KR860000270A - 벤조디아제핀 동족체의 제조방법 - Google Patents

벤조디아제핀 동족체의 제조방법 Download PDF

Info

Publication number
KR860000270A
KR860000270A KR1019850004551A KR850004551A KR860000270A KR 860000270 A KR860000270 A KR 860000270A KR 1019850004551 A KR1019850004551 A KR 1019850004551A KR 850004551 A KR850004551 A KR 850004551A KR 860000270 A KR860000270 A KR 860000270A
Authority
KR
South Korea
Prior art keywords
dihydro
benzodiazepin
methyl
fluorophenyl
phenyl
Prior art date
Application number
KR1019850004551A
Other languages
English (en)
Other versions
KR900003406B1 (ko
Inventor
프레이딩거(외 2) 로져엠.
Original Assignee
제임스 에프, 노톤
머크 앤드 캄파니 인코포레이티드
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 제임스 에프, 노톤, 머크 앤드 캄파니 인코포레이티드 filed Critical 제임스 에프, 노톤
Publication of KR860000270A publication Critical patent/KR860000270A/ko
Application granted granted Critical
Publication of KR900003406B1 publication Critical patent/KR900003406B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—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
    • C07D209/20—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 substituted additionally by nitrogen atoms, e.g. tryptophane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/22—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
    • C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
    • C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
    • C07D243/24—Oxygen 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
    • C07D405/02—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
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음

Description

벤조디아제핀 동족체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (51)

