KR850001902A - 피페리딘 유도체의 제법 - Google Patents
피페리딘 유도체의 제법 Download PDFInfo
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- KR850001902A KR850001902A KR1019840004629A KR840004629A KR850001902A KR 850001902 A KR850001902 A KR 850001902A KR 1019840004629 A KR1019840004629 A KR 1019840004629A KR 840004629 A KR840004629 A KR 840004629A KR 850001902 A KR850001902 A KR 850001902A
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- hydrogen
- carboxy
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- 150000003053 piperidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 8
- -1 N-substituted-4-hydroxypiperidine Chemical class 0.000 claims 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 125000005843 halogen group 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- GJUMZNFPQSOVCL-UHFFFAOYSA-N 1-phenylmethoxypiperidine Chemical compound C=1C=CC=CC=1CON1CCCCC1 GJUMZNFPQSOVCL-UHFFFAOYSA-N 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- MJJALKDDGIKVBE-UHFFFAOYSA-N ebastine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)CCCN1CCC(OC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 MJJALKDDGIKVBE-UHFFFAOYSA-N 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/02—Suppositories; Bougies; Bases therefor; Ovules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- 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
-
- 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
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biophysics (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- (a) 하기 구조식(Ⅳ)의 할라이드를 하기 구조식(Ⅴ)의 N－치환－4－하이드록시피페리딘과 반응시키거나 (b) 하기구조식(Ⅷ)의 페닐메톡시피페리딘을 하기구조식(Ⅶ)의 할라이드와 반응시킨다음, R6가 COOH인 구조식(Ⅰ)의 화합물을 원할경우 우선 상기(a) 또는 (b)에 의해 R6가 알콕시카보닐기인 구조식(Ⅰ)의 화합물을 제조한 다음 알콕시카보닐기를 가수분해시켜 하기구조식(Ⅰ)의 화합물을 제조하는 것을 특징으로 하는 피페리딘 화합물의 제조방법.상기식들에서, R1은 티에닐기 또는 할로겐원자(바람직하게는 불소, 염소), 저급알콕시 또는 저급알킬기에 의해 임의로 치환된 페닐기를 나타내며 R2는 수소 또는 할로겐(바람직하게는 불소)원자나 저급 알콕시 또는 저급 알킬기를 나타내며, R2는 수소 또는 할로겐(바람직하게는 불소)원자나 저급알킬티오, 저급알콕시, 또는 저급알킬이나 C5또는 C6사이클로알킬기 또는 하기 일반구조(Ⅱ)의 기를 나타내며(여기서 R4와 R5는 각기 수소원자 또는 저급알킬기를 나타내며 R6는 사이클로알킬, 하이드록시메틸, 카복시 또는 저급알콕시카보닐기를 나타낸다) W는 카보닐(즉), 하이드록시메틸렌(즉 －CH(OH)－)기를 나타내며, X는 Cl 또는 Br이며, R3는 수소 또는 할로겐원자나 저급알킬티오, 저급알콕시 또는 저급알킬기 또는 C5또는 C6사이클로알킬기이거나 또는 R4와 R5가 상기한 바와 같으며 R6가 사이클로알킬 또는 저급알콕시카보닐기를 나타내는 상기 일반구조(Ⅱ)의 기를 나타낸다.
- 하기구조식(ⅩⅣ)인 화합물의 카복시 또는 알콕시카보닐기를 환원시킨다음 보호케탈기를 산 가수분해에 의해 제거하는 것으로 구성된 하기구조식(Ⅰ)의 화합물의 제조방법.상기 구조식들에서, R1과R2,는 상기한 바와 같으며, W는 카보닐기이며,R3는 R4와 R5가 상기한 바와 같으며 R6가 하이드록시메틸인 구조(Ⅱ)의 기이며; R8는 수소 또는 알킬기이다.
- 하기구조식(ⅩⅦ)의 화합물에서 케탈기를 산가수분해하여 제거하는 것으로 구성된 하기구조식(Ⅰ)의 화합물의 제조방법.상기식들에서, R1,R2는 상기 정의한 바와 같으며, W는 카보닐기이며, R3″는 수소, 또는 할로겐, 저급알킬티오, 저급알콕시, 저급알킬기 또는 C5또는 C6사이클로알킬기이다.
- 하기 구조식(ⅩⅧ)인 화합물의 카복시 또는 알콕시카보닐기를 환원시키거나 하기구조식(ⅩⅨ)인 화합물의 카보닐기와 카복시 또는 알콕시카보닐기를 환원시키는 것으로 구성된 하기구조식(Ⅰ)의 화합물의 제조방법.상기식들에서 R1,R2는 상기 정의한 바와 같으며 W는 하이드록시메틸렌기이며, R3는 R4와 R5와 상기한 바와 같으며 R6가 하이드록시메틸기인 상기구조식(Ⅱ)의 기이며; R8은 H 또는 알킬이다.
- 제1항 내지4항중 어느 하나에서 R2이페닐, 플루오로페닐, 메틸페닐, 메톡시페닐 또는 티에닐기인 방법.
- 제1항 내지 5항중 어느 하나에서 R2가 H,F Cl, CH3또는 CH3O인 방법.
- 제1항 내지 6항중 어느 하나에서 R3가 H,F, Br, 에틸, 이소프로필, t－부틸, 메톡시 또는 사이클로헥실인 방법.
- 제1항 내지 7항중 어느 하나에서 R3가이며 여기서 R4와 R5가 H 또는 메틸이고 R6가 사이클로프로필, 에톡시카보닐, 카복시 또는 하이드록시메틸인 방법.
