OA13134A - Broadspectrum 2-amino-benzoxazole sulfamide HIV protease inhibitors. - Google Patents

Broadspectrum 2-amino-benzoxazole sulfamide HIV protease inhibitors. Download PDF

Info

Publication number: OA13134A
Authority: OA; OAPI
Prior art keywords: alkyl; compound; aryl; het1; het2
Prior art date: 2001-05-11

Application number

OA1200300277A

Other languages

English (en)

Inventor

Dominique Louis Nestor Ghislain Surleraux

Sandrine Marie Helene Vendeville

Wim Gaston Verschueren

Marie-Pierre T M M G De Bethune

Herman Augustinus De Kock

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.)

2001-05-11

Filing date

2002-05-10

Publication date

2006-12-13

2002-05-10 Application filed by Tibotec Pharm Ltd filed Critical Tibotec Pharm Ltd

2006-12-13 Publication of OA13134A publication Critical patent/OA13134A/en

Links

239000004030 hiv protease inhibitor Substances 0.000 title abstract description 4
VTLFDGPHXHNRKO-UHFFFAOYSA-N 1,3-benzoxazol-2-amine sulfamide Chemical compound S(=O)(=O)(N)N.NC=1OC2=C(N1)C=CC=C2 VTLFDGPHXHNRKO-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 202
239000000203 mixture Substances 0.000 claims abstract description 77
125000003118 aryl group Chemical group 0.000 claims abstract description 57
238000000034 method Methods 0.000 claims abstract description 36
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 28
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 21
239000000651 prodrug Substances 0.000 claims abstract description 12
229940002612 prodrug Drugs 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 8
150000002148 esters Chemical class 0.000 claims abstract description 8
-1 arylCi-galkyl Chemical group 0.000 claims description 90
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
125000001424 substituent group Chemical group 0.000 claims description 37
241000725303 Human immunodeficiency virus Species 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 34
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
239000003814 drug Substances 0.000 claims description 31
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
239000000126 substance Substances 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 24
229940079593 drug Drugs 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
229910052760 oxygen Inorganic materials 0.000 claims description 20
239000001301 oxygen Substances 0.000 claims description 20
229910052717 sulfur Inorganic materials 0.000 claims description 17
241000700605 Viruses Species 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
241000124008 Mammalia Species 0.000 claims description 15
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
239000011593 sulfur Substances 0.000 claims description 15
241001430294 unidentified retrovirus Species 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
238000011282 treatment Methods 0.000 claims description 12
108091005804 Peptidases Proteins 0.000 claims description 10
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125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
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230000002401 inhibitory effect Effects 0.000 claims description 7
230000001177 retroviral effect Effects 0.000 claims description 7
239000007962 solid dispersion Substances 0.000 claims description 7
208000005074 Retroviridae Infections Diseases 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
230000035772 mutation Effects 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
108010010369 HIV Protease Proteins 0.000 claims description 4
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 5
101100001677 Emericella variicolor andL gene Proteins 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 16
238000003556 assay Methods 0.000 abstract description 10
229940124522 antiretrovirals Drugs 0.000 abstract description 4
239000003153 chemical reaction reagent Substances 0.000 abstract description 3
230000008569 process Effects 0.000 abstract description 3
238000009007 Diagnostic Kit Methods 0.000 abstract description 2
239000003903 antiretrovirus agent Substances 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
150000001204 N-oxides Chemical class 0.000 abstract 1
239000002207 metabolite Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000000543 intermediate Substances 0.000 description 28
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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125000002619 bicyclic group Chemical group 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 6
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150000007513 acids Chemical class 0.000 description 5
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230000036436 anti-hiv Effects 0.000 description 5
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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 4
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125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000003362 replicative effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000003381 stabilizer Substances 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
238000007920 subcutaneous administration Methods 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
150000003456 sulfonamides Chemical class 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
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960004556 tenofovir Drugs 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
229960000838 tipranavir Drugs 0.000 description 1
229950011282 tivirapine Drugs 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
238000001665 trituration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000035899 viability Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
210000002845 virion Anatomy 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

OA1200300277A 2001-05-11 2002-05-10 Broadspectrum 2-amino-benzoxazole sulfamide HIV protease inhibitors. OA13134A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP01201732		2001-05-11

Publications (1)

Publication Number	Publication Date
OA13134A true OA13134A (en)	2006-12-13

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ID=8180286

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200300277A OA13134A (en)	2001-05-11	2002-05-10	Broadspectrum 2-amino-benzoxazole sulfamide HIV protease inhibitors.

Country Status (31)

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US (2)	US7622490B2 (de)
EP (1)	EP1387842B1 (de)
JP (1)	JP4467889B2 (de)
KR (1)	KR100878853B1 (de)
CN (1)	CN100549007C (de)
AP (1)	AP1652A (de)
AR (1)	AR035970A1 (de)
AT (1)	ATE429431T1 (de)
AU (1)	AU2002310818B2 (de)
BG (1)	BG66350B1 (de)
BR (1)	BR0209594A (de)
CA (1)	CA2444895C (de)
CY (1)	CY1109247T1 (de)
CZ (1)	CZ304524B6 (de)
DE (1)	DE60232067D1 (de)
DK (1)	DK1387842T3 (de)
EA (1)	EA009590B1 (de)
EE (1)	EE05307B1 (de)
ES (1)	ES2325809T3 (de)
HR (1)	HRP20031026B1 (de)
HU (1)	HUP0400438A3 (de)
IL (1)	IL158093A0 (de)
MX (1)	MXPA03010258A (de)
NO (1)	NO326883B1 (de)
NZ (1)	NZ529250A (de)
OA (1)	OA13134A (de)
PL (1)	PL209029B1 (de)
PT (1)	PT1387842E (de)
SK (1)	SK287952B6 (de)
WO (1)	WO2002092595A1 (de)
ZA (1)	ZA200307799B (de)

