Phthalocyanine analogs

• US 20020128249A1
• Filed: 01/04/2002
• Published: 09/12/2002
• Est. Priority Date: 10/30/1997
• Status: Abandoned Application

• Current Assignee: Qinetiq Limited (QinetiQ Group PLC)
• Original Assignee: Qinetiq Limited (QinetiQ Group PLC)
• Inventors: Cook, Michael J.
• Application Number:
  US10/035,243
• Publication Number:
  US 20020128249A1
• Time in Patent Office: Days
• US Class Current: 514/185
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: B82Y 10/00 Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: C07D 487/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C09B 47/00 Porphines; Azaporphines non-dyeing compounds C07D487/22
• CPC Class Codes: C09K 19/3488 the heterocyclic ring having more than 6 members, e.g. macrocycles, phthalocyanines

Abstract

Disclosed are compounds of formula V

where M is a metal atom; a metal compound; 2H whereby one H is bonded to each of the two nitrogen atoms depicted as being bonded to M (positions 29 and 31 shown) R₃ is H or methyl; R₁ and R₄ are independently selected from: H, C₁ to C₄ alkyl, C₂ to C₄ alkenyl, methoxy, butoxy, propoxy, NH₂, NH—(C₁ to C₄ alkyl), N—(C₁ to C₄ alkyl)₂, S—(C₁ to C₄ alkyl); R₈ to R₂₅ are the same or different and are independently selected from: C₁ to C₃₂ alkyl; C₂ to C₃₂ alkenyl; X—O—Y; X-phenyl, X²COOX¹, X²CONR¹R¹¹, H; halide; where: X and X² are independently selected from: a chemical bond, —(CH₂)_n— where n is an integer from 1 to 32, —(CH₂)_a—CH═CH(CH₂)_b where a and b are independently selected from integers 0-32 and a+b totals 32; X¹ and Y are independently selected from: C₁ to C₃₂ alkyl, C₂ to C₃₂ alkenyl, and H; R¹ and R¹¹ are independently selected from: H; C₁ to C₃₂ alkyl, C₂ to C₃₂ alkenyl, —(CH₂)_n—; with the proviso that at least one of R₈ to R₂₅ is selected from: C₁ to C₃₂ alkyl, C₂ to C₃₂ alkenyl, X—O—Y, X-phenyl, X²COOX¹, X²CONR¹R¹¹.

Claims

1. A compound of Formula I (FIG. 1(b))

wherein:

M is selected from;

a metal atom;

a metal compound;

2H whereby one H is bonded to each of the two nitrogen atoms depicted as being bonded to M (positions 29 and 31 shown)

and wherein;

one or more of the Q groups is selected from;

formula II (FIG. 1(c)) or formula III (FIG. 1(d)), with the remaining Q groups each being formula IV (FIG. 1(e));

wherein;

R₃₃ and R₃₄ are independently selected from;

H or methyl

R₃₅ is selected from;

H;

C₁ to C₄ alkyl;

C₂ to C₄ alkenyl;

methoxy;

butoxy;

propoxy;

NH₂;

NH—

(C₁ to C₄ alkyl);

N—

(C₁ to C₄ alkyl)₂, S—

(C₁ to C₄ alkyl),

each R_n and R_p group is independently selected from;

C₁ to C₃₂ alkyl;

C₂ to C₃₂ alkenyl;

X—

O—

Y;

X-phenyl

X²COOX¹;

X²CONR¹R¹¹;

H;

halide

wherein;

X and X² are independently selected from;

a chemical bond;

—

(CH₂)_n—

wherein n is an integer from 1 to 32;

—

(CH₂)_a—

CH═

CH(CH₂)_b where a and b are independently selected from integers 0-32 and a+b totals 32.

X¹ and Y are independently selected from;

C₁ to C₃₂ alkyl;

C₂ to C₃₂ alkenyl;

H

R¹ and R¹¹ are independently selected from;

H;

C₁ to C₃₂ alkyl;

C₂ to C₃₂ alkenyl;

—

(CH₂)_n—

with the proviso that where more than one Q is Formula II with the remaining Q group being Formula IV, at least one group independently selected from;

R_33, R₃₄, R₃₅, an R_n group, an R_p group, is not H.

2. A compound as claimed in claim 1 having formula V (FIG. 1(f)),

Wherein:

M is selected from;

a metal atom, a metal compound;

2H whereby one H is bonded to each of the two nitrogen atoms depicted as being bonded to M (positions 29 and 31 shown)

R₃ is H or methyl

R₁ and R₄ are independently selected from;

H;

C₁ to C₄ alkyl;

C₂ to C₄ alkenyl;

methoxy;

butoxy;

propoxy;

NH₂;

NH—

(C₁ to C₄ alkyl);

N—

(C₁ to C₄ alkyl)₂, S—

(C₁ to C₄ alkyl),

R₈ to R₂₅ are the same or different and are independently selected from;

C₁ to C₃₂ alkyl;

C₂ to C₃₂ alkenyl;

X—

O—

Y;

X-phenyl

X²COOX¹;

X²CONR¹R¹¹;

H;

halide

and wherein X, X², X¹, Y, R¹ and R¹¹ are as defined in claim 1.

