Chirality.

Presentation on theme: "Chirality."— Presentation transcript:

1 Chirality

2 C3, C4 and C6 Chiral Building Blocks Samsung Fine Chemicals Co., Ltd.
contact us!!

3 Pharmaceutical Fine Chemical 시장 분석 (1999년, 출처: ADL)

4 세계의약품 및 카이랄 중간체 시장 현황 세계 완제의약 시장 ( $ billion ) 완제의약 시장분포 ( %, 판매액 기준 )

5 의약관련 정밀화학분야 환경 FDA 정책변화 (1992년)
"Chiral 의약품은 Racemic과 Enantiomer를 다른 물질로 간주한다" 예 > (R,S)-Ibuprofen →(S)-Ibuprofen(1996년) 입체이성질체가 있는 경우 하나의 이성체만 의약품으로 인정 정밀화학제품의 60% →의약관련제품 원료의약품의 70%→Chiral 의약품 정밀화학제품중 Chiral 의약품의 비중 42% 지속적인 Chirotechnology 확보가 필수조건

6 Chirotechnology의 분류(의약품분야)
방법 Chiral Pool Asymmetric Synthesis Bio Catalyst 원료 천연물 Chiral Ligand, 귀금속촉매 또는 광학분할제 효소 광학활성 도입방법 출발물질의 광학활성위치 활용 합성방법으로 광학활성위치도입 효소의 위치선택적 반응성 이용 도입 광학순도 매우 우수 (> 99 % ee) 우수 (95-99%ee) 매우 우수 (>99%ee) 개발측면 기술확보 용이 장시간 개발기간소요 장시간 개발기간소요 장치면 단순 촉매/Ligand/분할제 회수공정(고난도) 장치산업 파급효과 기술중심품목군 Down Stream 형성 가능 품목군형성가능 촉매별 공정개발要 1효소 1품목 적용

7 The Chirality Pool Carbohydrates
D-Sucrose, D-Lactose, L-Ascrobic acid, etc Hydroxy acids L-Lactic acid, L-tartaric acid, L-Malic acid Amino acids L-Glutamic acid, L-Phenylalanine, L-Prolin Terpenes (+)-Camphor, (+)-Limonene, (-)-Menthol Alkaloides Ephedrine, Quinine, Cinchonidine

8 Preparation of HGB General Scheme

9 C4-Chiral Intermediate

10 Lactose and oligosaccharide methods
Patent No. US

11 Mechanism of base catalyzed, oxidative degradation of an amylose chain

12 Preparation of Ethyl (R)-4-Cyano-3-hydroxybutanoate
Route 1 Route 2

13 Patented Manufacturing Process of CHB by SFC

14 (S)-C3 chiral building blocks
(S)-N-(2,2-Dimethyl-1[1,3]dioxolan-4-ylmethyl)-acetamide(S-ADD) (S)-N-(3-Bromo-2-hydroxy-propyl)-acetamide(S-BHA) (S)-N-Oxiranylmethyl-acetamide (S-OMA) (S)-3-amino-1,2-propandiol (S-APD) Applications: 1. Chiral building block for the syntheis of Zyvox®; WO (Pharmacia & Upjohn) 2. Key intermediates for various drugs in Clinical trials

15 Preparation of Oxazolidinone

16 acetic acid t-butyl ester
(3R,5R)-(6-Cyanomethyl-2,2-dimethyl-[1,3]dioxan-4-yl)- acetic acid t-butyl ester CDH Application: Key intermediate for the synthesis of Lipitor®; WO , EP (Pfizer)

17 acetic acid t-butyl ester
(3S,5R)(6-Hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)- acetic acid t-butyl ester HDH  Application: Key intermediate for the synthesis of Crestor®

18 Key Intermediate : (R)-& (S)-Epoxide

19 C3-C4, C6 Chiral building blocks

20 HGB and Triol derivatives
Product lineup HGB and Triol derivatives

21 BHBA derivatives

22 LCT derivatives

23 C3 derivatives

24 RHA derivatives

25 Applications

26

27 Technology Radical reaction Chlorination Reduction
Carbohydrates based Chiral Pool High pressure reaction(100bar) Low temperature reaction(-90oC) Classical Resolution Enzyme reaction Dynamic Kinetic Resolution* * Under development

28 World Best 배타적 영업확보 MY PRODUCT MY MY PROCESS TECHNOLOGY 기술의 고유영역확보
독자적인 신기술