KR102458265B1 - 담즙산 유도체, 특히 오베티콜산의 합성을 위한 중간체 - Google Patents

담즙산 유도체, 특히 오베티콜산의 합성을 위한 중간체 Download PDF

Info

Publication number
KR102458265B1
KR102458265B1 KR1020187035834A KR20187035834A KR102458265B1 KR 102458265 B1 KR102458265 B1 KR 102458265B1 KR 1020187035834 A KR1020187035834 A KR 1020187035834A KR 20187035834 A KR20187035834 A KR 20187035834A KR 102458265 B1 KR102458265 B1 KR 102458265B1
Authority
KR
South Korea
Prior art keywords
compound
formula
group
ethyl
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
KR1020187035834A
Other languages
English (en)
Korean (ko)
Other versions
KR20190009322A (ko
Inventor
알렉산더 찰스 웨이머스-윌슨
조피아 콤스타
로라 월리스
티모시 에반스
이안 데이비스
칼 오터
리스 배철러
Original Assignee
엔제트피 유케이 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
Application filed by 엔제트피 유케이 리미티드 filed Critical 엔제트피 유케이 리미티드
Publication of KR20190009322A publication Critical patent/KR20190009322A/ko
Application granted granted Critical
Publication of KR102458265B1 publication Critical patent/KR102458265B1/ko
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J17/00Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J21/00Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005Ketals
    • C07J21/008Ketals at position 17
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J33/00Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J33/00Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J33/002Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C07J41/0061Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0088Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing unsubstituted amino radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J41/00Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0094Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J43/00Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J51/00Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005Oxygen-containing hetero ring
    • C07J71/001Oxiranes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J13/00Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J21/00Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J21/005Ketals
    • C07J21/006Ketals at position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J31/00Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/006Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J9/00Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
KR1020187035834A 2016-05-18 2017-05-18 담즙산 유도체, 특히 오베티콜산의 합성을 위한 중간체 Active KR102458265B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB1608777.7A GB201608777D0 (en) 2016-05-18 2016-05-18 Compounds
GB1608777.7 2016-05-18
PCT/GB2017/051385 WO2017199033A1 (en) 2016-05-18 2017-05-18 Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid

Publications (2)

Publication Number Publication Date
KR20190009322A KR20190009322A (ko) 2019-01-28
KR102458265B1 true KR102458265B1 (ko) 2022-10-25

Family

ID=56320629

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020187035834A Active KR102458265B1 (ko) 2016-05-18 2017-05-18 담즙산 유도체, 특히 오베티콜산의 합성을 위한 중간체

Country Status (14)

Country Link
US (2) US10968250B2 (https=)
EP (2) EP3458469B1 (https=)
JP (1) JP7034093B2 (https=)
KR (1) KR102458265B1 (https=)
CN (1) CN109415407B (https=)
AU (1) AU2017266539B2 (https=)
EA (1) EA037584B1 (https=)
ES (2) ES2970336T3 (https=)
GB (1) GB201608777D0 (https=)
HR (1) HRP20211128T1 (https=)
HU (1) HUE054851T2 (https=)
MX (1) MX378591B (https=)
PT (1) PT3458469T (https=)
WO (1) WO2017199033A1 (https=)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201608776D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds
EP3431486A1 (en) * 2017-07-18 2019-01-23 Bionice, S.L.U. Process and intermediates for the synthesis of obeticholic acid and derivatives thereof
GB201812382D0 (en) 2018-07-30 2018-09-12 Nzp Uk Ltd Compounds
CN111138509B (zh) * 2018-11-02 2022-12-06 东莞东阳光药物研发有限公司 奥贝胆酸的制备方法
CN111072744B (zh) * 2019-12-03 2021-09-14 江苏佳尔科药业集团股份有限公司 一种以ba为原料合成熊去氧胆酸的方法
CN114315945A (zh) * 2020-09-28 2022-04-12 四川澄华生物科技有限公司 一种胆甾酸及其衍生物的除杂方法
CN112341516B (zh) * 2020-11-14 2022-07-15 湖南科瑞生物制药股份有限公司 5,6-环氧类固醇类化合物及其制备方法和应用
EP4423105A2 (en) * 2021-11-02 2024-09-04 Sandhill One, LLC High purity non-animal derived udca

