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DE69321845T2 - Hydroxyethylaminosulfonamide verwendbar als inhibitoren retroviraler proteasen - Google Patents

Hydroxyethylaminosulfonamide verwendbar als inhibitoren retroviraler proteasen

Info

Publication number
DE69321845T2
DE69321845T2 DE69321845T DE69321845T DE69321845T2 DE 69321845 T2 DE69321845 T2 DE 69321845T2 DE 69321845 T DE69321845 T DE 69321845T DE 69321845 T DE69321845 T DE 69321845T DE 69321845 T2 DE69321845 T2 DE 69321845T2
Authority
DE
Germany
Prior art keywords
radicals
compound according
amino
hydrogen
phenylmethyl
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
DE69321845T
Other languages
English (en)
Other versions
DE69321845D1 (en
Inventor
Gary Decrescenzo
John Freskos
Daniel Getman
Richard Mueller
John Talley
Michael Vazquez
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Co
GD Searle LLC
Original Assignee
Monsanto Co
GD Searle LLC
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.)
Filing date
Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25466397&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DE69321845(T2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Monsanto Co, GD Searle LLC filed Critical Monsanto Co
Application granted granted Critical
Publication of DE69321845D1 publication Critical patent/DE69321845D1/de
Publication of DE69321845T2 publication Critical patent/DE69321845T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • 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
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/11—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
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    • C07C311/14—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of rings other than six-membered aromatic rings
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    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • C07C311/32—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/41—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
    • C07C311/46—Y being a hydrogen or a carbon atom
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
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    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
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Claims (62)

1. Verbindung mit der Formel
oder ein pharmazeutisch unbedenkliches Salz, Prodrug oder Ester davon, worin
R Wasserstoff, Alkoxycarbonyl-, Aralkoxycarbonyl-, Alkylcarbonyl-, Cycloalkylcarbonyl-, Cycloalkylalkoxycarbonyl-, Cycloalkylalkanoyl-, Alkanoyl-, Aralkanoyl-, Aroyl-, Aryloxycarbonyl-, Aryloxycarbonylalkyl-, Aryloxyalkanoyl-, Heterocyclylcarbonyl-, Heterocyclyloxycarbonyl-, Heterocyclylalkanoyl-, Heterocyclylalkoxycarbonyl-, Heteroaralkanoyl-, Heteroaralkoxycarbonyl-, Heteroaryloxycarbonyl-, Heteroaroyl-, Alkyl-, Alkenyl-, Alkinyl-, Cycloalkyl-, Aryl-, Aralkyl-, Aryloxyalkyl-, Heteroaryloxyalkyl-, Hydroxyalkyl-, Aminocarbonyl-, Aminoalkanoyl- und mono- und disubstituierte Aminocarbonyl- und mono- und disubstituierte Aminoalkanoylreste, worin die Substituenten ausgewählt sind aus Alkyl-, Aryl-, Aralkyl-, Cycloalkyl-, Cycloalkylalkyl-, Heteroaryl-, Heteroaralkyl-, Heterocycloalkyl-, Heterocycloalkylalkylresten oder, wo die Aminocarbonyl- und Aminoalkanoylreste disubstituiert sind, diese Substituenten zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen Heterocycloalkyl- oder Heteroarylrest bilden, bedeutet;
R' Wasserstoff oder Reste, wie sie für R³ definiert sind, oder R"SO&sub2;-, worin R" Reste darstellt, wie sie für R³ definiert sind, bedeutet; oder R und R' zusammen mit dem Stickstoff, an den sie gebunden sind, einen Heterocycloalkyl- und Heteroarylrest darstellen;
R¹ Wasserstoff, -CH&sub2;SO&sub2;NH&sub2;, -CH&sub2;CO&sub2;CH&sub3;, -CO&sub2;CH&sub3;, -CONH&sub2;, -CH&sub2;C(O)NHCH&sub3;, -C(CH&sub3;)&sub2;(SH), -C(CH&sub3;)&sub2;(SCH&sub3;), -C(CH&sub3;)&sub2;(S[O]CH&sub3;), -C(CH&sub3;)&sub2;(S[O]&sub2;CH&sub3;), Alkyl-, Halogenalkyl-, Alkenyl-, Alkinyl- und Cycloalkylreste und Aminosäureseitenketten ausgewählt aus Asparagin-, S-Methylcystein- und Sulfoxid(SO)- und Sulfon(SO&sub2;)-Derivaten davon, Isoleucin-, Alloisoleucin-, Alanin-, Leucin-, tert-Leucin-, Phenylalanin-, Ornithin-, Histidin-, Norleucin-, Glutamin-, Threonin-, Glycin-, Allothreonin-, Serin-, O-Alkylserin-, Asparaginsäure-, beta-Cyanoalanin- und Valinseitenketten bedeutet;
R1' und R1" unabhängig Wasserstoff und Reste, wie sie für R¹ definiert sind, bedeuten, oder eines von R1' und R1" zusammen mit R¹ und den Kohlenstoffatomen, an die R¹, R1' und R1" gebun den sind, einen Cycloalkylrest darstellt;
R² Alkyl-, Aryl-, Cycloalkyl-, Cycloalkylalkyl- und Aralkylreste, welche Reste gegebenenfalls substituiert sind mit einer Gruppe ausgewählt aus Alkyl- und Halogenresten, -NO&sub2;, -C N, CF&sub3;, -OR&sup9;, -SR&sup9;, worin R&sup9; Wasserstoff und Alkylreste darstellt, bedeutet;
R³ Wasserstoff, Alkyl-, Halogenalkyl-, Alkenyl-, Alkinyl-, Hydroxyalkyl-, Alkoxyalkyl-, Cycloalkyl-, Cycloalkylalkyl-, Heterocycloalkyl-, Heteroaryl-, Heterocycloalkylalkyl-, Aryl-, Aralkyl-, Heteroaralkyl-, Aminoalkyl- und mono- und disubstituierte Aminoalkylreste, worin die Substituenten ausgewählt sind aus Alkyl-, Aryl-, Aralkyl-, Cycloalkyl-, Cycloalkylalkyl-, Heteroaryl-, Heteroaralkyl-, Heterocycloalkyl- und Heterocycloalkylalkylresten, oder, im Falle eines disubstituierten Aminoalkylrestes, die Substituenten zusammen mit dem Stickstoffatom, an das sie gebunden sind, einen Heterocycloalkyl- oder einen Heteroarylrest bilden, bedeutet;
R&sup4; Reste darstellt, wie sie durch R³ definiert sind, mit Ausnahme von Wasserstoff;
R&sup6; Wasserstoff und Alkylreste darstellt;
x für 0, 1 oder 2 steht;
t für 0 oder 1 steht; und
Y für O, S und NR¹&sup5; steht, wobei R¹&sup5; Wasserstoff und Reste, wie sie für R³ definiert sind, darstellt.
2. Verbindung nach Anspruch 1, worin t 0 ist, Y O ist, x 2 ist, R&sup6; = Wasserstoff und R' wie im Anspruch 1, außer R"SO&sub2;, mit R¹ wie im Anspruch 1 definiert, außer daß O-Alkylserin durch O-Methylserin ersetzt ist, mit R³ wie im Anspruch 1, außer Wasserstoff, mit R, R² und R&sup4; wie im Anspruch 1 definiert.
