KR840009101A - 이미다졸 리딘디온 유도체의 제조방법 - Google Patents
이미다졸 리딘디온 유도체의 제조방법 Download PDFInfo
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- KR840009101A KR840009101A KR1019840002843A KR840002843A KR840009101A KR 840009101 A KR840009101 A KR 840009101A KR 1019840002843 A KR1019840002843 A KR 1019840002843A KR 840002843 A KR840002843 A KR 840002843A KR 840009101 A KR840009101 A KR 840009101A
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- South Korea
- Prior art keywords
- hydrogen
- spiro
- formula
- compound
- amino
- Prior art date
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- 238000000034 method Methods 0.000 title claims 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- -1 carbonyl cyclic compound Chemical class 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- QAHZIGHCEBUNGT-QMGFNSACSA-N (5r,6s,7s,8r,9r)-6,7,8-trihydroxy-9-(hydroxymethyl)-1,3-diazaspiro[4.5]decane-2,4-dione Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)C[C@]11C(=O)NC(=O)N1 QAHZIGHCEBUNGT-QMGFNSACSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- SLTHATJXYPMPML-UHFFFAOYSA-N 2,5-dioxoimidazolidine-4-carboxylic acid Chemical compound OC(=O)C1NC(=O)NC1=O SLTHATJXYPMPML-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- JHDJGVQVVFBVOZ-UHFFFAOYSA-N 7-amino-5-chlorospiro[1h-indole-3,5'-imidazolidine]-2,2',4'-trione Chemical compound NC1=CC(Cl)=CC2=C1NC(=O)C21NC(=O)NC1=O JHDJGVQVVFBVOZ-UHFFFAOYSA-N 0.000 claims 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 1
- CNYIJYMPNWLZQV-UHFFFAOYSA-N O=C1CNC(=O)N1.C1=CC=C2NC=CC2=C1 Chemical compound O=C1CNC(=O)N1.C1=CC=C2NC=CC2=C1 CNYIJYMPNWLZQV-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 235000012501 ammonium carbonate Nutrition 0.000 claims 1
- 239000001099 ammonium carbonate Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims 1
- 230000000802 nitrating effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- NZIDYUNZDZNYKY-UHFFFAOYSA-N spiro[1h-pyrrolo[2,3-c]pyridine-3,5'-imidazolidine]-2,2',4'-trione Chemical compound N1C(=O)NC(=O)C21C1=CC=NC=C1NC2=O NZIDYUNZDZNYKY-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
-
- 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
