US4334070A
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Cycloalka[4,5]pyrrolo[2,3-g]isoquinolines
Assignee: Hoffmann La Roche Inc
•
Filing: 1981-02-02
•
Granted: 1982-06-08
•
Expires: 2001-02-02
Abstract
Abstract Neuroleptically active cycloalka[4,5]pyrrolo[2,3-g]isoquinolines of the formula <IMAGE> A wherein n, R1, R2 and X are as hereinafter set forth, are described.
Inventors
- 👤 Leo Berger
- 👤 Gary L. Olson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:41
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04; C07D209/00; C07D209/56; C07D209/80; C07D209/82; C07D209/88; C07D217/00; C07D217/02; C07D217/04
Claims Analysis
Total Claims: 53
Claim 1
Independent Claim
617 words
A compound of the formula ##STR47## wherein R 1 is hydrogen; alkyl of 1 to 7 carbon atoms; alkanoyl of 1 to 7 carbon atoms; benzoyl; fluorobenzoyl; phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkyl amino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms; R 2 is hydrogen; alkyl of 1 to 7 carbon atoms; hydroxyalkyl of 1 to 7 carbon atoms; hydroxyalkyl of 1 to 7 carbon atoms bearing as a substituent phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; alkoxyalkyl wherein each alkyl group is of 1 to 7 carbon atoms; alkanoyloxy of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyloxy-alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyloxy-alkyl of 1 to 7 carbon atoms; alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms; phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms; alkenyl of 2 to 7 carbon atoms; cycloalkyl of 3 to 6 carbon atoms-alkyl of 2 to 7 carbon atoms; alkynyl of 2 to 7 carbon atoms; thienyl-alkyl of 1 to 7 carbon atoms; furylalkyl of 1 to 7 carbon atoms; phenylcarboxamido-alkyl of 1 to 7 carbon atoms; phenylcarboxamido-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; phenyl-alkenyl of 2 to 7 carbon atoms; phenyl-alkenyl of 2 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; alkenyloxy of 2 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; phenyl-alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 7 carbon atoms; phenyl-alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; phenyl-N-imidazolonylalkyl of 1 to 7 carbon atoms; or phenyl-N-imidazolonyl-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; X is O or S; and n is 3, 4, 5 or 6, or its pharmaceutically acceptable acid addition salt.
Claim 2
Dependent Claim
617 words
A compound of the formula ##STR47## wherein R 1 is hydrogen; alkyl of 1 to 7 carbon atoms; alkanoyl of 1 to 7 carbon atoms; benzoyl; fluorobenzoyl; phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkyl amino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms; R 2 is hydrogen; alkyl of 1 to 7 carbon atoms; hydroxyalkyl of 1 to 7 carbon atoms; hydroxyalkyl of 1 to 7 carbon atoms bearing as a substituent phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; alkoxyalkyl wherein each alkyl group is of 1 to 7 carbon atoms; alkanoyloxy of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyloxy-alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyloxy-alkyl of 1 to 7 carbon atoms; alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms; phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms; alkenyl of 2 to 7 carbon atoms; cycloalkyl of 3 to 6 carbon atoms-alkyl of 2 to 7 carbon atoms; alkynyl of 2 to 7 carbon atoms; thienyl-alkyl of 1 to 7 carbon atoms; furylalkyl of 1 to 7 carbon atoms; phenylcarboxamido-alkyl of 1 to 7 carbon atoms; phenylcarboxamido-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; phenyl-alkenyl of 2 to 7 carbon atoms; phenyl-alkenyl of 2 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; alkenyloxy of 2 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; phenyl-alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 7 carbon atoms; phenyl-alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; phenyl-N-imidazolonylalkyl of 1 to 7 carbon atoms; or phenyl-N-imidazolonyl-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; X is O or S; and n is 3, 4, 5 or 6, or its pharmaceutically acceptable acid addition salt.
Claim 3
Dependent Claim
9 words
A compound in accordance with claim 1, wherein X=O.
Claim 4
Dependent Claim
9 words
A compound in accordance with claim 1, wherein X=S.
Claim 5
Dependent Claim
9 words
A compound in accordance with claim 1, wherein n=3.
Claim 6
Dependent Claim
10 words
A compound in accordance with claim 4, which is trans.
Claim 7
Dependent Claim
168 words
A compound in accordance with claim 5, wherein R 1 is hydrogen; R 2 is alkyl of 1 to 7 carbon atoms; alkoxyalkyl wherein each alkyl group is of 1 to 7 carbon atoms; alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; or phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms.
