KR850002981A - 5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조방법 - Google Patents

5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조방법 Download PDF

Info

Publication number
KR850002981A
KR850002981A KR1019840006212A KR840006212A KR850002981A KR 850002981 A KR850002981 A KR 850002981A KR 1019840006212 A KR1019840006212 A KR 1019840006212A KR 840006212 A KR840006212 A KR 840006212A KR 850002981 A KR850002981 A KR 850002981A
Authority
KR
South Korea
Prior art keywords
formula
general formula
following general
lower alkyl
compound
Prior art date
Application number
KR1019840006212A
Other languages
English (en)
Other versions
KR870001509B1 (ko
Inventor
쟈안센 프란스 (외 3)
Original Assignee
폴 아드리안 쟌 쟈안센
쟈안센 파아마슈우티카 엔. 부이.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 폴 아드리안 쟌 쟈안센, 쟈안센 파아마슈우티카 엔. 부이. filed Critical 폴 아드리안 쟌 쟈안센
Publication of KR850002981A publication Critical patent/KR850002981A/ko
Priority to KR1019870006489A priority Critical patent/KR870001647B1/ko
Application granted granted Critical
Publication of KR870001509B1 publication Critical patent/KR870001509B1/ko

Links

Classifications

    • 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
    • C07D213/60—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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • A61P11/08—Bronchodilators
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
    • C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • 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
    • C07D213/60—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 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
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • C07D213/60—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 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • 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
    • C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07D409/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (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)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

내용 없음

Description

5원 헤테로사이클 고리를 갖는 N-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (1)

