Title:
TRICARBONYL TECHNETIUM-99M OR RHENIUM-188 LABEL RING RGD DERIVATIVE, A PREPARATION METHOD THEREOF, AND A PHARMACEUTICAL COMPOSITION CONTAINING THE DERIVATIVE AS AN ACTIVE INGREDIENT FOR USE IN THE DIAGNOSIS OR TREATMENT OF ANGIOGENESIS-RELATED DISEASES
Document Type and Number:
WIPO Patent Application WO/2011/149250
Kind Code:
A2
Abstract:
The present invention relates to a tricarbonyl technetium-99m or rhenium-188 label ring RGD derivative, a preparation method thereof, and a pharmaceutical composition containing the derivative as an active ingredient for use in the diagnosis or treatment of angiogenesis-related diseases. The tricarbonyl technetium-99m or rhenium-188 label ring RGD derivative of the present invention has a high subnanomolar affinity to αvβ3 integrin (also called as a vitronectin receptor that is activated in an angiogenic action induced by a tumor, reflects a high tumor image after an animal in which cancer cells are transplanted received an initial intake of the tricarbonyl technetium-99m label ring RGD derivative, and acts exclusively upon cancer cells having selectively activated αvβ3 integrin because of a substantially low intake into the liver and intestines, compared to existing known radioactive isotope label ring RGD derivatives. These results show that the rhenium-188 label derivative, a therapeutic nuclide using the same precursor as used in the technetium-99m label, effectively inhibits the growth of a tumor and demonstrates therapeutic efficacy when administered via tail vein injection to an animal model of a tumor, compared to a case where only saline has been injected, thereby making it useful as a medicine for the diagnosis or treatment of angiogenesis-related diseases.
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Inventors:
LEE BYUNG CHUL (KR)
KIM SANG EUN (KR)
KIM JI SUN (KR)
MOON BYUNG SEOK (KR)
JUNG JAE HO (KR)
KIM SANG EUN (KR)
KIM JI SUN (KR)
MOON BYUNG SEOK (KR)
JUNG JAE HO (KR)
Application Number:
PCT/KR2011/003801
Publication Date:
December 01, 2011
Filing Date:
May 24, 2011
Export Citation:
Assignee:
SNU R&DB FOUNDATION (KR)
LEE BYUNG CHUL (KR)
KIM SANG EUN (KR)
KIM JI SUN (KR)
MOON BYUNG SEOK (KR)
JUNG JAE HO (KR)
LEE BYUNG CHUL (KR)
KIM SANG EUN (KR)
KIM JI SUN (KR)
MOON BYUNG SEOK (KR)
JUNG JAE HO (KR)
International Classes:
C07D273/06; A61K31/5395; A61K51/04; A61P35/00; C07D498/06; C07D498/16; G01N33/60
Foreign References:
| US20080219921A1 | 2008-09-11 |
Other References:
HAUBNER, R.; WESTER, H-J.; WEBER, W.A.; MANG, C.; ZIEGLER, S. I .; GOODMAN, S. L.; SENEKOWI TSCH-SCHMIDTKE, R.; KESSLER, H.; SCHWA, CANCER RES., vol. 61, 2001, pages 1781 - 1785
JEONG, J.M.; HONG, M.K; CHANG, Y.S.; LEE Y.S.; KIM, Y.J.; CHEON, G.J.; LEE, D.S.; CHUNG, J.K.; LEE, M ., J. NUCL MED., vol. 49, 2008, pages 830 - 836
CHEN, W.; PARK, R.; TOHME, M; SHAHINIAN, A.H. BADING, J.R.; ONT I, P.S., BIOCONJUGATE CHEM., vol. 15, 2004, pages 41 - 49
LIU, S.; HSIEH W.Y., KIM, Y.S.; MOHAMMEL, S. I., BIOCONJUGATE CHEM., vol. 16, 2005, pages 1580 - 1588
HAUBNER, R.; WESTER, H-J .; REUNING, U.; SENEKOWITSCH SCHMIDTKE, R.; DIEFENBACH, B.; KESSLER, H.; STOCKLIN G.; SCHWA IGER, M., J. NUCL . MED., vol. 40, 1999, pages 1061 - 1071
JANS SEN, M.; OYEN, W.J.G.; DIJKGRAAF, I.; MASSUGER, L.F.A.G.; FRIEL INK, C.; EDWARDS, D.S.; RAJO ADYHE, M.; BOONSTRA, H.; CORSTEN, CANCER RES., vol. 62, 2002, pages 6146 - 6151
WU, Y.; ZHANG, X.; XIONG, Z.; CHENG, Z.; FISHER, D.R.; LIU, S.; GAMBHIR, S.S.; CHEN, X., J. NUCL. MED., vol. 46, 2005, pages 1707 - 1718
