KR830007550A - 시클릭아민의 제조방법 - Google Patents
시클릭아민의 제조방법 Download PDFInfo
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- KR830007550A KR830007550A KR1019810004985A KR810004985A KR830007550A KR 830007550 A KR830007550 A KR 830007550A KR 1019810004985 A KR1019810004985 A KR 1019810004985A KR 810004985 A KR810004985 A KR 810004985A KR 830007550 A KR830007550 A KR 830007550A
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- Prior art keywords
- compound
- hydroxy
- alkyl
- aryl
- alkoxy
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- -1 cyclic amine Chemical class 0.000 title claims 20
- 238000000034 method Methods 0.000 title claims 13
- 125000004423 acyloxy group Chemical group 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
- 125000005518 carboxamido group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052727 yttrium Inorganic materials 0.000 claims 1
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- 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
-
- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/32—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to acyclic carbon atoms and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- 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
- C07D207/20—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—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
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Luminescent Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Cephalosporin Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 상용하는 데하이드로 피롤리딘 화합물의 에틸렌성 이중결합을 환원시키고, R이 수소인 화합물에서는 수소를 수소가 R이 아닌 다른 기타의 치환체로 임의로 치환시킴을 특징으로 하여 하기 일반식(Ⅰ) 및 (Ⅱ)를 제조하는 방법.상기식에서Z와 Y는 각각 주요체인에 탄소원자 1내지 5를 함유한 알킬렌이거나 OH, 알카노일옥시, 알콕시, 멜캅토 또는 알킵멜캅토로 치환된 전기의 알킬렌이며,R1,R2및 R3각각은 독립적으로 H, 알킬, 아릴, 할로, 알콕시, 알케닐옥시, 알킬설피닐, 알킬설포닐, 알킬멜캅토, 시아노, 카복시, 카브알콕시, 카복스아미도, 설파모일, 트리플루오로메틸, 히드록시, 히드록시알킬, 아실옥시, 알킬아미노, 설포닐아미노, 또는 아실아미노이며, R1과 R2함께 취하여 메틸렌 디옥시 또는 -O-CO-O-를 형성하며,Ar은 헤테로아릴, 시클로 알킬 또는 하기의 일반식이며,(상기식에서 R1,R2,R3는 전술한 바와 같다)R은 H, 알킬 시클로알킬, 아릴, 아르알킬 (aralkyl), 알케닐, 알키닐, 카보알콕시, 또는 CONR4R5이며, R4와 R5각각은 H 또는 알킬이며, 각 하이드로카빌기에서 탄소원자의 총수는 10까지이다.
- 제1항에 있어서, 환원을 촉매 수소화 반응에 의해 실행하는 방법.
- 제2항에 있어서, 수소화 반응을 귀금속 촉매상에서 실시하는 방법.
- 제3항에 있어서, 촉매가 팔라듐 또는 백금 수소화 반응촉매인 방법.
- 제1항 내지 제4항중의 어느하나에 있어서, 환원 생성물이 하기 일반식(Ⅲ)과 (Ⅳ)의 화합물인 방법.상기식에서R1및 R2각각은 독립적으로 H, 알킬, 아릴, 할로 알콕시, 알케닐옥시, 알킬설피닐, 알킬설포닐, 알킬멜캅토, 시아노, 카복시, 카브알콕시, 카복스아미도, 설파모일, 트리플루오로메틸, 히드록시, 히드록시알킬, 아실옥시, 알킬아미노, 설포닐아미노 또는 아실아미노이며, R1과 R2함께 취하여 메틸렌디옥시 또는 -0-CO-O-를 형성하며R6는 H, 알킬, 아릴, 할로, 알콕시, 알케닐옥시, 알킬설포닐, 알킬멜캅토, 시아노, 카복시, 카브알콕시, 카복스아미도, 설파모일, 트리플루오로메틸, 히드록시, 히드록시알킬, 아실옥시, 알킬아미노, 설포닐아미노 또는 아실아미노이며,각 하이드로 카빌기에서 탄소원자의 총수는 10까지이다.
- 제1항내지 제4항중의 어느 하나에 있어서, 환원 생성물이 하기 일반식의 화합물인 방법.상기식에서 R1,R2및 R6는 독립적으로 히드록시 또는 알카노일옥시이고, 알카노일옥시의 알킬부분은 탄소원자 6까지 함유한다.