  1. 다음 일반식(Ⅲ)의 피페리딘을 반응 불활성용매 중에서 다음 일반식(Ⅱ)의 중간체와 알킬화반응 시키거나; 또는 다음 일반식(Ⅳ)의 중간체를 반응불활성 용매 중에서 적합한 알킬할라이드, 금속산화물 또는 금속염으로 탈황고리화 반응시키거나; 또는 다음 일반식(Ⅴ)의 중간체를 적합한 반응 불활성용매 중에서 다음 일반식(Ⅵ)의 피페리딘과 반응시켜 다음 일반식(Ⅰ-b-1)의 화합물을 제조하거나; 또는 다음 일반식(Ⅶ)의 중간체를 적합한 반응불활성 용매 중에서 다음 일반식(Ⅷ)의 피페리딘과 반응시켜 다음 일반식(Ⅰ-b-2)의 화합물을 제조하거나; 또는 다음 일반식(Ⅸ)의 중간체를 적합한 반응불활성 용매 중에서 다음 일반식(Ⅷ)의 OH 기능기를 적합한 이틸기로 전환시킨 후에 다음 일반식(Ⅷ)의 피페리딘과 반응시키거나, 또는 다음 일반식(Ⅸ)의 중간체와 다음 일반식(Ⅷ)의 피페리딘을 적합한 아미드 또는 에스테르 형성제와 함께 반응시켜 다음 일반식(Ⅰ-c)의 화합물을 제조하거나; 또는 다음 일반식(Ⅲ-a)의 피페리딘을 적합한 반응불활성용매 중에서 일반식(Ⅹ)의 화합물과 반응시켜 다음 일반식(Ⅰ-d)의 화합물을 제조하거나; 또는 다음 일반식(Ⅸ)의 이미드아미드 유도체를 반응불활성용매 중에서 고리화반응시켜 다음 일반식(Ⅰ-e)의 화합물을 제조하거나; 또는 다음 일반식(ⅩⅡ)의 티오아미드 유도체를 반응불활성용매 중에서 적합한 알킬할라이드, 금속산화물 또는 금속염과 탈황고리화 반응시켜 다음 일반식(Ⅰ-f)의 화합물을 제조하거나; 또는 다음 일반식(ⅩⅣ)의 시아나이드를 반응불활성 용매 중에서 다음 일반식(ⅩⅢ)의 화합물과 측합반응시켜 다음 일반식(Ⅰ-g)의 화합물을 제조하거나; 또는 다음 일반식(ⅩⅥ)의 티오아미드 유도체를 반응 불활성용매 중에서 다음 일반식(ⅩⅤ)의 화합물과 축합반응시켜 다음 일반식(Ⅰ-h)의 화합물을 제조하거나; 또는 다음 일반식(ⅩⅧ)의 케톤을 반응불활성용매 중에서 다음 일반식(ⅩⅦ)의 티오아미드 유도체와 축합반응시켜 다음 일반식(Ⅰ-i)의 화합물을 제조하거나; 또는 다음 일반식(ⅩⅧ)의 케톤을 암모니아 또는 암모늄연 존재하에 반응불활성용매 중에서 다음 일반식(ⅩⅨ)의 이소티오시아네이트와 축합반응시켜 다음 일반식(Ⅰ-j)의 화합물을 제조하거나; 또는 다음 일반식(Ⅵ-a)의 이소티오시아네이트를 반응불활성용매 중에서 다음 일반식(ⅩⅩ)의 화합물과 축합반응시켜 다음 일반식(Ⅰ-k)의 화합물을 제조하거나; 또는 다음 일반식(ⅩⅩⅠ)의 화합물을 반응불활성용매 중에서 적합한 환원제로 환원시켜 다음 일반식(Ⅰ-l)의 화합물, 이의 약제학적으로 허용되는 산부가염과 입체화학적 이성체를 제조하는 방법.
    의 기이고, A1=A2-A3=A4는 다음 임반식(a)(b)(c)(d) 또는 (e)를 갖는 2가의 레디칼로서 이들 레디칼 중의 1개 또는 2개 수소원자가 할로, 저급알킬, 저급알킬옥시, 트리폴루오로메틸 또는 하이드록시와 상호 독립적으로 치환될 수 있고; R은 수소 및 저급알킬로 구성되는 균으로 부터 선정된 것이고, R1은 수소, 알킬, 사이클로알킬, Ar1과 1개 또는 2개의 Ar1기로 치환된 저급알킬로 구성되는 군으로 부터 선정된 것이며; R2는 수소, 저급알킬, 사이클로알킬, (저급 알킬)-CO-, (저급 알킬옥시)-CO 및 Ar2저급알킬로 구성되는 군으로부터 선정된 것이고; L은 다음 일반식(f), (g) 및 (h)의 레디칼로 구성된 군으로 부터 선정된 것으로 이때 n은 0 또는 1또는 2의 정수이고, S는 0 또는 1 내지 6 포함 정수이며, Alk는 저급알칸디임이고, Y는 O, S, NR3또는 적접결합손이며, X는 O, S, CH-NO2또는 NR4이고, Z는 O, S, NR5또는 저접결합손이고, 또 Het는 1개 이상의 질소원자를 갖는 임의 치환된 5원 헤테로사이클 고리로서 임의 치환된 벤젠 고리로서 임의 축합될 수 있으며, 또 이 Het는 탄소원자상에서 CSH2S와 연결되고 전술한 R3가 수소, 저급알킬, (Ar2) 저급알킬, 2-저급알킬-옥시-1,2-디옥소에틸 또는 임반식 -C(=X)-R6의 기로서 R6는 수소, 저급알킬, Ar2, Ar2-저급알킬, 저급알킬옥시, Ar2-저급알킬옥시, 모노-또는 디(저급알킬) 아미노, Ar2-아미노, Ar2-저급알킬아미노 또는 