cas 259221-77-7, CYCLOPROPANECARBOXYLIC ACID, 1-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-2-ETHENYL-, (1S,2S)-

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MACROCYCLIC SERINE PROTEASE INHIBITORS
Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula Ia or Ib, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.
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Paragraph 0224

(2017/05/31)

HCV NS3 protease inhibitors
The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.
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Page/Page column 94

(2016/06/01)

Macrocyclic compounds for suppressing replication of hepatitis C virus
A compound as represented by Formula (I) is provided, wherein groups are defined in the description. The compound is used as HCV protease inhibitor for treating HCV infection.
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Page/Page column 41

(2016/05/24)

Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base
Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained α-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step SN2 and SN2′ alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.
Kawashima, Aki,Shu, Shuangjie,Takeda, Ryosuke,Kawamura, Akie,Sato, Tatsunori,Moriwaki, Hiroki,Wang, Jiang,Izawa, Kunisuke,Acea, Jos Luis,Soloshonok, Vadim A.,Liu, Hong
p. 973 - 986
(2016/04/04)

COMPOUNDS AS HEPATITIS C INHIBITORS AND USES THEREOF IN MEDICINE
Provided herein are compounds as hepatitis C inhibitors and uses thereof in medicine. Specifically, provided herein is a compound of Formula (I) or a stereoisomer, a tautomer, an enantiomer, an N-oxide, a hydrate, a solvate, a metabolite, a pharmaceutically acceptable salt or a prodrug thereof, which can be used for treating HCV infection or hepatitis C diseases. Also provided herein are a pharmaceutically acceptable composition containing such compound and a method of treating HCV infection or hepatitis C diseases comprising administering the compound or pharmaceutical composition thereof disclosed herein.
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Paragraph 00175

(2016/09/22)

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID
Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.
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Paragraph 0487-0490

(2016/05/10)

Preparation method for alpha-amino acid
The invention provides a preparation method for an alpha-amino acid and belongs to the pharmaceutical technical field. The preparation method comprises the following steps: in the presence of an alkali, performing a reaction of a metal complex in an organic solvent to obtain a complex; and then hydrolyzing the complex and/or reacting with a protecting agent to obtain the alpha-amino acid or derivatives thereof. The method provided by the invention can simply obtain the amino acid or derivatives thereof without splitting the product, so that the yield is high, the cost is low, and industrial production is facilitated.
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Paragraph 0114; 0115; 0116; 0117; 0123

(2016/10/09)

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID
Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.
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Paragraph 0842; 0844

(2016/11/17)

Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by sequential SN2-SN2′ dialkylation of (R)-N-(benzyl)proline-derived glycine Schiff base Ni(ii) complex
This work describes a new process for the asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid of high pharmaceutical importance. The sequence of the reactions includes PTC alkylation (SN2), homogeneous SN2′ cyclization followed by disassembly of the resultant Ni(ii) complex. All reactions are conducted under operationally convenient conditions and suitably scaled up to 6 g of the starting Ni(ii) complex. This journal is
Kawashima, Aki,Xie, Chen,Mei, Haibo,Takeda, Ryosuke,Kawamura, Akie,Sato, Tatsunori,Moriwaki, Hiroki,Izawa, Kunisuke,Han, Jianlin,Acea, Jos Luis,Soloshonok, Vadim A.
p. 1051 - 1058
(2015/02/02)

HCV NS3 PROTEASE INHIBITORS
The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.
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Page/Page column 73

(2013/06/05)

HCV NS3 PROTEASE INHIBITORS
The present invention is directed to compounds, compositions and methods for treating or preventing HCV viral infections in human patients or other animal hosts.
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Page/Page column 24

(2013/07/25)

NOVEL SPECIFIC HCV NS3 PROTEASE INHIBITORS
The present invention is directed to compounds, compositions and methods for treating or preventing viral infections, in particular, HCV in human patients or other animal hosts.
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Page/Page column 24

