JP6841821B2 - てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物 - Google Patents

てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物 Download PDF

Info

Publication number
JP6841821B2
JP6841821B2 JP2018517734A JP2018517734A JP6841821B2 JP 6841821 B2 JP6841821 B2 JP 6841821B2 JP 2018517734 A JP2018517734 A JP 2018517734A JP 2018517734 A JP2018517734 A JP 2018517734A JP 6841821 B2 JP6841821 B2 JP 6841821B2
Authority
JP
Japan
Prior art keywords
salt
compound according
gaba
pharmaceutical composition
compound
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
JP2018517734A
Other languages
English (en)
Japanese (ja)
Other versions
JP2018531941A (ja
JP2018531941A5 (https=
Inventor
リチャード・ビー・シルバーマン
健二 高谷
健二 高谷
ホアン・ブイ・レー
ホセ・アイ・ジャンコーサ
Original Assignee
ノースウェスタン ユニバーシティ
ノースウェスタン ユニバーシティ
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 ノースウェスタン ユニバーシティ, ノースウェスタン ユニバーシティ filed Critical ノースウェスタン ユニバーシティ
Publication of JP2018531941A publication Critical patent/JP2018531941A/ja
Publication of JP2018531941A5 publication Critical patent/JP2018531941A5/ja
Application granted granted Critical
Publication of JP6841821B2 publication Critical patent/JP6841821B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/28—Drugs 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
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Epidemiology (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Child & Adolescent Psychology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Psychology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
JP2018517734A 2015-10-09 2016-10-10 てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物 Active JP6841821B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562239330P 2015-10-09 2015-10-09
US62/239,330 2015-10-09
PCT/US2016/056245 WO2017062942A2 (en) 2015-10-09 2016-10-10 (s)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid, and related compounds as gaba aminotransferase inactivators for the treatment of epilepsy, addiction and hepatocellular carcinoma

Publications (3)

Publication Number Publication Date
JP2018531941A JP2018531941A (ja) 2018-11-01
JP2018531941A5 JP2018531941A5 (https=) 2019-11-21
JP6841821B2 true JP6841821B2 (ja) 2021-03-10

Family

ID=58488679

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2018517734A Active JP6841821B2 (ja) 2015-10-09 2016-10-10 てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物

Country Status (20)

