CA2361806A1 - Substituted 1-oxo- and 1,3-dioxoisoindolines and their use in pharmaceutical compositions for reducing inflammatory cytokine levels - Google Patents
Substituted 1-oxo- and 1,3-dioxoisoindolines and their use in pharmaceutical compositions for reducing inflammatory cytokine levels Download PDFInfo
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- CA2361806A1 CA2361806A1 CA002361806A CA2361806A CA2361806A1 CA 2361806 A1 CA2361806 A1 CA 2361806A1 CA 002361806 A CA002361806 A CA 002361806A CA 2361806 A CA2361806 A CA 2361806A CA 2361806 A1 CA2361806 A1 CA 2361806A1
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- amino
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- 102000004127 Cytokines Human genes 0.000 title claims abstract 6
- 108090000695 Cytokines Proteins 0.000 title claims abstract 6
- 230000002757 inflammatory effect Effects 0.000 title claims abstract 6
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 title claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 241000124008 Mammalia Species 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims 47
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 230000033115 angiogenesis Effects 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229940124622 immune-modulator drug Drugs 0.000 claims 3
- 239000002955 immunomodulating agent Substances 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- YYJRIODZWRNGBD-UHFFFAOYSA-N 2-(1-amino-3-oxo-1h-isoindol-2-yl)pentanedioic acid Chemical compound C1=CC=C2C(N)N(C(CCC(O)=O)C(O)=O)C(=O)C2=C1 YYJRIODZWRNGBD-UHFFFAOYSA-N 0.000 claims 1
- GMZFKVRMIVHGOK-UHFFFAOYSA-N 2-(4-methyl-1,3-dioxoisoindol-2-yl)pentanedioic acid Chemical compound CC1=CC=CC2=C1C(=O)N(C(CCC(O)=O)C(O)=O)C2=O GMZFKVRMIVHGOK-UHFFFAOYSA-N 0.000 claims 1
- WHGCSJYLVKPHSS-UHFFFAOYSA-N 2-(4-nitro-1,3-dioxoisoindol-2-yl)pentanedioic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(C(CCC(=O)O)C(O)=O)C(=O)C2=C1 WHGCSJYLVKPHSS-UHFFFAOYSA-N 0.000 claims 1
- DVFZIZCDDQITQV-UHFFFAOYSA-N 2-(7-amino-3-oxo-1h-isoindol-2-yl)pentanedioic acid Chemical compound NC1=CC=CC2=C1CN(C(CCC(O)=O)C(O)=O)C2=O DVFZIZCDDQITQV-UHFFFAOYSA-N 0.000 claims 1
- QGAAJLZWQIATLL-UHFFFAOYSA-N 2-(7-nitro-3-oxo-1h-isoindol-2-yl)butanedioic acid Chemical group O=C1N(C(CC(=O)O)C(O)=O)CC2=C1C=CC=C2[N+]([O-])=O QGAAJLZWQIATLL-UHFFFAOYSA-N 0.000 claims 1
- RZPMMKDWVZJPMQ-UHFFFAOYSA-N 2-(7-nitro-3-oxo-1h-isoindol-2-yl)pentanedioic acid Chemical compound O=C1N(C(CCC(=O)O)C(O)=O)CC2=C1C=CC=C2[N+]([O-])=O RZPMMKDWVZJPMQ-UHFFFAOYSA-N 0.000 claims 1
- XYCTTXSUXYHEGZ-UHFFFAOYSA-N 4-amino-2-(4-amino-1,3-dioxoisoindol-2-yl)-4-oxobutanoic acid Chemical compound C1=CC(N)=C2C(=O)N(C(CC(=O)N)C(O)=O)C(=O)C2=C1 XYCTTXSUXYHEGZ-UHFFFAOYSA-N 0.000 claims 1
