KR840006641A - 2,6-피페리딘디온 유도체의 제조방법 - Google Patents
2,6-피페리딘디온 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840006641A KR840006641A KR1019830005288A KR830005288A KR840006641A KR 840006641 A KR840006641 A KR 840006641A KR 1019830005288 A KR1019830005288 A KR 1019830005288A KR 830005288 A KR830005288 A KR 830005288A KR 840006641 A KR840006641 A KR 840006641A
- Authority
- KR
- South Korea
- Prior art keywords
- group
- hydrogen atom
- piperidinedione
- alkyl group
- derivative
- Prior art date
Links
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical class O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 title claims 5
- 238000000034 method Methods 0.000 title claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 238000010438 heat treatment Methods 0.000 claims 4
- 239000012442 inert solvent Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
- 150000002825 nitriles Chemical class 0.000 claims 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- CNMOHEDUVVUVPP-UHFFFAOYSA-N piperidine-2,3-dione Chemical compound O=C1CCCNC1=O CNMOHEDUVVUVPP-UHFFFAOYSA-N 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 3
- 238000007363 ring formation reaction Methods 0.000 claims 3
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 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
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 claims 1
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 유기 또는 무기 염기의 존재하에 피리딜아세토니트릴을 다음 일반식(2)의 화합물로써 알킬화시키고 이의 생성물을 4급 암모니움 하이드록시드의 존재하에 다음 일반식(4)의 α불포화 니트릴과 반응시킨 다음, 산 성매질내에서 가열시켜 고리화 시킴을 특징으로 하는 일반식(Ⅰ)의 2,6-피페리딘디온 유도체의제조방법.상기식에서, R은 탄소수 2내지 5인 직쇄 또는 측쇄의 알킬 그룹이거나,그룹이 1내지 4의 메틸그룹에 의해 쉽게 치환될 수 있는 모포리노 또는 피페리디노 그룹을 나타내며; n은 2 또는 3의 수이며, R1,R2및 R3는 독립적으로수소원자 또는 저급알킬그룹을 나타내거나, R2및 R3가 모두(CH2)p)여기서 p는 3 또 4의 수임) 그룹을 나타내며 (단, 이 경우 R1은 H임); R4및 R5는수소원자이며; 피페리딘디온은피리딜 그룹의 2′,3′또는 4′에 위치한다.
- 피리딜아세토니트릴을 다음 일반식(6)의 카보닐 유도체와 반응시키고; 이의 생성물을 접촉 환원시켜 불포화 유도체를 이에 상응하는 포화유도체로 전환시키고; 상기 포화유도체인 알파-니트릴을 다음 일반식(2)의 화합물과 반응시킨 다음; 산성 매질 내에서 가열시켜 고리화시킴을 특징으로 하는 일반식(Ⅰ)의 2,6-피페리딘디온 유도체의 제조방법.상기식에서, R은 탄소수 2내지 5인 직쇄 또는 측쇄의 알킬그룹이거나,그룹이 1내지 4의 메틸 그룹에 의해 쉽게 치환될 수 있는 모포리노 또는 피페리디노 그룹을 나타내; n며 2은 또는 3의 수이며, R1,R2및 R5는 수소원자이며; R3및 R4는 CH3이며; 피페리딘디온 은피리딜 그룹의 2′,3′ 또는 4′에 위치한다.
- 디이소프로필아미드의 존재하에, 용매 내에서 저온하에 다음 일반식(10)의 불포화니트릴을 다음 일반식(11)의 니트릴과 반응시키고; 상기 생성물을 불활성용매내에서 소다화제의 존재하에 다음 일반식(2)의 할로겐 유도체와 반응시킨 다음; 산성 매질 내에서 가열시켜 고리화 시킴을 특징으로 하는 다음 일반식(Ⅰ)의 2,6-피페리딘디온 유도체의 제조방법.상기식에서, R은 탄소수 2내지 5인 직쇄 또는 측쇄의 알킬그룹 이거나,그룹이 1내지 4의 메틸그룹에 의해 쉽게 치환될 수 있는 모포리노 또는 피페리디노 그룹을 나타내며; n은 2 또는 3의 수이며; R1및 R2는 독립적으로 수소원자 또는 저급 알킬 그룹을 나타내며; R3및 R4는 독립적으로 수소원자 또는 저급 알킬그룹을 나타내거나, 모두(CH2)m (여기서, m은 4 또는 5의 수임) 그룹을 나타내거나, 또는 R2및 R3모두 (CH2)p (여기서, p는 3 또는 4의 수임) 그룹을 나타내며 (이 경우, R1및 R4는 수소원자임); R5는 수소원자이며; 피페리딘디온은 피리딜 그룹의 2′,3′ 또는 4′에 위치한다.
