LL 3858, SUDOTERB

New Drug Approvals

LL 3858, SUDOTERB

UNII-SK2537665A;

CAS 676266-31-2;

N-[2-methyl-5-phenyl-3-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]pyrrol-1-yl]pyridine-4-carboxamide;

N-[2-Methyl-5-phenyl-3-[[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]methyl]-1H-pyrrol-1-yl]-4-pyridinecarboxamide

Sudoterb(TM)

Molecular Formula:	C29H28F3N5O
Molecular Weight:	519.572 g/mol

• Originator Lupin
• Class Antituberculars; Isonicotinic acids; Pyrroles
• Mechanism of Action Undefined mechanism

• Orphan Drug Status No
• New Molecular Entity Yes

Highest Development Phases

• No development reported Tuberculosis

Most Recent Events

• 23 Jul 2015 No recent reports on development identified – Phase-II for Tuberculosis in India (unspecified route)
• 11 Dec 2013 Lupin completes a phase II trial in Tuberculosis in India prior to December 2013 (CTRI2009-091-000741)
• 31 Jul 2010 Lupin completes enrolment in its phase II trial for Tuberculosis in India (CTRI2009-091-000741)

Sudoterb HCl
CAS: 1044503-04-9 (2HCl)
Chemical Formula: C29H30Cl2F3N5O
Molecular Weight: 592.4882

SYNTHESIS

WO 2006109323

Tuberculosis (TB) is a contagious disease, which usually runs a protracted course, ending in death in majority of the cases, with relapse being a common feature of the disease. It is one…

View original post 4,241 more words

Advertisements

NNC 45-0781

New Drug Approvals

NNC 45-0781

Molecular Formula	C27H29NO3
Molecular Weight	415.5241

CAS 207277-66-5

• 2H-1-Benzopyran-7-ol, 3,4-dihydro-3-phenyl-4-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-, cis-(-)-
• (3S,4R)-3,4-Dihydro-3-phenyl-4-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-2H-1-benzopyran-7-ol

2H-1-Benzopyran-7-ol, 3,4-dihydro-3-phenyl-4-(4-(2-(1-pyrrolidinyl)ethoxy)phenyl)-, (3S,4R)-

• OriginatorNovo Nordisk
• ClassOsteoporosis therapies; Pyrrolidines; Small molecules
• Mechanism of ActionSelective estrogen receptor modulators

PATENT

WO 9818776

WO 9818771

WO 2003063859

A quantitative structure activity relationship study on cis-3,4-diaryl hydroxy chromones as high affinity partial agonists for the estrogen receptor
Chemistry: An Indian Journal (2003), 1, (3), 207-214

SYN 1

EP 0937057; WO 9818771, EP 0937060; WO 9818776

http://www.drugfuture.com/synth/syndata.aspx?ID=268276

Coumarin (III) was prepared by condensation of benzophenone (I) with phenylacetic acid (II) in the presence of Ac2O and Et3N. Reduction of the lactone function of (III) with LiAlH4, followed by acidic treatment furnished diaryl chromene (IV). Subsequent hydrogenation of (IV) over Pd/C gave rise to the racemic cis chromane (V), which was O-alkylated with 1-(2-chloroethyl) pyrrolidine (VI) producing the corresponding (pyrrolidinyl)ethoxy derivative. Resolution by means of active ditoluoyl tartaric acid yielded the desired (-)-enantiomer (VII). Finally…

View original post 482 more words

Ethyl(1R,2S,3S,4S)-2-(furan-2-yl)-3-nitro-6-oxobicyclo[2.2.2]octane-1-carboxylate

Ethyl(1R,2S,3S,4S)-2-(furan-2-yl)-3-nitro-6-oxobicyclo[2.2.2]octane-1-carboxylate

Compound 7 Ethyl(1R,2S,3S,4S)-2-(furan-2-yl)-3-nitro-6-oxobicyclo[2.2.2]octane-1-carboxylate To a solution of CAT 10 (128 mg, 0.37 mmol) and the nitroolefin 9 (3.1 g, 22.3 mmol) in 10 mL anhydrous CH2Cl2 at room temperature was added enone 8 (1.8 g, 10.7 mmol). The resulting mixture was stirred at the same temperature until enone 8 is consumed as indicated by TLC. Then DBU (0.34 mL, 3.20 mmol) was added and the mixture was allowed to stir at ambient temperature until completion as indicated by TLC. The solution was concentrated in vacuo and purified by flash chromatography on silica gel (Hexane / EtOAc = 20 / 1) to give 7 (2 g, 61% yield) as a yellow solid. [α]D 23 28.0 (c = 1.0, CHCl3).

