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US4517200A Expired / Lapsed US ⏱️ 0.0 years remaining

Method for treating allergic reactions with forskolin

Assignee: Merck Sharp & Dohme LLC
•
Filing: 1983-10-17
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Granted: 1985-05-14
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Expires: 2003-10-17
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Abstract

Abstract Forskolin and its disclosed derivatives are useful as antiallergic agents. Certain of the derivatives are novel.

Inventors

  • 👤 William Kreutner
  • 👤 Michael J. Green
  • 👤 Ho-Jane Shue
  • 👤 Anil K. Saksena

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 20:33
CPC Classifications
C; C07; C07D; C07D409/00; C07D409/02; C07D409/04; A; A61; A61P; A61P11/00; A61P11/08; A61P27/00; A61P27/02; A61P27/14; A61P37/00; A61P37/08; C07D311/00; C07D311/02; C07D311/78; C07D311/92

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 526 words
A compound having structural formula I: ##STR16## wherein R 1 is hydrogen and R 2 is ═O, H, or OR 11 wherein R 11 is H, alkanoyl having from 1 to 6 carbon atoms or ##STR17## --CO--(CH 2 ) m wherein m is 0, 1, 2 or 3 and Y is hydrogen, halogen, alkyl having from 1 to 6 carbon atoms, alkoxy having from 1 to 6 carbon atoms, alkylthio having from 1 to 6 carbon atoms, OH, CF 3 , NO 2 , CN, phenyl, benzyl, phenoxy or NR a R b wherein R a and R b are the same or different and are H or alkyl having from 1 to 6 carbon atoms; or R 2 may be SO 3 OR' or OR' wherein R' is alkyl having from 1 to 6 carbon atoms; R 3 is hydrogen; alkyl having from 1 to 10 carbon atoms; CH 2 OH; CHO; CO 2 R 15 wherein R 15 is H or alkyl having from 1 to 6 carbon atoms; --CH═CR 16 R 17 wherein R 16 is H, halogen, alkyl having from 1 to 6 carbon atoms, CN, ##STR18## wherein n is 0 or 1 and R c is H, alkyl having from 1 to 6 carbon atoms, phenyl or benzyl, CHOHR c or C(OR d ) 2 R c wherein R c is defined above and R d is alkyl having from 1 to 6 carbon atoms, R 17 is H, alkyl having from 1 to 6 carbon atoms, alkoxy having from 1 to 6 carbon atoms, benzyl, phenyl or halogen; --C.tbd.C--R 18 wherein R 18 is H, alkyl having from 1 to 12 carbon atoms, alkoxy having from 1 to 6 carbon atoms, ##STR19## wherein Y and R c are defined above; --CHOH--C.tbd.C--R 19 wherein R 19 is H, alkyl of from 1 to 6 carbon atoms, phenyl or benzyl; --CH═C═CHR 19 wherein R 19 is defined above; ═CH═N--OR 19 wherein R 19 is defined above; ##STR20## wherein Z is O or S, and R 16 and R 19 are defined above; --CH(ZR 20 ) 2 wherein Z is defined above and R 20 is alkyl having from 1 to 6 carbon atoms, phenyl, benzyl or the two groups R 20 may together form --(CH 2 )p-- wherein p is 2 or 3; ##STR21## wherein A and B are H, halogen, alkyl having from 1 to 6 carbon atoms, phenyl, benzyl or ##STR22## wherein n and R c are defined above; --CH═N--NDE wherein D and E are H, alkyl having from 1 to 6 carbon atoms, benzyl, phenyl, COG, SO 2 G or CO 2 G wherein G is alkyl having from 1 to 6 carbon atoms, benzyl or phenyl; R 4 is H or OH; R 5 is OH; or when R 4 and R 5 are taken together they may form ##STR23## wherein Z is defined above; a is a 5,6 bond; b is an optional bond, when present Q and R 3 are missing; X is O or H/OR" wherein R" is H, alkanoyl having from 1 to 6carbon atoms or trifluoroacetyl; and Q is hydrogen, chlorine or bromine.