Claim 8
Dependent Claim
9 words
A compound in accordance with claim 6, wherein X=O.
Claim 9
Dependent Claim
18 words
A compound in accordance with claim 7, wherein R 2 is alkyl of 1 to 7 carbon atoms.
Claim 10
Dependent Claim
23 words
A compound in accordance with claim 7, wherein R 2 is alkoxyalkyl wherein each alkyl group is of 1 to 7 carbon atoms.
Claim 11
Dependent Claim
39 words
A compound in accordance with claim 7, wherein R 2 is alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; or 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms.
Claim 12
Dependent Claim
64 words
A compound in accordance with claim 7, wherein R 2 is phenyloxy-alkyl of 1 to 7 carbon atoms; or phenyloxy-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms.
Claim 13
Dependent Claim
65 words
A compound in accordance with claim 7, wherein R 2 is phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or dialkylamino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms.
Claim 14
Dependent Claim
8 words
A compound in accordance with claim 7, 2-methyl-1,2,3,4,4a,5,7,8,9,10a-decahydro-4a,10a-trans-6H-cyclopenta[4,5]pyrrolo[2,3-g]isoquinolin-10(10H)-one.
Claim 15
Dependent Claim
8 words
A compound in accordance with claim 7, 2-[4-(4-fluorophenyl)-4-oxobutyl]-1,2,3,4,4a,5,7,8,9,10a-decahydro-4a,10a-trans-6H-cyclopenta[4,5]pyrrolo[2,3-g]isoquinolin-10(10H)-one.
Claim 16
Dependent Claim
8 words
A compound in accordance with claim 7, 2-(2-phenylethyl)-1,2,3,4,4a,5,7,8,9,10a-decahydro-4a,10a-trans-6H-cyclopenta[4,5]pyrrolo[2,3-g]isoquinolin-10(10H)-one.
Claim 17
Dependent Claim
9 words
A compound in accordance with claim 6, wherein X=S.
Claim 18
Dependent Claim
18 words
A compound in accordance with claim 16, wherein R 2 is alkyl of 1 to 7 carbon atoms.
Claim 19
Dependent Claim
39 words
A compound in accordance with claim 16, wherein R 2 is alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; or 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms.
Claim 20
Dependent Claim
8 words
A compound in accordance with claim 16, 2-methyl-1,2,3,4,4a,5,7,8,9,10a-decahydro-4a,10a-trans-6H-cyclopenta[4,5]pyrrolo[2,3-g]isoquinolin-10(10H)-thione.
Claim 21
Dependent Claim
9 words
A compound in accordance with claim 1, wherein n=4.
Claim 22
Dependent Claim
10 words
A compound in accordance with claim 20 which is trans.
Claim 23
Dependent Claim
167 words
A compound in accordance with claim 21, wherein R 1 is hydrogen; R 2 is alkyl of 1 to 7 carbon atoms, alkoxyalkyl wherein each alkyl is of 1 to 7 carbon atoms, alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; or phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms.
Claim 24
Dependent Claim
9 words
A compound in accordance with claim 22, wherein X=O.
Claim 25
Dependent Claim
18 words
A compound in accordance with claim 23, wherein R 2 is alkyl of 1 to 7 carbon atoms.
Claim 26
Dependent Claim
39 words
A compound in accordance with claim 23, wherein R 2 is alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; or 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms.
Claim 27
Dependent Claim
65 words
A compound in accordance with claim 23, wherein R 2 is phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or dialkylamino of 1 to 7 carbon atoms wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms.
Claim 28
Dependent Claim
8 words
A compound in accordance with claim 23, 2-methyl-2,3,4,4a,5,6,7,8,9,10,11a-decahydro-4a,11a-trans-1H,6H-cyclohexa[4,5]pyrrolo[2,3-g]isoquinolin-11(11H)-one.
Claim 29
Dependent Claim
8 words
A compound in accordance with claim 23, 2-[4-(4-fluorophenyl)-4-oxobutyl]-2,3,4,4a,5,7,8,9,10,11a-decahydro-4a,11a-trans-1H,6H-cyclohexa[4,5]pyrrolo[2,3-g]isoquinolin-11(11H)-one.
Claim 30
Dependent Claim
8 words
A compound in accordance with claim 23, 2-(2-phenylethyl)-2,3,4,4a,5,7,8,9,10,11a-decahydro-4a,11a-trans-1H,6H-cyclohexa[4,5]pyrrolo[2,3-g]isoquinolin-11(11H)-one.
