PE20010517A1 - THE EFFICIENT SYNTHETIC ROUTES FOR THE PREPARATION OF RINOVIRUS PROTEASE INHIBITORS AND KEY INTERMEDIATES - Google Patents
THE EFFICIENT SYNTHETIC ROUTES FOR THE PREPARATION OF RINOVIRUS PROTEASE INHIBITORS AND KEY INTERMEDIATESInfo
- Publication number
- PE20010517A1 PE20010517A1 PE2000000854A PE0008542000A PE20010517A1 PE 20010517 A1 PE20010517 A1 PE 20010517A1 PE 2000000854 A PE2000000854 A PE 2000000854A PE 0008542000 A PE0008542000 A PE 0008542000A PE 20010517 A1 PE20010517 A1 PE 20010517A1
- Authority
- PE
- Peru
- Prior art keywords
- compound
- alkyl
- rinovirus
- preparation
- produce
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
- B01J19/2435—Loop-type reactors
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2475—Membrane reactors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00074—Controlling the temperature by indirect heating or cooling employing heat exchange fluids
- B01J2219/00087—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor
- B01J2219/00099—Controlling the temperature by indirect heating or cooling employing heat exchange fluids with heat exchange elements outside the reactor the reactor being immersed in the heat exchange medium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
- B01J2219/00159—Controlling the temperature controlling multiple zones along the direction of flow, e.g. pre-heating and after-cooling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Enzymes And Modification Thereof (AREA)
- Pyrrole Compounds (AREA)
- Peptides Or Proteins (AREA)
Abstract
SE REFIERE A UN PROCESO PARA LA SINTESIS DEL COMPUESTO I COMO ETILO-3-{(5`-METILISOXAZOL-3'-CARBONIL)-L-VALÝ(COCH2)-L-(4-F-Phe)-L-((S)-PIRROL-ALA)}-E-PROPANOATO, QUE COMPRENDE a)LA CIANOMETILACION DE UN COMPUESTO V UTILIZANDO BIS(TRIMETISILO)AMIDA Y BROMOACETONITRILO PARA PRODUCIR UN COMPUESTO VI; b)REALIZAR LA DISMINUCION , CICLIZACION, PROTECCION DEL COMPUESTO VI PARA PRODUCIR EL COMPUESTO VII; c)REALIZAR LA OXIDACION Y OLEFINACION DEL COMPEUSTO VII MEDIANTE LA REACCION DEL COMPUESTO VII CON UN COMPLEJO DE SO3-PIRIDINA PARA PRODUCIR UNA MEZCLA DE REACCION Y REACCIONAR CON UN COMPUESTO VIII Y FORMAR UN COMPUESTO IV; R1 ES H, F, ALQUILO, OH, SH, O-ALQUILO; R41 ES H, ALQUILO; X ES GRUPO PROTECTOR DE N; d)DESPROTEGER EL COMPUESTO IV PARA FORMAR UN COMPUESTO IVA; e)SOMETER (R4)(R5)(R6)C-C(=O)-OH Y EL COMPUESTO IVA PARA FORMAR EL COMPUESTO IA, R2 Y R3 SON H, -CH2-CO-NH2, GRUPO a; n ES 0-5; A1 ES CH, N; A2 Y A3 SON C(R41)2, S, ENTRE OTROS; R4 ES R9-CO-NH-C(R7)(R8)-CO-; R5 Y R6 SON H, F, ALQUILO, ENTRE OTROS: R7 Y R8 SON H, ALQUILO, ENTRE OTROS; R9 ES HETEROCICLO DE 5 MIEMBROS; Z Y Z1 SON H, F, ALQUILO, ENTRE OTROS. EL COMPUESTO V ES PREPARADO A PARTIR DE N-BOS L-ACIDO GLUTAMICO þ-BENZILO ESTER. TAMBIEN SE REFIERE A LA PREPARACION DE COMPUESTOS INTERMEDIOS. EL COMPUESTO ES UTIL PARA PREPARAR INHIBIDORES DE PROTEASA DEL RINOVIRUSREFERS TO A PROCESS FOR THE SYNTHESIS OF COMPOUND I AS ETHYL-3 - {(5`-METHYLISOXAZOLE-3'-CARBONYL) -L-VALÝ (COCH2) -L- (4-F-Phe) -L - (( S) -PYRROL-ALA)} - E-PROPANOATE, WHICH INCLUDES a) THE CYANOMETILATION OF A COMPOUND V USING BIS (TRIMETISILO) AMIDE AND BROMOACETONITRILE TO PRODUCE A COMPOUND VI; b) PERFORM THE