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2624748A (en) 1950-09-09 1953-01-06 Upjohn Co Bisnorchola-4, 6-dien-3-one-22-al
US4289872A (en) 1979-04-06 1981-09-15 Allied Corporation Macromolecular highly branched homogeneous compound based on lysine units
US5229490A (en) 1987-05-06 1993-07-20 The Rockefeller University Multiple antigen peptide system
CA2118130A1 (en) 1992-04-14 1993-10-28 Jean M. J. Frechet Dendritic based macromolecules and method of production
WO1994019366A1 (en) 1993-02-26 1994-09-01 Magainin Pharmaceuticals Inc. Chemical synthesis of squalamine
US5643575A (en) 1993-10-27 1997-07-01 Enzon, Inc. Non-antigenic branched polymer conjugates
US5932462A (en) 1995-01-10 1999-08-03 Shearwater Polymers, Inc. Multiarmed, monofunctional, polymer for coupling to molecules and surfaces
ES2248581T3 (es) 2001-03-12 2006-03-16 Intercept Pharmaceuticals, Inc. Esteroides como agonistas de fxr.
US20090062256A1 (en) 2001-06-01 2009-03-05 Bristol-Myers Squibb Pharma Company LACTAMS SUBSTITUTED BY CYCLIC SUCCINATES AS INHIBITORS OF Abeta PROTEIN PRODUCTION
AU2002352524B2 (en) 2001-11-07 2007-10-04 Nektar Therapeutics Branched polymers and their conjugates
EP1568706A1 (en) 2004-02-26 2005-08-31 Intercept Pharmaceuticals, Inc. Novel steroid agonist for FXR
ITMI20050912A1 (it) 2005-05-19 2006-11-20 Erregierre Spa Processo di preparazione di acidi 3-a-ya(b)-diidrossi-6-a(b)-alchil-5b-colanici
JP2007210888A (ja) * 2006-01-12 2007-08-23 Mitsubishi Chemicals Corp ステロイド化合物の製造方法
CN101374854A (zh) * 2006-01-12 2009-02-25 三菱化学株式会社 甾类化合物的制备方法
CN101395170A (zh) 2006-02-14 2009-03-25 英特塞普特药品公司 用于预防或治疗fxr介导的疾病或状态的作为fxr配体的胆汁酸衍生物
US7932244B2 (en) 2006-06-27 2011-04-26 Intercept Pharmaceuticals, Inc. Bile acid derivatives as FXR ligands for the prevention or treatment of FXR-mediated diseases or conditions
KR101555716B1 (ko) 2007-01-19 2015-09-25 인터셉트 파마슈티컬즈, 인크. Tgr5 조절제로서의 23-치환 담즙산 및 이의 사용 방법
WO2010014836A2 (en) 2008-07-30 2010-02-04 Intercept Pharmaceuticals, Inc. Tgr5 modulators and methods of use thereof
DK2698375T3 (en) 2008-11-19 2018-05-28 Intercept Pharmaceuticals Inc TGR5 modulators and methods for using them
ES2774368T3 (es) 2008-11-19 2020-07-20 Intercept Pharmaceuticals Inc Moduladores de TGR5 y métodos de uso de los mismos
EP2459581A4 (en) 2009-07-29 2012-12-26 Univ Chicago LIVER X-RECEPTOR AGONISTS
SI3336097T1 (sl) 2012-06-19 2021-07-30 Intercept Pharmaceuticals, Inc. Priprava nekristalinične oblike obetiholne kisline
SG11201503247UA (en) 2012-10-26 2015-06-29 Intercept Pharmaceuticals Inc Process for preparing bile acid derivatives
AU2013352288B2 (en) 2012-11-28 2017-11-23 Intercept Pharmaceuticals, Inc. Treatment of pulmonary disease
US20140206657A1 (en) * 2013-01-18 2014-07-24 City Of Hope Bile acid analog tgr5 agonists
TN2015000497A1 (en) 2013-05-14 2017-04-06 Intercept Pharmaceuticals Inc 11-hydroxyl-derivatives of bile acids and amino acid conjugates thereof as farnesoid x receptor modulators
SG11201509371XA (en) 2013-05-24 2015-12-30 Nestec Sa Pathway specific markers for diagnosing irritable bowel syndrome
US10166246B2 (en) 2014-05-27 2019-01-01 City Of Hope TGR5 agonist complexes for treating diabetes and cancer
SMT202000070T1 (it) 2014-05-29 2020-03-13 Bar Pharmaceuticals S R L Derivati del colano per l'uso del trattamento e/o la prevenzione di malattie mediate da fxr e tgr5/gpbar1
SG11201703717SA (en) 2014-11-06 2017-06-29 Enanta Pharm Inc Bile acid analogs an fxr/tgr5 agonists and methods of use thereof
CN107207559B (zh) * 2014-11-19 2019-10-25 Nzp英国有限公司 作为制备类固醇fxr调节剂的中间体的6-烷基-7-羟基-4-烯-3-酮类固醇
KR102527821B1 (ko) 2014-11-19 2023-05-02 엔제트피 유케이 리미티드 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-6,7-다이온 스테로이드
KR102546748B1 (ko) * 2014-11-19 2023-06-22 엔제트피 유케이 리미티드 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-3,7-다이온 스테로이드
EA033445B1 (ru) 2014-11-19 2019-10-31 Nzp Uk Ltd 5-бета-6-алкил-7-гидрокси-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr
EP3223823A4 (en) 2014-11-26 2018-10-17 Enanta Pharmaceuticals, Inc. Bile acid analogs as fxr/tgr5 agonists and methods of use thereof
US11578097B2 (en) 2014-11-26 2023-02-14 Enanta Pharmaceuticals, Inc. Tetrazole derivatives of bile acids as FXR/TGR5 agonists and methods of use thereof
US10208081B2 (en) 2014-11-26 2019-02-19 Enanta Pharmaceuticals, Inc. Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof
WO2016086134A1 (en) 2014-11-26 2016-06-02 Enanta Pharmaceuticals, Inc. Bile acid derivatives as fxr/tgr5 agonists and methods of use thereof
CN105348365A (zh) * 2014-12-03 2016-02-24 四川百利药业有限责任公司 一种胆酸衍生物及其制备方法、药物组合物和用途
CN106279328A (zh) 2015-05-20 2017-01-04 重庆药友制药有限责任公司 一种制备6α-烷基鹅去氧胆酸的方法
JP6861703B2 (ja) 2015-06-19 2021-04-21 インターセプト ファーマシューティカルズ, インコーポレイテッド Tgr5修飾物質およびその使用方法
CN106397522A (zh) 2015-07-31 2017-02-15 中国人民解放军军事医学科学院毒物药物研究所 3,7‑二(叔丁基二甲基硅基氧基)‑6‑烯‑5β‑胆烷‑24‑酸甲酯
CN106478759A (zh) 2015-08-31 2017-03-08 陕西合成药业股份有限公司 奥贝胆酸衍生物及其制备方法和用途
CN106478756A (zh) 2015-09-02 2017-03-08 中美华世通生物医药科技(武汉)有限公司 Oca-e单晶及其制备方法和用途
CN106518946A (zh) 2015-09-10 2017-03-22 上海迪诺医药科技有限公司 磺酰脲衍生物、其药物组合物及应用
GB201608776D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds
GB201608779D0 (en) 2016-05-18 2016-06-29 Dextra Lab Ltd Methods and compounds

