US4977177A
Expired / Lapsed
US
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Tetrapyrrole polyaminomonocarboxylic acid therapeutic agents
Assignee: PORPHYRIN PRODUCTS Inc A CORP OF UTAH
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Filing: 1985-04-30
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Granted: 1990-12-11
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Expires: 2005-04-30
Abstract
Abstract This invention relates to new therapeutic compositions which are useful in photodiagnosis and phototherapy, especially in the detection and treatment of tumors and cancerous tissues in the human or animal body. The compounds of the present new therapeutic composition are mono-, di or polyamides of an amino monocarboxylic acid and a tetrapyrrole containing at least one carboxyl group of the structure <IMAGE> wherein Z is the aminomonocarboxylic acid residue less the amino group, X is the tetrapyrrole residue less the carboxy group, and "n" is an integer from 1 to 4 inclusive.
Inventors
- 👤 Jerry C. Bommer
- 👤 Bruce F. Burnham
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:46
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/40; A61K31/409; A61P; A61P35/00; A61P43/00; C; C07; C07D; C07D487/00; C07D487/22
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
233 words
A therapeutic composition for the detection and treatment of tumors sensitive thereto comprising a therapeutically effective amount of a fluorescent mono, di or polyamide of a aminomonocarboxylic acid and a tetrapyrrole compound of the formula: ##STR17## or the corresponding di- or tetrahydrotetrapyrroles wherein R 1 is methyl; ##STR18## R 2 is H, vinyl, ethyl, ##STR19## acetyl, ##STR20## CH 2 CH 2 CO 2 H, or ═CHCHO; R 3 is methyl ##STR21## R 4 is H, vinyl, ethyl, ##STR22## CH 2 CH 2 CO 2 H, ═CHCHO; or ##STR23## R 5 is methyl; R 6 is H, CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R or CO 2 H; R 7 is CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R, or ##STR24## R 8 is methyl or ##STR25## R 9 is H, COOH, CH 2 COOH or methyl; provided that when R 1 , R 2 , R 3 , R 4 , R 7 and R 8 represent two substituents or are divalent and attached to the same carbon, the respective pyrrole ring to which attached is a dihydropyrrole; R is lower alkyl or benzyl; R 6 and R 9 , taken together are ##STR26## with the proviso that at least one of R 1 -R 9 includes a free carboxyl group, or salts thereof; and a pharmaceutically acceptable carrier therefor.
Claim 2
Dependent Claim
233 words
A therapeutic composition for the detection and treatment of tumors sensitive thereto comprising a therapeutically effective amount of a fluorescent mono, di or polyamide of a aminomonocarboxylic acid and a tetrapyrrole compound of the formula: ##STR17## or the corresponding di- or tetrahydrotetrapyrroles wherein R 1 is methyl; ##STR18## R 2 is H, vinyl, ethyl, ##STR19## acetyl, ##STR20## CH 2 CH 2 CO 2 H, or ═CHCHO; R 3 is methyl ##STR21## R 4 is H, vinyl, ethyl, ##STR22## CH 2 CH 2 CO 2 H, ═CHCHO; or ##STR23## R 5 is methyl; R 6 is H, CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R or CO 2 H; R 7 is CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R, or ##STR24## R 8 is methyl or ##STR25## R 9 is H, COOH, CH 2 COOH or methyl; provided that when R 1 , R 2 , R 3 , R 4 , R 7 and R 8 represent two substituents or are divalent and attached to the same carbon, the respective pyrrole ring to which attached is a dihydropyrrole; R is lower alkyl or benzyl; R 6 and R 9 , taken together are ##STR26## with the proviso that at least one of R 1 -R 9 includes a free carboxyl group, or salts thereof; and a pharmaceutically acceptable carrier therefor.
Claim 3
Dependent Claim
12 words
The composition according to claim 1 wherein the tetrapyrrole is a porphyrin.
Claim 4
Dependent Claim
14 words
Composition according to claim 1 wherein the tetrapyrrole is a bacteriochlorin, di- or triamide.
Claim 5
Dependent Claim
16 words
Composition according to claim 1 wherein the amide-containing substituents are asymmetrically arranged on the tetrapyrrole molecule.
Claim 6
Dependent Claim
16 words
Composition according to claim 1 wherein the amide-containing substituents are asymmetrically arranged on the tetrapyrrole molecule.
Claim 7
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is diserinyl mesoporphyrin IX.
Claim 8
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is diglycyl mesoporphyrin IX.
Claim 9
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-α-(DL)-alanyl mesoporphyrin IX.
Claim 10
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-β-alanyl mesoporphyrin IX.
Claim 11
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-ε-amino-n-caproyl mesoporphyrin IX.
Claim 12
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is diglycyl trans-mesochlorin IX.
Claim 13
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is diglycyl trans-mesochlorin e 6 .
