FR2757855B1 - Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent - Google Patents

Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent

Info

Publication number
FR2757855B1
FR2757855B1 FR9616206A FR9616206A FR2757855B1 FR 2757855 B1 FR2757855 B1 FR 2757855B1 FR 9616206 A FR9616206 A FR 9616206A FR 9616206 A FR9616206 A FR 9616206A FR 2757855 B1 FR2757855 B1 FR 2757855B1
Authority
FR
France
Prior art keywords
preparation
pharmaceutical compositions
compositions containing
transferase inhibitors
farnesyl transferase
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.)
Expired - Fee Related
Application number
FR9616206A
Other languages
English (en)
French (fr)
Other versions
FR2757855A1 (fr
Inventor
Jean Dominique Bourzat
Alain Commercon
Norbert Dereu
Patrick Mailliet
Thompson Fabienne Sounigo
Jean Paul Martin
Marc Capet
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aventis Pharma SA
Original Assignee
Rhone Poulenc Rorer SA
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 Rhone Poulenc Rorer SA filed Critical Rhone Poulenc Rorer SA
Priority to FR9616206A priority Critical patent/FR2757855B1/fr
Priority to PE1997001089A priority patent/PE28199A1/es
Priority to ES97953000T priority patent/ES2172033T3/es
Priority to EP97953000A priority patent/EP0948483B1/fr
Priority to AT97953000T priority patent/ATE214367T1/de
Priority to YU30299A priority patent/YU30299A/sh
Priority to KR1019997005966A priority patent/KR20000062391A/ko
Priority to SI9730310T priority patent/SI0948483T1/xx
Priority to DK97953000T priority patent/DK0948483T3/da
Priority to CZ992335A priority patent/CZ233599A3/cs
Priority to TR1999/01502T priority patent/TR199901502T2/xx
Priority to DE69711081T priority patent/DE69711081T2/de
Priority to CA002275943A priority patent/CA2275943A1/fr
Priority to HU0001747A priority patent/HUP0001747A3/hu
Priority to PCT/FR1997/002407 priority patent/WO1998029390A1/fr
Priority to BR9714498A priority patent/BR9714498A/pt
Priority to AU56694/98A priority patent/AU741921B2/en
Priority to PL97334345A priority patent/PL334345A1/xx
Priority to PT97953000T priority patent/PT948483E/pt
Priority to EA199900608A priority patent/EA002114B1/ru
Priority to IL13045397A priority patent/IL130453A0/xx
Priority to IDW990618A priority patent/ID22922A/id
Priority to JP52968698A priority patent/JP2001509147A/ja
Priority to SK883-99A priority patent/SK88399A3/sk
Priority to NZ336042A priority patent/NZ336042A/xx
Priority to TNTNSN97214A priority patent/TNSN97214A1/fr
Priority to MA24915A priority patent/MA26460A1/fr
Priority to DZ970239A priority patent/DZ2389A1/xx
Priority to US08/999,408 priority patent/US6013662A/en
Priority to CO97075391A priority patent/CO4920252A1/es
Priority to ZA9711734A priority patent/ZA9711734B/xx
Priority to ARP970106263A priority patent/AR008950A1/es
Priority to UY24832A priority patent/UY24832A1/es
Publication of FR2757855A1 publication Critical patent/FR2757855A1/fr
Application granted granted Critical
Publication of FR2757855B1 publication Critical patent/FR2757855B1/fr
Priority to NO993225A priority patent/NO993225L/no
Priority to US09/346,303 priority patent/US6218406B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/12—Heterocyclic 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 linked by a chain containing hetero atoms as chain links
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/72—4,7-Endo-alkylene-iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/04—Heterocyclic 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
    • 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
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic 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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
FR9616206A 1996-12-30 1996-12-30 Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent Expired - Fee Related FR2757855B1 (fr)

Priority Applications (35)

