GB1252399A - - Google Patents
Info
- Publication number
- GB1252399A GB1252399A GB1252399DA GB1252399A GB 1252399 A GB1252399 A GB 1252399A GB 1252399D A GB1252399D A GB 1252399DA GB 1252399 A GB1252399 A GB 1252399A
- Authority
- GB
- United Kingdom
- Prior art keywords
- laevorotatory
- compound
- acid addition
- benzyl
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 abstract 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- CTWQPSSVUYPWOM-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1CO1 CTWQPSSVUYPWOM-UHFFFAOYSA-N 0.000 abstract 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 239000003087 receptor blocking agent Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 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)
Abstract
1,252,399. Indole-derived hydroxyamine. SANDOZ Ltd. 13 Jan., 1969 [9 Feb., 1968], No. 5985/71. Divided out of 1,251,716. Addition to 1,138,969. Heading C2C. The invention comprises the laevorotatory compound of formula and its acid addition salts. This compound is prepared by reacting 4-hydroxyindole in an alkaline medium and in absence of O 2 , with laevorotatory epichlorohydrin or bromohydrin, heating the reaction product (presumably optically active 4-glycidyloxyindole) with (R being H or benzyl), splitting off any benzyl radical if present, and optionally converting the product to an acid addition salt by reaction with an inorganic or organic acid. Therapeutic compositions comprise the compounds of the above formula, which is a #- receptor blocker, and may be used in the form of tablets, dragees, suppositories or injectable solutions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH198768A CH495983A (en) | 1968-02-09 | 1968-02-09 | Process for the preparation of levorotatory 4- (2-hydroxy-3-isopropylaminopropoxy) indole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1252399A true GB1252399A (en) | 1971-11-03 |
Family
ID=4223253
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1252399D Expired GB1252399A (en) | 1968-02-09 | 1969-01-13 | |
| GB1251716D Expired GB1251716A (en) | 1968-02-09 | 1969-01-13 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1251716D Expired GB1251716A (en) | 1968-02-09 | 1969-01-13 |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT299188B (en) |
| BE (1) | BE728142A (en) |
| BR (1) | BR6906200D0 (en) |
| CH (1) | CH495983A (en) |
| DE (1) | DE1905881C2 (en) |
| DK (1) | DK119110B (en) |
| FI (1) | FI50972C (en) |
| FR (2) | FR1598040A (en) |
| GB (2) | GB1252399A (en) |
| IE (1) | IE32639B1 (en) |
| IL (1) | IL31570A (en) |
| NL (1) | NL6900797A (en) |
| NO (1) | NO125590B (en) |
| SE (1) | SE340621B (en) |
Cited By (1)
| 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 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2454198C2 (en) * | 1974-11-15 | 1986-08-07 | Knoll Ag, 6700 Ludwigshafen | Isoquinoline derivatives, processes for their preparation and medicines |
| CA1116598A (en) * | 1977-07-13 | 1982-01-19 | William T. Comer | 3-indolyl-tertiary butylaminopropanols |
| DE2905053A1 (en) * | 1979-02-08 | 1980-08-14 | Schering Ag | 1-Methyl:indolyl:oxy-2,3-epoxy-propane prodn. - from 4-hydroxy-2-methyl:indole and epichlorohydrin in protic solvent |
| DE3030047A1 (en) * | 1980-08-08 | 1982-03-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | NEW AMINOPROPANOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| DE3029980A1 (en) * | 1980-08-08 | 1982-03-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | INDOLDER DERIVATIVES AND METHOD FOR THEIR PRODUCTION |
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 (en) * | 1965-02-01 |
-
1968
- 1968-02-09 CH CH198768A patent/CH495983A/en not_active IP Right Cessation
- 1968-12-23 FR FR1598040D patent/FR1598040A/fr not_active Expired
-
1969
- 1969-01-13 GB GB1252399D patent/GB1252399A/en not_active Expired
- 1969-01-13 GB GB1251716D patent/GB1251716A/en not_active Expired
- 1969-01-17 SE SE00616/69A patent/SE340621B/xx unknown
- 1969-01-17 DK DK26869AA patent/DK119110B/en unknown
- 1969-01-17 NL NL6900797A patent/NL6900797A/xx unknown
- 1969-01-20 FI FI690158A patent/FI50972C/en active
- 1969-01-20 NO NO0209/69A patent/NO125590B/no unknown
- 1969-02-06 DE DE1905881A patent/DE1905881C2/en not_active Expired
- 1969-02-06 IE IE156/69A patent/IE32639B1/en unknown
- 1969-02-07 AT AT128169A patent/AT299188B/en not_active IP Right Cessation
- 1969-02-07 IL IL31570A patent/IL31570A/en unknown
- 1969-02-07 BR BR206200/69A patent/BR6906200D0/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
Cited By (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| AT299188B (en) | 1972-06-12 |
| CH495983A (en) | 1970-09-15 |
| FR8067M (en) | 1970-07-06 |
| DE1905881C2 (en) | 1984-03-08 |
| IL31570A (en) | 1972-03-28 |
| BE728142A (en) | 1969-08-07 |
| NL6900797A (en) | 1969-08-12 |
| FR1598040A (en) | 1970-06-29 |
| IE32639B1 (en) | 1973-10-17 |
| FI50972C (en) | 1976-09-10 |
| FI50972B (en) | 1976-05-31 |
| NO125590B (en) | 1972-10-02 |
| SE340621B (en) | 1971-11-29 |
| BR6906200D0 (en) | 1973-02-27 |
| GB1251716A (en) | 1971-10-27 |
| DE1905881A1 (en) | 1969-09-25 |
| DK119110B (en) | 1970-11-16 |
| IL31570A0 (en) | 1969-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE | Patent expired |