(2012/05/20)

HCV PROTEASE INHIBITORS
This invention relates to macrocyclic compounds of formula (I) shown in the specification. These compounds can be used to treat hepatitis C virus infection.
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Page/Page column 55-59

(2011/04/18)

HCV PROTEASE INHIBITORS
This invention relates to macrocyclic compounds shown in the specification. These compounds can be used to treat hepatitis C virus infection.
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Page/Page column 34

(2011/04/19)

MACROCYCLIC SERINE PROTEASE INHIBITORS USEFUL AGAINST VIRAL INFECTIONS, PARTICULARLY HCV
Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula (Ia) or (Ib), pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.
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Page/Page column 130

(2011/02/24)

OPTICALLY ACTIVE VINYL-CYCLOPROPANE CARBOXYLIC ACID DERIVATIVE AND OPTICALLY ACTIVE VINYL-CYCLOPROPANE AMINO ACID DERIVATIVE MANUFACTURING METHOD
The objective of the present invention is to provide a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative with high yield and high optical purity using a safe material available at low cost. In addition, the objective of the present invention is to provide a method for safely-obtaining an optically active vinylcyclopropaneamino acid with high optical purity at low cost. The problems can be solved by a method for obtaining an optically active vinylcyclopropanecarboxylic acid derivative, which method contains the step of reacting a racemic vinylcyclopropanecarboxylic acid derivative with an optically active amine compound, to obtain a diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative - amine compound. In addition, it is possible to obtain a vinylcyclopropaneamino acid by deriving the vinylcyclopropaneamino acid from thus obtained diastereomer salt of optically active vinylcyclopropanecarboxylic acid derivative - amine compound.
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Page/Page column 12-13

(2011/08/04)

THERAPEUTIC ANTIVIRAL PEPTIDES
Disclosed herein are compounds represented by a formula: Therapeutic methods, compositions, medicaments, and dosage forms related thereto are also disclosed.
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(2010/06/11)

Titanium-catalyzed cyclopropanation of Boc-protected cyanohydrins: A short access to aminocyclopropanecarboxylic acid derivatives
The preparation of protected 1-aminocyclopropanecarboxylic acid was performed from readily available and inexpensive starting materials, using titanium-catalyzed cyclopropanation as the key step. As an extension of this methodology, a diastereoselective synthesis of the cis-2-vinyl-substituted analogue is presented. Georg Thieme Verlag Stuttgart.
Pearson-Long, Morwenna S.M.,Beauseigneur, Alice,Karoyan, Philippe,Szymoniak, Jan,Bertus, Philippe
experimental part
p. 3410 - 3414
(2010/11/19)

MACROCYCLIC SERINE PROTEASE INHIBITORS
Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula Ia or Ib, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.
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(2010/11/03)

Antiviral compounds
The invention is related to anti-viral compounds, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.
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Page/Page column 33-34

(2009/03/07)

HCV PROTEASE INHIBITORS
This invention relates to macrocyclic compounds of formula (I) or (II) shown in the specification. These compounds can be used to treat hepatitis C virus infection.
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Page/Page column 16-17

(2009/12/05)

Hepatitis C Virus Inhibitors
Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 26-27

(2009/12/02)

MACROCYCLIC SERINE PROTEASE INHIBITORS
Provided herein are macrocyclic serine protease inhibitor compounds, for example, of Formula I, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof
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(2009/08/18)

NOVEL MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS REPLICATION
The embodiments provide compounds of the general Formulae I, II, III, IV, V, VI, VII, and X, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.
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(2009/10/31)

Inhibitors of Hepatitis C Virus
Macrocyclic peptides are disclosed having the general formula: wherein R3, R3′, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 21

(2008/12/04)

Hepatitis C Virus Inhibitors
Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 33-34

(2008/06/13)

MACROCYCLIC PEPTIDES AS HEPATITIS C VIRUS INHIBITORS
Macrocyclic peptides having the general formula (I): are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 64-65

