US3697513A
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Heterocyclic compounds containing ethylene double bonds and processes for their manufacture
Assignee: Novartis AG
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Filing: 1968-04-16
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Granted: 1972-10-10
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Expires: 1988-04-16
Abstract
Abstract The invention refers to a class of new compounds as well as a new process for making these compounds. The new compounds correspond to the general formula WHEREIN A1 represents a heterocyclic ring system which (a) contains at least one five-membered to six-membered heterocyclic ring having at least one ring oxygen atom and/or one ring sulphur atom, (b) is free of ring nitrogen atoms and of hydrogen atoms which are replaceable by alkali metal, and (c) is bonded by a ring carbon atom to a ring carbon atom of B1, or has two adjacent ring carbon atoms in common with two adjacent ring carbon atoms of B1, and wherein furthermore (a) B1 denotes a benzene ring or a heterocyclic ring of aromatic character containing five to six ring members, with these rings being permitted to contain further condensed-on aromatic, heterocyclic or hydroaromatic fivemembered to six-membered rings, but preferably only one such ring, and (b) v denotes an integer from 1 to 2, and (c) wherein m denotes an integer from 1 to 4 in the case of a single bond between A1 and B1, and denotes the numbers 1 or 2 in the case of rings A1 and B1 being condensed with one another, and wherein E1 represents an aromatic carbocyclic or heterocyclic rings system containing five to six ring members, which may contain further condensed-on aromatic or hydroaromatic ring system of carbocyclic or heterocyclic nature, and may contain aromatic, araliphatic, cycloaliphatic, aliphatic or other non-chromophoric substituents, with the exception of methyl groups, which are capable of carbanion formation in the presence of alkali metal ions.
Inventors
- 👤 Adolf Emil Siegrist
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 16:11
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/36; C07D307/40; C07D307/42; C07D307/77; C07D307/78; C07D307/79; C07D307/92; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/08; C07D333/24; C07D333/50; C07D333/52; C07D333/54; C07D333/56; C07D333/58; C07D333/62; C07D333/66; C07D333/74; C07D339/00; C07D339/08; C07D495/00; C07D495/02; C07D495/04; C08; C08K; C08K5/00; C08K5/0008; C08K5/005
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
33 words
Process according to claim 1 for the manufacture of heterocyclic compounds containing at least one ethylene double bond conjugated with a carbocyclic aromatic six-membered ring, characterized in that a compound of the formula
Claim 2
Dependent Claim
43 words
Process according to claim 2 characterized in that a compound of the formula as defined in claim 2 is reacted in anhydrous dimethylformamide as the reaction medium in the presence of a strong alkaline potassium compound, with an aldehyde-anil as the Schiff base.
Claim 3
Dependent Claim
13 words
Process according to claim 2 characterized in that a compound of the formula
Claim 4
Dependent Claim
12 words
Process according to Claim 1 characterized in that a compound of formula
Claim 5
Dependent Claim
23 words
Process according to claim 2 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula
Claim 6
Dependent Claim
40 words
Process according to claim 2 characterized in that the reaction is carried out in the presence of an alkali compound having a base strength at least equal to that of lithium hydroxide, preferably potassium tertiary-butylate or potassium hydroxide, in dimethylformamide.
Claim 7
Dependent Claim
108 words
Process according to claim 2 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula wherein X represents a bridge member -O- or -S-, Z1 represents a hydrogen atom, a methyl group R1, wherein however at least one of the symbols Z1 denotes a methyl group which is in the meta-position to one of the symbols X and R1 denotes hydrogen or a non-chromophoric substituent which is free of hydrogen atoms which are replaceable by alkali metal, or two symbols R1 in the ortho-position can together form a carbocyclic condensed-on six-membered ring, and r denotes the numbers 1 or 2.