- ZBHPQUIXKJDGPF-UHFFFAOYSA-N 4-amino-2-(7-nitro-3-oxo-1h-isoindol-2-yl)-4-oxobutanoic acid Chemical compound O=C1N(C(CC(=O)N)C(O)=O)CC2=C1C=CC=C2[N+]([O-])=O ZBHPQUIXKJDGPF-UHFFFAOYSA-N 0.000 claims 1
- GPDJMQUTEMESRJ-UHFFFAOYSA-N 4-amino-3-(1-amino-3-oxo-1h-isoindol-2-yl)-4-oxobutanoic acid Chemical compound C1=CC=C2C(N)N(C(CC(O)=O)C(N)=O)C(=O)C2=C1 GPDJMQUTEMESRJ-UHFFFAOYSA-N 0.000 claims 1
- UIVFLBUIBBTROC-UHFFFAOYSA-N 4-amino-3-(7-amino-3-oxo-1h-isoindol-2-yl)-4-oxobutanoic acid Chemical compound O=C1N(C(CC(O)=O)C(=O)N)CC2=C1C=CC=C2N UIVFLBUIBBTROC-UHFFFAOYSA-N 0.000 claims 1
- PJDGSDCRBKAJDH-UHFFFAOYSA-N 4-amino-3-(7-nitro-3-oxo-1h-isoindol-2-yl)-4-oxobutanoic acid Chemical compound O=C1N(C(CC(O)=O)C(=O)N)CC2=C1C=CC=C2[N+]([O-])=O PJDGSDCRBKAJDH-UHFFFAOYSA-N 0.000 claims 1
- HNVVLGMTFHERFZ-UHFFFAOYSA-N 4-amino-3-methyl-2-(4-nitro-1,3-dioxoisoindol-2-yl)-4-oxobutanoic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(C(C(C)C(N)=O)C(O)=O)C(=O)C2=C1 HNVVLGMTFHERFZ-UHFFFAOYSA-N 0.000 claims 1
- XSKMMEVRGHPMSJ-UHFFFAOYSA-N 5-amino-2-(4-amino-1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid Chemical compound C1=CC(N)=C2C(=O)N(C(CCC(=O)N)C(O)=O)C(=O)C2=C1 XSKMMEVRGHPMSJ-UHFFFAOYSA-N 0.000 claims 1
- CASOMQVHZDICDH-UHFFFAOYSA-N 5-amino-2-(4-methyl-1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid Chemical compound CC1=CC=CC2=C1C(=O)N(C(CCC(N)=O)C(O)=O)C2=O CASOMQVHZDICDH-UHFFFAOYSA-N 0.000 claims 1
- XMKUEWQZKLDLQQ-UHFFFAOYSA-N 5-amino-2-(4-nitro-1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(C(CCC(=O)N)C(O)=O)C(=O)C2=C1 XMKUEWQZKLDLQQ-UHFFFAOYSA-N 0.000 claims 1
- JWXSMBGQHOFVJT-UHFFFAOYSA-N 5-amino-2-(7-nitro-3-oxo-1h-isoindol-2-yl)-5-oxopentanoic acid Chemical compound O=C1N(C(CCC(=O)N)C(O)=O)CC2=C1C=CC=C2[N+]([O-])=O JWXSMBGQHOFVJT-UHFFFAOYSA-N 0.000 claims 1
- IFDZOMVNICEWHH-UHFFFAOYSA-N 5-amino-4-(4-nitro-1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid Chemical compound C1=CC([N+]([O-])=O)=C2C(=O)N(C(CCC(O)=O)C(=O)N)C(=O)C2=C1 IFDZOMVNICEWHH-UHFFFAOYSA-N 0.000 claims 1
- MUVQMLOEDIDSDJ-UHFFFAOYSA-N 5-amino-4-(7-nitro-3-oxo-1h-isoindol-2-yl)-5-oxopentanoic acid Chemical compound O=C1N(C(CCC(O)=O)C(=O)N)CC2=C1C=CC=C2[N+]([O-])=O MUVQMLOEDIDSDJ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- JVYMXRZSOURPSE-UHFFFAOYSA-N 5-amino-4-(4-amino-1,3-dioxoisoindol-2-yl)-5-oxopentanoic acid Chemical group C1=CC(N)=C2C(=O)N(C(CCC(O)=O)C(=O)N)C(=O)C2=C1 JVYMXRZSOURPSE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
1-Oxo- and 1,3-dioxoisoindolines substituted in the 4- or 5-position of the indoline ring reduce the levels of inflammatory cytokines such as TNF.alpha. in a mammal. A typical embodiment is 4-(4-amino-1,3-dioxoisoindolin-2-yl)-4- carbamoylbutanoic acid.
