IL108696A - Pharmaceutical preparations containing castanospermine and dipeptide for the treatment of retroviral infections - Google Patents

Pharmaceutical preparations containing castanospermine and dipeptide for the treatment of retroviral infections

Info

Publication number: IL108696A
Authority: IL; Israel
Prior art keywords: benzyloxy; benzyl; compound; formula; compounds
Prior art date: 1993-02-22

Application number

IL10869694A

Other languages

English (en)

Hebrew (he)

Other versions

IL108696A0 (en

Original Assignee

Merrell Dow Pharma

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.)

1993-02-22

Filing date

1994-02-17

Publication date

1999-06-20

1994-02-17 Application filed by Merrell Dow Pharma filed Critical Merrell Dow Pharma

1994-05-30 Publication of IL108696A0 publication Critical patent/IL108696A0/xx

1999-06-20 Publication of IL108696A publication Critical patent/IL108696A/en

Links

238000011282 treatment Methods 0.000 title claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 title claims description 19
JDVVGAQPNNXQDW-TVNFTVLESA-N Castinospermine Chemical compound C1[C@H](O)[C@@H](O)[C@H](O)[C@H]2[C@@H](O)CCN21 JDVVGAQPNNXQDW-TVNFTVLESA-N 0.000 title abstract description 7
206010038997 Retroviral infections Diseases 0.000 title abstract description 5
JDVVGAQPNNXQDW-WCMLQCRESA-N Castanospermine Natural products O[C@H]1[C@@H](O)[C@H]2[C@@H](O)CCN2C[C@H]1O JDVVGAQPNNXQDW-WCMLQCRESA-N 0.000 title description 5
108010016626 Dipeptides Proteins 0.000 title description 2
-1 2-quinolylcarbonyl Chemical group 0.000 claims description 97
150000001875 compounds Chemical class 0.000 claims description 52
239000000203 mixture Substances 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 13
208000031886 HIV Infections Diseases 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
208000037357 HIV infectious disease Diseases 0.000 claims description 5
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
150000004677 hydrates Chemical class 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
230000002195 synergetic effect Effects 0.000 claims description 2
229940126062 Compound A Drugs 0.000 claims 3
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 3
LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 claims 1
208000030507 AIDS Diseases 0.000 abstract description 21
241000700605 Viruses Species 0.000 abstract description 12
241001430294 unidentified retrovirus Species 0.000 abstract description 9
201000010099 disease Diseases 0.000 abstract description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
108090000765 processed proteins & peptides Proteins 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 description 19
229910052736 halogen Chemical group 0.000 description 13
150000002367 halogens Chemical group 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
229940079593 drug Drugs 0.000 description 11
208000015181 infectious disease Diseases 0.000 description 11
238000000034 method Methods 0.000 description 11
125000001589 carboacyl group Chemical group 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 9
239000003112 inhibitor Substances 0.000 description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
239000003826 tablet Substances 0.000 description 9
206010001513 AIDS related complex Diseases 0.000 description 8
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
230000003612 virological effect Effects 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000000890 drug combination Substances 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
239000003599 detergent Substances 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
229960005235 piperonyl butoxide Drugs 0.000 description 6
230000001177 retroviral effect Effects 0.000 description 6
108090000288 Glycoproteins Proteins 0.000 description 5
102000003886 Glycoproteins Human genes 0.000 description 5
102100034349 Integrase Human genes 0.000 description 5
108091005804 Peptidases Proteins 0.000 description 5
239000004365 Protease Substances 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 5
125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 4
241000725303 Human immunodeficiency virus Species 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
102000035195 Peptidases Human genes 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
230000000840 anti-viral effect Effects 0.000 description 4
238000003556 assay Methods 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
229940099112 cornstarch Drugs 0.000 description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
231100000673 dose–response relationship Toxicity 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000002243 precursor Substances 0.000 description 4
238000012545 processing Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 3
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
102000004580 Aspartic Acid Proteases Human genes 0.000 description 3
108010017640 Aspartic Acid Proteases Proteins 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
108020004414 DNA Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
108010076039 Polyproteins Proteins 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
208000036142 Viral infection Diseases 0.000 description 3
ULXLHMVSQUDJFT-RJHNEXDJSA-N benzyl n-[(2s)-1-[[4,4-difluoro-5-[[(2r)-3-methyl-1-phenylmethoxybutan-2-yl]amino]-3,5-dioxo-1-(4-phenylmethoxyphenyl)pentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]carbamate Chemical compound C([C@@H](C(C)C)NC(=O)C(F)(F)C(=O)C(CC=1C=CC(OCC=2C=CC=CC=2)=CC=1)NC(=O)[C@@H](NC(=O)OCC=1C=CC=CC=1)C(C)C)OCC1=CC=CC=C1 ULXLHMVSQUDJFT-RJHNEXDJSA-N 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
230000002265 prevention Effects 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
230000010076 replication Effects 0.000 description 3
238000011160 research Methods 0.000 description 3
229920002477 rna polymer Polymers 0.000 description 3
QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
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208000011580 syndromic disease Diseases 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
230000009385 viral infection Effects 0.000 description 3
XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
108020004635 Complementary DNA Proteins 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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101710091045 Envelope protein Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
241000714260 Human T-lymphotropic virus 1 Species 0.000 description 2
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241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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101710188315 Protein X Proteins 0.000 description 2
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HTJGLYIJVSDQAE-VWNXEWBOSA-N [(1s,6s,7s,8r,8ar)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl] butanoate Chemical compound O[C@H]1[C@H](O)[C@@H](OC(=O)CCC)CN2CC[C@H](O)[C@@H]21 HTJGLYIJVSDQAE-VWNXEWBOSA-N 0.000 description 2
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PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 2
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125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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239000011777 magnesium Substances 0.000 description 2
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/55—Protease inhibitors
- 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
- 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

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Virology (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Immunology (AREA)
Gastroenterology & Hepatology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Tropical Medicine & Parasitology (AREA)
Molecular Biology (AREA)
AIDS & HIV (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

IL10869694A 1993-02-22 1994-02-17 Pharmaceutical preparations containing castanospermine and dipeptide for the treatment of retroviral infections IL108696A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB939303518A GB9303518D0 (en)	1993-02-22	1993-02-22	Combinations of retroviral inhibitors

Publications (2)

Publication Number	Publication Date
IL108696A0 IL108696A0 (en)	1994-05-30
IL108696A true IL108696A (en)	1999-06-20

Family

ID=10730826

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10869694A IL108696A (en)	1993-02-22	1994-02-17	Pharmaceutical preparations containing castanospermine and dipeptide for the treatment of retroviral infections

Country Status (14)

Country	Link
EP (1)	EP0684836A1 (fr)
JP (1)	JPH08509469A (fr)
KR (1)	KR100293299B1 (fr)
CN (1)	CN1118142A (fr)
AU (1)	AU679497B2 (fr)
CA (1)	CA2155129C (fr)
GB (1)	GB9303518D0 (fr)
HU (1)	HUT72493A (fr)
IL (1)	IL108696A (fr)
MX (1)	MXPA94001311A (fr)
NO (1)	NO307738B1 (fr)
NZ (1)	NZ261740A (fr)
WO (1)	WO1994019008A1 (fr)
ZA (1)	ZA941036B (fr)

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* Cited by examiner, † Cited by third party
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FR2889014A1 (fr)	2005-07-22	2007-01-26	Nextamp Sa	Procede et dispositif de tatouage d'horodates, procede et dispositif de decodage d'horodates, applications et produits programmes d'ordinateur correspondants

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Publication number	Priority date	Publication date	Assignee	Title
DE3526015A1 (de) *	1985-07-20	1987-01-22	Philips Patentverwaltung	Verfahren zum bestimmen der raeumlichen verteilung der streuquerschnitte fuer elastisch gestreute roentgenstrahlung und anordnung zur durchfuehrung des verfahrens
US5004746A (en) *	1987-09-29	1991-04-02	Merrell Dow Pharmaceuticals Inc.	Anti-retroviral castanospermine esters
US4999146A (en) *	1990-02-12	1991-03-12	Thermax Wire Corp.	Process for manufacture of low density polytetrofluoroethylene insulated cable
NZ241099A (en) *	1991-01-02	1994-08-26	Merrell Dow Pharma	Difluorostatone analogues and derivatives and pharmaceutical compositions

