Claims
- 1. A method for treating allergic reactions in a mammal which comprises administering a bronchodilating effective amount or an amount effective to inhibit histamine release of a compound having structural formula I ##STR17## in combination with a pharmaceutically acceptable carrier to said mammal, wherein one of R.sub.1 and R.sub.2 may be .dbd.O and the other of R.sub.1 and R.sub.2 may be H, or OR.sub.11 or both of R.sub.1 and R.sub.2 may be H or OR.sub.11 wherein R.sub.11 is H, alkanoyl having from 1 to 6 carbon atoms or ##STR18## {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.sub.3, NO.sub.2, CN, phenyl, benzyl, phenoxy or NR.sub.a R.sub.b wherein R.sub.a and R.sub.b are the same or different and are H or alkyl having from 1 to 6 carbon atoms}; or
- R.sub.1 and R.sub.2 may be taken together to form ##STR19## wherein R.sub.13 and R.sub.14 may be the same or different and are H, alkyl having from 1 to 6 carbon atoms, alkoxy having from 1 to 6 carbon atoms, alkenyl having from 2 to 6 carbon, alkynyl having from 2 to 6 carbon atoms, or ##STR20## wherein m and Y are as defined above, or R.sub.2 may be SO.sub.3 OR' or OR' wherein R' is alkyl having from 1 to 6 carbon atoms;
- R.sub.3 is hydrogen, alkyl having from 1 to 10 carbon atoms, CH.sub.2 OH, CHO, CO.sub.2 R.sub.15 {wherein R.sub.15 is H or alkyl having from 1 to 6 carbon atoms}, --CH.dbd.CR.sub.16 R.sub.17 {wherein R.sub.16 is H, halogen, alkyl having from 1 to 6 carbon atoms, ##STR21## (wherein n is 0 or 1 and R.sub.c is H, alkyl having from 1 to 6 carbon atoms, phenyl or benzyl), CHOHR.sub.c or C(OR.sub.d).sub.2 R.sub.c (wherein R.sub.c is defined above and R.sub.d is alkyl having from 1 to 6 carbon atoms), and R.sub.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.sub.18 {wherein R.sub.18 is H, alkyl having from 1 to 12 carbon atoms, alkoxy having from 1 to 6 carbon atoms, ##STR22## CO.sub.2 Rc or ##STR23## wherein Y and R.sub.c are defined above}, --CHOH--C.tbd.C--R.sub.19 {wherein R.sub.19 is H, alkyl of from 1 to 6 carbon atoms, phenyl or benzyl},
- --CH.dbd.C.dbd.CHR.sub.19 {wherein R.sub.19 is defined above},
- --CH.dbd.N--OR.sub.19 {wherein R.sub.19 is defined above}, ##STR24## {wherein Z is O or S, and R.sub.16 and R.sub.19 are defined above }, --CH(ZR.sub.20).sub.2 {wherein Z is defined above and R.sub.20 is alkyl having from 1 to 6 carbon atoms, phenyl, benzyl or the two groups R.sub.20 may together form --(CH.sub.2).sub.p -- wherein p is 2 or 3}, ##STR25## {wherein A and B are H, halogen, alkyl having from 1 to 6 carbon atoms, phenyl, benzyl or ##STR26## wherein n and R.sub.c are defined above}, --CH.dbd.N--NDE {wherein D and E are H, alkyl having from 1 to 6 carbon atoms, benzyl, phenyl, COG, SO.sub.2 G, CO.sub.2 G (wherein G is alkyl having from 1 to 6 carbon atoms, benzyl or phenyl)};
- R.sub.4 is H or OH;
- R.sub.5 is OH; or
- when R.sub.4 and R.sub.5 are taken together they may form ##STR27## wherein Z is defined above; a is an optional bond which may be located in either the 5,6 or 6,7 position, such that when a is a 5,6 bond, R.sub.2 is .dbd.O, H or OR.sub.11 with R.sub.11 equal to H, alkanoyl or ##STR28## wherein m and Y are as previously defined, such that when R.sub.2 is H or OR.sub.11, R.sub.1 is H or OR.sub.11 with R.sub.11 equal to alkanoyl or ##STR29## and when R.sub.2 is .dbd.O, R.sub.1 represents H or OR.sub.11 with R.sub.11 equal to H, alkanoyl or ##STR30## wherein m and Y are as previously defined, and when a is a 6,7 bond, R.sub.1 can be H or OR.sub.11 where R.sub.11 is alkanoyl, and R.sub.2 may be H or OR.sub.11 where R.sub.11 is alkanoyl;
- b is an optional bond, such that when b is present, Q and R.sub.3 are H;
- X is O or H/OR" {wherein R" is H, alkanoyl having from 1 to 6 carbon atoms or trifluoroacetyl}; and
- Q is hydrogen, chlorine or bromine.
