AU546152B2 - Compounds and method for treatment or prophylaxis of cardiac disorders - Google Patents
Compounds and method for treatment or prophylaxis of cardiac disordersInfo
- Publication number
- AU546152B2 AU546152B2 AU78920/81A AU7892081A AU546152B2 AU 546152 B2 AU546152 B2 AU 546152B2 AU 78920/81 A AU78920/81 A AU 78920/81A AU 7892081 A AU7892081 A AU 7892081A AU 546152 B2 AU546152 B2 AU 546152B2
- Authority
- AU
- Australia
- Prior art keywords
- carbon atoms
- formula
- compound
- aryl
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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- 238000000034 method Methods 0.000 title claims description 48
- 238000011282 treatment Methods 0.000 title claims description 10
- 208000020446 Cardiac disease Diseases 0.000 title claims description 8
- 208000019622 heart disease Diseases 0.000 title claims description 8
- 238000011321 prophylaxis Methods 0.000 title claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 115
- 125000003118 aryl group Chemical group 0.000 claims description 43
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- 125000000217 alkyl group Chemical group 0.000 claims description 41
- -1 acetamido, amino Chemical group 0.000 claims description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 26
- 238000010992 reflux Methods 0.000 claims description 24
- 238000001802 infusion Methods 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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- 239000012153 distilled water Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- RJCGNNHKSNIUAT-UHFFFAOYSA-N ethyl 3-aminopropanoate;hydron;chloride Chemical compound Cl.CCOC(=O)CCN RJCGNNHKSNIUAT-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- QPNAREOPWNRCEQ-UHFFFAOYSA-N methyl 3-[4-[3-[(3-ethoxy-3-oxopropyl)amino]-2-hydroxypropoxy]phenyl]propanoate;hydrochloride Chemical compound Cl.CCOC(=O)CCNCC(O)COC1=CC=C(CCC(=O)OC)C=C1 QPNAREOPWNRCEQ-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- RLXDCJUIXHSXQD-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O.OC(=O)C(O)=O RLXDCJUIXHSXQD-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-L tyrosinate(2-) Chemical compound [O-]C(=O)C(N)CC1=CC=C([O-])C=C1 OUYCCCASQSFEME-UHFFFAOYSA-L 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/02—Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21134080A | 1980-11-28 | 1980-11-28 | |
| US211340 | 1980-11-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7892081A AU7892081A (en) | 1982-06-17 |
| AU546152B2 true AU546152B2 (en) | 1985-08-15 |
Family
ID=22786520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU78920/81A Expired AU546152B2 (en) | 1980-11-28 | 1981-11-16 | Compounds and method for treatment or prophylaxis of cardiac disorders |
Country Status (13)
| Country | Link |
|---|---|
| EP (2) | EP0053434B1 (OSRAM) |
| JP (1) | JPH0617345B2 (OSRAM) |
| KR (1) | KR880001827B1 (OSRAM) |
| AU (1) | AU546152B2 (OSRAM) |
| CA (1) | CA1183148A (OSRAM) |
| DK (1) | DK152491C (OSRAM) |
| EG (1) | EG15685A (OSRAM) |
| GR (1) | GR76307B (OSRAM) |
| IL (1) | IL64346A (OSRAM) |
| NZ (1) | NZ198945A (OSRAM) |
| RO (1) | RO85556B (OSRAM) |
| WO (1) | WO1982001870A1 (OSRAM) |
| ZA (1) | ZA817931B (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053434B1 (en) * | 1980-11-28 | 1986-08-27 | American Hospital Supply Corporation | Compounds and method for treatment or prophylaxis of cardiac disorders |
| US4455317A (en) * | 1981-06-23 | 1984-06-19 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4472301A (en) * | 1982-05-27 | 1984-09-18 | Miles Laboratories, Inc. | Propranolol immunogen and antibodies |
