KR850007259A - 벤조디옥시노피롤 유도체의 제조방법 - Google Patents

벤조디옥시노피롤 유도체의 제조방법 Download PDF

Info

Publication number
KR850007259A
KR850007259A KR1019850002771A KR850002771A KR850007259A KR 850007259 A KR850007259 A KR 850007259A KR 1019850002771 A KR1019850002771 A KR 1019850002771A KR 850002771 A KR850002771 A KR 850002771A KR 850007259 A KR850007259 A KR 850007259A
Authority
KR
South Korea
Prior art keywords
compound
alkyl
hydrogen
formula
sup
Prior art date
Application number
KR1019850002771A
Other languages
English (en)
Other versions
KR920003065B1 (ko
Inventor
키친(외 4) 죤
Original Assignee
배리앤토니 뉴섬
글락소그룹 리미티드
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
Priority claimed from GB848410456A external-priority patent/GB8410456D0/en
Priority claimed from GB858503975A external-priority patent/GB8503975D0/en
Application filed by 배리앤토니 뉴섬, 글락소그룹 리미티드 filed Critical 배리앤토니 뉴섬
Publication of KR850007259A publication Critical patent/KR850007259A/ko
Application granted granted Critical
Publication of KR920003065B1 publication Critical patent/KR920003065B1/ko

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/06Peri-condensed systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/12Antidiarrhoeals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/04Centrally acting analgesics, e.g. opioids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/06Antimigraine agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/26Psychostimulants, e.g. nicotine, cocaine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/12Antihypertensives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D319/00Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/101,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/141,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/161,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/201,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • C07D491/056Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Child & Adolescent Psychology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Light Receiving Elements (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

내용 없음

Description

벤조디옥시노피롤 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. (a) 일반식(Ⅱ)의 화합물을 암모니아, 수성암모니아 또는 일반식 RNH2의 아민(여기서, R은 수소 또는 -CHO 그룹이 아닌 경우를 제외하고는 일반식(Ⅰ)의 R에 대하여 정의한 바와 같다)으로 아민화시키거나; (b) R이 수소인 일반식(Ⅰ)의 화합물을 제조하기 위하여 R이 보호그룹인 상응하는 화합물을 탈보호시키거나; (c) R이 알킬인 일반식(Ⅰ)의 화합물을 제조하기 위하여 R이 아실인 상응하는 화합물을 환원시키고, 경우에 따라서는 이와같이 제조된 화합물 또는 그의 염을, (D)(i) 일반식(Ⅰ)의 다른 화합물로 전환시키고/시키거나, (D)(ⅱ) 생리학적으로 허용가능한 그의 염으로 전환시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물 또는 생리학적으로 허용가능한 그의 염을 제조하는 방법.
    상기식에서, R은 수소, C1-C6알킬(C3-C7시클로-알킬로 임의 치환됨), C3-C6알케닐, C3-C6알키닐, C3-C7시클로알킬, 아르알킬(여기서 알킬잔기는 1 내지 5개의 탄소원자를 함유한다)또는 -CHO이고; R1은 할로겐, C1-C4알킬, C1-C4알콕시, 히드록실, 시아노, 니트로 및 -NR3R4(여기서 R3및 R5는 각각 수소 또는 C1-C4알킬이다)이고; R2는 수소, 할로겐, C1-C4알킬, C1-C4알콕시, 히드록실시아노, 니트로 또는 -NR3R4(여기서 R3및 R4는 각각 수소 또는 C1-C4-알킬이다)이다.
  2. 제1항에 있어서, R이 수소인 방법.
  3. 제1항에 있어서, R이 C1-C3알킬인 방법.
  4. 제1항에 있어서, R1이 할로겐, C1-C4-알킬 또는 C1-C4알콕시인 방법.
  5. 제1항에 있어서, R2가 수소 또는 불소인 방법.
  6. 제1항에 있어서, R이 수소, 메틸 또는 에틸이고, R1이 염소, 불소, 메틸 또는 메톡시이고, R2가 수소 또는 불소인 방법.
  7. 제1항에 있어서, (±)-트란스-2,3,3a,9a-테트라히드로-5-메틸-1H-[,4] 벤조디옥시노 [2,3-C] 피롤, 그의 3aS-, 3aR-이성체; (±)-트란스-5-클로로-2,3,3a,9a-테트라히드로-1H-[1,4] 벤조디옥시노 [2,3-C] 피롤, 그의 3aS-, 3aR-이성체;(±)-트란스-5,8-디플루오로-2,3,3a,9a-테트라히드로-1H-[1,4] 벤조디옥시노 [2,3-C] 피롤, 그의 3aS-, 3aR-이성체; 및 생리학적으로 허용가능한 그들의 염을 제조하는 방법.
  8. 제1항에 있어서, (±)-트란스-5-플루오로-2,3,3a,9a-테트라히드로-1H-[1,4] 벤조디옥시노 [2,3-C] 피롤, 그의 3aS-, 3aR-이성체 및 생리학적으로 허용가능한 그들의 염을 제조하는 방법.
  9. 제8항에 있어서, (±)-트란스-5-플루오로-2,3,3a,9a-테트라히드로-1H-[1,4] 벤조디옥시노 [2,3-C] 피롤히드로클로라이드 또는 그의 3aS- 또는 3aR-이성체인 방법.
  10. 제1항 내지 제9항중 어느 하나에 있어서, 공정(a)에서 바람직하게는 적절한 염기의 존재하에 또는 과량의 아민(RNH2)의 존재하에 임의로는 용매중, 승온에서 아민화 반응을 수행하는 방법.
  11. 제1항 내지 제10항중 어느 하나에 있어서, 공정(b)에서 R이 수소인 일반식(Ⅰ)의 화합물을 제조하기 위하여 R이 아릴메틸인 상응하는 화합물을 가수소분해시키거나 산성 조건하에 처리하는 방법.
  12. 제1항 내지 제10항중 어느 하나에 있어서, 공정(b)에서 R이 수소인 일반식(Ⅰ)의 화합물을 제조하기 위하여 R이 아실인 상응하는 화합물을 산 또는 염기를 사용하여 가수분해시키는 방법.
  13. 제1항 내지 제12항중 어느 하나에 있어서, 공정(c)에서 R이 알킬인 일반식(Ⅰ)의 화합물을 제조하기 위하여 R이 아실인 상응하는 화합물을 환원시키는 방법.
  14. 제12항에 있어서, 에테르 또는 테트라히드로-푸란과 같은 적절한 용매중 리튬알루미늄 히드라이드 또는 디보란과 같은 환원제를 사용하여 환류조건과 같은 승온에서 환원시키는 방법.
    ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850002771A 1984-04-24 1985-04-24 벤조디옥시노피롤 유도체의 제조방법 KR920003065B1 (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB848410456A GB8410456D0 (en) 1984-04-24 1984-04-24 Chemical compounds
GB8410456 1984-04-24
GB8503975 1985-02-15
GB858503975A GB8503975D0 (en) 1985-02-15 1985-02-15 Chemical compounds