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DE10026698A1 (de)	2000-05-30	2001-12-06	Basf Ag	Selbstemulgierende Wirkstoffformulierung und Verwendung dieser Formulierung
CA2472580A1 (en)	2002-01-07	2003-07-17	Sequoia Pharmaceuticals	Broad spectrum inhibitors
US7157489B2 (en)	2002-03-12	2007-01-02	The Board Of Trustees Of The University Of Illinois	HIV protease inhibitors
US8025899B2 (en)	2003-08-28	2011-09-27	Abbott Laboratories	Solid pharmaceutical dosage form
CA2537877C (en) *	2003-09-30	2015-03-17	Tibotec Pharmaceuticals Ltd.	Methods for the preparation of benzoxazole sulfonamide compounds and intermediates thereof
US20050131042A1 (en) *	2003-12-11	2005-06-16	Flentge Charles A.	HIV protease inhibiting compounds
US8193227B2 (en)	2003-12-11	2012-06-05	Abbott Laboratories	HIV protease inhibiting compounds
US7772411B2 (en)	2003-12-23	2010-08-10	Tibotec Pharmaceuticals Ltd.	Process for the preparation of (3R,3aS,6aR)-hexahydrofuro [2,3-b] furan-3-yl (1S,2R)-3[[(4-aminophenyl) sulfonyl] (isobutyl) amino]-1-benzyl-2-hydroxypropylcarbamate
HRP20090488T1 (hr)	2003-12-23	2009-10-31	Tibotec Pharmaceuticals Ltd.	Postupak za pripravu (3r,3as,6ar)-heksahidrofuro[2,3-b]furan-3-il(1s,23)-3-[[(4-aminofenil)sulfonil](izobutil)amino]-1-benzil-2-hidroksipropilkarbamata
MXPA06012909A (es) *	2004-05-07	2007-09-06	Sequoia Pharmaceuticals Inc	Inhibidores de proteasa retroviral repelente de resistencia.
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Also Published As

Publication number	Publication date
IL158093A0 (en)	2004-03-28
AR035970A1 (es)	2004-07-28
HUP0400438A3 (en)	2007-08-28
BR0209594A (pt)	2004-03-30
AP1652A (en)	2006-08-11
CN100549007C (zh)	2009-10-14
DE60232067D1 (de)	2009-06-04
AP2003002904A0 (en)	2003-12-31
CZ304524B6 (cs)	2014-06-18
EE200300547A (et)	2004-02-16
CZ20033290A3 (cs)	2004-05-12
NZ529250A (en)	2005-05-27
ES2325809T3 (es)	2009-09-18
SK287952B6 (sk)	2012-06-04
KR20040022417A (ko)	2004-03-12
NO326883B1 (no)	2009-03-09
AU2002310818B2 (en)	2007-12-13
CY1109247T1 (el)	2014-07-02
HUP0400438A2 (hu)	2004-08-30
ZA200307799B (en)	2005-03-30
EE05307B1 (et)	2010-06-15
HRP20031026A2 (en)	2005-10-31
ATE429431T1 (de)	2009-05-15
US7622490B2 (en)	2009-11-24
MXPA03010258A (es)	2005-03-07
SK14902003A3 (sk)	2004-07-07
WO2002092595A1 (en)	2002-11-21
NO20034988D0 (no)	2003-11-10
EA200301234A1 (ru)	2004-04-29
EP1387842B1 (de)	2009-04-22
KR100878853B1 (ko)	2009-01-15
EP1387842A1 (de)	2004-02-11
US20040106661A1 (en)	2004-06-03
PT1387842E (pt)	2009-07-20
CA2444895C (en)	2011-02-15
HRP20031026B1 (hr)	2012-07-31
JP4467889B2 (ja)	2010-05-26
CA2444895A1 (en)	2002-11-21
EA009590B1 (ru)	2008-02-28
HK1062912A1 (en)	2004-12-03
BG108309A (bg)	2004-12-30
PL209029B1 (pl)	2011-07-29
BG66350B1 (bg)	2013-08-30
CN1507446A (zh)	2004-06-23
PL366780A1 (en)	2005-02-07
JP2004534757A (ja)	2004-11-18
DK1387842T3 (da)	2009-08-10
US20100029632A1 (en)	2010-02-04
US7863306B2 (en)	2011-01-04

Publication	Publication Date	Title
US7863306B2 (en)	2011-01-04	Broadspectrum 2-amino-benzoxazole sulfonamide HIV protease inhibitors
US7595334B2 (en)	2009-09-29	Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors
AU2002310818A1 (en)	2003-05-01	Broadspectrum 2-amino-benzoxazole sulfonamide HIV protease inhibitors
AU2003262574B2 (en)	2009-07-09	Broadspectrum substituted oxindole sulfonamide HIV protease inhibitors
EP1517899B1 (de)	2007-08-29	Substituierte benzisoxazolsulfonamide mit breitbändiger hiv-protease hemmender wirkung
AU2003262561A1 (en)	2004-02-25	Broadspectrum 2-amino-benzothiazole sulfonamide hiv protease inhibitors
AU2002257774A1 (en)	2003-04-10	Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors
HK1062912B (en)	2009-08-28	Broadspectrum 2-amino-benzoxazole sulfonamide hiv protease inhibitors
HK1076099B (en)	2008-02-01	Broadspectrum substituted benzisoxazole sulfonamide hiv protease inhibitors