IL31570A - Laevorotatory indole derivatives,their production and pharmaceutical compositions containing them - Google Patents
Laevorotatory indole derivatives,their production and pharmaceutical compositions containing themInfo
- Publication number
- IL31570A IL31570A IL31570A IL3157069A IL31570A IL 31570 A IL31570 A IL 31570A IL 31570 A IL31570 A IL 31570A IL 3157069 A IL3157069 A IL 3157069A IL 31570 A IL31570 A IL 31570A
- Authority
- IL
- Israel
- Prior art keywords
- laevorotatory
- formula
- hydroxy
- indole
- methylindole
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 239000008194 pharmaceutical composition Substances 0.000 title claims 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- JHFAEUICJHBVHB-UHFFFAOYSA-N 1h-indol-2-ol Chemical compound C1=CC=C2NC(O)=CC2=C1 JHFAEUICJHBVHB-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- -1 alkali metal amide Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 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
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229940102884 adrenalin Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000001660 hyperkinetic effect Effects 0.000 description 1
- 230000001969 hypertrophic effect Effects 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000213 tachycardiac effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH198768A CH495983A (de) | 1968-02-09 | 1968-02-09 | Verfahren zur Herstellung von linksdrehendem 4-(2-Hydroxy-3-isopropylaminopropoxy)indol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31570A0 IL31570A0 (en) | 1969-11-12 |
| IL31570A true IL31570A (en) | 1972-03-28 |
Family
ID=4223253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31570A IL31570A (en) | 1968-02-09 | 1969-02-07 | Laevorotatory indole derivatives,their production and pharmaceutical compositions containing them |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT299188B (fr) |
| BE (1) | BE728142A (fr) |
| BR (1) | BR6906200D0 (fr) |
| CH (1) | CH495983A (fr) |
| DE (1) | DE1905881C2 (fr) |
| DK (1) | DK119110B (fr) |
| FI (1) | FI50972C (fr) |
| FR (2) | FR1598040A (fr) |
| GB (2) | GB1251716A (fr) |
| IE (1) | IE32639B1 (fr) |
| IL (1) | IL31570A (fr) |
| NL (1) | NL6900797A (fr) |
| NO (1) | NO125590B (fr) |
| SE (1) | SE340621B (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4182911A (en) | 1973-11-09 | 1980-01-08 | Imperial Chemical Industries Limited | Optically-active 1-aryloxy-2-propanol intermediates of (S)-absolute configuration |
| DE2454198C2 (de) * | 1974-11-15 | 1986-08-07 | Knoll Ag, 6700 Ludwigshafen | Isochinolin-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel |
| CA1116598A (fr) * | 1977-07-13 | 1982-01-19 | William T. Comer | 3-indolyl-butylaminopropanols tertiaires |
| DE2905053A1 (de) * | 1979-02-08 | 1980-08-14 | Schering Ag | Verfahren zur herstellung von 1-(2-methylindol-4-yloxy)-2.3-epoxypropan |
| DE3029980A1 (de) * | 1980-08-08 | 1982-03-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | Indolderivate und verfahren zu ihrer herstellung |
| DE3030047A1 (de) * | 1980-08-08 | 1982-03-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1129072A (en) * | 1966-02-01 | 1968-10-02 | Ici Ltd | Benzofuran and indole derivatives |
| NL131726C (fr) * | 1965-02-01 |
-
1968
- 1968-02-09 CH CH198768A patent/CH495983A/de not_active IP Right Cessation
- 1968-12-23 FR FR1598040D patent/FR1598040A/fr not_active Expired
-
1969
- 1969-01-13 GB GB1251716D patent/GB1251716A/en not_active Expired
- 1969-01-13 GB GB1252399D patent/GB1252399A/en not_active Expired
- 1969-01-17 SE SE00616/69A patent/SE340621B/xx unknown
- 1969-01-17 NL NL6900797A patent/NL6900797A/xx unknown
- 1969-01-17 DK DK26869AA patent/DK119110B/da unknown
- 1969-01-20 FI FI690158A patent/FI50972C/fi active
- 1969-01-20 NO NO0209/69A patent/NO125590B/no unknown
- 1969-02-06 DE DE1905881A patent/DE1905881C2/de not_active Expired
- 1969-02-06 IE IE156/69A patent/IE32639B1/xx unknown
- 1969-02-07 BR BR206200/69A patent/BR6906200D0/pt unknown
- 1969-02-07 AT AT128169A patent/AT299188B/de not_active IP Right Cessation
- 1969-02-07 IL IL31570A patent/IL31570A/en unknown
- 1969-02-07 BE BE728142D patent/BE728142A/xx not_active IP Right Cessation
- 1969-03-18 FR FR183290A patent/FR8067M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1905881A1 (de) | 1969-09-25 |
| GB1251716A (fr) | 1971-10-27 |
| FR8067M (fr) | 1970-07-06 |
| FR1598040A (fr) | 1970-06-29 |
| DK119110B (da) | 1970-11-16 |
| GB1252399A (fr) | 1971-11-03 |
| IE32639B1 (en) | 1973-10-17 |
| NO125590B (fr) | 1972-10-02 |
| FI50972B (fr) | 1976-05-31 |
| AT299188B (de) | 1972-06-12 |
| BE728142A (fr) | 1969-08-07 |
| FI50972C (fi) | 1976-09-10 |
| SE340621B (fr) | 1971-11-29 |
| BR6906200D0 (pt) | 1973-02-27 |
| CH495983A (de) | 1970-09-15 |
| DE1905881C2 (de) | 1984-03-08 |
| IL31570A0 (en) | 1969-11-12 |
| NL6900797A (fr) | 1969-08-12 |
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