NO331846B1 - Bredspektrede, substituerte oksindol-sulfonamid HIV-proteaseinhibitorer. - Google Patents

Bredspektrede, substituerte oksindol-sulfonamid HIV-proteaseinhibitorer. Download PDF

Info

Publication number: NO331846B1
Authority: NO; Norway
Prior art keywords: compounds; hiv; alkyl; compound; formula
Prior art date: 2002-08-14

Application number

NO20051291A

Other languages

English (en)

Norwegian (no)

Other versions

NO20051291L (no

Inventor

Piet Tom Bert Paul Wigerinck

Abdellah Tahri

Original Assignee

Tibotec Pharm 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.)

2002-08-14

Filing date

2005-03-14

Publication date

2012-04-23

2005-03-14 Application filed by Tibotec Pharm Ltd filed Critical Tibotec Pharm Ltd

2005-05-18 Publication of NO20051291L publication Critical patent/NO20051291L/no

2012-04-23 Publication of NO331846B1 publication Critical patent/NO331846B1/no

Links

239000004030 hiv protease inhibitor Substances 0.000 title description 13
SPKYQJAFIYJJOX-UHFFFAOYSA-N 2-oxo-3h-indole-1-sulfonamide Chemical class C1=CC=C2N(S(=O)(=O)N)C(=O)CC2=C1 SPKYQJAFIYJJOX-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 170
239000000203 mixture Substances 0.000 claims description 64
239000003814 drug Substances 0.000 claims description 46
-1 hexahydrofuro[2,3-b]furanyl Chemical group 0.000 claims description 33
229940079593 drug Drugs 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
208000015181 infectious disease Diseases 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 7
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
125000002541 furyl group Chemical group 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 4
208000005074 Retroviridae Infections Diseases 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims 2
239000003112 inhibitor Substances 0.000 abstract description 12
229940124530 sulfonamide Drugs 0.000 abstract 1
150000003456 sulfonamides Chemical class 0.000 abstract 1
241000725303 Human immunodeficiency virus Species 0.000 description 50
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
239000000543 intermediate Substances 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
108010010369 HIV Protease Proteins 0.000 description 33
238000002360 preparation method Methods 0.000 description 30
238000000034 method Methods 0.000 description 27
239000002904 solvent Substances 0.000 description 26
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
230000000694 effects Effects 0.000 description 15
238000009472 formulation Methods 0.000 description 15
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241000700605 Viruses Species 0.000 description 12
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238000006243 chemical reaction Methods 0.000 description 10
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230000036436 anti-hiv Effects 0.000 description 7
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HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 6
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208000031886 HIV Infections Diseases 0.000 description 5
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 description 5
150000001412 amines Chemical class 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
238000002648 combination therapy Methods 0.000 description 5
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230000001177 retroviral effect Effects 0.000 description 5
229960000311 ritonavir Drugs 0.000 description 5
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 5
238000006467 substitution reaction Methods 0.000 description 5
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FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
206010001513 AIDS related complex Diseases 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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230000001476 alcoholic effect Effects 0.000 description 4
150000001350 alkyl halides Chemical class 0.000 description 4
150000001413 amino acids Chemical group 0.000 description 4
230000000840 anti-viral effect Effects 0.000 description 4
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XTYSXGHMTNTKFH-BDEHJDMKSA-N (2s)-1-[(2s,4r)-4-benzyl-2-hydroxy-5-[[(1s,2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]amino]-5-oxopentyl]-n-tert-butyl-4-(pyridin-3-ylmethyl)piperazine-2-carboxamide;hydrate Chemical compound O.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 XTYSXGHMTNTKFH-BDEHJDMKSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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238000011160 research Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000008137 solubility enhancer Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
229960005314 suramin Drugs 0.000 description 1
208000010648 susceptibility to HIV infection Diseases 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
229960004556 tenofovir Drugs 0.000 description 1
WHAVBTKASWWFIJ-UHFFFAOYSA-N tert-butyl n-[3-(2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yloxycarbonylamino)-2-hydroxy-4-phenylbutyl]-n-(2-methylpropyl)carbamate Chemical compound C1OC2OCCC2C1OC(=O)NC(C(O)CN(CC(C)C)C(=O)OC(C)(C)C)CC1=CC=CC=C1 WHAVBTKASWWFIJ-UHFFFAOYSA-N 0.000 description 1
ALPKFOALTCELEH-UHFFFAOYSA-J tetrasodium 4-[[4-[[4-anilino-6-[[5-hydroxy-6-[(2-methoxy-5-sulfonatophenyl)diazenyl]-7-sulfonatonaphthalen-2-yl]amino]-1,3,5-triazin-2-yl]amino]-5-methoxy-2-methylphenyl]diazenyl]-5-hydroxynaphthalene-2,7-disulfonate Chemical compound CC1=CC(=C(C=C1N=NC2=C3C(=CC(=C2)S(=O)(=O)[O-])C=C(C=C3[O-])S(=O)(=O)O)OC)NC4=NC(=NC(=N4)NC5=CC6=CC(=C(C(=C6C=C5)[O-])N=NC7=C(C=CC(=C7)S(=O)(=O)[O-])OC)S(=O)(=O)O)NC8=CC=CC=C8.[Na+].[Na+].[Na+].[Na+] ALPKFOALTCELEH-UHFFFAOYSA-J 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229950011282 tivirapine Drugs 0.000 description 1
SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000002845 virion Anatomy 0.000 description 1
210000001835 viscera Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Molecular Biology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO20051291A 2002-08-14 2005-03-14 Bredspektrede, substituerte oksindol-sulfonamid HIV-proteaseinhibitorer. NO331846B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP02078384		2002-08-14
PCT/EP2003/050379 WO2004016619A1 (fr)	2002-08-14	2003-08-14	Oxindole sulfonamides substitues inhibiteurs a large spectre de la protease du vih

