KR850006171A - 피롤리디논 유도체의 제조방법 - Google Patents
피롤리디논 유도체의 제조방법 Download PDFInfo
- Publication number
- KR850006171A KR850006171A KR1019850001130A KR850001130A KR850006171A KR 850006171 A KR850006171 A KR 850006171A KR 1019850001130 A KR1019850001130 A KR 1019850001130A KR 850001130 A KR850001130 A KR 850001130A KR 850006171 A KR850006171 A KR 850006171A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- hydrogen
- carbon atoms
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- 150000004040 pyrrolidinones Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- -1 1,4-butylene Chemical group 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 하기 식(2)의 화합물을 N-탈보호시켜 하기 식(3)의 화합물을 생성하여 분자내에 고리화 반응을 일으킴으로써 하기 식(1)의 피롤리디논 유도체를 제조하는 방법.상기 식(2)에서 R1은 수소이며 R2는 벤질 또는 치환된 벤질이며, 또는 R1과 R2는 둘다기를 형성할 수 있는데 여기서, R4와 R5는 각각 수소, 1 내지 4 탄소수의 알킬, 페닐 또는 임의적으로 치환된 알릴이거나 또는 둘 모두 1,4-부틸렌 또는 1,5-펜틸렌(-(CH2)5)-이다; R3는 수소 1 내지 4 탄소수의 직쇄알킬 또는 측쇄알킬이며; 임의적으로 R3가 수소일때 수소일때 생성물은 R이 아실 또는 알릴인 화합물로 전환될 수 있으며; X는 1 내지 10 탄소수의 직쇄알킬 또는 측쇄알킬이다.
- 제1항에 있어서 R1과 R2둘 모두는기를 형성할 수 있으며, 탈보호반응과 분자내 고리화 반응은 카르복실산 존재하에 90℃ 내지 160℃의 온도범위에서 가열하는 것을 특징으로 하는 방법.
- 제1항 또는 2항에 있어서 R1과 R2는 둘다 2-메틸-프리핀-1,1-디일기(CHCH(CH3)2)를 형성할 수 있으며 R3는 수소인 것을 특징으로 하는 방법.
- 제1항에 있어서 R2는 벤질 또는 치환된 벤질이며, 식(2)의 화합물을 목탄에 팔라듐이 입혀져 있는 촉매와의 촉매 수소화 반응에 의해 탈보호화시키는 것을 특징으로 하는 방법.
- 제1항 내지 4항중 어느 한 항에 있어서, 하기 식(4) 알킬 3,4-에폭시부타노에이트와 하기 식(5)의 글리신아미드 유도체를 반응시켜 R3가 수소인 식(2)의 화합물을 제조하는 방법.상기 식에서 X는 1 내지 10 탄소수의 알킬이며, R1과 R2는 제1항 내지 4항에서 정의된 것과 같으며 임의적으로 R3가 1 내지 4의 탄소수의 직쇄알킬 또는 측쇄알킬일때 생성물은 식(2)의 화합물로 전환될 수 있다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT8419802A IT1206699B (it) | 1984-02-27 | 1984-02-27 | Procedimento per preparare derivati di pirrolidone. |
IT19802A/84 | 1984-02-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850006171A true KR850006171A (ko) | 1985-10-02 |
KR920002295B1 KR920002295B1 (ko) | 1992-03-21 |
Family
ID=11161351
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019850001130A KR920002295B1 (ko) | 1984-02-27 | 1985-02-22 | 프롤리디논 유도체의 제조방법 |
Country Status (20)
Country | Link |
---|---|
US (1) | US4797496A (ko) |
EP (1) | EP0154490B1 (ko) |
JP (1) | JPH0791266B2 (ko) |
KR (1) | KR920002295B1 (ko) |
AT (1) | ATE36319T1 (ko) |
AU (2) | AU584605B2 (ko) |
CA (1) | CA1241333A (ko) |
DE (1) | DE3564264D1 (ko) |
DK (1) | DK86185A (ko) |
ES (2) | ES8700656A1 (ko) |
FI (1) | FI81339C (ko) |
GR (1) | GR850485B (ko) |
HU (2) | HU193399B (ko) |
IL (1) | IL74448A (ko) |
IT (1) | IT1206699B (ko) |
NO (1) | NO166712C (ko) |
NZ (1) | NZ211226A (ko) |
PH (1) | PH22518A (ko) |
PT (1) | PT80021B (ko) |
ZA (1) | ZA851401B (ko) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4686296A (en) * | 1985-07-26 | 1987-08-11 | Denki Kagaku Kogyo Kabushiki Kaisha | Process for producing oxiracetam |
CH668423A5 (de) * | 1986-06-19 | 1988-12-30 | Lonza Ag | Verfahren zur herstellung von 4-alkoxy-3-pyrrolin-2-onen. |
CH666891A5 (de) * | 1985-11-26 | 1988-08-31 | Lonza Ag | 4-alkoxy-2-oxo-pyrrolidin-1-yl-essigsaeure-c(1)-c(4)-alkylester, deren herstellung und verwendung. |
DE3602254A1 (de) * | 1986-01-25 | 1987-07-30 | Basf Ag | Verfahren zur herstellung von oxiranylcarbonsaeureestern |