- 제1항내지 제4항중의 어느하나에 있어서, 환원 생성물이 하기 일반식의 화합물이 방법.상기식에서 R1,R2,R3,Z,Y 및 Ar은 전술한바와 같다.
- 제1항내지 항4중의 어느 하나에 있어서, 환원 생성물이 하기 일반식의 화합물인 방법.상기식에서 R1과 R2각각은 독립적으로 H, 알킬, 아릴, 할로, 알콕시, 알케닐옥시, 알킬설피닐, 알킬설포닐, 알킬멜캅토, 시아노, 카복시, 카브알콕시, 카복스아미도, 설파모일, 트리플루오로메틸, 히드록시, 히드록시알킬, 아실옥시, 알킬아미노, 설포닐아미노 또는 아실아미노이며, R1과 R2함께 취하여 메틸렌디옥시 또는 -O-CO-O-를 형성하며R6는 H, 알킬, 아릴, 할로, 알콕시, 알케닐옥시, 알킬설포닐, 알킬멜캅토, 시아노, 카복시,카브알콕시, 카복스아미도, 설파모일, 트리플루오로메틸, 히드록시, 히드록시알킬, 아실옥시, 알킬아미노, 설포닐아미노 또는 아실아미노이며,각 하이드로카빌기에서 탄소원자의 총수는 10까지이고, 지방족기는 탄소원자수 7까지이며 방향족기는 탄소수 10까지 함유한다.
- 제1항내지 제4항중의 어느 하나에 있어서, 환원생성물이 하기 구조식의 화합물인 방법.
- 제1항내지 제4항중의 어느 하나에 있어서, 환원생성물이 하기 구조식의 화합물인 방법.
- 제1항내지 제4항중의 어느 하나에 있어서, 환원생성물이 R1,R2, 및 R3가 각각 히드록시인 제6항에 따르는 화합물인 방법.
- 제1항내지 제4항중의 어느 하나에 있어서, 환원생성물이 R1,R2및 R3가 각각 알카노일옥시인 제6항에 따르는 화합물인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/198,671 US4342692A (en) | 1980-10-20 | 1980-10-20 | Pyrrolidines |
| US198,671 | 1981-10-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR830007550A true KR830007550A (ko) | 1983-10-21 |
Family
ID=22734311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810004985A KR830007550A (ko) | 1980-10-20 | 1981-12-18 | 시클릭아민의 제조방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4342692A (ko) |
| EP (1) | EP0050370B1 (ko) |
| JP (1) | JPS57112370A (ko) |
| KR (1) | KR830007550A (ko) |
| AT (1) | ATE15187T1 (ko) |
| AU (1) | AU552043B2 (ko) |
| CA (1) | CA1206476A (ko) |
| DE (1) | DE3172050D1 (ko) |
| DK (1) | DK461881A (ko) |
| ES (1) | ES507003A0 (ko) |
| IL (1) | IL64107A0 (ko) |
| ZA (1) | ZA817250B (ko) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK328382A (da) * | 1981-07-22 | 1983-01-23 | Syntex Inc | Fremgangsmaade til fremstilling af antihypertensive midler |
| IE840151L (en) * | 1983-01-24 | 1985-02-28 | Syntex Inc | £(3, 4-methylenedioxy-ó-hydroxybenzyl| pyrrolidine¹antihypertensives |
| US4548949A (en) * | 1983-01-24 | 1985-10-22 | Syntex (U.S.A.) Inc. | +2-[(3,4-Methylenedioxy)phenethyl]-5-[(3-carboxamido-4-hydroxy)-α-hydroxybenzyl]pyrrolidines |
| AU2370084A (en) * | 1983-01-24 | 1984-07-26 | Syntex (U.S.A.) Inc. | Pyrrolidine derivatives |
| US4701461A (en) * | 1983-03-21 | 1987-10-20 | Usv Pharmaceutical Corporation | Substituted cyclic amines |
| US4569941A (en) * | 1983-03-21 | 1986-02-11 | Usv Pharmaceutical Corp. | Method of using phenyl-alkylene-2-pyridyl derivatives to increase cardiac contractility in a mammal |
| US4548951A (en) * | 1983-04-21 | 1985-10-22 | Syntex (U.S.A.) Inc. | Hypotensive benzoxathiole pyrrolidines |
| US4558066A (en) * | 1984-05-17 | 1985-12-10 | Syntex (U.S.A.) Inc. | Treatment and prevention of ocular hypertension |
| US4632929A (en) * | 1985-01-17 | 1986-12-30 | Usv Pharmaceutical Corp. | Method of hypertensive treatment using phenyl-alkylene-2-pyridyl derivatives |