Publications (2)

Publication Number Publication Date
KR850007259A true KR850007259A (ko) 1985-12-02
KR920003065B1 KR920003065B1 (ko) 1992-04-13

Family

ID=26287645

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019850002771A KR920003065B1 (ko) 1984-04-24 1985-04-24 벤조디옥시노피롤 유도체의 제조방법

Country Status (21)

Country Link
US (1) US4880801A (ko)
EP (2) EP0162593B1 (ko)
JP (2) JPH02270878A (ko)
KR (1) KR920003065B1 (ko)
AT (1) ATE55605T1 (ko)
AU (1) AU577367B2 (ko)
CA (1) CA1256111A (ko)
CS (1) CS402491A3 (ko)
CY (2) CY1532A (ko)
DE (2) DE3579189D1 (ko)
DK (2) DK160556C (ko)
ES (2) ES8607311A1 (ko)
FI (1) FI84069C (ko)
GB (3) GB2201414B (ko)
GR (1) GR850993B (ko)
HK (2) HK42890A (ko)
IL (1) IL75011A (ko)
MX (1) MX9203233A (ko)
NZ (1) NZ211885A (ko)
PT (1) PT80344B (ko)
SG (2) SG23590G (ko)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8526210D0 (en) * 1985-10-23 1985-11-27 Glaxo Group Ltd Chemical compounds
GB8526209D0 (en) * 1985-10-23 1985-11-27 Glaxo Group Ltd Chemical process
US5225431A (en) * 1987-10-23 1993-07-06 Burroughs Wellcome Co. Therapeutic substituted indole compounds and compositions thereof
GB8828032D0 (en) * 1988-12-01 1989-01-05 Glaxo Group Ltd Medicaments
GB9012469D0 (en) * 1990-06-05 1990-07-25 Glaxo Group Ltd Medicaments
GB9119466D0 (en) * 1991-09-12 1991-10-23 Glaxo Group Ltd Chemical compounds
US6451806B2 (en) 1999-09-29 2002-09-17 Adolor Corporation Methods and compositions involving opioids and antagonists thereof
US6469030B2 (en) 1999-11-29 2002-10-22 Adolor Corporation Methods for the treatment and prevention of ileus
BRPI0409492A (pt) * 2003-04-18 2006-05-02 Pharmacia & Up John Company Ll terapias de combinação
GB2503187A (en) * 2011-09-15 2013-12-25 Univ Sussex Composition for use in the treatment of neurodevelopmental disorders

