US3888877A
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Macrocyclic compounds and complexes thereof
Assignee: Merck Sharp & Dohme LLC
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Filing: 1973-03-26
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Granted: 1975-06-10
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Expires: 1993-03-26
Abstract
Abstract Novel macrocyclic (monocyclic and bicyclic) compounds having nitrogen bridgehead atoms and having in the hydrocarbon bridging chains at least two additional hetero atoms selected from the group consisting of sulfur, oxygen, and nitrogen, when admixed with a compatible cation-donor compound form stable cationcontaining macrocyclic complexes which, in turn, can be conveniently dissociated by addition of acid or a quaternizing agent. The novel macrocyclics are valuable for use in the same way and for the same purposes as chelating agents. The macrocyclic compounds are prepared by condensation reactions carried out via high dilution techniques, e.g. by condensing a substituted hydrocarbon di-carbonyl halide with a substituted hydrocarbon having terminal primary or secondary amino groups followed by reduction of the resulting lactam or, alternatively, by condensing a substituted hydrocarbon having terminal secondary or tertiary amino groups which have at least one hydrogenolyzable group with a substituted hydrocarbon di-halide (or di-sulfonate) followed by hydrogenolyzation of the macrocyclic compound thereby formed.
Inventors
- 👤 Jean-Marie Lehn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 20:28
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; C07C; C07C323/00; C07C323/23; C07C323/24; C07C323/25; C07C51/00; C07C51/16; C07C51/27; C07C59/00; C07C59/125; C07C59/235; C07C59/305; C07C59/40; C07C59/58; C07C59/64; C07C59/66; C07C59/68; C07D273/00; C07D291/00; C07D513/00; C07D513/02; C07D513/08; C07D515/00; C07D515/02; C07D515/08; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/50; C07F9/5004; C07F9/54; C07F9/5449; C07F9/547; C07F9/6564; C07F9/6571; C07F9/657163
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
15 words
A MACROCYCLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF A COMPOUND OF FOLLOWING FORMULA 1:
Claim 2
Dependent Claim
15 words
A MACROCYCLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF A COMPOUND OF FOLLOWING FORMULA 1:
Claim 3
Dependent Claim
18 words
A macrocyclic compound according to claim 1 wherein m, n and p are integers from 0 to 3.
Claim 4
Dependent Claim
33 words
A macrocyclic compound according to claim 1 wherein each D is a member selected from the group consisting of oxygen and sulfur; and m, n and p are integers from 0 to 3.
Claim 5
Dependent Claim
34 words
A macrocyclic compound according to claim 1 wherein each D is a member selected from the group consisting of oxygen and N- R; and m, n and p are integers from 0 to 3.
Claim 6
Dependent Claim
23 words
A macrocyclic compound according to claim 1 wherein each D is oxygen; and m, n and p are integers from 0 to 3.
Claim 7
Dependent Claim
27 words
A macrocyclic compound according to claim 1 wherein each D is oxygen; each A is ethylene; and m, n and p are integers from 0 to 2.
Claim 8
Dependent Claim
34 words
A compound according to claim 6 wherein each D is oxygen; each A is ethylene; and m, n and p are each the integer 1; said compound being 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo(8, 8,8)hexacosane having the following formula:
Claim 9
Dependent Claim
35 words
A compound according to claim 6 wherein each D is oxygen; each A is ethylene; and m, n and p are each the integer 2, said compound being 4,7,10, 16,19,22,27,30,33-nonaoxa-1,13-diazabicyclo(11,11, 11)pentatriacontane having the following formula:
Claim 10
Dependent Claim
37 words
A compound according to claim 6 wherein each D is oxygen; each A is ethylene; and m and n are the integer 1 and p is the integer 2; said compound being 4,7,10,16,19,24,27-heptaoxa-1,13-diazabicyclo(8,8,11)nonacosane having the following formula:
Claim 11
Dependent Claim
37 words
A compound according to claim 6 wherein: each D is oxygen; each A is ethylene; and m and n are each the integer 2and p is the integer 1, said compound being 4,7,10,16,19,22,27,30-octaoxa-1,13-diazabicyclo(8,11,11)dotriacontane having the following formula:
Claim 12
Dependent Claim
44 words
A compound according to claim 3 wherein: each D in one bridge is sulfur, all other D members being oxygen; each A is ethylene; and m, n, and p are each the iNteger 1; said compound being 4,7,13, 16-tetraoxa-21,24-dithia-1,10-diazabicyclo(8,8,8) hexacosane having the following formula:
