WO1997032885B1 - Synthese de l'isoimide de substances chlorees et bacteriochlorees et leur utilisation pour le diagnostic et le traitement du cancer - Google Patents
Synthese de l'isoimide de substances chlorees et bacteriochlorees et leur utilisation pour le diagnostic et le traitement du cancerInfo
- Publication number
- WO1997032885B1 WO1997032885B1 PCT/US1997/003891 US9703891W WO9732885B1 WO 1997032885 B1 WO1997032885 B1 WO 1997032885B1 US 9703891 W US9703891 W US 9703891W WO 9732885 B1 WO9732885 B1 WO 9732885B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- purpurin
- imide
- group
- alkyl
- derivative
- Prior art date
Links
- VZUHQRBBQSLSHS-SSZFMOIBSA-N Isoimide Chemical compound C1=CC(Br)=CC=C1\N=C/1C(CCCC2)=C2C(=O)O\1 VZUHQRBBQSLSHS-SSZFMOIBSA-N 0.000 title claims 3
- 206010028980 Neoplasm Diseases 0.000 title 1
- 150000004036 bacteriochlorins Chemical class 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 201000011510 cancer Diseases 0.000 title 1
- 150000004035 chlorins Chemical class 0.000 title 1
- 238000003745 diagnosis Methods 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 17
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 6
- 239000000126 substance Substances 0.000 claims abstract 6
- 125000000539 amino acid group Chemical group 0.000 claims abstract 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 229920000768 polyamine Polymers 0.000 claims abstract 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract 3
- 229920000570 polyether Polymers 0.000 claims abstract 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 3
- BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical class C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 claims 24
- -1 imide derivative of purpurin Chemical class 0.000 claims 21
- 238000000034 method Methods 0.000 claims 15
- 238000004519 manufacturing process Methods 0.000 claims 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 7
- 150000003949 imides Chemical class 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 150000001718 carbodiimides Chemical class 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 150000002678 macrocyclic compounds Chemical class 0.000 claims 4
- 150000008064 anhydrides Chemical group 0.000 claims 2
- BHPNXACHQYJJJS-UHFFFAOYSA-N bacteriochlorin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)CC2)=CC=C1C=C1CCC4=N1 BHPNXACHQYJJJS-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 claims 2
- 125000001033 ether group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 238000002428 photodynamic therapy Methods 0.000 abstract 1
Abstract
Composés pouvant servir de composés absorbant la lumière, tout particulièrement utiles dans le domaine de la thérapie photodynamique. De tels composés ont la formule (I) où z désigne =O ou NR14; où R14 représente alkyle ou alkyle substitué; où R1 est un groupe amino-acide, polyamine, polyéther ou bien OR13, où R13 est alkyle; R4 à R11 représentent -H, -OH, alkyle, alkylène ou bien -OR16, où R16 est H, alkyle, aryle, carbonyle ou bien un groupe contenant un carbonyle, à condition que R4 puisse être pris avec R5 pour former =O; que R6 puisse être pris avec R7 pour former =O; que R8 puisse être pris avec R9 pour former =O; que R10 puisse être pris avec R11 pour former =O; que R4 et R7 puissent former une liaison chimique; que R8 et R11 puissent former une liaison chimique; que R12 soit l'hydrogène ou un alkyle de faible masse moléculaire; et que si le premier z représente 0, le deuxième est NR14.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/613,134 | 1996-03-08 | ||
| US08/613,134 US5770730A (en) | 1996-03-08 | 1996-03-08 | Synthesis of carbodimide analogs of chlorins and bacteriochlorins and their use for diagnosis and treatment of cancer |
| US08/812,029 | 1997-03-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1997032885A1 WO1997032885A1 (fr) | 1997-09-12 |
| WO1997032885B1 true WO1997032885B1 (fr) | 1997-11-06 |
| WO1997032885A9 WO1997032885A9 (fr) | 1997-12-18 |
Family
ID=24456008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1997/003891 WO1997032885A1 (fr) | 1996-03-08 | 1997-03-07 | Synthese de l'isoimide de substances chlorees et bacteriochlorees et leur utilisation pour le diagnostic et le traitement du cancer |
Country Status (2)
| Country | Link |
|---|---|
| US (2) | US5770730A (fr) |
| WO (1) | WO1997032885A1 (fr) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE38994E1 (en) | 1988-07-20 | 2006-02-28 | Health Research, Inc. | Pyropheophorbides conjugates and their use in photodynamic therapy |