Claims (47)
1. A compound selected from the group consisting of a 1,3-dioxoisoindoline of the formula:
in which:
the carbon atom designated C* constitutes a center of chirality when n is not zero and when R1 is not R2;
one of X1 and X2 is nitro, alkyl of one to six carbons, or NH-Z, and the other of X1 or X2 is hydrogen;
each of R1 and R2 independent of the other, is hydroxy or NH-Z;
R3 is hydrogen, alkyl of one to six carbons, or halo;
Z is hydrogen, aryl, an acyl of one to six carbons, or an alkyl of one to six carbons;
and n has a value of 0, 1, or 2;
provided that if one of X1 and X2 is nitro, and n is 1 or 2, then R1 and R2 are other than hydroxy; and the salts thereof.
in which:
the carbon atom designated C* constitutes a center of chirality when n is not zero and when R1 is not R2;
one of X1 and X2 is nitro, alkyl of one to six carbons, or NH-Z, and the other of X1 or X2 is hydrogen;
each of R1 and R2 independent of the other, is hydroxy or NH-Z;
R3 is hydrogen, alkyl of one to six carbons, or halo;
Z is hydrogen, aryl, an acyl of one to six carbons, or an alkyl of one to six carbons;
and n has a value of 0, 1, or 2;
provided that if one of X1 and X2 is nitro, and n is 1 or 2, then R1 and R2 are other than hydroxy; and the salts thereof.
2. A compound according to claim 1 in which R1 is hydroxy; R2 is amino; R3 is hydrogen; and n is 1 or 2.
3. A compound according to claim 1 in which R1 is amino; R2 is hydroxy; R3 is hydrogen; and n is 1 or 2.
4. The compound according to claim 1 which is 1-(4-nitro-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid.
5. The compound according to claim 1 which is 1-(4-methyl-1,3-dioxoisoindolin-2-yl)propane-1,3-dicarboxylic acid.
6. The compound according to claim 1 which is 4-(4-nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid.
7. The compound according to claim 1 which is 2-(4-methyl-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid.
8. The compound according to claim 1 which is 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-3-carbamoylbutanoic acid.
9. The compound according to claim 1 which is 2-(4-amino-1,3-dioxoisoindolin-2-yl)-3-carbamoylpropanoic acid.
10. The compound according to claim 1 which is 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid.
11. The compound according to claim 1 which is 2-(4-amino-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid.
12. The method of reducing undesirable levels of inflammatory cytokines in a mammal which comprises administering thereto an effective amount of a compound according to claim 1.
13. A pharmaceutical composition comprising a quantity of a compound according to claim 1 sufficient upon administration in a single or multiple dose regimen to reduce levels of inflammatory cytokines in a mammal in combination with a carrier.
14. A compound selected from the group consisting of a 1-oxoisoindoline of the formula:
in which:
the carbon atom designated C* constitutes a center of chirality when n is not zero and R1 is not R2;
one of X1 and X2 is amino, nitro, alkyl of one to six carbons, or NH-Z, and the other of X1 or X2 is hydrogen;
each of R1 and R2 independent of the other, is hydroxy or NH-Z;
R3 is alkyl of one to six carbons, halo, or hydrogen;
Z is hydrogen, aryl, an acyl of one to six carbons, or an alkyl of one to six carbons;
n has a value of 0, 1, or 2;
provided that if one of X1 and X2 is amino or nitro, one of X1 and X2 is hydrogen, and n is 1 or 2, then R1 and R2 are not both hydroxy; and the salts thereof.
in which:
the carbon atom designated C* constitutes a center of chirality when n is not zero and R1 is not R2;
one of X1 and X2 is amino, nitro, alkyl of one to six carbons, or NH-Z, and the other of X1 or X2 is hydrogen;
each of R1 and R2 independent of the other, is hydroxy or NH-Z;
R3 is alkyl of one to six carbons, halo, or hydrogen;
Z is hydrogen, aryl, an acyl of one to six carbons, or an alkyl of one to six carbons;
n has a value of 0, 1, or 2;
provided that if one of X1 and X2 is amino or nitro, one of X1 and X2 is hydrogen, and n is 1 or 2, then R1 and R2 are not both hydroxy; and the salts thereof.