  1. 다음 반용도식들에 따라 제조함을 특징으로 하여, 일반식(Ⅰ) 화합물 및 그의 약제학적으로 허용되는 염을 제조하는 방법.
  10. 여기에서 (24) 화합물에서 R1및/또는 R8이 에스테르 [(CH2)nCOO-C1-C3알킬]잔기이면, 이 그룹은 통상적 방법으로 가수분해하여 상응하는 산잔기를 수득하거나 NH3로 처리하여 상응하는 아미드잔기를 다 얻을 수 있다.
  16. 상기식에서, R1은 수소, C1내지 C5의 직쇄 또는 측쇄 알킬, 저급 알케닐, 저급 알키닐, -(CH2)mCOOR6, -(CH2)n-사이클로저급알킬, -(CH2)m-CONR5, -(CH2)m-CN 또는 -(CH2)nCX3 10이며; R2는 수소, 저급 알킬, 치환되거나 비치환된 페닐(여기에서 치환체는 할로, 저급알킬, 저급알콕시, 저급알키리오, 카복실, 캅ㄱ시저급알킬, 니트로, -CF3및 하이드록시중의 하나 또는 둘 일수 있다),
  17. -(CH2)n-NR18SO2-(CH2)qR7또는 -CHR|4이며; R4및 R5는 독립적으로 수소, 저급 알킬 또는 사이클로저급알킬이고; R6는 수소, 저급알킬, 사이클로저급알킬, 치환되거나 비치환된페닐, 또는 치환되거나 비치환된 페닐-저급 알킬이며, 여기에서 페닐 또는 페닐저급알킬치환체는 할로, 저급 알킬, 저급 알콕시, 니트로 및 CA3중의 하나 또는 둘일 수 있고; R7및 Ra 7는 독립적으로 α-또는 β-나프틸, 치환되거나 비치환된 페닐(여기에서 치환체는 할로, -NO2, -OH, -NR4R5, 저급알킬, CF3, CN, SCF3, CH≡C, CH2SCF3,OCHF2, SH, S-페닐, PO3H, 저그알콕시 및 저급 알킬티오 중의 하나 또는 둘일 수 있다).
  19. 이며, 단 R7또는 Ra 7가인 경우에, -(CH2)nNH(CH2)qR7에서 g는 0 또는 1이 아니고,
  20. 에서 q는 0이 아니며; R8은 수소, 저급 알킬, 사이클로저급알킬, -(CH2)m-CONH2-(CH2)mCOOR6, -(CH|2)m-사이플로저급알킬, -(CH2)mNR4R6,-(CH2)m(CH2)n 또는이고; R9및 R10은 독립적으로 수소, -OH 또는 -CH3이며; R11및 R|12는 독립적으로 저급알킬 또는 사이플로저급알킬이고; R13은 수소, 산소, 저급 알킬, 아실 또는 사이플로저급알킬이며; R14는 저급 알킬 또는 페닐저급알킬이고; R15는 수소, 저급 알킬,또는 -NR16R17이며; R16및 R17은 독립적으로 수소 또는이고; R18은 수소, 저급 알킬 또는 아실이며; m은 1 내지 4이고; n은 0내지 4이며; p는 그의 인접부위에서 -----가 불포화된 경우에는 0이고, 그의 인접부위에서 -----가 포화된 경우에는 1이며, 단 R13이 산소이면 p가 1이고 -----는 불포화되며; p는 0내지 4이고; r은 1 또는 2이며; X1은 수소, -NO2, CF3, CN, OH, 저급알킬, 할로, 저급알킬티오, 저급 알콕시, -(CH2)nCOOR6,또는 -NR4R5이고; X2및 X3는 독립적으로 수소, -OH, -NO3, 할로, 저급알킬티오, 저급 알킬,또는 저급알콕시이며; X4는 황, 산소, CH2또는 NR8이고; X6는 수소, CF3, CN,-COOR6, NO2또는 할로이며, X6은 산소 또는 HH이고; X7은 산소, 황, HH 또는 NR15이며, 단 R1이 H가 아닌 경우에만 X7은 NR15일수 있고; X8은 수소 또는 저급알킬이며; X9및 X9 q는 독립적으로 NR18또는 산소이고; X10은 불소, 염소 또는 브롬이며; ----- 는 포화 또는 불포화 결합이다.
  21. 제1항에 있어서, R1은 수소, 저급 알킬 또는 -(CH2)mCOOR6이고; R2는 치환되거나 비치환된 페닐(여기에서 치환체는 할로, 저급알킬, 저급알콕시, 카복실, 카복시저급알킬, 니트로, -CF3및 하이드록시중의 하나 또는 둘일 수 있다), 또는 -(CH2)mCOOR6이며; R3은 -(CH2)mR7, -(CH2)nNH(CH2)qR7,--NH(CH2)2-3NHR7,-NH(CH2)2-3NHCOR7, 또는-이고; R4및 R5는 독립적으로 수소 또는 저급알킬이며; R6는 수소 또는 저급알킬이고; R7은- 또는 β-나프틸,
  23. 치환되거나 비치환된 페닐(여기에서 치환체는 할로, -NO2, -OH, -NR4R5, 저급알킬, CF3, 저급알콕시, 저급알킬티오, CN, -C≡CH, SCF3,OCHF2및 S-페닐중의 하나 또는 둘일 수 있다).
  25. 이며; R8은 수소, 저급알킬 또는이고; R9및 R10은 독립적으로 수소, -OH 또는 -CH3이며; R11및 R12는 독립적으로 저급알킬이고; R13은 수소, 산소, 저급알킬 또는 아실이며; R14는 저급알킬이고; R15는 수소 또는 저급알킬이며; m은 1 내지 4이고; n은 0내지 4이며; p는 그의 인접부위에서 -----가 불포화된 경우에는 0이고, 그의 인접부위에서 -----가 포화된 경우에는 1이며, 단, R13이 산소이면, P가 1이고 -----가 불포화되며; q는 0내지 4이고; r은 1 또는 2이며; X1은 수소, -NO2,CF3,CN,OH, 저급 알킬, 할로 저급알킬티오, 저급 알콕시, -(CH2)nCOOR6또는 -NR4R5이고; X2및 X3는 독립적으로 수소, -OH, -NO2, 할로, 저급알킬티오, 저급 알킬 또는 저급알콕시이며; X4는 황, 산소 또는 NR8이고; X6은 산소 또는 NH이며; X7은 산소이고; -----은 포화 또는 불포화 결합인 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 허용되는 염을 제조하는 방법.
  26. 제2항에 있어서, R1은 수소, 메틸, 에틸, 카복시메틸 또는 에틸카복시메틸이고; R2는 치환되거나 비치환된 페닐(여기에서 치환제는 할로 및 카복실 중의 하나 또는 둘일 수 있다), 또는 -(CH2)1-2COOR6이며, R3는 -(CH2)nR7,-(CH2)nNH(CH2)qR7,또는이고; R6은 수소 또는 저급 알킬이며; R7은 α- 또는 β-나프틸,
  28. 치환된 페닐(여기에서 치환체는 할로, 저급 알킬 및 CF3중의 하나 또는 둘일 수 있다), 또는 -CH=CH-이고; R8은 수소, 메틸 또는 에틸이며; R9및 R10은 독립적으로 수소, -OH 또는 -CH3이고; R13은 수소, 메틸 또는 포르밀이며; R14는 t-부틸이고; n은 0내지 4이며; p는 그의 인접부위에서 -----가 불포화된 경우에는 0이고, 그의 인접부위에서 -----가 포화된 경우에는 1이며, q는 0내지 4이고; r은 1 또는 2이며; X1은 수소, -NO2CF3CN,OH 또는 할로이고; X2및 X|3는 독립적으로 수소, --OH, -NO2또는 할로이며; X7은 산소이고; -----은 포화 또는 불포화 결합인 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 허용되는 염을 제조하는 방법.
  29. 제2항에 있어서, R1은 수소, 메틸 또는 카복시메틸이고; R2는 페닐, O-플루오로페닐, P-플루오로페닐, O-클로로페닐, P-클로로페닐, O-카복시페닐 2,4-디클로로페닐, 2,6-디플루오로페닐, -CH2, COOEt; -C,H2COO-t-Bu -CH2CH2COOEt 또는 -CH2CHCOO-t-Bu이며;
  30. R3은 -(CH2)1-2R7,-(CH2)0-1NH(CH2)1-2R7,또는이고, 입체화학은 D-트립토판과 관련되며;
  31. R6은 수소, 메틸 또는 에틸이고;
  32. R7은 α- 또는 β-나프틸,
  34. 모노 또는 디할로 페닐이며; R9및 R10은 독립적으로 수소 또는 -OH 이고; R13은 수소이며; R14는 t-부틸이고; P는 그의 인접부위에서 -----가 불포화된 경우에는 0이며, 그의 인접부위에서 -----가 포화된 경우에는 1이고; r은 1이며; X1은 수소, 7-클로로, 7-플루오로 또는 7-니트로이고; X2및 X3는 독립적으로 수소, -OH, 플루오로 또는 클로로이며; X7은 산소이고; -----는 포화 또는 불포화 결합인 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 허용되는 염을 제조하는 방법.
