	Affinium Pharmaceuticals, Inc.	Fab i inhibitors
AU2003231765B9 (en)	2002-04-26	2010-01-28	Gilead Sciences, Inc.	Cellular accumulation of phosphonate analogs of HIV protease inhibitor compounds and the compounds as such
EP1575951B1 (en)	2002-12-06	2014-06-25	Debiopharm International SA	Heterocyclic compounds, methods of making them and their use in therapy
DE602004016831D1 (de)	2003-03-17	2008-11-13	Affinium Pharm Inc	Pharmazeutische zusammensetzungen inhibitoren von fab i und weitere antibiotika enthaltend
MXPA05011296A (es)	2003-04-25	2006-01-24	Gilead Sciences Inc	Conjugados de fosfonato inhibidores de la cinasa.
EP2359833A1 (en)	2003-04-25	2011-08-24	Gilead Sciences, Inc.	Antiviral phosphonate analogs
US7300924B2 (en)	2003-04-25	2007-11-27	Gilead Sciences, Inc.	Anti-infective phosphonate analogs
WO2004096287A2 (en)	2003-04-25	2004-11-11	Gilead Sciences, Inc.	Inosine monophosphate dehydrogenase inhibitory phosphonate compounds
US7452901B2 (en)	2003-04-25	2008-11-18	Gilead Sciences, Inc.	Anti-cancer phosphonate analogs
US7273716B2 (en)	2003-04-25	2007-09-25	Gilead Sciences, Inc.	Methods and compositions for identifying therapeutic compounds with GS-7340 ester hydrolase
WO2005002626A2 (en)	2003-04-25	2005-01-13	Gilead Sciences, Inc.	Therapeutic phosphonate compounds
US7432261B2 (en)	2003-04-25	2008-10-07	Gilead Sciences, Inc.	Anti-inflammatory phosphonate compounds
US7470724B2 (en)	2003-04-25	2008-12-30	Gilead Sciences, Inc.	Phosphonate compounds having immuno-modulatory activity
US7407965B2 (en)	2003-04-25	2008-08-05	Gilead Sciences, Inc.	Phosphonate analogs for treating metabolic diseases
US20080234288A1 (en) *	2003-09-30	2008-09-25	Kenneth Alan Simmen	Hcv Inhibiting Sulfonamides
WO2005044308A1 (en)	2003-10-24	2005-05-19	Gilead Sciences, Inc.	Phosphonate analogs of antimetabolites
US7427624B2 (en)	2003-10-24	2008-09-23	Gilead Sciences, Inc.	Purine nucleoside phosphorylase inhibitory phosphonate compounds
WO2005063751A1 (en)	2003-12-22	2005-07-14	Gilead Sciences, Inc.	4’-substituted carbovir-and abacavir-derivatives as well as related compounds with hiv and hcv antiviral activity
EP2848614A3 (en)	2004-06-04	2015-07-29	Debiopharm International SA	Acrylamide derivatives as antibiotic agents
ME03423B (me)	2004-07-27	2020-01-20	Gilead Sciences Inc	Fosfonatni analozi jedinjenja hiv inhibitora
SG158073A1 (en)	2004-11-26	2010-01-29	Ucl Business Plc	Compositions comprising ornithine and phenylacetate or phenylbutyrate for treating hepatic encephalopathy
EP1973902A2 (en) *	2005-12-05	2008-10-01	Affinium Pharmaceuticals, Inc.	3-heterocyclylacrylamide compounds as fabi inhibitors and antibacterial agents
EP2687533B1 (en)	2006-07-20	2017-07-19	Debiopharm International SA	Acrylamide derivatives as FAB I inhibitors
WO2008098374A1 (en)	2007-02-16	2008-08-21	Affinium Pharmaceuticals, Inc.	Salts, prodrugs and polymorphs of fab i inhibitors
CN101631568B (zh)	2007-03-12	2012-08-22	尼克塔治疗公司	低聚物-蛋白酶抑制剂偶联物
US9095620B2 (en) *	2008-03-12	2015-08-04	Nektar Therapeutics	Reagents
UA103329C2 (ru)	2008-07-08	2013-10-10	Гилиад Сайенсиз, Инк.	Соли соединений-ингибиторов вич