- 리튬 디에틸아미드의 존재하에, 불활성 용매내에서 주위 온도하에 다음 일반식(11)의 니트릴을 1-클로로 2-브로모 에탄과 반응시키고; 용매내에서, 40∼60℃의 온도하에 상기 생성물을 테트라에틸암모니움 시아나이드와 반응시키고; 리튬 디이소프로필 아미드의 존재하에, 불활성 용매 내에서-10내지-20℃의 온도하에 상기에서 생성된 디니트릴을 브로모피리딘과 반응시키고; 소다화제의 존재하에 불활성 용매내에서 상기 생성물을 다음 일반식(2)의 할로겐 유도체와 반응시킨 다음; 산성 매질내에서 가열시켜 고리화시킴을 특징으로 하는 일반식(Ⅰ)의 2,6-피페리딘디온 유도체의 제조방법.상기식에서, R은 탄소수 2내지 5인 직쇄 또는 측쇄의 알킬그룹이거나,그룹이 1내지 4의 메틸그룹에 의해 쉽게 치환될 수 있는 모포리노 또는 피페리디노 그룹을 나타내며; n은 2 또는 3의 수이며; R1및 R2는 독립적으로 수소원자 또는 저급 알킬그룹을 나타내며; R3및 R4는 독립적으로 수소원자 또는 저급 알킬 그룹을 나타내거나, 모두(CH2)m (여기서, m은 4 또는 5의 수임) 그룹을 나타내거나, 또는 R2및 R3모두 (CH2)p (여기서, p는 3 또는 4의 수임) 그룹을 나타내며 (이 경우, R1및 R4는 수소임); R5는 수소원자이며;피페리딘디온은 피리딜그룹의 2′,3′ 또는 4′에 위치한다.
- 제1항 내지 4항에 있어서, R5가 수소원자인 일반식(Ⅰ)의 화합물을 질소 가스체하에 공지의 방법으로 알킬화시켜 수소원자를 전환시킴으로써 R5가 알킬인화합물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR82-18706 | 1982-11-08 | ||
| FR8218706 | 1982-11-08 | ||
| FR8218706A FR2535721A1 (fr) | 1982-11-08 | 1982-11-08 | Derives de la piperidinedione protecteurs du myocarde presentant une acticite antiarythmique, leur procede de preparation et les medicaments qui contiennent lesdits derives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840006641A true KR840006641A (ko) | 1984-12-01 |
| KR900006721B1 KR900006721B1 (ko) | 1990-09-20 |
Family
ID=9279000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830005288A KR900006721B1 (ko) | 1982-11-08 | 1983-11-08 | 2,6-피페리딘디온 유도체의 제조방법 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4721710A (ko) |
| EP (1) | EP0110755B1 (ko) |
| JP (1) | JPS59161377A (ko) |
| KR (1) | KR900006721B1 (ko) |
| AT (1) | ATE22561T1 (ko) |
| AU (1) | AU565519B2 (ko) |
| CA (1) | CA1221967A (ko) |
| CS (1) | CS244681B2 (ko) |
| DD (3) | DD229407A5 (ko) |
| DE (1) | DE3366623D1 (ko) |
| DK (1) | DK511383A (ko) |
| ES (1) | ES527091A0 (ko) |
| FI (1) | FI79536C (ko) |
| FR (1) | FR2535721A1 (ko) |
| GR (1) | GR78747B (ko) |
| HU (1) | HU191494B (ko) |
| IE (1) | IE56209B1 (ko) |
| IL (1) | IL70099A (ko) |
| MA (1) | MA19948A1 (ko) |
| NO (1) | NO159852C (ko) |
| NZ (1) | NZ206177A (ko) |
| OA (1) | OA07582A (ko) |
| PH (1) | PH20421A (ko) |
| PL (3) | PL139946B1 (ko) |
| PT (1) | PT77607B (ko) |
| SG (1) | SG1989G (ko) |
| SU (3) | SU1333237A3 (ko) |
| YU (3) | YU221183A (ko) |
| ZA (1) | ZA838065B (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4668689A (en) * | 1984-07-19 | 1987-05-26 | National Research Development Corporation | Glutarimide derivatives for treating oestrogen-dependent tumors |
| US5238947A (en) * | 1990-04-12 | 1993-08-24 | University Of Georgia Research Foundation, Inc. | Synthetic piperidinediones with cytostatic activity |
| AU2012255860C1 (en) | 2011-05-17 | 2015-12-10 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| WO2012158795A1 (en) | 2011-05-17 | 2012-11-22 | Principia Biopharma Inc. | Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors |
| DK2710007T3 (da) | 2011-05-17 | 2020-01-27 | Principia Biopharma Inc | Kinasehæmmere |
| EP2892900B1 (en) | 2012-09-10 | 2017-08-16 | Principia Biopharma Inc. | Pyrazolopyrimidine compounds as kinase inhibitors |
| US8957080B2 (en) | 2013-04-09 | 2015-02-17 | Principia Biopharma Inc. | Tyrosine kinase inhibitors |
| SG11201606858RA (en) | 2014-02-21 | 2016-09-29 | Principia Biopharma Inc | Salts and solid form of a btk inhibitor |
