Download - Granlen-The Reliability 201605
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A Reliable and Innovative Partner to Speed up Your Success
The Reliable Leading Nucleoside Pioneer!
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Outline
Overview ∙ Experience ∙ Services ∙ Granlen
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Corporate Locations
美国加州圣地亚哥–太平洋彼岸的“人间天堂”,最适于居住的城市San Diego, CA
- The Paradise on Earth;the
most livable city
中国郑州 - 重要交通枢纽,商贸中心,国家园林城市Zhengzhou, China
- The key transportation and
business central garden city
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About Granlen
• Provides reliable chemistry related services for the biotech, pharmaceutical, diagnostic, cosmeceutical, and related industries with:
– A broad spectrum of chemistry
– A wide range of drug discovery services
– An integrated drug development process to IND
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The Granlen Difference
Satisfy your needs Speed your success
Committed to Total Quality Excellence
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Granlen’s Strengths
Synthetic Organic Chemistry
Medicinal Chemistry
Combinatorial Technologies
Drug discovery and development to IND
Immunogens and bioreagents
6
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Synthetic Organic Chemistry
Heterocyclic and macrocyclic derivatives
Natural products and derivatives
Peptides, carbohydrates, glycopeptides
Process development and large scale synthesis – mg to multi-kg scale
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Medicinal Chemistry
Hit-to-lead
Lead Optimization– Natural products
– SAR studies
– Liability removal
– Automation for expansion
Integrated preclinical discovery services
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Medicinal Chemistry
Target Expertise
KinasesMicrotubulesPolymerases
ProteasomeReverse TranscriptaseRNA
GPCRsOther key enzymes
Therapeutic Experience
Oncology
Infectious AntiviralAntibacterialAnti-TB
Metabolic disordersObesityDyslipidemiaDiabetes
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Our History of Success
OncologyMicrotubule polymerization inhibitor (Phase II)
Kinase inhibitor (Phase II)
Proteasome Inhibitor (Preclinical)
Medicinal Chemistry and Drug Development
AntiviralAn HBV drug (Phase III)
An HIV drug (Phase II)
An HCV drug (Phase II)
An HIV drug (Phase I)
An HCV candidate (IND)
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CombiChem and Automation for Medicinal Chemistry
Solution-phase chemistry - parallel or indexedSolid-phase methodologies
• Method development
• Focused libraries and parallel synthesis
• Supporting material modification
• Solid-phase extraction technology
• Library enumeration and tracking
Expertise in nucleoside libraries andfocused heterocyclic libraries
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Carbohydrate Derivatives
S
OO
HO
S
OBzBzO
BzO
OAc
S
OHOH
HOO
OO
HO
OO
OOHO
O
O
OBnBnO
BnO
O
O
OAcF
p-TolOOAc O
OAcN3
p-TolOOAc
O
OHBzO
BzOOBz
O
OAc
BzO OAcO
OAcO
BzO OAcO
OAcBzO
BzO OAc
H3C
O
OAc
F
BzO OAc
H3C
O
OAcCH3
BzO OAc
O
OBzBzO
BzOOAc
CH3
O
OAcCl2BnO
Cl2BnOOAc
O
O
OBnO
BnO
IO
O
OBnO
BnO
HO
O
OAc
HO
BzO OAc
O
OAcp-TolO
OAc
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Representative Pyrimidine Nucleosides
NO
OHH, F, N3, NH2, CH3,
MeO
HO
N
OH, NH2
O
R
O
H, F, N3, NH2, CH3
HO N
OH
O
OH
OF, N3, NH2,
HO
HO N
N
OH, NH2
O
O
H, F, N3, NH2, CH3
HO
OH
N
N
O
O
H, F, N3, NH2, CH3
HO
OH
N O
O2N
O
H, F, N3, NH2, CH3,
MeO,
HO
OH
N
N
O
NH2
R
H, OH
N
OH, NH2
ONO
OHHO
HO
N3, CH3, CN
R
NO
OHHO
HO
N
OH, NH2
O
R
CH3
NO
OH, N3, NH2, F, Cl, OMe
HO
HO
N
OH, NH2
O
R
O
HO
HO N
N
O
F
H, OH, NH2
R
O
F,HO
HO N
NH
O
S
OR
R
NS
OHHO
HO
N
OH, NH2
O
R
O
H, OH, OMe, F
OH
N
N
O
O
R
O
HO,F,N3
HO
H,OH,OR,F, N3