Also Published As

Publication number Publication date
MX378591B (es) 2025-03-11
PT3458469T (pt) 2021-06-11
US10968250B2 (en) 2021-04-06
EP3848382B1 (en) 2023-11-29
MX2018014164A (es) 2019-04-01
JP2019516720A (ja) 2019-06-20
HUE054851T2 (hu) 2021-10-28
US20210179661A1 (en) 2021-06-17
US20190284227A1 (en) 2019-09-19
ES2970336T3 (es) 2024-05-28
AU2017266539A1 (en) 2018-11-15
EA201892514A1 (ru) 2019-05-31
CN109415407B (zh) 2021-08-17
CA3024281A1 (en) 2017-11-23
HRP20211128T1 (hr) 2022-01-07
EP3458469B1 (en) 2021-04-14
JP7034093B2 (ja) 2022-03-11
GB201608777D0 (en) 2016-06-29
EP3848382A1 (en) 2021-07-14
AU2017266539B2 (en) 2021-04-15
EP3458469A1 (en) 2019-03-27
US11479577B2 (en) 2022-10-25
ES2878577T3 (es) 2021-11-19
CN109415407A (zh) 2019-03-01
EP3848382C0 (en) 2023-11-29
BR112018073488A2 (pt) 2019-04-09
EA037584B1 (ru) 2021-04-16
WO2017199033A1 (en) 2017-11-23
KR20190009322A (ko) 2019-01-28

Similar Documents

Publication Publication Date Title
KR102458265B1 (ko) 담즙산 유도체, 특히 오베티콜산의 합성을 위한 중간체
KR102509432B1 (ko) 화학 중간체로서의 스테로이드 6.7.베타.-에폭사이드
KR102526631B1 (ko) 스테로이드 fxr 조절인자를 제조하기 위한 중간체로서의 6-알킬-7-하이드록시-4-엔-3-온 스테로이드
KR102546748B1 (ko) 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-3,7-다이온 스테로이드
KR102526632B1 (ko) 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 5β-6-알킬-7-하이드록시-3-온 스테로이드
KR102489565B1 (ko) 스테로이드 4,6-디엔의 6,7-알파-에폭시화를 위한 공정 및 중간체
KR20170099896A (ko) 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-6,7-다이온 스테로이드
HK40055816B (en) Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid
HK40055816A (en) Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid
CA3024281C (en) Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid
HK40006370B (en) Intermediates for the synthesis of bile acid derivatives, in particular of obeticholic acid
BR112018073488B1 (pt) Intermediários para a síntese de derivados de ácido biliar, em particular de ácido obeticólico e seu processo de preparação
BR112018073492B1 (pt) Processos de preparo de compostos intermediários na síntese de derivados de ácido biliar com atividade farmacológica
HK40006371B (en) Steroid 6.7.beta.-epoxides as chemical intermediates
HK40006371A (en) Steroid 6.7.beta.-epoxides as chemical intermediates
HK40006372A (en) Process for the 6,7-alpha-epoxidation of steroid 4,6-dienes
HK40006372B (en) Process for the 6,7-alpha-epoxidation of steroid 4,6-dienes

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

A201 Request for examination
P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

T11-X000 Administrative time limit extension requested

St.27 status event code: U-3-3-T10-T11-oth-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

U11 Full renewal or maintenance fee paid

Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-OTH-PR1001 (AS PROVIDED BY THE NATIONAL OFFICE)

Year of fee payment: 4