CA2757373C (en)	2009-04-03	2018-05-08	Ocera Therapeutics, Inc.	L-ornithine phenyl acetate and methods of making thereof
WO2010134045A1 (en) *	2009-05-20	2010-11-25	Ranbaxy Laboratories Limited	Amorphous fosamprenavir calcium
EA201691430A1 (ru)	2009-06-08	2017-02-28	ЮСиЭл БИЗНЕС ПиЭлСи	Лечение портальной гипертензии и восстановление функции печени с помощью l-орнитинфенилацетата
JP2012530069A (ja)	2009-06-12	2012-11-29	ネクターセラピューティックス	プロテアーゼ阻害剤、水溶性非ペプチドオリゴマーおよび親油性部分を含む共有結合体
WO2011001383A1 (en) *	2009-06-30	2011-01-06	Ranbaxy Laboratories Limited	Crystalline form of fosamprenavir calcium
US9085592B2 (en)	2009-09-16	2015-07-21	Ranbaxy Laboratories Limited	Process for the preparation of fosamprenavir calcium
US20110165202A1 (en) *	2010-01-07	2011-07-07	Pliva Hrvatska D.O.O.	Solid state forms of fosamprenavir calcium salt and processes for preparation thereof
PE20121524A1 (es)	2010-01-27	2012-12-03	Viiv Healthcare Co	Combinaciones de compuestos que comprenden inhibidores de la integrasa de vih y otros agentes terapeuticos
US20110224443A1 (en) *	2010-03-15	2011-09-15	Venkata Naga Brahmeshwara Rao Mandava	Preparation of fosamprenavir calcium
WO2011114212A1 (en)	2010-03-19	2011-09-22	Lupin Limited	Ammonium, calcium and tris salts of fosamprenavir
US20130211108A1 (en) *	2010-06-18	2013-08-15	Mylan Laboratories Ltd	Novel process for the preparation of (3s)-tetrahydrofuran-3-yl (is, 2r)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-(phosphonooxy) propylcarbamate and its pharmaceutically acceptable salts
US8877947B2 (en)	2010-09-10	2014-11-04	Lupin Limited	Process for preparation of substantially pure fosamprenavir calcium and its intermediates
MX360062B (es)	2010-10-06	2018-10-22	Ocera Therapeutics Inc	Metodos de elaboracion de fenilacetato de l-ornitina.
CN102453054B (zh) *	2010-10-29	2015-06-10	浙江九洲药业股份有限公司	一种福沙那韦衍生物的制备方法及相关中间体
CN102453053B (zh) *	2010-10-29	2014-11-26	浙江九洲药业股份有限公司	一种福沙那韦钙晶体及其制备方法
WO2012085625A1 (en)	2010-12-21	2012-06-28	Lupin Limited	Process for the preparation of fosamprenavir calcium and intermediate used in its preparation
JP2014513044A (ja) *	2011-02-10	2014-05-29	マイランラボラトリーズリミテッド	ホスアンプレナビルカルシウム結晶およびその調製方法
WO2013011485A1 (en)	2011-07-20	2013-01-24	Ranbaxy Laboratories Limited	Process for the preparation of sulfonamides useful as retroviral protease inhibitors
IN2012DE00082A (pl)	2012-01-10	2015-05-01	Council Scient Ind Res
SI2861608T1 (sl)	2012-06-19	2019-08-30	Debiopharm International Sa	Derivati predzdravila (E)-N-metil-N-((3-metilbenzofuran-2-IL)metil)- 3-(7-okso-5,6,7,8-tetrahidro-1 ,8-nafthiridin-3-il)akrilamid
US10039735B2 (en)	2014-11-24	2018-08-07	Ucl Business Plc	Treatment of diseases associated with hepatic stellate cell activation using ammonia-lowering therapies
EP3337473A4 (en)	2015-08-18	2019-04-17	Ocera Therapeutics, Inc.	TREATMENT AND PREVENTION OF MUSCLE WOUND BY L-ORNITHIN IN COMBINATION WITH AT LEAST ONE PHENYL ACETATE AND PHENYL BUTYRATE
BR122023021456A2 (pt)	2016-02-26	2024-02-20	Debiopharm International S.A.	Uso de di-hidrogeno fosfato de {6- [(e)-3-{metil[(3-metil-1-benfofuran-2- iol)metil]amino)-3- oxopro-1-en-1-il]-2-oxo-3,4-di-hidro-1,8-naftiridin-1(2h)- il}metila para tratamento de osteomielite do pé diabético e composição farmacêutica
