PT3877395T - Processo industrial para a preparação de estetrol de pureza elevada - Google Patents

Processo industrial para a preparação de estetrol de pureza elevada

Info

Publication number: PT3877395T
Authority: PT; Portugal
Prior art keywords: estetrol; preparation; high purity; industrial process; industrial
Prior art date: 2019-09-03

Application number

PT207683988T

Other languages

English (en)

Original Assignee

Richter Gedeon Nyrt

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.)

2019-09-03

Filing date

2020-09-02

Publication date

2023-02-02

2020-09-02 Application filed by Richter Gedeon Nyrt filed Critical Richter Gedeon Nyrt

2023-02-02 Publication of PT3877395T publication Critical patent/PT3877395T/pt

Links

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/566—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol having an oxo group in position 17, e.g. estrone
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/30—Oestrogens
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0074—Esters
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Immunology (AREA)
Gynecology & Obstetrics (AREA)
Dermatology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Diabetes (AREA)
Transplantation (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

PT207683988T 2019-09-03 2020-09-02 Processo industrial para a preparação de estetrol de pureza elevada PT3877395T (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU1900315A HU231240B1 (hu)	2019-09-03	2019-09-03	Ipari eljárás nagytisztaságú ösztetrol hatóanyag előállítására

Publications (1)

Publication Number	Publication Date
PT3877395T true PT3877395T (pt)	2023-02-02

Family

ID=89992977

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PT207683988T PT3877395T (pt)	2019-09-03	2020-09-02	Processo industrial para a preparação de estetrol de pureza elevada

Country Status (33)

Country	Link
US (1)	US11633406B2 (pt)
EP (1)	EP3877395B1 (pt)
JP (1)	JP7265087B2 (pt)
KR (1)	KR102871606B1 (pt)
CN (1)	CN114302889B (pt)
AU (1)	AU2020343497B2 (pt)
CA (1)	CA3147815C (pt)
CL (1)	CL2022000492A1 (pt)
CO (1)	CO2022003769A2 (pt)
CU (1)	CU24692B1 (pt)
DK (1)	DK3877395T3 (pt)
EC (1)	ECSP22022403A (pt)
ES (1)	ES2855923T3 (pt)
FI (1)	FI3877395T3 (pt)
GE (1)	GEP20247626B (pt)
HR (1)	HRP20230230T1 (pt)
HU (2)	HU231240B1 (pt)
IL (1)	IL290973B2 (pt)
JO (1)	JOP20220041A1 (pt)
LT (1)	LT3877395T (pt)
MA (1)	MA54200B1 (pt)
MD (1)	MD3877395T2 (pt)
MX (1)	MX2022002603A (pt)
MY (1)	MY206905A (pt)
NZ (1)	NZ786568A (pt)
PE (1)	PE20221418A1 (pt)
PH (1)	PH12022550388A1 (pt)
PL (1)	PL3877395T3 (pt)
PT (1)	PT3877395T (pt)
RS (1)	RS63966B1 (pt)
SI (1)	SI3877395T1 (pt)
WO (1)	WO2021044302A1 (pt)
ZA (1)	ZA202203557B (pt)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN114514237B (zh) *	2019-09-27	2024-07-26	工业化学有限公司	用于制备(15α,16α,17β)-雌-1,3,5(10)-三烯-3,15,16,17-四醇(雌四醇)的工艺及所述工艺的中间体
GB2626482B (en) *	2021-10-01	2025-04-30	Ind Chimica Srl	Process for preparing (15alpha,16alpha,17beta)-estra-1,3,5-(10)-triene-3,15,16,17-tetrol(estetrol) monohydrate
CN120958008A (zh) *	2023-02-02	2025-11-14	工业化学有限公司	制备(15α,16α,17β)-雌甾-1,3,5(10)-三烯-3,15,16,17-四醇（雌四醇）一水合物的方法
CN117088928B (zh) *	2023-08-16	2025-09-09	湖北共同甾体药物研究院有限公司	用于制备高纯度雌四醇的工艺
CN119569803B (zh) *	2023-09-05	2025-09-16	秦皇岛紫竹药业有限公司	一种制备高纯度雌四醇的方法
HUP2400151A1 (hu)	2024-02-28	2025-09-28	Richter Gedeon Nyrt	Ösztetrol-monohidrát kristályosítási eljárás