  35. 제1항에 있어서, 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴) 메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-[3'-(1'-메틸인돌릴)-메틸]-1-메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로 페닐)-3(R)-(3'-인돌릴)-메틸-1-메틸-2H-1,4-벤조디아제핀-2-온; 7-로클로-1,3-로디하이드로-3(R)-(3'-인돌릴)메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(R)-(3'-인돌릴)메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로 -5-(2-플루오로페닐)-3(R)-(3'-α-인돌레닐)메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌레닐)메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-티온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-7-로클로; 1,3-디하이드로-3(R)-벤질-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(R)-벤질옥시메틸-7-클로로-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3-디하이드로-3(RS)-(1-나프틸)메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3-디하이드로-3(RS)-(2-나프틸)메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(2-티에닐)메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(2-티에닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-[3'-β-(1'-t-Boc-L-로이실)-인돌레닐]메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-[3'-β-(1'-t-Boc-L-로이실)-인돌레닐]메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-[3'-α-(1'-t-Boc-D-로이실)-인돌레닐]메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-[3'-α-(1'-t-Boc-D-로이실)-인돌레닐]메틸-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3,4,5-테트라하이드로-3(R)-(3'-인돌릴)메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3,4,5-테트라하이드로-3(S)-(3'-인돌릴)메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 4-(P-클로로 벤조일)-5-(2-플루오로 페닐)-3(R)-[3'-(1'-메틸인돌릴)-메틸]-1-메틸-1,3,4,5-테트라하이드로-2H-1,4-벤조디아제핀-2-온;
  36. 4-아세틸-5-(2-플루오로 페닐)-3(R)-[3'-(1'-메틸인돌릴)-메틸]-1-메틸-1,3,4,5-테트라하이드로-2H-1,4-벤조디아제핀-2-온; 7-클로로-5-(2-클로로 페닐)-1,3-디하이드로-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(R)-[3'-인돌릴)메틸-5-메틸-2H-1,4-벤조디아제핀-2-온; 1-벤질-7-클로로-1,3-디하이드로-3(R)-(3'-인돌릴)-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3-디하이드로-3(R)-(3'-인돌릴)메틸-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로 페닐)-3(S)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1-벤질-7-클로로-1,3-디하이드로-3(S)-(3'-인돌릴)메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3-디하이드로-3(R)-(3'-인돌릴)메틸-5-페닐-2H-1,4-벤조디아제핀-2-티온; 1,3-디하이드로-5-(2-플루오로 페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-[N'-(3-티에노일)]하이드라지드;
  37. 1,3-디하이드로-1-에틸-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1-사이클로프로필메틸-1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-1-펜틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-1-(3-메틸부틸)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로 페닐)-3(R)-(3'-인돌릴)메틸-1-(2,2,2-트리플루오로에틸)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-1-(2-디메틸아미노에틸)-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온;
  38. 1,3-디하이드로-1-(에톡시카보닐 메틸)-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1-카복시메틸-1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(R)-[3'-(1'-p-클로로-벤질오일인돌릴)메틸]-1-메틸-2H-1,4-벤조디아제핀-2-온;
  39. 7-클로로-1,3-디하이드로-3(R)-[3'-(1'-벤질인돌릴)메틸]-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-[1-하이드록시-1-(3'-인돌릴)]메틸-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-1-메틸-5-페닐-3-(RS)-(3-티에노일)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-[1-하이드록시-1-(3-티에닐)]메틸-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-[1-하이드록시-1-[3-(1-메틸인돌릴)]]-메틸-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온, 2개의 입체이성체;
  40. 1,3-디하이드로-3(RS)-(1-하이드록시-1-페닐)메틸-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-[1-하이드록시-1-(2-티에닐)]메틸-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3-(RS)-하이드록시-1-메틸-5-페닐-3-(3'-티에노일)-2H-1,4-벤조디아제핀-2-온; 1,5-디하이드로-5-(RS)-하이드록시-1-메틸-5-페닐-3-(3'-티에노일)-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3-디하이드로-(R)-[(2',3'-디하이드로-2'-옥소-1,H-인돌-3'-일)메틸]-5-페닐-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3-디하이드로-3(R)-[(3'-(2,4-디니트로페닐)-이미다졸-5'-일)-메틸]-5-페닐]-2H-1,4-벤조디아제핀-2-온; 7-클로로-1,3-디하이드로-3(R)-[(3'-이미다졸-5'-일)-메틸]-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(RS)-[3'-(5'-브로모인돌릴)메틸]-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 5-O-카복시페닐-1,3-디하이드로-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온;
  41. 1,3-디하이드로-3(RS)-[3'-(5'-플루오로인돌릴)메틸]-5-0-플루오로페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-[3'-(6'-플루오로인돌릴)메틸]-5-0-플루오로페닐-2H-1,4-벤조디아제핀-2-온; 2-N-[2(RS), 3-비스-(Boc 아미노)프로파노일]아미노-2'-플루오로벤조페논,2-N-[2(RS),3-디프탈릴아미노프로파노일]아미노-2'-플루오로-벤조페논; 1,3-디하이드로-5-(2'-플루오로페닐)-3(SR)-아미노메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2'-플루오로페닐)-3(R)-(4-아미노)부틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2'-플루오로페닐)-3(RS)-벤질옥시-카보닐아미노메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2'-플루오로페닐)-3(RS)-(3-티오펜-카보닐)아미노메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2'-플루오로페닐)-3(RS)-(2-인돌)-카보닐아미노메틸)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2'-플루오로페닐)-3(RS)-(6'-클로로-피라지닐)아미노메틸-2H-1,4-벤조디아제핀-2-온;