Application Number Priority Date Filing Date Title
FR9616206A FR2757855B1 (fr) 1996-12-30 1996-12-30 Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent
PE1997001089A PE28199A1 (es) 1996-12-30 1997-12-03 Nuevos inhibidores de farnesil transferasa, su preparacion, las composiciones farmaceuticas que las contienen y su utilizacion para la preparacion de medicamentos
IL13045397A IL130453A0 (en) 1996-12-30 1997-12-23 Farnesyl transferase inhibitors
AT97953000T ATE214367T1 (de) 1996-12-30 1997-12-23 Farnesyl transferase inhibitoren
YU30299A YU30299A (sh) 1996-12-30 1997-12-23 Novi inhibitori farnezil-transferaze,njihovo dobijanje, farmaceutske smeše koje ih sadrže i njihova primena za dobijanje lekova
KR1019997005966A KR20000062391A (ko) 1996-12-30 1997-12-23 파네실 트랜스퍼라제 억제제
SI9730310T SI0948483T1 (en) 1996-12-30 1997-12-23 Farnesyl transferase inhibitors
DK97953000T DK0948483T3 (da) 1996-12-30 1997-12-23 Farnesyltransferaseinhibitorer
CZ992335A CZ233599A3 (cs) 1996-12-30 1997-12-23 Inhibitory farnesyltransferázy, způsob jejich přípravy a farmaceutické prostředky, které je obsahují
TR1999/01502T TR199901502T2 (xx) 1996-12-30 1997-12-23 Farnesil transferaz� inhibit�rleri.
JP52968698A JP2001509147A (ja) 1996-12-30 1997-12-23 ファルネシルトランスフェラーゼ阻害剤
CA002275943A CA2275943A1 (fr) 1996-12-30 1997-12-23 Inhibiteurs de farnesyle transferase
HU0001747A HUP0001747A3 (en) 1996-12-30 1997-12-23 1h-benzo[+]isoindole derivatives as farnesyl transferase inhibitor, process for producing them and use of them for process pharmaceutical compositions
PCT/FR1997/002407 WO1998029390A1 (fr) 1996-12-30 1997-12-23 Inhibiteurs de farnesyle transferase
BR9714498A BR9714498A (pt) 1996-12-30 1997-12-23 composição farmacêutica, e, associação de um produto.
AU56694/98A AU741921B2 (en) 1996-12-30 1997-12-23 Farnesyl transferase inhibitors
PL97334345A PL334345A1 (en) 1996-12-30 1997-12-23 Novel farnesil transferase inhibitors, their production, pharmaceutic compositions containing them and their application in production drugs
PT97953000T PT948483E (pt) 1996-12-30 1997-12-23 Inibidores da farnesil-transferase
ES97953000T ES2172033T3 (es) 1996-12-30 1997-12-23 Inhibidores de farnesil transferasa.
IDW990618A ID22922A (enExample) 1996-12-30 1997-12-23
EP97953000A EP0948483B1 (fr) 1996-12-30 1997-12-23 Inhibiteurs de farnesyle transferase
DE69711081T DE69711081T2 (de) 1996-12-30 1997-12-23 Farnesyl transferase inhibitoren
SK883-99A SK88399A3 (en) 1996-12-30 1997-12-23 Farnesyl transferase inhibitors
NZ336042A NZ336042A (en) 1996-12-30 1997-12-23 Farnesyl transferase inhibitors
EA199900608A EA002114B1 (ru) 1996-12-30 1997-12-23 Новые ингибиторы фарнезилтрансферазы, способы их получения, содержащие их фармацевтические композиции и их применение для получения медикаментов
TNTNSN97214A TNSN97214A1 (fr) 1996-12-30 1997-12-26 Nouveaux inhibiteurs de farnesyle transferase, leur preparation, les compositions pharmaceutiques qui les contiennent et leur utilisation pour la preparation de medicaments
MA24915A MA26460A1 (fr) 1996-12-30 1997-12-26 Nouveaux inhibiteurs de farnesyle transferase, leur preparation, les compositions pharmaceutiques qui les contiennent.
DZ970239A DZ2389A1 (fr) 1996-12-30 1997-12-27 Nouveaux inhibiteurs de farnesyle transférase leurpréparation les compositions pharmaceutiques qui les contiennent et leur utilisation pour la préparation de médicaments
CO97075391A CO4920252A1 (es) 1996-12-30 1997-12-29 Nuevos derivados de benzoperhidroisoindol inhibidores de farnesil transferasa, su preparacion, las composiciones farmaceuticas que los contienen
US08/999,408 US6013662A (en) 1996-12-30 1997-12-29 Farnesyl transferase inhibitors, their preparation, the pharmaceutical compositions which contain them and their use in the preparation of medicaments
UY24832A UY24832A1 (es) 1996-12-30 1997-12-30 Nuevos compuestos derivados del benzoperhidroisoindol, útiles como inhibidores de la farnesil transferasa, procedimiento para prepararlos, los intermediarios de sintesis y su preparación, las composiciones farmacéuticas que contienen dichos derivados
ARP970106263A AR008950A1 (es) 1996-12-30 1997-12-30 Nuevos compuestos derivados del benzoperhidroisoindol, procedimiento para prepararlos, los intermediarios de sintesis y los procedimientos paraprepararlos, las composiciones farmaceuticas que los contienen, la utilizacion de dichos compuestos para preparar dichas composiciones y las composiciones
ZA9711734A ZA9711734B (en) 1996-12-30 1997-12-30 Novel farnesyl transferase inhibitors, their preparation, the pharmaceutical compositions which contain them and their use in the preparation of medicaments.
NO993225A NO993225L (no) 1996-12-30 1999-06-29 Farnesyltransferaseinhibitorer
US09/346,303 US6218406B1 (en) 1996-12-30 1999-07-02 Farnesyl transferase inhibitors, their preparation, the pharmaceutical compositions which contain them and their use in the preparation of medicaments

