US4115575A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-(3-Amino-2-hydroxy-propoxy)-pyrazines
Assignee: Novartis Corp
•
Filing: 1977-01-07
•
Granted: 1978-09-19
•
Expires: 1997-01-07
Abstract
Abstract Heterocyclic compounds of the formula ##STR1## wherein Het denotes optionally substituted pyridazinyl, pyrimidinyl, pyrazinyl or substituted pyridyl, R 1 is hydrogen or methyl and R 2 is lower alkyl, optionally substituted phenyl-lower alkyl, carboxy-lower alkyl or functionally modified carboxy-lower alkyl, their condensation products with aldehydes, ketones or carbonic acid and their N-oxides, which are valuable (cardioselective) β-rezeptor blocking agents, and/or (cardioselective) β-rezeptor-stimulants.
Inventors
- 👤 Jorg Frei
- 👤 Knut A. Jaeggi
- 👤 Franz Ostermayer
- 👤 Herbert Schroter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:50
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/36; C07D213/40; C07D213/38; C07D213/54; C07D213/57; C07D213/60; C07D213/61; C07D213/62; C07D213/63; C07D213/69; C07D213/72; C07D213/75; C07D213/78; C07D213/81; C07D213/82; C07D213/84; C07D213/85; C07D213/89; C07D263/00; C07D263/02; C07D263/04; C07D263/06
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
55 words
A compound of the formula ##STR84## wherein R 1a is hydrogen or methyl, R 2e is methyl or 2-phenylethyl, R 3c is hydrogen, hydroxy, bromine, methyl, 2-methoxyethyl or 2-methoxycarbonylaminoethyl, and R 4c is hydrogen, chlorine, methoxy, 2-methoxyethoxy, allyloxy, methylthio, ethylthio, morpholino, 4-hydroxypiperidino, dimethylamino, isopropylamino, phenylthio or N'-methylpiperazino their antipodes or a therapeutically acceptable salt thereof.
Claim 2
Dependent Claim
55 words
A compound of the formula ##STR84## wherein R 1a is hydrogen or methyl, R 2e is methyl or 2-phenylethyl, R 3c is hydrogen, hydroxy, bromine, methyl, 2-methoxyethyl or 2-methoxycarbonylaminoethyl, and R 4c is hydrogen, chlorine, methoxy, 2-methoxyethoxy, allyloxy, methylthio, ethylthio, morpholino, 4-hydroxypiperidino, dimethylamino, isopropylamino, phenylthio or N'-methylpiperazino their antipodes or a therapeutically acceptable salt thereof.
Claim 3
Dependent Claim
17 words
The fumarate salt of the compound as claimed in claim 1 being 3-ethylthio-2-(3 1 -isopropylamino-2 1 -hydroxy-propoxy)-pyrazine.
Claim 4
Dependent Claim
15 words
A compound as claimed in claim 1 being 3-ethylthio-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof.
Claim 5
Dependent Claim
15 words
A compound as claimed in claim 1 being 3-ethylthio-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof.
Claim 6
Dependent Claim
9 words
The hydrochloride salt of the compound of claim 4.
Claim 7
Dependent Claim
15 words
A compound as claimed in claim 1 being 3-methylthio-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof.
Claim 8
Dependent Claim
25 words
The fumarate salt of the compound of claim 6 formed with 1 mol of fumaric acid and 2 mol of the compound of claim 6.
Claim 9
Dependent Claim
15 words
A compound as claimed in claim 1 being 3-chloro-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof.
Claim 10
Dependent Claim
15 words
A compound as claimed in claim 1 being 3-methoxy-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof.
Claim 11
Dependent Claim
9 words
The hydrochloride salt of the compound of claim 9.
Claim 12
Dependent Claim
77 words
A pharmaceutical preparation useful as β-receptor blocking agent in the treatment of angina pectoris, hypertonia and disturbances of the rhythm of the heart comprising a therapeutically effective amount of a compound of the formula (Iae) as claimed in claim 1 wherein R 1a and R 2e have the meanings given, R 3c and R 4c have the meanings given except for hydrogen or a therapeutically acceptable salt of such a compound together with a pharmaceutically usable excipient.
Claim 13
Dependent Claim
58 words
A pharmaceutical preparation useful as β-receptor blocking agent in the treatment of angina pectoris, hypertonia and disturbances of the rhythm of the heart as claimed in claim 11 comprising a therapeutically effective amount of a compound selected from the group consisting of 3-ethylthio-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine, 3-ethylthio-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine, 3-methylthio-2-(3'-tert.-butylamino-2'-hydroxypropoxy)-pyrazine, 3-chloro-2-(3'-tert.-butylamino-2'-hydroxypropoxy)-pyrazine, 3-methoxy-2-(3'-isopropylamino-2'-hydroxypropoxy)-pyrazine or therapeutically acceptable salts thereof together with a pharmaceutically usable excipient.
