Patent US5216176A successfully refreshed from Google Patents.
US5216176A
Expired / Lapsed
US
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7-alkoxycoumarins, dihydropsoralens, and benzodipyranones as photo-activated therapeutic agents and inhibitors of epidermal growth factor
Assignee: Nikon Corp
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Filing: 1990-12-21
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Granted: 1993-06-01
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Expires: 2010-12-21
Abstract
Abstract A photochemotherapeutic compound of the formula <IMAGE> wherein (i) n is zero, W is a (C1-16) alkyl, alkenyl, or alkynyl linear or branched chain hydrocarbon, having no more than four O, N, or S atoms in or attached to the chain; or (ii) n is 1, W is CR or CR2, and R, R', and R'' are independently H or CH3; or (iii) N is 2, W is CR or CR2, and R, R', and R'' are independently H or CH3; and A, B, C, and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, aryloxy, hydroxy, carboxy, haloalkyl, or haloalkoxy, particularly compounds of the foregoing structure in which W is a charged substiuent and n=0 or 1.
Inventors
- 👤 Ned D. Heindel
- 👤 Michele C. Jetter nee Siller
- 👤 Jeffrey D. Laskin
- 👤 Michael A. Gallo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 15:38
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
37 words
A photochemotherapeutic compound 4,8-dimethyl-7-(omega-carboxyheptyloxy) coumarin of the formula ##STR11## wherein W is (CH 2 ) 7 COOH; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 2
Dependent Claim
37 words
A photochemotherapeutic compound 4,8-dimethyl-7-(omega-carboxyheptyloxy) coumarin of the formula ##STR11## wherein W is (CH 2 ) 7 COOH; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 3
Dependent Claim
39 words
A photochemotherapeutic compound 4-methyl-8-iodo-7-(2-methyl-3-buten-2-yl)oxycoumarin of the formula ##STR12## wherein W is C(CH 3 ) 2 CH═CH 2 ; R 3 , R 5 and R 6 are hydrogen; R 4 is CH 3 ; and R 8 is I.
Claim 4
Dependent Claim
39 words
A photochemotherapeutic compound 4-methyl-8-iodo-7-(2-methyl-3-buten-2-yl)oxycoumarin of the formula ##STR12## wherein W is C(CH 3 ) 2 CH═CH 2 ; R 3 , R 5 and R 6 are hydrogen; R 4 is CH 3 ; and R 8 is I.
Claim 5
Dependent Claim
37 words
A photochemotherapeutic compound 7-(2-octyn-1-yl)oxycoumarin of the formula ##STR13## wherein W is CH 2 C.tbd.C(CH 2 ) 4 CH 3 ; and R 3 , R 4 , R 5 , R 6 and R 8 are hydrogen.
Claim 6
Dependent Claim
37 words
A photochemotherapeutic compound 7-(2-octyn-1-yl)oxycoumarin of the formula ##STR13## wherein W is CH 2 C.tbd.C(CH 2 ) 4 CH 3 ; and R 3 , R 4 , R 5 , R 6 and R 8 are hydrogen.
Claim 7
Dependent Claim
36 words
A photochemotherapeutic compound 4,8-dimethyl-7-ethoxycoumarin of the formula ##STR14## wherein W is CH 2 CH 3 ; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 8
Dependent Claim
36 words
A photochemotherapeutic compound 4,8-dimethyl-7-ethoxycoumarin of the formula ##STR14## wherein W is CH 2 CH 3 ; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 9
Dependent Claim
34 words
A photochemotherapeutic compound 4,8-dimethyl-7-methoxycoumarin of the formula ##STR15## wherein W is CH 3 ; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 10
Dependent Claim
34 words
A photochemotherapeutic compound 4,8-dimethyl-7-methoxycoumarin of the formula ##STR15## wherein W is CH 3 ; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 11
Dependent Claim
38 words
A photochemotherapeutic compound 4,8-dimethyl-7-butyloxycoumarin of the formula ##STR16## wherein W is (CH 2 ) 3 CH 3 ; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 12
Dependent Claim
38 words
A photochemotherapeutic compound 4,8-dimethyl-7-butyloxycoumarin of the formula ##STR16## wherein W is (CH 2 ) 3 CH 3 ; R 3 , R 5 and R 6 are hydrogen; and R 4 and R 8 are CH 3 .
Claim 13
Dependent Claim
71 words
A photochemotherapeutic compound of the formula: ##STR17## wherein W is selected from the group consisting of a C 1 to C 16 alkyl and alkenyl hydrocarbon chain substituted on said hydrocarbon chain with a polar functional moiety selected from the group consisting of hydroxyl, carboxyl and amino moieties; A, B, C, and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, aryloxy, hydroxy, carboxy, haloalkyl, or haloalkoxy.
Claim 14
Dependent Claim
71 words
A photochemotherapeutic compound of the formula: ##STR17## wherein W is selected from the group consisting of a C 1 to C 16 alkyl and alkenyl hydrocarbon chain substituted on said hydrocarbon chain with a polar functional moiety selected from the group consisting of hydroxyl, carboxyl and amino moieties; A, B, C, and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, aryloxy, hydroxy, carboxy, haloalkyl, or haloalkoxy.
Claim 15
Dependent Claim
87 words
A therapeutic agent having an extracellular activity on mammalian cells comprising a pharmaceutically acceptable carrier and a compound of the formula ##STR18## wherein W is selected from the group consisting of a C 1 to C 16 alkyl and alkenyl hydrocarbon chain permissively substituted on said hydrocarbon chain with a polar functional moiety selected from the group consisting of hydroxyl, carboxyl and amino moieties, and A, B, C and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, hydroxy, carboxy, haloalkyl or haloalkoxy.
Claim 16
Dependent Claim
87 words
A therapeutic agent having an extracellular activity on mammalian cells comprising a pharmaceutically acceptable carrier and a compound of the formula ##STR18## wherein W is selected from the group consisting of a C 1 to C 16 alkyl and alkenyl hydrocarbon chain permissively substituted on said hydrocarbon chain with a polar functional moiety selected from the group consisting of hydroxyl, carboxyl and amino moieties, and A, B, C and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, hydroxy, carboxy, haloalkyl or haloalkoxy.
Claim 17
Dependent Claim
24 words
A compound as recited in claim 7, wherein said compound is 4,8-dimethyl-7-(carboxymethyloxy) coumarin, wherein n=0, W=CH 2 COOH, B=CH 3 and D=CH 3 .
Claim 18
Dependent Claim
30 words
A compound as recited in claim 7, wherein said compound is 4,8-dimethyl-7-(2-N,N-dimethylaminoethoxy) coumarin, wherein n=0, W=CH 2 CH 2 N(CH 3 ) 2 , B=CH 3 and D=CH 3 .
Claim 19
Dependent Claim
35 words
A compound as recited in claim 7, wherein said compound is 4,8-dimethyl-7-(2-N,N,N-trimethylammonium ethoxy) coumarin iodide, wherein n=0, W=CH 2 CH 2 N(CH 3 ) 3 + I - , B=CH 3 and D=CH 3 .
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-05-31 | 1996-11-30 | 1997-06-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-05-31 | 2000-11-30 | 2001-06-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-05-31 | 2004-11-30 | 2005-06-01 | $7700.00 | Window Closed / Lapsed |