Claim 13
Dependent Claim
42 words
A compound according to claim 3 wherein: each D in one bridge is oxygen; other D members are sulfur; each A is ethylene; and m, n and p are each the integer 1; said compound being 4,7-dioxa-13,16,21,24-tetrathia-1,10-diazabicyclo(8,8,8) hexacosane having the following formula:
Claim 14
Dependent Claim
34 words
A compound according to claim 3 wherein: each D is sulfur; each A is ethylene; and n, m and p are each the integer 1; said compound being 4,7,13, 16,21,24-hexathia-1,10-diazabicyclo(8,8,8)hexacosane having the following formula:
Claim 15
Dependent Claim
37 words
A compound according to claim 6 wherein: each D is oxygen; each A is ethylene; and m and p are each the integer 1 and n is O; said compound being 4,7,13,16,21-pentaoxa-1,10-diazabicyclo(8,8, 5)tricosane having the following formula:
Claim 16
Dependent Claim
43 words
A compound according to claim 2 wherein: each D in one bridge is methylene, all other D members are oxygen; each A is ethylene; and m, n and p are each the integer 1; said compound being 4,7,13, 16-tetraoxa-1,10-diazabicyclo(8,8,8)hexacosane having the following formula:
Claim 17
Dependent Claim
37 words
A compound according to claim 6 wherein: each D is oxygen; each A is ethylene; and m and n are the integer O and p is the integer 1; said compound being 4,7,13,18-tetraoxa-1,10-diazabicyclo(5,5,8)eicosane having the following formula:
Claim 18
Dependent Claim
59 words
A compound according to claim 3 wherein: each D in one bridge is oxygen, each D in one bridge is sulfur, and in the third bridge one D is oxygen and the other D is sulfur; each A is ethylene; and m, n, and p are each the integer 1; said compound being 4,13,16-trioxa-7,21,24-trithia-1,10-diazabicyclo(8,8,8) hexacosane having the following formula:
Claim 19
Dependent Claim
42 words
A compound according to claim 5 wherein each D is oxygen; A is a member selected from the group consisting of ethylene, and O-phenylene; and m, n and p are the integer 1, said compound being 4,11,17,20,25, 28-hexaoxa-1,14-diazatricyclo(12,8,8,05,10)-triaconta-5,7,9-triene having the following formula:
Claim 20
Dependent Claim
43 words
A compound according to claim 5 wherein each D is oxygen; A is a member selected from the group consisting of ethylene and O-phenylene; and m, n and p are the integer 1, said compound being 4,11,17,24,29, 32-hexaoxa-1,14-diazatetracyclo(12,12,8,05,10,18,23) tetratriaconta-5,7,9,18,20,22-hexaene having the following formula:
Claim 21
Dependent Claim
45 words
A compound according to claim 5 wherein: each D is oxygen; A is a member selected from the group consisting of ethylene and o-phenylene; and m and n are the integer 0 and p is 1; said compound being 4,11,17,22-tetraoxa-1,14-diazatricyclo(12,5, 5,05,10)tetracosa-5,7,9-triene having the following formula:
Claim 22
Dependent Claim
39 words
A compound according to claim 4 wherein: each D in two bridges is oxygen and in the third bridge is NH; A is ethylene; and m, n, and p are 1; said compound being 4,7,13,16-tetraoxa-1,10,21,24-tetraazabicyclo(8,8,8)hexacosane having the following formula:
Claim 23
Dependent Claim
42 words
A compound according to claim 4 wherein: each D in two bridges is NH and in the third bridge is oxygen; A is ethylene; and m, n, and p are the integer 1; said compound being 4,7-dioxa-1, 10,13,16,21,24-hexaazabicyclo(8,8,8)hexacosane having the following formula:
Claim 24
Dependent Claim
43 words
A compound according to claim 4 wherein: each D in two bridges is oxygen and in the third bridge is N-CH3; A is ethylene; and m, n, and p are the integer 1; said compound being 21,24 -dimethyl-4,7,13,16-tetraoxa-1,10,21, 24-tetraazabicyclo(8,8,8)hexacosane having the following formula:
Claim 25
Dependent Claim
43 words
A compound according to claim 4 wherein each D in two bridges is N-CH3 and in the third bridge is oxygen; A is ethylene; and m, n and p are each the integer 1; said compound being 13,16,21,24-tetramethyl-4,7-dioxa-1,10,13, 16,21,24-hexaazabicyclo(8,8,8)hexacosane having the following formula:
References Cited (Backward Citations)
US3531468A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-06-09 | 1978-12-09 | 1979-06-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-06-09 | 1982-12-09 | 1983-06-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-06-09 | 1986-12-09 | 1987-06-10 | $7700.00 | Window Closed / Lapsed |