OA11196A - Hiv protease inhibitors - Google Patents

Hiv protease inhibitors Download PDF

Info

Publication number: OA11196A
Authority: OA; OAPI
Prior art keywords: compound; alkyl; group; purity; pharmaceutical composition
Prior art date: 1997-03-13

Application number

OA9900207A

Other languages

English (en)

Inventor

Kim F Albizati

Takuo Kobayashi

Siegfried Reich

Michael D Varney

Kanyin E Zhang

Original Assignee

Agouron Pharma

Japan Tobacco Inc

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.)

1997-03-13

Filing date

1999-09-13

Publication date

2003-05-21

1999-09-13 Application filed by Agouron Pharma, Japan Tobacco Inc filed Critical Agouron Pharma

2003-05-21 Publication of OA11196A publication Critical patent/OA11196A/en

Links

239000004030 hiv protease inhibitor Substances 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 80
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
-1 cycioalkyl Chemical group 0.000 claims description 125
125000000217 alkyl group Chemical group 0.000 claims description 68
125000003118 aryl group Chemical group 0.000 claims description 28
125000000623 heterocyclic group Chemical group 0.000 claims description 26
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
229940002612 prodrug Drugs 0.000 claims description 13
239000000651 prodrug Substances 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 3
241000725303 Human immunodeficiency virus Species 0.000 abstract description 20
208000030507 AIDS Diseases 0.000 abstract description 13
108010010369 HIV Protease Proteins 0.000 abstract description 10
239000003443 antiviral agent Substances 0.000 abstract description 3
238000003786 synthesis reaction Methods 0.000 abstract description 2
239000004480 active ingredient Substances 0.000 abstract 1
230000004071 biological effect Effects 0.000 abstract 1
230000010076 replication Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
239000000203 mixture Substances 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
239000002585 base Substances 0.000 description 25
210000004027 cell Anatomy 0.000 description 25
238000000034 method Methods 0.000 description 25
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235000019439 ethyl acetate Nutrition 0.000 description 16
150000003839 salts Chemical class 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
125000003282 alkyl amino group Chemical group 0.000 description 15
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238000009472 formulation Methods 0.000 description 14
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230000003013 cytotoxicity Effects 0.000 description 6
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ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 6
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208000031886 HIV Infections Diseases 0.000 description 5
108010016183 Human immunodeficiency virus 1 p16 protease Proteins 0.000 description 5
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241000700605 Viruses Species 0.000 description 5
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208000037357 HIV infectious disease Diseases 0.000 description 4
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125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000007017 scission Effects 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
210000000605 viral structure Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000003245 working effect Effects 0.000 description 1
229940071104 xylenesulfonate Drugs 0.000 description 1
239000012138 yeast extract Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 to carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D307/22—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

OA9900207A 1997-03-13 1999-09-13 Hiv protease inhibitors OA11196A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US81595197A	1997-03-13	1997-03-13

Publications (1)

Publication Number	Publication Date
OA11196A true OA11196A (en)	2003-05-21

Family

ID=25219265

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900207A OA11196A (en)	1997-03-13	1999-09-13	Hiv protease inhibitors

Country Status (35)

Country	Link
EP (1)	EP0970055A2 (ru)
JP (1)	JP2001516350A (ru)
KR (1)	KR100511089B1 (ru)
CN (1)	CN1179948C (ru)
AP (1)	AP1358A (ru)
AR (1)	AR012556A1 (ru)
AU (1)	AU743078B2 (ru)
BG (1)	BG63540B1 (ru)
BR (1)	BR9808867A (ru)
CA (1)	CA2284163A1 (ru)
CO (1)	CO4940496A1 (ru)
CZ (1)	CZ296647B6 (ru)
EA (1)	EA002378B1 (ru)
EE (1)	EE04114B1 (ru)
GE (1)	GEP20022764B (ru)
HR (1)	HRP980112A2 (ru)
HU (1)	HUP0001380A3 (ru)
IL (2)	IL131870A0 (ru)
IS (1)	IS5176A (ru)
MX (1)	MXPA99008395A (ru)
MY (1)	MY117535A (ru)
NO (1)	NO315555B1 (ru)
NZ (1)	NZ337706A (ru)
OA (1)	OA11196A (ru)
PA (1)	PA8448801A1 (ru)
PE (1)	PE58799A1 (ru)
PL (1)	PL192786B1 (ru)
SA (1)	SA98181116B1 (ru)
SK (1)	SK283636B6 (ru)
SV (1)	SV1998000038A (ru)
TR (1)	TR199902508T2 (ru)
TW (1)	TW200517112A (ru)
UA (1)	UA57772C2 (ru)
WO (1)	WO1998040357A2 (ru)
ZA (1)	ZA982047B (ru)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5484926A (en) *	1993-10-07	1996-01-16	Agouron Pharmaceuticals, Inc.	HIV protease inhibitors