15. A compound according to claim 14 in which R1 is hydroxy; R2 is amine; R3 is hydrogen; and n is 1 or 2.
16. A compound according to claim 14 in which R1 is amine; R2 is hydroxy; R3 is hydrogen; and n is 1 or 2.
17. The compound according to claim 14 which is 2-(4-nitro-1-oxoisoindolin-2-yl)glutaric acid.
18. The compound according to claim 14 which is 2-(4-nitro-1-oxoisoindolin-2-yl)-4-carbamoylbutanoic acid.
19. The compound according to claim 14 which is 4-(4-nitro-1-oxoisoindolin-2-yl)-4-carbamoylbutanoic acid.
20. The compound according to claim 14 in which the 1-oxo-isoindoline is 2-(4-nitro-1-oxoisoindolin-2-yl)succinic acid.
21. The compound according to claim 14 which is 2-(4-nitro-1-oxoisoindolin-2-yl)-3-carbamoylpropanoic acid.
22. The compound according to claim 14 which is 3-(4-nitro-1-oxoisoindolin-2-yl)-3-carbamoylpropanoic acid.
23. The compound according to claim 14 which is 3-(4-amino-1-oxoisoindolin-2-yl)-3-carbamoylpropanoic acid.
24. The compound according to claim 14 which is 3-(3-amino-1-oxoisoindolin-2-yl)-3-carbamoylpropanoic acid.
25. The compound according to claim 14 which is 2-(4-amino-1-oxoisoindolin-2-yl)glutaric acid.
26. The compound according to claim 14 which is 2-(3-amino-1-oxoisoindolin-2-yl)glutaric acid.
27. The method of reducing undesirable levels of inflammatory cytokines in a mammal which comprises administering thereto an effective amount of a compound according to claim 14.
28. A pharmaceutical composition comprising a quantity of a compound according to claim 14 sufficient upon administration in a single or multiple dose regimen to reduce levels of inflammatory cytokines in a mammal in combination with a carrier.
29. The method of inhibiting TNF.alpha., which comprises administering a compound according to claim 1, wherein one of X1 and X2 is amino.
30. A method of using the compound according to claim 1 as an immunomodulating drug, wherein one of X1 and X2 is amino.
31. A method of using the compound according to claim 1 as an immunomodulating drug.
32. A method of using the compound according to claim 1 to inhibit undesirable angiogenesis.
33. A method of using the compound according to claim 14 to inhibit undesirable angiogenesis.
34. A method of using the compound according to claim 1 to inhibit undesirable angiogenesis, wherein one of X1 and X2 is amino.
35. A method of using the compound according to claim 14 to inhibit undesirable angiogenesis, wherein one of X1 and X2 is amino.
36. A method of using the compound according to claim 1 to treat cancer.
37. A method of using the compound according to claim 14 to treat cancer.
38. A method of using the compound according to claim 1 to treat cancer, wherein one of X1 and X2 is amino.
39. A method of using the compound according to claim 14 to treat cancer, wherein one of X1 and X2 is amino.
40. A method of using the compound according to claim 1 to inhibit TMF.alpha.
in a mammal, wherein one of X1 and X2 is alkyl.
in a mammal, wherein one of X1 and X2 is alkyl.
41. A method of using the compound according to claim 1 as an immunomodulating drug, wherein one of X1 and X2 is alkyl.
42. A method of using the compound according to claim 1 to inhibit undesirable angiogenesis, wherein one of X1 and X2 is alkyl.
43. A method of using the compound according to claim 14 to inhibit undesirable angiogenesis, wherein one of X1 and X2 is alkyl.
44. A method of using the compound according to claim 1 to treat cancer, wherein one of X1 and X2 is alkyl.
45. A method of using the compound according to claim 14 to treat cancer, wherein one of X1 and X2 is alkyl.
46. The compound according to claim 1, which is a substantially chirally pure (R)-isomer, a substantially chirally pure (S)-isomer, or a mixture thereof.