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1260225A1 (en)	2001-05-18	2002-11-27	Pantarhei Bioscience B.V.	A pharmaceutical composition for use in hormone replacement therapy
DE60217324T2 (de)	2001-05-18	2007-04-26	Pantarhei Bioscience B.V.	Pharmazeutische zusammensetzung für die hormonersatztherapie
EP1390041B1 (en)	2001-05-23	2009-11-25	Pantarhei Bioscience B.V.	Drug delivery system comprising a tetrahydroxylated estrogen for use in hormonal contraception
US7732430B2 (en)	2001-05-23	2010-06-08	Pantarhei Bioscience B.V.	Drug delivery system comprising a tetrahydroxilated estrogen for use in hormonal contraception
ATE347365T1 (de)	2001-11-15	2006-12-15	Pantarhei Bioscience Bv	Verwendung von öestrogen in kombination mit progestogen für die hormonsubstitutions-therapie
CA2489270C (en)	2002-06-11	2012-08-07	Pantarhei Bioscience B.V.	A method of treating human skin and a skin care composition for use in such a method
AU2003274946A1 (en)	2002-06-11	2003-12-22	Pantarhei Bioscience B.V.	Method of treating or preventing immune mediated disorders and pharmaceutical formulation for use therein
US9034854B2 (en)	2002-07-12	2015-05-19	Pantarhei Bioscience B.V.	Pharmaceutical composition comprising estetrol derivatives for use in cancer therapy
US8987240B2 (en)	2002-10-23	2015-03-24	Pantarhei Bioscience B.V.	Pharmaceutical compositions comprising estetrol derivatives for use in cancer therapy
AU2003279624A1 (en) *	2002-11-08	2004-06-07	Pantarhei Bioscience B.V.	Synthesis of estetrol via estrone derived steroids
EP1971344B1 (en)	2006-01-09	2010-09-22	Pantarhei Bioscience B.V.	A method of treating an acute vascular disorder
CN101583363B (zh)	2007-01-08	2013-08-21	潘塔希生物科学股份有限公司	治疗或预防雌性哺乳动物不育症的方法和此类方法中使用的药物试剂盒
EP2383279A1 (en)	2011-07-19	2011-11-02	Pantarhei Bioscience B.V.	Process for the preparation of estetrol
BR112014003113A2 (pt)	2011-08-11	2017-03-14	Estetra Sprl	método de contracepção de emergência em uma fêmea mamífero
EP2764008B1 (en)	2011-10-07	2016-08-17	Estetra S.P.R.L.	Process for the production of estetrol
EP2653163A1 (en)	2012-04-19	2013-10-23	Université de Liège	Estrogenic components for use in the treatment of neurological disorders
WO2013034780A2 (en)	2012-12-20	2013-03-14	Crystal Pharma, S.A.U.	Process for the preparation of estetrol and related compounds
EP3046928B1 (en) *	2013-09-18	2017-02-08	Crystal Pharma, S.A.U.	Process for the preparation of estetrol
HUE035848T2 (en)	2013-12-12	2018-05-28	Donesta Bioscience B V	Solid dispensing unit containing an estetrol compound in the mouth
WO2016203044A1 (en)	2015-06-18	2016-12-22	Mithra Pharmaceuticals S.A.	Orodispersible tablet containing estetrol
LT3310345T (lt)	2015-06-18	2021-06-25	Estetra Sprl	Burnoje disperguojama tabletė, turinti estetrolio
NZ737945A (en)	2015-06-18	2023-06-30	Estetra Sprl	Orodispersible dosage unit containing an estetrol component
CA3178291A1 (en)	2016-08-05	2018-04-12	Estetra Srl	Method for the management of dysmenorrhea and menstrual pain
CA3041016C (en)	2016-10-28	2023-09-05	Estetra Sprl	Method for the management of dysmenorrhea and menstrual pain
WO2019025031A1 (en)	2017-08-01	2019-02-07	Pantarhei Oncology B.V.	ADJUVANT TREATMENT FOR USE IN THE TREATMENT OF PROSTATE CANCER
UA126746C2 (uk)	2018-02-07	2023-01-18	Естетра Спрл	Композиція контрацептива зі зниженими ефектами щодо серцево-судинної системи
CN114514237B (zh)	2019-09-27	2024-07-26	工业化学有限公司	用于制备(15α,16α,17β)-雌-1,3,5(10)-三烯-3,15,16,17-四醇(雌四醇)的工艺及所述工艺的中间体

