NO305973B1 - Anvendelse av quinolin og quinazolinderivater, forbindelsene som sådanne samt antiinflammatoriske midler inneholdende forbindelsene - Google Patents

Anvendelse av quinolin og quinazolinderivater, forbindelsene som sådanne samt antiinflammatoriske midler inneholdende forbindelsene

Info

Publication number
NO305973B1
NO305973B1 NO931482A NO931482A NO305973B1 NO 305973 B1 NO305973 B1 NO 305973B1 NO 931482 A NO931482 A NO 931482A NO 931482 A NO931482 A NO 931482A NO 305973 B1 NO305973 B1 NO 305973B1
Authority
NO
Norway
Prior art keywords
compounds
quinoline
inflammatory agents
agents containing
quinazoline derivatives
Prior art date
Application number
NO931482A
Other languages
English (en)
Norwegian (no)
Other versions
NO931482L (no
NO931482D0 (no
Inventor
Takashi Sohda
Haruhiko Makino
Atsuo Baba
Original Assignee
Takeda Chemical Industries Ltd
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 Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd
Publication of NO931482D0 publication Critical patent/NO931482D0/no
Publication of NO931482L publication Critical patent/NO931482L/no
Publication of NO305973B1 publication Critical patent/NO305973B1/no

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C07D239/76—N-oxides
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • 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
    • 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
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D413/10—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 linked by a carbon chain containing aromatic 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Rheumatology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
NO931482A 1992-04-24 1993-04-22 Anvendelse av quinolin og quinazolinderivater, forbindelsene som sådanne samt antiinflammatoriske midler inneholdende forbindelsene NO305973B1 (no)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP10642492 1992-04-24
JP12188792 1992-05-14
JP28586592 1992-10-23
JP3795293 1993-02-26

Publications (3)

Publication Number Publication Date
NO931482D0 NO931482D0 (no) 1993-04-22
NO931482L NO931482L (no) 1993-10-25
NO305973B1 true NO305973B1 (no) 1999-08-30

Family

ID=27460501

Family Applications (1)

Application Number Title Priority Date Filing Date
NO931482A NO305973B1 (no) 1992-04-24 1993-04-22 Anvendelse av quinolin og quinazolinderivater, forbindelsene som sådanne samt antiinflammatoriske midler inneholdende forbindelsene

Country Status (14)