1H NMR (400 MHz, CDCl3): δ 7.29 (d, J = 0.8 Hz, 1H), 6.27 (dd, J = 2.0 Hz, J = 3.2 Hz, 1H), 6.14 (d, J = 4.0 Hz, 1H), 4.93 (m, 1H), 4.57 (d, J = 4.4 Hz, 1H), 4.11 (m, 2H), 3.04-3.02 (m, 1H), 2.80-2.75 (m, 1H), 2.60- 2.54 (m, 1H), 2.33-2.29 (m, 1H), 1.88-1.72 (m, 2H), 1.33-1.23 (m, 1H), 1.21 (t, J = 7.2 Hz, 3H).

13C NMR (100 MHz, CDCl3): δ 204.1, 168.7, 151.8, 142.5, 110.5, 108.1, 88.3, 61.3, 56.3, 42.0, 40.8, 33.7, 26.9, 19.2, 13.8.

IR (thin film): 3435, 3141, 3120, 2996, 2959, 1715, 1653, 1621, 1557, 1505, 1473, 1443, 1408, 1371, 1336, 1301, 1336, 1301, 1270, 1236, 1142, 1120, 1083, 1062, 1074, 1045, 1045, 1011, 996, 960, 930, 892, 884, 867, 803, 753, 628, 600, 508, 436 cm-1 .

LRMS (ESI): 308.0 (M+H)+ , 330.0 (M+Na)+ .

HRMS (ESI): calcd for C15H18O6N (M+H) + : 308.1129. Found: 308.1130.

Melting point: 117-118 oC.

Concise asymmetric total synthesis of (−)-patchouli alcohol

Guang-Qiang Xu,a  Guo-Qiang Lina  and  Bing-Feng Sun*a 

 Author affiliations

*Corresponding authors

aCAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, 345 Lingling Road, Shanghai 200032, China
E-mail: bfsun@sioc.ac.cn

Abstract

The asymmetric total synthesis of (−)-patchouli alcohol was accomplished in a concise manner. Key reactions include a highly diastereo- and enantioselective formal organocatalytic [4 + 2] cycloaddition reaction, a radical denitration reaction, and an oxidative carboxylation reaction. The formal synthesis of norpatchoulenol was achieved as well.

• This article is part of the themed collection: Synthetic Approaches to Natural Products via Catalytic Processes

/////////

“ORG CHEM SELECT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

Synthesis of isosorbide: an overview of challenging reactions

New Drug Approvals

Synthesis of isosorbide: an overview of challenging reactions

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC01912B, Tutorial Review

C. Dussenne, T. Delaunay, V. Wiatz, H. Wyart, I. Suisse, M. Sauthier
This review gives an overview of the catalysts and technologies developed for the synthesis of isosorbide, a platform molecule derived from biomass (sorbitol and cellulose).

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC01912B?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

C. Dussenne,^a  T. Delaunay,^b  V. Wiatz,^c  H. Wyart,^c  I. Suisse^a  and  M. Sauthier*^a 

 Author affiliations

*Corresponding authors

^aUMR 8181 Unité de Catalyse et de Chimie du Solide, Université Lille Nord de France, USTL, ENSCL, Cité Scientifique, 59652 Villeneuve d’Ascq Cedex, France

^bInstitut Français des Matériaux Agro-Sourcés, Parc Scientifique de la Haute Borne, 60 Avenue du Halley, 59650 Villeneuve d’Ascq, France

^cRoquette Frères, 62080 Lestrem Cedex…

View original post 1,243 more words

ELAMIPRETIDE

New Drug Approvals

H-D-Arg-Tyr(2,6-diMe)-Lys-Phe-NH2

D-arginyl-2,6-dimethyl-L-tyrosyl-L-lysyl-L-phenylalaninamide

(2S)-6-amino-2-[[(2S)-2-[[(2R)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]amino]-N-[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]hexanamide

CAS 736992-21-5

Chemical Formula: C32H49N9O5

Molecular Weight: 639.8

• A free radical scavenger and antioxidant that localizes in the inner mitochondrial membrane.
• Mitochondrial Protective Agent to Improve Cell Viability

