KR910009635A - 글루타르산 유도체 및 이의 제조방법 - Google Patents
글루타르산 유도체 및 이의 제조방법 Download PDFInfo
- Publication number
- KR910009635A KR910009635A KR1019900018469A KR900018469A KR910009635A KR 910009635 A KR910009635 A KR 910009635A KR 1019900018469 A KR1019900018469 A KR 1019900018469A KR 900018469 A KR900018469 A KR 900018469A KR 910009635 A KR910009635 A KR 910009635A
- Authority
- KR
- South Korea
- Prior art keywords
- salt
- compound
- formula
- alkyl
- product
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 7
- 150000002310 glutaric acid derivatives Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/30—Preparation of optical isomers
-
- 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
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Description
Claims (14)
- 사실상 광학적으로 순수한 2(S)-입체 이성체 형태인 일반식(Ⅰ)의 화합물 또는 이의 염.상기식에서, R은 C1내지 C4알킬 또는 -CH2CH2Si(CH3)3이고, ★은 (S) 입체화학을 갖는 비대칭 중심이다.
- 사실상 광학적으로 순수한 2(S)-입체 이성체 형태인 일반식(Ⅱ)의 화합물 또는 이의 염.상기식에서, R 및 ★은 제1항에서 정의한 바와 같다.
- 일반식(Ⅲ)의 화합물을 -10℃ 또는 -10℃ 이하의 온도에서 비극성 유기용매 속에서 일반식(Ⅳ)의 화합물의 염과 반응시킨 다음, -10℃ 또는 -10℃ 이하의 온도에서 반응 화합물을 산성화시키고, 임의로 생성물을 이의 염으로 전환시킴을 포함함을 특징으로 하여, 사실상 광학적으로 순수한 2(S)-입체이성체 형태인 일반식(Ⅰ)의 화합물 또는 이의 염을 제조하는 방법.상기식에서, R은 C1내지 C4알킬 또는 -CH2CH2Si(CH3)3이고, ★은 (S)-입체화학을 갖는 비대칭 중심이고, M1및 M2은 동일하거나 상이할 수 있고,및로부터 선택된다.
- (a)일반식(Ⅲ)의 화합물을 -10℃ 또는 -10℃ 이하의 온도에서 비극성 유기용매 속에서 일반식(Ⅳ)의 화합물의 염과 반응시키고, 임의로 생성물을 이의 염으로 전환시켜 사실상 광학적으로 순수한 2(S)-입체이성체 형태인 일반식(Ⅰ)의 화합물 또는 이의 염을 수득한 다음, (b)(a)의 생성물을 촉매 수소화 반응시키고, 임의로 (b)의 생성물을 이의 염으로 전환시켜 사실상 광학적으로 순수한 2(S)-입체이성체 형태인 일반식(Ⅱ)의 화합물 또는 이의 염을 수득함을 포함함을 특징으로 하여, 일반식(Ⅱ)의 화합물 또는 이의 염을 제조하는 방법.상기식에서, R은 C1내지 C4알킬 또는 -CH2CH2Si(CH3)3이고, ★은 (S)-입체화학을 갖는 비대칭 중심이고, M1및 M2은 동일하거나 상이할 수 있고,및로부터 선택된다.
- 제4항에 있어서, 사실상 광학적으로 순수한 2(S)-입체이성체 형태인 일반식(Ⅰ)의 화합물 또는 이의 염을 촉매 수소화 반응시키고, 임의로 생성물을 이의 염으로 전환시킴을 특징으로 하여, 사실상 광학적으로 순수한 2(S)-입체이성체 형태인 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제3항 또는 제4항에 있어서, M1과 M2가 모두인 방법.
- 제6항에 있어서, 일반식(Ⅳ)의 화합물의 염은 리튬 디이소프로필아미드를 사용하여 사이클로펜탄카복실산을 양성자제거반응시킴으로써 수득하고, 비극성 유기용매가 테트라하이드로푸란인 방법.
- 제4항 또는 제5항에 있어서, 촉매 수소화 반응이 일반식(Ⅰ)의 화합물의 염기성을 사용하여 수행되는 방법.
- 제4항, 제5항 또는 제8항에 있어서, 촉매 수소화 반응이 촉매로서 목탄상의 수산화팔라듐을 사용하여 수행되는 방법.
- 제3항 또는 제4항에서 정의한 바와 같이 일반식(Ⅲ)의 화합물.
- 제1항, 제2항 또는 제10항에 있어서, R이 C1내지 C4알킬인 화합물.
- 제3항 내지 제9항 중의 어느 한 항에 있어서, R이 C1내지 C4알킬인 화합물.
- 제1항, 제2항 또는 제10항에 있어서, 일반식(Ⅰ) 또는 (Ⅱ)의 화합물의 염이 산부가염 또는 바람직하게는 염기염인 화합물.
