OA12464A - Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors. - Google Patents

Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors. Download PDF

Info

Publication number: OA12464A
Authority: OA; OAPI
Prior art keywords: alkyl; het1; het2; aryl; amino
Prior art date: 2001-04-09

Application number

OA1200300253A

Other languages

English (en)

Inventor

Dominique Louis Nest Surleraux

Sandrine Marie Hele Vendeville

Wim Gaston Verschueren

De Marie-Pierre T M M Bethune

Herman Augustinus De Kock

Abdellah Tahri

Montserrat Erra Sola

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.)

2001-04-09

Filing date

2002-04-09

Publication date

2006-05-24

2002-04-09 Application filed by Tibotec Pharm Ltd filed Critical Tibotec Pharm Ltd

2006-05-24 Publication of OA12464A publication Critical patent/OA12464A/en

Links

-1 2-(substituted-amino)-benzoxazole sulfonamide Chemical class 0.000 title claims description 80
239000004030 hiv protease inhibitor Substances 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 173
125000003118 aryl group Chemical group 0.000 claims abstract description 82
239000000203 mixture Substances 0.000 claims abstract description 72
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 58
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
238000000034 method Methods 0.000 claims abstract description 38
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 31
125000003277 amino group Chemical group 0.000 claims abstract description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 22
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
239000000651 prodrug Substances 0.000 claims abstract description 12
229940002612 prodrug Drugs 0.000 claims abstract description 12
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
150000002148 esters Chemical class 0.000 claims abstract description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
229910052739 hydrogen Inorganic materials 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 46
125000001424 substituent group Chemical group 0.000 claims description 40
241000725303 Human immunodeficiency virus Species 0.000 claims description 31
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 29
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
239000003814 drug Substances 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
229940079593 drug Drugs 0.000 claims description 22
229910052760 oxygen Inorganic materials 0.000 claims description 22
239000001301 oxygen Substances 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
239000011593 sulfur Substances 0.000 claims description 19
239000000126 substance Substances 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
239000004365 Protease Substances 0.000 claims description 10
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 10
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
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125000004429 atom Chemical group 0.000 claims description 8
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
230000001177 retroviral effect Effects 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
208000005074 Retroviridae Infections Diseases 0.000 claims description 3
125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 3
125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 3
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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 2
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 14
238000003556 assay Methods 0.000 abstract description 10
229940124522 antiretrovirals Drugs 0.000 abstract description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract description 4
239000003153 chemical reaction reagent Substances 0.000 abstract description 4
230000008569 process Effects 0.000 abstract description 3
239000003903 antiretrovirus agent Substances 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
238000009007 Diagnostic Kit Methods 0.000 abstract 1
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 73
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
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JPBLHOJFMBOCAF-UHFFFAOYSA-N 1,3-benzoxazol-2-amine Chemical compound C1=CC=C2OC(N)=NC2=C1 JPBLHOJFMBOCAF-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
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150000003254 radicals Chemical class 0.000 description 5
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 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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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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Classifications

- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
- 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
- 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
- A61P35/00—Antineoplastic agents
- 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
- 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
- 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
- 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
- C07D417/14—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 three or more hetero rings
- 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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
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AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

OA1200300253A 2001-04-09 2002-04-09 Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors. OA12464A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01201308		2001-04-09
US28770401P	2001-05-02	2001-05-02

Publications (1)

Publication Number	Publication Date
OA12464A true OA12464A (en)	2006-05-24

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ID=26076876

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200300253A OA12464A (en)	2001-04-09	2002-04-09	Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors.

Country Status (25)

Country	Link
US (2)	US7244752B2 (de)
EP (1)	EP1397367A2 (de)
JP (1)	JP4417010B2 (de)
KR (1)	KR100872029B1 (de)
CN (1)	CN100491360C (de)
AP (1)	AP1544A (de)
AR (1)	AR035819A1 (de)
AU (1)	AU2002257774B2 (de)
BG (1)	BG66371B1 (de)
BR (1)	BR0208796A (de)
CA (1)	CA2442870C (de)
CZ (1)	CZ303139B6 (de)
EA (1)	EA007383B1 (de)
EE (1)	EE05384B1 (de)
HR (1)	HRP20030905B1 (de)
HU (1)	HUP0303744A3 (de)
IL (1)	IL158092A0 (de)
MX (1)	MXPA03009179A (de)
NO (1)	NO328896B1 (de)
NZ (1)	NZ528954A (de)
OA (1)	OA12464A (de)
PL (1)	PL367084A1 (de)
SK (1)	SK288232B6 (de)
WO (1)	WO2002081478A2 (de)
ZA (1)	ZA200307683B (de)