47. The compound according to claim 14 which is a substantially chirally pure (R)-isomer, a substantially chirally pure (S)-isomer, or a mixture thereof.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12494299P | 1999-03-18 | 1999-03-18 | |
| US60/124,942 | 1999-03-18 | ||
| PCT/US2000/007029 WO2000055134A1 (en) | 1999-03-18 | 2000-03-17 | Substituted 1-oxo- and 1,3-dioxoisoindolines and their use in pharmaceutical compositions for reducing inflammatory cytokine levels |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2361806A1 true CA2361806A1 (en) | 2000-09-21 |
| CA2361806C CA2361806C (en) | 2012-03-13 |
Family
ID=22417530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2361806A Expired - Fee Related CA2361806C (en) | 1999-03-18 | 2000-03-17 | Substituted 1-oxo- and 1,3-dioxoisoindolines and their use in pharmaceutical compositions for reducing inflammatory cytokine levels |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6380239B1 (en) |
| EP (1) | EP1163219B1 (en) |
| JP (1) | JP4728487B2 (en) |
| KR (1) | KR100672892B1 (en) |
| CN (1) | CN1342146A (en) |
| AT (1) | ATE306469T1 (en) |
| AU (1) | AU771015B2 (en) |
| BR (1) | BR0010042A (en) |
| CA (1) | CA2361806C (en) |
| CZ (1) | CZ20013338A3 (en) |
| DE (1) | DE60023123T2 (en) |
| DK (1) | DK1163219T3 (en) |
| ES (1) | ES2250121T3 (en) |
| FI (1) | FI119881B (en) |
| HK (1) | HK1042494A1 (en) |
| HU (1) | HUP0200499A3 (en) |
| NO (2) | NO320028B1 (en) |
| NZ (1) | NZ513953A (en) |
| RU (1) | RU2001121987A (en) |
| TR (1) | TR200102688T2 (en) |
| TW (1) | TWI229074B (en) |
| WO (1) | WO2000055134A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009039635A1 (en) * | 2007-09-24 | 2009-04-02 | Painceptor Pharma Corporation | Methods of modulating neurotrophin-mediated activity |
Families Citing this family (109)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6228879B1 (en) * | 1997-10-16 | 2001-05-08 | The Children's Medical Center | Methods and compositions for inhibition of angiogenesis |
| US5629327A (en) | 1993-03-01 | 1997-05-13 | Childrens Hospital Medical Center Corp. | Methods and compositions for inhibition of angiogenesis |
| US6429221B1 (en) * | 1994-12-30 | 2002-08-06 | Celgene Corporation | Substituted imides |
| US6518281B2 (en) * | 1995-08-29 | 2003-02-11 | Celgene Corporation | Immunotherapeutic agents |
| HU228769B1 (en) * | 1996-07-24 | 2013-05-28 | Celgene Corp | Substituted 2(2,6-dioxopiperidin-3-yl)phthalimides and -1-oxoisoindolines and their use for production of pharmaceutical compositions for mammals to reduce the level of tnf-alpha |
| US5635517B1 (en) * | 1996-07-24 | 1999-06-29 | Celgene Corp | Method of reducing TNFalpha levels with amino substituted 2-(2,6-dioxopiperidin-3-YL)-1-oxo-and 1,3-dioxoisoindolines |
| US7629360B2 (en) * | 1999-05-07 | 2009-12-08 | Celgene Corporation | Methods for the treatment of cachexia and graft v. host disease |
| US6458810B1 (en) | 2000-11-14 | 2002-10-01 | George Muller | Pharmaceutically active isoindoline derivatives |
| AU2002253795B2 (en) * | 2000-11-30 | 2007-02-01 | The Children's Medical Center Corporation | Synthesis of 4-Amino-Thalidomide enantiomers |
| US7091353B2 (en) | 2000-12-27 | 2006-08-15 | Celgene Corporation | Isoindole-imide compounds, compositions, and uses thereof |
| WO2003014315A2 (en) * | 2001-08-06 | 2003-02-20 | The Children's Medical Center Corporation | Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs |
| US7498171B2 (en) | 2002-04-12 | 2009-03-03 | Anthrogenesis Corporation | Modulation of stem and progenitor cell differentiation, assays, and uses thereof |
| US20100129363A1 (en) * | 2002-05-17 | 2010-05-27 | Zeldis Jerome B | Methods and compositions using pde4 inhibitors for the treatment and management of cancers |
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