CS195332B2 - Method of producing indazolyl-/4/-oxy-propanolamines - Google Patents
Method of producing indazolyl-/4/-oxy-propanolamines Download PDFInfo
- Publication number
- CS195332B2 CS195332B2 CS772839A CS283977A CS195332B2 CS 195332 B2 CS195332 B2 CS 195332B2 CS 772839 A CS772839 A CS 772839A CS 283977 A CS283977 A CS 283977A CS 195332 B2 CS195332 B2 CS 195332B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compound
- oxy
- acetyl
- indazolyl
- epoxypropoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- -1 indazolyl- Chemical group 0.000 title description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 3
- 230000005764 inhibitory process Effects 0.000 abstract description 3
- 230000000747 cardiac effect Effects 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WDEGJQYOPQDMHW-UHFFFAOYSA-N n-(2-methyl-3-phenylmethoxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(OCC=2C=CC=CC=2)=C1C WDEGJQYOPQDMHW-UHFFFAOYSA-N 0.000 description 1
- URDSHYOWFGTOCY-UHFFFAOYSA-N n-methylsulfanylpropan-2-amine Chemical compound CSNC(C)C URDSHYOWFGTOCY-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000003414 pharmaceutical glidant Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2619164A DE2619164C2 (de) | 1976-04-30 | 1976-04-30 | Indazolyl-(4)-oxy-propanolamine, Verfahren zu ihrer Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195332B2 true CS195332B2 (en) | 1980-01-31 |
Family
ID=5976768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS772839A CS195332B2 (en) | 1976-04-30 | 1977-04-29 | Method of producing indazolyl-/4/-oxy-propanolamines |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4143149A (en, 2012) |
| JP (1) | JPS52133982A (en, 2012) |
| AR (1) | AR213114A1 (en, 2012) |
| AT (1) | AT350560B (en, 2012) |
| AU (1) | AU508791B2 (en, 2012) |
| BE (1) | BE853949A (en, 2012) |
| CA (1) | CA1082201A (en, 2012) |
| CH (1) | CH626351A5 (en, 2012) |
| CS (1) | CS195332B2 (en, 2012) |
| DD (1) | DD129443A5 (en, 2012) |
| DE (1) | DE2619164C2 (en, 2012) |
| DK (1) | DK137956C (en, 2012) |
| ES (1) | ES458176A1 (en, 2012) |
| FI (1) | FI771308A7 (en, 2012) |
| FR (1) | FR2349576A1 (en, 2012) |
| GB (1) | GB1518630A (en, 2012) |
| HU (1) | HU174675B (en, 2012) |
| IE (1) | IE44742B1 (en, 2012) |
| LU (1) | LU77227A1 (en, 2012) |
| NL (1) | NL7704530A (en, 2012) |
| PL (1) | PL103682B1 (en, 2012) |
| SE (1) | SE7704829L (en, 2012) |
| SU (1) | SU679138A3 (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314943A (en) * | 1977-07-13 | 1982-02-09 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| US4495352A (en) * | 1979-02-13 | 1985-01-22 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| DE2905877A1 (de) | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| CA1156661A (en) * | 1980-02-25 | 1983-11-08 | Hoffmann-La Roche Limited | Phenoxy-aminopropanol derivatives |
| DE3023369A1 (de) | 1980-06-23 | 1982-01-14 | Boehringer Mannheim Gmbh, 6800 Mannheim | Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3131146A1 (de) * | 1981-08-06 | 1983-02-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue heteroaryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| JP2001163854A (ja) * | 1999-09-28 | 2001-06-19 | Nippon Nohyaku Co Ltd | チオアルキルアミン誘導体及びその製造方法 |
| JP2002105046A (ja) * | 2000-09-25 | 2002-04-10 | Nippon Nohyaku Co Ltd | チオアルキルアミン−ｓ−酸化体及びその塩類 |
