KR910009706A - 피소스티그민과 관련된 4- 및 6-카바메이트, 이의 제조방법 및 중간 생성물, 및 이의 약제로서의 용도 - Google Patents
피소스티그민과 관련된 4- 및 6-카바메이트, 이의 제조방법 및 중간 생성물, 및 이의 약제로서의 용도 Download PDFInfo
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- KR910009706A KR910009706A KR1019900017657A KR900017657A KR910009706A KR 910009706 A KR910009706 A KR 910009706A KR 1019900017657 A KR1019900017657 A KR 1019900017657A KR 900017657 A KR900017657 A KR 900017657A KR 910009706 A KR910009706 A KR 910009706A
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- KR
- South Korea
- Prior art keywords
- compound
- cis
- hydrogen
- alkyl
- pharmaceutically acceptable
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- 239000003814 drug Substances 0.000 title claims 2
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 title 1
- 229960001697 physostigmine Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 230000003287 optical effect Effects 0.000 claims 4
- -1 carbamate compound Chemical class 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 150000001602 bicycloalkyls Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical group C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 일반식(Ⅰ)의 화합물 또는 3aS-시스 및 3aR-시스광학 이성체를 포함하는 광학 이성체, 또는 라세미 혼합물 또는 약제학적으로 허용되는 이의 산부가염.상기식에서, R1은 알킬, 사이클로알킬, 비사이클로알킬, 아릴 또는 아릴 저급 알킬이고; R2는 수소 또는 알킬이거나, 그룹 -NR1R2는 함께 탄소수 5내지 12의 모노사이클릭 또는 비사이클릭 환을 형성하고; m은 0,1 또는 2이며; X는 각각 독립적으로 수소, 할로겐, 저급 알킬, 니트로 또는 아미노이다.
- 제1항에 있어서, 그룹이 환의 6- 위치에 존재하는 화합물.
- 제1항에 있어서, 그룹이 환의 4- 위치에 존재하는 화합물.
- 제2항에 있어서, X가 수소인 화합물.
- 제4항에 있어서, R1이 저급 알킬, 사이클로알킬, 비사이클로알킬, 아릴 또는 아릴 저급 알킬이고, R2가 수소인 화합물.
- 제5항에 있어서, R1이 저급 알킬, 사이클로알킬인 화합물.
- 제6항에 있어서, 시스-(±)-1,2,3,3a,8,8a-헥사하이드로-1,3a,8-트리메틸피롤로[2,3-b]인돌-6-일 메틸카바메이트인 화합물 또는 이의 3aS-시스 또는 3aR-시스 이성체 또는 약제학적으로 허용되는 이의 산부가염.
- 제6항에 있어서, 시스-(±)-5-브로모-1,2,3,3a,8,8a-헥사하이드로-1,3a,8-트리메틸피롤로[2,3-b]인돌-6-일 메틸카바메이트인 화합물 또는 이의 3aS-시스 또는 3aR-시스 이성체 또는 약제학적으로 허용되는 이의 산부가염.
- 제6항에 있어서, 시스-(±)-1,2,3,3a,8,8a-헥사하이드로-1,3a,8-트리메틸피롤로[2,3-b]인돌-4-일 메틸카바메이트인 화합물 또는 이의 3aS-시스 또는 3aR-시스 이성체 또는 약제학적으로 허용되는 이의 산부가염.
- 제6항에 있어서, 시스-(±)-1,2,3,3a,8,8a-헥사하이드로-1,3a,8-트리메틸피롤로[2,3-b]인돌-4-일 사이클로헥실카바메이트인 화합물 또는 이의 3aS-시스 또는 3aR-시스 이성체 또는 약제학적으로 허용되는 이의 산부가염.
- 활성성분으로서 제1항에서 정의된 화합물 및 이를 위한 적합한 담체를 함유하는 약제학적 조성물.
- 알쯔하이머병(Alzheimer's disease)에서와 같이 저하된 콜린 기능에 의해 특징지워지는 기억장애를 완화시키기 위한 약제의 제조를 위한 제1항에서 정의된 화합물의 용도.