Claim 8
Dependent Claim
101 words
Process according to claim 2 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula wherein X represents a bridge member -O- or -S- and Z1 represents a hydrogen atom, a methyl group or a residue R1, but at least one of the two symbols Z1 represents a methyl group, R1 denotes hydrogen or a non-chromophoric substituent which is free of hydrogen atoms which are replaceable by alkali metal, or two symbols R1 in the ortho-position can together form a carbocyclic condensed-on six-membered ring, and s denotes an integer from 1 to 3.
Claim 9
Dependent Claim
128 words
Process according to claim 1 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula and wherein X denotes a bridge member -0- or -S-, R1 denotes hydrogen or a non-chromophoric substituent which is free of hydrogen atoms which are replaceable by alkali metal or two symbols R1 in the ortho-position can together from a carbo-cyclic condensed-on six-membered ring, Z1 represents a hydrogen atom, a methyl group or a residue R1 but at least one of the symbols Z1 represents a methyl group, and methyl groups in the condensed ring system are to be in the meta-position to a bridge member -O-or -S- and r represents the number 1 or 2 and t represents an integer from 1 to 4.
Claim 10
Dependent Claim
109 words
Process according to claim 2 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula and wherein Z1 represents a hydrogen atom, a methyl group or a residue R1, but at least one of the two symbols Z1 represents a methyl group, R1 denotes a hydrogen or non-chromophoric substituent which is free of hydrogen Atoms which are replaceable by alkali metal or two symbols R1 in the ortho-position can together form a carbocyclic condensed-on six-membered ring, X represents a bridge member -O- or -S-, s denotes an integer from 1 to 3 and t denotes an integer from 1 to 4.
Claim 11
Dependent Claim
103 words
Process according to claim 1 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula wherein X represents a bridge member -O- or -S-, Z1 represents a hydrogen atom, a methyl group or a residue R1 but at least one of the two symbols Z1 represents a methyl group, R1 denotes hydrogen, halogen, an alkyl or alkoxy group containing one to four carbon atoms, a benzyl group or phenyl group, or two symbols R1 in the ortho-position can together form an aromatic carbocyclic condensed-on six-membered ring, and n denotes an integer from 1 to 2.
Claim 12
Dependent Claim
91 words
Process according to claim 2 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula and wherein X represents a bridge member -O- or -S- and Z1 represents a hydrogen atom, a methyl group or a residue R1, but at least one of the two symbols Z1 represents a methyl group, R1 denotes hydrogen, alkyl, alkoxy, phenyl or halogen, or two symbols R1 in the ortho-position can together form a carbocyclic condensed-on six-membered ring, and t represents an integer from 1 to 4.
Claim 13
Dependent Claim
96 words
Process according to claim 2 characterized in that anils of aldehydes of aromatic character are reacted with compounds which correspond to the formula and wherein X represents a bridge member -O- or -S-, Z1 represents hydrogen, a methyl group or a residue R1, wherein however at least one of the two symbols Z1 represents a methyl group, R1 denotes hydrogen, alkyl, alkoxy, phenyl or halogen, or two symbols R1 in the ortho-position can together form a carbocyclic condensed-on six-membered ring, t represents an integer from 1 to 4 and r denotes the number 1 or 2.
Claim 14
Dependent Claim
130 words
Process according to claim 2 characterized in that as the compound according to the formula in Patent claim 1, a compound is reacted which corresponds to the formula wherein Z2 denotes a hydrogen atom or a methyl group, but at least one of the two symbols Z2 represents a methyl group, R2 denotes a hydrogen atom, a phenyl group, an alkyl group containing 2 to 12 carbon atoms, an alkoxy group containing one to four carbon atoms or a halogen atom, wherein r represents the number, 1 or 2 and s represents the numbers 1, 2 or 3 and the sum of r+s, in the case of substituents different from hydrogen, does not amount to more than 4 and wherein furthermore a maximum of two phenyl substituents may be present.