  42. 1,3-디하이드로-5-(2'-플루오로페닐)-3(RS)-아미노메틸-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(RS)-(2-인돌카보닐 아미노)-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-[2-(3-인돌릴)에틸]아미노-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(RS)-[3-(3-인돌)프로피오닐아미노]-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(RS)-(3-인돌아세틸아미노)-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(RS)-(Boc-L-트립토파닐)아미노-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; Z-1,3-디하이드로-1-메틸-5-페닐-3-(3-티에닐메틸렌)-2H-1,4-벤조디아제핀-2-온; E-1,3-디하이드로-1-메틸-5-페닐-3-(3-티에닐메틸렌)-2H-1,4-벤조디아제핀-2-온; 3(RS)-(Boc-D-트립토필)아미노-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(RS)-[4-(3-인돌)부티릴아미노]-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(벤질옥시카보닐) 아미노메틸-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀; 1,3-디하이드로-3(RS)-[3'-(티오펜)카보닐]아미노-메틸-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀; 1,3-디하이드로-3(RS)-(2-인돌카보닐)아미노메틸-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀; 1,3-디하이드로-3(RS)-(2-L-하이드록시-2-페닐아세틸)아미노-메틸-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1-(2-시아노에틸)-1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1-(2-시아노에틸)-1,3-디하이드로-5-(2-플루오로페닐)-3(R)-[1'-(2-시아노에틸)-3'-인돌릴]-메틸-2H-1,4-벤조디아제핀-2-온; 1-(2-카복시에틸)-1,3-디하이드로-5-(2-플루오로페닐)-3(R)-(3'-인돌릴)메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(R)-(3'-인돌릴)메틸-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온-4-옥사이드; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-(2-인돌카보닐 아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(2-인돌카보닐아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-3(RS)-[2'-(1-메틸인돌)카보닐아미노]-2H-1,4-벤조디아제핀-2-온;
  43. 1,3-디하이드로-3(RS)-(4-니트로페닐카보닐)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(2-인돌카보닐옥시)-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(3-티오펜카보닐 아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(3-인돌카보닐아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온;
  44. 1,3-디하이드로-3(RS)-(4-티아나프텐아세틸)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(4-클로로페닐카보닐)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(4-메틸페닐설포닐)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1-카복시메틸-1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(2-인돌카보닐아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(5-플루오로인돌-2-카보닐아미노)-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(3'-메틸인데닐-2-카보닐)-아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(2-퀴날딜)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(2-L-하이드록시-2-페닐아세틸)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(5-클로로인돌-2-카보닐아미노)-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 3(RS)-[N-(2-인돌카보닐)-N-메틸아미노]-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(2-인돌카보닐 아미노)-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-1-메틸-3(RS)-[2-(1-메틸인돌)카보닐-아미노]-5-페닐-2H-1,4-벤조디아제핀-2-온; 1-카복시메틸-1,3-디하이드로-3(RS)-(2-인돌카보닐-아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(5-브로모인돌-2-카보닐 아미노)-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 3(RS)-신나모일아미노-1,3-디하이드로-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(5-하이드록시-2-인돌카보닐)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1-카복스아미도메틸-1,3-디하이드로-3R-(3-인돌릴메틸)-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-(2-인돌메틸아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(페닐아미노메틸카보닐)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(5-메톡시인돌-2-카보닐 아미노)-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(1-메틸인돌-2-카보닐 아미노)-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-1-메틸-3(RS)-(4-클로로페닐카보닐)-아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(2-벤조푸란카보닐 아미노)-2H-1,4-벤조디아제핀-2-온; 1-에톡시카보닐메틸-1,3-디하이드로-3(RS)-(4-클로로-페닐카보닐)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(4-클로로페닐카보닐)아미노-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-1-메틸-3(RS)-(4-클로로페닐카보닐)아미노-5-페닐-2H-1,4-벤조디아제핀-2-온; 1-카복시메틸-1,3-디하이드로-3(RS)-(4-클로로페닐-카보닐)아미노-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 3(RS)-(2(S)-3급-부톡시카보닐아미노-3-페닐 프로파노일-아미노)-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(RS)-(2-(S)-3급-부톡시카보닐 아미노-3-페닐프로파노일-아미노)-1,3-디하이드로-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(R)-및 3(S)-(2(S)-아미노-3-페닐프로파노일 아미노)-1,3-디하이드로-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(R)-및 3(S)-아미노-1,3-디하이드로-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(R)-및 3(S)-아미노-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(S)-(-)-1,3-디하이드로-3-(2-인돌카보닐아미노)-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(S)-(+)-1,3-디하이드로-5-(2-플루오로페닐)-3-(2-인돌-카브닐아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(R)-(-)-1,3-디하이드로-5-(2-플루오로페닐)-3-(2-인돌-카보닐 아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온;
