IL35378A - Derivatives of 1-amino-3-phenoxy-2-propanol and process of preparation - Google Patents
Derivatives of 1-amino-3-phenoxy-2-propanol and process of preparationInfo
- Publication number
- IL35378A IL35378A IL35378A IL3537870A IL35378A IL 35378 A IL35378 A IL 35378A IL 35378 A IL35378 A IL 35378A IL 3537870 A IL3537870 A IL 3537870A IL 35378 A IL35378 A IL 35378A
- Authority
- IL
- Israel
- Prior art keywords
- propanol
- cyclopropylphenoxy
- hydrochloride
- compound
- formula
- Prior art date
Links
- JZEHWMUIAKALDN-UHFFFAOYSA-N 1-amino-3-phenoxypropan-2-ol Chemical class NCC(O)COC1=CC=CC=C1 JZEHWMUIAKALDN-UHFFFAOYSA-N 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- -1 3-(o-cyclopropylphenoxy) 2-propanol Chemical compound 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Substances 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- AHSPWWYJXLMLAM-UHFFFAOYSA-N 1-(2-cyclopropylphenoxy)-3-(diethylamino)propan-2-ol Chemical compound CCN(CC)CC(O)COC1=CC=CC=C1C1CC1 AHSPWWYJXLMLAM-UHFFFAOYSA-N 0.000 claims 1
- RTAGQMIEWAAKMO-UHFFFAOYSA-N 1-(2-cyclopropylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1C1CC1 RTAGQMIEWAAKMO-UHFFFAOYSA-N 0.000 claims 1
- PHTXELQMXPREHU-UHFFFAOYSA-N 1-(4-cyclopropylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1C1CC1 PHTXELQMXPREHU-UHFFFAOYSA-N 0.000 claims 1
- GIELSRAJZMPBDJ-UHFFFAOYSA-N 1-(cyclopropylamino)-3-(2-cyclopropylphenoxy)propan-2-ol Chemical compound C=1C=CC=C(C2CC2)C=1OCC(O)CNC1CC1 GIELSRAJZMPBDJ-UHFFFAOYSA-N 0.000 claims 1
- AKLYZSZBJHPVTE-UHFFFAOYSA-M [3-(2-cyclopropylphenoxy)-2-hydroxypropyl]-diethyl-methylazanium;iodide Chemical compound [I-].CC[N+](C)(CC)CC(O)COC1=CC=CC=C1C1CC1 AKLYZSZBJHPVTE-UHFFFAOYSA-M 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- CIDZNASUPYMQCG-UHFFFAOYSA-N 3-iodo-3-methylpentane Chemical compound CCC(C)(I)CC CIDZNASUPYMQCG-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ZPHQBFRCXUIIAZ-UHFFFAOYSA-N benzene;hydrochloride Chemical compound Cl.C1=CC=CC=C1 ZPHQBFRCXUIIAZ-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YYMLRIWBISZOMT-UHFFFAOYSA-N n-ethylethanamine;hydroiodide Chemical compound [I-].CC[NH2+]CC YYMLRIWBISZOMT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6937692A FR2068422A1 (enrdf_load_stackoverflow) | 1969-11-03 | 1969-11-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL35378A0 IL35378A0 (en) | 1970-11-30 |
| IL35378A true IL35378A (en) | 1973-11-28 |
Family
ID=9042491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL35378A IL35378A (en) | 1969-11-03 | 1970-09-30 | Derivatives of 1-amino-3-phenoxy-2-propanol and process of preparation |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2361106A2 (fr) * | 1976-08-10 | 1978-03-10 | Mar Pha Etu Et Expl De Marques | Nouvelles terpeno-phenoxy-alkylamines |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1668055B2 (de) * | 1967-03-10 | 1973-09-06 | Farbwerke Hoechst AG, vormals Mei ster Lucius & Bruning, 6000 Frankfurt | Basisch substituierte cyclopentylphenolaether, deren salze mit physiologisch vertraeglichen saeuren und verfahren zu deren herstellung |
-
0
- BE BE758303D patent/BE758303A/xx unknown
-
1969
- 1969-11-03 FR FR6937692A patent/FR2068422A1/fr not_active Withdrawn
-
1970