WO2018208677A1 (en)	2017-05-11	2018-11-15	Ocera Therapeutics, Inc.	Processes of making l-ornithine phenylacetate
SI3661937T1 (sl)	2017-08-01	2021-11-30	Gilead Sciences, Inc.	Kristalinične oblike etil((S)-((((2R,5R)-5-(6-amino-9H-purin-9-IL)-4- fluoro-2,5-dihidrofuran-2-IL)oksi)metil)(fenoksi)fosforil)-L-alaninata (GS-9131) za zdravljenje virusnih okužb
LT3923914T (lt)	2019-02-14	2023-07-25	Debiopharm International S.A.	Afabicino kompozicija, jos gamybos būdas
CN113939306B (zh)	2019-06-14	2024-07-19	德彪药业国际股份公司	用于治疗涉及生物膜的细菌感染的药物及其用途

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2698826A (en) *	1951-02-13	1955-01-04	Merco Centrifugal Co	Alcohol manufacturing process
US3437267A (en) *	1966-03-24	1969-04-08	Alfa Laval Ab	Centrifuge
JPH0244315B2 (ja) *	1982-06-14	1990-10-03	Microbial Chem Res Found	Supagarinn155hosufueetooyobisonoseizoho
US5723490A (en) *	1992-09-08	1998-03-03	Vertex Pharmaceuticals Incorporated	THF-containing sulfonamide inhibitors of aspartyl protease
UA49803C2 (uk) *	1994-06-03	2002-10-15	Дж.Д. Сьорль Енд Ко	Спосіб лікування ретровірусних інфекцій
US6436989B1 (en) *	1997-12-24	2002-08-20	Vertex Pharmaceuticals, Incorporated	Prodrugs of aspartyl protease inhibitors
WO1999033792A2 (en) *	1997-12-24	1999-07-08	Vertex Pharmaceuticals Incorporated	Prodrugs os aspartyl protease inhibitors
EE200000386A (et) *	1997-12-24	2001-12-17	Vertex Pharmaceuticals Incorporated	Aspartüülproteaasi inhibiitorite eelravimid
GB9812189D0 (en) *	1998-06-05	1998-08-05	Glaxo Group Ltd	Methods and compositions for increasing penetration of HIV protease inhibitors
AU6329599A (en) *	1998-09-28	2000-04-17	Glaxo Group Limited	Antiviral combinations comprising (s)-2-ethyl -7-fluoro -3-oxo-3, 4-dihydro -2h-quinoxaline -1-carboxylic acid isopropyl ester
CN1154491C (zh) *	1998-11-04	2004-06-23	法玛西雅厄普约翰美国公司	用于改善替普拉那维的药物动力学的方法
CZ20002364A3 (cs) *	1998-12-23	2000-11-15	Vertex Pharmaceuticals Incorporated	Deriváty sulfonamidů a farmaceutický prostředek, který je obsahuje
GB9914821D0 (en) *	1999-06-24	1999-08-25	Glaxo Group Ltd	Compounds
WO2001038332A1 (en) *	1999-11-24	2001-05-31	Merck & Co., Inc.	Gamma-hydroxy-2-(fluoroalkylaminocarbonyl)-1-piperazinepentanamides as hiv protease inhibitors

1998
- 1998-07-18 GB GBGB9815567.4A patent/GB9815567D0/en not_active Ceased
1999
- 1999-07-14 GC GCP1999203 patent/GC0000105A/xx active
- 1999-07-14 AR ARP990103446A patent/AR019388A1/es not_active Application Discontinuation
- 1999-07-14 DZ DZ990145A patent/DZ2845A1/xx active
- 1999-07-15 CN CNB998108383A patent/CN1188422C/zh not_active Expired - Lifetime
- 1999-07-15 WO PCT/EP1999/004991 patent/WO2000004033A1/en not_active Ceased
- 1999-07-15 JO JO19992114A patent/JO2114B1/en active
- 1999-07-15 DE DE69904600T patent/DE69904600T2/de not_active Expired - Lifetime
- 1999-07-15 EE EEP200100038A patent/EE200100038A/xx unknown
- 1999-07-15 TN TNTNSN99145A patent/TNSN99145A1/fr unknown
- 1999-07-15 KR KR1020017000740A patent/KR100694721B1/ko not_active Expired - Lifetime
- 1999-07-15 CO CO99044882A patent/CO5090836A1/es unknown
- 1999-07-15 GE GEAP19995716A patent/GEP20033030B/en unknown