Ar2저급알킬(저급알킬) 아미노이고, 전술한 R4는 수소, 저급알킬, 시아노, 니트로, Ar2-선포닐, 저급알킬선포닐, 저급알킬카르보닐 또는 Ar2-카르보닐이며; 또는 전술한 R5는 수소 또는 저급 알킬로서, 단 (i) A1=A2-A3=A4가 다음 일반식(a) 또는 (b)의 2가의 레디칼인 경우에는 Het가 1-(저급알킬) 피톨릴이 아니고, (ⅱ) A1=A2-A3=A4가 다음 일반식(a) 또는 (b)의 2가의 레디칼이고 또 L이 S는 O 또 Y는 NR3인 다음 일반식(g)의 레디칼인 경우 Het는 1H-벤즈이미다졸-2-일이 아니고; 또 Ar1은 할로, 하이드록시, 니트로, 시아노, 트리플루오로메틸, 저급알킬, 저급알킬옥시, 저급알킬티오, 메르캅토, 아미노, 모노-및 디(저급알킬) 아미노, 카르복실, 저급알킬옥시카르보닐과 저급알킬-CO-로 구성되는 군으로 부터 각각 독립해서 선정한 3개 까지의 치환체로 임의 치환한 페닐; 티에닐; 할로티에닐; 푸라닐; 저급알킬 치환 푸라닐; 피리디닐; 피라지닐; 저급알킬로 임의 치환된 티아졸릴 및 이미다졸릴로 구성되는 군으로 부터 선정한 것이면; 또 Ar2는 할로, 하이드록시, 니트로, 시아노, 트리플루오로메틸, 저급알킬, 저급알킬옥시, 저급알킬티오, 메르캅토, 아미노, 모노-및 디(저급알킬) 아미노, 카르복실, 저급 알킬옥시카르보닐 및 (저급알킬)-CO로 구성되는 군으로 부터 각각 독립해서 선정한 3개까지의 치환체로 임의 치환한 페닐로 구성되는 군으로 부터 선정한 것이고, 또 Q2가 수소인 경우, Q1는 Het와 결합해서 W가 할로 또는 설포닐옥시와 같은 적당한 반응이탈기를 나타내는 일반식 L-W의 기를 형성하며; Q1이 W'가 전술한 W의 정의 이외에 S가 0일때 W'가 또한 저급알킬옥시 또는 저급알킬티오기 이라는 조건하에 일반식-CSH2S-W'의 기이고 또 Q2는 일반식의 기인 경우 다음 일반식(Ⅰ-a-1)의 화합물을 제조하고; Q1이 전술한 조건의 -CSH2S-W'의 기이고 또 Q2가 Y'가 적접결합손을 제외하고는 앞의 Y의 정의와 동일한 일반식 HY'-Aik-의 기인 경우, 다음 일반식(Ⅰ-a-2)의 화합물을 제조하며; Q1이 전술한 조건의 -CSH2S-W'의 기이고 또 Q2가 Z'가 직접 결합손을 제외하고는 앞의 Z의 정의와 동일한 일반식 HZ'-C(X)-Y-Alk-인 기인 경우 다음 일반식(Ⅰ-a-3)의 화합물을 제조하고; Q1이 일반식 -CSH2S-Y'H의 기이고 또 Q2가 일반식 W-Aik-의 기인 경우 다음 일반식(Ⅰ-a-2)의 화합물을 제조하며, 또 Q1이 일반식 -CSH2S-Z-C(X)-Y'H의 기이고, 또 Q2가 일반식 W-Alk의 기인 경우 다음 일반식(Ⅰ-a-4)의 화합물을 제조하고; 또 X'는 O 또는 S이며, R7, R8및 R9는 각각 독립해서 이미다졸 고리상의 임의 치환체이고; R10및 R11은 각각 독립해서 1H-벤즈이미다졸-2-일 고리상의 임의 치환체이며, R12및 R13은 각각 독립해서 옥시졸 고리상의 임의 치환체이고, R14, R15, R16, R17및 R18은 각각 독립해서 티아졸 고리상의 임의 치환체이며, R19및 R20은 각각 독립해서 4,5-디하이드록시티아졸 고리상의 임의 치환체이고, Alk'는 1개의 메틸렌 기능기가 상실되었다는 조건으로 앞의 Alk의 정의와 동임하며, K는 다음 일반식(i)(j) 및 (k)로 표시되는 2가의 기이다.
    -CH=CH-CH=CH- (a) -N=CH-CH=CH- (b) -CH=N-CH=CH- (c)
    -CH=CH-N=CH- (d) -CH=CH-CH=N- (e)
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840006212A 1983-10-06 1984-10-06 5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조 방법 KR870001509B1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019870006489A KR870001647B1 (ko) 1983-10-06 1987-06-25 5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로 사이클 )-4-피페리딘아민의 제조방법