- 1970-09-30 IL IL35378A patent/IL35378A/en unknown
- 1970-10-29 DE DE2053192A patent/DE2053192C3/de not_active Expired
- 1970-10-30 ES ES385062A patent/ES385062A1/es not_active Expired
- 1970-10-30 GB GB51695/70A patent/GB1294159A/en not_active Expired
- 1970-10-30 NL NL7015922A patent/NL7015922A/xx not_active Application Discontinuation
- 1970-11-02 CH CH1621970A patent/CH533594A/fr not_active IP Right Cessation
- 1970-11-02 DK DK555070AA patent/DK127878B/da unknown
- 1970-11-02 CA CA097,196*7A patent/CA943139A/en not_active Expired
- 1970-11-03 SE SE7014860A patent/SE370392B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2053192C3 (de) | 1974-02-28 |
| BE758303A (fr) | 1971-04-30 |
| ES385062A1 (es) | 1973-03-16 |
| IL35378A0 (en) | 1970-11-30 |
| DE2053192B2 (de) | 1973-07-12 |
| CA943139A (en) | 1974-03-05 |
| FR2068422A1 (enrdf_load_stackoverflow) | 1971-08-27 |
| DK127878B (da) | 1974-01-28 |
| CH533594A (fr) | 1973-02-15 |
| GB1294159A (en) | 1972-10-25 |
| DE2053192A1 (de) | 1971-07-01 |
| SE370392B (enrdf_load_stackoverflow) | 1974-10-14 |
| NL7015922A (enrdf_load_stackoverflow) | 1971-05-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK171748B1 (da) | Stabile opløsningsmiddeladdukter, fremgangsmåde til fremstilling deraf, lægemiddel indeholdende addukterne samt anvendelse af addukterne | |
| US20080275237A1 (en) | Method for Obtaining Pure Tetrahydrocannabinol | |
| HU193161B (en) | Process for preparing new n-alkyl-norscopines | |
| DK143698B (da) | Analogifremgangsmaade til fremstilling af 1-aminoalkyl-2-aryl-cyclohexylalkoholer og estere eller salte deraf | |
| PT93674A (pt) | Processo para a preparacao de cromanos substituidos para o tratamento da asma, artrite e doencas relacionadas | |
| HU178532B (en) | Process for producing 1,2,4,5-tetraalkyl-4-aryl-piperidine derivatives | |
| CS205085B2 (en) | Method of producing hydroxy-and oxoderivatives of arylthio-perhydro-aza-heterocycles | |
| JPS596853B2 (ja) | ２−（２；− メチル −３；− トリフルオルメチル − アニリノ ）− ニコチンサンノ ｎ− メチル −ｄ− グルカミンエンノ セイホウ | |
| NO803693L (no) | 2,3-indoldion-derivater. | |
| IL35378A (en) | Derivatives of 1-amino-3-phenoxy-2-propanol and process of preparation | |
| CN120359215A (zh) | 用于制备喹唑啉酮衍生物的方法 | |
| EP0440684B1 (en) | Novel s-timolol derivative and process for its preparation | |
| US3179665A (en) | 9-(n-ethyl and n-propyl piperidyl-3'-methyl)-thioxanthenes | |
| US3868418A (en) | Novel N-(ortho- and para-nitrobenzoyl)-sulfoximine intermediates and process for their production | |
| SU1053749A3 (ru) | Способ получени 1,2-бис-(никотинамидо)-пропана или его солей с фармацевтически приемлемой кислотой | |
| US3637759A (en) | Chromanes | |
| US3070624A (en) | Glycyrrhetinic acid dialkylaminoalkyl esters | |
| US2941002A (en) | Beta-hydroxy carboxylic acid amides substituted at the nitrogen atom | |
| US3766245A (en) | 3,5-dialkoxyalkoxy-4-substituted benzoic acid esters | |
| JP2018510218A (ja) | ピロールで結合している二価の化合物の化学合成方法、及びその組成物 | |
| US3322778A (en) | Novel ether derivatives of benzmorphans | |
| Rao et al. | Synthesis of 2-(N-disubstituted amino) ethyltriphenylphosphonium bromides | |
| US3855229A (en) | Benzopyran-5-ols | |
| JPS6026387B2 (ja) | シンナミルモラノリン誘導体 | |
| US2624735A (en) | 4,4'-polymethylene-bipiperidinium derivatives |