NO330184B1 - Bredspektrede substituerte benzoksazolsulfonamid HIV-proteaseinhibitorer - Google Patents

Bredspektrede substituerte benzoksazolsulfonamid HIV-proteaseinhibitorer Download PDF

Info

Publication number: NO330184B1
Authority: NO; Norway
Prior art keywords: amino; compound; compounds; sulfonyl; propyl
Prior art date: 2002-05-17

Application number

NO20045444A

Other languages

English (en)

Norwegian (no)

Other versions

NO20045444L (no

Inventor

Herman Augustinus De Kock

Bernhard Joanna Bernard Vergouwen

Dominique Louis Nestor Ghislain Surleraux

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.)

2002-05-17

Filing date

2004-12-14

Publication date

2011-02-28

2004-12-14 Application filed by Tibotec Pharm Ltd filed Critical Tibotec Pharm Ltd

2005-02-16 Publication of NO20045444L publication Critical patent/NO20045444L/no

2011-02-28 Publication of NO330184B1 publication Critical patent/NO330184B1/no

Links

239000004030 hiv protease inhibitor Substances 0.000 title abstract description 14
238000001228 spectrum Methods 0.000 title description 4
BBFZKZROAWKUCD-UHFFFAOYSA-N 1,3-benzoxazole-2-sulfonamide Chemical class C1=CC=C2OC(S(=O)(=O)N)=NC2=C1 BBFZKZROAWKUCD-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 184
239000000203 mixture Substances 0.000 claims abstract description 61
150000003839 salts Chemical class 0.000 claims abstract description 21
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
239000003814 drug Substances 0.000 claims description 42
-1 hexahydrofurofuranyl Chemical group 0.000 claims description 36
229940079593 drug Drugs 0.000 claims description 25
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125000000217 alkyl group Chemical group 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
108091005804 Peptidases Proteins 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
239000004365 Protease Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
150000001204 N-oxides Chemical class 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
230000001717 pathogenic effect Effects 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
230000001177 retroviral effect Effects 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 3
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VLUBVAHDXUIEHZ-UHFFFAOYSA-N 1,3-thiazol-5-ylmethyl n-[4-[(3-amino-1,2-benzoxazol-5-yl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound C=1C=C2ON=C(N)C2=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OCC=1SC=NC=1)CC1=CC=CC=C1 VLUBVAHDXUIEHZ-UHFFFAOYSA-N 0.000 claims description 2
YPXXNUSXDOMVSN-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl n-[3-hydroxy-4-[2-methylpropyl-[(3-pyrrolidin-1-yl-1,2-benzoxazol-5-yl)sulfonyl]amino]-1-phenylbutan-2-yl]carbamate Chemical compound C=1C=C2ON=C(N3CCCC3)C2=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OC1C2CCOC2OC1)CC1=CC=CC=C1 YPXXNUSXDOMVSN-UHFFFAOYSA-N 0.000 claims description 2
NFFKRGHAASYAGP-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl n-[3-hydroxy-4-[2-methylpropyl-[[3-(2-pyrrolidin-1-ylethylamino)-1,2-benzoxazol-5-yl]sulfonyl]amino]-1-phenylbutan-2-yl]carbamate Chemical compound C=1C=C2ON=C(NCCN3CCCC3)C2=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OC1C2CCOC2OC1)CC1=CC=CC=C1 NFFKRGHAASYAGP-UHFFFAOYSA-N 0.000 claims description 2
WYRBQDGCISXTLW-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl n-[3-hydroxy-4-[[3-(methylamino)-1,2-benzoxazol-5-yl]sulfonyl-(2-methylpropyl)amino]-1-phenylbutan-2-yl]carbamate Chemical compound C1=C2C(NC)=NOC2=CC=C1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OC1C2CCOC2OC1)CC1=CC=CC=C1 WYRBQDGCISXTLW-UHFFFAOYSA-N 0.000 claims description 2
AAWKQMSSRBFCGO-UHFFFAOYSA-N 2,3,3a,4,5,6a-hexahydrofuro[2,3-b]furan-4-yl n-[4-[(3-amino-1,2-benzoxazol-5-yl)sulfonyl-(2-methylpropyl)amino]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound C=1C=C2ON=C(N)C2=CC=1S(=O)(=O)N(CC(C)C)CC(O)C(NC(=O)OC1C2CCOC2OC1)CC1=CC=CC=C1 AAWKQMSSRBFCGO-UHFFFAOYSA-N 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
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XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
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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
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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
- C07D413/02—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
- 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
- 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
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
- 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
- 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)
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)
Virology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Molecular Biology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (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)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO20045444A 2002-05-17 2004-12-14 Bredspektrede substituerte benzoksazolsulfonamid HIV-proteaseinhibitorer NO330184B1 (no)