- C07D487/10—Spiro-condensed systems
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Neurosurgery (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- External Artificial Organs (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- (a)일반식(Ⅲ) 또는 일반식(Ⅳ)의 적절하게 치환된 카보닐 환화합물을 알카리 금속 시이나이드 및 탄산암모늄과 축합시켜, 일반식(Ⅰ) 또는 (Ⅱ)의 상응하는 스피로-옥시인돌 이미다졸리딘 디온 최종 생성물을 형성하거나;(b)소디오 에틸 히단토인-5-카복실레이트를 2,4-디니트로벤전으로 알킬화하고 이어서, 환원적으로 폐환시켜, X 및 Y가 각각 수소이고, Z가 아미노인 일반식(Ⅰ)의 화합물을 형성하거나;(c) 소디오 에틸 히단토인 -5-카복실레이트를 적절한 할로니트로-이치환된 피리딘으로 알킬화하고 이어서, 환원적으로 폐환시켜 R′가 수소인 일반식(Ⅱ)의 화합물을 형성하거나;(d) X, Y 및 Z가 각각 수소인 일반식(Ⅰ)의 화합물을 할로겐화하여, X가 할로겐인 상응하는 5′-할로유도체를 형성하고 이어서, 7′-위치를 니트로화하고 계속해서 환원시켜 X가 할로겐이고, Y가 아미노이며 Z가 수소인 일반식(Ⅰ)의 화합물을 형성시키고, 그후, 경우에 따라 R′가 수소인 일반식(Ⅱ)의 화합물을 R′가 수소가 아닌 상응하는 화합물로 전환시키고; 경우에 따라 일반식(Ⅰ) 또는 (Ⅱ)의 화합물을 그의 약제학적으로 허용되는 염으로 전환시킴을 특징으로 하여, 일반식(Ⅰ) 및 (Ⅱ)의 스피로-히단토인 유도체 및 그의 약제학적으로 허용되는 염을 제조하는 방법.상기식에서,X 및 Y는 각각 수소, 불소, 염소, 브롬, 니트로 또는 아미고이고;Z는 수소 또는 아미노이며 단, X 및 Y중 적어도 하나가 수소가 아닌 경우, Z는 반드시 아미노가 아니며;R은 수소, 아릴 및 알킬 부분의 탄소수가 3 이하인 아르알킬그룹중에서 선택되고, 여기에서 각 경우에 아릴부분은 피리딜; 또는 불소, 염소, 브롬 및 탄소수 1 내지 4의 알킬그룹중에서 선택된 치환체로 환이 치환된 피리딜을 나타내며, 단 X, Y 및 Z가 각각 아미노가 아닌 경우 R은 반드시 수소가 아니고;일반식(Ⅱ)에서 =A-B=D-은 =N-CH=CH-, =CH-CH=N- 또는 =CH-N=CH-을 나타내며; R′은 수소, 탄소수 1 내지 4의 알킬, 아릴 및 알킬부분의 탄소수가 3 이하인 아르알킬그룹 중에서 선택되고, 여기에서 각 경우에 아릴 부분은 피리딜;티에닐;페닐;또는 불소, 염소, 브롬, 각각 탄소수 4이하인 알킬 또는 알콕시, 또는 트리플루오로메틸중에서 선택된 치환체로 환이 일- 및 이- 치환된 페닐을 나타내며 ;R″은 수소, 하이드록시, 불소, 염소, 각각 탄소수 4 이하인 알킬 또는 알콕시, 또는 트리플루오로메틸이다.
- 제1항에 있어서, 방법(a)의 반응을 카보닐 환화합물 출발물질에 대해 알카리금속 시아나이드 반응물을 적어도 약간 몰과량으로 사용하여 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 방법(a)의 반응을 반응-불활성인 극성유기용매중의 약 50 내지 150℃ 온도에서 수행함을 특징으로 하는 방법.
- 제3항에 있어서, 상기 용매가 수혼화성 저급알칸올임을 특징으로 하는 방법.
- 제1항에 있어서, 방법(a)에서 생성된 스피로-히단토인 유도체가 1′-3(-피리딜메틸)-5′-플루오로-스피로-[이미다졸리딘-4.3′-인돌린]-2,2′,5-트리온인 방법.
- 제1항에 있어서, 방법(a)에서 생성된 스피로-히단토인 유도체가 1′-3(-피리딜메틸)-5′,7′-플루오로-스피로-[이미다졸리딘-4.3′-인돌린]-2,2,5-트리온인 방법.
- 제1항에 있어서, 방법(b) 또는 (c)의 환원적 폐환단계를 약 20 내지 100℃ 온도에서, 산존재하에 철가루를 사용하여 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 방법(c)에서 생성된 스피로-히단토인 유도체가 스피로-[이미다졸리딘-4.3′-(6-아자인돌린)]-2,2′,5-트리온인 방법.
- 제1항에 있어서, 방법(d)의 환원단계를 백금, 팔라듐 또는 니켈촉매를 사용하는 촉매적 수소화반응에 의해 수행함을 특징으로 하는 방법.