Publications (2)

Publication Number	Publication Date
NO20051291L NO20051291L (no)	2005-05-18
NO331846B1 true NO331846B1 (no)	2012-04-23

Family

ID=31725465

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20051291A NO331846B1 (no)	2002-08-14	2005-03-14	Bredspektrede, substituerte oksindol-sulfonamid HIV-proteaseinhibitorer.

Country Status (18)

Country	Link
US (1)	US7199148B2 (fr)
EP (1)	EP1546153A1 (fr)
JP (1)	JP4681296B2 (fr)
KR (1)	KR100994759B1 (fr)
CN (1)	CN1688586B (fr)
AP (1)	AP2126A (fr)
AU (1)	AU2003262574B2 (fr)
BR (1)	BR0305771A (fr)
CA (1)	CA2493940C (fr)
EA (1)	EA010486B1 (fr)
HR (1)	HRP20050606B1 (fr)
IL (1)	IL166462A (fr)
MX (1)	MXPA05001792A (fr)
NO (1)	NO331846B1 (fr)
NZ (1)	NZ538714A (fr)
PL (1)	PL375307A1 (fr)
WO (1)	WO2004016619A1 (fr)
ZA (1)	ZA200501223B (fr)

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US7109230B2 (en) *	2002-01-07	2006-09-19	Sequoia Pharmaceuticals, Inc.	Resistance-repellent retroviral protease inhibitors
WO2005087728A1 (fr) *	2004-03-11	2005-09-22	Sequoia Pharmaceuticals, Inc.	Inhibiteurs de la protease retrovirale inhibant la resistance
AU2005244121B2 (en) *	2004-05-07	2012-01-19	Sequoia Pharmaceuticals, Inc.	Resistance-repellent retroviral protease inhibitors
AR073248A1 (es)	2008-09-01	2010-10-20	Tibotec Pharm Ltd	Proceso para la preparacion de (1s, 2r)-3- ((4-aminofenil) sulfonil) ( isobutil) amino)-1- bencil-2- hidroxipropilcarbamato de (3r, 3as,6ar)- hexahidrofuro-(2,3-b) furan-3- ilo (darunavir) y compuestos intermediarios utiles en dicho proceso.
US8921415B2 (en)	2009-01-29	2014-12-30	Mapi Pharma Ltd.	Polymorphs of darunavir
PL2528923T3 (pl)	2010-01-28	2015-01-30	Mapi Pharma Ltd	Sposób wytwarzania darunawiru i pochodnych darunawiru
US8580294B2 (en)	2010-10-19	2013-11-12	International Partnership For Microbicides	Platinum-catalyzed intravaginal rings
WO2012092168A1 (fr) *	2010-12-27	2012-07-05	Purdue Research Foundation	Ligands p2 à système cyclique 6,5 bicyclique fusionné, et procédés de traitement d'une infection par le vih
WO2012092188A1 (fr) *	2010-12-27	2012-07-05	Ghosh Arun K	Ligands p1 formant des liaisons hydrogène et procédés de traitement d'une infection par le vih
US10137031B2 (en)	2013-11-14	2018-11-27	International Partnership For Microbicides, Inc.	Combination therapy intravaginal rings
US20170253607A1 (en) *	2014-09-11	2017-09-07	Shionogi & Co., Ltd.	Long-acting hiv protease inhibitor