1998
- 1998-03-04 HR HR08/815,951A patent/HRP980112A2/hr not_active Application Discontinuation
- 1998-03-11 ZA ZA982047A patent/ZA982047B/xx unknown
- 1998-03-12 BR BR9808867-0A patent/BR9808867A/pt not_active Application Discontinuation
- 1998-03-12 EE EEP199900416A patent/EE04114B1/xx not_active IP Right Cessation
- 1998-03-12 NZ NZ337706A patent/NZ337706A/en unknown
- 1998-03-12 AP APAP/P/1999/001648A patent/AP1358A/en active
- 1998-03-12 EA EA199900823A patent/EA002378B1/ru unknown
- 1998-03-12 TW TW094100045A patent/TW200517112A/zh unknown
- 1998-03-12 MX MXPA99008395A patent/MXPA99008395A/es not_active IP Right Cessation
- 1998-03-12 CZ CZ0319199A patent/CZ296647B6/cs not_active IP Right Cessation
- 1998-03-12 JP JP53974598A patent/JP2001516350A/ja not_active Ceased
- 1998-03-12 GE GEAP19984984A patent/GEP20022764B/en unknown
- 1998-03-12 EP EP98910300A patent/EP0970055A2/en not_active Withdrawn
- 1998-03-12 CN CNB988045389A patent/CN1179948C/zh not_active Expired - Fee Related
- 1998-03-12 TR TR1999/02508T patent/TR199902508T2/xx unknown
- 1998-03-12 PL PL335672A patent/PL192786B1/pl not_active IP Right Cessation
- 1998-03-12 IL IL13187098A patent/IL131870A0/xx active IP Right Grant
- 1998-03-12 HU HU0001380A patent/HUP0001380A3/hu unknown
- 1998-03-12 MY MYPI98001071A patent/MY117535A/en unknown
- 1998-03-12 CA CA002284163A patent/CA2284163A1/en not_active Abandoned
- 1998-03-12 WO PCT/US1998/004735 patent/WO1998040357A2/en not_active Ceased
- 1998-03-12 AU AU64575/98A patent/AU743078B2/en not_active Ceased
- 1998-03-12 SK SK1222-99A patent/SK283636B6/sk not_active IP Right Cessation
- 1998-03-12 AR ARP980101104A patent/AR012556A1/es active IP Right Grant
- 1998-03-12 PE PE1998000171A patent/PE58799A1/es not_active Application Discontinuation
- 1998-03-12 KR KR10-1999-7008331A patent/KR100511089B1/ko not_active Expired - Fee Related
- 1998-03-13 CO CO98014251A patent/CO4940496A1/es unknown
- 1998-03-13 PA PA19988448801A patent/PA8448801A1/es unknown
- 1998-03-13 SV SV1998000038A patent/SV1998000038A/es not_active Application Discontinuation
- 1998-04-21 SA SA98181116A patent/SA98181116B1/ar unknown
- 1998-12-03 UA UA99095049A patent/UA57772C2/ru unknown
1999
- 1999-09-10 IL IL131870A patent/IL131870A/en not_active IP Right Cessation
- 1999-09-10 IS IS5176A patent/IS5176A/is unknown
- 1999-09-10 NO NO19994415A patent/NO315555B1/no not_active IP Right Cessation
- 1999-09-13 OA OA9900207A patent/OA11196A/en unknown
- 1999-09-13 BG BG103727A patent/BG63540B1/bg unknown