  45. 3(R)-(-)-1,3-디하이드로-3-(4-클로로벤조일 아미노)5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(S)-(+)-1,3-디하이드로-3-(4-클로로벤조일아미노)-5-(2-플루오로 페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(S)-(-)-1,3-디하이드로-3-(4-브로모벤조일아미노)-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(R)-(+)-1,3-디하이드로-3-(4-브로모벤조일아미노)-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(R)-(+)-1,3-디하이드로-3-(2-인돌 카보닐아미노)-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3-(RS)-(2-인돌카보닐아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-(p-트리플루오로메틸 벤조일아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-(P-메틸-벤조일아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로 페닐)-3-(RS)-(p-메톡시-벤조일아미노)-2H-1,4-벤조디아제핀-2-온;
  46. 3-(RS)-(o-클로로벤조일아미노)-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(RS)-(o-클로로벤조일 메틸아미노)-1,3-디하이드로-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(RS)-(o-클로로벤조일 아미노)-1,3-디하이드로-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(RS)-(m-클로로벤조일 아미노)-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(RS)-(3,4-디클로로벤조일 아미노)-1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(RS)-(p-클로로벤조일 아미노)-1,3-디하이드로-5-(2'-플루오로페닐)-1-메틸-4-옥소-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-페닐-3-(RS)-(4'-메틸티오벤조일 아미노)-2H-1,4-벤조디아제핀-2-온;
  47. 1,3-디하이드로-3-(RS)-(4'-플루오로벤조일 아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-페닐-3-(RS)-(4'-트리플루오로메틸-벤조일아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3-(RS)-(4'-3급-부틸벤조일아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(RS)-(3,5-디클로로벤조일아미노)1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3-(RS)-(p-하이드록시벤조일아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(RS)-(4'-시아노벤조일아미노)1,3-디하이드로-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(S)-(-)-3-(2-클로로벤조일아미노)-1,3-디하이드로-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(R)-(+)-3-(2-클로로벤조일 아미노)-1,3-디하이드로-1-메틸-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(p-디메틸아미노 벤조일아미노)-5-(2-플루오로페닐)--2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3-(RS)-(3,4-디메톡시벤조일 아미노)-5-(2-플루오로페닐)-2H-1,4-벤조디아제핀-2-온; 3-(S)-(+)-3-(3-브로모벤조일아미노)-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-페닐-3(RS)-(3-트리플루오로 메틸티오-벤조일 아미노)-2H-1,4-벤조디아제핀-2-온; 3-(S)-(+)-3-(4-브로모벤조일아미노)-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3-(S)-(+)-3-(4-t-부틸벤조일 아미노)-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온;
  48. 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(피롤-2-카보닐아미노)-2H-1,4-벤조디아제핀-2-온; 3-(S)-(+)-1,3-디하이드로-5-(2-플루오로페닐)3-(4-요오도-벤조일아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(2-나프토일아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 3-(S)-(-)-3-(2-브로모벤조일아미노)-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3-(S)-(+)-3-(4-시아노벤조일아미노)-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온;
  49. 1,3-디하이드로-5-페닐-3(RS)-(4-n-프로필벤조일아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-페닐-3(RS)-(4-페닐벤조일아미노)-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(4-n-펜틸 벤조일아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-3(RS)-(1-나프토일아미노)-5-페닐-2H-1,4-벤조디아제핀-2-온; 3(S)-(+)-1,3-디하이드로-5-(2-플루오로페닐)-3-(3-요오도-벤조일아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온;
  50. 3(R)-(-)-1,3-디하이드로-5-(2-플루오로페닐)-3-(3-요오도-벤조일아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(R)-(+)-1,3-디하이드로-5-(2-플루오로페닐)-3-(2-요오도-벤조일아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(S)-(-)-1,3-디하이드로-5-(2-플루오로페닐)-3-(2-요오도-벤조일아미노)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(R)-(+)-3-(2-브로모벤조아미노)-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 3(R)-(+)-3-(2-클로로벤조일 아미노)-1,3-디하이드로-5-(2-플루오로페닐)-1-메틸-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-페닐카보닐-아미노-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(2-클로로페닐)-카보닐아미노-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-벤질옥시카보닐-아미노-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-벤질옥시카보닐-아미노-2H-1,4-벤조디아제핀-2-온; 1-(4-클로로페닐)카보닐-1,3-디하이드로-5-(2-플루오로-페닐)-3(RS)-(4-클로로페닐)카보닐아미노-2H-1,4-벤조디아제핀-2-온; 1-(4-클로로페닐)카보닐-1,3-디하이드로-5-(2-플루오로페닐)-3(RS)-(4-클로로페닐)카보닐옥시-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-(4-클로로페닐)-옥시-2H-1,4-벤조디아제핀-2-온; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-(4-클로로페닐)-카보닐아미노-2H-1,4-벤조디아제핀-2-티온; 1,3-디하이드로-5-(2-플루오로페닐)-3-(RS)-(2-인돌)카보닐아미노-2H-1,4-벤조디아제핀-2-티온; 또는 1,3-디하이드로-3(RS)-(4-클로로페닐)아미노카보닐아미노-2H-1,4-벤조디아제핀-2-온인 화합물을 제조하는 방법.
  51. ※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.
KR1019850004551A 1984-06-26 1985-06-26 벤조디아제핀 동족체 및 이를 함유하는 약제학적 조성물 KR900003406B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US62485484A 1984-06-26 1984-06-26
US624854 1984-06-26
US624,854 1984-06-26
US70527285A 1985-02-25 1985-02-25
US705,272 1985-02-25
US74197285A 1985-06-10 1985-06-10
US741,972 1985-06-10

