RU99103124A - ЗАМЕЩЕННЫЕ 2-(2,6-ДИОКСОПИПЕРИДИН-3-ИЛ)-ФТАЛИМИДЫ И-1-ОКСОИЗОИНДОЛИНЫ И СПОСОБ СНИЖЕНИЯ УРОВНЕЙ TNFα - Google Patents
ЗАМЕЩЕННЫЕ 2-(2,6-ДИОКСОПИПЕРИДИН-3-ИЛ)-ФТАЛИМИДЫ И-1-ОКСОИЗОИНДОЛИНЫ И СПОСОБ СНИЖЕНИЯ УРОВНЕЙ TNFαInfo
- Publication number
- RU99103124A RU99103124A RU99103124/04A RU99103124A RU99103124A RU 99103124 A RU99103124 A RU 99103124A RU 99103124/04 A RU99103124/04 A RU 99103124/04A RU 99103124 A RU99103124 A RU 99103124A RU 99103124 A RU99103124 A RU 99103124A
- Authority
- RU
- Russia
- Prior art keywords
- dioxopiperidin
- oxo
- aminoisoindoline
- carbon atoms
- compound according
- Prior art date
Links
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 title claims 4
- 108010001801 Tumor Necrosis Factor-alpha Proteins 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000004432 carbon atoms Chemical group C* 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- XKAYAFBLGLCWSY-UHFFFAOYSA-N 3-(4-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C=2C(N)=CC=CC=2CN1C1CCC(=O)NC1=O XKAYAFBLGLCWSY-UHFFFAOYSA-N 0.000 claims 2
- WLUIQUZGNPAKRL-UHFFFAOYSA-N 3-(6-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C2=CC(N)=CC=C2C(=O)N1C1CCC(=O)NC1=O WLUIQUZGNPAKRL-UHFFFAOYSA-N 0.000 claims 2
- GOTYRUGSSMKFNF-UHFFFAOYSA-N Lenalidomide Chemical compound C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O GOTYRUGSSMKFNF-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- -1 1-oxo-2- (2,6-dioxopiperidin-3-yl) -6-aminoisoindolyl Chemical group 0.000 claims 1
- HKEZQPMXDKBNJN-UHFFFAOYSA-N 3-(4,5,6,7-tetrachloro-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2CN1C1CCC(=O)NC1=O HKEZQPMXDKBNJN-UHFFFAOYSA-N 0.000 claims 1
- ACMVMVHUTTZSBR-UHFFFAOYSA-N 3-(4,5,6,7-tetrafluoro-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(F)C(F)=C(F)C(F)=C2CN1C1CCC(=O)NC1=O ACMVMVHUTTZSBR-UHFFFAOYSA-N 0.000 claims 1
- VEEGBANOMRHUOB-UHFFFAOYSA-N 3-(4,5,6,7-tetramethoxy-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(OC)C(OC)=C(OC)C(OC)=C2CN1C1CCC(=O)NC1=O VEEGBANOMRHUOB-UHFFFAOYSA-N 0.000 claims 1
- RFEZFLDQHUMVOF-UHFFFAOYSA-N 3-(4,5,6,7-tetramethyl-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=C(C)C(C)=C(C)C(C)=C2CN1C1CCC(=O)NC1=O RFEZFLDQHUMVOF-UHFFFAOYSA-N 0.000 claims 1
- LAGNQECGHYBSCQ-UHFFFAOYSA-N 3-(5-amino-3-oxo-1H-isoindol-2-yl)piperidine-2,6-dione Chemical compound O=C1C2=CC(N)=CC=C2CN1C1CCC(=O)NC1=O LAGNQECGHYBSCQ-UHFFFAOYSA-N 0.000 claims 1
- VZTDWPXKIYLLAT-UHFFFAOYSA-N 4-amino-2-(3-methyl-2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC(N)=C2C(=O)N1C1(C)CCC(=O)NC1=O VZTDWPXKIYLLAT-UHFFFAOYSA-N 0.000 claims 1
- IICWMVJMJVXCLY-UHFFFAOYSA-N 5-amino-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC(N)=CC=C2C(=O)N1C1CCC(=O)NC1=O IICWMVJMJVXCLY-UHFFFAOYSA-N 0.000 claims 1
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N Glutarimide Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims 1
- UVSMNLNDYGZFPF-UHFFFAOYSA-N Pomalidomide Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)N1C1CCC(=O)NC1=O UVSMNLNDYGZFPF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
Claims (8)
1. 2,6-диоксопиперидин, выбранный из группы, состоящей из
(a) соединения формулы:
в которой один из X и Y представляет собой C=O, а другой из X и Y представляет собой C=O или CH2;
(1) каждый из R1, R2, R3 и R4 независимо от других представляет собой галогено, алкил из 1 - 4 атомов углерода или алкокси из 1 - 4 атомов углерода, или
(2) один из R1, R2, R3 и R4 представляет собой -NHR5, а оставшиеся из R1, R2, R3 и R4 представляют собой водород;
R5 представляет собой водород или алкил из 1 - 8 атомов углерода;
R6 представляет собой водород, алкил из 1 - 8 атомов углерода, бензил или галогено; при условии, что R6 другой, чем водород, если X и Y представляют собой C=O, и
(1) каждый из R1, R2, R3 и R4 представляет собой фтор,
или (2) один из R1, R2, R3 и R4 представляет собой аминогруппу;
(б) полученных присоединением кислоты солей указанных соединений, содержащих способный к приготовлению атом азота.