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2485539A1 (fr) * 1980-06-26 1981-12-31 Sori Soc Rech Ind Nouveau derive de pyranno-indole, son procede de preparation et son application en therapeutique
IL70034A0 (en) * 1982-10-25 1984-01-31 Glaxo Group Ltd Heterocyclic amino compounds,their preparation and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
SG23590G (en) 1990-07-13
DK160824C (da) 1991-10-07
ATE55605T1 (de) 1990-09-15
IL75011A (en) 1990-02-09
US4880801A (en) 1989-11-14
FI84069B (fi) 1991-06-28
GR850993B (ko) 1985-11-25
CA1256111A (en) 1989-06-20
GB2201414A (en) 1988-09-01
SG12293G (en) 1993-04-16
EP0359290A1 (en) 1990-03-21
FI851611L (fi) 1985-10-25
ES542516A0 (es) 1986-06-16
DK160556B (da) 1991-03-25
DE3587511D1 (de) 1993-09-09
DK184085A (da) 1985-10-25
JPH02270878A (ja) 1990-11-05
GB2157691A (en) 1985-10-30
EP0162593B1 (en) 1990-08-16
AU577367B2 (en) 1988-09-22
ES8801545A1 (es) 1988-02-01
GB2201414B (en) 1988-12-29
ES551509A0 (es) 1988-02-01
NZ211885A (en) 1988-09-29
FI84069C (fi) 1991-10-10
JPH02270819A (ja) 1990-11-05
DK141590D0 (da) 1990-06-08
GB8510449D0 (en) 1985-05-30
DE3587511T2 (de) 1993-11-18
DK141590A (da) 1990-06-08
CY1532A (en) 1990-11-16
DE3579189D1 (de) 1990-09-20
CY1695A (en) 1994-01-14
HK42890A (en) 1990-06-08
PT80344A (en) 1985-05-01
GB2157691B (en) 1989-07-05
DK184085D0 (da) 1985-04-24
HK112093A (en) 1993-10-29
KR920003065B1 (ko) 1992-04-13
CS402491A3 (en) 1992-10-14
GB8802949D0 (en) 1988-03-09
DK160824B (da) 1991-04-22
AU4166785A (en) 1985-10-31
GB8728949D0 (en) 1988-01-27
DK160556C (da) 1991-09-02
EP0162593A1 (en) 1985-11-27
EP0359290B1 (en) 1993-08-04
FI851611A0 (fi) 1985-04-24
MX9203233A (es) 1992-07-01
ES8607311A1 (es) 1986-06-16
PT80344B (pt) 1987-09-30

Similar Documents

Publication Publication Date Title
KR840006963A (ko) 4-아미노알킬-2(3h)-인돌론을 제조하는 방법
NL980043I1 (nl) Chinoline-tussenprodukten voor de synthese van 1H-imidazoc4,5-c!chinolines en 1H-imidazoc4,5-c!chinoline-4-amine.
KR850001171A (ko) 퀴놀린 화합물의 제조방법
KR850007259A (ko) 벤조디옥시노피롤 유도체의 제조방법
KR870008906A (ko) 마크로라이드 유도체의 제조방법
KR870002056A (ko) 치환된 프로파르길옥시아세토니트릴 유도체의 제조 방법
KR890000421A (ko) 치환된 인돌리논 유도체를 제조하는 향상된 방법
GB1148717A (en) Phenylbenz (f)-2,5-oxazocine derivatives and homologues and pharmaceutical compositions
KR870001199A (ko) 헤테로시클릭 화합물의 제조방법
AU554976B2 (en) 1-phenyl-2-aminocarbonylindole compounds
ES8801211A1 (es) Un procedimiento para preparar derivados de quinolona
ATE245624T1 (de) Verfahren zur herstellung substituierter allylamin derivative und deren salze
KR870002069A (ko) 2-(3,5-디알킬-4-히드록시페닐) 인돌 유도체의 제조방법
KR850007586A (ko) 피롤리돈 유도체의 제조방법
KR890016044A (ko) 트랜스-헥사하이드로-8-하이드록시-2,6-메타노-2h-퀴놀리진-3(4h)-온의 인돌-3-카복실산 에스테르의 제조방법
KR870004027A (ko) 디하이드로리제르그산의 n-알킬화 방법
GB933504A (en) New piperidine derivatives and methods for preparing the same
ATE117977T1 (de) Verfahren zur herstellung von alpha-beta- ungesättigten ketonen.
KR840006654A (ko) 트랜스-4aR-5-n-프로필-4,4a,5,6,7,8,8a,9-옥타하이드로-1H(및 2H)피라졸로[3,4-g]퀴놀린의 제조방법
KR930010027A (ko) 퀴놀론 유도체의 새로운 제조방법
KR860009015A (ko) 이소퀴놀린 화합물의 제조방법
PL298918A1 (en) Method of obtaining 5-chloroxindole
KR890002146A (ko) 1,8-나프티리딘 유도체의 제조방법
KR950017962A (ko) 퀴놀론 유도체의 제조방법
ES8302651A1 (es) Procedimiento para la obtencion de derivados de la 1,7-dihidropirano (4,3-b) pirrol-4,6-diona con actividad analgesica.

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: 19970830

Year of fee payment: 7

LAPS Lapse due to unpaid annual fee