| US4826869A (en) * | 1988-02-19 | 1989-05-02 | Syntex (U.S.A.) Inc. | N-(lower alkyl)-2-(3'ureidobenzyl)pyrrolidines |
| EP0496884B1 (en) * | 1989-10-17 | 1997-01-08 | Nippon Soda Co., Ltd. | Pyrrole monomer, process for preparing the same, and functional polymer film |
| US5093355A (en) * | 1989-10-30 | 1992-03-03 | Syntex (U.S.A.) Inc. | Benzylpyrrolidine derivatives as dopamine agonists |
| JPH04294003A (ja) * | 1991-03-22 | 1992-10-19 | Inax Corp | ユニットルームの模様付け方法 |
| US6015824A (en) * | 1998-02-10 | 2000-01-18 | Hoffmann-La Roche Ag | Pyrrolidine and piperidine derivatives and treatment of neurodegenerative disorders |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3655693A (en) * | 1969-06-25 | 1972-04-11 | Merck & Co Inc | Anti-inflammatory salicyclic acid derivatives |
| US3910934A (en) * | 1970-05-21 | 1975-10-07 | Minnesota Mining & Mfg | Process for the preparation of {60 -(hydroxy and alkoxy substituted)phenyl-{60 -(2-piperidinyl)-methanols |
| US3941796A (en) * | 1970-05-21 | 1976-03-02 | Minnesota Mining And Manufacturing Company | α-(Hydroxy and alkoxy substituted)phenyl-α-(2-piperidinyl)-methanols |
| ZA732136B (en) * | 1972-04-12 | 1974-03-27 | Lilly Co Eli | Dopamine derivatives |
| FR2460929A1 (fr) * | 1979-07-06 | 1981-01-30 | Roussel Uclaf | Nouveaux derives de l'a-phenyl 2-pyrrolidinemethanol et leur sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
-
1980
- 1980-10-20 US US06/198,671 patent/US4342692A/en not_active Expired - Lifetime
-
1981
- 1981-10-16 CA CA000388095A patent/CA1206476A/en not_active Expired
- 1981-10-19 DK DK461881A patent/DK461881A/da not_active Application Discontinuation
- 1981-10-20 ES ES507003A patent/ES507003A0/es active Granted
- 1981-10-20 JP JP56166516A patent/JPS57112370A/ja active Granted
- 1981-10-20 AU AU76617/81A patent/AU552043B2/en not_active Ceased
- 1981-10-20 AT AT81108589T patent/ATE15187T1/de not_active IP Right Cessation
- 1981-10-20 ZA ZA817250A patent/ZA817250B/xx unknown
- 1981-10-20 DE DE8181108589T patent/DE3172050D1/de not_active Expired
- 1981-10-20 EP EP81108589A patent/EP0050370B1/en not_active Expired
- 1981-10-23 IL IL64107A patent/IL64107A0/xx unknown
- 1981-12-18 KR KR1019810004985A patent/KR830007550A/ko unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL64107A0 (en) | 1982-01-31 |
| ZA817250B (en) | 1982-09-29 |
| JPH0250901B2 (ko) | 1990-11-05 |
| DE3172050D1 (en) | 1985-10-03 |
| JPS57112370A (en) | 1982-07-13 |
| ES8205769A1 (es) | 1982-08-16 |
| ES507003A0 (es) | 1982-08-16 |
| US4342692A (en) | 1982-08-03 |
| EP0050370A1 (en) | 1982-04-28 |
| DK461881A (da) | 1982-04-21 |
| AU552043B2 (en) | 1986-05-22 |
| AU7661781A (en) | 1982-04-29 |
| EP0050370B1 (en) | 1985-08-28 |
| CA1206476A (en) | 1986-06-24 |
| ATE15187T1 (de) | 1985-09-15 |
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