| US4687873A (en) * | 1983-02-03 | 1987-08-18 | The Regents Of The University Of California | Derivatives of β-adrenergic antagonists |
| ATE39245T1 (de) * | 1983-02-03 | 1988-12-15 | Univ California | Beta-adrenergisch antagonistische verbindungen und derivate von beta-adrenergischen antagonisten. |
| DE3836987A1 (de) * | 1988-10-31 | 1990-05-23 | Goedecke Ag | 2-aminocarbonsaeuren und deren derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel |
| DE19943635A1 (de) * | 1999-09-13 | 2001-03-15 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| CN115536537B (zh) * | 2022-09-21 | 2023-09-22 | 华中农业大学 | 普萘洛尔衍生物及其在抑制植物病原菌中的应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1922003C3 (de) * | 1969-04-30 | 1979-10-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | N-(3-Aryloxy-2-hydroxypropyl)-aminocarbonsäuren, deren Ester, Amide und Salze, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung bei der Bekämpfung von Herzinsuffizienz |
| DE2324584A1 (de) * | 1972-06-08 | 1974-01-10 | Ciba Geigy Ag | Neue amine und verfahren zu ihrer herstellung |
| CH580057A5 (OSRAM) * | 1973-04-17 | 1976-09-30 | Ciba Geigy Ag | |
| US4146638A (en) * | 1976-02-17 | 1979-03-27 | Boehringer Ingelheim Gmbh | N-(3-phenoxy-2-hydroxy-propyl)-n-(2-phenyl-2-hydroxy-ethyl)-amines |
| US4241177A (en) * | 1978-08-28 | 1980-12-23 | Syva Company | Propanolol antigen conjugates and antibodies |
| SE8004088L (sv) * | 1980-06-02 | 1981-12-03 | Haessle Ab | Nya substituerade 3-fenoxi-l-alkoxikarbonylalkylamino-propanol-2-er med beta-receptorblockerande egenskaper samt forfarande for deras framstellning, farmaceutiska beredningar innehallande desamma och metod att ... |
| EP0053434B1 (en) * | 1980-11-28 | 1986-08-27 | American Hospital Supply Corporation | Compounds and method for treatment or prophylaxis of cardiac disorders |
-
1981
- 1981-10-29 EP EP81305128A patent/EP0053434B1/en not_active Expired
- 1981-11-11 NZ NZ198945A patent/NZ198945A/en unknown
- 1981-11-16 AU AU78920/81A patent/AU546152B2/en not_active Expired
- 1981-11-16 EP EP81903189A patent/EP0065963B1/en not_active Expired
- 1981-11-16 WO PCT/US1981/001515 patent/WO1982001870A1/en not_active Ceased
- 1981-11-16 ZA ZA817931A patent/ZA817931B/xx unknown
- 1981-11-16 RO RO108294A patent/RO85556B/ro unknown
- 1981-11-16 JP JP56503727A patent/JPH0617345B2/ja not_active Expired - Lifetime
- 1981-11-24 IL IL64346A patent/IL64346A/xx not_active IP Right Cessation
- 1981-11-26 GR GR66621A patent/GR76307B/el unknown
- 1981-11-26 CA CA000390968A patent/CA1183148A/en not_active Expired
- 1981-11-28 KR KR1019810004621A patent/KR880001827B1/ko not_active Expired
- 1981-11-28 EG EG695/81A patent/EG15685A/xx active
-
1982
- 1982-07-27 DK DK334982A patent/DK152491C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| DK152491B (da) | 1988-03-07 |
| EG15685A (en) | 1986-12-30 |
| IL64346A (en) | 1988-12-30 |
| EP0065963A4 (en) | 1983-04-25 |
| RO85556A (ro) | 1985-03-15 |
| WO1982001870A1 (en) | 1982-06-10 |
| JPH0617345B2 (ja) | 1994-03-09 |
| EP0053434B1 (en) | 1986-08-27 |
| DK152491C (da) | 1988-07-25 |
| AU7892081A (en) | 1982-06-17 |
| NZ198945A (en) | 1985-09-13 |
| CA1183148A (en) | 1985-02-26 |
| EP0053434A1 (en) | 1982-06-09 |
| EP0065963A1 (en) | 1982-12-08 |
| JPS57502124A (OSRAM) | 1982-12-02 |
| EP0065963B1 (en) | 1986-01-29 |
| GR76307B (OSRAM) | 1984-08-04 |
| KR830007510A (ko) | 1983-10-21 |
| DK334982A (da) | 1982-07-27 |
| RO85556B (ro) | 1985-03-30 |
| ZA817931B (en) | 1983-03-30 |
| KR880001827B1 (ko) | 1988-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |