KR900012903A - 피롤리딘 화합물 및 약제학적 용도 - Google Patents

피롤리딘 화합물 및 약제학적 용도 Download PDF

Info

Publication number
KR900012903A
KR900012903A KR1019900001296A KR900001296A KR900012903A KR 900012903 A KR900012903 A KR 900012903A KR 1019900001296 A KR1019900001296 A KR 1019900001296A KR 900001296 A KR900001296 A KR 900001296A KR 900012903 A KR900012903 A KR 900012903A
Authority
KR
South Korea
Prior art keywords
pyrrolidine
compound
salt
dihydroxyphenyl
hydroxyphenyl
Prior art date
Application number
KR1019900001296A
Other languages
English (en)
Other versions
KR920003892B1 (ko
Inventor
모또스께 야마나까
도모노리 호시꼬
신지 스다
나오끼 요네다
노부유끼 모리
미쓰마사 시노
히로끼 이시하라
마모루 사이또오
도시유끼 마쓰오까
Original Assignee
나이또오 하루오
에자이 가부시끼가이샤
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 JP1254349A external-priority patent/JP2928288B2/ja
Application filed by 나이또오 하루오, 에자이 가부시끼가이샤 filed Critical 나이또오 하루오
Publication of KR900012903A publication Critical patent/KR900012903A/ko
Application granted granted Critical
Publication of KR920003892B1 publication Critical patent/KR920003892B1/ko

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with 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
    • C07D207/12Oxygen or sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with 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
    • C07D207/14Nitrogen atoms not forming part of a nitro radical
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with 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
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
    • C07D207/2732-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D207/282-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/04Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06Heterocyclic 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음

Description

피롤리딘 화합물 및 약제학적 용도
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (27)

  1. 다음식을 갖는 피롤리딘 화합물 및 약리학적으로 허용되는 그의 염.
    상기식에서 X는 수소, 할로겐, 또는 저급알킬이며, Y는 -(CH2)n-(n은 0,1 또는 2), -S(O)p-(p는 0,1 또는 2), -O-, 또는 -NH-이고, R은 페닐, 치환기를 갖는 페닐, 나프틸, 치환기를 갖는 나프틸, 헤테로아릴 또는 치환기르 헤테로 아릴이다.
  2. 제1항에 있어서, Y는 -(CH2)n인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  3. 제1항에 있어서, Y는 -(CH2)n이며 n은 0인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  4. 제1항에 있어서, Y는 -(CH2)n이며 n은 1 또는 2인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  5. 제1항에 있어서, R은 다음식을 갖는 것을 특징으로 하는 피롤리딘 화화물 및 그의 염.
    상기식에서 R1, R2및 R3는 각각 수소, 저급알킬, 저급알콕시, 할로겐, 히드록시, 트리플루오로메틸 또는 -NR4R5이며, R4및 R5는 각각 수소 또는 저급알킬이다.
  6. 제5항에 있어서, Y는 -(CH2)n이고 n은 0인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  7. 제5항에 있어서, Y는 -(CH2)n이고 n은 1 또는 2인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  8. 제5항에 있어서, R1, R2및 R3는 각각 수소, 할로겐, 히드록시, 또는 저급알킬이며, Y는 -(CH2)n이고 n은 0인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  9. 제5항에 있어서, R1, R2및 R3는 각각 수소, 할로겐, 히드록시, 또는 저급알킬이며, Y는 -(CH2)n이고 n은 0인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  10. 제1항에 있어서, 화합물은 3-(2-클로로-3-히드록시페닐)-4-(3,4-디히드록시페닐)-피롤리딘인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  11. 제1항에 있어서, 화합물은(±)-트랜스-3-(2-클로로-3-히드록시페닐)-4-(3,4-디히드록시페닐)-피롤리딘인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  12. 제1항에 있어서, 화합물은(-)-트랜스-3-(2-클로로-3-히드록시페닐)-4-(3,4-디히드록시페닐)-피롤리딘인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  13. 제1항에 있어서, 화합물은 다음으로 구성되는 군으로부터 선택되는 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
    3-(3,4-디히드록시페닐)-4-(2-메틸페닐) 피롤리딘
    3-(2-클로로페닐)-4-(3,4-디히드록시페닐) 피롤리딘
    3-(2-클로로-3-히드록시페닐)-4-(3,4-디히드록시페닐) 피롤리딘
    3-(3,4-디히드록시페닐)-4-(3-메틸페닐) 피롤리딘 브롬화 수소산염
    (3,4-디히드록시페닐)-4-(3-메틸페닐) 피롤리딘
    3-(7-벤조티오페닐)-4-(3,4-디히드록시페닐) 피롤리딘
    3-(3-클로로-6-히드록시페닐)-1-메틸-4-(3,4-디히드록시페닐) 피롤리딘
    3-(2,6-디히드록시페닐)메틸-4-(3,4-디히드록시페닐) 피롤리딘
    3-(3-클로로-2,6-디히드록시페닐)메틸-4-(3,4-디히드록시페닐) 피롤리딘
    3-(3,5-디플루오로-2-히드록시페닐)메틸-4-(3,4-디히드록시페닐) 피롤리딘
    3-(3-플루오로-2-히드록시페닐)메틸-4-(3,4-디히드록시페닐) 피롤리딘
  14. 제13항에 있어서, 화합물은 트랜스형인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  15. 제1항에 있어서, R은 페닐 또는 치환된 페닐인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  16. 제15항에 있어서 치환된 페닐은 저급알킬, 트리플루오로메틸, 할로겐 및 히드록시로부터 선택된 치환기를 갖는 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  17. 제1항에 있어서, R은 헤테로아릴 또는 치환기를 갖는 헤테로 아릴인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  18. 제1항에 있어서, R은 티에닐 또는 치환기를 갖는 티에닐인 것을 특징으로 하는 하는 피롤리딘 화합물 및 그의 염.
  19. 제1항에 있어서, R은 저급알킬 또는 히드록시를 갖는 티에닐인 것을 특징으로 하는 피롤리딘 화합물 및 그의 염.
  20. 제1항에 정의된 치료학적 유효량의 화합물 또는 그의 염과 약리학적으로 허용되는 담체로 이루어지는 것을 특징으로 하는 약제학적 조성물.
  21. 제20항에 있어서, 도파민 1 아고니스트 활성이 효과적인 질병의 치료 또는 예방에 사용되는 것을 특징으로 하는 조성물.
  22. 제20항에 있어서, 고혈압의 치료 또는 예방에 사용되는 것을 특징으로 하는 조성물.
  23. 제20항에 있어서, 심기능부전의 치료 또는 예방에 사용되는 것을 특징으로 하는 조성물.
  24. 제1항에 정의된 화합물 또는 그의 염으로 이루어지는 도파민 1 아고니스트.
  25. 도파민 1 아고니스트 활성이 효과적인 질병의 치료 또는 예방 방법에 있어서, 치료학적 또는 예방학적 유효량의 제1항에 정의된 화합물 또는 그의 염을 상기 질병에 걸린 환자에게 투여하는 것으로 이루어지는 방법.
  26. 고혈압에 걸린 환자에게 치료학적 또는 예방학적 유효량의 제1항에 정의된 화합물 또는 그의 염을 투여하는 것으로 이루어지는 고혈압의 치료 또는 예방방법.
  27. 심기능부전에 걸린 환자에게 치료학적 또는 예방학적 유효량의 제1항에 정의된 화합물 또는 그의 염을 투여하는 것으로 이루어지는 심기능부전의 치료 또는 예방방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900001296A 1989-02-03 1990-02-03 피롤리딘 화합물 및 약제학적 용도 KR920003892B1 (ko)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP1-25262 1989-02-03
JP25262 1989-02-03
JP2526289 1989-02-03
JP1254349A JP2928288B2 (ja) 1989-09-29 1989-09-29 ピロリジン誘導体
JP1-254349 1989-09-29
JP254349 1989-09-29