Claim 15
Dependent Claim
90 words
Process according to claim 1 characterized in that as the compound according to the formula in Patent claim 1, a compound is reacted which corresponds to the formula wherein R4'' denotes a hydrogen atom, an alkyl group containing one to four carbon atoms, an alkoxy group containing one to four carbon atoms or halogen, or two adjacent residues R4'' together may form a condensed-pn benzene ring, R5 denotes hydrogen, methyl, phenyl or benzyl, and r represents the numbers 1 or 2 and X represents a bridge member -O- or -S-.
Claim 16
Dependent Claim
65 words
Process according to claim 1 characterized in that as the compound according to the formula in Patent claim 1, a compound is reacted which corresponds to the formula wherein R5 represents hydrogen or phenyl and the methyl group given in the formula is preferably in positions 5 or 6 of the benzothiophene or benzofurane ring respectively, and X represents a bridge member -O- or -S-.
Claim 17
Dependent Claim
96 words
Process according to claim 2 characterized in that as the compound according to the formula of claim 1, compounds are reacted which correspond to the formula wherein Z2 denotes a hydrogen atom or a methyl group, but at least one of the two symbols Z2 represents a methyl group, X represents a bridge member -O- or -S-, R2 denotes a hydrogen atom, a phenyl group, an alkyl group containing two to 12 carbon atoms, an alkoxy group containing one to four carbon atoms, or a halogen atom and s represents the numbers 1, 2 or 3.
Claim 18
Dependent Claim
48 words
Process according to claim 1 characterized in that as compounds according to the formula in claim 1, compounds are reacted which correspond to the formula wherein the symbols Z3 either both denote hydrogen or both represent a methyl group, and X represents a bridge member -O- or -S-.
Claim 19
Dependent Claim
78 words
Process according to claim 2 characterized in that as compounds according to the formula of claim 1, compounds are reacted which correspond to the formula and wherein Z2 denotes a hydrogen atom or a methyl group, but at least one of the two symbols Z2 represents a methyl group, R3 denotes a hydrogen atom, a halogen atom, an alkyl group containing two to four carbon atoms or a phenyl group and r represents the numbers 1 or 2.
Claim 20
Dependent Claim
57 words
Process according to Patent claim 2 characterized in that as compounds according to the formula of claim 1, compounds are reacted which correspond to the formula wherein U1 represents a hydrogen atom, a phenyl group, an alkyl group containing two to four carbon atoms, an alkoxy group containing one to four carbon atoms or a halogen atom.
Claim 21
Dependent Claim
56 words
Process according to claim 2 characterized in that as compounds according to the formula of claim 1, compounds are reacted which correspond to the formula wherein U1 represents a hydrogen atom, a phenyl group, an alkyl group containing two to four carbon atoms, an alkoxy group containing one to four carbon atoms or a halogen atom.
Claim 22
Dependent Claim
63 words
Process according to claim 1 characterized in that, as the compound according to the formula of Patent claim 1, a compound is reacted which corresponds to the formula wherein U2 represents hydrogen or phenyl and, of the symbols Z3 and Z3'', either both denote hydrogen or one of the two symbols Z3 and Z3'' represents the methyl group whilst the other denotes hydrogen.
Claim 23
Dependent Claim
68 words
Process according to claim 1 characterized in that a compound of formula is used as the Schiff base, wherein h represents hydrogen or chlorine and E5 represents phenyl, naphthyl, diphenylyl, thienyl or a phenyl residue which may be substituted by halogen, alkyl groups containing one to four carbon atoms, alkoxy groups containing one to four carbon atoms, alkylamino groups containing one to four carbon atoms or methylenedioxy groups.
Claim 24
Dependent Claim
53 words
Process according to claim 2 characterized in that an aldehyde-anil of formula is used as the Schiff base, wherein k and l denote a hydrogen atom, a chlorine atom or a methoxy group or adjacent k and 1 together denote the group -O-CH2-O- and h denotes a hydrogen atom or a chlorine atom.
Claim 25
Dependent Claim
37 words
Process according to claim 2 characterized in that an alkali metal compound of formula KOCm 1H2m 1 is used as the strongly basic alkali compound, wherein m denotes an integer having a value of at most 6.
