RU2008108984A - Терапевтический агент от диабета - Google Patents

Терапевтический агент от диабета Download PDF

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RU2008108984A
RU2008108984A RU2008108984/04A RU2008108984A RU2008108984A RU 2008108984 A RU2008108984 A RU 2008108984A RU 2008108984/04 A RU2008108984/04 A RU 2008108984/04A RU 2008108984 A RU2008108984 A RU 2008108984A RU 2008108984 A RU2008108984 A RU 2008108984A
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Russia
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group
optionally substituted
salt
compound according
oxy
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RU2008108984/04A
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Хиденори АБЕ (JP)
Хиденори АБЕ
Такеси ВАКАБАЯСИ (JP)
Такеси Вакабаяси
Кентароу РИКИМАРУ (JP)
Кентароу РИКИМАРУ
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Такеда Фармасьютикал Компани Лимитед (Jp)
Такеда Фармасьютикал Компани Лимитед
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Application filed by Такеда Фармасьютикал Компани Лимитед (Jp), Такеда Фармасьютикал Компани Лимитед filed Critical Такеда Фармасьютикал Компани Лимитед (Jp)
Publication of RU2008108984A publication Critical patent/RU2008108984A/ru

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    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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    • 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
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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    • A61P3/06—Antihyperlipidemics
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    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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    • C07C307/04—Diamides of sulfuric acids
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/04—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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    • 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
    • C07D211/36—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 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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    • 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
    • C07D213/79—Acids; Esters
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    • C07D231/20—One oxygen atom attached in position 3 or 5
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Abstract

1. Агент для профилактики или лечения диабета, содержащий соединение, представленное формулой ! ! где кольцо А является ароматическим кольцом, которое необязательно дополнительно замещено; ! Ar представляет собой необязательно замещенное моноциклическое кольцо; ! R1 представляет собой необязательно замещенную углеводородную группу или необязательно замещенную гетероциклическую группу; ! R2 представляет собой атом водорода, необязательно замещенную углеводородную группу или необязательно замещенную гетероциклическую группу; ! Х представляет собой спейсер, имеющий основную цепь из 1 или 2 атомов; ! Y представляет собой связь или спейсер, имеющий основную цепь из 1 или 2 атомов; ! W представляет собой необязательно замещенную двухвалентную углеводородную группу, имеющую 1-20 атомов углерода; ! Z представляет собой -CONRaSO2-, -SO2NRaCO-, -SO2NRaCOO-, -NRaSO2-, -OCONRaSO2-, -OCONRaSO2NRc-, -OCONRc-, -NRaCONRbSO2-, -NRaSO2NRbCOO- или -CONRaSO2NRc- (Ra и Rb представляют собой, каждый независимо, атом водород, необязательно замещенную углеводородную группу или аминозащитную группу, Rc представляет собой атом водород, необязательно замещенную углеводородную группу или аминозащитную группу, или Rc и R2, связанные друг с другом, образуют вместе с соседним атомом азота необязательно замещенный, азотсодержащий гетероцикл), ! или его соль, или его пролекарство. ! 2. Сенсибилизатор инсулина, содержащий соединение по п.1, или его соль, или его пролекарство. ! 3. Агент по п.1, где Ar представляет собой необязательно замещенное моноциклическое ароматическое кольцо. ! 4. Соединение, представленное формулой ! ! где кольцо А, Ar, R1, R2, X, Y, W, Z имеют значения, указанные в п.1 (при условии, что Ar не является незаме�

Claims (21)