DECREASE, CYCLING, PROTECTION OF COMPOUND VI TO PRODUCE COMPOUND VII; c) CARRY OUT THE OXIDATION AND OLEFINATION OF THE COMPEUST VII BY REACTIONING THE COMPOUND VII WITH A SO3-PYRIDINE COMPLEX TO PRODUCE A REACTION MIXTURE AND REACT WITH A COMPOUND VIII AND FORM A COMPOUND IV; R1 IS H, F, ALKYL, OH, SH, O-ALKYL; R41 IS H, ALKYL; X IS THE PROTECTIVE GROUP OF N; d) UNPROTECT COMPOUND IV TO FORM A COMPOUND VAT; e) SUBMIT (R4) (R5) (R6) C-C (= O) -OH AND THE COMPOUND IVA TO FORM THE COMPOUND IA, R2 AND R3 ARE H, -CH2-CO-NH2, GROUP a; n IS 0-5; A1 IS CH, N; A2 AND A3 ARE C (R41) 2, S, AMONG OTHERS; R4 IS R9-CO-NH-C (R7) (R8) -CO-; R5 AND R6 ARE H, F, ALKYL, AMONG OTHERS: R7 AND R8 ARE H, ALKYL, AMONG OTHERS; R9 IS A 5-MEMBER HETEROCYCLE; Z AND Z1 ARE H, F, RENT, AMONG OTHERS. COMPOUND V IS PREPARED FROM N-BOS L-GLUTAMIC ACID þ-BENZYL ESTER. IT ALSO REFERS TO THE PREPARATION OF INTERMEDIATE COMPOUNDS. THE COMPOUND IS USEFUL TO PREPARE RINOVIRUS PROTEASE INHIBITORS
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15035899P | 1999-08-24 | 1999-08-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
PE20010517A1 true PE20010517A1 (en) | 2001-05-16 |
Family
ID=22534156
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PE2000000854A PE20010517A1 (en) | 1999-08-24 | 2000-08-22 | THE EFFICIENT SYNTHETIC ROUTES FOR THE PREPARATION OF RINOVIRUS PROTEASE INHIBITORS AND KEY INTERMEDIATES |
Country Status (20)
Country | Link |
---|---|
EP (1) | EP1206450A1 (en) |
JP (1) | JP2003507453A (en) |
KR (1) | KR20020046283A (en) |
CN (1) | CN1168713C (en) |
AR (1) | AR025380A1 (en) |
AU (1) | AU770221B2 (en) |
BR (1) | BR0013306A (en) |
CA (1) | CA2376452A1 (en) |
CO (1) | CO5200782A1 (en) |
CZ (1) | CZ2002632A3 (en) |
HK (1) | HK1049336B (en) |
HU (1) | HUP0203365A3 (en) |
IL (1) | IL147674A0 (en) |
MX (1) | MXPA02001944A (en) |
PE (1) | PE20010517A1 (en) |
PL (1) | PL353997A1 (en) |
TW (1) | TWI245040B (en) |
UY (1) | UY26307A1 (en) |
WO (1) | WO2001014329A1 (en) |
ZA (1) | ZA200200504B (en) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUP0400624A2 (en) | 1998-04-30 | 2004-06-28 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds, their preparation and use |
CA2380647A1 (en) | 1999-08-04 | 2001-02-15 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis |
PA8507801A1 (en) | 1999-12-03 | 2002-08-26 | Agouron Pharma | ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS, THEIR PHARMACEUTICAL USES AND THE MATERIALS FOR SYNTHESIS |
PE20011277A1 (en) | 2000-04-14 | 2002-01-07 | Agouron Pharma | ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS, THEIR PHARMACEUTICAL USES AND THE MATERIALS FOR THEIR SYNTHESIS |
JP2004503533A (en) | 2000-06-14 | 2004-02-05 | アグロン・ファーマシュウティカルズ・インコーポレーテッド | Anti-picornavirus compounds and compositions, their pharmaceutical use, and substances for their synthesis |
CN1309712C (en) * | 2004-04-02 | 2007-04-11 | 中国科学院上海有机化学研究所 | Precursor of key intermediate of AG 7088 class compound and its sythetic process |
US20230157998A1 (en) | 2020-03-06 | 2023-05-25 | Pfizer Inc. | Methods of Inhibiting SARS-CoV-2 Replication and Treating Corona Virus Disease 2019 |
CN115260074A (en) * | 2022-08-02 | 2022-11-01 | 爱斯特(成都)生物制药股份有限公司 | Preparation method of Paxlovid intermediate of oral antiviral drug |