N
NH
S
O
R
NO
HO
N
OH, NH2
O
R
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Representative Purine Nucleosides
N
N
N
H, OH, NH2, Cl, OMe, NHR, R
NO
OH, N3, NH2, OMe, OR, CH2CH2OMe, O-ethynyl
HO
HO
O
HO
HO
F, H
N
Y
N
N
H, NH2, Cl, OH, OMe
H, NH2, Cl, OH, OMe
NH
N
N
O
NO
OH, ORHO
HOH, NH2, I, SH, SR, CH3, NHR
R
N
NN
N+
O
HO
HO
NH2
NH, NHR
OH
R
N
OHO
R
N
NN
N
OH, NH2
H, NH2
H, NH2
H, OH
N
N
N
H, OH, NH2, Cl, OMe, NHR, R, Ar, Het
NO
OHH, F, N3, NH2, CH3, MeO
HO H, NH2
NH
NN
N
S
O
OH, HH, F, N3, CH3
HOH, NH2
O
H, F, N3, NH2, CH3, MeO,
HO
OH
N
N
NH
N
NH2
O
H, FOF, N3,
NH2, HO
HO
H, OH
N
N
N
H, OH, NH2, Cl
N H, NH2
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3’-Fluoro-3’-deoxy Pyrimidine/Pyridinone Nucleosides
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3’-Fluoro-3’-deoxy Purine Nucleosides
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2’-Fluoro-2’-deoxy Pyrimidine Arabinonucleosides
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2’-Fluoro-2’-deoxy Purine Arabinonucleosides
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Azido-Nucleosides
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Amino-Nucleosides
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Isocytidines and Isoguanosines
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Thio-Nucleosides
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Xylofuranose-nucleosides
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2’,3’-Dideoxy Substituted Nucleosides
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2’,3’-Dideoxy / didehydro-Nucleosides
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3’-Methyl-3’-deoxy and 3’-Deoxy Nucleosides
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Pyrimidinone and Pyridinone Nucleosides
(3-Deaza-/4-deoxy Us)
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6-Deamino and 6-Methylpurine Nucleosides
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2-Subsituted Purine Nucleosides
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5’-Modified Nucleosides
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Nucleosides Having One Reactive Group on Sugar
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Morpholino-Nucleosides
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PNA Monomers
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Drugs and Inhibitors
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Nucleotides, Amidites and Phosphonates
O
O
NH2
O
O-
N
NN
NO
NH2
OO
O
P-O O
N
N
O
P O-O
NH
R
NVOCO
H
R'
ON
OHR
N
NH2
O
HOOH
ON
N
N
NH
O
O
OMeO
P O
P O-S
O
NH2
R = H, OMe
dinucleotides
N
OH, NH2
ONO
ROH
PHO O
OH
PO
N
NC
NH
O
ONO
RO
PRO O
OR RR
O
R
N
N
Z
NH
O
RPO
PO
P-O -O
OO
-O
O
O-
X
XR
phosphonamiditeH-phosphonate
N
NN
N
O
O
DMTrO
NHBz
OPO
N
NC
NH
NN
N
O
O
DMTrO
O
NHBui
OP
O
N
NC OCH3
N R
N
N
N
NH2
O
R OR
P O
RO
HO
XX
triphosphonatesphosphonates
phosphoramidites
phosphonate amidites
PO
O-
N
N
ONO
R
ODMTr
H3C
H
PO
N
NC
NH
O
ONO
R
ODMTr
H3CNCH3
+HNEt3
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Representative Nucleoside Phosphoramidites
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Nucleoside Phosphoramidites
NH
NN
N
O
O
O
O
NH
O
O
DMTr
PO
N
NC
NH
NN
N
O
O
O
O
NH
O
O
DMTr
PO
N
NC OCH3
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Nucleoside Triphosphates (NTPs)
LC (TIC)
LC (UV)
1) P(O)(OMe)3 proton sponge 2) POCl3 3) Pyrophosphate
1) ion exchange column2) reverse phase column
3) LyopholizationN
O
OCH3OH
OP
O
O
O-
P
O
O-
OP
O
O-
-O
NH
O
O
n Et3NH+
NO
OCH3OH
HO
NH
O
O
H3C H3C
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39
Other Products with Different Applications
N
SN
N+N
Cl-
HO OH
Dipropofol/ drug standard
Catalyst
HON
OH
OH
OH
OH CH3
O
Mega 8 /Bio-reagent
N NCOOR
N
ROOC
COOR
COORROOC
H2N