Country Link
US (1) US5948782A (is)
EP (1) EP0567107B1 (is)
KR (1) KR940005273A (is)
CN (1) CN1079222A (is)
AT (1) ATE209199T1 (is)
AU (1) AU656069B2 (is)
CA (1) CA2094774A1 (is)
DE (1) DE69331171T2 (is)
FI (1) FI931855A (is)
HU (2) HUT64322A (is)
NO (1) NO305973B1 (is)
NZ (1) NZ247477A (is)
RU (1) RU2130934C1 (is)
TW (1) TW232013B (is)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5455253A (en) * 1992-10-20 1995-10-03 Zeneca Limited Heterocyclic derivatives
KR100224135B1 (ko) * 1993-01-28 1999-10-15 다께다 구니오 퀴놀린 또는 퀴나졸린 유도체, 그 제조 및 용도
EP0625522B1 (en) * 1993-05-18 1998-08-19 Takeda Chemical Industries, Ltd. Benzopyran derivatives and their use
EP0634169B1 (en) * 1993-06-29 2000-01-05 Takeda Chemical Industries, Ltd. Quinoline or quinazoline derivatives and their use in the manufacture of a medicament for the treatment of osteoporosis
EP1247804A1 (en) * 1993-11-12 2002-10-09 PHARMACIA & UPJOHN COMPANY Pyrimidine-thioalkyl and alkylether compounds
TW384285B (en) * 1994-03-08 2000-03-11 Takeda Chemical Industries Ltd Pharmaceutical composition containing quinoline or quinazoline derivatives and novel derivatives therefor
US5641788A (en) 1994-06-07 1997-06-24 Takeda Chemical Industries, Ltd. Quinoline derivatives and pharmaceutical composition containing them
EP0830133A1 (en) * 1995-04-28 1998-03-25 Takeda Chemical Industries, Ltd. Therapeutic composition for arthritis
NZ310561A (en) * 1995-09-13 1999-07-29 Takeda Chemical Industries Ltd Immunosuppressant of the aromatic variety based upon the quinoline family
JP2002505288A (ja) 1998-03-02 2002-02-19 コセンシス，インコーポレイテッド 置換キナゾリンおよびアナログならびにそれらの使用
US6184226B1 (en) * 1998-08-28 2001-02-06 Scios Inc. Quinazoline derivatives as inhibitors of P-38 α
JP4048780B2 (ja) 1999-12-13 2008-02-20 株式会社豊田中央研究所 キノリン誘導体化合物及び有機電界発光素子
AR038658A1 (es) 2001-06-15 2005-01-26 Novartis Ag Derivados de 4-aril-2(1h) quinazolinona y 4-aril-quinazolina 2-sustituidas, un proceso para su preparacion, composiciones farmaceuticas y el uso de dichos derivados para la preparacion de un medicamento
US6620939B2 (en) 2001-09-18 2003-09-16 General Electric Company Method for producing bisphenol catalysts and bisphenols
CN100551532C (zh) * 2003-03-03 2009-10-21 沙伯基础创新塑料知识产权有限公司 制备双酚催化剂和双酚的方法
CN100579954C (zh) * 2004-06-25 2010-01-13 住友化学株式会社 (z)-1-苯基-1-二乙氨基羰基-2-羟甲基环丙烷的制造方法
SG176986A1 (en) 2009-06-25 2012-02-28 Amgen Inc Polycyclic derivatives of pyridine and their use in the treatment of (inter alia) rheumatoid arthritis and similar diseases
US9045435B2 (en) 2010-10-05 2015-06-02 Purdue Pharma, L.P. Quinazoline compounds as sodium channel blockers
CA2816144A1 (en) * 2010-11-17 2012-05-24 Amgen Inc. Quinoline derivatives as pik3 inhibitors
JP6258937B2 (ja) * 2012-08-24 2018-01-10 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ 新規二環式ピリジン誘導体
CN105814022B (zh) * 2013-12-09 2018-09-28 Ucb生物制药私人有限公司 作为tnf活性调节剂的稠合的二环杂芳族衍生物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2134169A1 (en) * 1971-04-23 1972-12-08 Clin Byla Ets 3-acyl-4-substd - quinoline derivs - analgesics, antiinflammatories, diuretics
ES2028834T3 (es) * 1986-09-12 1992-07-16 American Cyanamid Company Metodo para la preparacion de accidos piridin-2,3-dicarboxilico.
GB8716971D0 (en) * 1987-07-17 1987-08-26 Pfizer Ltd Therapeutic agents
CA1336714C (en) * 1987-08-20 1995-08-15 Yoshihiro Fujikawa Quinoline type mevalonolactone inhibitors of cholesterol biosynthesis
DE3935491A1 (de) * 1989-10-25 1991-05-02 Bayer Ag Substituierte (chinolin-2-yl-methoxy)phenyl-carbonylharnstoffe
AU652747B2 (en) * 1990-04-10 1994-09-08 Byk Gulden Lomberg Chemische Fabrik Gmbh Pyridines as medicaments
DE4105551A1 (de) * 1991-02-22 1992-08-27 Bayer Ag 2-substituierte chinoline, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
DE4129500A1 (de) * 1991-09-05 1993-03-11 Basf Ag Hochschlagzaehe, flammgeschuetzte polyphenylenether/polyamidformmassen
KR100224135B1 (ko) * 1993-01-28 1999-10-15 다께다 구니오 퀴놀린 또는 퀴나졸린 유도체, 그 제조 및 용도

Also Published As

Publication number Publication date
NO931482L (no) 1993-10-25
NO931482D0 (no) 1993-04-22
EP0567107A1 (en) 1993-10-27
EP0567107B1 (en) 2001-11-21
NZ247477A (en) 1995-07-26
CA2094774A1 (en) 1993-10-25
RU2130934C1 (ru) 1999-05-27
AU656069B2 (en) 1995-01-19
CN1079222A (zh) 1993-12-08
HU211852A9 (en) 1995-12-28
AU3699193A (en) 1993-10-28
FI931855A0 (fi) 1993-04-23
US5948782A (en) 1999-09-07
FI931855A (fi) 1993-10-25
TW232013B (is) 1994-10-11
HU9301197D0 (en) 1993-07-28
ATE209199T1 (de) 2001-12-15
KR940005273A (ko) 1994-03-21
DE69331171T2 (de) 2002-07-11
DE69331171D1 (de) 2002-01-03
HUT64322A (en) 1993-12-28

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