Methods for preparing porphyrin-like compounds

Details Methods for preparing porphyrin-like compounds Methods for preparing porphyrin-like compounds

1993-06-15

1996-04-30

Shah, Mukund J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540145, C07D48722

Patent

active

055126758

ABSTRACT:
A method for synthesizing a porphocyanine having the formula: ##STR1## where each R is ethyl, comprises either: (1) treating 3,3'-4,4'-tetraethyl-5,5'-bisaminomethyl-2,2'-dipyrromethane with a 10-fold excess of DDQ or

REFERENCES:
patent: 4798891 (1989-01-01), Franck et al.
patent: 5051415 (1991-09-01), Morgan et al.
patent: 5124449 (1992-06-01), Franck et al.
patent: 5162509 (1992-11-01), Sessler et al.
Barnett et al., "Pyrrole chemistry. XII. Synthetic Approaches to Cyanopyrroles", Can J. Chem., 58, 409-411 (1979).
Demopoulos et al., "Pyrrole Chemistry. XXVI. A Synthesis of Porphobilinogen from Pyrrole", Can. J. Chem., 61, 2415-76 (1983).
Loader et al., "Pyrrole Chemistry. XXIII. The Cyanation of Substituted Pyrroles with Chlorosulfonyl Isocyanate (CSI). New Synthesie of Pyrrole-3-carbonitriles", Can. J. Chem., 59, 2673-76 (1981).
Dhar et al., "Recent Advances in the Chemistry of Chlorosulfonyl Isocyanate", Synthesis, 437-49 (1986).
Floyd et al., "Direct Cyanation of the Furan Nucleus by Chlorosulphonyl Isocyanate", Tetrahedron, 39, 3881-85 (1983): and
Vorbruggen, "Reaktive Isocyanate I. Die Direkte Einfuehrung von Nitril-Gruppen in Ungesattigte System. Eine Einfache Umwandlung von Carbonsauren in Ihre Nitrile", Tetrahedron Letters, 13, 1631-34 (1968).
"Photoradiation Therapy--Clinical and Drug Advances" and Intra-abdominal Applications of Hematoporphyrin Photoradiation Therapy, Porphyrin Photosensitization, 3-13, 15-21 (Kessel et al., eds 1983).
Broadhurst et al., "The Synthesis of 22 .pi.-Electron Macrocycles: Sapphyrins and Related Compounds", J. Amer. Chem. Soc. (1972) 1:2111-2116.
Bauer et al., "Sapphyrins: Novel Aromatic Pentapyrrolic Macrocycles", J. Amer. Chem. Soc. (1983) 105:6429-6436.
Day et al., "Large Metal Ion-Centered Template Reactions. A Uranyl Complex of Cyclopentakis(2-iminoisoindoline)", J. Amer. Chem. Soc. (1975) 97:4519-4527.
Marks et al., "Large Metal Ion-Centered Template Reactions. Chemical and Spectral Studies of the `Superphthalocyanine` Dioxocyclopentakis(1-iminoisoin-dilinato)uranium(VI) and Its Derivatives", J. Amer. Chem. Soc. (1978) 100:1695-1705.
Gossauer, A., "Syntheses of Some Unusual Polypyrrole Macrocycles", Bull. Soc. Chim. Belg. (1983) 92(9):793-795.
Sessler et al., "Rubyrin: A New Hexapyrrolic Expanded Porphyrin", Agnew, Chem. Int. Ed. Engl. (1991) 30(8):977-980.
Berger et al., "The Synthesis Of A 22.pi.-Electron Tetrapyrrolic Macrocycle, 1,3,1,3! Platyrin", Tetra. Lett. (1978) 44:4225-4228.
LeGoff et al., "Perchloro-7H-cycloprop a!acenaphthylene and the Percholorophenalenyl System", J. Org. Chem. (1987) 52:711-712.
Franck et al., "Chemical principles in the design of improved porphyrin photosensitizers", Proc. SPIE Int. Soc. Opt. Eng. (1988) 997:107-112.
Beckmann et al., " 22!Coproporphyrin II for Photodynamic Therapy", Agnew. Chem. Int. Ed. Engl. (1990) 29:1395-1397.
Gosmann et al., "Systhesis of a Fourfold Enlarged Porphyrin with an Extremely Large, Diamagnetic Ring-Current Effect", Agnew Chem. Int. Ed. Engl. (1986) 25:1100-1101.
Knubel et al., "Biomimetic Synthesis of an Octavinylogous Porphyrin with an Aromatic 34!Annulene System", Agnew. Chem. Int. Ed. Engl. (1988) 27:1170-1172.