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR9616206A FR2757855B1 (fr) 1996-12-30 1996-12-30 Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent

Publications (2)

Publication Number Publication Date
FR2757855A1 FR2757855A1 (fr) 1998-07-03
FR2757855B1 true FR2757855B1 (fr) 1999-01-29

Family

ID=9499293

Family Applications (1)

Application Number Title Priority Date Filing Date
FR9616206A Expired - Fee Related FR2757855B1 (fr) 1996-12-30 1996-12-30 Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent

Country Status (32)

Country Link
EP (1) EP0948483B1 (enExample)
JP (1) JP2001509147A (enExample)
KR (1) KR20000062391A (enExample)
AR (1) AR008950A1 (enExample)
AT (1) ATE214367T1 (enExample)
AU (1) AU741921B2 (enExample)
BR (1) BR9714498A (enExample)
CA (1) CA2275943A1 (enExample)
CO (1) CO4920252A1 (enExample)
CZ (1) CZ233599A3 (enExample)
DE (1) DE69711081T2 (enExample)
DK (1) DK0948483T3 (enExample)
DZ (1) DZ2389A1 (enExample)
EA (1) EA002114B1 (enExample)
ES (1) ES2172033T3 (enExample)
FR (1) FR2757855B1 (enExample)
HU (1) HUP0001747A3 (enExample)
ID (1) ID22922A (enExample)
IL (1) IL130453A0 (enExample)
MA (1) MA26460A1 (enExample)
NO (1) NO993225L (enExample)
NZ (1) NZ336042A (enExample)
PE (1) PE28199A1 (enExample)
PL (1) PL334345A1 (enExample)
PT (1) PT948483E (enExample)
SK (1) SK88399A3 (enExample)
TN (1) TNSN97214A1 (enExample)
TR (1) TR199901502T2 (enExample)
UY (1) UY24832A1 (enExample)
WO (1) WO1998029390A1 (enExample)
YU (1) YU30299A (enExample)
ZA (1) ZA9711734B (enExample)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2787327B1 (fr) * 1998-12-21 2003-01-17 Aventis Pharma Sa Compositions contenant des inhibiteurs de farnesyle transferase
FR2796641B1 (fr) * 1999-07-22 2001-09-21 Aventis Pharma Sa Nouveau procede de preparation de composes benzoperhydroisoindole
FR2796640A1 (fr) * 1999-07-22 2001-01-26 Aventis Pharma Sa Nouveaux inhibiteurs de farnesyle transferase, leur preparation, les compositions pharmaceutiques qui les contiennent et leur utilisation pour la preparation de medicaments
FR2845994B1 (fr) * 2002-10-18 2006-05-19 Servier Lab Nouveaux derives de benzo[e][1,4]oxazino[3,2-g]isoindole substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
WO2005089504A2 (en) * 2004-03-18 2005-09-29 The Brigham And Women's Hospital, Inc. Methods for the treatment of synucleinopathies
WO2024229406A1 (en) 2023-05-04 2024-11-07 Revolution Medicines, Inc. Combination therapy for a ras related disease or disorder
TW202530228A (zh) 2023-10-12 2025-08-01 美商銳新醫藥公司 Ｒａｓ抑制劑
WO2025171296A1 (en) 2024-02-09 2025-08-14 Revolution Medicines, Inc. Ras inhibitors
TW202547461A (zh) 2024-05-17 2025-12-16 美商銳新醫藥公司 Ｒａｓ抑制劑
WO2025255438A1 (en) 2024-06-07 2025-12-11 Revolution Medicines, Inc. Methods of treating a ras protein-related disease or disorder
WO2025265060A1 (en) 2024-06-21 2025-12-26 Revolution Medicines, Inc. Therapeutic compositions and methods for managing treatment-related effects
WO2026006747A1 (en) 2024-06-28 2026-01-02 Revolution Medicines, Inc. Ras inhibitors
WO2026015825A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Use of ras inhibitor for treating pancreatic cancer
WO2026015801A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026015796A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026015790A1 (en) 2024-07-12 2026-01-15 Revolution Medicines, Inc. Methods of treating a ras related disease or disorder
WO2026050446A1 (en) 2024-08-29 2026-03-05 Revolution Medicines, Inc. Ras inhibitors