- 1999-07-15 SK SK76-2001A patent/SK285311B6/sk not_active IP Right Cessation
- 1999-07-15 DK DK99934698T patent/DK1098898T3/da active
- 1999-07-15 MY MYPI99002983A patent/MY122323A/en unknown
- 1999-07-15 EP EP99934698A patent/EP1098898B1/en not_active Expired - Lifetime
- 1999-07-15 CZ CZ20010219A patent/CZ300447B6/cs not_active IP Right Cessation
- 1999-07-15 MA MA25684A patent/MA26660A1/fr unknown
- 1999-07-15 EA EA200100053A patent/EA003191B1/ru not_active IP Right Cessation
- 1999-07-15 YU YU3401A patent/YU3401A/sh unknown
- 1999-07-15 CA CA2337857A patent/CA2337857C/en not_active Expired - Lifetime
- 1999-07-15 SV SV1999000096A patent/SV1999000096A/es not_active Application Discontinuation
- 1999-07-15 PE PE1999000714A patent/PE20000869A1/es not_active Application Discontinuation
- 1999-07-15 AU AU50379/99A patent/AU766056B2/en not_active Expired
- 1999-07-15 ES ES99934698T patent/ES2189450T3/es not_active Expired - Lifetime
- 1999-07-15 JP JP2000560139A patent/JP3437553B2/ja not_active Expired - Lifetime
- 1999-07-15 BR BRPI9912156A patent/BRPI9912156B8/pt not_active IP Right Cessation
- 1999-07-15 HU HU0103432A patent/HU229700B1/hu unknown
- 1999-07-15 IL IL14082499A patent/IL140824A/en not_active IP Right Cessation
- 1999-07-15 PL PL99345620A patent/PL195736B1/pl unknown
- 1999-07-15 TR TR2001/00111T patent/TR200100111T2/xx unknown
- 1999-07-15 AP APAP/P/2001/002039A patent/AP2001002039A0/en unknown
- 1999-07-15 HR HR20010046A patent/HRP20010046A2/hr not_active Application Discontinuation
- 1999-07-15 US US09/744,051 patent/US6514953B1/en not_active Expired - Lifetime
- 1999-07-15 PT PT99934698T patent/PT1098898E/pt unknown
- 1999-07-15 OA OA1200100016A patent/OA11706A/fr unknown
- 1999-07-15 GT GT199900111A patent/GT199900111A/es unknown
- 1999-07-15 NZ NZ509291A patent/NZ509291A/en not_active IP Right Cessation
- 1999-07-15 EP EP02013136A patent/EP1240903A3/en not_active Withdrawn
- 1999-07-15 AT AT99934698T patent/ATE229964T1/de active
- 1999-07-15 ID IDW20010145A patent/ID28070A/id unknown
- 1999-07-16 PA PA19998477801A patent/PA8477801A1/es unknown
- 1999-08-06 TW TW088113428A patent/TWI245770B/zh not_active IP Right Cessation
2001
- 2001-01-12 IS IS5808A patent/IS5808A/is unknown
- 2001-01-15 ZA ZA200100417A patent/ZA200100417B/en unknown
- 2001-01-17 NO NO20010282A patent/NO329676B1/no not_active IP Right Cessation
- 2001-02-14 BG BG105253A patent/BG105253A/xx unknown
2002
- 2002-11-25 US US10/303,366 patent/US20030096795A1/en not_active Abandoned
- 2002-11-25 US US10/303,213 patent/US20030100537A1/en not_active Abandoned

Also Published As

Publication number	Publication date
PA8477801A1 (es)	2000-05-24
HRP20010046A2 (en)	2002-02-28
DE69904600T2 (de)	2003-11-13
AU766056B2 (en)	2003-10-09
JP2003521447A (ja)	2003-07-15
EA200100053A1 (ru)	2001-08-27
EA003191B1 (ru)	2003-02-27
EP1240903A2 (en)	2002-09-18
BRPI9912156B1 (pt)	2016-07-26
DK1098898T3 (da)	2003-04-07
HK1034261A1 (en)	2001-10-19
AP2001002039A0 (en)	2001-03-31
OA11706A (en)	2005-01-13
ZA200100417B (en)	2002-02-27
KR100694721B1 (ko)	2007-03-15
GT199900111A (es)	2001-01-05
BR9912156A (pt)	2001-04-10