1. Elamipretide
2. bendavia
3. UNII-87GWG91S09
4. 736992-21-5
5. MTP 131
6. RX 31
7. SS 31
8. 87GWG91S09
9. L-Phenylalaninamide, D-arginyl-2,6-dimethyl-L-tyrosyl-L-lysyl-
10. SS-31 peptide
11. Arg-Dmt-Lys-Phe-NH2
12. D-Arg-Dmt-Lys-Phe-NH2
13. SS31 peptide
14. Elamipretide [USAN:INN]
15. MTP-131
16. Elamipretide (USAN/INN)
17. arginyl-2,’6′-dimethyltyrosyl-lysyl-phenylalaninamide
18. CHEMBL3833370
19. SCHEMBL15028020
20. CTK2H1007

Elamipretide (also known as SS-31 and Bendavia)^[1][2] is a small mitochondrially-targeted tetrapeptide (D-Arg-dimethylTyr-Lys-Phe-NH2) that appears to reduce the production of toxic reactive oxygen species and stabilize cardiolipin.^[3]

Stealth Peptides, a privately held company, was founded in 2006 to develop intellectual property licensed from several universities including elamipretide; it subsequently changed its name to Stealth BioTherapeutics.^[4][5]Acute coronary syndrome; Age related macular degeneration; Cardiac failure; Corneal dystrophy; Diabetic macular edema; Lebers hereditary optic atrophy

• Originator Stealth Peptides
• Developer Stealth BioTherapeutics
• Class Eye disorder therapies; Ischaemic…

View original post 3,340 more words

Total CCl4 guest alignment in a quasiracemic clathrate closely related to Dianin’s compound

Total CCl4 guest alignment in a quasiracemic clathrate closely related to Dianin’s compound

CrystEngComm, 2017, 19,5703-5706
DOI: 10.1039/C7CE01275F, Communication

Christopher S. Frampton, James H. Gall, David D. MacNicol
In the trigonal CCl₄quasiracemic clathrate, space group R3, formed from host components S-(-)-Dianin’s compound, 4, and its (+)-2R,4R 2-nor methyl analogue, 2, the unprecedented complete ordering of a C-Cl bond of the guest with respect to the c-axial direction and the participation of an unexpected host conformation is reported for the first time.

http://pubs.rsc.org/en/Content/ArticleLanding/2017/CE/C7CE01275F?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FCE+%28RSC+-+CrystEngComm+latest+articles%29#!divAbstract

Christopher S. Frampton,*^a  James H. Gall^b  and  David D. MacNicol*^b 

 Author affiliations

*Corresponding authors

^aWolfson Centre for Materials Processing, Brunel University, Kingston Lane, Uxbridge, UK
E-mail: chris.frampton@brunel.ac.uk
Fax: +44 (0)1895 203376
Tel: +44 (0)1895 265337

^bDepartment of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK
E-mail: david.macnicol@glasgow.ac.uk
Tel: +44 (0)141 330 4479

Abstract

Single crystal X-ray analysis at 100 K reveals that in the trigonal CCl₄quasiracemic clathrate, space group R3, formed from host components S-(−)-Dianin’s compound and its (+)-2R,4R 2-nor methyl analogue there is an unprecedented complete ordering of a C–Cl bond of the guest with respect to the c-axial direction. In this clathrate and that formed from the (+)-2R,4R and (+)-2R,4S epimers the participation of an unexpected host conformation is reported for the first time.

////////////

2,5-Bis(ethoxymethyl)furan

2,5-Bis(ethoxymethyl)furan, 6

1H NMR (CDCl3) = 6.20 (s, 2H), 4.36 (s, 4H), 3.47 (q, 4H, J = 7.1 Hz), 1.16 (t, 6H, J = 7.1 Hz);

13C NMR (CDCl3) = 150.9, 109.7, 65.7, 64.7, 15.1 ppm

PREDICTS

Efficient route for the construction of polycyclic systems from bioderived HMF

Green Chem., 2017, Advance Article

DOI: 10.1039/C7GC02211E, Paper

F. A. Kucherov, K. I. Galkin, E. G. Gordeev, V. P. Ananikov

Efficient one-pot synthesis of tricyclic compounds from biobased 5-hydroxymethylfurfural (HMF) is described using a [4 + 2] cycloaddition reaction.

Efficient route for the construction of polycyclic systems from bioderived HMF

F. A. Kucherov,^a  K. I. Galkin,^a  E. G. Gordeev^a  and  V. P. Ananikov*^a 

 Author affiliations

*Corresponding authors

^aZelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, Moscow 119991, Russia

E-mail: val@ioc.ac.ru

Web: http://AnanikovLab.ru

//////////