3. Verbindung nach Anspruch 2, worin R für Aralkoxycarbonyl- und Heteroaroylreste steht.
4. Verbindung nach Anspruch 2, worin R für Carbobenzoxy-, 2-Benzofurancarbonyl- und 2-Chinolinylcarbonylreste steht.
5. Verbindung nach Anspruch 2, worin R¹ Alkyl-, Alkinyl- und Alkenylreste und Aminosäureseitenketten ausgewählt aus der Gruppe bestehend aus Asparagin, Valin, Threonin, Allothreonin, Isoleucin, S-Methylcystein und Sulfon- und Sulfoxidderivaten davon, Alanin und Alloisoleucin darstellt.
6. Verbindung nach Anspruch 2, worin R¹ Methyl-, Propargyl-, t-Butyl-, Isopropyl- und sec-Butylreste und Aminosäureseitenketten ausgewählt aus der Gruppe bestehend aus Asparagin-, Valin-, S-Methylcystein-, Alloisoleucin-, Isoleucin-, Threonin-, Serin-, Asparaginsäure-, beta- Cyanoalanin- und Allothreoninseitenketten darstellt.
7. Verbindung nach Anspruch 2, worin R¹ Propargyl- und t-Butylreste darstellt.
8. Verbindung nach Anspruch 2, worin R&sup4; Phenyl- und substituierte Phenylreste darstellt und worin R³ n-Pentyl-, n-Hexyl-, n-Propyl-, i-Butyl-, Cyclohexyl-, Neopentyl-, i-Amyl- und n-Butylreste darstellt.
9. Verbindung nach Anspruch 2, worin R³ und R&sup4; unabhängig Alkylreste mit 2 bis 5 Kohlenstoff atomen, Cycloalkylalkylreste, Aralkylreste, Heterocycloalkylalkylreste oder Heteroaralkylreste darstellen.
10. Verbindung nach Anspruch 2, worin R³ Isobutyl-, n-Propyl-, n-Butyl-, Isoamyl-, Cyclohexyl-, Cyclohexylmethylreste darstellt und R&sup4; Phenyl- und substituierte Phenylreste darstellt.
11. Verbindung nach Anspruch 10, worin R³ i-Amyl oder i-Butyl ist und R&sup4; Phenyl oder substituiertes Phenyl ausgewählt aus p-Chlorphenyl, p-Fluorphenyl, p-Nitrophenyl, p-Aminophenyl und p-Methoxyphenyl darstellt.
12. Verbindung nach Anspruch 2, worin R&sup4; Heteroarylreste darstellt.
13. Verbindung nach Anspruch 2, worin R³ ein p-Fluorbenzylrest ist und R&sup4; ein Phenylrest oder substituierter Phenylrest ausgewählt aus p-Chlorphenyl, p-Fluorphenyl, p-Nitrophenyl, p-Aminophenyl und p-Methoxyphenyl ist.
14. Verbindung nach Anspruch 2, worin R³ ein 4-Pyridylmethylrest oder dessen N-Oxid ist und R&sup4; ein Phenylrest oder ein substituierter Phenylrest ausgewählt aus p-Chlorphenyl, p-Fluorphenyl, p-Nitrophenyl, p-Aminophenyl und p-Methoxyphenyl ist.
15. Verbindung nach Anspruch 2, worin R&sup4; einen Alkylrest mit 1 bis 6 Kohlenstoffatomen oder einen 5- oder 6-gliedrigen Heterocyclylrest, der gegebenenfalls mit einem Alkylrest mit 1 bis 3 Kohlenstoffatomen substituiert ist, darstellt.
16. Verbindung nach Anspruch 1, worin R1' und R1" beide Wasserstoff sind und R¹ -CH&sub2;SO&sub2;NH&sub2;, CO&sub2;NH&sub2;, CO&sub2;CH&sub3;, Alkyl- und Cycloalkylreste und Aminosäureseitenketten ausgewählt aus Asparagin-, S-Methylcystein- und den Sulfon- und Sulfoxidderivaten davon, Histidin-, Norleucin-, Glutamin-, Glycin-, Alloisoleucin-, Alanin-, Threonin-, Isoleucin-, Leucin-, tert-Leucin-, Phenylalanin-, Ornithin-, Allothreonin-, Serin-, Asparaginsäure-, beta-Cyanoalanin- und Valinseitenketten darstellt.
17. Verbindung nach Anspruch 3 oder 4, worin R¹ die Aminosäureseitenkette von Asparagin und R einen Heteroaroylrest darstellt.
18. Verbindung nach Anspruch 2, worin R¹ einen t-Butyl- oder einen Propargylrest oder eine Aminosäureseitenkette von Valin oder Isoleucin darstellt.
19. Verbindung nach Anspruch 18, worin R einen Arylalkanoyl-, Aryloxycarbonyl-, Alkanoyl-, Aminocarbonyl-, monosubstituierten Aminoalkanoyl- oder disubstituierten Aminoalkanoyl- oder Mono- oder Dialkylaminocarbonylrest darstellt.
20. Verbindung nach Anspruch 18, worin R Acetyl, N,N-Dimethylaminoacetyl, N-Methylaminoacetyl oder N-Benzyl-N-methylaminoacetyl darstellt.
21. Verbindung nach Anspruch 1, worin R¹ einen Methylrest darstellt.
22. Verbindung nach Anspruch 21, worin R einen Alkanoyl-, Arylalkanoyl-, Aryloxyalkanoyl- oder Arylalkyloxycarbonylrest darstellt.
23. Verbindung nach Anspruch 21, worin R einen Phenoxyacetyl-, 2-Naphthyloxyacetyl-, Benzyloxycarbonyl- oder p-Methoxybenzyloxycarbonylrest darstellt.
24. Verbindung nach Anspruch 21, worin R einen N,N-Dialkylaminocarbonylrest darstellt.
25. Verbindung nach Anspruch 21, worin R einen Aminocarbonyl- oder einen Alkylaminocarbonylrest darstellt.
26. Verbindung nach Anspruch 21, worin R einen N-Methylaminocarbonylrest darstellt.
27. Verbindung nach Anspruch 1, worin t = 1, R1' und R1" Wasserstoff sind, x 2 ist; Y O ist, R&sup6; Wasserstoff ist und worin R, R², R³, R&sup4; wie im Anspruch 1 definiert sind und R¹ wie im Anspruch 1 ist, außer O-Alkylserin, und R' wie im Anspruch 1 ist, außer R"SO&sub2;.
28. Verbindung nach Anspruch 27, worin R¹ Alkylreste mit 1 bis 4 Kohlenstoffatomen und Alkinylreste mit 3 bis 8 Kohlenstoffatomen darstellt.
29. Verbindung nach Anspruch 27, worin R¹ Methyl-, Ethyl-, Isopropyl-, Propargyl- und t-Butylreste darstellt.
30. Verbindung nach Anspruch 27, worin R' Wasserstoff ist und R
Gruppe, Acetyl, Phenoxyacetyl, 2-Naphthyloxycarbonyl, Benzyloxycarbonyl oder p-Methoxybenzyloxycarbonyl ist.
31. Verbindung nach Anspruch 27, worin R' Wasserstoff darstellt und R ein Aralkoxycarbonylrest oder ein Heteroaralkoxycarbonylrest ist.
32. Verbindung nach Anspruch 27, worin R und R' unabhängig aus Methyl- und Phenethylresten ausgewählt sind.
33. Verbindung nach Anspruch 27, worin R³ Alkylreste mit 2 bis 5 Kohlenstoffatomen und R&sup4; Methyl-, Phenyl- und substituierte Phenylreste darstellt.
34. Verbindung nach Anspruch 27, worin R³ Isobutyl-, n-Propyl-, n-Butyl-, Isoamyl-, Cyclohexylmethyl-, Cyclohexyl-, Benzyl-, p-Fluorbenzyl-, p-Methoxybenzyl-, p-Methylbenzyl- und 2-Naphthylmethylreste darstellt und R&sup4; Phenyl- und substituierte Phenylreste darstellt, worin die Substituenten des substituierten Phenylrestes aus Chlor-, Fluor-, Nitro-, Methoxy- und Aminosubstituenten ausgewählt sind.
35. Verbindung nach Anspruch 27, worin R³ Cyclohexylmethyl und R&sup4; Phenyl ist, oder R³ i-Amyl und R&sup4; Phenyl ist, oder R³ i-Butyl und R&sup4; Phenyl ist, oder R³ n-Butyl und R&sup4; Phenyl ist, oder R³ Cyclohexyl und R&sup4; Phenyl ist.
36. Verbindung nach Anspruch 27, worin R&sup4; Methyl- oder Cyclohexylreste darstellt.
37. Verbindung nach Anspruch 27, worin R und R' zusammen mit dem Stickstoff, an den sie gebunden sind, Pyrrolidinyl-, Piperidinyl-, Morpholinyl- und Piperazinylreste darstellen.
38. Verbindung nach Anspruch 27, worin R³ Heteroaralkylreste darstellt und R&sup4; Methyl oder Phenyl ist.
39. Verbindung nach Anspruch 1, worin t = 1, x = 2, Y für O steht, R&sup6; Wasserstoff ist und worin R, R¹, R1", R², R&sup4; wie im Anspruch 1 definiert sind und worin R³ wie im Anspruch 1 ist, außer Wasserstoff, und R¹ wie im Anspruch 1 ist, außer O-Alkylserin, und worin R' wie im Anspruch 1 ist, außer R"SO&sub2;.
40. Verbindung nach Anspruch 39, worin R' Wasserstoff darstellt und R Aralkoxycarbonyl- und Heteroaroylreste darstellt.
41. Verbindung nach Anspruch 39, worin R' Wasserstoff ist und R für Carbobenzoxy-, 2-Benzofurancarbonyl- und 2-Chinolinylcarbonylreste steht.
42. Verbindung nach Anspruch 39, worin R¹, R1', und R1" unabhängig Wasserstoff und Alkylreste mit 1 bis etwa 4 Kohlenstoffatomen, Alkenyl-, Alkinyl-, Aralkylreste und Reste ausgewählt aus -CH&sub2;SO&sub2;NH&sub2;, -CO&sub2;CH&sub3;, -CONHCH&sub3;, -CON(CH&sub3;)&sub2;, -CH&sub2;C(O)NHCH&sub3;, -CH&sub2;C(O)N(CH&sub3;)&sub2;, -CONH&sub2;, -C(CH&sub3;)&sub2;(SCH&sub3;), -C(CH&sub3;)&sub2;(S[O]CH&sub3;) und -C(CH&sub3;)&sub2;(S[O]CH&sub3;) darstellen.
43. Verbindung nach Anspruch 39, worin R¹, R1' und R1" unabhängig Wasserstoff, Methyl, Ethyl, Benzyl, Phenylpropyl, Propargyl, Hydroxyl und Reste ausgewählt aus -C(O)OCH&sub3;, -C(O)NH&sub2;, -C(O)OH darstellen.
44. Verbindung nach Anspruch 39, worin R¹ und R1' beide Wasserstoff sind und R1" C(O)NH&sub2; ist.
45. Verbindung nach Anspruch 39, worin R¹ und R1' beide Wasserstoff sind und R1" Methyl ist.
46. Verbindung nach Anspruch 39, worin R1' Wasserstoff ist und R¹ und R1" zusammen mit den Kohlenstoffatomen, an die sie gebunden sind, einen 3- bis 6-gliedrigen Cycloalkylrest bilden.
47. Verbindung nach Anspruch 44, worin R Carbobenzoxy-, 2-Chinolinylcarbonyl- und 2-Benzofurancarbonylreste darstellt.
48. Verbindung nach Anspruch 39, worin R³ Alkylreste mit 2 bis 5 Kohlenstoffatomen darstellt.
49. Verbindung nach Anspruch 39, worin R³ unabhängig n-Propyl-, i-Butyl-, Cyclohexyl-, Cyclohexylmethyl-, i-Amyl- und n-Butylreste darstellt und R&sup4; Phenyl- und substituierte Phenylreste darstellt.
50. Verbindung nach Anspruch 39, worin R³ und R&sup4; unabhängig Alkylreste mit 2 bis 5 Kohlenstoffatomen, Cycloalkylalkylreste, Arylreste, Heteroarylreste, Aralkylreste, Heterocycloalkylalkylreste und Heteroaralkylreste darstellen.
51. Verbindung nach Anspruch 39, worin R³ Benzyl-, p-Fluorbenzyl-, p-Methoxybenzyl-, p-Methylbenzyl- und 2-Naphthylmethylreste darstellt und R&sup4; Phenyl- und substituierte Phenylreste darstellt, wobei die Substituenten der substituierten Phenylreste ausgewählt sind aus Chlor-, Fluor-, Nitro-, Methoxy- und Aminosubstituenten.
52. Verbindung nach Anspruch 2, 27 oder 39, worin R² Alkyl-, Cycloalkylalkylreste darstellt, welche Reste gegebenenfalls substituiert sind mit Halogenresten und Resten, die dargestellt werden durch die Formel -OR&sup9; und -SR&sup9;, worin R&sup9; Wasserstoff und Alkylreste darstellt.
53. Verbindung nach Anspruch 2, 27 oder 39, worin R² CH&sub3;SCH&sub2;CH&sub2;-, Isobutyl, n-Butyl-, Benzyl-, 2-Naphthylmethyl- und Cyclohexylmethylreste darstellt.
54. Verbindung nach Anspruch 2, 27 oder 39, worin R³ und R&sup4; unabhängig Alkyl-, Halogenalkyl-, Alkenyl-, Alkoxyalkyl-, Cycloalkyl-, Cycloalkylalkyl-, Heterocycloalkyl-, Heterocycloalkylalkyl-, Heteroaryl-, Aryl-, Aralkyl- und Heteroaralkyireste darstellen.
55. Verbindung nach Anspruch 2, 27 oder 39, worin R³ Alkyl- und Alkenylreste darstellt und R&sup4; Arylreste darstellt.
56. Pharmazeutische Zusammensetzung, umfassend eine Verbindung nach irgendeinem der Ansprüche 1, 2, 27 oder 39 und einen pharmazeutisch unbedenklichen Träger.
57. Verwendung einer Zusammensetzung nach Anspruch 56 zur Herstellung eines Medikaments zur Hemmung einer retroviralen Protease.
58. Verwendung nach Anspruch 57, worin die retrovirale Protease HIV-Protease ist.
59. Verwendung einer Zusammensetzung nach Anspruch 56 zur Herstellung eines Medikaments zur Behandlung einer retroviralen Infektion.
60. Verwendung nach Anspruch 59, worin die retrovirale Infektion eine HIV-Infektion ist.
61. Verwendung einer Zusammensetzung nach Anspruch 56 zur Herstellung eines Medikaments zur Behandlung von AIDS.
62. Verbindung nach Anspruch 1, welche ist:
Phenylmethyl[2R-hydroxy-3-[(3-methylbutyl)(methylsulfonyl)amino]-1S-(phenylmethyl)propyl]carbamat;
Phenylmethyl[2R-hydroxy-3-[(3-methylbutyl)(phenylsulfonyl)amino]-1S-(phenylmethyl)propyl]carbamat;
N1-[2R-Hydroxy-3-[(3-methylbutyl)(methylsulfonyl)amino]-1S-(phenylmethyl)propyl]-2S-[(2-chinolinylcarbonyl)amino]butandiamid;
N1-[2R-Hydroxy-3-[(3-methylbutyl)(methylsulfonyl)amino]-1S-(phenylmethyl)propyl]-2S-[(phenylmethyloxycarbonyl)amino]butandiamid;
N1-[2R-Hydroxy-3-[(3-methylbutyl)(phenylsulfonyl)amino]-1S-(phenylmethyl)propyl]-2S-[(2-chinolinylcarbonyl)amino]butandiamid;
N1-[2R-Hydroxy-3-[(3-methylbutyl)(phenylsulfonyl)amino]-1S-(phenylmethyl)propyl]-2S-[(phenylmethyloxycarbonyl)amino]butandiamid;
2S-[[(Dimethylamino)acetyl]amino]-N-[2R-hydroxy-3-[(3-methylbutyl)(phenylsulfonyl)amino]-1S- (phenylmethyl)propyl]-3,3-dimethylbutanamid;
2S-[[(Methylamino)acetyl]amino]-N-[2R-hydroxy-3-[(3-methylbutyl)(phenylsulfonyl)amino]-1S- (phenylmethyl)propyl]-3,3-dimethylbutanamid; oder
N1-[2R-Hydroxy-3-[(3-methylbutyl)(phenylsulfonyl)amino]-N4-methyl-1S-(phenylmethyl)propyl]- 2S-[(2-chinolinylcarbonyl)amino]butandiamid; oder
Carbaminsäure, [3-[[2-Hydroxy-3-[(3-methylbutyl)(phenylsulfonyl)amino]-1-(phenylmethyl)propyl]amino]-2-methyl-3-oxopropyl]-, (4-Methoxyphenyl)methylester, [1S-[1R*(S*),2S*]]-.
DE69321845T 1992-08-25 1993-08-24 Hydroxyethylaminosulfonamide verwendbar als inhibitoren retroviraler proteasen Expired - Lifetime DE69321845T2 (de)

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DE200712000045 Active DE122007000045I2 (de) 1992-08-25 1993-08-24 Darunavir oder pharmazeutisch vertragliche Salze, Hydroxyethylaminosulfonamide verwendbar als InhibiEster oder Prodrugs davon. toren retroviraler Proteasen.

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Families Citing this family (110)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040122000A1 (en) 1981-01-07 2004-06-24 Vertex Pharmaceuticals Incorporated. Inhibitors of aspartyl protease
US6878728B1 (en) 1999-06-11 2005-04-12 Vertex Pharmaceutical Incorporated Inhibitors of aspartyl protease
US7141609B2 (en) 1992-08-25 2006-11-28 G.D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US5463104A (en) * 1992-08-25 1995-10-31 G. D. Searle & Co. Succinoylamino hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US5968942A (en) * 1992-08-25 1999-10-19 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
WO1994004492A1 (en) * 1992-08-25 1994-03-03 G.D. Searle & Co. Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US6046190A (en) * 1992-08-25 2000-04-04 G.D. Searle & Co. Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
KR100296462B1 (ko) * 1992-08-25 2001-10-24 죤 에이치. 뷰센 레트로바이러스프로테아제억제제로서유용한술포닐알칸오일아미노히드록시에틸아미노술폰아미드
IS2334B (is) 1992-09-08 2008-02-15 Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) Aspartyl próteasi hemjari af nýjum flokki súlfonamíða
US5723490A (en) * 1992-09-08 1998-03-03 Vertex Pharmaceuticals Incorporated THF-containing sulfonamide inhibitors of aspartyl protease
US5783701A (en) * 1992-09-08 1998-07-21 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
US5846993A (en) * 1992-12-22 1998-12-08 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
US5484926A (en) * 1993-10-07 1996-01-16 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
ES2127938T3 (es) * 1993-08-24 1999-05-01 Searle & Co Hidroxietilamino sulfonamidas utiles como inhibidores de proteasas retroviricas.
MX9603909A (es) * 1994-03-07 1997-03-29 Vertex Pharma Derivados de sulfonamida como inhibidores de proteasa aspartilo.
US5527829A (en) * 1994-05-23 1996-06-18 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
EP0804428B1 (de) 1995-01-20 2007-12-26 G.D. Searle LLC. Bis-sulfonamid-hydroxyethylamino-derivate als inhibitoren retroviraler proteasen
US5831117A (en) 1995-01-20 1998-11-03 G. D. Searle & Co. Method of preparing retroviral protease inhibitor intermediates
US5756533A (en) * 1995-03-10 1998-05-26 G.D. Searle & Co. Amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US6140505A (en) 1995-03-10 2000-10-31 G. D. Searle & Co. Synthesis of benzo fused heterocyclic sulfonyl chlorides
US6861539B1 (en) 1995-03-10 2005-03-01 G. D. Searle & Co. Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
PL184771B1 (pl) * 1995-03-10 2002-12-31 Searle & Co Związek stanowiący hydroksyetyloaminosulfonamid pirolidynokarbonyloaminokwasu, kompozycja zawierająca ten związek, jego zastosowanie do wytwarzania kompozycji do leczenia infekcji retrowirusowej i sposób zapobiegania replikacji retrowirusa in vitro
US5776971A (en) * 1995-03-10 1998-07-07 G.D. Searle & Co. Heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US6150556A (en) * 1995-03-10 2000-11-21 G. D. Dearle & Co. Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US6407134B1 (en) 1995-03-10 2002-06-18 G. D. Searle & Co. Heterocyclecarbonyl amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US7339078B2 (en) 1995-03-10 2008-03-04 G.D. Searle Llc Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors
US6143788A (en) * 1995-03-10 2000-11-07 G.D. Searle & Co. Bis-amino acid hydroxyethlamino sulfonamide retroviral protease inhibitors
EP1188766A1 (de) 1995-03-10 2002-03-20 G.D. Searle & Co. Verbindungen der Struktur bis-Aminosäure-Hydroxyethylamino-Sulfonamid als Inhibitoren der retroviralen Protease
US5691372A (en) * 1995-04-19 1997-11-25 Vertex Pharmaceuticals Incorporated Oxygenated-Heterocycle containing sulfonamide inhibitors of aspartyl protease
US6004957A (en) * 1995-06-07 1999-12-21 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
PT861233E (pt) * 1995-11-16 2000-09-29 Searle & Co Beta-amino-hidroxissulfonatos n-protegidos/n-substituidos
US6730679B1 (en) 1996-03-22 2004-05-04 Smithkline Beecham Corporation Pharmaceutical formulations
NZ333099A (en) 1996-06-25 2000-06-23 Glaxo Group Ltd synergistic combinations comprising 141W94, zidovudine and 3TC for use in the treatment of HIV
US5705647A (en) * 1996-09-05 1998-01-06 Agouron Pharmaceuticals, Inc. Intermediates for making HIV-protease inhibitors
US5962725A (en) 1996-09-05 1999-10-05 Agouron Pharmaceuticals, Inc. Intermediate compounds useful for making HIV protease inhibitors such as nelfinavir
US5925759A (en) 1996-09-05 1999-07-20 Agouron Pharmaceuticals, Inc. Methods of making HIV-protease inhibitors and intermediates for making HIV-protease inhibitors
US6001851A (en) * 1997-03-13 1999-12-14 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
US6084107A (en) * 1997-09-05 2000-07-04 Agouron Pharmaceuticals, Inc. Intermediates for making HIV-protease inhibitors
US6436989B1 (en) * 1997-12-24 2002-08-20 Vertex Pharmaceuticals, Incorporated Prodrugs of aspartyl protease inhibitors
GB9805898D0 (en) * 1998-03-20 1998-05-13 Glaxo Group Ltd Process for the sythesis of hiv protease inhibitors
BR9912169A (pt) * 1998-06-19 2001-04-10 Vertex Pharma Inibidores de sulfonamida de protease de aspartil
DK1088098T4 (en) 1998-06-23 2015-09-14 Us Of America Represented By The Secretary Dept Of Health And Human Services Fitnessassay and methods for reducing HIV resistance to therapy
EP1095022A1 (de) 1998-07-08 2001-05-02 G.D. Searle & Co. Inhibitoren von retoviraler protease
SK9522001A3 (en) * 1999-01-13 2002-03-05 Du Pont Pharm Co Bis-amino acid sulfonamides containing n-terminally a substituted benzyl group as hiv protease inhibitors
EP1159278B1 (de) * 1999-02-12 2005-11-30 Vertex Pharmaceuticals Incorporated Aspartyl-protease-inhibitoren
TNSN00027A1 (fr) * 1999-02-12 2005-11-10 Vertex Pharma Inhibiteurs de l'aspartyle protease
AR031520A1 (es) * 1999-06-11 2003-09-24 Vertex Pharma Un compuesto inhibidor de aspartilo proteasa, una composicion que lo comprende y un metodo para tratar un paciente con dicha composicion
ATE398623T1 (de) * 1999-10-06 2008-07-15 Tibotec Pharm Ltd Hexahydrofuro-2,3-b furan-3-yl-n- 3-,(1,3- benzodioxol-5-ylsulfonyl)(isobutyl)amino -1- benzyl-2-hydroxypropyl carbamat als retrovirusproteasehemmer
US6391919B1 (en) 2000-01-12 2002-05-21 Bristol-Myers Squibb Pharma Company Bis-amino acid sulfonamides containing substituted benzyl amines HIV protease inhibitors
JP2003528071A (ja) 2000-03-23 2003-09-24 エラン ファーマスーティカルズ インコーポレイテッド アルツハイマー病治療用組成物および方法
US6992081B2 (en) 2000-03-23 2006-01-31 Elan Pharmaceuticals, Inc. Compounds to treat Alzheimer's disease
WO2002002505A2 (en) 2000-06-30 2002-01-10 Elan Pharmaceuticals, Inc. Compounds to treat alzheimer's disease
PE20020276A1 (es) 2000-06-30 2002-04-06 Elan Pharm Inc COMPUESTOS DE AMINA SUSTITUIDA COMO INHIBIDORES DE ß-SECRETASA PARA EL TRATAMIENTO DE ALZHEIMER
EP1666452A2 (de) 2000-06-30 2006-06-07 Elan Pharmaceuticals, Inc. Verbindungen zur Behandlung der Alzheimerischen Krankheit
US20030096864A1 (en) * 2000-06-30 2003-05-22 Fang Lawrence Y. Compounds to treat alzheimer's disease
US6846813B2 (en) * 2000-06-30 2005-01-25 Pharmacia & Upjohn Company Compounds to treat alzheimer's disease
US6617310B2 (en) 2000-07-19 2003-09-09 Bristol-Myers Squibb Pharma Company Phosphate esters of bis-amino acid sulfonamides containing substituted benzyl amines
EA006096B1 (ru) 2001-02-14 2005-08-25 Тиботек Фармасьютикалз Лтд. Ингибиторы протеазы вич широкого спектра действия на основе сульфонамидов 2-(замещенных-амино)бензотиазолов
WO2003002122A1 (en) 2001-06-27 2003-01-09 Elan Pharmaceuticals, Inc. Beta-hydroxyamine derivatives useful in treatment of alzheimer's disease
US20070213407A1 (en) * 2001-06-29 2007-09-13 Elan Pharmaceuticals And Pharmacia & Upjohn Company Llc Compounds to treat Alzheimer's disease
US6562848B1 (en) * 2001-09-18 2003-05-13 Bristol-Myers Squibb Company Bis-amino acid sulfonamides as HIV protease inhibitors
CA2462851A1 (en) 2001-10-04 2003-04-10 Elan Pharmaceuticals, Inc. Hydroxypropylamines
WO2003040390A2 (en) * 2001-11-08 2003-05-15 Tibotec Pharmaceuticals Ltd. Protease assay for therapeutic drug monitoring
