PL83310B1 - Aminopropanol derivatives[gb1377787a] - Google Patents
Aminopropanol derivatives[gb1377787a] Download PDFInfo
- Publication number
- PL83310B1 PL83310B1 PL15350272A PL15350272A PL83310B1 PL 83310 B1 PL83310 B1 PL 83310B1 PL 15350272 A PL15350272 A PL 15350272A PL 15350272 A PL15350272 A PL 15350272A PL 83310 B1 PL83310 B1 PL 83310B1
- Authority
- PL
- Poland
- Prior art keywords
- amino
- formula
- propanol
- dichlorophenyl
- compounds
- Prior art date
Links
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 31
- SDQHHIMPZYXBMS-UHFFFAOYSA-N 2-amino-3-(3,4-dichlorophenyl)propan-1-ol Chemical compound OCC(N)CC1=CC=C(Cl)C(Cl)=C1 SDQHHIMPZYXBMS-UHFFFAOYSA-N 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000012279 sodium borohydride Substances 0.000 claims description 14
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 14
- 150000004702 methyl esters Chemical class 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- -1 2-amino-3- (2,6-dichlorophenyl) propanol Chemical compound 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- WXMQDCRVBPMUBV-UHFFFAOYSA-N 1-anilinopropan-1-ol Chemical class CCC(O)NC1=CC=CC=C1 WXMQDCRVBPMUBV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 claims description 5
- DDOXQIODUSXROP-UHFFFAOYSA-N 2-amino-3-(3-chlorophenyl)propan-1-ol Chemical compound OCC(N)CC1=CC=CC(Cl)=C1 DDOXQIODUSXROP-UHFFFAOYSA-N 0.000 claims description 4
- RPHQMRWKOPBZQY-UHFFFAOYSA-N 2-amino-3-(4-chlorophenyl)propan-1-ol Chemical compound OCC(N)CC1=CC=C(Cl)C=C1 RPHQMRWKOPBZQY-UHFFFAOYSA-N 0.000 claims description 3
- CVZZNRXMDCOHBG-UHFFFAOYSA-N 2-azaniumyl-3-(2-chlorophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=CC=C1Cl CVZZNRXMDCOHBG-UHFFFAOYSA-N 0.000 claims description 3
- JJDJLFDGCUYZMN-QMMMGPOBSA-N 3-chloro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(Cl)=C1 JJDJLFDGCUYZMN-QMMMGPOBSA-N 0.000 claims description 3
- YAAHVYMDWVLVEW-UHFFFAOYSA-N 2-amino-3-(2,4-dichlorophenyl)propan-1-ol Chemical compound OCC(N)CC1=CC=C(Cl)C=C1Cl YAAHVYMDWVLVEW-UHFFFAOYSA-N 0.000 claims description 2
- GWHQTNKPTXDNRM-UHFFFAOYSA-N 2-azaniumyl-3-(2,4-dichlorophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1Cl GWHQTNKPTXDNRM-UHFFFAOYSA-N 0.000 claims description 2
- LWFYNRYRKMEIIJ-UHFFFAOYSA-N 2-azaniumyl-3-(2,6-dichlorophenyl)propanoate Chemical compound OC(=O)C(N)CC1=C(Cl)C=CC=C1Cl LWFYNRYRKMEIIJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- FCLCQOSGWAJGBJ-VIFPVBQESA-N methyl (2s)-2-amino-3-(3,4-dichlorophenyl)propanoate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(Cl)C(Cl)=C1 FCLCQOSGWAJGBJ-VIFPVBQESA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 230000001131 transforming effect Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 2
- 125000004188 dichlorophenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000001539 anorectic effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- YPBXFEZZIARTHS-UHFFFAOYSA-N 1-(2,4-dichlorophenoxy)propan-1-ol Chemical compound CCC(O)OC1=CC=C(Cl)C=C1Cl YPBXFEZZIARTHS-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- NIGWMJHCCYYCSF-UHFFFAOYSA-N Fenclonine Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1 NIGWMJHCCYYCSF-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