(2008/12/05)

Inhibitors of Hepatitis C Virus
Macrocyclic peptides are disclosed having the general formula: wherein R3, R3′, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 31

(2008/12/04)

Inhibitors of Hepatitis C Virus
Macrocyclic peptides are disclosed having the general formula: wherein R3, R′3, R4, R6, R′, X, Q and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 32

(2008/12/04)

Hepatitis C Virus Inhibitors
Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 35-36

(2008/12/05)

MACROCYCLIC PEPTIDES AS HEPATITIS C VIRUS INHIBITORS
Macrocyclic peptides having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 62

(2008/12/05)

Hepatitis C virus inhibitors
Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 46

(2010/11/26)

Hepatitis C virus inhibitors
Macrocyclic peptides are disclosed having the general formula: wherein R′, R3, R3′, R4, R6, X, Q, and W are described. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 35-36

(2010/11/26)

HEPATITIS C INHIBITOR PEPTIDE ANALOGS
The compounds of formula I wherein R1, R2, R3 , R4 and R5 are defined herein, are useful as inhibitors of the hepatitis C virus NS3 protease The invention further relates to azalactone compounds of the formula (II) which can be reacted with an amide anion to produce the HCV NS3 protease inhibitors of formula (I)
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Page/Page column 43-44

(2010/11/25)

Hepatitis C virus inhibitors
The present disclosure relates to tripeptide compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.
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Page/Page column 40; 41

(2008/06/13)

Hepatitis C virus inhibitors
The present disclosure is generally directed to antiviral compounds, and more specifically directed to compounds which inhibit the function of the NS3 protease (also referred to herein as “serine protease”) encoded by Hepatitis C virus (HCV), compositions comprising such compounds, and methods for inhibiting the function of the NS3 protease.
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Page/Page column 32-33; 44

(2008/06/13)

HEPATITIS C INHIBITOR DIPEPTIDE ANALOGS
The present invention relates to compounds of formula (I): wherein R1, R2, R4, n and m are as defined herein and R3 is selected from: (i) -C(O)OR31 wherein R31 is (C1-6)alkyl or aryl, wherein the (C1-6)alkyl is optionally substituted with one to three halogen substituents; (ii) -C(O)NR32R33, wherein R32 and R33 are each independently selected form H, (C1-6)alkyl, and Het; (iii) -SOvR34, wherein v is 1 or 2 and R34 is selected from: (C1-6)alkyl, aryl, Het, and NR32R33 wherein R32 and R33 are as defined above; and (iv) -CO(O)-R35, wherein R35 is selected from (C1-8)alkyl, (C3-7)cycloalkyl-(C1-4)alkyl, aryl, aryl-(C1-6)alkyl, Het and Het-(C1-6)alkyl, each of which are optionally substituted with one or more substituents each independently selected from halo, (C1-6)alkyl, (C3-7)cycloalkyl, aryl, Het, hydroxyl, -O-(C1-6)alkyl, -S-(C1-6)alkyl, -SO-(C1-6)alkyl, -SO2-(C1-6)alkyl, -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl, wherein the aryl portion of the -O-aryl, -S-aryl, -SO-aryl and -SO2-aryl are each optionally substituted with one to five halo substituents. The present invention further relates to pharmaceutical compositions containing the compounds of formula (I) and methods for using these analogs in the treatment of HCV infection.
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Page/Page column 81

(2008/06/13)

Hepatitis C inhibitor peptide analogs
Compounds of formula (I): wherein R1, R2, R3, R4, R5, Y, n and m are as defined herein. The compounds are useful as inhibitors of HCV NS3 protease.
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Page/Page column 36

(2010/02/15)

Synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid vinyl-ACCA derivatives: Key intermediates for the preparation of inhibitors of the hepatitis C virus NS3 protease
(1R,2S)-1-Amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is a key building block in the synthesis of potent inhibitors of the hepatitis C virus NS3 protease such as BILN 2061, which was recently shown to dramatically reduce viral load after administration to patients infected with HCV genotype 1. We have developed a scalable process that delivers derivatives of this unusual amino acid in >99% ee. The strategy was based on the dialkylation of a glycine Schiff base using trans-1,4-dibromo-2-butene as an electrophile to produce racemic vinyl-ACCA, which was subsequently resolved using a readily available, inexpensive esterase enzyme (Alcalase 2.4L). Factors that affect diastereoselection in the initial dialkylation steps were examined and the conditions optimized to deliver the desired diastereomer selectively. Product inhibition, which was encountered during the enzymatic resolution step, initially resulted in prolonged cycle times. Enrichment of racemic vinyl-ACCA through a chemical resolution via diastereomeric salt formation or the use of forcing conditions in the enzymatic reaction both led to improvements in throughput and the development of a viable process. The chemistry described herein was scaled up to produce multikilogram quantities of this building block.
Beaulieu, Pierre L.,Gillard, James,Bailey, Murray D.,Boucher, Colette,Duceppe, Jean-Simon,Simoneau, Bruno,Wang, Xiao-Jun,Zhang, Li,Grozinger, Karl,Houpis, Ioannis,Farina, Vittorio,Heimroth, Heidi,Krueger, Thomas,Schnaubelt, Juergen
p. 5869 - 5879
(2007/10/03)

HEPATITIS C VIRUS INHIBITORS
Hepatitis C virus inhibitors are disclosed having the general formula (I) wherein A, R2, R3, R', B and Y are described in the description. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 63-64; 66-67

(2010/02/11)

HEPATITIS C VIRUS INHIBITORS
Compounds are disclosed having general formula (I), wherein R1, R2, R3, R4, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.
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Page/Page column 63-65

(2010/02/11)

Substituted cycloalkyl P1' hepatitis C virus inhibitors
The present invention relates to tripeptide compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. In particular, the present invention provides novel tripeptide analogs, pharmaceutical compositions containing such analogs and methods for using these analogs in the treatment of HCV infection.
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Page/Page column 128; 129

(2010/02/06)

HEPATITIS C VIRUS INHIBITORS
Hepatitis C virus inhibitors are disclosed having the general formula:(I) wherein R1, R2, R3, R', B, Y and X are described in the description. Compositions comprising the compounds and methods for using the compounds toinhibit HCV are also disclosed.
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Page 74-75

(2008/06/13)

HETEROCYCLICSULFONAMIDE HEPATITIS C VIRUS INHIBITORS
The present invention relates to tripeptide compounds, compositionscontaining such compounds and methods for using such compounds for the treatment of heptitis C virus (HCV) infection. In particular, the present invention provides novel tripeptide analogs, pharmaceutical compositionscontaining such analogs and methods for using these analogs in the treatment of HCV infection.
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Page 75

(2010/02/05)

Diastereoselective Solid-Phase Synthesis of Novel Hydantoin- and Isoxazoline-Containing Heterocycles
Exploiting 1,3-dipolar cycloaddition and carbanilide cyclization transformations, we have prepared novel spirocyclic isoxazoloimidazolidinedione heterocycles of generalized structures II and III on solid phase starting from Merrifield resin. Cyclopentanoid isoxazoloimidazolidinedione II was obtained with complete diastereoselectivity, and cyclopropanoid isoxazoloimidazolidinedione III was obtained as an ≈ 2:1 mixture of diastereomers.
Park, Kyung-Ho,Olmstead, Marilyn M.,Kurth, Mark J.
p. 6579 - 6585
(2007/10/03)

Enantioselective synthesis of (1R,2S) and (1S,2S) dehydrocoronamic acids
Thanks to the successive use of two esterases with different regioselectivities and conventional organic chemistry we have synthesized (1R,2S) and (1S,2S) dehydrocoronamic acids.
Fliche,Braun,Le Goffic
p. 2873 - 2876
(2007/10/02)