US4337207A
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Biologically active catecholamine derivatives
Assignee: CALIFORNIA A CORP F CALIF, University of, Regents of
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Filing: 1980-09-04
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Granted: 1982-06-29
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Expires: 2000-09-04
Abstract
Abstract Biologically active derivatives of norepinephrine are disclosed. Such derivatives are catecholamines wherein isoproterenol is modified by extending the isopropyl functional grouping to an alkyl, aryl, or alkyl-aryl chain of variable length where said chain terminates in a carboxylic acid functional group, or in a substituted amide functional group. Such derivatives are beta -adrenergic and a number of such derivatives e.g., 6-( beta -3,4-dihydroxyphenyl- beta -hydroxy)-ethylamino heptanoic acid p-toluide, 6-( beta -3,4-dihydroxyphenyl- beta -hydroxy)-ethylamino heptanoic acid para-n-butyl anilide; 6-( beta ,3,4-dihydroxyphenyl- beta -hydroxy)-ethylamino heptanoic acid para-methoxy anilide; 6-( beta -3,4-dihydroxyphenyl- beta -hydroxy)-ethylamino heptanoic acid paratrifluoromethyl anilide; and 6-( beta -3,4-dihydroxyphenyl- beta -hydroxy)-ethylamino heptanoic acid N-methyl para-toluide display a beta -adrenergic activity at least several orders of magnitude greater than isoproterenol itself. Several methods of producing such active derivatives are also disclosed.
Inventors
- 👤 Murray Goodman
- 👤 Michael S. Verlander
- 👤 Kenneth A. Jacobson
- 👤 Kenneth L. Melmon
- 👤 Neal Castagnoli
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 04:58
CPC Classifications
C; C07; C07C; C07C233/00
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
25 words
β-adrenergic compounds having the formula: ##STR31## wherein n=1 to 15, and R is NHR', where R' is H or an alkyl, aryl, or alkyl-aryl substituent.
Claim 2
Dependent Claim
25 words
β-adrenergic compounds having the formula: ##STR31## wherein n=1 to 15, and R is NHR', where R' is H or an alkyl, aryl, or alkyl-aryl substituent.
Claim 3
Dependent Claim
32 words
β-adrenergic compounds in the protonated form: ##STR32## wherein n=1 to 15, R is NHR', where R' is an H or alkyl, aryl, or alkyl-aryl substituent and X.sup.⊖ is a pharmaceutically acceptable anion.
Claim 4
Dependent Claim
32 words
β-adrenergic compounds in the protonated form: ##STR32## wherein n=1 to 15, R is NHR', where R' is an H or alkyl, aryl, or alkyl-aryl substituent and X.sup.⊖ is a pharmaceutically acceptable anion.
Claim 5
Dependent Claim
9 words
The compounds of claim 1 wherein n=1 to 5.
Claim 6
Dependent Claim
7 words
The compounds of claim 1 wherein n=4.
Claim 7
Dependent Claim
16 words
β-adrenergic compounds having the formula: ##STR33## wherein n=1 to 15, and R is an aniline derivative.
Claim 8
Dependent Claim
16 words
β-adrenergic compounds having the formula: ##STR33## wherein n=1 to 15, and R is an aniline derivative.
Claim 9
Dependent Claim
7 words
The compounds of claim 5 wherein n=4.
Claim 10
Dependent Claim
11 words
The compounds of claim 5 wherein the aniline derivative is ##STR34##
Claim 11
Dependent Claim
7 words
The compounds of claim 7 wherein n=4.
Claim 12
Dependent Claim
11 words
The compounds of claim 5 wherein the aniline derivative is ##STR35##
Claim 13
Dependent Claim
7 words
The compounds of claim 9 wherein n=4.
Claim 14
Dependent Claim
11 words
The compounds of claim 5 wherein the aniline derivative is ##STR36##
Claim 15
Dependent Claim
7 words
The compounds of claim 11 wherein n=4.
Claim 16
Dependent Claim
11 words
The compounds of claim 5 wherein the aniline derivative is ##STR37##
Claim 17
Dependent Claim
7 words
The compounds of claim 13 wherein n=4.
Claim 18
Dependent Claim
11 words
The compounds of claim 5 wherein the aniline derivative is: ##STR38##
Claim 19
Dependent Claim
7 words
The compounds of claim 15 wherein n=4.
Claim 20
Dependent Claim
16 words
β-adrenergic compounds having the formula: ##STR39## wherein n=1 to 15, and R is an alkyl amine.
Claim 21
Dependent Claim
16 words
β-adrenergic compounds having the formula: ##STR39## wherein n=1 to 15, and R is an alkyl amine.
Claim 22
Dependent Claim
7 words
The compounds of claim 17 wherein n=4.
Claim 23
Dependent Claim
17 words
The compounds of claim 17 wherein the alkyl amine is --NH(CH 2 ) 3 --CH 3 .
Claim 24
Dependent Claim
7 words
The compounds of claim 19 wherein n=4.
Claim 25
Dependent Claim
17 words
β-adrenergic compounds having the formula: ##STR40## wherein n=1 to 15, and R is a cyclo alkyl amine.
Claim 26
Dependent Claim
17 words
β-adrenergic compounds having the formula: ##STR40## wherein n=1 to 15, and R is a cyclo alkyl amine.
Claim 27
Dependent Claim
7 words
The compounds of claim 21 wherein n=4.
Claim 28
Dependent Claim
12 words
The compounds of claim 21 wherein the cyclo alkyl amine is ##STR41##
Claim 29
Dependent Claim
7 words
The compounds of claim 23 wherein n=4.
Claim 30
Dependent Claim
12 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid p-toluide and pharmaceutically acceptable salts thereof.
Claim 31
Dependent Claim
12 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid p-toluide and pharmaceutically acceptable salts thereof.
Claim 32
Dependent Claim
13 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid para-n-butyl anilide and pharmaceutically acceptable salts thereof.
Claim 33
Dependent Claim
13 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid para-n-butyl anilide and pharmaceutically acceptable salts thereof.
Claim 34
Dependent Claim
13 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid para-methoxy anilide and pharmaceutically acceptable salts thereof.
Claim 35
Dependent Claim
13 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid para-methoxy anilide and pharmaceutically acceptable salts thereof.
Claim 36
Dependent Claim
14 words
The compound 6-(β-3,4 dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid para-trifluoromethyl anilide and pharmaceutically acceptable salts thereof.
Claim 37
Dependent Claim
14 words
The compound 6-(β-3,4 dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid para-trifluoromethyl anilide and pharmaceutically acceptable salts thereof.
Claim 38
Dependent Claim
13 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid N-methyl para-toluide and pharmaceutically acceptable salts thereof.
Claim 39
Dependent Claim
13 words
The compound 6-(β-3,4-dihydroxy phenyl-β-hydroxy)-ethylamino heptanoic acid N-methyl para-toluide and pharmaceutically acceptable salts thereof.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-06-28 | 1985-12-28 | 1986-06-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-06-28 | 1989-12-28 | 1990-06-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-06-28 | 1993-12-28 | 1994-06-29 | $7700.00 | Window Closed / Lapsed |