Claim 14
Dependent Claim
47 words
A pharmaceutical preparation useful as β-receptor blocking agent in the treatment of angina pectoris, hypertonia and disturbances of the rhythm of the heart as claimed in claim 12 comprising a therapeutically effective amount of 3-ethylthio-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof together with a pharmaceutically usable excipient.
Claim 15
Dependent Claim
64 words
A pharmaceutical preparation useful as cardiotonic in the treatment of insufficiency of the cardiac muscle comprising a therapeutically effective amount of a compound of the formula (Iae) as claimed in claim 1 wherein R 1a and R 2e have the meanings given, R 3c and R 4c denote hydrogen or a therapeutically acceptable salt of such a compound together with a pharmaceutically usable excipient.
Claim 16
Dependent Claim
79 words
A method of producing a β-receptor blocking effect in the treatment of angina pectoris, hypertonia and disturbances of the rhythm of the heart in a warm-blooded animal comprising the administration thereof of a therapeutically effective amount of a compound of the formula (Iae) as claimed in claim 1 wherein R 1a and R 2e have the meanings given, R 3c and R 4c have the meanings given except for hydrogen, or a therapeutically acceptable salt of such a compound.
Claim 17
Dependent Claim
60 words
A method of producing a β-receptor blocking effect in the treatment of angina pectoris, hypertonia and disturbances of the rhythm of the heart in a warm-blooded animal as claimed in claim 15 comprising the administration thereof of a therapeutically effective amount of a compound selected from the group consisting of 3-ethylthio-2-(3'-isopropylamino-2'-hydroxypropoxy)-pyrazine, 3-ethylthio-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine, 3-methylthio-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine, 3-chloro-2-(3'-tert.-butylamino-2-hydroxy-propoxy)-pyrazine, 3-methoxy-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine or therapeutically acceptable salts thereof.
Claim 18
Dependent Claim
49 words
A method of producing a β-receptor blocking effect in the treatment of angina pectoris, hypertonia and disturbances of the rhythm of the heart in a warm-blooded animal as claimed in claim 15 comprising the administration thereto of a therapeutically effective amount of 3-ethylthio-2-(3'-tert.-butylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof.
Claim 19
Dependent Claim
68 words
A method of producing a β-receptor stimulating effect in the treatment of insufficiency of the cardiac muscle in a warm-blooded animal comprising the administration thereto of a therapeutically effective amount of a compound of the formula (Iae) as claimed in claim 1, wherein R 1a and R 2e have the meanings given, R 3c and R 4c denote hydrogen, or a therapeutically acceptable salt of such a compound.
Claim 20
Dependent Claim
13 words
The compound as claimed in claim 1 being 2-(3 1 -isopropylamino-2 1 -hydroxy-propoxy)-pyrazine.
Claim 21
Dependent Claim
9 words
The dihydrochloride salt of the compound of claim 19.
Claim 22
Dependent Claim
9 words
The fumarate salt of the compound of claim 18.
Claim 23
Dependent Claim
41 words
A pharmaceutical preparation useful as cardiotonic in the treatment of isufficiency of the cardiac muscle comprising a therapeutically effective amount of the compound 2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine as claimed in claim 1 or a therapeutically acceptable salt thereof together with a pharmaceutically usable excipient.
Claim 24
Dependent Claim
45 words
A method of producing a β-receptor stimulating effect in the treatment of insufficiency of the cardiac muscle in a warm-blooded animal comprising the administration thereto of a therapeutically effective amount of the compound 2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine as claimed in claim 1 or a therapeutically acceptable salt thereof.
Claim 25
Dependent Claim
47 words
A pharmaceutical preparation useful as β-receptor blocking agent in the treatment of angina pectoris, hyper-tonia and disturbances of the rhythm of the heart as claimed in claim 12 comprising a therapeutically effective amount of 3-ethylthio-2-(3'-isopropylamino-2'-hydroxy-propoxy)-pyrazine or a therapeutically acceptable salt thereof together with a pharmaceutically usable excipient.
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) | 1981-09-18 | 1982-03-20 | 1982-09-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-18 | 1986-03-20 | 1986-09-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-18 | 1990-03-20 | 1990-09-19 | $7700.00 | Window Closed / Lapsed |