CN115322130B (en) * | 2022-08-02 | 2024-05-14 | 南京正济医药研究有限公司 | Preparation of (S) -2- (BOC-amino) -3- [ (S) -2-oxo-3-pyrrolidinyl ] propanoic acid methyl ester |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GT199700061A (en) * | 1996-05-14 | 1998-11-04 | PROCEDURE FOR OBTAINING "ANTIPICORNAVIRAL COMPOUNDS AND METHODS FOR USE AND PREPARATION". | |
ES2206907T3 (en) * | 1997-03-28 | 2004-05-16 | Agouron Pharmaceuticals, Inc. | ANTI-PICORNAVIRUS COMPOUNDS, COMPOSITIONS CONTAINING THESE COMPOUNDS AND THEIR USE PROCEDURES. |
US5962487A (en) * | 1997-12-16 | 1999-10-05 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds and methods for their use and preparation |
HUP0400624A2 (en) * | 1998-04-30 | 2004-06-28 | Agouron Pharmaceuticals, Inc. | Antipicornaviral compounds, their preparation and use |
-
2000
- 2000-08-22 PE PE2000000854A patent/PE20010517A1/en not_active Application Discontinuation
- 2000-08-23 CZ CZ2002632A patent/CZ2002632A3/en unknown
- 2000-08-23 BR BR0013306-0A patent/BR0013306A/en not_active IP Right Cessation
- 2000-08-23 UY UY26307A patent/UY26307A1/en not_active Application Discontinuation
- 2000-08-23 JP JP2001518419A patent/JP2003507453A/en active Pending
- 2000-08-23 EP EP00955831A patent/EP1206450A1/en not_active Withdrawn
- 2000-08-23 KR KR1020027002322A patent/KR20020046283A/en not_active Application Discontinuation
- 2000-08-23 WO PCT/US2000/023033 patent/WO2001014329A1/en not_active Application Discontinuation
- 2000-08-23 AU AU67971/00A patent/AU770221B2/en not_active Ceased
- 2000-08-23 CN CNB008118779A patent/CN1168713C/en not_active Expired - Fee Related
- 2000-08-23 PL PL00353997A patent/PL353997A1/en not_active Application Discontinuation
- 2000-08-23 IL IL14767400A patent/IL147674A0/en unknown
- 2000-08-23 CA CA002376452A patent/CA2376452A1/en not_active Abandoned
- 2000-08-23 HU HU0203365A patent/HUP0203365A3/en unknown
- 2000-08-23 MX MXPA02001944A patent/MXPA02001944A/en active IP Right Grant
- 2000-08-24 CO CO00063457A patent/CO5200782A1/en not_active Application Discontinuation
- 2000-08-24 AR ARP000104401A patent/AR025380A1/en unknown
- 2000-10-24 TW TW089117083A patent/TWI245040B/en active
-
2002
- 2002-01-21 ZA ZA200200504A patent/ZA200200504B/en unknown
-
2003
- 2003-02-27 HK HK03101461.5A patent/HK1049336B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
CO5200782A1 (en) | 2002-09-27 |
CZ2002632A3 (en) | 2003-04-16 |
HUP0203365A3 (en) | 2003-12-29 |
WO2001014329A1 (en) | 2001-03-01 |
EP1206450A1 (en) | 2002-05-22 |
PL353997A1 (en) | 2003-12-15 |
HK1049336B (en) | 2005-05-20 |
AU770221B2 (en) | 2004-02-19 |
UY26307A1 (en) | 2001-04-30 |
KR20020046283A (en) | 2002-06-20 |
MXPA02001944A (en) | 2002-10-31 |
HUP0203365A2 (en) | 2003-02-28 |
CA2376452A1 (en) | 2001-03-01 |
BR0013306A (en) | 2002-05-28 |
AU6797100A (en) | 2001-03-19 |
TWI245040B (en) | 2005-12-11 |
ZA200200504B (en) | 2003-03-26 |
IL147674A0 (en) | 2002-08-14 |
JP2003507453A (en) | 2003-02-25 |
CN1374947A (en) | 2002-10-16 |
CN1168713C (en) | 2004-09-29 |
AR025380A1 (en) | 2002-11-20 |
HK1049336A1 (en) | 2003-05-09 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FD | Application declared void or lapsed |