| ES2843323T3 (es) | 2014-12-18 | 2021-07-16 | Principia Biopharma Inc | Tratamiento de pénfigo |
| TW201718572A (zh) | 2015-06-24 | 2017-06-01 | 普林斯匹亞生物製藥公司 | 酪胺酸激酶抑制劑 |
| IL263815B (en) | 2016-06-29 | 2022-07-01 | Principia Biopharma Inc | Modified release formulations of 2-[3-[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[4,3-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4 -Methyl-4-[4-(Oxtan-3-yl)piperazin-1-yl)pent-2-ananitrile |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2664424A (en) * | 1953-12-29 | Dioxo-piperidines | ||
| GB1455687A (en) * | 1972-12-28 | 1976-11-17 | Aspro Nicholas Ltd | Pharmacologically active 3-phenyl-3-aminoalkyl-2,6-dioxo-hydro genated pyridines |
| FR2467200A1 (fr) * | 1979-10-11 | 1981-04-17 | Clin Midy | Derives du pyrrole actifs sur les troubles du rythme cardiovasculaire |
-
1982
- 1982-11-08 FR FR8218706A patent/FR2535721A1/fr active Granted
-
1983
- 1983-10-28 ZA ZA838065A patent/ZA838065B/xx unknown
- 1983-10-31 IL IL70099A patent/IL70099A/xx unknown
- 1983-11-02 AU AU20898/83A patent/AU565519B2/en not_active Ceased
- 1983-11-04 PT PT77607A patent/PT77607B/pt not_active IP Right Cessation
- 1983-11-04 IE IE2581/83A patent/IE56209B1/xx unknown
- 1983-11-04 EP EP83402142A patent/EP0110755B1/fr not_active Expired
- 1983-11-04 AT AT83402142T patent/ATE22561T1/de not_active IP Right Cessation
- 1983-11-04 GR GR72874A patent/GR78747B/el unknown
- 1983-11-04 DE DE8383402142T patent/DE3366623D1/de not_active Expired
- 1983-11-05 SU SU833661804A patent/SU1333237A3/ru active
- 1983-11-07 NZ NZ206177A patent/NZ206177A/en unknown
- 1983-11-07 MA MA20168A patent/MA19948A1/fr unknown
- 1983-11-07 DD DD83270120A patent/DD229407A5/de not_active IP Right Cessation
- 1983-11-07 NO NO834057A patent/NO159852C/no unknown
- 1983-11-07 DD DD83270121A patent/DD229402A5/de not_active IP Right Cessation
- 1983-11-07 DD DD83256411A patent/DD219770A5/de not_active IP Right Cessation
- 1983-11-08 FI FI834087A patent/FI79536C/fi not_active IP Right Cessation
- 1983-11-08 PL PL1983244462A patent/PL139946B1/pl unknown
- 1983-11-08 ES ES527091A patent/ES527091A0/es active Granted
- 1983-11-08 YU YU02211/83A patent/YU221183A/xx unknown
- 1983-11-08 OA OA58153A patent/OA07582A/xx unknown
- 1983-11-08 HU HU833827A patent/HU191494B/hu not_active IP Right Cessation
- 1983-11-08 CS CS838220A patent/CS244681B2/cs unknown
- 1983-11-08 JP JP58209772A patent/JPS59161377A/ja active Pending
- 1983-11-08 PL PL1983249749A patent/PL140992B1/pl unknown
- 1983-11-08 DK DK511383A patent/DK511383A/da not_active Application Discontinuation
- 1983-11-08 CA CA000440675A patent/CA1221967A/en not_active Expired
- 1983-11-08 PL PL1983249750A patent/PL140021B1/pl unknown
- 1983-11-08 KR KR1019830005288A patent/KR900006721B1/ko active IP Right Grant
- 1983-11-08 PH PH29800A patent/PH20421A/en unknown
-
1984
- 1984-09-06 SU SU843786916A patent/SU1333238A3/ru active
- 1984-09-06 SU SU843786907A patent/SU1316558A3/ru active
-
1985
- 1985-11-26 YU YU01841/85A patent/YU184185A/xx unknown
- 1985-11-26 YU YU01842/85A patent/YU184285A/xx unknown
-
1986
- 1986-03-10 US US06/838,255 patent/US4721710A/en not_active Expired - Fee Related
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1989
- 1989-01-11 SG SG19/89A patent/SG1989G/en unknown
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