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PCT/EP2003/050173 WO2003097616A1 (en)	2002-05-17	2003-05-16	Broadspectrum substituted benzisoxazole sulfonamide hiv protease inhibitors

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US (1)	US7462636B2 (de)
EP (1)	EP1517899B1 (de)
JP (2)	JP4674084B2 (de)
KR (2)	KR101019648B1 (de)
CN (1)	CN100582097C (de)
AP (1)	AP2004003190A0 (de)
AR (1)	AR039887A1 (de)
AT (1)	ATE371652T1 (de)
AU (1)	AU2003238074B2 (de)
BR (1)	BR0310089A (de)
CA (1)	CA2485903C (de)
CY (1)	CY1107040T1 (de)
DE (1)	DE60315984T2 (de)
DK (1)	DK1517899T3 (de)
EA (1)	EA010908B1 (de)
ES (1)	ES2292976T3 (de)
HR (1)	HRP20050607B1 (de)
IL (1)	IL165043A0 (de)
MX (1)	MXPA04011466A (de)
MY (1)	MY135226A (de)
NO (1)	NO330184B1 (de)
NZ (1)	NZ536496A (de)
PL (1)	PL373425A1 (de)
PT (1)	PT1517899E (de)
SI (1)	SI1517899T1 (de)
TW (1)	TWI356700B (de)
WO (1)	WO2003097616A1 (de)
ZA (1)	ZA200410156B (de)

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IL165043A0 (en) *	2002-05-17	2005-12-18	Tibotec Pharm Ltd	broadspectrum substituted benzisoxazole sulfonamide hiv protease inhibitors
JP2007528423A (ja) *	2004-03-11	2007-10-11	セコイア、ファーマシューティカルズ、インコーポレイテッド	耐性防止レトロウイルスプロテアーゼ阻害薬
US7378441B2 (en) *	2004-05-07	2008-05-27	Sequoia Pharmaceuticals, Inc.	Resistance-repellent retroviral protease inhibitors
DK1856125T3 (da)	2005-02-25	2009-12-07	Tibotec Pharm Ltd	Syntese af proteasehæmmerforstadie
EP2139883A4 (de) *	2007-03-23	2011-06-22	Univ Massachusetts	Hiv-1-proteasehemmer
JP2011515444A (ja) *	2008-03-25	2011-05-19	フォーマックファーマシューティカルズナムローゼフェンノートシャップ	固体分散体の調製方法
WO2011061590A1 (en)	2009-11-17	2011-05-26	Hetero Research Foundation	Novel carboxamide derivatives as hiv inhibitors
DE102010004957A1 (de)	2010-01-14	2011-07-21	Universitätsklinikum Jena, 07743	Biologisch wirksame Moleküle zur Beeinflussung von Virus-, Bakterien-, Parasiten-infizierten Zellen und/oder Tumorzellen und Verfahren zu deren Anwendung
JP2016503395A (ja)	2012-10-31	2016-02-04	バイエル・クロップサイエンス・アクチェンゲゼルシャフト	病害生物防除剤としての複素環化合物
KR101661952B1 (ko) *	2013-03-07	2016-10-04	다우 글로벌 테크놀로지스 엘엘씨	극저점도의 신규한 에스테르화된 셀룰로스 에테르