Publications (2)

Publication Number Publication Date
KR860000270A true KR860000270A (ko) 1986-01-27
KR900003406B1 KR900003406B1 (ko) 1990-05-18

Family

ID=27417360

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019850004551A KR900003406B1 (ko) 1984-06-26 1985-06-26 벤조디아제핀 동족체 및 이를 함유하는 약제학적 조성물

Country Status (17)

Country Link
EP (1) EP0167919B1 (ko)
JP (1) JP2603214B2 (ko)
KR (1) KR900003406B1 (ko)
AT (1) ATE88998T1 (ko)
AU (2) AU4415285A (ko)
CA (1) CA1332410C (ko)
DE (1) DE3587316T2 (ko)
DK (1) DK175264B1 (ko)
ES (2) ES8704906A1 (ko)
GR (1) GR851539B (ko)
HK (1) HK15397A (ko)
IE (1) IE59900B1 (ko)
IL (1) IL75587A0 (ko)
NO (1) NO173651C (ko)
NZ (1) NZ212502A (ko)
PT (1) PT80717B (ko)
YU (1) YU46738B (ko)

Families Citing this family (76)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4755508A (en) * 1984-06-26 1988-07-05 Merck & Co., Inc. Benzodiazepine analogs and use as antogonists of gastrin and cholecystokinin
US4820834A (en) * 1984-06-26 1989-04-11 Merck & Co., Inc. Benzodiazepine analogs
EP0166354B1 (en) * 1984-06-26 1992-08-05 Merck & Co. Inc. Benzofused lactam compounds and pharmaceutical compositions containing them
DE3514696A1 (de) * 1985-04-24 1986-11-06 Bayer Ag, 5090 Leverkusen N-indolylethyl-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung
EP0253571B1 (en) * 1986-07-14 1989-08-23 Merck & Co. Inc. Process for resolution and race mization of amines with acidic alpha-hydrogens
JPH01211939A (ja) * 1988-02-18 1989-08-25 Nec Kyushu Ltd イオン注入装置
FR2630440B1 (fr) * 1988-04-25 1991-09-20 Jouveinal Sa Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique
US4970207A (en) * 1988-07-07 1990-11-13 Fujisawa Pharmaceutical Company, Ltd. Benzodiazepine derivatives
IL91361A (en) * 1988-09-09 1994-10-07 Fujisawa Pharmaceutical Co Benzodiazepinone compounds [4,1] connected via positions 1 and 9 and carrying two transducers, processes for their preparation and pharmaceutical preparations containing them
US4957915A (en) * 1989-02-27 1990-09-18 Biomeasure, Inc. Benzodiazepine analogs
PH26955A (en) * 1989-03-08 1992-12-03 Kali Chemie Pharma Gmbh Novel 1,7-fused 1H-indole-2-carboxylic acid N-(1,4-benzodiazepin-3-YL) amides
EP0386644B1 (en) * 1989-03-10 1997-06-04 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Reagents for the determination of drugs
DE69017302T3 (de) * 1989-08-04 1999-08-05 Merck Sharp & Dohme Zentrale Cholecystokinin-Antagonisten zur Behandlung von psychiatrischen Krankheiten.
FR2652352A1 (fr) * 1989-09-28 1991-03-29 Jouveinal Sa Benzodiazepines, leur procede et intermediaires de preparation et leurs applications en therapeutique.
FR2659331A1 (fr) * 1990-03-08 1991-09-13 Adir Nouveaux derives de la 4h-pyrrolo [1,2-a] thieno [3,2-f] [1,4]-diazepine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
CA2056809A1 (en) * 1990-12-07 1992-06-08 Mark G. Bock Benzodiazepine analogs
CA2099672A1 (en) * 1990-12-25 1992-06-26 Masato Satoh Benzodiazepine derivatives
IL101514A (en) * 1991-04-10 1996-01-31 Merck & Co Inc History of benzodiazepines and anticoagulants containing cholecystokinin containing them
CA2071181A1 (en) * 1991-06-14 1992-12-15 Roger M. Freidinger Benzodiazepine analogs
WO1993007131A1 (en) * 1991-10-10 1993-04-15 Merck Sharp & Dohme Limited Benzodiazepine derivatives and their use as antagonists of cholecystokinin and/or gastrin receptors
DE69204040T2 (de) * 1991-12-20 1996-03-28 Merck Sharp & Dohme 3-Phenylureido-1,4-Benzodiazepinone und ihre Verwendung als Cholecystokinin- oder Gastrinantagonisten.
GB9203790D0 (en) * 1992-02-21 1992-04-08 Merck Sharp & Dohme Therapeutic agents
CA2130195A1 (en) * 1992-03-16 1993-09-30 Mark Gary Bock Benzodiazepine derivatives, compositions containing them and their use in therapy
WO1993019052A1 (en) * 1992-03-24 1993-09-30 Merck Sharp & Dohme Limited 3-ureido substituted benzodiazepin-2-ones having cholecystokinin and/or gastrin antagonistic activity and their use in therapy
US5360802A (en) * 1992-05-11 1994-11-01 Merck Sharpe & Dohme Ltd. Benzodiazepine derivatives, compositions containing them and their use in therapy
AU670597B2 (en) * 1992-06-24 1996-07-25 Ferring B.V. Novel benzodiazepine derivative
FR2694006A1 (fr) * 1992-07-22 1994-01-28 Esteve Labor Dr Amides dérivés de benzohétérocyles.
US5521175A (en) * 1992-07-29 1996-05-28 Merck Sharp & Dohme Ltd. Benzodiazepine derivatives
EP0763537A3 (en) * 1993-05-14 1997-10-22 Genentech Inc Non-peptides farnesyl transfer inhibitors
AU678503B2 (en) * 1993-09-24 1997-05-29 Takeda Chemical Industries Ltd. Condensed heterocyclic compounds and their use as squalene synthetase inhibitors
FR2716194B1 (fr) * 1994-02-14 1996-05-31 Sanofi Elf Dérivés de 3-acylamino-5-phényl-1,4-benzodiazépin-2-one polysubstitués, leur procédé de préparation et les compositions pharmaceutiques les contenant.
FR2716195B1 (fr) * 1994-02-14 1996-06-21 Sanofi Sa Dérivés de 3-acylamino-5-phényl-1,4-benzodiazépin-2-one polysubstitués, leur procédé de préparation et les compositions pharmaceutiques les contenant.
HU220635B1 (hu) * 1994-08-18 2002-03-28 Merck & Co. Inc. 2,3-Dihidro-1-(2,2,2-trifluor-etil)-2-oxo-5-fenil-1H-1,4-benzodiazepin-származékok, ezeket tartalmazó gyógyszerkészítmények és alkalmazásuk gyógyszerkészítmények előállítására
CA2195973A1 (en) * 1994-08-18 1996-02-29 David A. Claremon N-2,3-dihydro-1-(2-propyl)-2-oxo-5-phenyl-1h-1,4-benzodiazepines
US5556969A (en) * 1994-12-07 1996-09-17 Merck Sharp & Dohme Ltd. Benzodiazepine derivatives
CA2257948A1 (en) * 1996-06-28 1998-01-08 Merck & Co., Inc. Antiarrhythmic combinations of selective iks antagonists with beta-adenergic blocking agents
US6063794A (en) 1996-10-11 2000-05-16 Cor Therapeutics Inc. Selective factor Xa inhibitors
US6369080B2 (en) 1996-10-11 2002-04-09 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US6194435B1 (en) 1996-10-11 2001-02-27 Cor Therapeutics, Inc. Lactams as selective factor Xa inhibitors
US6262047B1 (en) 1996-10-11 2001-07-17 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US6635632B1 (en) 1996-12-23 2003-10-21 Athena Neurosciences, Inc. Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
US6683075B1 (en) 1996-12-23 2004-01-27 Athena Neurosciences, Inc. Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use
AU6896398A (en) 1997-04-14 1998-11-11 Cor Therapeutics, Inc. Selective factor xa inhibitors
JP2002513412A (ja) 1997-04-14 2002-05-08 シーオーアール セラピューティクス インコーポレイテッド 選択的Ｘａ因子阻害剤
EP0977772A1 (en) 1997-04-14 2000-02-09 Cor Therapeutics, Inc. SELECTIVE FACTOR Xa INHIBITORS
WO1998046628A1 (en) * 1997-04-14 1998-10-22 Cor Therapeutics, Inc. SELECTIVE FACTOR Xa INHIBITORS
US6218382B1 (en) 1997-08-11 2001-04-17 Cor Therapeutics, Inc Selective factor Xa inhibitors
US6228854B1 (en) 1997-08-11 2001-05-08 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US6333321B1 (en) 1997-08-11 2001-12-25 Cor Therapeutics, Inc. Selective factor Xa inhibitors
US6958330B1 (en) 1998-06-22 2005-10-25 Elan Pharmaceuticals, Inc. Polycyclic α-amino-ε-caprolactams and related compounds
US6552013B1 (en) 1998-06-22 2003-04-22 Elan Pharmaceuticals, Inc. Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
US6774125B2 (en) 1998-06-22 2004-08-10 Elan Pharmaceuticals, Inc. Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
US6528505B1 (en) 1998-06-22 2003-03-04 Elan Pharmaceuticals, Inc. Cyclic amino acid compounds pharmaceutical compositions comprising same and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
US6569851B1 (en) 1998-06-22 2003-05-27 Elan Pharmaceutials, Inc. Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
US6509331B1 (en) 1998-06-22 2003-01-21 Elan Pharmaceuticals, Inc. Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
US7160880B1 (en) 1999-05-14 2007-01-09 Cenes Limited Short-acting benzodiazepines
AU776283B2 (en) 1999-12-02 2004-09-02 Zeria Pharmaceutical Co., Ltd. Calcium salts of 1,5-benzodiazepine derivatives, process for producing the salts and drugs containing the same
GB0012671D0 (en) * 2000-05-24 2000-07-19 Merck Sharp & Dohme Therapeutic agents
MXPA05002871A (es) 2002-09-20 2005-10-05 Arrow Therapeutics Ltd Derivados de benzodiazaepina y composiciones farmaceuticas que los contienen.
EP1591120A4 (en) 2003-01-28 2009-06-10 Takeda Chemical Industries Ltd RECEPTOR AGONISTS
BRPI0520554A2 (pt) 2005-09-19 2009-06-13 Arrow Therapeutics Ltd uso de uma benzodiazepina ou um sal farmaceuticamente aceitável do mesmo, método para tratar ou prevenir uma infecção por hcv em um paciente, derivado de benzodiazepina ou um sal famaceuticamente aceitável do mesmo, e, composição farmacêutica
PL2081921T3 (pl) 2006-07-10 2011-03-31 Paion Uk Ltd Krótko działające sole benzodiazepiny i ich formy polimorficzne
EP2450039A1 (en) 2010-11-08 2012-05-09 PAION UK Ltd. Dosing regimen for sedation with CNS 7056 (Remimazolam)
AR094963A1 (es) 2013-03-04 2015-09-09 Ono Pharmaceutical Co Reacción de oxidación excelente en el índice de conversión
GB201414116D0 (en) 2014-08-08 2014-09-24 Trio Medicines Ltd Benzodiazepine derivatives
LT3324977T (lt) * 2015-07-22 2022-10-25 Enanta Pharmaceuticals, Inc. Benzodiazepino dariniai kaip rsv inhibitoriai
GB201513979D0 (en) 2015-08-07 2015-09-23 Trio Medicines Ltd Synthesis of benzodiazepine derivatives
EP3178886A1 (en) 2015-12-10 2017-06-14 DyStar Colours Distribution GmbH High wet fast brilliant blue disperse dye mixtures
WO2019006295A1 (en) 2017-06-30 2019-01-03 Enanta Pharmaceuticals, Inc. HETEROCYCLIC COMPOUNDS AS RSV INHIBITORS
UY38614A (es) 2019-03-18 2020-10-30 Enanta Pharm Inc Derivados de benzodiazepinas como inhibidores del rsv
US20220162173A1 (en) * 2019-03-25 2022-05-26 President And Fellows Of Harvard College Compositions and methods for reducing tactile dysfunction, anxiety, and social impairment
CA3153297A1 (en) 2019-10-04 2021-04-08 Adam SZYMANIAK Antiviral heterocyclic compounds
US11505558B1 (en) 2019-10-04 2022-11-22 Enanta Pharmaceuticals, Inc. Antiviral heterocyclic compounds
UY39032A (es) 2020-01-24 2021-07-30 Enanta Pharm Inc Compuestos heterocíclicos como agentes antivirales
WO2022010882A1 (en) 2020-07-07 2022-01-13 Enanta Pharmaceuticals, Inc, Dihydroquinoxaline and dihydropyridopyrazine derivatives as rsv inhibitors
US11945824B2 (en) 2020-10-19 2024-04-02 Enanta Pharmaceuticals, Inc. Heterocyclic compounds as anti-viral agents

