KR830009086A - 치환된 n-[4-(인돌릴)-피페리디노-알킬]-벤즈이미다졸론의 제조방법 - Google Patents
치환된 n-[4-(인돌릴)-피페리디노-알킬]-벤즈이미다졸론의 제조방법 Download PDFInfo
- Publication number
- KR830009086A KR830009086A KR1019820000868A KR820000868A KR830009086A KR 830009086 A KR830009086 A KR 830009086A KR 1019820000868 A KR1019820000868 A KR 1019820000868A KR 820000868 A KR820000868 A KR 820000868A KR 830009086 A KR830009086 A KR 830009086A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- alkyl
- benzimidazolone
- indolyl
- piperidino
- Prior art date
Links
- 125000001041 indolyl group Chemical group 0.000 title claims 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 231100000331 toxic Toxicity 0.000 claims 4
- 230000002588 toxic effect Effects 0.000 claims 4
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910000510 noble metal Inorganic materials 0.000 claims 2
- -1 3- (4-piperidyl) -indolyl Chemical group 0.000 claims 1
- CIRSPTXGPFAXRE-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-indole Chemical compound C1NCCC(C=2C3=CC=CC=C3NC=2)=C1 CIRSPTXGPFAXRE-UHFFFAOYSA-N 0.000 claims 1
- KAIRZPVWWIMPFT-UHFFFAOYSA-N 3-piperidin-4-yl-1h-indole Chemical compound C1CNCCC1C1=CNC2=CC=CC=C12 KAIRZPVWWIMPFT-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 일반식(II)의 3-(1,2,5,6-테트라하이드로-4-피리딜)-인돌을 일반식(III)의 N-(ω-할로알킬)-벤즈이미다졸론으로 알킬화시켜 일반식(IV)의 중간체를 얻고 이 일반식(IV)의 중간체를 귀금속촉매 존재하에 수소로 수소첨가 반응시켜 일반식(I)의 치환된 N-[4-(인돌릴)-피페리디노-알킬]-벤즈이미다졸론 및 그 약리학적으로 무독한 산부가염을 제조하는 방법.상기식에서,R1은 수소, 할로겐 또는 메톡시이고, R2는 수소 또는 저급알킬이고, R3는 수소 또는 저급알킬이고, R4는 수소, 저급알킬 또는 저급알케닐이고, n은 2 내지 6의 정수이고, X는 염소, 브롬 또는 요드이다.
- 일반식(V)의 3-(4-피페리딜)-인돌을 일반식(III)의 N-(ω-할로-알킬)-벤즈이미다졸론으로 알킬화시켜 상기 1의 일반식(I)의 치환된 N-[4-(인돌릴)-피페리디노-알킬]-벤즈이미다졸론 및 그 약리학적으로 무독한 산부가염을 제조하는 방법.상기식에서, R1, R2, R3, R4, n 및 X는 상기 1에서 정의된 바와 같다.
- 일반식(VI)의 4-피페리돈을 일반식(III)의 N-(ω-할로-알킬)-벤즈이미다졸론으로 알킬화시켜 일반식(VII)의 중간체를 얻은후 이 중간체를 산수용액중에서 일반식(VIII)의 인돌과 반응시켜 일반식(IV)의 상응하는 중간체를 얻은다음 이 일반식(IV)의 중간체를 귀금속 촉매하에 수소로 수소첨가반응시켜 상기 1의 일반식(I)의 치환된 N-[4-(인돌릴)-피페리디노-알킬]-벤즈이미다졸론 및 그 약리학적으로 무독한 산부가염을 제조하는 방법.상기식에서, R1, R2, R3, R4, n 및 X는 상기 1에서 정의된 바와 같다.