| WO2002100833A1 (fr) * | 2001-06-12 | 2002-12-19 | Sumitomo Pharmaceuticals Company, Limited | Inhibiteurs de rho kinase |
| US11173144B2 (en) * | 2016-05-13 | 2021-11-16 | The Board Of Trustees Of The Leland Stanford Junior University | Adrenergic receptor modulating compounds and methods of using the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3843678A (en) * | 1971-03-15 | 1974-10-22 | Tenneco Chem | Process for the production of substituted indazoles |
| CA1001161A (en) * | 1972-05-05 | 1976-12-07 | Burton K. Wasson | 5-(3-substituted amino-2-hydroxypropoxy)1,3-disubstituted pyrazoles and method of preparation |
| GB1435943A (en) * | 1973-02-07 | 1976-05-19 | Delmar Chem | Indazole-derived tertiary amines |
-
1976
- 1976-04-30 DE DE2619164A patent/DE2619164C2/de not_active Expired
-
1977
- 1977-04-16 ES ES458176A patent/ES458176A1/es not_active Expired
- 1977-04-25 SU SU772473627A patent/SU679138A3/ru active
- 1977-04-25 FI FI771308A patent/FI771308A7/fi not_active Application Discontinuation
- 1977-04-25 US US05/790,648 patent/US4143149A/en not_active Expired - Lifetime
- 1977-04-25 AR AR267336A patent/AR213114A1/es active
- 1977-04-25 DD DD7700198591A patent/DD129443A5/xx unknown
- 1977-04-26 JP JP4835077A patent/JPS52133982A/ja active Pending
- 1977-04-26 BE BE177010A patent/BE853949A/xx unknown
- 1977-04-26 AU AU24593/77A patent/AU508791B2/en not_active Expired
- 1977-04-26 NL NL7704530A patent/NL7704530A/xx not_active Application Discontinuation
- 1977-04-27 SE SE7704829A patent/SE7704829L/ unknown
- 1977-04-27 CH CH524177A patent/CH626351A5/de not_active IP Right Cessation
- 1977-04-27 DK DK184377A patent/DK137956C/da active
- 1977-04-28 IE IE854/77A patent/IE44742B1/en unknown
- 1977-04-28 FR FR7712887A patent/FR2349576A1/fr active Granted
- 1977-04-28 LU LU77227A patent/LU77227A1/xx unknown
- 1977-04-28 AT AT303477A patent/AT350560B/de not_active IP Right Cessation
- 1977-04-28 PL PL1977197704A patent/PL103682B1/pl unknown
- 1977-04-29 CA CA277,405A patent/CA1082201A/en not_active Expired
- 1977-04-29 GB GB17995/77A patent/GB1518630A/en not_active Expired
- 1977-04-29 CS CS772839A patent/CS195332B2/cs unknown
- 1977-04-29 HU HU77BO1664A patent/HU174675B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2349576A1 (fr) | 1977-11-25 |
| DK184377A (da) | 1977-10-31 |
| FI771308A7 (en, 2012) | 1977-10-31 |
| DK137956C (da) | 1978-11-06 |
| AU508791B2 (en) | 1980-04-03 |
| US4143149A (en) | 1979-03-06 |
| DE2619164A1 (de) | 1977-11-17 |
| ES458176A1 (es) | 1978-04-01 |
| IE44742B1 (en) | 1982-03-10 |
| CA1082201A (en) | 1980-07-22 |
| DE2619164C2 (de) | 1985-07-11 |
| AT350560B (de) | 1979-06-11 |
| PL197704A1 (pl) | 1978-04-24 |
| ATA303477A (de) | 1978-11-15 |
| IE44742L (en) | 1977-10-30 |
| GB1518630A (en) | 1978-07-19 |
| DD129443A5 (de) | 1978-01-18 |
| NL7704530A (nl) | 1977-11-01 |
| FR2349576B1 (en, 2012) | 1980-03-21 |
| CH626351A5 (en, 2012) | 1981-11-13 |
| SU679138A3 (ru) | 1979-08-05 |
| AR213114A1 (es) | 1978-12-15 |
| BE853949A (fr) | 1977-10-26 |
| LU77227A1 (en, 2012) | 1978-06-01 |
| SE7704829L (sv) | 1977-10-31 |
| DK137956B (da) | 1978-06-12 |
| JPS52133982A (en) | 1977-11-09 |
| PL103682B1 (pl) | 1979-07-31 |
| HU174675B (hu) | 1980-03-28 |
| AU2459377A (en) | 1978-11-02 |
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