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH414652A (de) * 1959-12-10 1966-06-15 Hoffmann La Roche Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten
US3402171A (en) * 1960-12-02 1968-09-17 Hoffmann La Roche Process for preparing 5-aryl-3h-1, 4-benzodiazepin-2(1h)-ones
US3297755A (en) * 1960-12-02 1967-01-10 Hoffmann La Roche 2-chloro-5-trifluoromethylbenzo-phenone compounds
US3336295A (en) * 1960-12-02 1967-08-15 Hoffmann La Roche Hydroxy or alkoxy substituted 5-phenyl-3h-1, 4-benzodiazepin-2(1h)-ones
GB1034872A (en) * 1962-04-16 1966-07-06 American Home Prod Benzodiazepine derivatives
BE656606A (ko) * 1963-12-03
GB1056289A (en) * 1964-01-14 1967-01-25 Delmar Chem 2-phthalimido acetamido benzophenones and their preparation
GB1039947A (en) * 1964-04-06 1966-08-24 Engelhard Ind Inc Improvements in or relating to gold plating
GB1173320A (en) * 1966-12-13 1969-12-10 Delmar Chem Derivatives of Benzodiazepinones
US3558603A (en) * 1967-12-01 1971-01-26 Sumitomo Chemical Co Process for producing benzodiazepine derivatives
US3778433A (en) * 1969-04-18 1973-12-11 Sumitomo Chemical Co Process for producing benzodiazepine derivatives
DE1923821A1 (de) * 1969-05-09 1970-11-19 Wuelfing J A Fa 1,2,4,5-Tetrahydro-[3H]-benzo-1,4-diazepin-2,5-dion-Derivate,Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneipraeparaten
US3867529A (en) * 1970-08-24 1975-02-18 Giorgio Ferrari Tranquilizing and anti-anxiety pharmaceutical compositions
US4045569A (en) * 1971-03-17 1977-08-30 Franjo Kajfez Optically active 1,4-benzodiazepines and process for use as a tranquilizer
US4065451A (en) * 1971-03-30 1977-12-27 American Home Products 1,3-Dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts
US3801568A (en) * 1972-02-07 1974-04-02 American Home Prod Optically active 1,3-dihydro-3-substituted 5-phenyl-2h-1,4-benzodiazepin-2-ones and process for their separation
CH581606A5 (en) * 1972-08-02 1976-11-15 Crc Ricerca Chim 2-(Alpha-ammonio-acylamino) benzophenones - precursors for benzodiazepinone hypnotics and tranquillisers
DE2311714A1 (de) * 1973-03-09 1974-09-19 Thomae Gmbh Dr K Neue 1,4-benzodiazepine
CH573928A5 (ko) * 1973-07-30 1976-03-31 Crc Ricerca Chim
US5004741A (en) * 1984-06-26 1991-04-02 Merck & Co., Inc. Methods of antagonizing CCK or gastrin with benzodiazepine analogs