- 일반식(V)의 3-(4-피페리딜)-인돌일 일반식(IX)의 α,ω-디할로-알칸으로 알킬화시켜 일반식(X)의 중간체를 얻고 이 일반식(X)의 중간체를 일반식(XI)의 벤즈이미다졸론으로 알킬화시켜 상기 1의 일반식(I)의 치환된 N-[4-(인돌릴)-피페리디노-알킬]-벤즈이미다졸론 및 그 약리학적으로 무독한 산부가염을 제조하는 방법.상기식에서,R1, R2, R3, R4, n 및 X는 상기 1에서 정의된 바와 같다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/237,966 US4359468A (en) | 1981-02-25 | 1981-02-25 | Antiallergic N-[4-(indolyl)-piperidino-alkyl]-benzimidazolones |
US237,966 | 1981-02-25 | ||
US237.966 | 1981-02-25 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830009086A true KR830009086A (ko) | 1983-12-17 |
KR890000008B1 KR890000008B1 (ko) | 1989-03-02 |
Family
ID=22895956
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR8200868A KR890000008B1 (ko) | 1981-02-25 | 1982-02-25 | 치환된 n-[4-(인돌릴)-피페리디노-알킬]-벤즈이미다졸론 및 이의 제조방법 |
Country Status (28)
Country | Link |
---|---|
US (1) | US4359468A (ko) |
EP (1) | EP0058975B1 (ko) |
JP (1) | JPS57156484A (ko) |
KR (1) | KR890000008B1 (ko) |
AR (1) | AR228475A1 (ko) |
AT (1) | ATE10742T1 (ko) |
AU (1) | AU543948B2 (ko) |
CA (1) | CA1191137A (ko) |
CS (1) | CS227343B2 (ko) |
DD (1) | DD202562A5 (ko) |
DE (1) | DE3261497D1 (ko) |
DK (1) | DK151017C (ko) |
ES (2) | ES509871A0 (ko) |
FI (1) | FI71558C (ko) |
GB (1) | GB2093455B (ko) |
GR (1) | GR74778B (ko) |
HU (1) | HU187652B (ko) |
IE (1) | IE52562B1 (ko) |
IL (1) | IL65097A0 (ko) |
NO (1) | NO157296C (ko) |
NZ (1) | NZ199822A (ko) |
PH (1) | PH17889A (ko) |
PL (1) | PL135472B1 (ko) |
PT (1) | PT74481B (ko) |
SU (1) | SU1088665A3 (ko) |
UA (1) | UA7228A1 (ko) |
YU (1) | YU42758B (ko) |
ZA (1) | ZA821196B (ko) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4548939A (en) * | 1984-10-01 | 1985-10-22 | Janssen Pharmaceutica N. V. | 1H-Indol-3-yl containing 1,3-dimethyl-1H-purine-2,6-diones |
IE58370B1 (en) * | 1985-04-10 | 1993-09-08 | Lundbeck & Co As H | Indole derivatives |
US4742057A (en) * | 1985-12-05 | 1988-05-03 | Fujisawa Pharmaceutical Co., Ltd. | Antiallergic thiazole compounds |
FR2613222B1 (fr) * | 1987-04-03 | 1991-06-14 | Guigon Nadine | Composition pour les soins locaux de l'epiderme, notamment du cuir chevelu |
DK733788A (da) * | 1988-01-14 | 1989-07-15 | Fujisawa Pharmaceutical Co | Indolylpiperidinderivater og fremgangsmaade til fremstilling deraf |
GB8908085D0 (en) * | 1989-04-11 | 1989-05-24 | Lundbeck & Co As H | New therapeutic use |
US5238945A (en) * | 1989-04-11 | 1993-08-24 | H. Lundbeck A/S | Method of treating psychoses |
FR2658823B1 (fr) * | 1990-02-27 | 1992-04-30 | Adir | Nouveaux derives d'aminomethylpiperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent . |
TW203049B (ko) * | 1990-04-13 | 1993-04-01 | Yamanouchi Pharma Co Ltd | |
DE4414113A1 (de) * | 1994-04-22 | 1995-10-26 | Merck Patent Gmbh | 3-Indolylpiperidine |
US5965582A (en) * | 1994-08-03 | 1999-10-12 | Asta Medica Aktiengesellschaft | N-benzylindole and benzopyrazole derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunemodulating effect |
US5521196A (en) * | 1994-10-05 | 1996-05-28 | Eli Lilly And Company | 5-HT1F agonists for the treatment of migraine |
US5521197A (en) * | 1994-12-01 | 1996-05-28 | Eli Lilly And Company | 3-<1-alkylenearyl>-4-<1,2,3,6-tetrahydropyridinyl>-and 3-<1-alkylenearyl>-4-piperidinyl-1h-indoles: new 5-HT1F agonists |
KR19980703048A (ko) * | 1995-03-20 | 1998-09-05 | 피터쥐.스트링거 | 5-치환-3-(1,2,3,6-테트라히드로피리딘-4-일)- 및 3-(피페리딘-4-일)-1h-인돌: 신규한 5-ht1f 아고니스트 |
GB9825413D0 (en) | 1998-11-19 | 1999-01-13 | Lilly Co Eli | Pharmaceutical compounds |
GB9903784D0 (en) * | 1999-02-18 | 1999-04-14 | Lilly Co Eli | Pharmaceutical compounds |