CA2467749A1 (en) * 2001-11-19 2003-05-30 Elan Pharmaceuticals, Inc. (4-phenyl) piperidin-3-yl-phenylcarboxylate derivatives and related compounds as beta-secretase inhibitors for the treatment of alzheimer's disease
WO2003050062A2 (en) * 2001-12-11 2003-06-19 Wyeth PRODUCTION OF CHIRALLY PURE α-AMINO ACIDS ADN N-SULFONYL α-AMINO ACIDS
CA2473231A1 (en) * 2002-01-07 2003-08-07 Sequoia Pharmaceuticals Resistance-repellent retroviral protease inhibitors
US7157489B2 (en) * 2002-03-12 2007-01-02 The Board Of Trustees Of The University Of Illinois HIV protease inhibitors
MY142238A (en) * 2002-03-12 2010-11-15 Tibotec Pharm Ltd Broadspectrum substituted benzimidazole sulfonamide hiv protease inhibitors
AU2003303141A1 (en) * 2002-04-30 2004-07-22 Elan Pharmaceuticals, Inc. Hydroxypropyl amides for the treatment of alzheimer's disease
WO2003097616A1 (en) * 2002-05-17 2003-11-27 Tibotec Pharmaceuticals Ltd Broadspectrum substituted benzisoxazole sulfonamide hiv protease inhibitors
US7294642B2 (en) * 2002-09-06 2007-11-13 Elan Pharmaceuticals, Inc. 1,3-Diamino-2-hydroxypropane pro-drug derivatives
GB0228410D0 (en) 2002-12-05 2003-01-08 Glaxo Group Ltd Novel Compounds
GB0310593D0 (en) * 2003-05-08 2003-06-11 Leuven K U Res & Dev Peptidic prodrugs
GB0314476D0 (en) * 2003-06-20 2003-07-23 Glaxo Group Ltd Compounds
US7273533B2 (en) * 2003-11-19 2007-09-25 Tokyo Electron Limited Plasma processing system with locally-efficient inductive plasma coupling
US8193227B2 (en) * 2003-12-11 2012-06-05 Abbott Laboratories HIV protease inhibiting compounds
US20050131042A1 (en) * 2003-12-11 2005-06-16 Flentge Charles A. HIV protease inhibiting compounds
ME01059B (me) 2003-12-23 2012-10-20 Janssen Sciences Ireland Uc Proces za pripremanje (3r,3as,6ar)-heksahidrofuro [2,3-b] furan-3-il (1s,2r)-3-[[(4-aminofenil) sulfonil] (izobutil) amino]-1-benzil-2- hidroksipropilkarbamata
CA2559328A1 (en) 2004-03-11 2005-09-22 Sequoia Pharmaceuticals, Inc. Resistance-repellent retroviral protease inhibitors
AU2005244121B2 (en) * 2004-05-07 2012-01-19 Sequoia Pharmaceuticals, Inc. Resistance-repellent retroviral protease inhibitors
WO2006104646A1 (en) * 2005-03-11 2006-10-05 Smithkline Beecham Corporation Hiv protease inhibitors
US20110178092A1 (en) * 2005-06-22 2011-07-21 Akbar Ali HIV-1 Protease Inhibitors
US8106090B2 (en) 2005-07-20 2012-01-31 Eli Lilly And Company 1-amino linked compounds
EP2064177B1 (de) * 2006-09-21 2017-04-05 TaiMed Biologics, Inc. Proteasehemmer
JP2010525029A (ja) 2007-04-27 2010-07-22 テイボテク・フアーマシユーチカルズ・リミテツド Ｎ−イソブチル−ｎ−（２−ヒドロキシ−３−アミノ−４−フェニルブチル）−ｐ−ニトロベンゼンスルホニルアミド誘導体の製造方法
KR20100092424A (ko) * 2007-07-30 2010-08-20 아디아 바이오사이언스즈 인크. 다형체를 포함하는, ｍｅｋ의 억제제로서의 ｎ-(아릴아미노) 술폰아미드의 유도체 및 조성물, 사용 방법 및 이의 제조 방법
WO2009055006A1 (en) * 2007-10-26 2009-04-30 Concert Pharmaceuticals, Inc. Deuterated darunavir
US8592487B2 (en) 2007-10-26 2013-11-26 Concert Pharmaceuticals, Inc. Deuterated darunavir
US8759379B2 (en) * 2008-01-04 2014-06-24 Gilead Sciences, Inc. Inhibitors of cytochrome P450
US8921415B2 (en) 2009-01-29 2014-12-30 Mapi Pharma Ltd. Polymorphs of darunavir
US20100305173A1 (en) * 2009-04-30 2010-12-02 Concert Pharmaceuticals, Inc. Hydroxyethylamino sulfonamide derivatives
US9062065B2 (en) 2009-10-30 2015-06-23 Lupin Limited Process for preparation of darunavir and darunavir ethanolate of fine particle size
WO2011061590A1 (en) 2009-11-17 2011-05-26 Hetero Research Foundation Novel carboxamide derivatives as hiv inhibitors
AU2011210349A1 (en) 2010-01-28 2012-07-05 Mapi Pharma Limited Process for the preparation of darunavir and darunavir intermediates
GB201118182D0 (en) 2011-10-21 2011-12-07 Jagotec Ag Improvements in or relating to organic compounds
EP2804869B1 (de) 2012-01-18 2019-06-12 Aurobindo Pharma Limited Neuartige solvate von darunavir
WO2014016660A2 (en) 2012-07-24 2014-01-30 Laurus Labs Private Limited A process for preparation of darunavir
MX2016002560A (es) 2013-08-29 2016-10-26 Teva Pharma Forma de dosificacion unitaria que comprende emtricitabina, tenofovir, darunavir y ritonavir y un comprimido monolitico que comprende darunavir y ritonavir.
TW201622731A (zh) 2014-04-08 2016-07-01 泰瓦藥品工業有限公司 包含恩曲他濱（Ｅｍｔｒｉｃｉｔａｂｉｎｅ）、替諾福韋（Ｔｅｎｏｆｏｖｉｒ）、地瑞那韋（Ｄａｒｕｎａｖｉｒ）及利托那韋（Ｒｉｔｏｎａｖｉｒ）之單位劑型以及包含地瑞那韋及利托那韋之單層錠劑
US20160075643A1 (en) 2014-09-16 2016-03-17 Zcl Chemicals Limited Novel process to prepare intermediates of hiv-protease inhibitors thereof
WO2016069955A1 (en) 2014-10-29 2016-05-06 Wisconsin Alumni Research Foundation Boronic acid inhibitors of hiv protease
US20180162870A1 (en) 2015-06-05 2018-06-14 Amneal Pharmaceuticals Company Gmbh Process for the Preparation of Darunavir
EP3496718A4 (de) 2016-08-08 2020-01-22 Hetero Labs Limited Antiretrovirale zusammensetzungen
EP3496719B1 (de) 2016-08-08 2023-06-14 Hetero Labs Limited Antiretrovirale zusammensetzung mit mehreren klassen
WO2018081292A1 (en) 2016-10-27 2018-05-03 Gilead Sciences, Inc. Crystalline forms of darunavir free base, hydrate, solvates and salts
CN108558808B (zh) * 2018-05-22 2020-05-05 中国医学科学院医药生物技术研究所 一种酰胺类衍生物或其药学上可接受的盐及其制备方法和应用
CN111205206B (zh) * 2020-02-13 2021-10-22 中国医学科学院医药生物技术研究所 一种包含氨基酸连接链的羰基化合物或其药学上可接受的盐及其制备方法和应用
US12083099B2 (en) 2020-10-28 2024-09-10 Accencio LLC Methods of treating symptoms of coronavirus infection with viral protease inhibitors
CN113277991B (zh) * 2021-02-03 2022-07-12 中国医学科学院医药生物技术研究所 一种含氮杂环氨基衍生物及其制备方法和一种抗hiv-1的药物
CN116693595A (zh) * 2023-06-07 2023-09-05 中国医学科学院医药生物技术研究所 一种雷公藤甲素衍生物及其制备方法和应用

Family Cites Families (110)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE264795C (de) *
US725A (en) 1838-05-04 Cabbiage-spbing
GB1435386A (en) 1973-07-26 1976-05-12 Made Labor Sa Cyanoglutaric acid derivatives
DE2352452A1 (de) 1973-10-19 1975-04-30 Made Labor Sa 2-cyan-3-dialcoximethyl-alkylglutarate sowie verfahren zur herstellung dieser verbindungen und ihrer derivate
JPS5041814Y1 (de) 1975-03-06 1975-11-27
US5142056A (en) 1989-05-23 1992-08-25 Abbott Laboratories Retroviral protease inhibiting compounds
EP0068378B1 (de) 1981-06-26 1986-03-05 Schering Corporation Imidazo(1,2-a)pyridine und -pyrazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
DE3377497D1 (en) 1982-09-15 1988-09-01 Haessle Ab Enzyme inhibitors
US4668770A (en) 1982-12-27 1987-05-26 Merck & Co., Inc. Renin inhibitory tripeptides
EP0114993B1 (de) 1982-12-27 1990-05-16 Merck & Co. Inc. Reninhemmende Tripeptide
FI843837A0 (fi) 1983-02-07 1984-09-28 Ferring Ab Enzyminhibitorer.
JPS59227851A (ja) * 1983-06-09 1984-12-21 Sankyo Co Ltd レニン阻害作用を有するペプチド類
US4514391A (en) 1983-07-21 1985-04-30 E. R. Squibb & Sons, Inc. Hydroxy substituted peptide compounds
US4477441A (en) 1983-09-14 1984-10-16 Merck & Co., Inc. Renin inhibitors containing a C-terminal disulfide cycle
US4645759A (en) 1984-06-22 1987-02-24 Abbott Laboratories Renin inhibiting compounds
US4616088A (en) 1984-10-29 1986-10-07 E. R. Squibb & Sons, Inc. Amino acid ester and amide renin inhibitor
EP0222889B1 (de) 1985-05-15 1993-10-27 Amoco Corporation Cytidinanaloga
US4826815A (en) 1985-05-17 1989-05-02 Abbott Laboratories Renin inhibiting compounds
US4599198A (en) 1985-08-02 1986-07-08 Pfizer Inc. Intermediates in polypeptide synthesis
US4668769A (en) 1985-08-02 1987-05-26 Hoover Dennis J Oxa- and azahomocyclostatine polypeptides
CA1282549C (en) 1985-11-12 1991-04-02 Eric M. Gordon Aminocarbonyl renin inhibitors
US4757050A (en) * 1985-12-23 1988-07-12 E. R. Squibb Sons, Inc. Ureido renin inhibitors
CA1297631C (en) 1985-12-23 1992-03-17 Sesha I. Natarajan Ureido renin inhibitors
US4757060A (en) * 1986-03-04 1988-07-12 Bristol-Myers Company Non-steroidal anti-inflammatory compositions protected against gastrointestinal injury with a combination of certain H1 and H2, receptor blockers
US4880938A (en) 1986-06-16 1989-11-14 Merck & Co., Inc. Amino acid analogs
DE3635109A1 (de) 1986-10-15 1988-04-21 Patent Treuhand Ges Fuer Elektrische Gluehlampen Mbh Schaltungsanordnung zum betrieb von niedervolt-halogengluehlampen
DE3635907A1 (de) * 1986-10-22 1988-04-28 Merck Patent Gmbh Hydroxy-aminosaeurederivate
CH676988A5 (de) 1987-01-21 1991-03-28 Sandoz Ag
USH725H (en) 1987-02-26 1990-01-02 E. R. Squibb & Sons, Inc. Ureido amino and imino acids, compositions and methods for use
GB8707412D0 (en) 1987-03-27 1987-04-29 Fujisawa Pharmaceutical Co Peptide compounds
USH1649H (en) 1987-07-31 1997-05-06 Barrish; Joel C. HIV protease inhibitor combinations
DE3830825A1 (de) 1987-09-15 1989-03-23 Sandoz Ag Hydrophile reninhemmer, ihre herstellung und verwendung
CA1328333C (en) * 1988-03-04 1994-04-05 Quirico Branca Amino acid derivatives
IL89900A0 (en) 1988-04-12 1989-12-15 Merck & Co Inc Hiv protease inhibitors useful for the treatment of aids and pharmaceutical compositions containing them
US4977277A (en) 1988-05-09 1990-12-11 Abbott Laboratories Functionalized peptidyl aminodiols and -triols 4-amino-5-cyclohexyl-3-hydroxy-1,2-oxopentane and derivatives thereof
IL90218A0 (en) 1988-05-13 1989-12-15 Abbott Lab Retroviral protease inhibitors
DE3816890A1 (de) * 1988-05-18 1989-11-30 Schaeffler Waelzlager Kg Ausruecklagereinrichtung fuer eine gedrueckte kraftfahrzeugkupplung
CA1340588C (en) 1988-06-13 1999-06-08 Balraj Krishan Handa Amino acid derivatives
IL91307A0 (en) 1988-08-24 1990-03-19 Merck & Co Inc Hiv protease inhibitors and pharmaceutical compositions for the treatment of aids containing them
US5268374A (en) * 1988-10-04 1993-12-07 Abbott Laboratories Non-peptide renin inhibitors
IL91780A (en) * 1988-10-04 1995-08-31 Abbott Lab History of the amine of the xenon-preventing xanine acid, the process for their preparation and the pharmaceutical preparations containing them
DE3840289A1 (de) * 1988-11-30 1990-05-31 Merck Patent Gmbh Aminosaeurederivate
US4969530A (en) * 1989-03-03 1990-11-13 Kopczynski John F All-terrain vehicle
CA2012306A1 (en) 1989-03-28 1990-09-28 Werner Neidhart Amino acid derivatives
CA2012901A1 (en) * 1989-04-05 1990-10-05 Quirico Branca Amino acid derivatives
JP2701932B2 (ja) * 1989-04-10 1998-01-21 サントリー株式会社 タンパク質分解酵素阻害剤
DE3912829A1 (de) 1989-04-19 1990-10-25 Bayer Ag Verwendung von renininhibitorischen peptiden als mittel gegen retroviren
US5552558A (en) 1989-05-23 1996-09-03 Abbott Laboratories Retroviral protease inhibiting compounds
EP0428849A3 (en) 1989-09-28 1991-07-31 Hoechst Aktiengesellschaft Retroviral protease inhibitors
GB8927913D0 (en) 1989-12-11 1990-02-14 Hoffmann La Roche Amino acid derivatives
CA2032259A1 (en) 1989-12-18 1991-06-19 Wayne J. Thompson Hiv protease inhibitors useful for the treatment of aids
US5122514A (en) * 1990-04-23 1992-06-16 Abbott Laboratories Psoriasis treatment
US5272268A (en) * 1990-06-28 1993-12-21 Shionogi & Co., Ltd. Dipeptide derivatives
US5223615A (en) * 1990-06-28 1993-06-29 Shionogi & Co., Ltd. Dipeptide derivatives
TW225540B (de) 1990-06-28 1994-06-21 Shionogi & Co
JPH05508855A (ja) 1990-07-06 1993-12-09 スミスクライン・ビーチャム・コーポレイション レトロウイルスプロテアーゼ阻害剤
GB9024938D0 (en) 1990-11-16 1991-01-02 Process Dev Ltd Filtering
ATE296624T1 (de) 1990-11-19 2005-06-15 Monsanto Co Retrovirusprotease inhibitoren
DK0558673T3 (da) * 1990-11-19 1996-07-29 Monsanto Co Retrovirale proteaseinhibitorer
US5475013A (en) 1990-11-19 1995-12-12 Monsanto Company Retroviral protease inhibitors
CA2120925A1 (en) 1991-10-11 1993-04-15 Patrick Yuk-Sun Lam Substituted cyclic carbonyls and derivatives thereof useful as retroviral protease inhibitors
WO1993008184A1 (en) 1991-10-23 1993-04-29 Merck & Co., Inc. Hiv protease inhibitors
US5413999A (en) 1991-11-08 1995-05-09 Merck & Co., Inc. HIV protease inhibitors useful for the treatment of AIDS
NZ244986A (en) 1991-11-08 1995-10-26 Merck & Co Inc Hiv protease inhibitor and pharmaceutical compositions
ATE116640T1 (de) 1992-03-13 1995-01-15 Bio Mega Boehringer Ingelheim Substituierte pipecoline-säurederivate als hiv- protease-hemmer.