Publications (2)

Publication Number Publication Date
KR900012903A true KR900012903A (ko) 1990-09-03
KR920003892B1 KR920003892B1 (ko) 1992-05-18

Family

ID=26362859

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900001296A KR920003892B1 (ko) 1989-02-03 1990-02-03 피롤리딘 화합물 및 약제학적 용도

Country Status (15)

Country Link
US (1) US5444083A (ko)
EP (1) EP0381235B1 (ko)
KR (1) KR920003892B1 (ko)
CN (1) CN1044652A (ko)
AT (1) ATE92043T1 (ko)
CA (1) CA2009162A1 (ko)
DE (1) DE69002338T2 (ko)
DK (1) DK0381235T3 (ko)
ES (1) ES2058620T3 (ko)
FI (1) FI900353A0 (ko)
HU (1) HUT53867A (ko)
NO (1) NO173988C (ko)
NZ (1) NZ232334A (ko)
PT (1) PT93045A (ko)
RU (1) RU2024506C1 (ko)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3210663B2 (ja) * 1990-04-06 2001-09-17 エーザイ株式会社 カテコール化合物を含有する経口用固形製剤
ATE201669T1 (de) * 1991-04-17 2001-06-15 Upjohn Co Substituierte (s)-3-phenylpiperidin derivate, deren herstellung und deren verwendung als dopamin autorezeptor antagonisten
US5665754A (en) * 1993-09-20 1997-09-09 Glaxo Wellcome Inc. Substituted pyrrolidines
CA2214685C (en) * 1995-03-10 2008-05-20 Berlex Laboratories, Inc. Benzamidine derivatives their preparation and their use as anti-coagulants
US6294561B1 (en) 1999-12-23 2001-09-25 Icos Corporation Cyclic AMP-specific phosphodiesterase inhibitors
US6514226B1 (en) * 2000-02-10 2003-02-04 Chf Solutions, Inc. Method and apparatus for treatment of congestive heart failure by improving perfusion of the kidney
WO2001068600A2 (en) * 2000-03-16 2001-09-20 Inflazyme Pharmaceuticals Limited Benzylated pde4 inhibitors
DE10257356A1 (de) * 2002-12-09 2004-06-24 Bayer Ag Fluorhaltige Aromaten
CA2690091A1 (en) * 2007-06-05 2008-12-11 Nsab, Filial Af Neurosearch Sweden Ab, Sverige New disubstituted phenylpyrrolidines as modulators of cortical catecholaminergic neurotransmission
CN103012175A (zh) * 2012-12-21 2013-04-03 东南大学 抗肿瘤含氮取代基姜黄素类似物、其盐及制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2852526A (en) * 1955-05-03 1958-09-16 Schering Corp Substituted pyrrolidines
AT232503B (de) * 1962-03-05 1964-03-25 Boehringer Sohn Ingelheim Verfahren zur Herstellung von neuen 3-Phenyl-pyrrolidinen und deren Salzen
FR2460929A1 (fr) * 1979-07-06 1981-01-30 Roussel Uclaf Nouveaux derives de l'a-phenyl 2-pyrrolidinemethanol et leur sels, procede de preparation, application a titre de medicaments et compositions les renfermant
KR840000486A (ko) * 1981-07-22 1984-02-22 원본미기재 치환된 피롤리딘의 제조방법

