GB1306511A - Imidazoline derivatives - Google Patents
Imidazoline derivativesInfo
- Publication number
- GB1306511A GB1306511A GB868870A GB868870A GB1306511A GB 1306511 A GB1306511 A GB 1306511A GB 868870 A GB868870 A GB 868870A GB 868870 A GB868870 A GB 868870A GB 1306511 A GB1306511 A GB 1306511A
- Authority
- GB
- United Kingdom
- Prior art keywords
- free base
- acid addition
- resulting
- general formula
- formula
- 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
- 150000002462 imidazolines Chemical class 0.000 title abstract 4
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 239000012458 free base Substances 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 239000002269 analeptic agent Substances 0.000 abstract 1
- 239000002830 appetite depressant Substances 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- NVZLBPXTJTXPDC-UHFFFAOYSA-N pyrrolo[3,4-e]benzimidazole Chemical class C1=CC2=NC=NC2=C2C=NC=C21 NVZLBPXTJTXPDC-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Indole Compounds (AREA)
Abstract
1306511 Imidazoline derivatives SANDOZ Ltd 23 Feb 1970 [5 March 1969 19 May 1969 9 Oct 1969] 8688/70 Heading C2C Novel imidazoline derivatives of the general formula wherein R and R 1 are each a hydrogen, fluorine or chlorine atom and R 3 is a hydrogen atom or a phenyl group, and acid addition salts thereof are prepared by reaction of an organolithium compound of the formula with a carbonyl compound of the general formula followed by hydrolysis, and optional salification of a resulting free base or conversion of a resulting salt to the corresponding free base. Imidazoisoindole derivatives of the general formula and acid addition salts thereof, are prepared by treatment of an imidazoline derivative of the first formula above wherein R 3 is a hydrogen atom or an acid addition salt thereof with a catalytic amount of an acid, followed by mild oxidation and optionally by salification of a resulting free base or conversion of a resulting salt to the corresponding free base. Pharmaceutical compositions having central nervous system stimulant and appetite-depressant activity comprise, as active ingredient, an imdiazoline derivative of the first formula above wherein R 3 is a phenyl group or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier, and may be administered orally or parenterally. Reference has been directed by the Comptroller to Specification 1,187,009.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81294869A | 1969-03-05 | 1969-03-05 | |
US82595469A | 1969-05-19 | 1969-05-19 | |
US86517969A | 1969-10-09 | 1969-10-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1306511A true GB1306511A (en) | 1973-02-14 |
Family
ID=27420085
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3670170A Expired GB1306512A (en) | 1969-03-05 | 1970-02-23 | Organolithium derivative and its use in producing imidazoisoindoles |
GB868870A Expired GB1306511A (en) | 1969-03-05 | 1970-02-23 | Imidazoline derivatives |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3670170A Expired GB1306512A (en) | 1969-03-05 | 1970-02-23 | Organolithium derivative and its use in producing imidazoisoindoles |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS4843120B1 (en) |
CA (1) | CA939355A (en) |
CH (2) | CH530980A (en) |
DE (1) | DE2009780C2 (en) |
ES (3) | ES377089A1 (en) |
FR (2) | FR2034663B1 (en) |
GB (2) | GB1306512A (en) |
SE (2) | SE365218B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5039814A (en) * | 1990-05-02 | 1991-08-13 | Merck & Co., Inc. | Ortho-lithiation process for the synthesis of 2-substituted 1-(tetrazol-5-yl)benzenes |
US5310928A (en) * | 1991-11-18 | 1994-05-10 | E. I. Du Pont De Nemours And Company | Process for preparing biphenyltetrazole compounds |
US5206374A (en) * | 1991-11-18 | 1993-04-27 | E. I. Du Pont De Nemours And Company | Process for preparing tetrazolylphenylboronic acid intermediates |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL6803799A (en) * | 1967-03-23 | 1968-09-24 | ||
US3888846A (en) * | 1967-03-30 | 1975-06-10 | Hoffmann La Roche | Process for 2(2-(1,3-diazacycloalk-2-enyl))benzophenone derivatives and 1,3-diazacycloalkenyl(2,1-a)isoindole derivatives |
US3717658A (en) * | 1968-03-07 | 1973-02-20 | Hoffmann La Roche | 3'-arylspiro(imidazolidine-2,1'-phthalan)and 2-(2'-(alpha-hydroxy-arylmethyl)-aryl)-2-imidazoline derivatives |
-
1970
- 1970-02-20 CH CH246370A patent/CH530980A/en not_active IP Right Cessation
- 1970-02-20 CH CH1572572A patent/CH531511A/en not_active IP Right Cessation
- 1970-02-23 GB GB3670170A patent/GB1306512A/en not_active Expired
- 1970-02-23 GB GB868870A patent/GB1306511A/en not_active Expired
- 1970-03-03 CA CA076,316A patent/CA939355A/en not_active Expired
- 1970-03-03 ES ES377089A patent/ES377089A1/en not_active Expired
- 1970-03-03 DE DE19702009780 patent/DE2009780C2/en not_active Expired
- 1970-03-03 FR FR7007512A patent/FR2034663B1/fr not_active Expired
- 1970-03-03 JP JP1773070A patent/JPS4843120B1/ja active Pending
- 1970-03-04 SE SE285770A patent/SE365218B/xx unknown
-
1971
- 1971-06-30 FR FR7123908A patent/FR2100576B1/fr not_active Expired
-
1972
- 1972-04-26 ES ES402117A patent/ES402117A1/en not_active Expired
- 1972-04-26 ES ES402115A patent/ES402115A1/en not_active Expired
-
1973
- 1973-09-14 SE SE7312550A patent/SE405249B/en unknown
Also Published As
Publication number | Publication date |
---|---|
ES402117A1 (en) | 1975-11-01 |
CA939355A (en) | 1974-01-01 |
FR2034663B1 (en) | 1974-08-30 |
CH530980A (en) | 1972-11-30 |
FR2100576A1 (en) | 1972-03-24 |
JPS4843120B1 (en) | 1973-12-17 |
FR2100576B1 (en) | 1975-06-06 |
FR2034663A1 (en) | 1970-12-11 |
CH531511A (en) | 1972-12-15 |
ES377089A1 (en) | 1972-12-16 |
ES402115A1 (en) | 1975-11-01 |
DE2009780C2 (en) | 1983-11-24 |
SE405249B (en) | 1978-11-27 |
GB1306512A (en) | 1973-02-14 |
DE2009780A1 (en) | 1972-02-17 |
SE365218B (en) | 1974-03-18 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PLNP | Patent lapsed through nonpayment of renewal fees |