KR100290516B1 (ko) 1992-05-20 2001-09-17 죤 에이치. 뷰센 레트로바이러스프로테아제억제인자의합성에유용한중간생성물의제조방법
US5559256A (en) 1992-07-20 1996-09-24 E. R. Squibb & Sons, Inc. Aminediol protease inhibitors
US7141609B2 (en) * 1992-08-25 2006-11-28 G.D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
KR100296462B1 (ko) 1992-08-25 2001-10-24 죤 에이치. 뷰센 레트로바이러스프로테아제억제제로서유용한술포닐알칸오일아미노히드록시에틸아미노술폰아미드
US5463104A (en) 1992-08-25 1995-10-31 G. D. Searle & Co. Succinoylamino hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US6046190A (en) 1992-08-25 2000-04-04 G.D. Searle & Co. Hydroxyethylamino sulphonamides useful as retroviral protease inhibitors
US6022994A (en) 1992-08-25 2000-02-08 G. D. Searle &. Co. Succinoylamino hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US5968942A (en) 1992-08-25 1999-10-19 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
WO1994004492A1 (en) 1992-08-25 1994-03-03 G.D. Searle & Co. Hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
US5830897A (en) 1992-08-27 1998-11-03 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
AU4812393A (en) 1992-09-03 1994-03-29 Biochem Pharma Inc. Use of rapamycin in the treatment of aids
IS2334B (is) * 1992-09-08 2008-02-15 Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) Aspartyl próteasi hemjari af nýjum flokki súlfonamíða
US5723490A (en) 1992-09-08 1998-03-03 Vertex Pharmaceuticals Incorporated THF-containing sulfonamide inhibitors of aspartyl protease
US5783701A (en) 1992-09-08 1998-07-21 Vertex Pharmaceuticals, Incorporated Sulfonamide inhibitors of aspartyl protease
US6869925B1 (en) 1992-09-09 2005-03-22 Amgen Inc. Inhibition of retrovirus infection
US5376633A (en) 1992-09-30 1994-12-27 Lezdey; John Method for deactivating viruses in blood component containers
US5578606A (en) 1992-10-30 1996-11-26 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonyl urea derivatives useful as retroviral protease inhibitors
US5484926A (en) 1993-10-07 1996-01-16 Agouron Pharmaceuticals, Inc. HIV protease inhibitors
US5514801A (en) 1992-12-29 1996-05-07 Monsanto Company Cyclic sulfone containing retroviral protease inhibitors
AU6828894A (en) 1993-05-14 1994-12-12 Merck & Co., Inc. Hiv protease inhibitors
ES2127938T3 (es) 1993-08-24 1999-05-01 Searle & Co Hidroxietilamino sulfonamidas utiles como inhibidores de proteasas retroviricas.
US5567592A (en) 1994-02-02 1996-10-22 Regents Of The University Of California Screening method for the identification of bioenhancers through the inhibition of P-glycoprotein transport in the gut of a mammal
UA49803C2 (uk) 1994-06-03 2002-10-15 Дж.Д. Сьорль Енд Ко Спосіб лікування ретровірусних інфекцій
US5691372A (en) 1995-04-19 1997-11-25 Vertex Pharmaceuticals Incorporated Oxygenated-Heterocycle containing sulfonamide inhibitors of aspartyl protease
GB9509321D0 (en) 1995-05-09 1995-06-28 Zylepsis Ltd Methods of and substances for inhibiting oxidative enzymes
US6037157A (en) 1995-06-29 2000-03-14 Abbott Laboratories Method for improving pharmacokinetics
KR980009238A (ko) 1995-07-28 1998-04-30 우에노 도시오 설포닐아미노산 유도체
CN1209875A (zh) 1996-01-26 1999-03-03 维科公司 根据人类hiv病毒株的表型药物敏感性控制hiv阳性病人化疗的方法
US5837464A (en) 1996-01-29 1998-11-17 Virologic, Inc. Compositions and methods for determining anti-viral drug susceptibility and resistance and anti-viral drug screening
PL328068A1 (en) 1996-01-29 1999-01-04 Virologic Compositions for and methods of determining susceptibility to and immunity against an antiviral drug and selecting appropriate antiviral drug
US6191165B1 (en) 1996-05-31 2001-02-20 Allelix Neuroscience Inc. Pharmaceutical for treatment of neurological and neuropsychiatric disorders
AU4159997A (en) 1996-08-22 1998-03-06 Northwestern University Process of determining the efficacy of drug treatment in hiv infected subjects
US6245809B1 (en) 1996-12-09 2001-06-12 Cor Therapeutics Inc. Integrin antagonists
CO4940492A1 (es) 1997-05-29 2000-07-24 Merck & Co Inc Inhibidor de proteasa de vih
GB9712253D0 (en) 1997-06-13 1997-08-13 Glaxo Group Ltd Antiviral compound
WO1999033792A2 (en) 1997-12-24 1999-07-08 Vertex Pharmaceuticals Incorporated Prodrugs os aspartyl protease inhibitors
GB9805898D0 (en) 1998-03-20 1998-05-13 Glaxo Group Ltd Process for the sythesis of hiv protease inhibitors
US6251874B1 (en) 1998-03-26 2001-06-26 Research Institute For Genetic And Human Therapy (R.I.G.H.T.) Method of inhibiting human immunodeficiency virus using hydroxurea and a reverse transcriptase inhibitor in vivo
DK1088098T4 (en) 1998-06-23 2015-09-14 Us Of America Represented By The Secretary Dept Of Health And Human Services Fitnessassay and methods for reducing HIV resistance to therapy
EP1095022A1 (de) 1998-07-08 2001-05-02 G.D. Searle & Co. Inhibitoren von retoviraler protease
BR0011555A (pt) 1999-05-28 2002-02-26 Virco Nv Perfis mutacionais em transcriptase reversa de hiv-1 correlacionada com resistência fenotìpica à droga
GB9913079D0 (en) 1999-06-04 1999-08-04 Novartis Ag Organic compounds
US6869759B1 (en) 1999-06-22 2005-03-22 Virologic, Inc. Means and methods for monitoring protease inhibitor antiretroviral therapy and guiding therapeutic decisions in the treatment of HIV/AIDS
US6943170B2 (en) 2002-11-14 2005-09-13 Bristol-Myers Squibb Company N-cycloalkylglycines as HIV protease inhibitors
US6890942B2 (en) 2003-05-16 2005-05-10 Bristol-Myers Squibb Company Acyl sulfonamides as inhibitors of HIV integrase

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