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0730605A1 (en) * 1993-11-05 1996-09-11 Warner-Lambert Company Substituted di- and tripeptide inhibitors of protein:farnesyl transferase
FR2736641B1 (fr) * 1995-07-10 1997-08-22 Rhone Poulenc Rorer Sa Nouveaux inhibiteurs de farnesyl transferase, leur preparation et les compositions pharmaceutiques qui les contiennent

Also Published As

Publication number Publication date
AR008950A1 (es) 2000-02-23
HUP0001747A3 (en) 2000-10-30
EP0948483A1 (fr) 1999-10-13
DE69711081T2 (de) 2002-08-01
ID22922A (enExample) 1999-12-16
NO993225D0 (no) 1999-06-29
IL130453A0 (en) 2000-06-01
HUP0001747A2 (hu) 2000-09-28
EP0948483B1 (fr) 2002-03-13
DK0948483T3 (da) 2002-07-01
TNSN97214A1 (fr) 2005-03-15
YU30299A (sh) 2002-03-18
NZ336042A (en) 2000-12-22
CZ233599A3 (cs) 1999-09-15
CO4920252A1 (es) 2000-05-29
MA26460A1 (fr) 2004-12-20
ES2172033T3 (es) 2002-09-16
PE28199A1 (es) 1999-06-05
JP2001509147A (ja) 2001-07-10
ZA9711734B (en) 1998-06-25
EA002114B1 (ru) 2001-12-24
EA199900608A1 (ru) 2000-02-28
ATE214367T1 (de) 2002-03-15
UY24832A1 (es) 2001-08-27
NO993225L (no) 1999-08-24
AU741921B2 (en) 2001-12-13
TR199901502T2 (xx) 1999-09-21
CA2275943A1 (fr) 1998-07-09
PT948483E (pt) 2002-08-30
BR9714498A (pt) 2000-03-21
FR2757855A1 (fr) 1998-07-03
PL334345A1 (en) 2000-02-28
DE69711081D1 (de) 2002-04-18
WO1998029390A1 (fr) 1998-07-09
DZ2389A1 (fr) 2002-12-28
AU5669498A (en) 1998-07-31
KR20000062391A (ko) 2000-10-25
SK88399A3 (en) 2000-05-16

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