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PH30929A (en)	1992-09-03	1997-12-23	Janssen Pharmaceutica Nv	Beads having a core coated with an antifungal and a polymer.
IS2334B (is) *	1992-09-08	2008-02-15	Vertex Pharmaceuticals Inc., (A Massachusetts Corporation)	Aspartyl próteasi hemjari af nýjum flokki súlfonamíða
US5723490A (en) *	1992-09-08	1998-03-03	Vertex Pharmaceuticals Incorporated	THF-containing sulfonamide inhibitors of aspartyl protease
ES2127938T3 (es)	1993-08-24	1999-05-01	Searle & Co	Hidroxietilamino sulfonamidas utiles como inhibidores de proteasas retroviricas.
ES2166786T3 (es)	1993-10-01	2002-05-01	Astrazeneca Ab	Procedimiento i.
DE69637380T2 (de) *	1995-01-20	2009-09-17	G.D. Searle Llc, Chicago	Bis-sulfonamid-hydroxyethylamino-derivate als inhibitoren retroviraler proteasen
US5756533A (en)	1995-03-10	1998-05-26	G.D. Searle & Co.	Amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US5705500A (en)	1995-03-10	1998-01-06	G.D. Searle & Co.	Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors
CN1149223C (zh) *	1995-03-10	2004-05-12	G·D·瑟尔公司	杂环羰基氨基酸羟乙氨基磺酰胺逆转录病毒蛋白酶抑制剂
US6150556A (en)	1995-03-10	2000-11-21	G. D. Dearle & Co.	Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US5753660A (en)	1995-11-15	1998-05-19	G. D. Searle & Co.	Substituted sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors
US6509038B2 (en)	1996-05-20	2003-01-21	Janssen Pharmaceutica N.V.	Antifungal compositions with improved bioavailability
CZ295502B6 (cs)	1997-03-26	2005-08-17	Janssen Pharmaceutica N. V.	Antifungální peleta, způsob její přípravy a farmaceutická dávková forma s obsahem těchto pelet
EP1042280A2 (fr)	1997-12-24	2000-10-11	Vertex Pharmaceuticals Incorporated	Pro-medicaments qui sont des inhibiteurs de l'aspartyl protease
AU2010299A (en)	1997-12-24	1999-07-19	Vertex Pharmaceuticals Incorporated	Prodrugs os aspartyl protease inhibitors
US6436989B1 (en)	1997-12-24	2002-08-20	Vertex Pharmaceuticals, Incorporated	Prodrugs of aspartyl protease inhibitors
AU2012199A (en)	1997-12-24	1999-07-19	Vertex Pharmaceuticals Incorporated	Prodrugs of aspartyl protease inhibitors
BR9912169A (pt) *	1998-06-19	2001-04-10	Vertex Pharma	Inibidores de sulfonamida de protease de aspartil
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2003
- 2003-08-14 NZ NZ538714A patent/NZ538714A/en not_active IP Right Cessation
- 2003-08-14 BR BR0305771-2A patent/BR0305771A/pt not_active IP Right Cessation
- 2003-08-14 PL PL03375307A patent/PL375307A1/xx unknown
- 2003-08-14 CA CA2493940A patent/CA2493940C/fr not_active Expired - Fee Related
- 2003-08-14 CN CN038240955A patent/CN1688586B/zh not_active Expired - Fee Related
- 2003-08-14 EP EP03787818A patent/EP1546153A1/fr not_active Withdrawn
- 2003-08-14 AU AU2003262574A patent/AU2003262574B2/en not_active Ceased
- 2003-08-14 MX MXPA05001792A patent/MXPA05001792A/es active IP Right Grant
- 2003-08-14 WO PCT/EP2003/050379 patent/WO2004016619A1/fr not_active Ceased
- 2003-08-14 US US10/524,451 patent/US7199148B2/en not_active Expired - Fee Related
- 2003-08-14 AP AP2005003245A patent/AP2126A/xx active
- 2003-08-14 EA EA200500350A patent/EA010486B1/ru not_active IP Right Cessation
- 2003-08-14 KR KR1020057001812A patent/KR100994759B1/ko not_active Expired - Fee Related
- 2003-08-14 JP JP2004528524A patent/JP4681296B2/ja not_active Expired - Fee Related
- 2003-08-14 HR HRP20050606AA patent/HRP20050606B1/hr not_active IP Right Cessation
2005
- 2005-01-24 IL IL166462A patent/IL166462A/en not_active IP Right Cessation
- 2005-02-10 ZA ZA200501223A patent/ZA200501223B/en unknown
- 2005-03-14 NO NO20051291A patent/NO331846B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
AP2005003245A0 (en)	2005-03-31
HRP20050606B1 (hr)	2014-04-25
PL375307A1 (en)	2005-11-28
JP2005537305A (ja)	2005-12-08
CA2493940C (fr)	2011-11-22
EA200500350A1 (ru)	2005-08-25
HRP20050606A2 (en)	2006-02-28
WO2004016619A1 (fr)	2004-02-26
CN1688586A (zh)	2005-10-26
CA2493940A1 (fr)	2004-02-26
IL166462A0 (en)	2006-01-15
IL166462A (en)	2012-04-30
NZ538714A (en)	2007-03-30
US7199148B2 (en)	2007-04-03
US20060058368A1 (en)	2006-03-16
BR0305771A (pt)	2004-10-05
KR20050042141A (ko)	2005-05-04
AU2003262574A1 (en)	2004-03-03
EP1546153A1 (fr)	2005-06-29
KR100994759B1 (ko)	2010-11-16
CN1688586B (zh)	2012-05-09
AP2126A (en)	2010-06-03
ZA200501223B (en)	2006-07-26
MXPA05001792A (es)	2005-04-25
AU2003262574B2 (en)	2009-07-09
EA010486B1 (ru)	2008-10-30
JP4681296B2 (ja)	2011-05-11
NO20051291L (no)	2005-05-18

