RU2510503C2 - Модулирование хемосенсорных рецепторов и связанных с ними лигандов - Google Patents

Модулирование хемосенсорных рецепторов и связанных с ними лигандов Download PDF

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RU2510503C2
RU2510503C2 RU2009148316/15A RU2009148316A RU2510503C2 RU 2510503 C2 RU2510503 C2 RU 2510503C2 RU 2009148316/15 A RU2009148316/15 A RU 2009148316/15A RU 2009148316 A RU2009148316 A RU 2009148316A RU 2510503 C2 RU2510503 C2 RU 2510503C2
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RU2009148316A (ru
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Кэтрин ТАЧДЖИАН
Доналд С. КАРАНЕВСКИЙ
Сяо-цин ТАН
Сяодун ЛИ
Фын ЧЖАН
Гай СЕРВАНТ
Цин Чэнь
Винсент ДАРМОХИСОДО
Ричард ФАЙН
Джозеф Р. ФОТСИНГ
Джеффри Роберт ХЭММЕЙКЕР
Синьшань КАН
Рашель Д.А. КИММИЧ
Борис КЛЕБАНСКИЙ
Хайтянь ЛЮ
Горан ПЕТРОВИЧ
Маркета РИННОВА
Сара АДАМСКИ-ВЕРНЕР
Джеффри ЯМАМОТО
Хун Чжан
Альберт ЗЛОТНИК
Марк ЗОЛЛЕР
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Синомикс, Инк.
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Abstract

Группа изобретений относится к соединениям - модификаторам хемосенсорных рецепторов и их лигандов, имеющим структурную формулу (IIIb), их подвидам и конкретным соединениям, съедобным композициям, содержащим модификаторы хемосенсорных рецепторов и их лигандов, имеющие структурную формулу (IIIb), их подвиды и конкретные соединения, а также к способам применения вышеуказанных соединений для улучшения сладкого вкуса съедобных композиций. Соединения данной группы изобретений обеспечивают возможность получения и улучшения сладкого вкуса. 6 н. и 18 з.п. ф-лы, 19 ил., 44 табл., 813 пр.

Description

Текст описания приведен в факсимильном виде.
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Claims (24)

1. Соединение, имеющее структурную формулу (IIIb):
Figure 00000567

или его таутомер, соль, сольват и/или его сложный эфир, где
A является NH2;
Н является -C(R35)- или -N-;
I является -C(R36)- или -N-;
J является -C(R37)- или -N-;
K является -C(R38)-;
R17 является водородом;
R35 является водородом;
R36 является водородом;
R37 является водородом, фтором, хлором или бромом;
R38 является алкенилом, замещенным алкенилом, алкинилом, замещенным алкинилом, циклоалканилом, замещенным циклоалканилом, циклоалкенилом, замещенным циклоалкенилом, гетероалкилом, замещенным гетероалкилом, циклогетероалкилом, замещенным циклогетероалкилом, -O-алканилом, -O-(замещенным алканилом), -O-гетероалкилом, -O-(замещенным гетероалкилом), -O-алкенилом, -O-(замещенным алкенилом), -NH-алканилом, -NH-(замещенным алканилом), -NH-алкенилом, -NH-(замещенным алкенилом), -S-алканилом, -S-(замещенным алканилом), -S-алкенилом или -S-(замещенным алкенилом).
2. Соединение по п.1,
где Н является -C(R35)-;
I является -C(R36)-;
J является -C(R37)-; и
K является -C(R38)-
3. Соединение, имеющее структурную формулу (IIIb1):
Figure 00000568

где
A является водородом, алкилом, замещенным алкилом, арилом, замещенным арилом, арилалкилом, замещенным арилалкилом, ацилом, замещенным ацилом, гетероалкилом, замещенным гетероалкилом, гетероарилом, замещенным гетероарилом, гетероарилалкилом, замещенным гетероарилалкилом, -CN, -OR9, -NO2, -S(O)cR9, -NHOR9, -NR9COR10, -NR9R10, -CONR9R10, -CO2R9 или -NR9CO2R10;
R17 является водородом, алкилом, замещенным алкилом, арилалкилом или замещенным арилалкилом;
X1 является -СН2-, -O-, -NR9-, -S-, -S(O)- или -S(O)2-;
X2 является алкиленом, замещенным алкиленом, гетероалкиленом или замещенным гетероалкиленом;
m равно 0 или 1;
Y1 является гетероарилом, замещенным гетероарилом, циклогетероалкилом, замещенным циклогетероалкилом или
Figure 00000569