Claim 2
Dependent Claim 526 words
A compound having structural formula I: ##STR16## wherein R 1 is hydrogen and R 2 is ═O, H, or OR 11 wherein R 11 is H, alkanoyl having from 1 to 6 carbon atoms or ##STR17## --CO--(CH 2 ) m wherein m is 0, 1, 2 or 3 and Y is hydrogen, halogen, alkyl having from 1 to 6 carbon atoms, alkoxy having from 1 to 6 carbon atoms, alkylthio having from 1 to 6 carbon atoms, OH, CF 3 , NO 2 , CN, phenyl, benzyl, phenoxy or NR a R b wherein R a and R b are the same or different and are H or alkyl having from 1 to 6 carbon atoms; or R 2 may be SO 3 OR' or OR' wherein R' is alkyl having from 1 to 6 carbon atoms; R 3 is hydrogen; alkyl having from 1 to 10 carbon atoms; CH 2 OH; CHO; CO 2 R 15 wherein R 15 is H or alkyl having from 1 to 6 carbon atoms; --CH═CR 16 R 17 wherein R 16 is H, halogen, alkyl having from 1 to 6 carbon atoms, CN, ##STR18## wherein n is 0 or 1 and R c is H, alkyl having from 1 to 6 carbon atoms, phenyl or benzyl, CHOHR c or C(OR d ) 2 R c wherein R c is defined above and R d is alkyl having from 1 to 6 carbon atoms, R 17 is H, alkyl having from 1 to 6 carbon atoms, alkoxy having from 1 to 6 carbon atoms, benzyl, phenyl or halogen; --C.tbd.C--R 18 wherein R 18 is H, alkyl having from 1 to 12 carbon atoms, alkoxy having from 1 to 6 carbon atoms, ##STR19## wherein Y and R c are defined above; --CHOH--C.tbd.C--R 19 wherein R 19 is H, alkyl of from 1 to 6 carbon atoms, phenyl or benzyl; --CH═C═CHR 19 wherein R 19 is defined above; ═CH═N--OR 19 wherein R 19 is defined above; ##STR20## wherein Z is O or S, and R 16 and R 19 are defined above; --CH(ZR 20 ) 2 wherein Z is defined above and R 20 is alkyl having from 1 to 6 carbon atoms, phenyl, benzyl or the two groups R 20 may together form --(CH 2 )p-- wherein p is 2 or 3; ##STR21## wherein A and B are H, halogen, alkyl having from 1 to 6 carbon atoms, phenyl, benzyl or ##STR22## wherein n and R c are defined above; --CH═N--NDE wherein D and E are H, alkyl having from 1 to 6 carbon atoms, benzyl, phenyl, COG, SO 2 G or CO 2 G wherein G is alkyl having from 1 to 6 carbon atoms, benzyl or phenyl; R 4 is H or OH; R 5 is OH; or when R 4 and R 5 are taken together they may form ##STR23## wherein Z is defined above; a is a 5,6 bond; b is an optional bond, when present Q and R 3 are missing; X is O or H/OR" wherein R" is H, alkanoyl having from 1 to 6carbon atoms or trifluoroacetyl; and Q is hydrogen, chlorine or bromine.
Claim 3
Dependent Claim 64 words
A compound having structural formula I as defined in claim 1 wherein: a is a 5,6 double bond; X is 0 or α-H/β-OH; Q is H or Cl; R 1 is H; R 2 is OR 11 ; R 3 is H, CH 3 , C 2 H 5 or CH═CH 2 ; R 4 is H or OH; and R 5 is OH.
Claim 4
Dependent Claim 16 words
A compound defined in claim 1 wherein R 1 is hydrogen and R 5 is hydroxy.
Claim 5
Dependent Claim 27 words