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US53959783A 1983-10-06 1983-10-06
US539597 1983-10-06
US625343 1984-06-27
US06/625,343 US4634704A (en) 1983-10-06 1984-06-27 Anti-allergic five membered heterocyclic ring containing N-(bicyclic heterocycyl)-4-piperidinamines

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1019870006489A Division KR870001647B1 (ko) 1983-10-06 1987-06-25 5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로 사이클 )-4-피페리딘아민의 제조방법

Publications (2)

Publication Number Publication Date
KR850002981A true KR850002981A (ko) 1985-05-28
KR870001509B1 KR870001509B1 (ko) 1987-08-20

Family

ID=27066147

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019840006212A KR870001509B1 (ko) 1983-10-06 1984-10-06 5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조 방법

Country Status (19)

Country Link
US (1) US4634704A (ko)
EP (1) EP0145037B1 (ko)
JP (1) JPH0798818B2 (ko)
KR (1) KR870001509B1 (ko)
AU (1) AU565884B2 (ko)
BG (1) BG43007A3 (ko)
CA (1) CA1247614A (ko)
DE (1) DE3476204D1 (ko)
DK (1) DK163239C (ko)
ES (1) ES536590A0 (ko)
FI (1) FI81797C (ko)
HU (1) HU207514B (ko)
IL (1) IL73118A (ko)
NO (1) NO160441C (ko)
NZ (1) NZ209642A (ko)
PH (1) PH21310A (ko)
PT (1) PT79307B (ko)
RO (1) RO90457A (ko)
ZW (1) ZW16484A1 (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100280281B1 (ko) * 1993-05-19 2001-03-02 죠지폴릭 신발용 신발레이싱장치

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0144101B1 (en) * 1983-11-30 1991-02-06 Janssen Pharmaceutica N.V. Bicyclic heterocyclyl containing n-(bicyclic heterocyclyl)-4-piperidinamines
US4588722A (en) * 1984-01-09 1986-05-13 Janssen Pharmaceutica N.V. N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives
PH23995A (en) * 1984-01-09 1990-02-09 Janssen Pharmaceutica Nv 4((bicycle heterocyclyl)-methyl and hetero)piperidines
CA1260474A (en) * 1984-12-03 1989-09-26 Raymond A. Stokbroekx Benzoxazol- and benzothiazolamine derivatives
GB8515934D0 (en) * 1985-06-24 1985-07-24 Janssen Pharmaceutica Nv (4-piperidinomethyl and-hetero)purines
US5258380A (en) * 1985-06-24 1993-11-02 Janssen Pharmaceutica N.V. (4-piperidinylmethyl and -hetero)purines
CA1327579C (en) * 1986-02-03 1994-03-08 Frans Eduard Janssens Anti-histaminic compositions containing n-heterocyclyl-4-piperidinamines
JPH0784462B2 (ja) * 1986-07-25 1995-09-13 日清製粉株式会社 ベンゾイミダゾ−ル誘導体
NZ223654A (en) * 1987-03-09 1990-03-27 Janssen Pharmaceutica Nv 1-alkyl-substituted-benzimidazole-4-piperidinamines and pharmaceutical compositions
US4943580A (en) * 1987-03-09 1990-07-24 Janssen Pharmaceutica N.V. Anti-histaminic benzimidazole, imidazopyridine and purine derivatives
US5039677A (en) * 1987-06-01 1991-08-13 Janssen Pharmaceutica N.V. 6-(1H-azol-1-ylmethyl)-1-(pyrimidinyloxy)-1H benzotriazoles
US4897401A (en) * 1987-06-19 1990-01-30 Janssen Pharmaceutical N.V. N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives useful in treating allergic diseases
US5006527A (en) * 1987-06-19 1991-04-09 Janssen Pharmaceutica N.V. Pharmacologically active N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives
US4880811A (en) * 1987-06-24 1989-11-14 Memorial Hospital For Cancer And Allied Diseases Use of C-5 mono-substituted barbiturates to treat disorders of uric acid metabolism
US5151424A (en) * 1987-07-01 1992-09-29 Janssen Pharmaceutica N.V. Pharmacologically active (Bicyclic heterocyclyl)methyl and -hetero) substituted hexahydro-1H-azepines and pyrrolidines
NZ225152A (en) * 1987-07-17 1990-04-26 Janssen Pharmaceutica Nv Heterocyclically substituted piperidinyl benzamides as pharmaceuticals
US5130312A (en) * 1987-07-17 1992-07-14 Janssen Pharmaceutica N.V. Substituted N-(3-hydroxy-4-piperidinyl)benzamides
FR2618435B1 (fr) * 1987-07-23 1989-10-27 Synthelabo Derives de benzimidazole, leur preparation et leur application en therapeutique
CA1317940C (en) * 1987-09-25 1993-05-18 Georges H. P. Van Daele Substituted n-(1-alkyl-3-hydroxy-4-piperidinyl)benzamides
US5041454A (en) * 1987-09-25 1991-08-20 Janssen Pharmaceutica N.V. Novel substituted N-(1-alkyl-3-hydroxy-4-piperidinyl)benzamides
US4975439A (en) * 1987-09-25 1990-12-04 Janssen Pharmaceutical N.V. Novel substituted N-(1-alkyl-3-hydroxy-4-piperidinyl)benzamides
GB8900380D0 (en) * 1989-01-09 1989-03-08 Janssen Pharmaceutica Nv 2-aminopyrimidinone derivatives
PH30434A (en) * 1989-04-07 1997-05-09 Janssen Pharmaceutica Nv Hydroxyalkylfuranyl derivatives
NZ238863A (en) * 1990-07-19 1993-03-26 Janssen Pharmaceutica Nv Substituted thiazolyl and pyridinyl derivatives
KR100190299B1 (ko) * 1990-07-19 1999-06-01 디르크 반테 신규한 옥사졸릴 유도체
US5217980A (en) * 1990-07-19 1993-06-08 Janssen Pharmaceutica N.V. Oxazolyl and piperidinyl substituted benimidazolyl compounds
FR2674855B1 (fr) * 1991-04-03 1994-01-14 Synthelabo Derives de piperidine, leur preparation et leur application en therapeutique.
ES2038532B1 (es) * 1991-05-10 1994-02-16 Espanola Prod Quimicos Procedimiento de preparacion de nuevos derivados de 2-piperacinilbecimidazol.
US6211199B1 (en) 1995-11-17 2001-04-03 Aventis Pharmaceuticals Inc. Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases
US6194406B1 (en) 1995-12-20 2001-02-27 Aventis Pharmaceuticals Inc. Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease
US6423704B2 (en) 1995-12-20 2002-07-23 Aventis Pharmaceuticals Inc. Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases
US5998439A (en) * 1996-02-21 1999-12-07 Hoescht Marion Roussel, Inc. Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases
US5932571A (en) * 1996-02-21 1999-08-03 Hoechst Marion Roussel, Inc. Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases
US5922737A (en) * 1996-02-21 1999-07-13 Hoechst Marion Roussel, Inc. Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases
US5817823A (en) * 1997-04-17 1998-10-06 Sepracor Inc. Method for synthesizing 2-substituted imidazoles
OA11978A (en) * 1999-06-28 2006-04-18 Janssen Pharmaceutica Nv Respiratory syncytial virus replication inhibitors.
PT1196409E (pt) 1999-06-28 2004-06-30 Janssen Pharmaceutica Nv Inibidores da replicacao do virus sincicial respiratorio
EP1196410B1 (en) * 1999-06-28 2004-02-18 Janssen Pharmaceutica N.V. Respiratory syncytial virus replication inhibitors
AR033517A1 (es) 2000-04-08 2003-12-26 Astrazeneca Ab Derivados de piperidina, proceso para su preparacion y uso de estos derivados en la fabricacion de medicamentos
DK1404667T3 (da) 2001-07-02 2006-07-10 Astrazeneca Ab Piperidinderivater, der er anvendelige som modulatorer af chemokinreceptoraktivitet
GB0120461D0 (en) 2001-08-22 2001-10-17 Astrazeneca Ab Novel compounds
GB0122503D0 (en) 2001-09-18 2001-11-07 Astrazeneca Ab Chemical compounds
SE0200844D0 (sv) 2002-03-19 2002-03-19 Astrazeneca Ab Chemical compounds
SE0200843D0 (sv) 2002-03-19 2002-03-19 Astrazeneca Ab Chemical compounds
SE0300957D0 (sv) 2003-04-01 2003-04-01 Astrazeneca Ab Chemical compounds
WO2005058874A1 (en) 2003-12-18 2005-06-30 Tibotec Pharmaceuticals Ltd. 5- or 6-substituted benzimidazole derivatives as inhibitors of respiratory syncytial virus replication
US7355051B2 (en) 2003-12-18 2008-04-08 Tibotec Pharmaceuticals Piperdine-amino-benzimidazole derivatives as inhibitors of respiratory syncytial virus replication
JP4166160B2 (ja) * 2004-01-19 2008-10-15 トヨタ自動車株式会社 内燃機関を始動するための回転電機の制御装置
JP4249149B2 (ja) * 2005-03-25 2009-04-02 富士通株式会社 プリアンプ回路の機能検証方法および，これを用いる磁気記録再生装置
EP2402316A1 (en) 2005-07-21 2012-01-04 AstraZeneca AB (Publ) Piperidine derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4219559A (en) * 1979-01-10 1980-08-26 Janssen Pharmaceutica N.V. N-Heterocyclyl-4-piperidinamines
CA1140119A (en) * 1978-04-03 1983-01-25 Joseph Torremans N-heterocyclyl-4-piperidinamines
US4556660A (en) * 1982-07-12 1985-12-03 Janssen Pharmaceutica N.V. N-(Bicyclic heterocyclyl)-4-piperidinamines
EP0144101B1 (en) * 1983-11-30 1991-02-06 Janssen Pharmaceutica N.V. Bicyclic heterocyclyl containing n-(bicyclic heterocyclyl)-4-piperidinamines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100280281B1 (ko) * 1993-05-19 2001-03-02 죠지폴릭 신발용 신발레이싱장치