1993
- 1993-02-22 GB GB939303518A patent/GB9303518D0/en active Pending
1994
- 1994-01-18 HU HU9502451A patent/HUT72493A/hu unknown
- 1994-01-18 KR KR1019950703531A patent/KR100293299B1/ko not_active Expired - Fee Related
- 1994-01-18 NZ NZ261740A patent/NZ261740A/en unknown
- 1994-01-18 CN CN94191250A patent/CN1118142A/zh active Pending
- 1994-01-18 JP JP6518971A patent/JPH08509469A/ja not_active Ceased
- 1994-01-18 AU AU60918/94A patent/AU679497B2/en not_active Ceased
- 1994-01-18 CA CA002155129A patent/CA2155129C/fr not_active Expired - Fee Related
- 1994-01-18 EP EP94907268A patent/EP0684836A1/fr not_active Withdrawn
- 1994-01-18 WO PCT/US1994/000710 patent/WO1994019008A1/fr not_active Ceased
- 1994-02-15 ZA ZA941036A patent/ZA941036B/xx unknown
- 1994-02-17 IL IL10869694A patent/IL108696A/en not_active IP Right Cessation
- 1994-02-21 MX MXPA94001311A patent/MXPA94001311A/es unknown
1995
- 1995-08-21 NO NO953272A patent/NO307738B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1118142A (zh)	1996-03-06
GB9303518D0 (en)	1993-04-07
EP0684836A1 (fr)	1995-12-06
NO307738B1 (no)	2000-05-22
NO953272D0 (no)	1995-08-21
HUT72493A (en)	1996-05-28
NZ261740A (en)	1996-10-28
JPH08509469A (ja)	1996-10-08
AU679497B2 (en)	1997-07-03
CA2155129C (fr)	1999-04-13
HU9502451D0 (en)	1995-10-30
NO953272L (no)	1995-08-21
IL108696A0 (en)	1994-05-30
CA2155129A1 (fr)	1994-09-01
AU6091894A (en)	1994-09-14
KR100293299B1 (ko)	2001-09-17
MXPA94001311A (es)	2003-11-13
WO1994019008A1 (fr)	1994-09-01
KR960700743A (ko)	1996-02-24
ZA941036B (en)	1994-08-25

Legal Events

Date	Code	Title
1999-10-28	FF	Patent granted
2000-07-16	FF	Patent granted
2000-07-26	KB	Patent renewed
2004-05-12	KB	Patent renewed
2009-02-11	MM9K	Patent not in force due to non-payment of renewal fees
2010-04-14	MM9K	Patent not in force due to non-payment of renewal fees

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JPS6360936A (ja)	1988-03-17	複合薬剤
NO326292B1 (no)	2008-11-03	Sammensetning som omfatter castanosperminester og IFN-alfa, anvendelse av nevnte castanospeminester eller nevnte kombinasjon samt kit inneholdende nevnte kombinasjon
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AU679497B2 (en)	1997-07-03	Combinations of retroviral inhibitors
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EP1670448B1 (fr)	2007-11-21	Sulfonamides inhibant le hcv
US5063238A (en)	1991-11-05	Prevention of glycoprotein enveloped virus infectivity by pyridinyloxazole-2-ones
EP0543555A1 (fr)	1993-05-26	Flavonoides phosphorylés dans le traitement de maladies virales
TW393318B (en)	2000-06-11	Synergistic pharmaceutical composition for use in the treatment of retroviral infections
EP0428105B1 (fr)	1994-01-19	Utilisation de quinolyl- et isoquinolyloxazole-2-ones pour l'obtention d'un médicament destiné au prévention des infections par virus enveloppés par des glycoprotéines
EP0428103A2 (fr)	1991-05-22	Prévention des injections par virus enveloppés par des glycoprotéines avec des pyridyloxazole-2-ones
HK1004659B (en)	2003-10-10	Combination therapy for hiv infection using the hiv protease inhibitor indinavir and the reverse transcriptase inhibitor 3tc together with azt
ZA200309040B (en)	2005-05-27	HIV protease inhibitors, compositions containing the same, their pharmaceutical uses and materials for their synthesis.
JPH01180893A (ja)	1989-07-18	５−アミノ−６炭糖を含有する抗ウイルス剤