OA11388A - Hydroxamic acid derivatives as matrix metalloprotease (MMP) inhibitors. - Google Patents

Hydroxamic acid derivatives as matrix metalloprotease (MMP) inhibitors. Download PDF

Info

Publication number: OA11388A
Authority: OA; OAPI
Prior art keywords: préparation; brs; title compound; lrms; mmol
Prior art date: 1997-12-05

Application number

OA1200000160A

Other languages

English (en)

Inventor

Kevin Neil Dack

Gavin Alistair Whitlock

Original Assignee

Pfizer

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.)

1997-12-05

Filing date

2000-05-31

Publication date

2004-04-14

2000-05-31 Application filed by Pfizer filed Critical Pfizer

2004-04-14 Publication of OA11388A publication Critical patent/OA11388A/en

Links

239000003112 inhibitor Substances 0.000 title claims description 14
239000002253 acid Substances 0.000 title description 28
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title description 4
239000011159 matrix material Substances 0.000 title description 3
102000005741 Metalloproteases Human genes 0.000 title description 2
108010006035 Metalloproteases Proteins 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 325
239000001257 hydrogen Substances 0.000 claims abstract description 36
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
125000005843 halogen group Chemical group 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
229940124761 MMP inhibitor Drugs 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000005842 heteroatom Chemical group 0.000 claims abstract description 7
208000017520 skin disease Diseases 0.000 claims abstract description 7
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125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
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238000000034 method Methods 0.000 claims description 171
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 144
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 142
239000000203 mixture Substances 0.000 claims description 85
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 64
-1 -136- thienyl Chemical group 0.000 claims description 59
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 32
239000002904 solvent Substances 0.000 claims description 27
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 24
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VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 claims description 15
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 14
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JRIUEEGXFJPYTG-UHFFFAOYSA-N n-hydroxy-2-[4-[4-[3-(2-methoxyethoxy)phenyl]-3-methylphenyl]piperidin-1-yl]sulfonyl-2-methylpropanamide Chemical compound COCCOC1=CC=CC(C=2C(=CC(=CC=2)C2CCN(CC2)S(=O)(=O)C(C)(C)C(=O)NO)C)=C1 JRIUEEGXFJPYTG-UHFFFAOYSA-N 0.000 claims 1
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229910000368 zinc sulfate Inorganic materials 0.000 description 1
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 0.000 description 1

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
- C07D401/10—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 carbon chain containing aromatic rings
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- C07D405/10—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 linked by a carbon chain containing aromatic rings
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Physical Education & Sports Medicine (AREA)
Pain & Pain Management (AREA)
Vascular Medicine (AREA)
Oncology (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Enzymes And Modification Thereof (AREA)
Cosmetics (AREA)

OA1200000160A 1997-12-05 2000-05-31 Hydroxamic acid derivatives as matrix metalloprotease (MMP) inhibitors. OA11388A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9725782.8A GB9725782D0 (en)	1997-12-05	1997-12-05	Therapeutic agents

Publications (1)

Publication Number	Publication Date
OA11388A true OA11388A (en)	2004-04-14

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ID=10823173

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Application Number	Title	Priority Date	Filing Date
OA1200000160A OA11388A (en)	1997-12-05	2000-05-31	Hydroxamic acid derivatives as matrix metalloprotease (MMP) inhibitors.

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US (1)	US6495568B1 (no)
EP (1)	EP1036062B1 (no)
JP (1)	JP3445242B2 (no)
KR (1)	KR100372990B1 (no)
CN (1)	CN1281433A (no)
AP (1)	AP930A (no)
AR (1)	AR016429A1 (no)
AT (1)	ATE257151T1 (no)
AU (1)	AU741859B2 (no)
BG (1)	BG104506A (no)
BR (1)	BR9813360A (no)
CA (1)	CA2312935C (no)
CZ (1)	CZ20002037A3 (no)
DE (1)	DE69820906T2 (no)
DK (1)	DK1036062T3 (no)
DZ (1)	DZ2666A1 (no)
EA (1)	EA002882B1 (no)
ES (1)	ES2212373T3 (no)
GB (1)	GB9725782D0 (no)
GT (1)	GT199800189A (no)
HR (1)	HRP20000373A2 (no)
HU (1)	HUP0100845A3 (no)
ID (1)	ID24626A (no)
IL (1)	IL136300A0 (no)
IS (1)	IS5503A (no)
MA (1)	MA26571A1 (no)
NO (1)	NO20002826L (no)
NZ (1)	NZ504421A (no)
OA (1)	OA11388A (no)
PA (1)	PA8463501A1 (no)
PE (1)	PE133999A1 (no)
PL (1)	PL341031A1 (no)
PT (1)	PT1036062E (no)
SK (1)	SK7822000A3 (no)
TN (1)	TNSN98216A1 (no)
TR (1)	TR200001611T2 (no)
UA (1)	UA52791C2 (no)
UY (2)	UY25282A1 (no)
WO (1)	WO1999029667A1 (no)
YU (1)	YU32100A (no)
ZA (1)	ZA9811112B (no)

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1997
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1998
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- 1998-10-09 KR KR10-2000-7006098A patent/KR100372990B1/ko not_active Expired - Fee Related
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Publication number	Publication date
EP1036062A1 (en)	2000-09-20
PL341031A1 (en)	2001-03-26
YU32100A (sh)	2003-02-28
HUP0100845A3 (en)	2002-12-28
HUP0100845A2 (hu)	2001-08-28
KR20010024688A (ko)	2001-03-26
PA8463501A1 (es)	2000-09-29
PE133999A1 (es)	2000-01-10
EP1036062B1 (en)	2004-01-02
DZ2666A1 (fr)	2003-03-22
UY25282A1 (es)	1999-07-19
AP930A (en)	2001-01-26
AU1230199A (en)	1999-06-28
WO1999029667A1 (en)	1999-06-17
CN1281433A (zh)	2001-01-24
UY25280A1 (es)	2001-01-31
UA52791C2 (uk)	2003-01-15
SK7822000A3 (en)	2001-12-03
MA26571A1 (fr)	2004-12-20
BG104506A (bg)	2001-01-31
AU741859B2 (en)	2001-12-13
US6495568B1 (en)	2002-12-17
EA002882B1 (ru)	2002-10-31
CA2312935C (en)	2006-03-14
DE69820906T2 (de)	2004-07-15
ES2212373T3 (es)	2004-07-16
DK1036062T3 (da)	2004-04-05
GB9725782D0 (en)	1998-02-04
EA200000481A1 (ru)	2000-12-25
NZ504421A (en)	2002-02-01
ATE257151T1 (de)	2004-01-15
TNSN98216A1 (fr)	2005-03-15
PT1036062E (pt)	2004-04-30
AP9801412A0 (en)	1998-12-31
BR9813360A (pt)	2000-10-17
TR200001611T2 (tr)	2000-10-23
ZA9811112B (en)	2000-06-05
JP3445242B2 (ja)	2003-09-08
CA2312935A1 (en)	1999-06-17
HRP20000373A2 (en)	2000-12-31
ID24626A (id)	2000-07-27
KR100372990B1 (ko)	2003-02-25
NO20002826L (no)	2000-07-26
IS5503A (is)	2000-05-19
AR016429A1 (es)	2001-07-04
GT199800189A (es)	2000-05-18
DE69820906D1 (de)	2004-02-05
JP2001525396A (ja)	2001-12-11
IL136300A0 (en)	2001-05-20
NO20002826D0 (no)	2000-06-02
CZ20002037A3 (cs)	2001-09-12

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