| USRE39094E1 (en) | 1988-07-20 | 2006-05-09 | Health Research, Inc. | Pyropheophorbides and their use in photodynamic therapy |
| US5952366A (en) * | 1996-03-08 | 1999-09-14 | Health Research, Inc. | Alkyl ether analogs of chlorins having an N-substituted imide ring |
| DK0945454T3 (da) * | 1996-10-01 | 2003-10-27 | Wyeth Lederle Japan Ltd | Iminochlorin-asparaginsyrederivater |
| CA2221912A1 (fr) * | 1997-11-21 | 1999-05-21 | David Dolphin | Agents photosensibilisants dont les proprietes de biodistribution et d'absorption de lumiere sont ameliorees |
| DE19814405C2 (de) | 1998-03-31 | 2000-03-02 | Schastak Astrid | Porphyrine und ihre Verwendung als Photosensitizer |
| US6602274B1 (en) * | 1999-01-15 | 2003-08-05 | Light Sciences Corporation | Targeted transcutaneous cancer therapy |
| AU2412800A (en) * | 1999-01-15 | 2000-08-01 | Light Sciences Corporation | Noninvasive vascular therapy |
| US6454789B1 (en) * | 1999-01-15 | 2002-09-24 | Light Science Corporation | Patient portable device for photodynamic therapy |
| EP1131100B1 (fr) * | 1999-01-15 | 2003-03-12 | Light Sciences Corporation | Compositions au traitement de troubles metaboliques osseux et de metastases osseuses contenant un agent photosensitive et un bisphosphonate |
| US6376483B1 (en) | 1999-05-27 | 2002-04-23 | Miravant Pharmaceuticals, Inc. | Bacteriochlorins and bacteriopurpurins useful as photoselective compounds for photodynamic therapy and a process for their production |
| US6534040B2 (en) | 1999-12-23 | 2003-03-18 | Health Research, Inc. | Chlorin and bacteriochlorin-based aminophenyl DTPA and N2S2 conjugates for MR contrast media and radiopharmaceuticals |
| US7897140B2 (en) * | 1999-12-23 | 2011-03-01 | Health Research, Inc. | Multi DTPA conjugated tetrapyrollic compounds for phototherapeutic contrast agents |
| US7078014B2 (en) * | 1999-12-23 | 2006-07-18 | Health Research, Inc. | Method for using chlorin and bacteriochlorin-based aminophenyl DTPA and N2S2 conjugates for MR contrast media and radiopharmaceuticals |
| US7166719B2 (en) * | 2002-06-27 | 2007-01-23 | Health Research, Inc. | Fluorinated photosensitizers related to chlorins and bacteriochlorins for photodynamic therapy |
| US7097826B2 (en) | 1999-12-23 | 2006-08-29 | Health Research, Inc. | Chlorin and bacteriochlorin-based difunctional aminophenyl DTPA and N2S2 conjugates for MR contrast media and radiopharmaceuticals |
| JP2003519670A (ja) * | 2000-01-12 | 2003-06-24 | ライト サイエンシーズ コーポレイション | 眼疾患の新規処置 |
| US6624187B1 (en) * | 2000-06-12 | 2003-09-23 | Health Research, Inc. | Long wave length absorbing bacteriochlorin alkyl ether analogs |
| WO2003061696A2 (fr) * | 2002-01-23 | 2003-07-31 | Light Sciences Corporation | Systemes et procedes pour une therapie photodynamique |
| US7053210B2 (en) * | 2002-07-02 | 2006-05-30 | Health Research, Inc. | Efficient synthesis of pyropheophorbide a and its derivatives |
| IL152900A0 (en) * | 2002-11-17 | 2003-06-24 | Yeda Res & Dev | Water-soluble bacteriochlorophyll derivatives and their pharmaceutical uses |
| US7057100B2 (en) * | 2003-06-26 | 2006-06-06 | The J.C. Robinson Seed Co. | Inbred corn line W23129 |
| MXPA06014326A (es) * | 2004-06-07 | 2007-02-19 | Yeda Res & Dev | Derivados de bacterioclorofila cationica y sus usos. |
| US7147840B2 (en) * | 2004-11-24 | 2006-12-12 | Health Research, Inc. | Oxo-bacteriopyropheophorbide-a carboxylic acid and esters thereof |
| EP1933941A2 (fr) | 2005-08-25 | 2008-06-25 | Philip R. Houle | Solutions sensibilisantes ameliorees, systemes, et procedes d'utilisation |
| CN101980609B (zh) * | 2008-02-19 | 2016-10-19 | 健康研究有限公司 | 用于光动力疗法和肿瘤成像的b环被还原-d环被氧化的四吡咯光敏剂 |
| US20110092961A1 (en) * | 2008-08-13 | 2011-04-21 | Searete Llc | Artificial cells |
| GB0819594D0 (en) | 2008-10-24 | 2008-12-03 | Univ Coimbrra | Process |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002962A (en) * | 1988-07-20 | 1991-03-26 | Health Research, Inc. | Photosensitizing agents |
| US5591847A (en) * | 1994-05-23 | 1997-01-07 | Health Research, Inc. | Long wavelength absorbing photosensitizers related to purpurin-18, bacteriopurpurin-18 and related compounds with imide linkages |
-
1996
- 1996-03-08 US US08/613,134 patent/US5770730A/en not_active Expired - Fee Related
-
1997
- 1997-03-06 US US08/812,029 patent/US5864035A/en not_active Expired - Fee Related
- 1997-03-07 WO PCT/US1997/003891 patent/WO1997032885A1/fr active Application Filing
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