3. A compound as claimed in claim 1 or claim 2 wherein all non-peripheral R groups other than those attached to pyridyl nuclei are selected from:

H;

alkyl containing up to 32;

up to 20;

between 4-14;

or between 8-12 C atoms where 1 or more adjacent CH₂ groups may be replaced by O or a double bond, and the remaining R groups are all H.

4. A compound as claimed in claim 3 wherein all non-peripheral R groups are H.

5. A compound as claimed in any one of the preceding claims wherein all peripheral R groups other than those attached to pyridyl nuclei are selected from:

alkyl containing up to 32;

up to 20;

between 4-14;

between 8-12 C atoms, and the remaining R groups are all H.

6. A compound as claimed in any one of the preceding claims wherein R_33, R₃₄, R₁ and R₃are H.

7. A compound as claimed in any one of the preceding claims wherein R₃₅ and R₄ are electron donating groups independently selected from:

O-alkyl, NH₂, NH-alkyl, N(alkyl)₂, alkyl, S-alkyl.

8. A compound as claimed in any one of the preceding claims wherein those the alkyl groups present within R groups are straight chain alkyl.

9. A compound as claimed in any one of the preceding claims wherein M is selected from:

2H;

Ru, Ni, Pb, V, Pd, Co, Nb, Al, Sn, Zn, Cu, Mg, Ca, In, Ga, Fe, Eu, Lu and Ge.

10. A compound as claimed in claim 9 wherein M is selected from:

2H;

Zn;

Cu;

Co;

Ru; and

Ni.

11. A compound as claimed in claim 10 having formula VI (FIG. 1(g)) wherein M is selected from:

2H;

Zn;

Ni.

12. A compound as claimed in any one of the preceding claims which has an absorption maximum in the near infra-red.

13. A compound as claimed in any one of the preceding claims which is soluble.

14. A composition comprising a compound as claimed any one of the preceding claims.

15. A pharmaceutical composition comprising a compound of any one of claims 1 to 13 in admixture with a pharmaceutically acceptable carrier.

16. A compound of any one of claims 1 to 13 for use in PDT.

17. A compound of any one of claims 1 to 13 for use in the preparation of a medicament.

18. A compound as claimed in claim 16 or claim 17 wherein the PDT or the medicament is for the treatment of a mammal having a tumour susceptible to photodynamic treatment.

19. A method of treatment comprising the step of exposing a compound as claimed in any one of claims 1 to 13 to laser radiation.

20. Use of a compound of any one of claims 1 to 13 in an LC device.

21. An LC device comprising two spaced walls each bearing electrode structures and treated on at least one facing surface with an alignment layer comprising a compound as claimed in any one of claims 1 to 13.

22. An LC device as claimed in claim 21 which is an electro-optical display device.

23. Use of a compound of any one of claims 1 to 13 in an optical recording medium.

24. A method of storing or retrieving information comprising the step of exposing a compound as claimed in any one of claims 1 to 13 to laser radiation.

25. An optical recording medium comprising a recording layer, said layer comprising a compound as claimed in any one of claims 1 to 13.

27. An optical recording medium as claimed in claim 26 wherein the compound is a near infra-red absorber.

28. Use of a compound of any one of claims 1 to 13 in a gas sensor.

29. A method of detecting a gas in a sample comprising the step of exposing a compound as claimed in any one of claims 1 to 13 to the sample.

30. A gas sensor comprising a compound as claimed in any one of claims 1 to 13.

31. A gas sensor as claimed in claim 30 wherein the compound is present as a spin coated film.

32. An LB film comprising a compound as claimed in any one of claims 1 to 13.

33. A molecular wire comprising a compound as claimed in any one claims 1 to 13.

34. Use of a compound as claimed in any one of claims 1 to 13 in a Photonic device.

35. A Photonic device comprising a compound as claimed in any one of claims 1 to 13.

36. Use of a compound as claimed in claimed in any one of claims 1 to 13 in any one of the following:

electrocatalysis;

photocatalysis;

electric conduction;

photoconductivity;

electrochromism;

a photovoltaic cell;

a battery.

37. Use of a compound as claimed in any one of claims 1 to 13 in the production of a dimer.

38. A dimer or higher oligomer consisting of a compound as claimed in any one claims 1 to 13.

40. Use of a compound of any one of claims 1 to 13 in the production of a polymer.

41. A polymer consisting of a compound as claimed in any one of claims 1 to 13 in polymerised form.

43. A method of producing a compound as claimed in any one claims 1 to 13 essentially as described herein with reference to Example 1.

26. An optical recording medium as claimed 25 wherein the compound is present as a spin coated film.

39. A mixed dimer or higher oligomer comprising a compound as claimed in any one and a further Pc or Pc derivative.

42. An AzaPc essentially as described herein with reference to the accompanying Examples and Figures.