Claim 26
Dependent Claim
8 words
A heterocyclic compound which corresponds to the formula
Claim 27
Dependent Claim
8 words
A heterocyclic compound which corresponds to the formula
Claim 28
Dependent Claim
90 words
A heterocyclic compound which corresponds to the formula wherein R4 denotes hydrogen, an alkyl group containing one to four carbon atoms, an alkoxy group containing one to four carbon atoms or halogen, R5 denotes hydrogen, methyl, phenyl or benzyl, r represents the numbers 1 or 2, E5 denotes phenyl, naphthyl, diphenylyl, thienyl or a phenyl residue which may be substituted by halogen, alkyl groups containing one to four carbon atoms, alkoxy groups containing one to four carbon atoms or methylenedioxy groups, and X represents a bridge member -O- or -S-.
Claim 29
Dependent Claim
50 words
A heterocyclic compound which corresponds to the formula wherein R5 represents hydrogen or phenyl and E6 denotes phenyl, naphthyl, diphenylyl or a phenyl residue which may be substituted by halogen, alkoxy groups containing one to four carbon atoms or methylenedioxy groups, and X represents a bridge member -O- or -S-.
Claim 30
Dependent Claim
8 words
A heterocyclic compound which corresponds to the formula
Claim 31
Dependent Claim
47 words
A heterocyclic compound which corresponds to the formula wherein E7 denotes phenyl, naphthyl or a phenyl group which is substituted by alkyl groups or alkoxy groups containing one to four carbon atoms, Ez represents hydrogen or -CH CH-E7 and X denotes a bridge member -O- or -S-.
Claim 32
Dependent Claim
8 words
A heterocyclic compound which corresponds to the formula
Claim 33
Dependent Claim
77 words
A heterocyclic compound which corresponds to the formula and wherein E4 denotes a phenyl, naphthyl or thienyl residue which may contain further substituents of the group of halogen, alkyl, alkoxy, alkylamino with one to 18 carbon atoms in each case, phenyl or a methylenedioxy ring, wherein furthermore U1 represents a hydrogen atom, a phenyl group, an alkyl group containing two to four carbon atoms, an alkoxy group containing one to four carbon atoms or a halogen atom.
Claim 34
Dependent Claim
77 words
A heterocyclic compound which corresponds to the formula and wherein E4 denotes a phenyl, naphthyl or thienyl residue which may contain further substituents of the group of halogen, alkyl, alkoxy, alkylamino with one to 18 carbon atoms in each case, phenyl or a methylenedioxy ring, and wherein U1 represents a hydrogen atom, a phenyl group, an alkyl group containing two to four carbon atoms, an alkoxy group containing one to four carbon atoms or a halogen atom.
Claim 35
Dependent Claim
59 words
A heterocyclic compound which corresponds to the formula wherein U2 represents hydrogen or phenyl, E6 denotes phenyl, diphenylyl, naphthyl or a phenyl group substituted by alkoxy groups containing one to four carbon atoms, and Ex and Ey either both denote hydrogen or one of the symbols Ex and Ey represents a group E6-CH CH- whilst the other denotes hydrogen.
Claim 36
Dependent Claim
46 words
A heterocyclic compound which corresponds to the formula wherein X denotes a bridge member -O- or -S-, R8 represents hydrogen, alkyl having one to four carbon atoms, halogen, alkoxy having one to four carbon atoms, benzyl or phenyl, and R9 represents hydrogen or a methyl group.
Claim 37
Dependent Claim
17 words
A heterocyclic compound which corresponds to the formula wherein X denotes a bridge member -O- or -S-.
Claim 38
Dependent Claim
11 words
A compound according to claim 38, wherein X stands for O.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1975-10-10 | 1976-04-10 | 1976-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-10-10 | 1980-04-10 | 1980-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-10-10 | 1984-04-10 | 1984-10-10 | $7700.00 | Window Closed / Lapsed |