- 206010023644 Lacrimation increased Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- VSZLVRSHQJSDSG-VIFPVBQESA-N methyl (2s)-2-amino-3-(2,4-dichlorophenyl)propanoate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(Cl)C=C1Cl VSZLVRSHQJSDSG-VIFPVBQESA-N 0.000 description 1
- NOTFEHXAVUQWDQ-FVGYRXGTSA-N methyl (2s)-2-amino-3-(3,4-dichlorophenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)[C@@H](N)CC1=CC=C(Cl)C(Cl)=C1 NOTFEHXAVUQWDQ-FVGYRXGTSA-N 0.000 description 1
- FBHPVOLRIXZZMD-UHFFFAOYSA-N methyl 2-amino-3-(4-chlorophenyl)propanoate Chemical compound COC(=O)C(N)CC1=CC=C(Cl)C=C1 FBHPVOLRIXZZMD-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000001107 psychogenic effect Effects 0.000 description 1
- 230000001003 psychopharmacologic effect Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
Landscapes
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH231671A CH550136A (de) | 1971-02-17 | 1971-02-17 | Verfahren zur herstellung neuer phenylpropanolamine. |
| CH1861771A CH565136A5 (en) | 1971-12-21 | 1971-12-21 | 2-amino-3-(halo phenyl) - propanols - as anorexic agents and anti depressants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83310B1 true PL83310B1 (en) | 1975-12-31 |
Family
ID=25690113
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL15350272A PL83310B1 (en) | 1971-02-17 | 1972-02-15 | Aminopropanol derivatives[gb1377787a] |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE779402A (ref) |
| DE (1) | DE2206961A1 (ref) |
| ES (1) | ES399820A1 (ref) |
| FR (1) | FR2125484B1 (ref) |
| GB (1) | GB1377787A (ref) |
| HU (1) | HU163932B (ref) |
| NL (1) | NL7201809A (ref) |
| PL (1) | PL83310B1 (ref) |
| SU (1) | SU510146A3 (ref) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4788010A (en) * | 1985-04-24 | 1988-11-29 | E. R. Squibb & Sons, Inc. | Amino substituted benzenepropanols |
| FR2593499B1 (fr) * | 1986-01-30 | 1988-08-12 | Jouveinal Sa | Aminoalcools, leur procede de preparation et leurs applications, notamment en therapeutique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3062839A (en) * | 1959-06-11 | 1962-11-06 | American Home Prod | Dihydroxy-tertiary-butylamines |
-
1972
- 1972-02-05 ES ES399820A patent/ES399820A1/es not_active Expired
- 1972-02-11 NL NL7201809A patent/NL7201809A/xx unknown
- 1972-02-14 DE DE19722206961 patent/DE2206961A1/de active Pending
- 1972-02-15 HU HUSA002314 patent/HU163932B/hu unknown
- 1972-02-15 FR FR7205050A patent/FR2125484B1/fr not_active Expired
- 1972-02-15 GB GB692572A patent/GB1377787A/en not_active Expired
- 1972-02-15 BE BE779402A patent/BE779402A/xx unknown
- 1972-02-15 PL PL15350272A patent/PL83310B1/pl unknown
- 1972-02-16 SU SU1749281A patent/SU510146A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| FR2125484A1 (ref) | 1972-09-29 |
| DE2206961A1 (de) | 1972-08-31 |
| SU510146A3 (ru) | 1976-04-05 |
| BE779402A (fr) | 1972-08-16 |
| FR2125484B1 (ref) | 1975-04-25 |
| NL7201809A (ref) | 1972-08-21 |
| HU163932B (ref) | 1973-11-28 |
| ES399820A1 (es) | 1975-07-01 |
| GB1377787A (en) | 1974-12-18 |
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