NO894423L - Fremgangsmaate for fremstilling av terapeutisk aktive propanolaminer. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk aktive propanolaminer.Info
- Publication number
- NO894423L NO894423L NO89894423A NO894423A NO894423L NO 894423 L NO894423 L NO 894423L NO 89894423 A NO89894423 A NO 89894423A NO 894423 A NO894423 A NO 894423A NO 894423 L NO894423 L NO 894423L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- propanolamines
- preparation
- procedure
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000003152 propanolamines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- BIJYXIOVXFBJEP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC=CC=C1OCC1OC1 BIJYXIOVXFBJEP-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- -1 3-[[[imidazo[1,2-a]pyridin-2-yl]-1-methyl-ethyl]amino]-1-(2-cyano-phenoxy)-propan-2-ol maleate Chemical compound 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000004410 intraocular pressure Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UJUKHOATWVVDER-UHFFFAOYSA-N 1-amino-1-phenoxypropan-1-ol Chemical class CCC(N)(O)OC1=CC=CC=C1 UJUKHOATWVVDER-UHFFFAOYSA-N 0.000 description 1
- XVOJLLPQHOPVPP-UHFFFAOYSA-N 2-(1-imidazo[1,2-a]pyridin-2-ylpropan-2-yl)isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(C)CC1=CN(C=CC=C2)C2=N1 XVOJLLPQHOPVPP-UHFFFAOYSA-N 0.000 description 1
- OMHZNHXADDHHJC-UHFFFAOYSA-N 2-[2-hydroxy-3-[(1-imidazo[1,2-a]pyridin-3-yl-2-methylpropan-2-yl)amino]propoxy]benzonitrile Chemical compound C=1N=C2C=CC=CN2C=1CC(C)(C)NCC(O)COC1=CC=CC=C1C#N OMHZNHXADDHHJC-UHFFFAOYSA-N 0.000 description 1
- UAFQGHLRYNSXJD-UHFFFAOYSA-N 2-imidazo[1,2-a]pyridin-3-ylethanamine Chemical compound C1=CC=CN2C(CCN)=CN=C21 UAFQGHLRYNSXJD-UHFFFAOYSA-N 0.000 description 1
- FGLBSLMDCBOPQK-UHFFFAOYSA-N 2-nitropropane Chemical compound CC(C)[N+]([O-])=O FGLBSLMDCBOPQK-UHFFFAOYSA-N 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000282567 Macaca fascicularis Species 0.000 description 1
- 206010030043 Ocular hypertension Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000001384 anti-glaucoma Effects 0.000 description 1
- 210000001742 aqueous humor Anatomy 0.000 description 1
- 238000009530 blood pressure measurement Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8814538A FR2638747B1 (fr) | 1988-11-08 | 1988-11-08 | Derives de phenyloxypropanolamines, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO894423D0 NO894423D0 (no) | 1989-11-07 |
| NO894423L true NO894423L (no) | 1990-05-09 |
Family
ID=9371654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO89894423A NO894423L (no) | 1988-11-08 | 1989-11-07 | Fremgangsmaate for fremstilling av terapeutisk aktive propanolaminer. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5001132A (de) |
| EP (1) | EP0370852A1 (de) |
| JP (1) | JPH02180883A (de) |
| AU (1) | AU615354B2 (de) |
| CA (1) | CA2002390A1 (de) |
| DK (1) | DK553689A (de) |
| FI (1) | FI895286A0 (de) |
| FR (1) | FR2638747B1 (de) |
| HU (1) | HU205929B (de) |
| IE (1) | IE893578L (de) |
| IL (1) | IL92226A0 (de) |
| NO (1) | NO894423L (de) |
| NZ (1) | NZ231298A (de) |
| PT (1) | PT92226A (de) |