X3 и X5 независимо являются ковалентной связью, -O- или -NR9-;
X4 является O, NR9, N-OR9 или S;
Rx является галогеном, -NO2, -CN, -OH, -NH2, алкилом, замещенным алкилом, арилом, замещенным арилом, арилалкилом, замещенным арилалкилом, гетероалкилом, замещенным гетероалкилом, гетероарилом, замещенным гетероарилом, гетероарилалкилом или замещенным гетероарилалкилом;
n равно 0, 1, 2 или 3;
Ry является водородом, алкилом, замещенным алкилом, арилом, замещенным арилом, арилалкилом, замещенным арилалкилом, гетероалкилом, замещенным гетероалкилом, гетероарилом, замещенным гетероарилом, гетероарилалкилом или замещенным гетероарилалкилом, -NR9R10; и
каждый R9 и R10 независимо является водородом, алкилом, замещенным алкилом, арилом, замещенным арилом, арилалкилом, замещенным арилалкилом, гетероалкилом, замещенным гетероалкилом, гетероарилом, замещенным гетероарилом, гетероарилалкилом или замещенным гетероарилалкилом;
при условии, что если X1 является -O- или -S-, и m равно нулю; то X3 не является -O-.
4. Соединение по п.3, где
X1 является -СН2-; и
Y1 является
Figure 00000570

где
X1 является -O-, -NR9- или -S-;
m равно 0 или 1, и
Y1 является циклогетероалкилом или замещенным циклогетероалкилом;
или
где
X1 является -O-, -NR9- или -S-;
m равно 1, и
Y1 является
Figure 00000571
5. Соединение по любому из пп.3 или 4, где
X2 является метиленом, этиленом, пропиленом, изо-пропиленом, бутиленом, изо-бутиленом, втор-бутиленом, пентиленом, гексиленом, гептиленом, диметилэтиленом, метилциклопропиленом, циклопропилметиленом, этениленом, пропениленом или бутениленом.
6. Соединение по п.3, где
а) Y1 является пиперидинилом, замещенным пиперидинилом/ тетрагидрофуранилом, замещенным тетрагидрофуранилом, тетрагидропиранилом, замещенным тетрагидропиранилом, дигидрофуранилом, замещенным дигидрофуранилом, пирролидинилом, замещенным пирролидинилом, оксетанилом, замещенным оксетанилом, сахаридным кольцом или его производным, замещенным сахаридным кольцом или его производным;
или где
б) Y1 является пиридинилом, замещенным пиридинилом, пирролилом, замещенным пирролилом, фуранилом, замещенным фуранилом, пиразолилом, замещенным пиразолилом, изоксазолилом, замещенным изоксазолилом, оксазолилом и замещенным оксазолилом;
или где
в) замещенный циклогетероалкил содержит один или более заместителей, выбранных из группы, включающей алкил, замещенный алкил, арил, замещенный арил, арилалкил, замещенный арилалкил, ацил, замещенный ацил, гетероалкил, замещенный гетероалкил, гетероарил, замещенный гетероарил, гетероарилалкил, замещенный гетероарилалкил, -CN, -OR9, -NO2, -S(O)cR9, -NHOR9, -NR9COR10, -NR9R10, -CONR9R10, -CO2R9 и -NR9CO2R10;
или где
г) Y1 является
Figure 00000572

