CY1518A - 1-phenoxy-3-hydroxyindolyl-alkylamino-2-propanols and preparation - Google Patents
1-phenoxy-3-hydroxyindolyl-alkylamino-2-propanols and preparation Download PDFInfo
- Publication number
- CY1518A CY1518A CY1518A CY151890A CY1518A CY 1518 A CY1518 A CY 1518A CY 1518 A CY1518 A CY 1518A CY 151890 A CY151890 A CY 151890A CY 1518 A CY1518 A CY 1518A
- Authority
- CY
- Cyprus
- Prior art keywords
- compound
- formula
- hydroxy
- hydrogen
- alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 10
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 9
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- 231100000252 nontoxic Toxicity 0.000 claims description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
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- RLHZDXDBSDXXNX-UHFFFAOYSA-N 2-[2-hydroxy-3-[[1-(5-hydroxy-1h-indol-3-yl)-2-methylpropan-2-yl]amino]propoxy]benzonitrile Chemical compound C=1NC2=CC=C(O)C=C2C=1CC(C)(C)NCC(O)COC1=CC=CC=C1C#N RLHZDXDBSDXXNX-UHFFFAOYSA-N 0.000 claims 1
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- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
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- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003437 trachea Anatomy 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
- 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
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50290183A | 1983-06-10 | 1983-06-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1518A true CY1518A (en) | 1990-11-16 |
Family
ID=23999880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1518A CY1518A (en) | 1983-06-10 | 1990-11-16 | 1-phenoxy-3-hydroxyindolyl-alkylamino-2-propanols and preparation |
Country Status (29)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2601008B1 (fr) * | 1986-07-03 | 1990-03-30 | Sanofi Sa | Procede de synthese stereospecifique de derives de l'indole |
| KR101986648B1 (ko) | 2018-04-06 | 2019-06-07 | (유)로뎀건설 | 강관작업구 굴착장치 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB962793A (en) * | 1959-07-13 | 1964-07-01 | Philips Nv | Improvements in or relating to pharmacologically active compounds being substituted tryptamines |
| NL300886A (enrdf_load_stackoverflow) * | 1962-11-23 | |||
| US4314943A (en) * | 1977-07-13 | 1982-02-09 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| CA1116598A (en) * | 1977-07-13 | 1982-01-19 | William T. Comer | 3-indolyl-tertiary butylaminopropanols |
| US4234595A (en) * | 1977-07-13 | 1980-11-18 | Mead Johnson & Company | 3-Indolyl-tertiary butylaminopropanols |
| FR2463765A1 (fr) * | 1979-08-17 | 1981-02-27 | Clin Midy | Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire |
-
1984
- 1984-05-31 NZ NZ208337A patent/NZ208337A/xx unknown
- 1984-06-04 IL IL72008A patent/IL72008A/xx unknown
- 1984-06-06 NO NO842279A patent/NO164471C/no unknown
- 1984-06-06 AT AT0186784A patent/AT381492B/de not_active IP Right Cessation
- 1984-06-06 ES ES533185A patent/ES8507490A1/es not_active Expired
- 1984-06-06 FR FR8408858A patent/FR2549054B1/fr not_active Expired
- 1984-06-06 ZA ZA844277A patent/ZA844277B/xx unknown
- 1984-06-07 FI FI842316A patent/FI78291C/fi not_active IP Right Cessation
- 1984-06-07 YU YU997/84A patent/YU44873B/xx unknown
- 1984-06-07 GR GR74949A patent/GR82208B/el unknown
- 1984-06-07 DE DE19843421252 patent/DE3421252A1/de not_active Ceased
- 1984-06-08 GB GB08414652A patent/GB2141121B/en not_active Expired
- 1984-06-08 SE SE8403112A patent/SE455865B/sv not_active IP Right Cessation
- 1984-06-08 LU LU85410A patent/LU85410A1/fr unknown
- 1984-06-08 HU HU842215A patent/HU191670B/hu not_active IP Right Cessation
- 1984-06-08 DK DK284184A patent/DK162089C/da not_active IP Right Cessation
- 1984-06-08 CH CH2814/84A patent/CH662561A5/de not_active IP Right Cessation
- 1984-06-08 NL NL8401840A patent/NL8401840A/nl active Search and Examination
- 1984-06-08 IT IT8421330A patent/IT1206705B/it active
- 1984-06-08 IE IE1441/84A patent/IE57682B1/en not_active IP Right Cessation
- 1984-06-08 CA CA000456154A patent/CA1217496A/en not_active Expired
- 1984-06-08 JP JP59116767A patent/JPS608262A/ja active Granted
- 1984-06-08 AU AU29238/84A patent/AU569303B2/en not_active Ceased
- 1984-06-08 BE BE0/213109A patent/BE899875A/fr not_active IP Right Cessation
- 1984-06-09 KR KR1019840003251A patent/KR900005021B1/ko not_active Expired
-
1987
- 1987-09-29 MY MYPI87002203A patent/MY102077A/en unknown
-
1990
- 1990-01-08 SG SG10/90A patent/SG1090G/en unknown
- 1990-02-22 HK HK146/90A patent/HK14690A/xx not_active IP Right Cessation
- 1990-11-16 CY CY1518A patent/CY1518A/en unknown
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