Also Published As

Publication number Publication date
DE3587316D1 (de) 1993-06-09
GR851539B (ko) 1985-11-25
EP0167919A2 (en) 1986-01-15
IL75587A0 (en) 1985-10-31
DK175264B1 (da) 2004-08-02
ATE88998T1 (de) 1993-05-15
NO173651B (no) 1993-10-04
DE3587316T2 (de) 1993-11-04
IE851582L (en) 1985-12-26
JPS6163666A (ja) 1986-04-01
ES8704906A1 (es) 1987-04-16
NO852558L (no) 1985-12-27
NZ212502A (en) 1989-03-29
YU106785A (en) 1988-12-31
ES8706132A1 (es) 1987-06-01
KR900003406B1 (ko) 1990-05-18
JP2603214B2 (ja) 1997-04-23
ES551504A0 (es) 1987-06-01
EP0167919B1 (en) 1993-05-05
DK287285A (da) 1986-02-25
DK287285D0 (da) 1985-06-25
IE59900B1 (en) 1994-04-20
AU4415285A (en) 1986-01-02
HK15397A (en) 1997-02-14
PT80717B (pt) 1987-10-20
AU4456389A (en) 1990-04-05
YU46738B (sh) 1994-04-05
PT80717A (en) 1985-07-01
ES544523A0 (es) 1987-04-16
EP0167919A3 (en) 1986-11-05
CA1332410C (en) 1994-10-11
NO173651C (no) 1994-01-12
AU640113B2 (en) 1993-08-19

Similar Documents

Publication Publication Date Title
KR860000270A (ko) 벤조디아제핀 동족체의 제조방법
KR880011126A (ko) 벤조디아제핀 동족체
KR910011263A (ko) 공포증을 치료하고 진통효과를 직접 유도하기 위한 벤조디아제핀 유사체
AU679085B2 (en) Benzodiazepine analogs
RU2135486C1 (ru) Производные 1,5-бензодиазепина, способ их получения и содержащий их фармацевтический состав
CA2384544A1 (en) Amino lactam sulfonamides as inhibitors of a.beta. protein production
CA2195973A1 (en) N-2,3-dihydro-1-(2-propyl)-2-oxo-5-phenyl-1h-1,4-benzodiazepines
EP0730454A1 (en) Antiarrhythmic benzodiazepines
US5569654A (en) Benzodiazepinones
WO2000007995A1 (en) SUCCINOYLAMINO LACTAMS AS INHIBITORS OF Aβ PROTEIN PRODUCTION
US4663321A (en) Triazolobenzodiazepines and pharmaceutical use
TW200423928A (en) Malonamide derivatives
SK282019B6 (sk) 2,3-dihydro-1-(2,2,2-trifluóretyl)-2-oxo-5-fenyl-1h-1,4- benzodiazepínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie
JPH11506760A (ja) 新規なｎ−（２，４−ジオキソ−２，３，４，５−テトラヒドロ−１ｈ−１，５−ベンゾジアゼピン−３イル）−３−アミド
AU671141B2 (en) Benzodiazepine derivatives
CA2065715A1 (en) Cholecystokinin antagonists
CA2065703A1 (en) Cholecystokinin antagonists
SK125495A3 (en) 1,5-benzodiazepine derivatives, manufacturing process, their use and pharmaceutical compositions containing them
EP0167920A2 (en) Benzodiazepine derivatives and pharmaceutical compositions containing them
CA2055094A1 (en) Cholecystokinin antagonist
EP0272868A1 (en) 1,4-Benzodiazepines with 6-membered heterocyclic rings
CA1177069A (en) Phenyl ketones
AU2003203805B8 (en) Succinoylamino lactams as inhibitors of ABeta protein production

Legal Events

Date Code Title Description
A201 Request for examination
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: 20050511

Year of fee payment: 16

EXPY Expiration of term