MRI Contrasting Agents
DDAIP-HCl (Formulation)
O
NH+
O
Cl-
Phenothiazine
O
O
O
O
R
R
R
R
RuN+
N+
X
X
OH
O
O
O-
Complex /bio-reagent
SO3H
SO3H
N
N N
N
O
OHOH
ONH
NC
ClCl
NH2
HSP30 inhibitorFlavor Additive
O O
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Purine Derivatives
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Pyrimidines, Pyrazines and Pyradazines
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Other Building Blocks
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Natural Products and Derivatives
N N
H2N
CH3
O
OCH3
O
HN
O
HO
HN
HN
CH3
N
H2N
NH
NH2
OO
NH
HO
S
O
O
S
NNH
O
R2
O
OHO
HO
HO
OH R1
OH
OH
NH
N
H
H
H
HH
H
NH2
H
HCH3
R1 = OCONH2, OH; R2 = SMe, +SMe2
7 Bleomycins including: Bleomycin A2, Bleomycin
demethyl A2, and Decarbamoyl Bleomycin Demethyl A2
>48 steps each for the total synthesis
Bleomycin Antitumor Antibiotics
R3
H
O
X
OR
H
OR
H
O
OR
Oridonin
5'-Alkylresorcinols isolated from Hakea trifurcatea DNA cleaving agents
l m n
HO
OH
OH
OH
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Our Specialties
Carbohydrates, nucleosides/tides, & libraries
Phosphoramidites, phosphates, triphosphates,
C-phosphonates
Natural product total synthesis
Heterocycles, macrocycles, super-chelating and MRI contrast agents
Immunogens/antigens and bio-reagents
Prodrug and conjugation technologies
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Chemistry Services
Hit to lead & lead optimization
Screening & focused libraries
Custom Synthesis
Chemistry &Drug Discovery
PreclinicalDevelopment
ClinicalDevelopment
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Hit and Lead Optimization
Hit re-synthesis for activity confirmation
Lead selection and optimization for SAR studies
Design & synthesis of analogs for lead improvement
Optimize potency, selectivity, specificity, and safety
Improve PK, PD, and druggability
Enhancement of IP coverage
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Screening and Focused Libraries
Screening library enhancement
Drug-like or Lead-like (Ro5)
Toxicophore filtration
Focused libraries around specified targets
Structure/Ligand-based design
Optimization by virtual screening
10-50 mg per sample with >90% purity
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Custom Synthesis
Products, intermediates, scaffolds, building
blocks, monomers, raw materials
Reference and competitor compounds
Drug standards, metabolites and impurities
Immunogens/antigens, bio-reagents
Radiolabeling method development
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IND-Enabling Preclinical Services
Process development research & LSS
Analytical method development and stability studies
Regulatory and documentation
Chemistry &Drug Discovery
PreclinicalDevelopment
ClinicalDevelopment
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Process Development & LSS
Route scouting to Route finalization
Reaction condition / process optimization
Efficient processes for multi-kilo scales
Scalable and transferable
processes
Kilo to ton scale manufacture
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Analytical Services
Develop and validate analytical methods
Establish drug criteria for drug substances and pharmaceutical products
Drug stability studies:
– Freeze-thaw
– Forced degradation
– Accelerated and long-term stability
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Intellectual Property ProtectionIntellectual Property Protection
Highest Priority
Isolated facility to ensure IP protection
Strict documentation procedures
Professional management team focused on IP protection
Intellectual property belongs to the client
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Our ClientsGlobal clients in US, Canada, Singapore, Japan, India,
Europe, and China