Also Published As

Publication number	Publication date
MXPA99008395A (es)	2003-08-12
BR9808867A (pt)	2000-07-11
CN1253548A (zh)	2000-05-17
CO4940496A1 (es)	2000-07-24
EP0970055A2 (en)	2000-01-12
SA98181116B1 (ar)	2006-10-04
NO315555B1 (no)	2003-09-22
TW200517112A (en)	2005-06-01
AP1358A (en)	2004-12-03
GEP20022764B (en)	2002-08-26
PL192786B1 (pl)	2006-12-29
AU743078B2 (en)	2002-01-17
CN1179948C (zh)	2004-12-15
EA199900823A1 (ru)	2000-04-24
EE04114B1 (et)	2003-08-15
WO1998040357A2 (en)	1998-09-17
PL335672A1 (en)	2000-05-08
BG63540B1 (bg)	2002-04-30
CZ319199A3 (cs)	2000-06-14
PA8448801A1 (es)	2000-05-24
ZA982047B (en)	1998-09-28
IL131870A (en)	2006-04-10
UA57772C2 (ru)	2003-07-15
KR20000076236A (ko)	2000-12-26
TR199902508T2 (xx)	2000-02-21
NO994415L (no)	1999-11-10
EE9900416A (et)	2000-04-17
NO994415D0 (no)	1999-09-10
CA2284163A1 (en)	1998-09-17
SV1998000038A (es)	1999-02-15
MY117535A (en)	2004-07-31
BG103727A (bg)	2000-04-28
CZ296647B6 (cs)	2006-05-17
HRP980112A2 (en)	1998-12-31
PE58799A1 (es)	1999-07-12
IL131870A0 (en)	2001-03-19
KR100511089B1 (ko)	2005-08-31
IS5176A (is)	1999-09-10
WO1998040357A3 (en)	1998-11-26
SK122299A3 (en)	2000-05-16
NZ337706A (en)	2001-04-27
SK283636B6 (sk)	2003-11-04
HUP0001380A3 (en)	2001-12-28
AP9901648A0 (en)	1999-09-30
JP2001516350A (ja)	2001-09-25
HUP0001380A2 (hu)	2000-09-28
EA002378B1 (ru)	2002-04-25
AR012556A1 (es)	2000-11-08
AU6457598A (en)	1998-09-29

Publication	Publication Date	Title
KR100296462B1 (ko)	2001-10-24	레트로바이러스프로테아제억제제로서유용한술포닐알칸오일아미노히드록시에틸아미노술폰아미드
KR100572494B1 (ko)	2007-04-25	설포닐아미노카복실산 및 이의 제조방법
KR19990022450A (ko)	1999-03-25	아릴설포닐아미노벤젠 유도체 및 엑스에이 인자 억제제로서의그 이용 방법
OA10718A (en)	2001-11-02	Hiv protease inhibitors
EP0763017B1 (en)	2000-09-13	N-(3-amino-2-hydroxybutyl)sulphonamide derivatives as hiv protease inhibitors
JP4336039B2 (ja)	2009-09-30	エポキシコハク酸アミド誘導体
CA2310331A1 (en)	1999-06-03	Biphenylamidine derivatives
ES2225104T3 (es)	2005-03-16	Compuestos de acido hidroxamico que contienen un alquinilo como inhibidores de la enzima tace.
JPH09509657A (ja)	1997-09-30	中間体および製造のための方法
US6001851A (en)	1999-12-14	HIV protease inhibitors
AP1358A (en)	2004-12-03	1-Aryl-2-Hydroxy-3-Isoquinoline Carboxamide HIV Protease Inhibitors, Their Preparation and Use.
JP2004513888A (ja)	2004-05-13	アミノ複素環式化合物（第Ｘａ因子阻害剤１４）
KR100522012B1 (ko)	2005-10-18	아미노산 유도체