A compound having the name: 8,13-Epoxy-1α,7β,9α-trihydroxylabd-5(6)-en-11-one 7-acetate; 8,13-Epoxy-1α,7β,9α-trihydroxylabda-5(6),14-diene-11-one 7-acetate 1,9-carbonate; 8,13-Epoxy-1α,7β,9α-trihydroxy-labda-5(6),14-diene-11-one; 8,13-Epoxy-1α,7β,9α-trihydroxy-labd-5(6),14-diene-11-one 7-acetate; 8,13-Epoxy-1α,7β,9α-trihydroxy labda-5(6),14-diene-11-one 7-propionate; 8,13-Epoxy-1α,7β,9α-trihydroxy-labda-5(6),14-diene-11-one 7-methylether; 8,13-Epoxy-1α,7β,9α,11β-tetrahydroxy labda-5(6),14-diene; 8,13-Epoxy-1α,7β-dihydroxy-labda-5(6),14-diene-11-one 7-acetate; 12-Chloro-8,13-epoxy-1α,7β-dihydroxy-labda-5(6),14-diene-11-one 7-acetate; 8,13-Epoxy-1α,7β,9α-trihydroxy-labda-5(6),14-diene-11-one 7-butyrate; 8,13-Epoxy-1α,9α-dihydroxy-labda-5(6),14-diene-7,11-dione.
Claim 6
Dependent Claim 27 words
A compound having the name: 8,13-Epoxy-1α,7β,9α-trihydroxylabd-5(6)-en-11-one 7-acetate; 8,13-Epoxy-1α,7β,9α-trihydroxylabda-5(6),14-diene-11-one 7-acetate 1,9-carbonate; 8,13-Epoxy-1α,7β,9α-trihydroxy-labda-5(6),14-diene-11-one; 8,13-Epoxy-1α,7β,9α-trihydroxy-labd-5(6),14-diene-11-one 7-acetate; 8,13-Epoxy-1α,7β,9α-trihydroxy labda-5(6),14-diene-11-one 7-propionate; 8,13-Epoxy-1α,7β,9α-trihydroxy-labda-5(6),14-diene-11-one 7-methylether; 8,13-Epoxy-1α,7β,9α,11β-tetrahydroxy labda-5(6),14-diene; 8,13-Epoxy-1α,7β-dihydroxy-labda-5(6),14-diene-11-one 7-acetate; 12-Chloro-8,13-epoxy-1α,7β-dihydroxy-labda-5(6),14-diene-11-one 7-acetate; 8,13-Epoxy-1α,7β,9α-trihydroxy-labda-5(6),14-diene-11-one 7-butyrate; 8,13-Epoxy-1α,9α-dihydroxy-labda-5(6),14-diene-7,11-dione.
Claim 7
Dependent Claim 15 words
A compound defined in claim 1 having the name: 8,13-epoxy-1α,7β,9α-trihydroxy-labd-5(6)-ene-11-one 7-acetate; 8,13-epoxy-1α,7β,9α-trihydroxy-labd-5(6),14-dien-11-one 7-acetate; 8,13-epoxy-1α,7β,9α-trihydroxy-labda-5(6),14-diene 7-propionate.
Claim 8
Dependent Claim 31 words
A pharmaceutical composition useful for treating allergic reactions in a mammal which comprises an antiallergic effective amount of a compound defined in claim 1, in combination with a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim 31 words
A pharmaceutical composition useful for treating allergic reactions in a mammal which comprises an antiallergic effective amount of a compound defined in claim 2, in combination with a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim 31 words
A pharmaceutical composition useful for treating allergic reactions in a mammal which comprises an antiallergic effective amount of a compound defined in claim 3, in combination with a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim 31 words
A pharmaceutical composition useful for treating allergic reactions in a mammal which comprises an antiallergic effective amount of a compound defined in claim 4, in combination with a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim 31 words
A pharmaceutical composition useful for treating allergic reactions in a mammal which comprises an antiallergic effective amount of a compound defined in claim 5, in combination with a pharmaceutically acceptable carrier.

References Cited (Backward Citations)

US4118508A Cited
US4134986A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-05-13 1988-11-12 1989-05-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-05-13 1992-11-12 1993-05-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-05-13 1996-11-12 1997-05-14 $7700.00 Window Closed / Lapsed

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