UY23413A1 - PROCEDURE FOR THE PREPARATION OF AMINO ACID DERIVATIVES - Google Patents

PROCEDURE FOR THE PREPARATION OF AMINO ACID DERIVATIVES

Info

Publication number
UY23413A1
UY23413A1 UY23413A UY23413A UY23413A1 UY 23413 A1 UY23413 A1 UY 23413A1 UY 23413 A UY23413 A UY 23413A UY 23413 A UY23413 A UY 23413A UY 23413 A1 UY23413 A1 UY 23413A1
Authority
UY
Uruguay
Prior art keywords
formula
diastereoisomers
compound
separating
pharmaceutically acceptable
Prior art date
Application number
UY23413A
Other languages
Spanish (es)
Inventor
Joseph Armstrong Martin
Gareth John Thomas
Original Assignee
Hoffmann La Roche
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
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of UY23413A1 publication Critical patent/UY23413A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/62—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—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 carboxyl groups bound to the same carbon skeleton
    • C07C323/51—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—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 carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

Procedimiento para preparar derivados de aminoácido de fórmula general (I) (figura 1), y sales de adición de ácido farmacéuticamente aceptables, donde: R1 representa alcoxicarbonilo, alcanoilo, aralconoilo, heterociclilcarbonilo o un grupo de fórmula (i) (figura 2); R2 representa alquilo, cicloalquilalquilo o aralquilo; R3 representa hidrógeno, R4 hidroxilo, o tomados juntos representan oxo; el procedimiento se caracteriza por hacer reaccionar un compuesto de fórmula general (III) (figura 3), con un acilante que introduce un grupo R1, si se desea en presencia de un agente de condensación y una base, cuando el agente acilante introduce R1 de fórmula (i), y/o si se desea, separar una mezcla de racematos disatereoisoméricos en los racematos disatereoisoméricos o diastereoisómeros opticamente puros, y/o si se desea, separar una mezcla de diastereoisómeros en los diastereoisómeros opticamente puros, y/o si se desea, convertir un compuesto básico de fórmula (I) obtenido en una sal de adición de ácido farmacéuticamente aceptable. Ejemplo no limitante de compuesto preparado: 2(S)-[3(S)-[[N-(2-quinolilcarbonil)-L-asparaginil]amino]-2(R)-hidroxi-4-fenilbutil]-N-terci.butil-1(R)-ciclohexancarboxamida. Los compuestos preparados según la invención inhiben aspartil proteasas de origen viral y pueden utilizarse en la profilaxis y tratamientos de infecciones virales, particularmente HIV y otros retroides.Process for preparing amino acid derivatives of general formula (I) (figure 1), and pharmaceutically acceptable acid addition salts, where: R1 represents alkoxycarbonyl, alkanoyl, aralconoyl, heterocyclylcarbonyl or a group of formula (i) (figure 2); R2 represents alkyl, cycloalkylalkyl or aralkyl; R3 represents hydrogen, R4 hydroxyl, or taken together represent oxo; The process is characterized by reacting a compound of general formula (III) (figure 3), with an acylating agent that introduces a group R1, if desired in the presence of a condensing agent and a base, when the acylating agent introduces R1 of formula (i), and / or if desired, separating a mixture of disatheroisomeric racemates into the optically pure diastereoisomeric racemates or diastereoisomers, and / or if desired, separating a mixture of diastereoisomers into the optically pure diastereoisomers, and / or if You want to convert a basic compound of formula (I) obtained into a pharmaceutically acceptable acid addition salt. Non-limiting example of compound prepared: 2 (S) - [3 (S) - [[N- (2-quinolylcarbonyl) -L-asparaginyl] amino] -2 (R) -hydroxy-4-phenylbutyl] -N-tert .butyl-1 (R) -cyclohexanecarboxamide. The compounds prepared according to the invention inhibit aspartyl proteases of viral origin and can be used in the prophylaxis and treatment of viral infections, particularly HIV and other retroids.

UY23413A 1991-05-10 1992-05-08 PROCEDURE FOR THE PREPARATION OF AMINO ACID DERIVATIVES UY23413A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919110170A GB9110170D0 (en) 1991-05-10 1991-05-10 Amino acid derivatives
GB929203014A GB9203014D0 (en) 1991-05-10 1992-02-13 Amino acid derivatives

Publications (1)

Publication Number Publication Date
UY23413A1 true UY23413A1 (en) 1992-11-05

Family

ID=10694788

Family Applications (1)

Application Number Title Priority Date Filing Date
UY23413A UY23413A1 (en) 1991-05-10 1992-05-08 PROCEDURE FOR THE PREPARATION OF AMINO ACID DERIVATIVES

Country Status (8)

Country Link
KR (1) KR100220987B1 (en)
BR (1) BR9201771A (en)
GB (2) GB9110170D0 (en)
RU (1) RU2109731C1 (en)
TW (1) TW264462B (en)
UY (1) UY23413A1 (en)
YU (1) YU49092A (en)
ZA (1) ZA923184B (en)

Also Published As

Publication number Publication date
BR9201771A (en) 1992-12-29
GB9203014D0 (en) 1992-03-25
RU2109731C1 (en) 1998-04-27
GB9110170D0 (en) 1991-07-03
KR100220987B1 (en) 1999-10-01
ZA923184B (en) 1993-10-04
YU49092A (en) 1995-03-27
TW264462B (en) 1995-12-01
KR920021495A (en) 1992-12-18

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Legal Events

Date Code Title Description
VENC Patent expired

Effective date: 20130731