CH680293A5 (ko) * | 1990-06-26 | 1992-07-31 | Lonza Ag | |
KR100424393B1 (ko) * | 2001-11-26 | 2004-03-24 | 한국화학연구원 | 옥시라세탐의 제조방법 |
CN101704778B (zh) * | 2009-09-30 | 2012-10-17 | 厦门市华兴化工有限公司 | 一种制备4-羟基吡咯烷酮-2-乙酰胺的方法 |
CN102249977B (zh) * | 2011-08-11 | 2013-06-12 | 重庆润泽医药有限公司 | 4-羟基-2-氧代-1-吡咯烷乙酰胺外消旋体晶型ⅰ及其制备方法 |
CN102432516B (zh) * | 2011-12-14 | 2013-10-09 | 山东阿如拉药物研究开发有限公司 | 奥拉西坦的精制方法 |
CN110615744B (zh) * | 2018-06-20 | 2023-01-06 | 上海朴颐化学科技有限公司 | 一种布瓦西坦中间体及其制备方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI51098C (fi) * | 1975-03-27 | 1976-10-11 | Medipolar Oy | Menetelmä terapeuttisesti arvokkaan 2-okso-1-pyrrolidinyyliasetamidin valmistamiseksi. |
IT1045043B (it) * | 1975-08-13 | 1980-04-21 | Isf Spa | Derivati pirrolidinici |
IT1075280B (it) * | 1977-02-11 | 1985-04-22 | Isf Spa | Procedimento per la preparazione di derivati pirrolidinici |
IT1075564B (it) * | 1977-02-11 | 1985-04-22 | Isf Spa | Procedimento per la preparazione di derivati pirrolidinici |
JPS5812272B2 (ja) * | 1981-04-28 | 1983-03-07 | 電気化学工業株式会社 | 4−ヒドロキシ−2−ピロリドンの製造法 |
FR2515179A1 (fr) * | 1981-07-24 | 1983-04-29 | Hoffmann La Roche | Derives de pyrrolidine, leur procede de preparation, les intermediaires pour leur synthese et leur application therapeutique |
IT1173768B (it) * | 1984-04-02 | 1987-06-24 | Isf Spa | Procedimento di preparazione di derivati 1-carbamoilmetilici di 4-idrossi-2-osso-pirrolidina nonche' di intermedi per ottenere tali composti |
-
1984
- 1984-02-27 IT IT8419802A patent/IT1206699B/it active
-
1985
- 1985-02-07 FI FI850505A patent/FI81339C/fi not_active IP Right Cessation
- 1985-02-14 CA CA000474316A patent/CA1241333A/en not_active Expired
- 1985-02-21 ES ES540601A patent/ES8700656A1/es not_active Expired
- 1985-02-22 KR KR1019850001130A patent/KR920002295B1/ko not_active IP Right Cessation
- 1985-02-25 ZA ZA851401A patent/ZA851401B/xx unknown
- 1985-02-26 AT AT85301278T patent/ATE36319T1/de not_active IP Right Cessation
- 1985-02-26 EP EP85301278A patent/EP0154490B1/en not_active Expired
- 1985-02-26 DK DK86185A patent/DK86185A/da not_active Application Discontinuation
- 1985-02-26 NO NO850778A patent/NO166712C/no unknown
- 1985-02-26 GR GR850485A patent/GR850485B/el unknown
- 1985-02-26 HU HU85705A patent/HU193399B/hu not_active IP Right Cessation
- 1985-02-26 DE DE8585301278T patent/DE3564264D1/de not_active Expired
- 1985-02-26 IL IL74448A patent/IL74448A/xx unknown
- 1985-02-26 NZ NZ211226A patent/NZ211226A/xx unknown
- 1985-02-26 AU AU39180/85A patent/AU584605B2/en not_active Ceased
- 1985-02-27 PH PH31916A patent/PH22518A/en unknown
- 1985-02-27 JP JP60038625A patent/JPH0791266B2/ja not_active Expired - Lifetime
- 1985-02-27 PT PT80021A patent/PT80021B/pt not_active IP Right Cessation
-
1986
- 1986-03-13 ES ES552957A patent/ES8800135A1/es not_active Expired
- 1986-03-26 HU HU861280A patent/HU195957B/hu not_active IP Right Cessation
-
1988
- 1988-03-08 US US07/165,340 patent/US4797496A/en not_active Expired - Lifetime
-
1989
- 1989-02-23 AU AU30247/89A patent/AU612000B2/en not_active Ceased
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