Also Published As

Publication number Publication date
BG43007A3 (en) 1988-03-15
ZW16484A1 (en) 1986-04-30
HU207514B (en) 1993-04-28
FI81797C (fi) 1990-12-10
DE3476204D1 (de) 1989-02-23
US4634704A (en) 1987-01-06
NO844009L (no) 1985-04-09
DK478484A (da) 1985-04-07
KR870001509B1 (ko) 1987-08-20
FI81797B (fi) 1990-08-31
PT79307B (en) 1986-11-13
NZ209642A (en) 1987-04-30
CA1247614A (en) 1988-12-28
JPH0798818B2 (ja) 1995-10-25
EP0145037A3 (en) 1985-07-10
DK163239C (da) 1992-06-29
FI843934L (fi) 1985-04-07
PT79307A (en) 1984-11-01
IL73118A (en) 1988-03-31
EP0145037A2 (en) 1985-06-19
AU3387284A (en) 1985-04-18
ES8602763A1 (es) 1985-11-16
NO160441B (no) 1989-01-09
NO160441C (no) 1989-04-19
DK163239B (da) 1992-02-10
RO90457A (ro) 1986-12-10
PH21310A (en) 1987-09-28
FI843934A0 (fi) 1984-10-05
ES536590A0 (es) 1985-11-16
JPS6110577A (ja) 1986-01-18
DK478484D0 (da) 1984-10-05
HUT38629A (en) 1986-06-30
EP0145037B1 (en) 1989-01-18
AU565884B2 (en) 1987-10-01

Similar Documents

Publication Publication Date Title
KR850002981A (ko) 5원 헤테로사이클 고리를 갖는 n-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조방법
KR850005437A (ko) N-(4-피페리딘일)비사이클 축합 2-이미다졸아민 유도체의 제조방법
KR840008016A (ko) 융합 이미다졸 화합물의 제조방법
KR910021369A (ko) 산화질소의 생합성 억제제
KR890000469A (ko) (1h-아졸-1-일메틸)치환된 벤조트리아졸 유도체
KR840001174A (ko) 카르바 페넴 화합물의 제조방법
KR880003935A (ko) (1h-이미다졸-1-일메틸)치환된 벤즈이미다졸 유도체
KR950018008A (ko) 3-퀴놀론카르복실산 유도체의 단일-반응기 제조 방법
MX9706382A (es) Derivados de benzoilo.
KR930019664A (ko) 1-[2-(아릴술포닐아미노)-1-옥소에틸] 피페리딘 유도체 및 그것의 제조방법과 치료적 용융
ES2201104T3 (es) Derivados de benzociclohexilimidazoltiona.
KR850003534A (ko) N-(비사이클 헤테로사이클릴)-4-피페리딘아민의 제조방법
KR840005425A (ko) 1,4 디하이드로피리딘의 제조방법
ES8403460A1 (es) Un procedimiento para la preparacion de derivados de caprolactama.
KR910019975A (ko) 인돌 유도체
KR860008173A (ko) 치환된 n-[(4-피페리딘일)알킬]비사이클축합 옥사졸아민 및 티아졸아민의 제조방법
KR930006018A (ko) 이미다조피리딘 유도체 및 그의 제조방법
KR900018088A (ko) 피페리디닐, 피롤리디닐 및 피레라지닐 알킬페놀 에테르 유도체
KR840000563A (ko) 세펨 화합물의 제조방법
KR910006256A (ko) 신규의 티아졸 유도체와 그것의 제조방법 및 그것을 함유한 약제 조성물
KR850007427A (ko) 항균 화합물의 제조방법
US6359145B1 (en) Imidazole compounds
KR880000450A (ko) 세팔로스포린 유도체의 제조방법
KR940005586A (ko) 피리다지논 유도체 및 그의 제조방법
KR900018058A (ko) 아자사이클릭 카복실산 유도체, 이의 제조방법 및 용도

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
G160 Decision to publish patent application
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 19930813

Year of fee payment: 7

LAPS Lapse due to unpaid annual fee