(a) соединения формулы:
в которой один из X и Y представляет собой C=O, а другой из X и Y представляет собой C=O или CH2;
(1) каждый из R1, R2, R3 и R4 независимо от других представляет собой галогено, алкил из 1 - 4 атомов углерода или алкокси из 1 - 4 атомов углерода, или
(2) один из R1, R2, R3 и R4 представляет собой -NHR5, а оставшиеся из R1, R2, R3 и R4 представляют собой водород;
R5 представляет собой водород или алкил из 1 - 8 атомов углерода;
R6 представляет собой водород, алкил из 1 - 8 атомов углерода, бензил или галогено; при условии, что R6 другой, чем водород, если X и Y представляют собой C=O, и
(1) каждый из R1, R2, R3 и R4 представляет собой фтор,
или (2) один из R1, R2, R3 и R4 представляет собой аминогруппу;
(б) полученных присоединением кислоты солей указанных соединений, содержащих способный к приготовлению атом азота.
2. Соединение по п.1, в котором каждый из R1, R2, R3 и R4 независимо от других представляют собой галогено, алкил из 1 - 4 атомов углерода или алкокси из 1 - 4 атомов углерода, и R6 представляет собой метил, этил или пропил.
3. Соединение по п. 1, в котором один из R1, R2, R3 и R4 представляет собой -NH2 и оставшиеся из R1, R2, R3 и R4 представляют собой водород, а R6 представляет собой метил, этил, пропил или бензил.
4. Соединение по п.1, которое представляет собой 1-оксо-2-(2,6-диоксопиперидин-3-ил)-5-аминоизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-4-аминоизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-6-аминоизоиндолил, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-7-аминоизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-4,5,6,7-тетрафторизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-4,5,6,7-тетрахлоризоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-4,5,6,7-тетраметилизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-4,5,6,7-тетраметоксиизоиндолин, 3-(1-оксо-4-аминоизоиндолин-1-ил)-3-метилпиперидин-2,6-дион, 3-(1-оксо-4-аминоизоиндолин-1-ил)-3-этилпиперидин-2,6-дион, 3-(1-оксо-4-аминоизоиндолин-1-ил)-3-пропилпиперидин-2,6-дион или 3-(3-аминофталимидо)-3-метилпиперидин-2,6-дион.
5. Способ снижения нежелательных уровней TNFα у млекопитающего, при котором ему вводят эффективное количество соединения по п.1.
6. Фармацевтическая композиция, содержащая количество соединения по п.1, достаточное при введении в режиме разовой дозы или, множественных доз снижения уровней TNFα у млекопитающего, в комбинации с носителем.
7. Способ снижения нежелательных уровней TNFα у млекопитающего, при котором ему вводят эффективное количество соединения формулы:
в которой в указанном соединении один из X и Y представляет собой C=O, а другой из X и Y представляет собой C=O или CH2.
в которой в указанном соединении один из X и Y представляет собой C=O, а другой из X и Y представляет собой C=O или CH2.
8. Способ по п.7, при котором указанное соединение представляет собой 1-оксо-2-(2,6-диоксопиперидин-3-ил)-5-аминоизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-4-аминоизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-6-аминоизоиндолин, 1-оксо-2-(2,6-диоксопиперидин-3-ил)-7-аминоизоиндолин, 1,3-диоксо-2-(2,6-диоксопиперидин-3-ил)-4-аминоизоиндолин или 1,3-диоксо-2-(2,6-диоксопиперидин-3-ил)-5-аминоизоиндолин.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/690,258 | 1996-07-24 | ||
| US08690258 US5635517B1 (en) | 1996-07-24 | 1996-07-24 | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
| US08/701,494 | 1996-08-22 | ||
| US60/048,278 | 1997-05-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99103124A true RU99103124A (ru) | 2001-01-27 |
| RU2177944C2 RU2177944C2 (ru) | 2002-01-10 |
Family
ID=24771755
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99103124/04A RU2595250C1 (ru) | 1996-07-24 | 1997-07-24 | Замещенные 2,6-диоксопиперидины, фармацевтическая композиция на их основе и способы снижения уровней tnf-альфа |
| RU99103124/04A RU2177944C2 (ru) | 1996-07-24 | 1997-07-24 | ЗАМЕЩЕННЫЕ 2,6-ДИОКСОПИПЕРИДИНЫ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ИХ ОСНОВЕ И СПОСОБЫ СНИЖЕНИЯ УРОВНЕЙ TNF-α |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99103124/04A RU2595250C1 (ru) | 1996-07-24 | 1997-07-24 | Замещенные 2,6-диоксопиперидины, фармацевтическая композиция на их основе и способы снижения уровней tnf-альфа |
Country Status (3)
| Country | Link |
|---|---|
| US (3) | US5635517B1 (ru) |
| ES (1) | ES2359778T3 (ru) |
| RU (2) | RU2595250C1 (ru) |
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| US20040091455A1 (en) | 2002-10-31 | 2004-05-13 | Zeldis Jerome B. | Methods of using and compositions comprising immunomodulatory compounds for treatment and management of macular degeneration |
| US7563810B2 (en) * | 2002-11-06 | 2009-07-21 | Celgene Corporation | Methods of using 3-(4-amino-1-oxo-1,3-dihydroisoindol-2-yl)-piperidine-2,6-dione for the treatment and management of myeloproliferative diseases |
-
1996
- 1996-07-24 US US08690258 patent/US5635517B1/en not_active Expired - Lifetime
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1997
- 1997-07-24 RU RU99103124/04A patent/RU2595250C1/ru active
- 1997-07-24 RU RU99103124/04A patent/RU2177944C2/ru not_active IP Right Cessation
- 1997-07-24 ES ES09151443T patent/ES2359778T3/es not_active Expired - Lifetime
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2001
- 2001-02-12 US US09/781,179 patent/US6555554B2/en not_active Expired - Lifetime
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2003
- 2003-01-06 US US10/337,602 patent/US7119106B2/en not_active Expired - Fee Related
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