Claim 14
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is diglycyl mesochlorin e 4 .
Claim 15
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is diglycyl hematoporphyrin IX.
Claim 16
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is diglycyl chlorin e 6 .
Claim 17
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is diglycyl protoporphyrin IX.
Claim 18
Dependent Claim
11 words
Composition according to claim 1 wherein the amide is diglycyl deuteroporphyrin.
Claim 19
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-α-(DL)-alanyl trans-mesochlorin IX.
Claim 20
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-α-(DL)-alanyl mesochlorin e 6 .
Claim 21
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-α-(DL)-alanyl mesochlorin e 4 .
Claim 22
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-α-(DL)-alanyl hematoporphyrin IX.
Claim 23
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-α-(DL)-alanyl chlorin e 6 .
Claim 24
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-α-(DL)-alanyl protoporphyrin IX.
Claim 25
Dependent Claim
11 words
Composition according to claim 1 wherein the amide di-α-(DL)-alanyl deuteroporphyrin. is
Claim 26
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-β-DL)-alanyl trans-mesochlorin IX.
Claim 27
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-β-DL)-alanyl mesochlorin e 6 .
Claim 28
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-β-(DL)-alanyl mesochlorin e 4 .
Claim 29
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-β-(DL)-alanyl hematoporphyrin IX.
Claim 30
Dependent Claim
13 words
Composition according to claim 1 wherein the amide is di-β-(DL)-chlorin e 6 .
Claim 31
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-β-(DL)-alanyl protoporphyrin IX.
Claim 32
Dependent Claim
11 words
Composition according to claim 1 wherein the amide is di-β-(DL)-alanyl deuteroporphyrin.
Claim 33
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-L-α-serinyl chlorin e 6 .
Claim 34
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-L-α-serinyl trans-mesochlorin e 6 .
Claim 35
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-L-α-serinyl trans-mesochlorin IX.
Claim 36
Dependent Claim
14 words
Composition according to claim 1 wherein the amide is di-L-α-serinyl trans-mesochlorin e 4 .
Claim 37
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-L-α-serinyl hematoporphyrin IX.
Claim 38
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-L-α-serinyl protoporphyrin IX.
Claim 39
Dependent Claim
12 words
Composition according to claim 1 wherein the amide is di-L- α-serinyl deuteroporphyrin.
Claim 40
Dependent Claim
11 words
Composition according to claim 1 wherein the amide is di-ε-amino-n-caproyl-hematoporphyrin IX.
Claim 41
Dependent Claim
13 words
Composition according to claim 1 wherein the amide is di-ε-amino-n-caproyl-chlorin e 6 .
Claim 42
Dependent Claim
11 words
Composition according to claim 1 wherein the amide is di-ε-amino-n-caproyl-protoporphyrin IX.
Claim 43
Dependent Claim
10 words
Composition according to claim 1 wherein the amide is di-ε-amino-n-caproyl-deuteroporphyrin.
Claim 44
Independent Claim
257 words
A method for detecting tumors sensitive thereto in a mammal comprising administering to said mammal a therapeutically effective amount of fluorescent mono, di or polyamide of an aminomonocarboxylic acid and a tetrapyrrole compound of the formula: ##STR27## or the corresponding di- or tetrahydrotetrapyrroles wherein R 1 is methyl; ##STR28## R 2 is H, vinyl, ethyl, ##STR29## acetyl, ##STR30## CH 2 CH 2 CO 2 H, or ═CHCHO; R 3 is methyl ##STR31## R 4 is H, vinyl, ethyl, ##STR32## CH 2 CH 2 CO 2 H, ═CHCHO; or ##STR33## R 5 is methyl; R 6 is H, CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R or CO 2 H; R 7 is CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R, or ##STR34## R 8 is methyl or ##STR35## R 9 is H, COOH, CH 2 COOH or methyl; provided that when R 1 , R 2 , R 3 , R 4 , R 7 and R 8 represent two substituents or are divalent and attached to the same carbon, the respective pyrrole ring to which attached is a dihydropyrrole; R is lower alkyl or benzyl; R 6 and R 9 , taken together are ##STR36## with the proviso that at least one of R 1 -R 9 includes a free carboxyl group, or salts thereof; applying light of sufficient wavelength to activate said mono-, di- or polyamide to the area of the mammal to be examined; and observing the emitted fluorescence from said tumor.