1. Агент для профилактики или лечения диабета, содержащий соединение, представленное формулой
Figure 00000001
где кольцо А является ароматическим кольцом, которое необязательно дополнительно замещено;
Ar представляет собой необязательно замещенное моноциклическое кольцо;
R1 представляет собой необязательно замещенную углеводородную группу или необязательно замещенную гетероциклическую группу;
R2 представляет собой атом водорода, необязательно замещенную углеводородную группу или необязательно замещенную гетероциклическую группу;
Х представляет собой спейсер, имеющий основную цепь из 1 или 2 атомов;
Y представляет собой связь или спейсер, имеющий основную цепь из 1 или 2 атомов;
W представляет собой необязательно замещенную двухвалентную углеводородную группу, имеющую 1-20 атомов углерода;
Z представляет собой -CONRaSO2-, -SO2NRaCO-, -SO2NRaCOO-, -NRaSO2-, -OCONRaSO2-, -OCONRaSO2NRc-, -OCONRc-, -NRaCONRbSO2-, -NRaSO2NRbCOO- или -CONRaSO2NRc- (Ra и Rb представляют собой, каждый независимо, атом водород, необязательно замещенную углеводородную группу или аминозащитную группу, Rc представляет собой атом водород, необязательно замещенную углеводородную группу или аминозащитную группу, или Rc и R2, связанные друг с другом, образуют вместе с соседним атомом азота необязательно замещенный, азотсодержащий гетероцикл),
или его соль, или его пролекарство.
2. Сенсибилизатор инсулина, содержащий соединение по п.1, или его соль, или его пролекарство.
3. Агент по п.1, где Ar представляет собой необязательно замещенное моноциклическое ароматическое кольцо.
4. Соединение, представленное формулой
Figure 00000001
где кольцо А, Ar, R1, R2, X, Y, W, Z имеют значения, указанные в п.1 (при условии, что Ar не является незамещенным кольцом бензола),
или его соль, за исключением следующих соединений:
(4-(2-{[(4-хлорфенил)сульфонил]амино}этил)-3-{[3-(хинолин-2-илметокси)бензил]окси}фенокси)уксусной кислоты,
этил-(4-(2-{[(4-хлорфенил)сульфонил]амино}этил)-3-{[3-(хинолин-2-илметокси)бензил]окси}фенокси)ацетата,
1-{4-метокси-2-[(4-винилбензил)окси]фенил}этил-[4-(диэтиламино)-2-метилфенил]карбамата,
N-{2-[4,5-диметокси-2-(2-тиенилкарбонил)фенил]этил}-N,4-диметилбензолсульфонамида,
N-(2,2-диметоксиэтил)-N-{3-[6-({(2,2-диметоксиэтил)[(4-метилфенил)сульфонил]амино}метил)-2,3-диметоксифенокси]-4-метоксибензил}-4-метилбензолсульфонамида и
2-[2-(3,4-диметоксифенил)этил]-4,5-диметоксибензилфенилкарбамата.
5. Соединение по п.4, где Ar представляет собой необязательно замещенное моноциклическое ароматическое кольцо, или его соль.
6. Соединение по п.4, где Ar представляет собой необязательно замещенный 5- или 6-членный моноциклический ароматический гетероцикл, или его соль.
7. Соединение по п.4, где Ar представляет собой замещенное кольцо бензола, или его соль.
8. Соединение по п.4, где Х представляет собой атом кислорода, или его соль.
9. Соединение по п.4, где Z представляет собой -CONRaSO2-, или его соль.
10. Соединение по п.4, где R1 представляет собой
(1) С1-10алкильную группу или С2-10алкенильную группу, каждая из которых необязательно замещена 1-3 заместителями, выбранными из С1-6алкоксигруппы, необязательно замещенной С1-6алкоксигруппой;
карбамоильной группы, необязательно моно- или дизамещенной С1-6алкильной группой;
ароматической гетероциклической группы, необязательно замещенной С1-6алкильной группой;
неароматической гетероциклической группы, необязательно замещенной 1-3 заместителями, выбранными из С1-6алкильной группы и оксогруппы;
С1-6алкоксикарбонильной группы;
карбоксильной группы;
гидроксильной группы;
цианогруппы;
силилоксигруппы, необязательно замещенной 1-3 заместителями, выбранными из С1-6алкильной группы и С6-14арильной группы;
С1-6алкилкарбонилоксигруппы;
С3-10циклоалкилоксигруппы;
С3-10циклоалкил-С1-6алкилоксигруппы;
С1-6алкилсульфонильной группы;
С1-6алкилкарбонильной группы и
сульфамоилоксигруппы;
(2) С3-10циклоалкильную группу;
(3) С6-14арильную группу;
(4) С7-13аралкильную группу;
(5) С3-10-циклоалкил-С1-6алкильную группу;
