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US4173571A
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13-Halo and 13-deoxy derivatives of C-076 compounds
Assignee: Merck and Co Inc
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Filing: 1977-12-19
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Granted: 1979-11-06
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Expires: 1997-12-19
Abstract
Abstract Derivatives of the C-076 compounds are disclosed wherein the 13-position is unsubstituted. The compounds are prepared by removing the glycosyl groups on the 13-position of the C-076 compounds isolated from the fermentation broth of Streptomyces avermitilis, followed by halogenation and subsequent removal of the halogen. The disclosed compounds are antiparasitic, anthelmintic, insecticidal and acaricidal agents.
Inventors
- 👤 John C. Chabala
- 👤 Michael H. Fisher
- 👤 Helmut H. Mrozik
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 22:30
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/22; A; A01; A01N; A01N43/00; A01N43/02; A01N43/04; A01N43/22; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07H; C07H17/00; C07H17/04; C07H17/08; C12; C12N; C12N1/00; C12N1/20; C12N1/205; C12P; C12P19/00; C12P19/44; C12P19/60; C12P19/62; C12P19/623; C12R; C12R2001/00; C12R2001/01; C12R2001/465
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
85 words
A compound having the formula: ##STR4## wherein the broken line indicates a single or a double bond; R 1 is hydrogen or halogen; R 2 is hydrogen, methyl or loweralkanoyl; R 3 is n-propyl or sec-butyl; and R 4 is present only when the broken line indicates a single bond and represents hydrogen, hydroxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxy; provided that when R 2 is hydrogen or methyl the broken line can indicate only a single bond and R 4 is other than hydroxy.
Claim 2
Dependent Claim
85 words
A compound having the formula: ##STR4## wherein the broken line indicates a single or a double bond; R 1 is hydrogen or halogen; R 2 is hydrogen, methyl or loweralkanoyl; R 3 is n-propyl or sec-butyl; and R 4 is present only when the broken line indicates a single bond and represents hydrogen, hydroxy, loweralkanoyloxy, loweralkylthio, loweralkylsulfinyl, loweralkylsulfonyl or loweralkoxy; provided that when R 2 is hydrogen or methyl the broken line can indicate only a single bond and R 4 is other than hydroxy.
Claim 3
Dependent Claim
10 words
The compound of claim 1 wherein R 3 is n-propyl.
Claim 4
Dependent Claim
10 words
The compound of claim 1 wherein R 3 is sec-butyl.
Claim 5
Dependent Claim
18 words
The compound of claim 3 wherein the broken line indicates a single bond and R 4 is hydrogen.
Claim 6
Dependent Claim
34 words
The compound of claim 4 wherein R 1 is chlorine, R 2 is hydrogen, R 3 is sec-butyl, R 4 is hydrogen, and the broken line indicates a single bond, which is 13-chloro-13-deoxy-22,23, dihydro-C-076-B1a-aglycone.
Claim 7
Dependent Claim
33 words
The compound of claim 4 wherein R 1 is hydrogen, R 2 is hydrogen, R 3 is sec-butyl, R 4 is hydrogen, and the broken line indicates a single bond, which is 13-deoxy-22,23-dihydro-C-076-B1a-aglycone.
Claim 8
Dependent Claim
33 words
The compound of claim 4 wherein R 1 is hydrogen, R 2 is methyl, R 3 is sec-butyl, R 4 is hydrogen and the broken line indicates a single bond, which is 13-deoxy-22,23-dihydro-C-076-A1a-aglycone.
Claim 9
Dependent Claim
11 words
The compound of claim 3 wherein R 2 is a loweralkanoyl.
Claim 10
Dependent Claim
34 words
The compound of claim 8 wherein R 1 is chlorine, R 2 is acetyl, R 3 is sec-butyl, and R 4 and the broken line represent a 22,23-double bond, which is 13-chloro-13-deoxy-C-076 B1a aglycone-5-O-acetate.
Claim 11
Dependent Claim
32 words
The compound of claim 8 wherein R 1 is hydrogen, R 2 is acetyl, R 3 is sec-butyl and R 4 and the broken line indicate a 22,23-double bond, which is 13-deoxy-C-076-B1a-aglycone-5-O-acetate.
Claim 12
Dependent Claim
10 words
The compound of claim 3 wherein R 4 is loweralkanoyloxy.
Claim 13
Dependent Claim
12 words
The compound of claim 11 wherein R 4 is an acetoxy group.
Claim 14
Dependent Claim
34 words
The compound of claim 12 wherein R 1 is chlorine, R 2 is hydrogen, R 3 is sec-butyl, R 4 is acetoxy, and the broken line indicates a single bond, which is 13-chloro-13-deoxy-C-076-B2a-aglycone 23-O-acetate.
Claim 15
Dependent Claim
34 words
The compound of claim 12 wherein R 1 is hydrogen, R 2 is hydrogen, R 3 is sec-butyl, R 4 is acetoxy, and the broken line indicates a single bond, which is 13-deoxy-C-076-B2a-aglycone 23-O-acetate.
Claim 16
Dependent Claim
15 words
The compound of claim 3 wherein R 2 is loweralkanoyl, and R 4 is loweralkanoyloxy.
Claim 17
Dependent Claim
15 words
The compound of claim 15 wherein R 2 is acetate and R 4 is acetoxy.
Claim 18
Dependent Claim
34 words
The compound of claim 16 wherein R 1 is chlorine. R 2 is acetyl R 3 is sec-butyl, R 4 is acetoxy, and the broken line indicates a single bond, which is 13-chloro-13-deoxy-C-076-B2a-aglycone 5,23-di-O-acetate.
Claim 19
Dependent Claim
34 words
The compound of claim 16 wherein R 1 is hydrogen, R 2 is acetyl, R 3 is sec-butyl, R 4 is acetoxy, and the broken line indicates a single bond, which is 13-deoxy-C-076-B2a-aglycone 5,23-di-O-acetate.
References Cited (Backward Citations)
US3950360A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-11-05 | 1983-05-07 | 1983-11-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-05 | 1987-05-07 | 1987-11-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-05 | 1991-05-07 | 1991-11-06 | $7700.00 | Window Closed / Lapsed |