| ZA (1) | ZA898480B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5629345A (en) * | 1993-07-23 | 1997-05-13 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| US5965620A (en) * | 1993-07-23 | 1999-10-12 | Vide Pharmaceuticals | Methods and compositions for ATP-sensitive K+ channel inhibition for lowering intraocular pressure |
| CN111108105B (zh) | 2017-09-22 | 2023-03-31 | 朱比兰特埃皮帕德有限公司 | 作为pad抑制剂的杂环化合物 |
| SG11202003463XA (en) | 2017-10-18 | 2020-05-28 | Jubilant Epipad LLC | Imidazo-pyridine compounds as pad inhibitors |
| CA3080677A1 (en) | 2017-11-06 | 2019-05-09 | Jubilant Prodel LLC | Pyrimidine derivatives as inhibitors of pd1/pd-l1 activation |
| IL274762B2 (en) | 2017-11-24 | 2023-10-01 | Jubilant Episcribe Llc | Novel heterocyclic compounds as PRMT5 inhibitors |
| SG11202008950PA (en) | 2018-03-13 | 2020-10-29 | Jubilant Prodel LLC | Bicyclic compounds as inhibitors of pd1/pd-l1 interaction/activation |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234595A (en) * | 1977-07-13 | 1980-11-18 | Mead Johnson & Company | 3-Indolyl-tertiary butylaminopropanols |
| US4210653A (en) * | 1978-06-27 | 1980-07-01 | Merck & Co., Inc. | Pyridyloxypropanolamines |
| FR2463765A1 (fr) * | 1979-08-17 | 1981-02-27 | Clin Midy | Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire |
| JPS60233074A (ja) * | 1984-05-04 | 1985-11-19 | Hokuriku Seiyaku Co Ltd | イミダゾ〔１，２−ａ〕ピリジン誘導体 |
| IL88619A0 (en) * | 1987-12-15 | 1989-07-31 | Pfizer | Non-peptidic renin inhibitors |
-
1988
- 1988-11-08 FR FR8814538A patent/FR2638747B1/fr not_active Expired - Fee Related
-
1989
- 1989-11-03 EP EP89403024A patent/EP0370852A1/de not_active Withdrawn
- 1989-11-07 NO NO89894423A patent/NO894423L/no unknown
- 1989-11-07 PT PT92226A patent/PT92226A/pt not_active Application Discontinuation
- 1989-11-07 CA CA002002390A patent/CA2002390A1/en not_active Abandoned
- 1989-11-07 FI FI895286A patent/FI895286A0/fi not_active Application Discontinuation
- 1989-11-07 US US07/432,686 patent/US5001132A/en not_active Expired - Fee Related
- 1989-11-07 JP JP1289845A patent/JPH02180883A/ja active Pending
- 1989-11-07 DK DK553689A patent/DK553689A/da not_active Application Discontinuation
- 1989-11-07 HU HU895817A patent/HU205929B/hu unknown
- 1989-11-07 IE IE893578A patent/IE893578L/xx unknown
- 1989-11-07 NZ NZ231298A patent/NZ231298A/en unknown
- 1989-11-07 ZA ZA898480A patent/ZA898480B/xx unknown
- 1989-11-07 IL IL92226A patent/IL92226A0/xx unknown
- 1989-11-08 AU AU44507/89A patent/AU615354B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ZA898480B (en) | 1990-07-25 |
| NZ231298A (en) | 1991-05-28 |
| AU615354B2 (en) | 1991-09-26 |
| JPH02180883A (ja) | 1990-07-13 |
| US5001132A (en) | 1991-03-19 |
| EP0370852A1 (de) | 1990-05-30 |
| HUT52501A (en) | 1990-07-28 |
| CA2002390A1 (en) | 1990-05-08 |
| PT92226A (pt) | 1990-05-31 |
| FI895286A0 (fi) | 1989-11-07 |
| AU4450789A (en) | 1990-05-31 |
| FR2638747A1 (fr) | 1990-05-11 |
| FR2638747B1 (fr) | 1993-12-24 |
| HU205929B (en) | 1992-07-28 |
| NO894423D0 (no) | 1989-11-07 |
| IE893578L (en) | 1990-05-08 |
| DK553689A (da) | 1990-05-09 |
| IL92226A0 (en) | 1990-07-26 |
| HU895817D0 (en) | 1990-01-28 |
| DK553689D0 (da) | 1989-11-07 |
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