RO90954A - Procedeu pentru prepararea unor derivati de 1,4-dihidropiridina - Google Patents

Procedeu pentru prepararea unor derivati de 1,4-dihidropiridina

Info

Publication number
RO90954A
RO90954A RO85118129A RO11812985A RO90954A RO 90954 A RO90954 A RO 90954A RO 85118129 A RO85118129 A RO 85118129A RO 11812985 A RO11812985 A RO 11812985A RO 90954 A RO90954 A RO 90954A
Authority
RO
Romania
Prior art keywords
preparation
substd
opt
dihydropyridine derivatives
dihydropyridine
Prior art date
Application number
RO85118129A
Other languages
English (en)
French (fr)
Other versions
RO90954B (ro
Inventor
Maria J Casanova
Joaquin A G Ramos
Original Assignee
Instituto De Investigacion Y Desarrolo Quimico-Biologico Sa,Es
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
Priority claimed from ES531033A external-priority patent/ES8507495A1/es
Priority claimed from ES536537A external-priority patent/ES8506703A1/es
Application filed by Instituto De Investigacion Y Desarrolo Quimico-Biologico Sa,Es filed Critical Instituto De Investigacion Y Desarrolo Quimico-Biologico Sa,Es
Publication of RO90954A publication Critical patent/RO90954A/ro
Publication of RO90954B publication Critical patent/RO90954B/ro

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • 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
    • C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—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 two 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 directly attached to ring carbon atoms
    • C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by 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
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Endocrinology (AREA)
  • Rheumatology (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
RO118129A 1984-03-27 1985-03-25 Procedeu pentru prepararea unor derivati de 1,4-dihidropiridina RO90954B (ro)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES531033A ES8507495A1 (es) 1984-03-27 1984-03-27 Un procedimiento para la preparacion de nuevas 1,4-dihidropirinas-4-(polioxialquilfenil)-sustituidas
ES536537A ES8506703A1 (es) 1984-10-04 1984-10-04 Un procedimiento para la preparacion de 4-(2', 3'-dioxometilenfenil)-1, 4-dihidropiridinas

Publications (2)

Publication Number Publication Date
RO90954A true RO90954A (ro) 1987-02-27
RO90954B RO90954B (ro) 1987-02-28

Family

ID=26156079

Family Applications (1)

Application Number Title Priority Date Filing Date
RO118129A RO90954B (ro) 1984-03-27 1985-03-25 Procedeu pentru prepararea unor derivati de 1,4-dihidropiridina

Country Status (32)

Country Link
US (1) US4722931A (ro)
EP (1) EP0158211B1 (ro)
AT (1) ATE79868T1 (ro)
AU (1) AU571316B2 (ro)
BE (1) BE902016A (ro)
BG (1) BG41127A3 (ro)
CA (1) CA1253158A (ro)
CH (1) CH663020A5 (ro)
CS (1) CS259877B2 (ro)
DE (2) DE3510762A1 (ro)
DK (1) DK167676B1 (ro)
FI (1) FI82937C (ro)
FR (1) FR2562069A1 (ro)
GB (1) GB2156809B (ro)
GR (1) GR850736B (ro)
HU (1) HU193746B (ro)
IE (1) IE57810B1 (ro)
IL (1) IL74634A (ro)
IS (1) IS1366B6 (ro)
IT (1) IT1209946B (ro)
LU (1) LU85816A1 (ro)
MX (1) MX7378E (ro)
NO (1) NO167509C (ro)
NZ (1) NZ211456A (ro)
OA (1) OA07972A (ro)
PH (1) PH21945A (ro)
PL (1) PL147055B1 (ro)
PT (1) PT80166B (ro)
RO (1) RO90954B (ro)
SU (1) SU1329619A3 (ro)
YU (1) YU44059B (ro)
ZW (1) ZW5385A1 (ro)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2568773B1 (fr) * 1984-08-10 1989-03-03 Sandoz Lab Nouvelles compositions pharmaceutiques administrables par voie nasale
DE3716652A1 (de) * 1987-05-19 1988-12-08 Bayer Ag Dioxyalkylenaryl-dihydropyridine, zwischenprodukte zu ihrer herstellung, verfahren zu ihrer herstellung und ihre verwendung
DE3768658D1 (de) * 1987-08-03 1991-04-18 Delagrange Lab 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.