Jux et al., "Acetylene-Cumulene Porphyrinoids", Agnew Chem. Int. Ed. Engl. (1990) 29:1385-1387.
Vogel et al., "Porphyrin Homologues: 22!Porphyrin(2.2.2.2), a `Stretched Porphycene`", Agnew Chem. Int. Ed. Engl. (1990) 29:1387-1390.
Sessler et al., "Synthesis and Crystal Structure of a Novel Tripyrrane-Containing Porphyrinogen-like Macrocycle", J. Org. Chem. (1987) 52:4394-4397.
Sessler et al., "An `Expanded Porphyrin`: The Synthesis and Structure of a New Aromatic Pentadentate Ligand", J. Am. Chem. Soc. (1988) 110:5586-5588.
Ssssler et al., "Synthesis and X-ray Characterization of a Uranyl(VI) Schiff Base Complex Derived from a 2:2 Condensation Product of 3,4-Diethylpyrrole-2,5-dicarbaldehyde and 1,2-Diamino-4,5-dimethyoxybenzene", Inorg. Chem. (1992) 31(4):529-531.
Gregorie, Jr., et al., "Hematoporphyrin-Derivative Fluorescense in Malignant Neoplasms", Ann. Surg. (1968) 167:820-828.
Diamond et al., "Photodynamic Therapy of Malignant Tumours", Lancet (1972) 2:1175-1177.
Dougherty et al., "Photoradiation Therapy for the Treatment of Malignant Tumors", Cancer Res. (1978) 38:2628.gtoreq.2635.
Regan et al., eds., The Science of Photomedicine (1992) Plenum Press, New York. The title page and table of contents is enclosed herewith.
Dougherty et al., "Photosensitizers", Cancer: Principles and Practice of Oncology, J. B. Lippincott Company, Philadelphia (1982) DeVita, Jr. et al. eds., Section 4, pp. 1836-1844.
Maiya et al., "In Vitro Photodynamic Activity of Diprotonated Sapphyrin: A 22-.pi.-Electron Pentapyrrolic Porphyrin-like Macrocycle", J. Phys. Chem. (1990) 94:3597-3601.
Sessler et al., "Tripyrroledimethine-derived (`texaphyrin`-type) macrocycles: Potential photosensitizers which absorb in the far-red spectral region", SPIE (1991) 1426:318-329.
Lauffer, R. B., "Paramagnetic Metal Complexes as Water Proton Relaxation Agents for NMR Imaging: Theory and Design", Chem. Rev. (1987) 87:901-927.
Kornguth et al., "Magnetic resonance imaging of gadolinium-labeled monoclonal antibody polymers directed at human T lymphocytes implanted in canine brain", J. Neurosurg. (1987) 66:898-906.
Koenig et al., "Magnetic Field Dependence (NMRD) profile of 1/T1 of Rabbit Kidney Medulla and Urine After Intravenous Injection of Gd(DTPA)", Invest Radiol. (1986) 21:697-704.
Cacheris et al., "Thermodynamic Study of Lanthanide Complexes of 1,4,7-Triazacyclononane-N,N',N"-triacetic Acid 1,4,7,10-tetraazacyclododecane-N,N',N",N"'-tetraacetoc Acid", Inorg. Chem. (1987) 26:958-960.
Loncin et al., "Coordination of Lanthanides by Two Polyamino Polycarboxylic Macrocycles: Formation of Highly Stable Lanthanide Complexes", Inorg. Chem. (1986) 25:2646-2648.
Chang et al., "Dissociation Kinetics of 1,10-Diaza-4,7,13,16-tetraoxacyclooctadecane-N,N'-diacetic Acid Complexes of Lanthanides", Inorg. Chem. (1987) 26:1981-1985.
Sessler et al., "A Water-Stable Gadolinium(III) Complex Dervied from A New Pentadentate `Expanded Porphyrin` Ligand", Inorg. Chem. (1989) 28:3390-3393.
Sessler et al., "Expanded Porphyrins", Top. Cur. Chem. (1992) 161:177-271.
Dolphin et al., "Porphocyanine: An Expanded Tetrapyrrolic Macrocycle," J. Am. Chem. Soc. 115, 9301-9302 (1993); and
WO 90/10633 published 20 Sep. 1990.
Marks et al, J. Amer. Chem. Soc., 100:6 pp. 1695-1704, 1978.
LeGoff et al., Tetrahedron Letters; No. 44; pp. 4225-4228., 1978.

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