AU2003297597A1 (en) * | 2002-11-26 | 2004-06-18 | Isis Pharmaceuticals, Inc. | Benzimidazoles and analogs thereof as antibacterials |
WO2006117314A2 (en) * | 2005-04-30 | 2006-11-09 | Boehringer Ingelheim International Gmbh | Novel piperidin- substituted indoles and their use as ccr-3 modulators |
WO2007050381A2 (en) * | 2005-10-24 | 2007-05-03 | Janssen Pharmaceutica, N.V. | 3-piperidin-4-yl-indole orl-1 receptor modulators |
US8462477B2 (en) | 2010-09-13 | 2013-06-11 | Analog Devices, Inc. | Junction field effect transistor for voltage protection |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE794333A (fr) * | 1972-01-20 | 1973-07-19 | Wyeth John & Brother Ltd | Composes heterocycliques azotes therapeutiques |
US3954764A (en) * | 1973-03-30 | 1976-05-04 | Hoffmann-La Roche Inc. | Dibenzo [b,f]thiepins bearing piperazinyl substitution |
DE2322470A1 (de) * | 1973-05-04 | 1974-11-21 | Boehringer Sohn Ingelheim | Neue indolyl-piperidino-(bzw. 1,2,5,6tetrahydro-pyridyl-)butyrophenone und verfahren zu ihrer herstellung |
ZA76475B (en) * | 1975-03-10 | 1977-08-31 | Ciba Geigy Ag | Indolyalkylpiperidines |
US4147786A (en) * | 1976-02-02 | 1979-04-03 | Ciba-Geigy Corporation | 1-Indolylalkyl-3-or 4-trimethyleneurido-piperidines |
FR2469411A1 (fr) * | 1979-11-15 | 1981-05-22 | Science Union & Cie | Nouveaux derives de la piperidylbenzimidazolinone, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
US4254127A (en) * | 1980-04-03 | 1981-03-03 | Janssen Pharmaceutica, N.V. | 1,3-Dihydro-1-[(1-piperidinyl)alkyl]-2H-benzimidazol-2-one derivatives |
-
1981
- 1981-02-25 US US06/237,966 patent/US4359468A/en not_active Expired - Lifetime
-
1982
- 1982-02-19 PH PH26888A patent/PH17889A/en unknown
- 1982-02-20 AT AT82101315T patent/ATE10742T1/de not_active IP Right Cessation
- 1982-02-20 DE DE8282101315T patent/DE3261497D1/de not_active Expired
- 1982-02-20 EP EP82101315A patent/EP0058975B1/de not_active Expired
- 1982-02-22 GR GR67368A patent/GR74778B/el unknown
- 1982-02-22 DD DD82237583A patent/DD202562A5/de not_active IP Right Cessation
- 1982-02-23 PL PL1982235187A patent/PL135472B1/pl unknown
- 1982-02-23 CS CS821228A patent/CS227343B2/cs unknown
- 1982-02-23 FI FI820594A patent/FI71558C/fi not_active IP Right Cessation
- 1982-02-24 ES ES509871A patent/ES509871A0/es active Granted
- 1982-02-24 JP JP57028704A patent/JPS57156484A/ja active Granted
- 1982-02-24 UA UA3396888A patent/UA7228A1/uk unknown
- 1982-02-24 PT PT74481A patent/PT74481B/pt not_active IP Right Cessation
- 1982-02-24 YU YU410/82A patent/YU42758B/xx unknown
- 1982-02-24 NZ NZ199822A patent/NZ199822A/en unknown
- 1982-02-24 ZA ZA821196A patent/ZA821196B/xx unknown
- 1982-02-24 AR AR288538A patent/AR228475A1/es active
- 1982-02-24 GB GB8205386A patent/GB2093455B/en not_active Expired
- 1982-02-24 NO NO820583A patent/NO157296C/no unknown
- 1982-02-24 SU SU823396888A patent/SU1088665A3/ru active
- 1982-02-24 CA CA000396960A patent/CA1191137A/en not_active Expired
- 1982-02-24 IL IL65097A patent/IL65097A0/xx not_active IP Right Cessation
- 1982-02-24 HU HU82566A patent/HU187652B/hu not_active IP Right Cessation
- 1982-02-24 DK DK079882A patent/DK151017C/da not_active IP Right Cessation
- 1982-02-24 IE IE401/82A patent/IE52562B1/en not_active IP Right Cessation
- 1982-02-25 KR KR8200868A patent/KR890000008B1/ko active
- 1982-02-25 AU AU80783/82A patent/AU543948B2/en not_active Ceased
- 1982-12-07 ES ES517988A patent/ES517988A0/es active Granted
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