Patent US710245A successfully refreshed from Google Patents.
Patent US4154743A successfully refreshed from Google Patents.
US4154743A
Expired / Lapsed
US
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3-Oxobenzofuranyl-2-idenyl, haloacetic acids
Assignee: Novartis Corp
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Filing: 1978-02-09
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Granted: 1979-05-15
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Expires: 1998-02-09
Abstract
Abstract Novel halogeno-benzofuranone-carboxylic acids and a novel process for their preparation by reacting substituted or unsubstituted phenols with dihalogenomaleic anhydrides or derivatives thereof are described. The novel halogeno-benzofuranone-carboxylic acids are valuable intermediates for the preparation of pharmaceutical active compounds having an antiallergic action or for the preparation of biocidal active compounds for combating plant and animal pests, in particular phytopathogenic fungi and bacteria.
Inventors
- 👤 Hans Bosshard
- 👤 Niklaus Buhler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 15:30
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/78; C07D307/82; C07D307/83; C07D307/93
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
277 words
A compound of the formula I ##STR52## in which X is chlorine, bromine or fluorine, two of R 1 to R 4 independently of one another are hydrogen or lower alkyl, one of R 1 to R 4 is hydrogen, a halogen atom, hydroxyl or lower alkyl, and the last of R 1 to R 4 is hydrogen, a halogen atom, hydroxyl, carboxyl, lower alkyl, lower alkoxy, phenoxy, cycloalkyl of 5 to 8 carbon atoms, benzoyl; benzoyl substituted with alkyl of 1 to 4 carbon atoms, with alkoxy of 1 to 4 carbon atoms or with halogen; alkanoyl of 2 to 7 carbon atoms, amino, --NQ 1 Q 2 or --NHCOQ 3 ; wherein Q 1 is hydrogen or lower alkyl, Q 2 is lower alkyl; or Q 1 and Q 2 together are alkylene of 4 to 7 carbon atoms, thiaalkylene of 4 to 7 carbon atoms, oxaalkylene of 4 to 7 carbon atoms or iminoalkylene of 4 to 7 carbon atoms where the imino group --NQ 4 -- has Q 4 as hydrogen or lower alkyl, and Q 3 is lower alkyl; or if two of R 1 to R 4 are hydrogen, the remaining two of R 1 to R 4 together are alkylene of 3 to 5 carbon atoms, which may be substituted by alkyl of 1 to 4 carbon atoms, which together with the bonding C atoms in the ortho-position form a cycloalkyl group having 5 to 7 ring members which may be substituted by alkyl of 1 to 4 carbon atoms; or together are 1,4-butadienyl which together with the bonding C atoms in the ortho position form a fused benzene ring.
Claim 2
Dependent Claim
277 words
A compound of the formula I ##STR52## in which X is chlorine, bromine or fluorine, two of R 1 to R 4 independently of one another are hydrogen or lower alkyl, one of R 1 to R 4 is hydrogen, a halogen atom, hydroxyl or lower alkyl, and the last of R 1 to R 4 is hydrogen, a halogen atom, hydroxyl, carboxyl, lower alkyl, lower alkoxy, phenoxy, cycloalkyl of 5 to 8 carbon atoms, benzoyl; benzoyl substituted with alkyl of 1 to 4 carbon atoms, with alkoxy of 1 to 4 carbon atoms or with halogen; alkanoyl of 2 to 7 carbon atoms, amino, --NQ 1 Q 2 or --NHCOQ 3 ; wherein Q 1 is hydrogen or lower alkyl, Q 2 is lower alkyl; or Q 1 and Q 2 together are alkylene of 4 to 7 carbon atoms, thiaalkylene of 4 to 7 carbon atoms, oxaalkylene of 4 to 7 carbon atoms or iminoalkylene of 4 to 7 carbon atoms where the imino group --NQ 4 -- has Q 4 as hydrogen or lower alkyl, and Q 3 is lower alkyl; or if two of R 1 to R 4 are hydrogen, the remaining two of R 1 to R 4 together are alkylene of 3 to 5 carbon atoms, which may be substituted by alkyl of 1 to 4 carbon atoms, which together with the bonding C atoms in the ortho-position form a cycloalkyl group having 5 to 7 ring members which may be substituted by alkyl of 1 to 4 carbon atoms; or together are 1,4-butadienyl which together with the bonding C atoms in the ortho position form a fused benzene ring.
Claim 3
Dependent Claim
97 words
A compound of the formula I according to claim 1, in which X is chlorine, R 1 and R 2 independently of one another are hydrogen or an alkyl group having 1-4 carbon atoms, R 3 is hydrogen, chlorine, fluorine, bromine or an alkyl group having 1-4 carbon atoms and R 4 is hydrogen, chlorine, fluorine, bromine, --OH, --COOH, cyclohexyl, an alkyl or alkoxy group having 1-4 carbon atoms, an alkanoyl group having 2-7 carbon atoms, an alkanoylamino group having 2-4 carbon atoms or a N,N-dialkylamino group having 1 or 2 carbon atoms in each alkyl part.
Claim 4
Dependent Claim
51 words
A compound of the formula I according to claim 1, in which X is chlorine, R 3 and R 4 are hydrogen and R 1 and R 2 together form an alkylene group having 3-5 carbon atoms which is bonded in the 5,6-position or a 1,4-butadienyl group bonded in the 4,5-position.
Claim 5
Dependent Claim
80 words
A compound according to claim 1 of the formula Ia ##STR53## in which R 1 and R 2 independently of one another are hydrogen or alkyl having 1-4 carbon atoms and R 3 is hydrogen, alkyl or alkoxy having 1-4 carbon atoms or --OH, or in which R 1 and R 2 together form 1,4-butadienyl and R 3 is hydrogen or R 1 is hydrogen and R 2 and R 3 together form alkylene having 3 or 4 carbon atoms.
Claim 6
Dependent Claim
53 words
A compound of the formula Ia according to claim 4, in which R 1 is hydrogen or methyl and one of the radicals R 2 and R 3 is methyl and the other is hydrogen or methyl, or in which R 1 is hydrogen and R 2 and R 3 together are trimethylene.
Claim 7
Dependent Claim
136 words
A process for the preparation of a compound of the formula I according to claim 1, wherein a compound of the formula II ##STR54## is reacted in the presence of a Lewis acid with a compound of the formula III ##STR55## to give a compound of the formula IV ##STR56## in which formulae R 1 , R 2 , R 3 and R 4 are as defined under formula I, the two X' in formula III and IV independently of one another are chlorine, fluorine or bromine and one of Y 1 and Y 2 is halogen and the other is --OH or --O--alkyl having 1-6 C atoms, or Y 1 and Y 2 together form the grouping --O--, and the compound of the formula IV is subsequently cyclised to a compound of the formula I.
Claim 8
Dependent Claim
18 words
A process according to claim 6, wherein dichloromaleic anhydride is used as the compound of the formula III.
Claim 9
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR57##
Claim 10
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR58##
Claim 11
Dependent Claim
10 words
A compound according to claim 1 of the formula ##STR59##
References Cited (Backward Citations)
US3629290A
Cited
US3816467A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-05-14 | 1982-11-13 | 1983-05-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-05-14 | 1986-11-13 | 1987-05-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-05-14 | 1990-11-13 | 1991-05-15 | $7700.00 | Window Closed / Lapsed |