Claim 45
Independent Claim
257 words
A method for detecting tumors sensitive thereto in a mammal comprising administering to said mammal a therapeutically effective amount of fluorescent mono, di or polyamide of an aminomonocarboxylic acid and a tetrapyrrole compound of the formula: ##STR27## or the corresponding di- or tetrahydrotetrapyrroles wherein R 1 is methyl; ##STR28## R 2 is H, vinyl, ethyl, ##STR29## acetyl, ##STR30## CH 2 CH 2 CO 2 H, or ═CHCHO; R 3 is methyl ##STR31## R 4 is H, vinyl, ethyl, ##STR32## CH 2 CH 2 CO 2 H, ═CHCHO; or ##STR33## R 5 is methyl; R 6 is H, CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R or CO 2 H; R 7 is CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R, or ##STR34## R 8 is methyl or ##STR35## R 9 is H, COOH, CH 2 COOH or methyl; provided that when R 1 , R 2 , R 3 , R 4 , R 7 and R 8 represent two substituents or are divalent and attached to the same carbon, the respective pyrrole ring to which attached is a dihydropyrrole; R is lower alkyl or benzyl; R 6 and R 9 , taken together are ##STR36## with the proviso that at least one of R 1 -R 9 includes a free carboxyl group, or salts thereof; applying light of sufficient wavelength to activate said mono-, di- or polyamide to the area of the mammal to be examined; and observing the emitted fluorescence from said tumor.
Claim 46
Dependent Claim
22 words
A method for detecting tumors according to claim 43 wherein light from 360-760 nanometers is used for the diagnosis of the tumor.
Claim 47
Independent Claim
257 words
A method for treating tumors sensitive thereto in a mammal comprising administering to said mammal a therapeutically effective amount of a fluorescent mono, di or polyamide of an aminomonocarboxylic acid and a tetrapyrrole compound of the formula: ##STR37## or the corresponding di- or tetrahydrotetrapyrroles wherein R 1 is methyl; ##STR38## R 2 is H, vinyl, ethyl, ##STR39## acetyl, ##STR40## CH 2 CH 2 CO 2 H, or ═CHCHO; R 3 is methyl, ##STR41## R 4 is H, vinyl, ethyl, ##STR42## CH 2 CH 2 CO 2 H, ═CHCHO; or ##STR43## R 5 is methyl; R 6 is H, CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R or CO 2 H; R 7 is CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R, or ##STR44## R 8 is methyl or ##STR45## R 9 is H, COOH, CH 2 COOH or methyl; provided that when R 1 , R 2 , R 3 , R 4 , R 7 and R 8 represent two substituents or are divalent and attached to the same carbon, the respective pyrrole ring to which attached is a dihydropyrrole; R is lower alkyl or benzyl; R 6 and R 9 , taken together are ##STR46## with the proviso that at least one of R 1 -R 9 includes a free carboxyl group, or salts thereof; and applying light of sufficient wavelength and intensity to activate said mono-, di- or polyamide, whereby said mono-, di- or polyamide exerts a cell-killing effect on such tumor.
Claim 48
Independent Claim
257 words
A method for treating tumors sensitive thereto in a mammal comprising administering to said mammal a therapeutically effective amount of a fluorescent mono, di or polyamide of an aminomonocarboxylic acid and a tetrapyrrole compound of the formula: ##STR37## or the corresponding di- or tetrahydrotetrapyrroles wherein R 1 is methyl; ##STR38## R 2 is H, vinyl, ethyl, ##STR39## acetyl, ##STR40## CH 2 CH 2 CO 2 H, or ═CHCHO; R 3 is methyl, ##STR41## R 4 is H, vinyl, ethyl, ##STR42## CH 2 CH 2 CO 2 H, ═CHCHO; or ##STR43## R 5 is methyl; R 6 is H, CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R or CO 2 H; R 7 is CH 2 CH 2 CO 2 H, CH 2 CH 2 CO 2 R, or ##STR44## R 8 is methyl or ##STR45## R 9 is H, COOH, CH 2 COOH or methyl; provided that when R 1 , R 2 , R 3 , R 4 , R 7 and R 8 represent two substituents or are divalent and attached to the same carbon, the respective pyrrole ring to which attached is a dihydropyrrole; R is lower alkyl or benzyl; R 6 and R 9 , taken together are ##STR46## with the proviso that at least one of R 1 -R 9 includes a free carboxyl group, or salts thereof; and applying light of sufficient wavelength and intensity to activate said mono-, di- or polyamide, whereby said mono-, di- or polyamide exerts a cell-killing effect on such tumor.
Claim 49
Dependent Claim
22 words
A method for treating tumors according to claim 45 whereby light from 620-760 nanometers is used for the treatment of the tumor.
References Cited (Backward Citations)
US4393071A
Cited
DE2809093A1
Cited
JPS5677280A
Cited
JPS58981A
Cited
WO1984001382A1
Cited
US4649151A
Cited
EP0118913A2
Cited
EP0168831A2
Cited
EP0168832A2
Cited
US4675338A
Cited
US4693885A
Cited
US4656186A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-12-10 | 1994-06-11 | 1994-12-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-10 | 1998-06-11 | 1998-12-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-10 | 2002-06-11 | 2002-12-11 | $7700.00 | Window Closed / Lapsed |