Family Cites Families (34)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048178A (en) * 1960-03-10 1977-09-13 Smith Kline & French Laboratories Novel N-allyl and N-propargyl benzmorphan derivatives
US3441648A (en) * 1967-02-07 1969-04-29 Smithkline Corp Compositions and methods for lowering blood pressure with 1,4-dihydropyridines
DE1670827C3 (de) * 1967-03-20 1974-10-24 Bayer Ag, 5090 Leverkusen 4-(2'-Nitrophenyl)-2,6-dimethyl-3,5-dicarbmethoxy-1,4-dihydropyridin
ZA7152B (en) * 1970-01-24 1971-10-27 Bayer Ag New pharmaceutically active 1,4-dihydropyridines
DE2117572C3 (de) * 1971-04-10 1980-03-20 Bayer Ag, 5090 Leverkusen Unsymmetrische 1,4-Dihydropyridin ^-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
US3932645A (en) * 1971-04-10 1976-01-13 Farbenfabriken Bayer Ag Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acid
US3932646A (en) * 1971-04-10 1976-01-13 Farbenfabriken Bayer Ag Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylate
DE2117571C3 (de) * 1971-04-10 1979-10-11 Bayer Ag, 5090 Leverkusen Unsymmetrische 1,4-Dihydropyridin-33-dicarbonsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE2117573C3 (de) * 1971-04-10 1978-07-27 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von unsymmetrischen l,4-Dihydropyridin-3,5dicarbonsäureestern, sowie ihre Verwendung als Arzneimittel
US4031104A (en) * 1972-04-18 1977-06-21 Bayer Aktiengesellschaft 1,4-Dihydropyridine carboxylic acid esters
DE2218644C3 (de) * 1972-04-18 1982-08-19 Bayer Ag, 5090 Leverkusen Basische Ester von 1,4-Dihydropyridinen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE2228363A1 (de) * 1972-06-10 1974-01-03 Bayer Ag 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
GB1409865A (en) * 1973-02-13 1975-10-15 Science Union & Cie Dihydropyridines derivatives their preparation and pharmaceu tical compositions containing them
US3985758A (en) * 1973-02-20 1976-10-12 Yamanouchi Pharmaceutical Co., Ltd. 1,4-Dihydropyridine derivatives
US3956341A (en) * 1974-02-21 1976-05-11 Smithkline Corporation 1,3,5-Tricarbo-1,4-dihydropyridines
US4338322A (en) * 1975-07-02 1982-07-06 Fujisawa Pharmaceutical Co., Ltd. 1,4-Dihydropyridine derivatives, pharmaceutical compositions containing same and methods of effecting vasodilation using same
US4284634A (en) * 1975-07-02 1981-08-18 Fujisawa Pharmaceutical Co., Ltd. 1,4-Dihydropyridine derivatives, and pharmaceutical method of the same
US4370334A (en) * 1975-07-02 1983-01-25 Fujisawa Pharmaceutical Co., Ltd. 1,4-Dihydro-pyridine derivatives and methods of using same
DK149855C (da) * 1977-06-20 1987-04-21 Sandoz Ag Analogifremgangsmaade til fremstilling af 1,4-dihydropyridinderivater
SU706410A1 (ru) * 1978-01-11 1979-12-30 Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвийской Сср 2,6-Диметил-3,5-дикарбметокси-4(0-дифторметоксифенил)-1,4-дигидропиридин,обладающий выраженной гипотензивной активностью и оказывающий действие на функции вегетативной нервной системы
SE429652B (sv) * 1978-06-30 1983-09-19 Haessle Ab 2.6-dimetyl-4-(2.3-diklorfenyl)-1.4-dihydropyridin-3.5-dikarboxylsyra-3-metylester-5-etylester
DE2841667A1 (de) * 1978-09-25 1980-04-10 Bayer Ag Fluorhaltige 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2847236A1 (de) * 1978-10-31 1980-05-14 Bayer Ag Neue dihydropyridine mit substituierten estergruppierungen, mehrer verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2935451A1 (de) * 1979-09-01 1981-03-19 Bayer Ag, 5090 Leverkusen Optisch aktive 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arneimittel
US4258042A (en) * 1980-04-11 1981-03-24 Usv Pharmaceutical Corporation Antihypertensive pyridines and compositions
DE3022030A1 (de) * 1980-06-12 1981-12-17 Bayer Ag, 5090 Leverkusen 4-thiazol- bzw. 4-imidazol-substituierte, 1,4-dihydropyridine, verfahren zu deren herstellung sowie diese enthaltende arzneimittel
NZ201395A (en) * 1981-07-30 1987-02-20 Bayer Ag Pharmaceutical compositions containing 1,4-dihydropyridines and certain of these dihydropyridines
GB2111978B (en) * 1981-10-19 1985-05-01 Maruko Pharmaceutical Co 1 4-dihydropyridine compounds
DE3207982A1 (de) * 1982-03-05 1983-09-08 Bayer Ag, 5090 Leverkusen Neue 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihrer verwendung in arzneimitteln
DE3208628A1 (de) * 1982-03-10 1983-09-22 Bayer Ag, 5090 Leverkusen Neue verbindungen, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
ATE50987T1 (de) * 1982-05-10 1990-03-15 Takeda Chemical Industries Ltd Dihydropyridinderivate, deren herstellung und verwendung.
DE3222367A1 (de) * 1982-06-15 1983-12-15 Bayer Ag, 5090 Leverkusen Verwendung von 1,4-dihydropyridinen in antiarteriosklerotika und deren herstellung
US4656181A (en) * 1982-11-24 1987-04-07 Cermol S.A. Esters of 1,4-dihydropyridines, processes for the preparation of the new esters, and medicaments containing the same
EP0125803A3 (en) * 1983-04-27 1987-01-21 FISONS plc Pharmaceutically active dihydropyridines

