US4587247A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones, compositions and use
Assignee: Merck and Co Inc
•
Filing: 1985-02-25
•
Granted: 1986-05-06
•
Expires: 2005-02-25
Abstract
Abstract Novel substituted and unsubstituted 13-(alkoxy)methoxy derivatives of the avermectin aglycones are useful as anthelmintic and antiparasitic agents. The compounds are also useful as pesticides and insecticides against agricultural pests. Included herein are novel intermediates useful in the process for preparing said avermectin aglycone derivatives. Compositions of said derivatives and methods of administering said compositions are also disclosed.
Inventors
- 👤 Bruce O. Linn
- 👤 Helmut H. Mrozik
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 15:58
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/22; A; A01; A01N; A01N43/00; A01N43/90; A61; A61P; A61P33/00; A61P33/10
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
178 words
A compound having the formula: ##STR13## wherein the broken line indicates a single or a double bond; wherein R 1 is H, --OH, provided that the broken line indicates a single bond when R 1 is OH; R 2 is methyl, ethyl, iso-propyl or sec-butyl; R 3 is OH, OCH 3 , OSi(CH 3 ) 2 C(CH 3 ) 3 ; R 4 is X--(CH 2 ) n --O--CH 2 O-- wherein n is an integer ranging from 1-6 and X is hydrogen; alkyl C 1-6 ; alkoxy C 1-6 ; polyalkoxy, H--[(CH 2 ) p O] m -- wherein m is an integer from 2-6 and p is an integer ranging from 1-6; phenyl, phenyl (alkoxy C 1-4 ), acyloxy C 1-4 ; hydroxy; phenyl poly(alkoxy), --[(CH 2 ) p O] m -- wherein m and p are as defined above; halogen; amino; alkylamino C 1-5 ; dialkylamino C 2-8 ; or heterocyclic 3-6 membered nitrogen containing ring optionally containing an additional oxygen, sulfur or nitrogen heteroatom wherein the ring nitrogen is bonded to the alkoxy group.
Claim 2
Dependent Claim
178 words
A compound having the formula: ##STR13## wherein the broken line indicates a single or a double bond; wherein R 1 is H, --OH, provided that the broken line indicates a single bond when R 1 is OH; R 2 is methyl, ethyl, iso-propyl or sec-butyl; R 3 is OH, OCH 3 , OSi(CH 3 ) 2 C(CH 3 ) 3 ; R 4 is X--(CH 2 ) n --O--CH 2 O-- wherein n is an integer ranging from 1-6 and X is hydrogen; alkyl C 1-6 ; alkoxy C 1-6 ; polyalkoxy, H--[(CH 2 ) p O] m -- wherein m is an integer from 2-6 and p is an integer ranging from 1-6; phenyl, phenyl (alkoxy C 1-4 ), acyloxy C 1-4 ; hydroxy; phenyl poly(alkoxy), --[(CH 2 ) p O] m -- wherein m and p are as defined above; halogen; amino; alkylamino C 1-5 ; dialkylamino C 2-8 ; or heterocyclic 3-6 membered nitrogen containing ring optionally containing an additional oxygen, sulfur or nitrogen heteroatom wherein the ring nitrogen is bonded to the alkoxy group.
Claim 3
Dependent Claim
61 words
The compound of claim 1 wherein n is 1-3; X is selected from the group consisting of hydrogen, alkoxy C 1-4 , polyalkoxy H--[(CH 2 ) p O] m -- wherein p and m are 1-3, phenyl, phenylalkoxy C 1-4 , acyloxy C 1-4 , halogen, amino, alkylamino C 1-3 , dialkylamino C 2-6 , aziridino, pyrrolidino, morpholino, thiomorpholino and 4-methylpiperazino.
Claim 4
Dependent Claim
13 words
The compound of claim 2 where n is 2 and X is methoxy.
Claim 5
Dependent Claim
31 words
The compound of claim 3 which is 13-O-(2-methoxyethoxy)methyl-22,23-dihydro avermectin B1a/B1b aglycone; 13-O-(2-methoxyethoxy)methyl avermectin B1a/B1b aglycone; 13 -O-(2-methoxyethoxy)methyl avermectin B2a/B2b aglycone; 13-(2-methoxyethoxy)methyl milbemycin α 1 ; or 13-(2-methoxyethoxy)methoxy milbemycin α 3 .
Claim 6
Dependent Claim
30 words
The compound of claim 2 which is 13-O-[2-(2-methoxyethoxy)ethoxy]methyl-22,23-dihydro avermectin B1a/B1b aglycone; 13-O-[2-(2-methoxyethoxy)methoxyethoxy]methyl-22,23-dihydro avermectin B1a/B1b aglycone; 13-O-[2-(methoxymethoxy)ethoxy]methyl-22,23-dihydro avermectin B1a/B1b aglycone; 13-[2-(methoxymethoxy)ethoxy]methoxy milbemycin α 1 ; or 13-[2-(methoxymethoxy)ethoxy]methoxy milbemycin α 3 .
Claim 7
Dependent Claim
11 words
The compound of claim 2 which is 13-O-benzyloxymethyl-22,23-dihydro avermectin B1a/B1b aglycone.
Claim 8
Dependent Claim
11 words
The compound of claim 2 which is 13-O-methoxymethyl-22,23-dihydro avermectin B1a/B1b aglycone.
Claim 9
Dependent Claim
11 words
The compound of claim 2 which is 13-O-(2-chloroethoxy)methyl-22,23-dihydro avermectin B1a/B1b aglycone.
Claim 10
Dependent Claim
11 words
The compound of claim 2 which is 13-O-[2-(dimethylaminoethoxy)methyl-22,23-dihydro avermectin B1a/B1b aglycone.
Claim 11
Dependent Claim
11 words
The compound of claim 2 which is 13O-[2-(morpholin-1-yl)ethoxy]methyl-22,23-dihydro avermectin B1a/B1b aglycone.
Claim 12
Dependent Claim
28 words
A pharmaceutical composition for treatment of animals infected with parasites which comprises a therapeutically effective dosage amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
23 words
A method treating an animal suffering from a parasitic condition which comprises administering a therapeutically effective amount of a compound of claim 1.
References Cited (Backward Citations)
US3950360A
Cited
US4310519A
Cited
US4134973A
Cited
US4199569A
Cited
US4201861A
Cited
US4206205A
Cited
US4171314A
Cited
US4173571A
Cited
US4200581A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-05-05 | 1989-11-04 | 1990-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-05-05 | 1993-11-04 | 1994-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-05-05 | 1997-11-04 | 1998-05-06 | $7700.00 | Window Closed / Lapsed |