- 제1항에 있어서, 방법(d)에서 생성된 스피로-히단토인 유도체가 5′-클로로-7′-아미노-스피로-[이미다졸리딘-4.3′-인돌린]-2,2′,5-트리온인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019860007876A KR860001870B1 (ko) | 1983-05-25 | 1986-09-20 | 이미다졸리딘디온 유도체의 제조방법 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US497962 | 1983-05-25 | ||
| US497,962 | 1983-05-25 | ||
| US06/497,962 US4464380A (en) | 1983-05-25 | 1983-05-25 | Imidazolidinedione derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860007876A Division KR860001870B1 (ko) | 1983-05-25 | 1986-09-20 | 이미다졸리딘디온 유도체의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840009101A true KR840009101A (ko) | 1984-12-24 |
| KR860001869B1 KR860001869B1 (ko) | 1986-10-24 |
Family
ID=23979057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840002843A KR860001869B1 (ko) | 1983-05-25 | 1984-05-24 | 이미다졸리딘디온 유도체의 제조방법 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4464380A (ko) |
| EP (1) | EP0127412B1 (ko) |
| JP (1) | JPS604183A (ko) |
| KR (1) | KR860001869B1 (ko) |
| AT (1) | ATE57531T1 (ko) |
| AU (1) | AU543916B2 (ko) |
| CA (1) | CA1266270A (ko) |
| DE (1) | DE3483402D1 (ko) |
| DK (1) | DK163924C (ko) |
| ES (2) | ES532736A0 (ko) |
| FI (1) | FI78699C (ko) |
| GR (1) | GR82020B (ko) |
| HU (1) | HU190548B (ko) |
| IE (1) | IE57520B1 (ko) |
| IL (1) | IL71904A (ko) |
| PH (1) | PH21151A (ko) |
| PL (3) | PL252850A1 (ko) |
| PT (1) | PT78625A (ko) |
| YU (2) | YU43931B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0172719B1 (en) * | 1984-08-20 | 1988-09-21 | Pfizer Inc. | Process for the production as asymmetric hydantoins |
| US4762839A (en) * | 1985-06-06 | 1988-08-09 | Tanabe Seiyaku Co., Ltd. | Quinazolinone copmpounds useful for the prophyloxis and treatment of diabetic complications |
| JPS63132889A (ja) * | 1986-11-21 | 1988-06-04 | Tanabe Seiyaku Co Ltd | キナゾリノン誘導体 |
| US4841079A (en) * | 1987-08-07 | 1989-06-20 | Pfizer, Inc. | Process for the production of asymmetric hydantoins |
| EP0769497B1 (de) * | 1995-10-18 | 2002-12-18 | F. Hoffmann-La Roche Ag | Hydroxymethylierung von Tocopherolen |
| JP4601175B2 (ja) | 1998-12-19 | 2010-12-22 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 抗ヒスタミン性スピロ化合物 |
| JP2009526044A (ja) * | 2006-02-07 | 2009-07-16 | アストラゼネカ・アクチエボラーグ | 新規な化合物ｉ |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3821383A (en) * | 1972-07-10 | 1974-06-28 | Ayerst Mckenna & Harrison | Compositions for and a method of treating diabetic complications |
| US4200642A (en) * | 1978-08-21 | 1980-04-29 | Pfizer Inc. | Spiro-oxazolidindiones |
| ZA806623B (en) * | 1979-11-13 | 1981-12-30 | Ici Ltd | Substituted indoline-2-one derivatives |
| AU532110B2 (en) * | 1979-11-13 | 1983-09-15 | Ici Ltd. | Spiro(imidazolidine-4,3:-indoline)-2,2:5-trione derivatives |
| US4248882A (en) * | 1980-02-12 | 1981-02-03 | Pfizer Inc. | Treating diabetes-associated complications with hydantoin amines |
| IE52879B1 (en) * | 1981-05-12 | 1988-03-30 | Ici Plc | Pharmaceutical spiro-hydantoin derivatives |
-
1983
- 1983-05-25 US US06/497,962 patent/US4464380A/en not_active Expired - Fee Related
-
1984
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1985
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1986
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