Also Published As

Publication number Publication date
PL147055B1 (en) 1989-04-29
US4722931A (en) 1988-02-02
BE902016A (fr) 1985-09-25
IL74634A (en) 1988-08-31
IE57810B1 (en) 1993-04-21
HU193746B (en) 1987-11-30
EP0158211A2 (fr) 1985-10-16
GR850736B (ro) 1985-07-17
FI82937C (fi) 1991-05-10
DK167676B1 (da) 1993-12-06
EP0158211A3 (en) 1988-10-12
OA07972A (fr) 1987-01-31
GB2156809A (en) 1985-10-16
CH663020A5 (fr) 1987-11-13
GB2156809B (en) 1988-05-25
IS2992A7 (is) 1985-09-28
FI851218A0 (fi) 1985-03-26
DE3586546T2 (de) 1993-03-18
RO90954B (ro) 1987-02-28
MX7378E (es) 1988-08-19
BG41127A3 (en) 1987-04-15
FI851218L (fi) 1985-09-28
PL252576A1 (en) 1985-12-03
ATE79868T1 (de) 1992-09-15
GB8507358D0 (en) 1985-05-01
IS1366B6 (is) 1989-05-25
NO167509C (no) 1991-11-13
IT8547865A0 (it) 1985-03-26
LU85816A1 (fr) 1985-12-12
SU1329619A3 (ru) 1987-08-07
PT80166B (pt) 1987-06-17
FI82937B (fi) 1991-01-31
ZW5385A1 (en) 1985-08-21
FR2562069A1 (fr) 1985-10-04
IL74634A0 (en) 1985-06-30
CS221385A2 (en) 1988-03-15
NO851206L (no) 1985-09-30
HUT37598A (en) 1986-01-23
NO167509B (no) 1991-08-05
NZ211456A (en) 1988-11-29
DK135285A (da) 1985-09-28
PT80166A (en) 1985-04-01
DE3586546D1 (de) 1992-10-01
AU571316B2 (en) 1988-04-14
YU44059B (en) 1990-02-28
YU47185A (en) 1987-12-31
IE850627L (en) 1985-09-27
IT1209946B (it) 1989-08-30
CS259877B2 (en) 1988-11-15
DK135285D0 (da) 1985-03-26
DE3510762A1 (de) 1985-11-21
AU4014685A (en) 1985-10-03
CA1253158A (fr) 1989-04-25
EP0158211B1 (fr) 1992-08-26
PH21945A (en) 1988-04-15

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