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2002
- 2002-04-09 EP EP02727554A patent/EP1397367A2/de not_active Withdrawn
- 2002-04-09 PL PL02367084A patent/PL367084A1/xx unknown
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- 2002-04-09 MX MXPA03009179A patent/MXPA03009179A/es active IP Right Grant
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- 2002-04-09 AU AU2002257774A patent/AU2002257774B2/en not_active Ceased
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- 2002-04-09 KR KR1020037013144A patent/KR100872029B1/ko not_active Expired - Fee Related
- 2002-04-09 US US10/474,162 patent/US7244752B2/en not_active Expired - Fee Related
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- 2002-04-09 OA OA1200300253A patent/OA12464A/en unknown
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- 2002-04-09 CZ CZ20032936A patent/CZ303139B6/cs not_active IP Right Cessation
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- 2002-04-09 CN CNB028114809A patent/CN100491360C/zh not_active Expired - Fee Related
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Also Published As

Publication number	Publication date
KR100872029B1 (ko)	2008-12-05
SK13392003A3 (en)	2004-10-05
HRP20030905A2 (en)	2005-08-31
NO20034505D0 (no)	2003-10-08
AP2003002882A0 (en)	2003-12-31
BR0208796A (pt)	2004-03-09
EE05384B1 (et)	2011-02-15
AU2002257774B2 (en)	2007-08-30
KR20030090719A (ko)	2003-11-28
CZ303139B6 (cs)	2012-04-25
NO20034505L (no)	2003-12-08
CN1636006A (zh)	2005-07-06
JP4417010B2 (ja)	2010-02-17
HUP0303744A2 (hu)	2004-03-01
NO328896B1 (no)	2010-06-07
US7595334B2 (en)	2009-09-29
CZ20032936A3 (cs)	2004-05-12
BG108218A (bg)	2004-09-30
WO2002081478A2 (en)	2002-10-17
CA2442870C (en)	2011-08-02
WO2002081478A3 (en)	2003-05-01
NZ528954A (en)	2005-04-29
EA007383B1 (ru)	2006-10-27
CN100491360C (zh)	2009-05-27
JP2004529144A (ja)	2004-09-24
US7244752B2 (en)	2007-07-17
HRP20030905B1 (en)	2012-03-31
PL367084A1 (en)	2005-02-21
IL158092A0 (en)	2004-03-28
BG66371B1 (bg)	2013-10-31
HUP0303744A3 (en)	2008-03-28
US20070135447A1 (en)	2007-06-14
AR035819A1 (es)	2004-07-14
EA200301110A1 (ru)	2004-04-29
US20040132791A1 (en)	2004-07-08
ZA200307683B (en)	2005-03-30
EE200300494A (et)	2003-12-15
AP1544A (en)	2006-01-12
EP1397367A2 (de)	2004-03-17
CA2442870A1 (en)	2002-10-17
MXPA03009179A (es)	2004-11-22
SK288232B6 (sk)	2014-11-04

Publication	Publication Date	Title
US7595334B2 (en)	2009-09-29	Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors
CA2444895C (en)	2011-02-15	Broadspectrum 2-amino-benzoxazole sulfonamide hiv protease inhibitors
AU2002310818A1 (en)	2003-05-01	Broadspectrum 2-amino-benzoxazole sulfonamide HIV protease inhibitors
AU2002257774A1 (en)	2003-04-10	Broadspectrum 2-(substituted-amino)-benzoxazole sulfonamide HIV protease inhibitors
CA2493940C (en)	2011-11-22	Broadspectrum substituted oxindole sulfonamide hiv protease inhibitors
AU2003238074B2 (en)	2009-04-30	Broadspectrum substituted benzisoxazole 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