или где
д) -X3-C(X4)-X5- является -C(O)-, -C(O)-NH-, -NH-C(O)-, -NH-C(O)-NH-, -C(O)-O-, -O-C(O)-, -O-C(O)-O-, -NH-C(O)-O-, -O-C(O)-NH-, -C(NH)-, -C(NH)-NH-, -NH-C(NH)-, -NH-C(NH)-NH-, -C(NH)-O-, -O-C(NH)-, -O-C(NH)-O, -NH-C(NH)-O-, -O-C(NH)-NH-, -C(N-OH)- или -C(S)-;
или где
е) A является водородом, алкилом, замещенным алкилом или -NR9R10;
R17 является водородом; и
Y1 является пиперидинилом, замещенным пиперидинилом, тетрагидрофуранилом, замещенным тетрагидрофуранилом, тетрагидропиранилом, замещенным тетрагидропиранилом, дигидрофуранилом, замещенным дигидрофуранилом, пирролидинилом, замещенным пирролидинилом, оксетанилом, замещенным оксетанилом, моносахаридным кольцом, замещенным моносахаридным кольцом, пиридинилом, замещенным пиридинилом, пирролилом, замещенным пирролилом, фуранилом, замещенным фуранилом, пиразолилом, замещенным пиразолилом, изоксазолилом, замещенным изоксазолилом, оксазолилом или замещенным оксазолилом;
или где
ж) A является водородом, алкилом, замещенным алкилом или -NR9R10;
R17 является водородом;
Y1 является -X3-C(X4)-X5-; и
-X3-С(Х4)-Х5- является -C(O)-, -C(O)-NH-, -NH-C(O)-, -NH-C(O)-NH-, -C(O)-O-, -O-C(O)-, -O-C(O)-O-, -NH-C(O)-O-, -O-C(O)-NH-, -C(NH)-, -C(NH)-NH-, -NH-C(NH)-, -NH-C(NH)-NH-, -C(NH)-O-, -O-C(NH)-, -O-C(NH)-O-, -NH-C(NH)-O-, -O-C(NH)-NH-, -S(O)2-, -NH-S(O)2-, -S(O)2-NH-, -O-S(O)2-, -S(O)2-O-, -C(N-OH)- или -C(S)-.
7. Соединение по п.1 или 3, имеющее структурную формулу, выбранную из группы, включающей
Figure 00000573