Country Link
US (3) US9670141B2 (https=)
EP (1) EP3341355B1 (https=)
JP (1) JP6841821B2 (https=)
KR (1) KR102745965B1 (https=)
CN (1) CN108137484B (https=)
AU (1) AU2016334396B2 (https=)
BR (1) BR112018007026B1 (https=)
CA (1) CA3001330A1 (https=)
CL (1) CL2018000914A1 (https=)
CO (1) CO2018003828A2 (https=)
DK (1) DK3341355T3 (https=)
ES (1) ES2825349T3 (https=)
HU (1) HUE053429T2 (https=)
IL (1) IL258516A (https=)
LT (1) LT3341355T (https=)
MX (1) MX380592B (https=)
PE (1) PE20190349A1 (https=)
PL (1) PL3341355T3 (https=)
PT (1) PT3341355T (https=)
WO (1) WO2017062942A2 (https=)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RS59111B1 (sr) 2014-08-21 2019-09-30 Boehringer Ingelheim Int Nova jedinjenja spiro[3h-indol-3,2´-pirolidin]-2(1h)-ona i derivati kao mdm2-p53 inhibitori
JP6841821B2 (ja) * 2015-10-09 2021-03-10 ノースウェスタン ユニバーシティ てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物
KR20240158360A (ko) 2015-10-09 2024-11-04 베링거 인겔하임 인터내셔날 게엠베하 Mdm2-p53 억제제로서의 스피로[3h-인돌-3,2'-피롤리딘]-2(1h)-온 화합물 및 유도체
EP4692048A3 (en) * 2017-02-08 2026-04-01 Ovid Therapeutics Inc. Methods of treating cdkl5 disorders with the compound ov329
US11771671B2 (en) 2018-02-08 2023-10-03 Ovid Therapeutics Inc. Use of (1S,3S)-3-amino-4-(difluoromethylidene) cyclopentane-1-carboxylic acid and (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid in the treatment of tinnitus, acute sensorineural hearing loss, Meniere's disease, Tourette's syndrome, attention deficit hyperactivity disorder and addiction
KR20250167147A (ko) 2018-02-08 2025-11-28 오비드 테라퓨틱스 인크. 이명, 급성 감각신경성 난청, 메니에르병, 투렛 증후군, 주의력 결핍 과잉행동 장애 및 중독의 치료에 있어서 (1s,3s)-3-아미노-4-(디플루오로메틸리덴) 시클로펜탄-1-카르복시산 및 (s)-3-아미노-4-(디플루오로메틸리덴)시클로펜트-1-엔-1-카르복시산의 용도
JP2021519753A (ja) * 2018-03-29 2021-08-12 オービッド・セラピューティクス・インコーポレイテッドＯｖｉｄ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｉｎｃ． 眼障害の治療における（１ｓ，３ｓ）−３−アミノ−４−（ジフルオロメチリデン）シクロペンタン−１−カルボン酸および（ｓ）−３−アミノ−４−（ジフルオロメチルエニル）シクロペンタ−１−エン−１−カルボン酸の使用
US10822301B2 (en) 2018-04-12 2020-11-03 Northwestern University 3-carbon substituted 4-aminocyclopent-1-ene-1-carboxylic acid compounds as inhibitors of gamma-aminobutyric acid (GABA) aminotransferase
MX2020012691A (es) * 2018-05-25 2021-02-15 Univ Northwestern Proceso para la sintesis del acido (s)-3-amino-4-(difluorometileni l)ciclopent-1-eno-1-carboxilico.
CA3102786A1 (en) * 2018-06-07 2019-12-12 Ovid Therapeutics Inc. Use of (s)-3-amino-4-(difluoromethylenyl) cyclopent-1-ene-1-carboxylic acid and related compounds, (1s,3s)-3-amino-4-(difluoromethylidene) cyclopentane-1-carboxylic acid and vigab atrin in the treatment of developmental disorders
US11203596B2 (en) 2019-02-25 2021-12-21 Northwestern University Analogs of 3-amino-4-(propan-2-ylidene)cyclopentane-1-carboxylic acid and uses thereof for treating diseases and disorders associated with ornithine aminotransferase activity
US11078153B2 (en) 2019-04-03 2021-08-03 Northwestern University 2-difluoro substituted 4-aminocyclopentanecarboxylic acids as inhibitors of gamma-aminobutyric acid aminotransferase and human ornithine aminotransferase
CN110935495B (zh) * 2019-11-29 2021-02-23 中国科学院电子学研究所 Gaba和电生理微纳同步传感检测芯片及其制备方法
US11993569B2 (en) 2020-01-23 2024-05-28 Northwestern University 3-amino-4-halocyclopentene carboxylic acids as inactivators of aminotransferases
WO2022187523A1 (en) * 2021-03-03 2022-09-09 Northwestern University (s)-3-amino-4,4-dihalocyclopent-1-enecarboxylic acid as selective inactivators of human ornithine aminotransferase
EP4482478A4 (en) * 2022-02-27 2026-03-04 Univ Northwestern (3S,4R)-3-AMINO-4-(DIFLUOROMETHYL)CYCLOPENT-1-ENE-1-CARBOXYLIC ACID AND RELATED COMPOUNDS USED AS SELECTIVE ORNITHIN AMINOTRANSFERASE ACTIVATORS
KR20250034134A (ko) * 2022-07-06 2025-03-10 오비드 테라퓨틱스 인크. 암 치료에 있어서 (s)-3-아미노-4-(디플루오로메틸렌일)사이클로펜트-1-엔-1-카르복실산의 사용
US20240285563A1 (en) * 2023-02-17 2024-08-29 Ovid Therapeutics Inc. Use of (s)-3-amino-4-(difluoromethylenyl) cyclopent-1-ene-1-carboxylic acid in the treatment of rheumatoid arthritis
EP4648757A4 (en) * 2023-02-17 2026-01-07 Ovid Therapeutics Inc USE OF (S)-3-AMINO-4-(DIFLUOROMETHYLENYL)CYCLOPENT-1-ENE-1-CARBOXYLIC ACID FOR THE TREATMENT OF GASTROINTESTINAL TRACT DISORDERS AND AS AN IMMUNOMODULATING AGENT
JP2026506097A (ja) * 2023-02-17 2026-02-20 オービッド・セラピューティクス・インコーポレイテッド 多発性硬化症の処置における（ｓ）－３－アミノ－４－（ジフルオロメチレニル）シクロペント－１－エン－１－カルボン酸の使用
US20240285565A1 (en) * 2023-02-17 2024-08-29 Ovid Therapeutics Inc. Use of (s)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid in the treatment of diabetes and pre-diabetes

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6794413B1 (en) * 2002-07-19 2004-09-21 Northwestern University Compounds and related methods for inhibition of γ-aminobutyric acid aminotransferase
IL177609A (en) * 2006-08-21 2015-11-30 Yaron Ilan Use of gobacoline or its analogue to produce a drug to treat liver carcinoma
CA2790820A1 (en) * 2010-02-25 2011-09-01 Northwestern University Use (1s,3s)-3-amino-4-difluoromethylenyl-1-cyclopentanoic acid as a gaba aminotransferse inhibitor
TWI468403B (zh) * 2011-08-30 2015-01-11 Gilead Sciences Inc 用於治療成癮之ａｌｄｈ－２抑制劑
JP6841821B2 (ja) * 2015-10-09 2021-03-10 ノースウェスタン ユニバーシティ てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物

