US5252579A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Macrocyclic immunomodulators
Assignee: Wyeth LLC
•
Filing: 1993-02-16
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Granted: 1993-10-12
•
Expires: 2013-02-16
Abstract
Abstract This invention provides a compound of the structure ##STR1## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl, fluorine, trifluoromethyl, aryl, arylalkyl, or any pair taken together to form a 3-6 membered ring; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof which is useful as an immunosuppressive, antiinflamatory, antifungal, antiproliferative, and antitumor agent. This invention also covers derivatives of I and the use of I in combination with other immunoregulatory agents.
Inventors
- 👤 Jerauld S. Skotnicki
- 👤 Amedeo A. Failli
- 👤 Robert J. Steffan
- 👤 Robert M. Kearney
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 20:20
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/12; C07D498/18; A; A61; A61P; A61P37/00; A61P37/02; A61P37/06
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
283 words
A compound of the structure ##STR6## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
283 words
A compound of the structure ##STR6## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
30 words
The compound of claim 1 in which X is --NR 1 CR 2 CR 2 R 3 (CR 4 R 5 ) m S-- or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
37 words
The compound of claim 2 wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each, independently, hydrogen or alkyl of 1-6 carbon atoms or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
14 words
The compound of claim 1 which is 23,25-deepoxy-23,25-(2-aminoethanethio)rapamycin or a pharmaceutically acceptable salt thereof.
Claim 6
Independent Claim
304 words
A method of inducing immunosuppression in a mammal in need thereof which comprises, administering to said mammal an immunosuppressive amount of a compound of the structure ##STR7## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof.
Claim 7
Independent Claim
304 words
A method of inducing immunosuppression in a mammal in need thereof which comprises, administering to said mammal an immunosuppressive amount of a compound of the structure ##STR7## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
23 words
The method according to claim 5 wherein the induced immunosuppression is used to prevent or treat transplantation rejection or host versus graft disease.
Claim 9
Dependent Claim
23 words
The method according to claim 5 wherein the induced immunosuppression is used to treat autoimmune diseases, diseases of inflammation, or hyperproliferative vascular disorders.
Claim 10
Dependent Claim
296 words
A pharmaceutical composition which comprises an effective amount of a compound of the structure ##STR8## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof and a pharmaceutical carrier.
Claim 11
Dependent Claim
296 words
A pharmaceutical composition which comprises an effective amount of a compound of the structure ##STR8## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof and a pharmaceutical carrier.
Claim 12
Independent Claim
312 words
A method of inducing immunosuppression in a mammal which comprises administering to said mammal an immunosuppressive effective amount of a combustion of a compound of the structure ##STR9## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof and at least one other immunoregulatory agent.
Claim 13
Independent Claim
312 words
A method of inducing immunosuppression in a mammal which comprises administering to said mammal an immunosuppressive effective amount of a combustion of a compound of the structure ##STR9## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof and at least one other immunoregulatory agent.
Claim 14
Dependent Claim
33 words
The method according to claim 9 wherein the other immunoregulatory agent is selected from the group consisting of azathioprine, corticosteroids, such as prednisone and methylprednisone, cyclophosphamide, rapamycin, cyclosporin A, FK-506, OKT-3, and ATG.
Claim 15
Dependent Claim
302 words
A pharmaceutical composition which comprises an effective amount of a compound of the structure ##STR10## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof; at least one other immunoregulatory agents; and a pharmaceutical carrier.
Claim 16
Dependent Claim
302 words
A pharmaceutical composition which comprises an effective amount of a compound of the structure ##STR10## wherein X is selected from the group consisting of --NR 1 CR 2 R 3 (CR 4 R 5 ) m S--, --NR 1 CR 2 R 3 (CR 4 R 5 ) m O--, --OCR 2 R 3 (CR 4 R 5 ) m O--, --NR 1 CR 2 R 3 (CR 4 R 5 ) p --, --OCR 2 R 3 (CR 4 R 5 ) p --, --NR 1 CR 2 R 3 (CR 4 R 5 ) m NR 6 --, --OCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m NR 6 --, --SCR 2 R 3 (CR 4 R 5 ) m S--, --NOR 1 --, and --NR 1 --; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, fluorine, trifluoromethyl, aryl, arylalkyl or 7-10 carbon atoms, or any pair taken together to form a 3-6 membered ring, wherein the aryl moiety of the aryl and arylalkyl groups is selected from the group consisting of phenyl, naphthyl, pyridyl, quinolyl, isoquinolyl, quinoxalyl, thienyl, thionaphthyl, furyl, benzofuryl, benzodioxyl, benzoxazolyl, benzoisoxazolyl, and benzodioxolyl which may be optionally mono-, di-, or tri-substituted with a group selected from alkyl of 1-6 carbon atoms, arylalkyl of 7-10 carbon atoms, alkoxy of 1-6 carbon atoms, cyano, halo, nitro, carbalkoxy of 2-7 carbon atoms, trifluoromethyl, amino, dialkylamino of 1-6 carbon atoms per alkyl group, alkylthio of 1-6 carbon atoms, --SO 3 H, --PO 3 H, and --CO 2 H; m=1-6; and p=0-6 or a pharmaceutically acceptable salt thereof; at least one other immunoregulatory agents; and a pharmaceutical carrier.
Claim 17
Dependent Claim
33 words
The composition according to claim 11 wherein the other immunoregulatory agent is selected from the group consisting of azathioprine, corticosteroids, such as prednisone and methylprednisone, cyclophosphamide, rapamycin, cyclosporin A, FK-506, OKT-3, and ATG.
Claim 18
Dependent Claim
11 words
A compound which is 25,26-dehydro-24,25-secorapamycin or a base addition salt thereof.
Claim 19
Dependent Claim
11 words
A compound which is 25,26-dehydro-24,25-secorapamycin or a base addition salt thereof.
References Cited (Backward Citations)
US3929992A
Cited
US3993749A
Cited
US4885171A
Cited
US4316885A
Cited
US4401653A
Cited
US4650803A
Cited
US5100899A
Cited
US5130307A
Cited
US5078999A
Cited
US5080899A
Cited
US5120842A
Cited
US5120842B1
Cited
EP0507555A1
Cited
US5100883A
Cited
US5118678A
Cited
US5091389A
Cited
US5102876A
Cited
US5118677A
Cited
EP0525960A1
Cited
US5138051A
Cited
US5169851A
Cited
US5151413A
Cited
US5194447A
Cited
US5177203A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-10-11 | 1997-04-12 | 1997-10-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-10-11 | 2001-04-12 | 2001-10-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-10-11 | 2005-04-12 | 2005-10-12 | $7700.00 | Window Closed / Lapsed |