(6) моноциклическую неароматическую гетероциклическую группу или
(7) моноциклическую ароматическую гетероциклическую группу, или его соль.
11. Соединение по п.4, где R2 представляет собой
(1) атом водорода;
(2) С1-10алкильную группу или С2-10алкенильную группу, каждая из которых необязательно замещена 1-3 заместителями, выбранными из С1-6алкоксигруппы; атома галогена; гидроксигруппы; цианогруппы; С1-6алкилтиогруппы; карбамоильной группы; С6-14арилоксигруппы; аминогруппы, необязательно замещенной 1 или 2 заместителями, выбранными из С1-6алкильной группы, С1-6алкилкарбонильной группы и С6-14арильной группы; ароматической гетероциклической группы, необязательно замещенной 1-3 С1-6алкильными группами; и неароматической гетероциклической группы, необязательно замещенной 1-3 заместителями, выбранными из С1-6алкильной группы и оксогруппы;
(3) С3-10циклоалкильную группу, необязательно замещенную С1-6алкильной группой и необязательно конденсированную с кольцом бензола;
(4) С6-14арильную группу, необязательно замещенную 1-3 заместителями, выбранными из С1-6алкильной группы, необязательно замещенной 1-3 атомами галогена, гидроксигруппы, С1-6алкоксигруппы, атома галогена, нитрогруппы и цианогруппы;
(5) С7-13аралкильную группу, необязательно замещенную 1-3 заместителями, выбранными из С1-6алкоксигруппы и С6-14арильной группы;
(6) С3-10циклоалкил-С1-6алкильную группу или
(7) неароматическую гетероциклическую группу, необязательно замещенную оксогруппой, или его соль.
12. Соединение по п.4, где кольцо A представляет собой бензольное кольцо или 5- или 6-членный ароматический гетероцикл, или его соль.
13. Соединение по п.4, где Y представляет собой связь, -О- или -SO2-, или его соль.
14. Соединение по п.4, где W представляет собой С1-6алкилен или С2-6алкенилен, или его соль.
15. Соединение по п.4, представляющее собой:
3-(2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-изопропоксифенил)-N-(пентилсульфонил)пропанамид,
(2E)-3-[2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-(2-метоксиэтокси)фенил]-N-(пентилсульфонил)акриламид,
3-[2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-(2-метоксиэтокси)фенил]пропил(пентилсульфонил)карбамат,
3-[3-бутокси-1-(2,4-дихлорбензил)-1H-пиразол-5-ил]-N-(пентилсульфонил)пропанамид,
3-{3-трет-бутил-1-[2-хлор-4-(трифторметил)бензил]-1H-пиразол-5-ил}-N-(пентилсульфонил)пропанамид,
бутил-({2-[3-бутокси-1-(2,4-дихлорбензил)-1H-пиразол-5-ил]этил}сульфонил)карбамат,
(2E)-3-{2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-[2-этокси-1-(этоксиметил)этокси]фенил}-N-(пентилсульфонил)акриламид,
3-[2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-(2-метоксиэтокси)фенил]пропил-{[(2-изопропоксиэтил)амино]сульфонил}карбамат,
3-[2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-(2-метоксиэтокси)фенил]пропил-{[(2-пиридин-2-илэтил)амино]сульфонил}карбамат,
3-[2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-(2-метоксиэтокси)фенил]-N-[(пентиламино)сульфонил]пропанамид,
(2E)-3-[2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-(2-гидрокси-2-метилпропокси)фенил]-N-(пентилсульфонил)акриламид или
3-[2-{[3-хлор-5-(трифторметил)пиридин-2-ил]окси}-4-(2-гидроксиэтокси)фенил]пропил-{[(2-изопропоксиэтил)амино]сульфонил}карбамат, или
его солью.
16. Пролекарство соединения по п.4 или его соли.
17. Фармацевтический агент, содержащий соединение по п.4, или его соль, или его пролекарство.
18. Способ профилактики или лечения диабета у млекопитающего, включающий введение соединения по п.1, или его соли, или его пролекарства млекопитающему.
19. Способ повышения инсулинорезистентности у млекопитающего, включающий введение соединения по п.1, или его соли, или его пролекарства млекопитающему.
20. Применение соединения по п.1, или его соли, или его пролекарства для получения агента для профилактики или лечения диабета.
21. Применение соединения по п.1, или его соли, или его пролекарства для получения сенсибилизатора инсулина.
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