- a)일반식(Ⅲ)의 화합물을 비사이클릭 아미딘 촉매 존재하에 불활성 용매중에서 일반식(a)의 이소시아네이트와 반응시키거나, b) 일반식(Ⅲ)의 화합물을 불활성 용매중에서 1,1′-카보닐디이미다졸과 반응시킨 후 탄소수 5내지 12의 모노사이클릭 또는 비사이클릭 아민을 첨가함을 특징으로 하여, 제1항에서 정의된 화합물을 제조하는 방법.R1-N=C=O (a)상기식에서, R1은 상기 정의한 바와 동일하고; R3은 수소이며; R5는 메틸이고; X 및 m은 상기 정의한 바와 동일하다.
- 일반식(Ⅱ)의 화합물 또는 약제학적으로 허용되는 이의 산부가염.상기식에서, R3은 수소 또는 알킬이고; R4는 수소, 시아노알킬 또는 아미노알킬이며; R6은 수소 또는 알킬이고; m은 0,1 또는 2이며; X는 각각 독립적으로 수소, 할로겐, 저급알킬, 니트로 또는 아미노이다.
- 일반식(Ⅲ)의 화합물 또는 3aS-시스 또는 3aR-시스광학 이성체를 포함하는 이의 광학 이성체, 라세미 혼합물 또는 약제학적으로 허용되는 이의 산부가염.상기식에서, R3은 수소 또는 알킬이고; R5는 수소 또는 알킬이고; m은 0,1 또는 2이며; X는 각각 독립적으로 수소, 할로겐, 저급알킬, 니트로 또는 아미노이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/413,901 US4914102A (en) | 1989-09-28 | 1989-09-28 | N-aminocarbamates related to physostigmine, pharmacentical compositions and use |
US431103 | 1989-11-03 | ||
US07/431,103 US5081117A (en) | 1989-09-28 | 1989-11-03 | 4- and 6-carbamates related to physostigmine and intermediates for the preparation thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
KR910009706A true KR910009706A (ko) | 1991-06-28 |
KR100189665B1 KR100189665B1 (ko) | 1999-06-01 |
Family
ID=40149690
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019900017657A KR100189665B1 (ko) | 1989-09-28 | 1990-11-01 | 피소스티그민과 관련된 4- 및 6-카바메이트, 이의 제조방법 및 이의 중간체 |
Country Status (21)
Country | Link |
---|---|
US (2) | US4914102A (ko) |
EP (2) | EP0420140B1 (ko) |
JP (2) | JPH0723377B2 (ko) |
KR (1) | KR100189665B1 (ko) |
AT (2) | ATE156825T1 (ko) |
AU (3) | AU639943B2 (ko) |
CA (2) | CA2026381A1 (ko) |
CZ (1) | CZ279604B6 (ko) |
DE (2) | DE69031259T2 (ko) |
DK (2) | DK0420140T3 (ko) |
ES (2) | ES2104572T3 (ko) |
FI (2) | FI93961C (ko) |
GR (2) | GR3019468T3 (ko) |
HU (1) | HU206355B (ko) |
IE (1) | IE72153B1 (ko) |
IL (2) | IL95807A (ko) |
NO (2) | NO174469B (ko) |
NZ (2) | NZ235460A (ko) |
PL (1) | PL287618A1 (ko) |
PT (2) | PT95449B (ko) |
ZA (2) | ZA907725B (ko) |
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EP0606366B1 (en) * | 1991-09-26 | 2003-06-04 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA as represented by THE SECRETARY of the DEPARTMENT OF HEALTH AND HUMAN SERVICES | Substituted phenserines and phenylcarbamates of (-)-eseroline, (-)-n1-noreseroline, and (-)-n1-benzylnoreseroline; as specific inhibitors of acetylcholinesterase |
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US5409948A (en) * | 1992-11-23 | 1995-04-25 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Method for treating cognitive disorders with phenserine |
US5665880A (en) * | 1996-10-31 | 1997-09-09 | Hoechst Marion Roussel, Inc. | Method of preparation of physostigmine carbamate derivatives from eseretholes |
US5677457A (en) * | 1996-12-19 | 1997-10-14 | Hoechst Marion Roussel, Inc. | Method of preparation of physostigmine carbamate derivatives from eseroline ethers |
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CN100375619C (zh) * | 2002-06-14 | 2008-03-19 | 富山化学工业株式会社 | 改善脑功能的药物组合物及其用途 |
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US4914102A (en) * | 1989-09-28 | 1990-04-03 | Hoechst Roussel Pharmaceuticals, Inc. | N-aminocarbamates related to physostigmine, pharmacentical compositions and use |
