WO2004005289B1 - Efficient synthesis of pyropheophorbide a and its derivatives - Google Patents

Efficient synthesis of pyropheophorbide a and its derivatives

Info

Publication number
WO2004005289B1
WO2004005289B1 PCT/US2003/021179 US0321179W WO2004005289B1 WO 2004005289 B1 WO2004005289 B1 WO 2004005289B1 US 0321179 W US0321179 W US 0321179W WO 2004005289 B1 WO2004005289 B1 WO 2004005289B1
Authority
WO
WIPO (PCT)
Prior art keywords
purpurin
treating
give
preparation
base
Prior art date
Application number
PCT/US2003/021179
Other languages
French (fr)
Other versions
WO2004005289A3 (en
WO2004005289A2 (en
Inventor
Ravindra K Pandey
Thomas J Dougherty
Alexander J Pallenberg
Original Assignee
Health Research Inc
Light Sciences Corp
Ravindra K Pandey
Thomas J Dougherty
Alexander J Pallenberg
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Health Research Inc, Light Sciences Corp, Ravindra K Pandey, Thomas J Dougherty, Alexander J Pallenberg filed Critical Health Research Inc
Priority to AU2003249742A priority Critical patent/AU2003249742A1/en
Priority to EP03763275A priority patent/EP1606291A2/en
Publication of WO2004005289A2 publication Critical patent/WO2004005289A2/en
Publication of WO2004005289A3 publication Critical patent/WO2004005289A3/en
Publication of WO2004005289B1 publication Critical patent/WO2004005289B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings

Abstract

A process for the preparation of pyropheophorbide a and its derivatives, including 3-devinyl-3-(1'-hexyloxy)ethyl-­pyropheophorbide-a, otherwise known as HPPH, is provided. The process involves treating chlorin e6, in the form of its trimethyl ester, with a base, followed by heating to give pyropheophorbide a, which is converted to HPPH by treatment with acid, followed by hexyl alcohol under basic conditions.

Claims

AMENDED CLAIMS[received by the International Bureau on 30 april 2004 (30.04.2004); original claim 1 amended; remaining claims unchanged (2 pages)]CLAIMS AMENDED UNDER ARTICLE 19(1) PCT:
1. A process for the preparation of methyl pheophorbide a, comprising treating chlorin e6 trimethyl ester with a base in an aromatic solvent having a boiling point greater than 120°C.
2. A process for the preparation of pyropheophorbide a, comprising:
(a) treating chlorin e6 trimethyl ester with a base in a high-boiling aromatic solvent to give methyl pheophorbide a; and (b) heating the methyl pheophorbide a to effect decarboxylation and saponification.
3. A process for the preparation of ether analogs of pyropheophorbide a, comprising:
(a) treating chlorin e6 trimethyl ester with a base in a high-boiling aromatic solvent to give methyl pheophorbide a;
(b) heating of the methyl pheophorbide a to effect decarboxylation and saponification to give pyropheophorbide a; and
(c) treating the pyropheophorbide with an acid, followed by an alcohol under basic conditions to effect addition of the alcohol across a vinyl group.
The process of claim 3, wherein the alcohol is 1-hexanol (n-hexyl alcohol).
5. A process for the preparation of purpurin- 18, comprising:
(a) treating chlorin e6 trimethyl ester with a base in an aromatic solvent in the presence of air to give purpurin- 18 ; and
(b) re-esterifying the resulting purpurin- 18.
6. A process for the preparation of ether analogs of purpurin-18, comprising:
(a) treating chlorin e6 trimethyl ester with a base in an aromatic solvent in the presence of air to give purpurin- 18;
(b) re-esterifying the purpurin-18; and - 18 -
(c) treating the re-esterified purpurin- 18 with an acid, followed by treating with an alcohol under basic conditions.
7. A process for the preparation of purpurimmides, comprising: (a) treating chlorin e6 trimethyl ester with a base in an aromatic solvent in the presence of air to give purpurin-18;
(b) re-esterifying the purpurin-18; and
(c) treating the re-esterified purpurin- 18 with a primary amine.
8. A process for the preparation of ether analogs of purpurinimides, comprising:
(a) treating chlorin e6 trimethyl ester with a base in an aromatic solvent in the presence of air to give purpurin- 18;
(b) re-esterifying the purpurin- 18 ;
(c) treating the re-esterified purpurin-18 with a primary amine to give a purpurinimide; and
(d) treating the resulting purpurinimide with an acid, followed by an alcohol under basic conditions.
544549; DCM; LP
PCT/US2003/021179 2002-07-02 2003-07-02 Efficient synthesis of pyropheophorbide a and its derivatives WO2004005289A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003249742A AU2003249742A1 (en) 2002-07-02 2003-07-02 Efficient synthesis of pyropheophorbide a and its derivatives
EP03763275A EP1606291A2 (en) 2002-07-02 2003-07-02 Efficient synthesis of pyropheophorbide a and its dervatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US39361702P 2002-07-02 2002-07-02
US60/393,617 2002-07-02

Publications (3)

Publication Number Publication Date
WO2004005289A2 WO2004005289A2 (en) 2004-01-15
WO2004005289A3 WO2004005289A3 (en) 2004-04-15
WO2004005289B1 true WO2004005289B1 (en) 2004-07-22

Family

ID=30115612

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/021179 WO2004005289A2 (en) 2002-07-02 2003-07-02 Efficient synthesis of pyropheophorbide a and its derivatives

Country Status (4)

Country Link
US (1) US7053210B2 (en)
EP (2) EP1606291A2 (en)
AU (1) AU2003249742A1 (en)
WO (1) WO2004005289A2 (en)

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AU2003249742A8 (en) 2004-01-23
AU2003249742A1 (en) 2004-01-23
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US20040044198A1 (en) 2004-03-04
US7053210B2 (en) 2006-05-30

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