Legal Events

Date	Code	Title	Description
2016-03-29	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO326883B1 (no)	2009-03-09	Bredspektret 2-(amino)-benzoxazolsulfonamid HIV proteasehemmere
AU2002310818A1 (en)	2003-05-01	Broadspectrum 2-amino-benzoxazole sulfonamide HIV protease inhibitors
CA2493940C (fr)	2011-11-22	Oxindole sulfonamides substitues inhibiteurs a large spectre de la protease du vih
NO328896B1 (no)	2010-06-07	2-(substituert-amino)-benzoxasolsulfonamid med HIV proteasehemmende virkning
KR101019648B1 (ko)	2011-03-07	광범위 스펙트럼의 치환된 벤즈이속사졸 설폰아미드ｈｉｖ 프로테아제 저해제
AU2003262561A1 (en)	2004-02-25	Broadspectrum 2-amino-benzothiazole sulfonamide hiv protease inhibitors
NO328122B1 (no)	2009-12-14	Bredspektrede heterocyklisk substituerte fenylinneholdende sulfonamid-HIV-proteaseinhibitorer
NO326702B1 (no)	2009-02-02	Bredspektrede substituerte benzimidazolsulfonamid HIV-proteaseinhibitorer
JP4879484B2 (ja)	2012-02-22	広スペクトルの２−アミノ−ベンゾチアゾールスルホンアミドｈｉｖプロテアーゼ阻害剤