US5077289A (en) * | 1989-11-30 | 1991-12-31 | Hoechst Roussel Pharmaceuticals Inc. | Memory enhancing and analgesic aminocarbonylcarbamates related to physostigmine |
ES2120407T3 (es) * | 1990-01-22 | 1998-11-01 | Hoechst Marion Roussel Inc | Procedimiento para la sintesis enantioselectiva de oxindoles alquilados, utilizados como productos intermedios en la preparacion de fisostigmina. |
-
1989
- 1989-09-28 US US07/413,901 patent/US4914102A/en not_active Expired - Fee Related
- 1989-11-03 US US07/431,103 patent/US5081117A/en not_active Expired - Fee Related
-
1990
- 1990-09-25 DE DE69031259T patent/DE69031259T2/de not_active Expired - Fee Related
- 1990-09-25 EP EP90118376A patent/EP0420140B1/en not_active Expired - Lifetime
- 1990-09-25 ES ES90118376T patent/ES2104572T3/es not_active Expired - Lifetime
- 1990-09-25 DK DK90118376.4T patent/DK0420140T3/da active
- 1990-09-25 AT AT90118376T patent/ATE156825T1/de not_active IP Right Cessation
- 1990-09-26 NZ NZ235460A patent/NZ235460A/xx unknown
- 1990-09-26 IL IL9580790A patent/IL95807A/en not_active IP Right Cessation
- 1990-09-26 FI FI904730A patent/FI93961C/fi not_active IP Right Cessation
- 1990-09-27 AU AU63227/90A patent/AU639943B2/en not_active Ceased
- 1990-09-27 JP JP2255477A patent/JPH0723377B2/ja not_active Expired - Lifetime
- 1990-09-27 NO NO904209A patent/NO174469B/no not_active IP Right Cessation
- 1990-09-27 PT PT95449A patent/PT95449B/pt not_active IP Right Cessation
- 1990-09-27 CA CA002026381A patent/CA2026381A1/en not_active Abandoned
- 1990-09-27 ZA ZA907725A patent/ZA907725B/xx unknown
- 1990-11-01 FI FI905418A patent/FI92701C/fi not_active IP Right Cessation
- 1990-11-01 KR KR1019900017657A patent/KR100189665B1/ko not_active IP Right Cessation
- 1990-11-01 NZ NZ235921A patent/NZ235921A/en unknown
- 1990-11-01 IL IL9620990A patent/IL96209A/en not_active IP Right Cessation
- 1990-11-02 PL PL28761890A patent/PL287618A1/xx unknown
- 1990-11-02 NO NO904783A patent/NO175980C/no not_active IP Right Cessation
- 1990-11-02 JP JP2295595A patent/JPH0780885B2/ja not_active Expired - Fee Related
- 1990-11-02 CZ CS905407A patent/CZ279604B6/cs not_active IP Right Cessation
- 1990-11-02 PT PT95772A patent/PT95772B/pt not_active IP Right Cessation
- 1990-11-02 IE IE396590A patent/IE72153B1/en not_active IP Right Cessation
- 1990-11-02 AU AU65712/90A patent/AU635575B2/en not_active Ceased
- 1990-11-02 ZA ZA908800A patent/ZA908800B/xx unknown
- 1990-11-02 HU HU906999A patent/HU206355B/hu not_active IP Right Cessation
- 1990-11-02 CA CA002029265A patent/CA2029265C/en not_active Expired - Fee Related
- 1990-11-07 ES ES90121267T patent/ES2085309T3/es not_active Expired - Lifetime
- 1990-11-07 DE DE69025941T patent/DE69025941T2/de not_active Expired - Fee Related
- 1990-11-07 AT AT90121267T patent/ATE135355T1/de not_active IP Right Cessation
- 1990-11-07 DK DK90121267.0T patent/DK0484573T3/da active
- 1990-11-07 EP EP90121267A patent/EP0484573B1/en not_active Expired - Lifetime
-
1993
- 1993-01-27 AU AU32046/93A patent/AU646986B2/en not_active Ceased
-
1996
- 1996-03-29 GR GR960400847T patent/GR3019468T3/el unknown
-
1997
- 1997-10-14 GR GR970402666T patent/GR3025021T3/el unknown
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