BR112022001346A2 - Derivados de 1,2,4-oxadiazol-5-ona para o tratamen-to de câncer - Google Patents
Derivados de 1,2,4-oxadiazol-5-ona para o tratamen-to de câncerInfo
- Publication number
- BR112022001346A2 BR112022001346A2 BR112022001346A BR112022001346A BR112022001346A2 BR 112022001346 A2 BR112022001346 A2 BR 112022001346A2 BR 112022001346 A BR112022001346 A BR 112022001346A BR 112022001346 A BR112022001346 A BR 112022001346A BR 112022001346 A2 BR112022001346 A2 BR 112022001346A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- c3alkyl
- halogen
- cancer
- c6alkyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
- C07D241/28—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms in which said hetero-bound carbon atoms have double bonds to oxygen, sulfur or nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
derivados de 1,2,4-oxadiazol-5-ona para o tratamento de câncer. a presente invenção refere-se a compostos de fórmula (i) e sais farmaceuticamente aceitáveis dos mesmos, em que a1 é -n= ou -c(r3)=; a2 é -n= ou -ch=; l é -nh-; b1 e b2 são independentemente -n= ou -c(r2b)=; b3 e b4 são independentemente -c(r2b)=; não mais do que um r2b em b1, b2, b3 e b4 é diferente de hidrogênio; r1a é hidrogênio, halogênio, c1-c3alquila (n-alquila) opcionalmente substituída por um r4, ou r1a é -nh2, -nh(c1-c3alquila (n-alquila)), -nh(c(=o)-c1-c2alquila), -n(c1-c3alquila (n-alquila))2, -oc1-c3alquila (n-alquila), c1-c3haloalquila (n-alquila) ou -oc1-c3haloalquila (n-alquila); r1b é hidrogênio, halogênio, c1-c3alquila (n-alquila), -oc1-c3alquila (n-alquila), -nh2, -nh(c1-c3alquila (n-alquila)) ou -n(c1-c3alquila (n-alquila))2; r1a e r1b podem formar juntos um grupo -ch=ch-ch=ch-, em que um ou dois ch não adjacentes são opcionalmente substituídos por n; r2a é halogênio, c1-c6alquila, c1-c6haloalquila, ciclopropila, ciclobutila, -or6, -nhc(=o)-c3-c6cicloalquila, ciclo q, -sf5 ou grupo y (fórmula (y); em que x é um anel carbocíclico de 3 ou 4 membros e r8 é halogênio, ciano, c1-c6alquila, c1-c6haloalquila ou -c1-c6alquil-cn; e em que r2b, r3, r4, r6 e r8 são tais como definidos nas reivindicações; bem como métodos de uso dos compostos para tratar doenças neoplásicas, particularmente, o câncer.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP19188935 | 2019-07-29 | ||
EP20155922 | 2020-02-06 | ||
EP20162120 | 2020-03-10 | ||
PCT/EP2020/071216 WO2021018869A1 (en) | 2019-07-29 | 2020-07-28 | 1,2,4-oxadiazol-5-one derivatives for the treatment of cancer |
Publications (1)
Publication Number | Publication Date |
---|---|
BR112022001346A2 true BR112022001346A2 (pt) | 2022-06-07 |
Family
ID=71842686
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BR112022001346A BR112022001346A2 (pt) | 2019-07-29 | 2020-07-28 | Derivados de 1,2,4-oxadiazol-5-ona para o tratamen-to de câncer |
Country Status (12)
Country | Link |
---|---|
US (1) | US20220402900A1 (pt) |
EP (1) | EP4003983A1 (pt) |
JP (1) | JP2022542683A (pt) |
KR (1) | KR20220054307A (pt) |
CN (1) | CN114174291A (pt) |
AU (1) | AU2020320008A1 (pt) |
BR (1) | BR112022001346A2 (pt) |
CA (1) | CA3147876A1 (pt) |
IL (1) | IL290177A (pt) |
MX (1) | MX2022001125A (pt) |
TW (1) | TW202118759A (pt) |
WO (1) | WO2021018869A1 (pt) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11787775B2 (en) | 2020-07-24 | 2023-10-17 | Genentech, Inc. | Therapeutic compounds and methods of use |
CN115594680A (zh) * | 2021-07-07 | 2023-01-13 | 武汉人福创新药物研发中心有限公司(Cn) | 一种tead抑制剂 |
WO2023049199A1 (en) * | 2021-09-24 | 2023-03-30 | Zeno Management, Inc. | Azole compounds |
WO2023057371A1 (en) * | 2021-10-04 | 2023-04-13 | Basilea Pharmaceutica International Ag, Allschwil | 1,2,4-oxadiazol-5-one derivatives for the treatment of cancer |
WO2023116877A1 (zh) * | 2021-12-24 | 2023-06-29 | 武汉人福创新药物研发中心有限公司 | 作为tead抑制剂的杂环化合物 |
WO2024019562A1 (ko) | 2022-07-21 | 2024-01-25 | 주식회사 바오밥에이바이오 | 헤테로비시클릭 화합물 및 그를 포함하는 약제학적 조성물 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20010108093A (ko) * | 1999-01-13 | 2001-12-07 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | 1-헤테로고리 치환된 디아릴아민 |
US20150157584A1 (en) * | 2012-06-11 | 2015-06-11 | The J. David Gladstone Institutes | Inhibitors of hippo-yap signaling pathway |
WO2015022283A1 (en) | 2013-08-12 | 2015-02-19 | F. Hoffmann-La Roche Ag | Yap-tead inhibitors |
EP2868326A1 (en) | 2013-11-04 | 2015-05-06 | Université Pierre et Marie Curie (Paris 6) | Peptide inhibitors of TEAD/YAP-TAZ interaction |
EP3156404A1 (en) | 2015-10-15 | 2017-04-19 | Inventiva | New compounds inhibitors of the yap/taz-tead interaction and their use in the treatment of malignant mesothelioma |
CA3057261A1 (en) | 2017-04-06 | 2018-10-11 | Inventiva | New compounds inhibitors of the yap/taz-tead interaction and their use in the treatment of malignant mesothelioma |
CA3062294A1 (en) | 2017-05-03 | 2018-11-08 | Vivace Therapeutics, Inc. | Non-fused tricyclic compounds |
US11192865B2 (en) | 2017-08-21 | 2021-12-07 | Vivace Therapeutics, Inc. | Benzosulfonyl compounds |
EP3720430A4 (en) | 2017-12-06 | 2021-05-05 | Vivace Therapeutics, Inc. | BENZOCARBONYL COMPOUNDS |
-
2020
- 2020-07-28 CN CN202080055390.6A patent/CN114174291A/zh active Pending
- 2020-07-28 CA CA3147876A patent/CA3147876A1/en active Pending
- 2020-07-28 JP JP2022505601A patent/JP2022542683A/ja active Pending
- 2020-07-28 TW TW109125462A patent/TW202118759A/zh unknown
- 2020-07-28 KR KR1020227006404A patent/KR20220054307A/ko unknown
- 2020-07-28 WO PCT/EP2020/071216 patent/WO2021018869A1/en active Application Filing
- 2020-07-28 MX MX2022001125A patent/MX2022001125A/es unknown
- 2020-07-28 BR BR112022001346A patent/BR112022001346A2/pt unknown
- 2020-07-28 US US17/629,829 patent/US20220402900A1/en active Pending
- 2020-07-28 AU AU2020320008A patent/AU2020320008A1/en active Pending
- 2020-07-28 EP EP20746968.5A patent/EP4003983A1/en active Pending
-
2022
- 2022-01-27 IL IL290177A patent/IL290177A/en unknown
Also Published As
Publication number | Publication date |
---|---|
EP4003983A1 (en) | 2022-06-01 |
MX2022001125A (es) | 2022-04-18 |
WO2021018869A1 (en) | 2021-02-04 |
KR20220054307A (ko) | 2022-05-02 |
TW202118759A (zh) | 2021-05-16 |
AU2020320008A1 (en) | 2022-03-17 |
IL290177A (en) | 2022-03-01 |
JP2022542683A (ja) | 2022-10-06 |
CA3147876A1 (en) | 2021-02-04 |
US20220402900A1 (en) | 2022-12-22 |
CN114174291A (zh) | 2022-03-11 |
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