Figure 00000574

Figure 00000575

Figure 00000576


Figure 00000578

Figure 00000579

Figure 00000580

Figure 00000581

Figure 00000582

Figure 00000583

Figure 00000584

Figure 00000585

Figure 00000586

Figure 00000587

Figure 00000588

Figure 00000589

Figure 00000590

Figure 00000591

Figure 00000592

Figure 00000593

Figure 00000594

Figure 00000595

Figure 00000596

Figure 00000597

Figure 00000598

Figure 00000599

Figure 00000600

Figure 00000601

Figure 00000602

Figure 00000603

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Figure 00000607

Figure 00000608

Figure 00000609

Figure 00000610

Figure 00000611

Figure 00000612

Figure 00000613

Figure 00000614

Figure 00000615

Figure 00000616

Figure 00000617

Figure 00000618

Figure 00000619

Figure 00000620

Figure 00000621

Figure 00000622

Figure 00000623

Figure 00000624

Figure 00000625

Figure 00000626

Figure 00000627

Figure 00000628

Figure 00000629

Figure 00000630

Figure 00000631

Figure 00000632

Figure 00000633

Figure 00000634

Figure 00000635

Figure 00000636

Figure 00000637

Figure 00000638

Figure 00000639

Figure 00000640

Figure 00000641

Figure 00000642

Figure 00000643

Figure 00000644

Figure 00000645

Figure 00000646

Figure 00000647

Figure 00000648

Figure 00000649

Figure 00000650

Figure 00000651

Figure 00000652

Figure 00000653

Figure 00000654

Figure 00000655

Figure 00000656

Figure 00000657

Figure 00000658

Figure 00000659

Figure 00000660

Figure 00000661

Figure 00000662

Figure 00000663

Figure 00000664

Figure 00000665

Figure 00000666

Figure 00000667

или его таутомер, соль, сольват и/или его сложный эфир.
8. Проглатываемая композиция, содержащая соединение, имеющее структурную формулу (IIIb) по п.1 или структурную формулу (IIIb1) по п.3, или его таутомер, соль, сольват и/или его сложный эфир.
9. Проглатываемая композиция по п.8, выбранная из группы, включающей пищевой продукт или напиток, несъедобный продукт, фармацевтическую композицию и их сочетание.
10. Проглатываемая композиция по п.9, где пищевой продукт или напиток выбирают из группы, включающей категорию супов; категорию высушенных бакалейных товаров; категорию напитков; категорию готовых блюд; категорию консервированных продуктов; категорию замороженных бакалейных товаров; категорию охлажденных бакалейных товаров; категорию закусок; категорию хлебобулочных изделий; категорию кондитерских изделий; категорию молочных продуктов; категорию мороженого; категорию заменителей пищи; категорию макарон и лапши; категорию соусов, заправок, приправ; категорию детского питания; категорию спредов; категорию сладких покрытий, глазировки или глазури; и их сочетание.
11. Проглатываемая композиция по п.9, где несъедобный продукт выбирают из группы, включающей нутрицевтики и пищевые добавки, безрецептурные лекарственные средства, продукты по уходу за полостью рта и косметические продукты.
12. Проглатываемая композиция по п.8, где соединение, имеющее структурную формулу (IIIb) по п.1 или структурную формулу (IIIb1) по п.3, или таутомер, соль, сольват и/или его сложный эфир, находится в количестве, улучшающем сладкий вкус; предпочтительно, где количество, улучшающее сладкий вкус, не является терапевтически эффективным количеством.
13. Проглатываемая композиция по любому одному из пп.8, 9, 10, 11 или 12, также содержащая, по крайней мере, один подсластитель.
14. Проглатываемая композиция по п.13, где соединение, улучшающее сладкий вкус, выбирают из группы, включающей сахарозу, фруктозу, глюкозу, галактозу, маннозу, лактозу, тагатозу, мальтозу, кукурузный сироп (включая кукурузный сироп с высоким содержанием фруктозы), D- триптофан, глицин, эритритол, изомальт, лактит, маннит, сорбит, ксилит, мальтодекстрин, мальтит, изомальт, гидрированный сироп глюкозы (HGS), гидрированный гидролизат крахмала (HSH), стевиозид, ребаудиозид А и другие сладкие гликозиды на основе стевии, карелам, другие подсластители на основе гуанидина, сахарин, ацесульфам К, цикламат, сукралозу, алитам, могросид, неотам, аспартам, другие производные аспартама и их сочетания.
15. Проглатываемая композиция по п.13, где, по крайней мере, одно соединение, улучшающее сладкий вкус, содержит
по крайней мере, один натуральный подсластитель; и
по крайней мере, один искусственный или синтезированный подсластитель.
16. Проглатываемая композиция по п.15, где природным подсластителем является сахаридный подсластитель, натуральный сахар или полусинтетический подсластитель на основе «сахарного спирта».
17. Проглатываемая композиция по п.16, где искусственным или синтезированным подсластителем является некалорийная сладкая вкусовая добавка, сладкая вкусовая добавка с пониженной калорийностью или нецелевая калорийная сладкая вкусовая добавка.
18. Проглатываемая композиция по п.16, где природный подсластитель выбирают из группы, включающей сахарозу, фруктозу, глюкозу, тагатозу, мальтозу, галактозу, маннозу, лактозу, глицин, кукурузный сироп или другие сиропы или концентраты подсластителя, полученных из натуральных фруктов и растительных источников, эритритол, изомальт, лактит, маннит, сорбит, ксилит, мальтодекстрин и могрозид.
19. Проглатываемая композиция по п.17, где искусственный или синтезированный подсластитель выбирают из группы, включающей аспартам, сахарин, ацесульфам-К, цикламат, сукралозу, алитам, аспартам, неотам, производные аспартама, D-триптофан, гидрированный сироп глюкозы (HGS), гидрированный гидролизат крахмала (HSH), стевиозид, ребаудиозид А, сладкие гликозиды на основе стевии, карелам и подсластители на основе гуанидина.
20. Подслащивающая композиция, содержащая соединение, имеющее структурную формулу (IIIb) по п.1 или структурную формулу (IIIb1) по п.3, или его таутомер, соль, сольват и/или его сложный эфир.
21. Способ улучшения сладкого вкуса съедобной композиции, включающий взаимодействие съедобной композиции или ее предшественников с соединением, имеющим структурную формулу (IIIb) по п.1, структурную формулу (IIIb1) по п.3, или его таутомером, солью, сольватом и/или сложным эфиром.
22. Способ улучшения сладкого вкуса съедобной композиции, включающий взаимодействие съедобной композиции или ее предшественников с подслащивающей композицией по п.20.
23. Проглатываемая композиция по п.8, которая представлена в пищевом продукте или напитке.
24. Проглатываемая композиция по п.8, которая представлена в твердом или жидком концентрате.
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