CZ300447B6 (cs)	2009-05-20
ATE229964T1 (de)	2003-01-15
CA2337857C (en)	2011-01-25
CN1188422C (zh)	2005-02-09
BRPI9912156B8 (pt)	2021-05-25
JP3437553B2 (ja)	2003-08-18
DZ2845A1 (fr)	2003-12-01
HUP0103432A3 (en)	2003-01-28
EP1098898A1 (en)	2001-05-16
TWI245770B (en)	2005-12-21
HU229700B1 (en)	2014-05-28
SV1999000096A (es)	2000-07-06
TNSN99145A1 (fr)	2005-11-10
IS5808A (is)	2001-01-12
JO2114B1 (en)	2000-05-21
SK762001A3 (en)	2001-10-08
US20030096795A1 (en)	2003-05-22
AR019388A1 (es)	2002-02-13
PE20000869A1 (es)	2000-09-08
TR200100111T2 (tr)	2002-02-21
KR20010071952A (ko)	2001-07-31
MA26660A1 (fr)	2004-12-20
NO20010282L (no)	2001-03-07
BG105253A (en)	2001-12-29
MY122323A (en)	2006-04-29
IL140824A (en)	2004-09-27
GC0000105A (en)	2005-06-29
PL195736B1 (pl)	2007-10-31
CN1324363A (zh)	2001-11-28
ID28070A (id)	2001-05-03
IL140824A0 (en)	2002-02-10
YU3401A (sh)	2005-06-10
EP1240903A3 (en)	2003-02-12
EP1098898B1 (en)	2002-12-18
WO2000004033A1 (en)	2000-01-27
CA2337857A1 (en)	2000-01-27
CZ2001219A3 (cs)	2001-07-11
NO20010282D0 (no)	2001-01-17
EE200100038A (et)	2002-06-17
DE69904600D1 (de)	2003-01-30
SK285311B6 (sk)	2006-10-05
PL345620A1 (en)	2002-01-02
AU5037999A (en)	2000-02-07
NZ509291A (en)	2003-05-30
HUP0103432A2 (hu)	2002-04-29
GB9815567D0 (en)	1998-09-16
US20030100537A1 (en)	2003-05-29
GEP20033030B (en)	2003-07-25
ES2189450T3 (es)	2003-07-01
US6514953B1 (en)	2003-02-04
PT1098898E (pt)	2003-04-30
CO5090836A1 (es)	2001-10-30

Legal Events

Date	Code	Title	Description
2019-08-12	MK1K	Patent expired

Publication	Publication Date	Title
NO329676B1 (no)	2010-11-29	Kalsium(3S)tetrahydro-3-furanyl(1S,2R)-3-(((4-aminofenyl)sulfonyl)(isobutyl)amino)-1-benzyl-2-(fosfonoksy)propylkarbamat samt anvendelse og fremstilling derav og farmasoytisk preparat
EA020489B1 (ru)	2014-11-28	Модуляторы фармакокинетических свойств лекарственных средств
RU2606951C1 (ru)	2017-01-10	Дихлорацетаты замещенных N4-[2-(диметилфосфорил)фенил]-N2-(2-метокси-4-пиперидин-1-илфенил)-5-хлорпиримидин-2,4-диаминов в качестве модуляторов ALK и EGFR, предназначенных для лечения рака
JP6154878B2 (ja)	2017-06-28	アタザナビルを含む錠剤組成物
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US20060134190A1 (en)	2006-06-22	Formulations of bisphosphonate drugs with improved bioavailability
WO2001000635A2 (en)	2001-01-04	Derivatives of (3s) tetrahydro-3-furanyl (1s,2r)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphonooxy)propylcarbamate
EP3131878A1 (en)	2017-02-22	Solid forms of a pharmaceutically active compound
MXPA01000617A (en)	2001-12-04	Calcium (3s) tetrahydro-3- furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl](isobutyl) amino]-1-benzyl-2- (phosphonooxy) propylcarbamate
HK1034261B (en)	2003-07-25	Calcium (3s) tetrahydro-3-furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino] -1-benzyl-2- (phosphonooxy) propylcarbamate
DK200200115U3 (da)	2002-06-28	Hidtil ukendte salte af 4-amino-1-hydroxybutyliden-1, 1-bisphosphonsyre, deres fremstilling og anvendelse
JPH0352855A (ja)	1991-03-07	アクリル酸塩、それらの製造方法、それらを含む薬剤組成物および医学におけるそれらの用途
JPS63295580A (ja)	1988-12-01	骨粗鬆症治療剤
WO1997040046A1 (en)	1997-10-30	Benzoquinolizine derivatives and medicinal compositions