Also Published As

Publication number Publication date
PT93045A (pt) 1990-08-31
DK0381235T3 (da) 1993-10-04
NO173988B (no) 1993-11-22
EP0381235B1 (en) 1993-07-28
NZ232334A (en) 1991-06-25
CA2009162A1 (en) 1990-08-03
AU619943B2 (en) 1992-02-06
RU2024506C1 (ru) 1994-12-15
ES2058620T3 (es) 1994-11-01
NO900417D0 (no) 1990-01-30
HU900654D0 (en) 1990-04-28
DE69002338D1 (de) 1993-09-02
ATE92043T1 (de) 1993-08-15
DE69002338T2 (de) 1993-12-16
NO900417L (no) 1990-08-06
US5444083A (en) 1995-08-22
EP0381235A2 (en) 1990-08-08
AU4901390A (en) 1990-11-01
KR920003892B1 (ko) 1992-05-18
FI900353A0 (fi) 1990-01-23
HUT53867A (en) 1990-12-28
CN1044652A (zh) 1990-08-15
EP0381235A3 (en) 1991-04-03
NO173988C (no) 1994-03-02

Similar Documents

Publication Publication Date Title
DE69716226T2 (de) Difluoroprostaglandin-Derivate und ihre Anwendung
KR920021556A (ko) 라파 마이신 이량체
LV10860A (lv) Fenilalkilaminu iegusanas panemiens
KR890005031A (ko) L-도파유도체 또는 그의 산부가염, 그의 제조방법 및 그의 용도
FR2800735B1 (fr) Nouvelles aralkyle-1,2-diamines possedant une activite calcimimetique et leur mode de preparation
KR920021493A (ko) 페녹시페닐 유도체
KR900012903A (ko) 피롤리딘 화합물 및 약제학적 용도
KR890011596A (ko) 불면증 치료용 의약품의 제조에 있어서 1,4-이치환-피페리디닐 화합물의 용도
RU92016545A (ru) Гетероциклические соединения, способ их получения и фармацевтическая композиция
KR950010891A (ko) 내성 종양을 치료하는 방법
KR950016727A (ko) 트롬보모듈린 발현을 증가시키는 방법
KR900018091A (ko) 진경제
DE69909782D1 (de) Verwendung von benzofuroxanderivaten zur behandlung von angina pectoris
KR910018023A (ko) 기억력 증진제로서 유용한 5-아릴-4-알킬-3h-1,2,4-트리아졸-3-티온
DE69518706T2 (de) Verwendung von Diphenylethanderivaten zur Herstellung eines Arzneimittels zur Behandlung von Glaukom
KR880007494A (ko) 5-아릴-3h-1,2,4-트리아졸-3-온 및 진경제로서의 그들의 용도
DK0485219T3 (da) Lægemidler til forebyggelse og behandling af kredsløbsorgansygdomme indeholdende spiro-3-heteroazolidinforbindelser
KR950702544A (ko) 비페닐메탄 유도체 및 이를 함유하는 약제
KR880007495A (ko) 5-아릴-3h-1,2,4-트리아졸-3-온 및 신경변성 질환의 치료에 있어서의 그들의 용도
KR900001665A (ko) 사이클로알킬티아졸 유도체
KR890003372A (ko) 피리미도[2,1-b] 벤조티아졸 유도체로된 동맥경화 치료의약
KR890014566A (ko) 알콕시- 및 알킬아미노-카보닐알킬포스포리피드, 이의 제조방법 및 약제로서의 이의 용도
KR930005621A (ko) 고혈압 치료용 제약 조성물
KR950704322A (ko) 스피로푸라논 유도체 및 그의 신경변성 질환 치료 용도(Spirofuranone Derivatives and Their Use in the Treatment of Neurodegenerative Disorders)
DE69405999T2 (de) Pharmazeutisch wirksame enantiomere

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
LAPS Lapse due to unpaid annual fee