- 제3항 내지 제9항 중의 어느 한 항 또는 제11항에 있어서, 일반식(Ⅰ) 또는 (Ⅱ)의 화합물의 염이 산부가염 또는 바람직하게는 염기염인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898925933A GB8925933D0 (en) | 1989-11-16 | 1989-11-16 | Glutaric acid derivatives and preparation thereof |
GB89259337 | 1989-11-16 | ||
GB8925933.7 | 1989-11-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR910009635A true KR910009635A (ko) | 1991-06-28 |
KR940005958B1 KR940005958B1 (ko) | 1994-06-25 |
Family
ID=10666416
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019900018469A KR940005958B1 (ko) | 1989-11-16 | 1990-11-15 | 글루타르산 유도체 및 이의 제조방법 |
Country Status (29)
Country | Link |
---|---|
US (1) | US5087732A (ko) |
EP (1) | EP0432898B1 (ko) |
JP (1) | JPH03176460A (ko) |
KR (1) | KR940005958B1 (ko) |
CN (2) | CN1028361C (ko) |
AT (1) | ATE104270T1 (ko) |
AU (1) | AU623814B2 (ko) |
BR (1) | BR9005746A (ko) |
CA (1) | CA2029785C (ko) |
CZ (1) | CZ284374B6 (ko) |
DE (1) | DE69008130T2 (ko) |
DK (1) | DK0432898T3 (ko) |
EG (1) | EG19319A (ko) |
ES (1) | ES2062410T3 (ko) |
FI (1) | FI107148B (ko) |
GB (1) | GB8925933D0 (ko) |
HU (1) | HU207711B (ko) |
IE (1) | IE63684B1 (ko) |
IL (1) | IL96299A (ko) |
MX (1) | MX23335A (ko) |
MY (1) | MY104782A (ko) |
NO (1) | NO179072C (ko) |
NZ (1) | NZ236080A (ko) |
PH (1) | PH27369A (ko) |
PL (2) | PL164543B1 (ko) |
PT (1) | PT95889B (ko) |
RU (1) | RU2002734C1 (ko) |
SK (1) | SK568590A3 (ko) |
ZA (1) | ZA909161B (ko) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5208236A (en) * | 1992-09-23 | 1993-05-04 | Schering Corporation | N-(acylaminomethyl)glutaryl amino acids and use |
FR2890069B1 (fr) * | 2005-08-31 | 2011-03-04 | Senn Chemicals Internat | Intermediaires de synthese pour la preparation de b2-aminoacides et leurs procedes de preparation |
ES2400484T3 (es) * | 2010-04-15 | 2013-04-10 | Indena S.P.A. | Un proceso para la preparación de derivados de isoserina |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2460891C2 (de) * | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
KR880007441A (ko) * | 1986-12-11 | 1988-08-27 | 알렌 제이.스피겔 | 스피로-치환된 글루타르아미드 이뇨제 |
GB8820844D0 (en) * | 1988-09-05 | 1988-10-05 | Pfizer Ltd | Therapeutic agents |
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1989
- 1989-11-16 GB GB898925933A patent/GB8925933D0/en active Pending
-
1990
- 1990-10-26 US US07/604,845 patent/US5087732A/en not_active Expired - Fee Related
- 1990-11-09 IL IL96299A patent/IL96299A/xx active IP Right Grant
- 1990-11-12 EG EG67590A patent/EG19319A/xx active
- 1990-11-13 CA CA002029785A patent/CA2029785C/en not_active Expired - Fee Related
- 1990-11-13 BR BR909005746A patent/BR9005746A/pt not_active Application Discontinuation
- 1990-11-13 DE DE69008130T patent/DE69008130T2/de not_active Expired - Fee Related
- 1990-11-13 ES ES90312347T patent/ES2062410T3/es not_active Expired - Lifetime
- 1990-11-13 EP EP90312347A patent/EP0432898B1/en not_active Expired - Lifetime
- 1990-11-13 AT AT90312347T patent/ATE104270T1/de not_active IP Right Cessation
- 1990-11-13 DK DK90312347.9T patent/DK0432898T3/da active
- 1990-11-14 NZ NZ236080A patent/NZ236080A/en unknown
- 1990-11-14 PL PL90287759A patent/PL164543B1/pl unknown
- 1990-11-14 PT PT95889A patent/PT95889B/pt not_active IP Right Cessation
- 1990-11-14 PL PL90299211A patent/PL164610B1/pl unknown
- 1990-11-14 MX MX2333590A patent/MX23335A/es unknown
- 1990-11-15 NO NO904961A patent/NO179072C/no not_active IP Right Cessation
- 1990-11-15 RU SU904831690A patent/RU2002734C1/ru active
- 1990-11-15 ZA ZA909161A patent/ZA909161B/xx unknown
- 1990-11-15 IE IE412190A patent/IE63684B1/en not_active IP Right Cessation
- 1990-11-15 FI FI905664A patent/FI107148B/fi not_active IP Right Cessation
- 1990-11-15 AU AU66684/90A patent/AU623814B2/en not_active Ceased
- 1990-11-15 KR KR1019900018469A patent/KR940005958B1/ko not_active IP Right Cessation
- 1990-11-16 CN CN90109184A patent/CN1028361C/zh not_active Expired - Fee Related
- 1990-11-16 MY MYPI90002027A patent/MY104782A/en unknown
- 1990-11-16 JP JP2311242A patent/JPH03176460A/ja active Granted
- 1990-11-16 HU HU907179A patent/HU207711B/hu not_active IP Right Cessation
- 1990-11-16 CZ CS905685A patent/CZ284374B6/cs not_active IP Right Cessation
- 1990-11-16 PH PH41560A patent/PH27369A/en unknown
- 1990-11-16 SK SK5685-90A patent/SK568590A3/sk unknown
-
1994
- 1994-07-07 CN CN94108400A patent/CN1051991C/zh not_active Expired - Fee Related
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