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ES2123065T3 (es) *	1992-08-25	1999-01-01	Searle & Co	Hidroxietilamino-sulfonamidas utiles como inhibidores de proteasas retroviricas.
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
EP0715618B1 (de)	1993-08-24	1998-12-16	G.D. Searle & Co.	Hydroxyaminosulfonamide verwendbar als inhibitoren retroviraler proteasen
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BR9607625A (pt)	1995-03-10	1999-06-15	Searle & Co	Inibidores de protease retroviral sulfonamida hidroxietilamino de aminoácido heterociclocarbonila
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2003
- 2003-05-16 IL IL16504303A patent/IL165043A0/xx not_active IP Right Cessation
- 2003-05-16 DK DK03735707T patent/DK1517899T3/da active
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- 2003-05-16 WO PCT/EP2003/050173 patent/WO2003097616A1/en not_active Ceased
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2004
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2007
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Also Published As

Publication number	Publication date
US7462636B2 (en)	2008-12-09
JP4674084B2 (ja)	2011-04-20
CN100582097C (zh)	2010-01-20
CY1107040T1 (el)	2012-09-26
KR20100130234A (ko)	2010-12-10
BR0310089A (pt)	2005-02-15
AU2003238074B2 (en)	2009-04-30
ZA200410156B (en)	2005-11-30
CA2485903A1 (en)	2003-11-27
TW200404538A (en)	2004-04-01
EP1517899B1 (de)	2007-08-29
JP2011051999A (ja)	2011-03-17
JP2005527607A (ja)	2005-09-15
DE60315984T2 (de)	2008-05-29
EP1517899A1 (de)	2005-03-30
AR039887A1 (es)	2005-03-09
HRP20050607B1 (hr)	2014-07-04
AP2004003190A0 (en)	2004-12-31
DE60315984D1 (de)	2007-10-11
US20050171173A1 (en)	2005-08-04
EA200401524A1 (ru)	2005-06-30
MY135226A (en)	2008-02-29
ATE371652T1 (de)	2007-09-15
NZ536496A (en)	2006-06-30
PL373425A1 (en)	2005-08-22
ES2292976T3 (es)	2008-03-16
CA2485903C (en)	2011-08-16
EA010908B1 (ru)	2008-12-30
PT1517899E (pt)	2007-11-16
DK1517899T3 (da)	2007-12-03
IL165043A0 (en)	2005-12-18
KR20050013549A (ko)	2005-02-04
AU2003238074A1 (en)	2003-12-02
TWI356700B (en)	2012-01-21
HK1076099A1 (en)	2006-01-06
SI1517899T1 (sl)	2008-02-29
MXPA04011466A (es)	2005-02-14
NO20045444L (no)	2005-02-16
WO2003097616A1 (en)	2003-11-27
CN1668605A (zh)	2005-09-14
KR101019648B1 (ko)	2011-03-07
HRP20050607A2 (en)	2006-02-28

Legal Events

Date	Code	Title	Description
2015-12-21	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US20100029632A1 (en)	2010-02-04	Broadspectrum 2-amino-benzoxazole sulfonamide hiv protease inhibitors
AU2002310818A1 (en)	2003-05-01	Broadspectrum 2-amino-benzoxazole sulfonamide HIV protease inhibitors
NO330184B1 (no)	2011-02-28	Bredspektrede substituerte benzoksazolsulfonamid HIV-proteaseinhibitorer
AU2003262561B2 (en)	2008-10-16	Broadspectrum 2-amino-benzothiazole sulfonamide HIV protease inhibitors
US7199148B2 (en)	2007-04-03	Broadspectrum substituted oxindole sulfonamide HIV protease inhibitors
NO328896B1 (no)	2010-06-07	2-(substituert-amino)-benzoxasolsulfonamid med HIV proteasehemmende virkning
NO328122B1 (no)	2009-12-14	Bredspektrede heterocyklisk substituerte fenylinneholdende sulfonamid-HIV-proteaseinhibitorer
US20050171175A1 (en)	2005-08-04	Broadspectrum substituted benzimidazole sulfonamide hiv protease inhibitors
HK1076099B (en)	2008-02-01	Broadspectrum substituted benzisoxazole sulfonamide hiv protease inhibitors
IL163960A (en)	2013-08-29	Benzimidazoles Sulphonamides are broad-spectrum as vih protease inhibitors and as an overall preparation