- 2. The method defined in claim 1 wherein
- R.sub.1 and R.sub.2 may be the same or different and are hydrogen or OR.sub.11 wherein R.sub.11 is defined in claim 1 and Y is hydrogen;
- R.sub.3 is --CH.dbd.CHR.sub.30 wherein R.sub.30 is hydrogen, alkyl having from 1 to 6 carbon atoms, phenyl or benzyl;
- --C.tbd.CR.sub.30 ;
- --CHOH--C.tbd.C--R.sub.30 ;
- --CH.dbd.C.dbd.CHR.sub.30 ;
- --CH.dbd.N--OR.sub.30 ; ##STR31## --CH.dbd.N--NHR.sub.31 wherein R.sub.31 is hydrogen, alkyl having from 1 to 6 carbon atoms, phenyl, benzyl, SO.sub.2 R.sub.32 and CO.sub.2 R.sub.32 wherein R.sub.32 is alkyl having from 1 to 6 carbon atoms;
- R.sub.4 is H or OH;
- a is either not present or is located in the 5,6 position in which instance R.sub.1 is H and R.sub.2 is OR.sub.11 wherein R.sub.11 is defined hereinabove;
- Y is hydrogen;
- X is O or H/OH; and
- Q is hydrogen or chlorine.
- 3. The method defined in claim 1 wherein R.sub.1 and R.sub.2 may be the same or different and are hydrogen or OR.sub.11 wherein R.sub.11 is defined in claim 1 and Y is hydrogen;
- R.sub.3 is hydrogen, alkyl having from 1 to 6 carbon atoms, --CH.dbd.CHR.sub.301 or --C.tbd.CR.sub.301 [wherein R.sub.301 is hydrogen, alkyl having from 1 to 6 carbon atoms, phenyl, benzyl or CO.sub.2 R.sub.c wherein R.sub.c is defined in claim 1 ];
- R.sub.4 is H or OH;
- R5 is OH;
- a is either not present or is located in the 5,6 position in which instance R.sub.1 is H and R.sub.2 is OR.sub.11 wherein R.sub.11 is defined hereinabove;
- Y is hydrogen;
- X is O or H/OH; and
- Q is hydrogen or chlorine.
- 4. The method defined in claim 3 wherein R.sub.4 is H.
- 5. The method defined in claim 1 which utilizes 7.beta.-acetoxy-8,13-epoxy-1.alpha.,6.beta.,9.alpha.-trihydroxylabd-14-en-11-one.
- 6. The method defined in claim 1 which utilizes 8,13-epoxy-1.alpha.,6.beta.,7.beta.-trihydroxylabd-14-en-one 7-acetate.
- 7. The method defined in claim 1 which utilizes 8,13-epoxy-1.alpha.,6.beta.,7.beta.,9.alpha.-tetrahydroxylabd-14-en-11-one
- 8. The method defined in claim 1 which utilizes 6.beta.-acetoxy-8,13-epoxy-1.alpha.,7.beta.,9.alpha.-trihydroxylabd-14-en-11-one.
- 9. The method defined in claim 1 which utilizes 8,13-epoxy-1.alpha.,7.beta.,9.alpha.-trihydroxy-labda-5(6),14-dien-11-one 7-acetate.
CROSS REFERENCE TO RELATED APPLICATION
This application is a file-wrapper-continuation of U.S. application Ser. No. 698,955, filed Feb. 6, 1985, now abandoned, which is a division of U.S. application Ser. No. 542,825, filed Oct. 17, 1983, now U.S. Pat. No. 4,517,200, which in turn is a continuation-in-part of U.S. application Ser. No. 453,436, filed Dec. 27, 1982, now abandoned.
US Referenced Citations (2)
| Number |
Name |
Date |
Kind |
|
4118508 |
Bhat et al. |
Oct 1978 |
|
|
4134986 |
Bajwa et al. |
Jan 1979 |
|
Non-Patent Literature Citations (5)
| Entry |
| Fieser and Fieser, Reagents for Organic Synthesis, John Wiley & Sons, New York, vol. 1, 1967, pp. 524-526, 1174. |
| Takeda et al., Chem. Abstr., 92, 177403j (1980). |
| Tandon et al., Ibid., 89, 163779n (1978). |
| Bajwa et al., Ibid., 89, 129755s (1978). |
| Hoechst, Ibid., 89, 24150n (1978). |
Divisions (1)
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Number |
Date |
Country |
| Parent |
542825 |
Oct 1983 |
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Continuations (1)
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Number |
Date |
Country |
| Parent |
698955 |
Feb 1985 |
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Continuation in Parts (1)
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Number |
Date |
Country |
| Parent |
453436 |
Dec 1982 |
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Patent Grant
4782082