Also Published As

Publication number Publication date
CO2018003828A2 (es) 2018-07-19
BR112018007026B1 (pt) 2022-06-21
MX380592B (es) 2025-03-12
CA3001330A1 (en) 2017-04-13
KR20180052782A (ko) 2018-05-18
CN108137484B (zh) 2021-02-12
JP2018531941A (ja) 2018-11-01
DK3341355T3 (da) 2020-10-26
IL258516A (en) 2018-05-31
PL3341355T3 (pl) 2021-03-08
US20170239202A1 (en) 2017-08-24
ES2825349T3 (es) 2021-05-17
MX2018004302A (es) 2018-11-09
US9993449B2 (en) 2018-06-12
WO2017062942A3 (en) 2018-03-01
HK1253002A1 (zh) 2019-06-06
CN108137484A (zh) 2018-06-08
BR112018007026A2 (pt) 2018-10-16
HUE053429T2 (hu) 2021-07-28
AU2016334396B2 (en) 2021-04-08
KR102745965B1 (ko) 2024-12-20
US9670141B2 (en) 2017-06-06
LT3341355T (lt) 2020-11-10
WO2017062942A2 (en) 2017-04-13
EP3341355A4 (en) 2019-04-10
US20170101364A1 (en) 2017-04-13
EP3341355A2 (en) 2018-07-04
EP3341355B1 (en) 2020-09-30
PE20190349A1 (es) 2019-03-07
PT3341355T (pt) 2020-10-21
US20180271816A1 (en) 2018-09-27
AU2016334396A1 (en) 2018-04-19
CL2018000914A1 (es) 2018-08-31

Similar Documents

Publication Publication Date Title
JP6841821B2 (ja) てんかん、嗜癖および肝細胞癌の処置のためのｇａｂａアミノトランスフェラーゼ不活性化剤としての（ｓ）−３−アミノ−４−（ジフルオロメチレニル）シクロペント−１−エン−１−カルボン酸および関連化合物
EP3873883B1 (en) Method of synthesis
Juncosa et al. Design and mechanism of (S)-3-amino-4-(difluoromethylenyl) cyclopent-1-ene-1-carboxylic acid, a highly potent γ-aminobutyric acid aminotransferase inactivator for the treatment of addiction
Zhu et al. A remarkable difference that one fluorine atom confers on the mechanisms of inactivation of human ornithine aminotransferase by two cyclohexene analogues of γ-aminobutyric acid
US12465578B2 (en) Substituted alpha-ethyl phenylalkylamines
Morieux et al. The Structure− Activity Relationship of the 3-Oxy Site in the Anticonvulsant (R)-N-Benzyl 2-Acetamido-3-methoxypropionamide
KR20230106659A (ko) 파킨슨병 제약 약물에 대한 민감화, 특히 l-dopa 유발 이상운동증의 예방 또는 감소에 사용하기 위한 [2-(3-플루오로-5-메탄술포닐페녹시)에틸](프로필)아민 (메스도페탐)
Cao et al. Structure-based design and optimization lead to the identification of a novel potent sEH inhibitor with PPARγ partial agonist activity against inflammatory and metabolic-related diseases
WO2021081523A1 (en) Fluorine substituted ceclohexene analogoues of gamma-aminobutyric acid (gaba)
Jain et al. Synthesis and pharmacological evaluation of novel arginine analogs as potential inhibitors of acetylcholine‐induced relaxation in rat thoracic aortic rings
WO2020198529A1 (en) Substituted amino-thiol and amino-disulfide compounds, and uses thereof
KR20160146689A (ko) 파킨슨병을 치료하기 위한 도파민 효능제 및 l-dopa 유도체를 포함하는 조성물
HK1253002B (zh) 作为用於治疗癫痫、成瘾和肝细胞癌的gaba氨基转移酶灭活剂的化合物
Wawro et al. Enantiomers of 2-methylglutamate and 2-methylglutamine selectively impact mouse brain metabolism and behavior
JPWO2018008552A1 (ja) １１ｃ標識カテコール誘導体、それを用いたリン酸化タウ凝集阻害剤のｐｅｔプローブ、及びそれらの製造方法
MX2007009007A (es) Derivados de acido aminobutanoico que inhiben carnitina palmitoil transferasa.
EP3994122B1 (fr) N-formylhydroxylamines en tant qu'inhibiteurs de la neprilysine (nep), en particulier en tant qu'inhibiteurs mixtes de l'aminopeptidase n (apn) et de la neprilysine (nep)
EP4482478A2 (en) (3s,4r)-3-amino-4-(difluoromethyl)cyclopent-1-ene-1-carboxylic acid and related compounds as selective inactivators of ornithine aminotransferase
CA3237375A1 (en) Cysteamine and/or cystamine prodrugs
Yuan Novel substrates and inhibitors of γ-aminobutyric acid aminotransferase (GABA-AT): Design, synthesis, biological activities, and mechanistic studies
HK40060666B (en) Method of synthesis
Pan Design, syntheses and mechanistic studies of γ-aminobutyric acid aminotransferase inhibitors
Fan DESIGN, SYNTHESIS, AND EVALUATION OF 5-LIPOXYGENASE INHIBITOR PRODRUGS FOR ALZHEIMER’S DISEASE

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20191010

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20191010

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20200910

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20200929

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20201224

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20210126

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20210218

R150 Certificate of patent or registration of utility model

Ref document number: 6841821

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250