Claim 31
Dependent Claim
9 words
A compound in accordance with claim 22, wherein X=S.
Claim 32
Dependent Claim
18 words
A compound in accordance with claim 30, wherein R 2 is alkyl of 1 to 7 carbon atoms.
Claim 33
Dependent Claim
38 words
A compound in accordance with claim 30, wherein R 2 is alkanoyl of 1 to 7 carbon atoms--alkyl of 1 to 7carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; or 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms.
Claim 34
Dependent Claim
9 words
A compound in accordance with claim 1, wherein n=5.
Claim 35
Dependent Claim
10 words
A compound in accordance with claim 33 which is trans.
Claim 36
Dependent Claim
168 words
A compound in accordance with claim 34, wherein R 1 is hydrogen; R 2 is alkyl of 1 to 7 carbon atoms, alkoxyalkyl wherein each alkyl group is of 1 to 7 carbon atoms; alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; or phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms.
Claim 37
Dependent Claim
9 words
A compound in accordance with claim 35, wherein X=O.
Claim 38
Dependent Claim
18 words
A compound in accordance with claim 36, wherein R 2 is alkyl of 1 to 7 carbon atoms.
Claim 39
Dependent Claim
39 words
A compound in accordance with claim 36, wherein R 2 is alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; or 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms.
Claim 40
Dependent Claim
8 words
A compound in accordance with claim 35, 2-methyl-1,2,3,4,4a,5,7,8,9,10,11,12a-dodecahydro-4a,12a-trans-6H-cyclohepta[4,5]pyrrolo[2,3-g]isoquinolin-12(12H)-one.
Claim 41
Dependent Claim
9 words
A compound in accordance with claim 35, wherein X=S.
Claim 42
Dependent Claim
18 words
A compound in accordance with claim 40, wherein R 2 is alkyl of 1 to 7 carbon atoms.
Claim 43
Dependent Claim
9 words
A compound in accordance with claim 1, wherein n=6.
Claim 44
Dependent Claim
10 words
A compound in accordance with claim 42, which is trans.
Claim 45
Dependent Claim
168 words
A compound in accordance with claim 43, wherein R 2 is hydrogen; R 2 is alkyl of 1 to 7 carbon atoms; alkoxyalkyl wherein each alkyl group is of 1 to 7 carbon atoms; alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; 4-fluorobenzoyl-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms; phenyloxy-alkyl of 1 to 7 carbon atoms wherein phenyl is substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms; or phenyl or phenyl substituted by halogen, trifluoromethyl, alkyl of 1 to 7 carbon atoms, alkoxy of 1 to 7 carbon atoms, nitro, amino, alkylamino of 1 to 7 carbon atoms or di-alkylamino of 1 to 7 carbon atoms, wherein phenyl or substituted phenyl is linked to an alkylene of 1 to 4 carbon atoms.
Claim 46
Dependent Claim
9 words
A compound in accordance with claim 44, wherein X=O.
Claim 47
Dependent Claim
18 words
A compound in accordance with claim 45, wherein R 2 is alkyl of 1 to 7 carbon atoms.
Claim 48
Dependent Claim
39 words
A compound in accordance with claim 45, wherein R 2 is alkanoyl of 1 to 7 carbon atoms-alkyl of 1 to 7 carbon atoms; benzoyl-alkyl of 1 to 7 carbon atoms; or 4-fluorobenzoyl-alkyl of 1 to 7 -carbon atoms.
Claim 49
Dependent Claim
8 words
A compound in accordance with claim 44, 2-methyl-2,3,4,4a,5,7,8,9,10,11,12,13a-dodecahydro-4a,13a-trans-1H,6H-cycloocta[4,5]pyrrolo[2,3-g]isoquinolin-13(13H)-one.
Claim 50
Dependent Claim
9 words
A compound in accordance with claim 44, wherein X=S.
Claim 51
Dependent Claim
19 words
A compound in accordance with claim 48, wherein R 2 is alkyl alkyl of 1 to 7 carbon atoms.
Claim 52
Dependent Claim
14 words
A compound of the formula ##STR48## wherein n is 3, 4, 5 or 6.
Claim 53
Dependent Claim
14 words
A compound of the formula ##STR48## wherein n is 3, 4, 5 or 6.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-06-07 | 1985-12-07 | 1986-06-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-06-07 | 1989-12-07 | 1990-06-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-06-07 | 1993-12-07 | 1994-06-08 | $7700.00 | Window Closed / Lapsed |