- 제1항 내지 4항중 어느 하나에서 4－디페닐메톡시－α－(4－t－부틸페닐)－1－피페리딘부탄올, 4－디－(4－플루오로페닐) 메톡시－1－[3－(4－t－부틸벤조일)프로필]－피페리딘, 4－α－[2－티에닐)－벤질옥시]－1－[3－(4－t－부틸벤조일)프로필]－피페리딘, 4－디페닐－메톡시－α－(4－사이클로헥실페닐)－1－피페리딘부탄올 또는 4－디페닐－메톡시－1－[3－(4－이소프로필 벤조일)－프로필]－피페리딘 및 그의 산부가염을 제조하는 방법.
- 제1항 내지 4항중 어느 한항에서 4－디페닐메톡시－1－[3－(4－t－부틸벤조일)프로필]－피페리딘과 그의 산부가염을 제조하는 방법.
- 제1항 내지 10항중 어느 하나에서 화합물을 제약상 허용되는 산과 반응시켜 염으로 전환시키는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838321157A GB8321157D0 (en) | 1983-08-05 | 1983-08-05 | Piperidine derivatives |
| GB8321157 | 1983-08-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850001902A true KR850001902A (ko) | 1985-04-10 |
| KR910009937B1 KR910009937B1 (ko) | 1991-12-06 |
Family
ID=10546879
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840004629A KR910009937B1 (ko) | 1983-08-05 | 1984-08-03 | 피페리딘 유도체 및 그의 제법 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4550116A (ko) |
| EP (1) | EP0134124B1 (ko) |
| JP (1) | JPS6094962A (ko) |
| KR (1) | KR910009937B1 (ko) |
| AT (1) | ATE30418T1 (ko) |
| AU (1) | AU565293B2 (ko) |
| CA (1) | CA1264324A (ko) |
| DE (2) | DE3466982D1 (ko) |
| DK (1) | DK158348C (ko) |
| EG (1) | EG16936A (ko) |
| ES (5) | ES8505979A1 (ko) |
| FI (1) | FI81567C (ko) |
| GB (1) | GB8321157D0 (ko) |
| GR (1) | GR80031B (ko) |
| HU (1) | HU196370B (ko) |
| IL (1) | IL72465A (ko) |
| MX (2) | MX156547A (ko) |
| MY (1) | MY101017A (ko) |
| NZ (1) | NZ209023A (ko) |
| PH (1) | PH19880A (ko) |
| PT (1) | PT79028B (ko) |
| ZA (1) | ZA845968B (ko) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4673684A (en) * | 1984-04-04 | 1987-06-16 | Terumo Corporation | Amide derivatives and 5-lipoxygenase inhibitors containing the same as an active ingredient |
| JPS625956A (ja) * | 1985-07-02 | 1987-01-12 | Terumo Corp | ビニル誘導体およびこれを含有する５−リポキシゲナ−ゼ作用阻害剤 |
| US4766215A (en) * | 1987-02-27 | 1988-08-23 | American Home Products Corporation | Histamine H1 -receptor antagonists |
| US4929618A (en) * | 1988-03-25 | 1990-05-29 | Ube Industries, Ltd. | Piperdine and piperazine derivatives, and antihistaminic pharmaceutical compositions containing the same |
| US5231104A (en) * | 1988-07-08 | 1993-07-27 | Pfizer Inc. | 1-arylethyl-3-substituted piperidines |
| CA2015949A1 (en) * | 1989-05-22 | 1990-11-22 | Yasuo Ito | Piperidine derivative, method for preparation thereof, and a pharmaceutical composition comprising the same |
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1983
- 1983-08-05 GB GB838321157A patent/GB8321157D0/en active Pending
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1984
- 1984-07-19 ES ES534435A patent/ES8505979A1/es not_active Expired
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- 1984-07-19 ES ES534438A patent/ES534438A0/es active Granted
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- 1984-07-20 IL IL72465A patent/IL72465A/xx not_active IP Right Cessation
- 1984-07-24 US US06/633,958 patent/US4550116A/en not_active Expired - Lifetime
- 1984-07-26 NZ NZ209023A patent/NZ209023A/en unknown
- 1984-08-01 ZA ZA845968A patent/ZA845968B/xx unknown
- 1984-08-01 PH PH31053A patent/PH19880A/en unknown
- 1984-08-01 EG EG49184A patent/EG16936A/xx active
- 1984-08-02 DE DE8484305268T patent/DE3466982D1/de not_active Expired
- 1984-08-02 DE DE1998175026 patent/DE19875026I2/de active Active
- 1984-08-02 EP EP84305268A patent/EP0134124B1/en not_active Expired
- 1984-08-02 FI FI843053A patent/FI81567C/fi not_active IP Right Cessation
- 1984-08-02 AT AT84305268T patent/ATE30418T1/de active
- 1984-08-02 CA CA000460237A patent/CA1264324A/en not_active Expired - Lifetime
- 1984-08-03 PT PT79028A patent/PT79028B/pt unknown
- 1984-08-03 MX MX202251A patent/MX156547A/es unknown
- 1984-08-03 HU HU842961A patent/HU196370B/hu unknown
- 1984-08-03 KR KR1019840004629A patent/KR910009937B1/ko not_active IP Right Cessation
- 1984-08-03 DK DK378784A patent/DK158348C/da not_active IP Right Cessation
- 1984-08-03 JP JP59164170A patent/JPS6094962A/ja active Granted
- 1984-08-03 AU AU31465/84A patent/AU565293B2/en not_active Expired
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1992
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