2019
- 2019-09-03 HU HU1900315A patent/HU231240B1/hu unknown
2020
- 2020-09-02 DK DK20768398.8T patent/DK3877395T3/da active
- 2020-09-02 RS RS20230112A patent/RS63966B1/sr unknown
- 2020-09-02 ES ES20768398T patent/ES2855923T3/es active Active
- 2020-09-02 HR HRP20230230TT patent/HRP20230230T1/hr unknown
- 2020-09-02 SI SI202030156T patent/SI3877395T1/sl unknown
- 2020-09-02 KR KR1020227010919A patent/KR102871606B1/ko active Active
- 2020-09-02 CA CA3147815A patent/CA3147815C/en active Active
- 2020-09-02 MA MA54200A patent/MA54200B1/fr unknown
- 2020-09-02 PL PL20768398.8T patent/PL3877395T3/pl unknown
- 2020-09-02 HU HUE20768398A patent/HUE061427T2/hu unknown
- 2020-09-02 GE GEAP202015920A patent/GEP20247626B/en unknown
- 2020-09-02 AU AU2020343497A patent/AU2020343497B2/en active Active
- 2020-09-02 US US17/639,206 patent/US11633406B2/en active Active
- 2020-09-02 WO PCT/IB2020/058148 patent/WO2021044302A1/en not_active Ceased
- 2020-09-02 FI FIEP20768398.8T patent/FI3877395T3/fi active
- 2020-09-02 IL IL290973A patent/IL290973B2/en unknown
- 2020-09-02 MX MX2022002603A patent/MX2022002603A/es unknown
- 2020-09-02 MD MDE20210894T patent/MD3877395T2/ro unknown
- 2020-09-02 PT PT207683988T patent/PT3877395T/pt unknown
- 2020-09-02 PE PE2022000348A patent/PE20221418A1/es unknown
- 2020-09-02 CU CU2022000013A patent/CU24692B1/es unknown
- 2020-09-02 CN CN202080061521.1A patent/CN114302889B/zh active Active
- 2020-09-02 MY MYPI2022000866A patent/MY206905A/en unknown
- 2020-09-02 EP EP20768398.8A patent/EP3877395B1/en active Active
- 2020-09-02 JP JP2022511285A patent/JP7265087B2/ja active Active
- 2020-09-02 NZ NZ786568A patent/NZ786568A/en unknown
- 2020-09-02 LT LTEPPCT/IB2020/058148T patent/LT3877395T/lt unknown
2022
- 2022-02-21 JO JOP/2022/0041A patent/JOP20220041A1/ar unknown
- 2022-02-28 CL CL2022000492A patent/CL2022000492A1/es unknown
- 2022-03-24 EC ECSENADI202222403A patent/ECSP22022403A/es unknown
- 2022-03-28 ZA ZA2022/03557A patent/ZA202203557B/en unknown
- 2022-03-29 CO CONC2022/0003769A patent/CO2022003769A2/es unknown
- 2022-09-02 PH PH1/2022/550388A patent/PH12022550388A1/en unknown

Also Published As

Publication number	Publication date
EP3877395A1 (en)	2021-09-15
KR102871606B1 (ko)	2025-10-16
CA3147815A1 (en)	2021-03-11
HU231240B1 (hu)	2022-04-28
AU2020343497B2 (en)	2023-02-02
HUP1900315A1 (hu)	2021-03-29
JP7265087B2 (ja)	2023-04-25
HUE061427T2 (hu)	2023-07-28
GEP20247626B (en)	2024-05-27
CU20220013A7 (es)	2022-10-11
CO2022003769A2 (es)	2022-04-19
HRP20230230T1 (hr)	2023-04-14
MA54200B1 (fr)	2023-02-28
US11633406B2 (en)	2023-04-25
MY206905A (en)	2025-01-15
RS63966B1 (sr)	2023-03-31
JP2022546016A (ja)	2022-11-02
CN114302889B (zh)	2023-08-29
FI3877395T3 (fi)	2023-03-18
DK3877395T3 (da)	2023-03-06
MA54200A (fr)	2022-04-27
ECSP22022403A (es)	2022-04-29
US20220296609A1 (en)	2022-09-22
SI3877395T1 (sl)	2023-03-31
PL3877395T3 (pl)	2023-05-08
JOP20220041A1 (ar)	2023-01-30
EP3877395B1 (en)	2022-12-07
AU2020343497A1 (en)	2022-04-14
IL290973B2 (en)	2023-11-01
CU24692B1 (es)	2024-01-10
MX2022002603A (es)	2022-03-25
CN114302889A (zh)	2022-04-08
ES2855923T3 (es)	2023-04-28
ES2855923T1 (es)	2021-09-24
CL2022000492A1 (es)	2023-03-10
PE20221418A1 (es)	2022-09-20
IL290973A (en)	2022-05-01
KR20220071206A (ko)	2022-05-31
WO2021044302A1 (en)	2021-03-11
ZA202203557B (en)	2022-11-30
IL290973B1 (en)	2023-07-01
LT3877395T (lt)	2023-02-27
BR112022003254A2 (pt)	2022-05-17
PH12022550388A1 (en)	2024-01-29
MD3877395T2 (ro)	2023-05-31
NZ786568A (en)	2026-01-30
CA3147815C (en)	2023-03-28

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