ALBERTO, R.; SCHIBLI, R.; EGLI, A.; SCHUBIGER, A. P.; ABRAM, U.; ADEN, T.A., J. AM. CHEM. SOC., vol. 120, 1998, pages 7987 - 7988
ALBERTO, R.; SCHIBLI, R.; SCHUBIGER, A. P.; ABRAM, U.; PIETZSCH, H-P.; JOHANNSEN, B., J. AM. CHEM. SOC., vol. 121, 1999, pages 6076 - 6077
SCHIBLI, R; NETTER, M.; SCAPOZZA, L.; BIRRINGER, M.; SCHEL 1 ING, P.; DUMAS, C.; SCHOCH, J.; SCHUBIGER, P. A., J. ORGANOMET . CHEM., vol. 668, 2003, pages 67 - 74
SCHIBLI, R.; SCHWARZBACH, R.; ALBERTO, R.; ORTNER, K.; SCHMAL LE, H.; DUMAS, C.; EGLI, A.; SCHUBIGER, P. A., BIOCONJUATE CHEM., vol. 13, 2002, pages 750 - 756
HAUBNER, R.; WESTER, H-J.; REUNING, U.; SENEKOWI TSCH - SCHMIDT KE, R.; DIEFENBACH, B.; KESSLER, H.; STOCKLIN G.; SCHWA IGER, M., J. NUCL. MED., vol. 40, 1999, pages 1061 - 1071
ALBERTO, R.; SCHIBLI, R.; EGLI, A.; SCHUBIGER, A. P.; ABRAM, U; KADEN, T.A., J. AM. CHEM. SOC., vol. 120, 1998, pages 7987 - 7988
ALBERTO, R.; SCHIBLI, .; SCHUBIGER, A.P.; ABRAM, U.; PIETZSCH, H-P.; JOHANNSEN, B., J. AM. CHEM. SOC., vol. 121, 1999, pages 6076 - 6077
SCHIBLI, .; NETTER, M.; SCAPOZZA, L.; BIRR INGER, M.; SCHEL 1 ING, P.; DUMAS, C.; SCHOCH, J.; SCHUBIGER, P. A., J. ORGANOMET . CHEM., vol. 668, 2003, pages 67 - 74
See also references of EP 2583966A4
JEONG, J.M.; HONG, M.K; CHANG, Y.S.; LEE Y.S.; KIM, Y.J.; CHEON, G.J.; LEE, D.S.; CHUNG, J.K.; LEE, M ., J. NUCL MED., vol. 49, 2008, pages 830 - 836
CHEN, W.; PARK, R.; TOHME, M; SHAHINIAN, A.H. BADING, J.R.; ONT I, P.S., BIOCONJUGATE CHEM., vol. 15, 2004, pages 41 - 49
LIU, S.; HSIEH W.Y., KIM, Y.S.; MOHAMMEL, S. I., BIOCONJUGATE CHEM., vol. 16, 2005, pages 1580 - 1588
HAUBNER, R.; WESTER, H-J .; REUNING, U.; SENEKOWITSCH SCHMIDTKE, R.; DIEFENBACH, B.; KESSLER, H.; STOCKLIN G.; SCHWA IGER, M., J. NUCL . MED., vol. 40, 1999, pages 1061 - 1071
JANS SEN, M.; OYEN, W.J.G.; DIJKGRAAF, I.; MASSUGER, L.F.A.G.; FRIEL INK, C.; EDWARDS, D.S.; RAJO ADYHE, M.; BOONSTRA, H.; CORSTEN, CANCER RES., vol. 62, 2002, pages 6146 - 6151
WU, Y.; ZHANG, X.; XIONG, Z.; CHENG, Z.; FISHER, D.R.; LIU, S.; GAMBHIR, S.S.; CHEN, X., J. NUCL. MED., vol. 46, 2005, pages 1707 - 1718
ALBERTO, R.; SCHIBLI, R.; EGLI, A.; SCHUBIGER, A. P.; ABRAM, U.; ADEN, T.A., J. AM. CHEM. SOC., vol. 120, 1998, pages 7987 - 7988
ALBERTO, R.; SCHIBLI, R.; SCHUBIGER, A. P.; ABRAM, U.; PIETZSCH, H-P.; JOHANNSEN, B., J. AM. CHEM. SOC., vol. 121, 1999, pages 6076 - 6077
SCHIBLI, R; NETTER, M.; SCAPOZZA, L.; BIRRINGER, M.; SCHEL 1 ING, P.; DUMAS, C.; SCHOCH, J.; SCHUBIGER, P. A., J. ORGANOMET . CHEM., vol. 668, 2003, pages 67 - 74
SCHIBLI, R.; SCHWARZBACH, R.; ALBERTO, R.; ORTNER, K.; SCHMAL LE, H.; DUMAS, C.; EGLI, A.; SCHUBIGER, P. A., BIOCONJUATE CHEM., vol. 13, 2002, pages 750 - 756
HAUBNER, R.; WESTER, H-J.; REUNING, U.; SENEKOWI TSCH - SCHMIDT KE, R.; DIEFENBACH, B.; KESSLER, H.; STOCKLIN G.; SCHWA IGER, M., J. NUCL. MED., vol. 40, 1999, pages 1061 - 1071
ALBERTO, R.; SCHIBLI, R.; EGLI, A.; SCHUBIGER, A. P.; ABRAM, U; KADEN, T.A., J. AM. CHEM. SOC., vol. 120, 1998, pages 7987 - 7988
ALBERTO, R.; SCHIBLI, .; SCHUBIGER, A.P.; ABRAM, U.; PIETZSCH, H-P.; JOHANNSEN, B., J. AM. CHEM. SOC., vol. 121, 1999, pages 6076 - 6077
SCHIBLI, .; NETTER, M.; SCAPOZZA, L.; BIRR INGER, M.; SCHEL 1 ING, P.; DUMAS, C.; SCHOCH, J.; SCHUBIGER, P. A., J. ORGANOMET . CHEM., vol. 668, 2003, pages 67 - 74
See also references of EP 2583966A4
Attorney, Agent or Firm:
LEE, Won Hee (Sung-ji Heights II642-16 Yoksam-dong, Kangnam-ku, Seoul 135-080, KR)
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