Custom synthesis, drug discovery, analytical method,
process development, LS synthesis, pre-clinic CMC etc
Services include Focused libraries, hit design and synthesis, lead optimization for SAR
Synthesis of nucleosides, phosphoramidites, triphosphates, heterocyclic and macrocyclic derivatives, drug standards, metabolites, impurities, etc
Conjugation, asymmetric compounds, formulation products, organic materials, dyes, bio-reagents, etc
Pre-clinical development, methods and pharmaceutical
53
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Example 1 - Drug Discovery Project
Participated in the project plan from very early stage
Designed potential hit/lead structures to be selected
Designed routes and worked out synthesis
Bi-weekly report and adjust direction as needed
Submitted high quality samples for biological tests
and write-up document
Secure confidentiality and client owns the IP
Luckily, a great lead was discovered
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Example 2 – IND Enabling Drug Development
Require: pre-clinical CMC and pharmaceutical for IND
Explored possible routes and finalized the best one
Fine-tuned reaction conditions and processes (batches)
Allow cost reduction of 80% for production
3 kg high quality product met drug requirements and used for clinical studies
Developed anal method, established drug criteria, QC
Provided all documents to support IND application
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Example 3 –New Phosphonate Amidite
Required: 20 g of new phosphonate phosphoramidite
Designed reasonable and doable route
Worked out the key steps and accomplished smoothly
Delivered high-quality product and write-up document
with all data in ~60% expected time frame
“Harry, That’s great and fast! I had a failed delivery
before on the same compound”, the client said after
the project was completed
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Example 4 – Halo-Nucleoside
Required: 50 g scale synthesis (for big pharma; failed
by other vendors before)
Designed the un-reported new route, and it was
agreed by client
Explored and synthesized halo-sugar
Synthesized and delivered final product in high
quality and timely fashion
We are the only group who can make this type of
nucleosides in sizable scale (a Large CRO failed on the
same compound)
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Here is what one of our clients said:
Haoyun,
Very impressive! No one can beat you on this area. Please send me the invoice for this PO.
Best Regards,John
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Operation & Facilities
Headquartered in San Diego, CA (Sign CDA in US)
Operation in Zhengzhou, China
The transportation and business central garden city
Hydrogenator, high-pressure reactors, shakers, large
evaporator, and 100 L reactors for large scale synthesis
Anal/semi-preparative HPLCs, medium pressure LC,
lyophilizer, LC-MS, NMR, HRMS, FT-IR, UV-Vis, DSC/TG,
X-ray, polarimeter, stability test chambers, etc
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60
The quality of our equipment is nothing
when compared to the quality of our people!
Corners of Granlen
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One View in Zhengzhou
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Summary
Highly experienced management
Unique specialties and highly skilled teams
Quality > Reliability > Costs
No challenge to great or small (Serve/Help)
Timely communication for high efficiency
Continuously improving infrastructure
We deliver regardless what it takes
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We Work Harder!
Skype: haoyun.an
QQ: 1015260133
1-760-846-6460 (US)
011-86-158-38132863 (China)
011-86-371-86026726 (China)
The Reliable Leading Nucleoside Pioneer!