GB1377231A - Basically substituted benzyl-phthalazinone derivatives acid addition salts thereof and process for the production thereof - Google Patents
Basically substituted benzyl-phthalazinone derivatives acid addition salts thereof and process for the production thereofInfo
- Publication number
- GB1377231A GB1377231A GB143372A GB143372A GB1377231A GB 1377231 A GB1377231 A GB 1377231A GB 143372 A GB143372 A GB 143372A GB 143372 A GB143372 A GB 143372A GB 1377231 A GB1377231 A GB 1377231A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- general formula
- alkyl
- phthalazinone
- benzyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1377231 4 - Benzyl - 1(2H) - phthalazinones ASTA-WERKE AG CHEMISCHE FABRIK 12 Jan 1972 [22 Jan 1971] 1433/72 Heading C2C Novel 4 - benzyl - 1(2H) - phthalazinones of the general formula wherein each of R 1 and R 2 is a hydrogen or halogen atom or a C 1-4 alkyl, C 1-4 alkoxy, hydroxy, trifluoromethyl, nitro or optionally substituted amino group; X is -CH 2 - or -CH(CH 3 )-, m and n are each 1, 2 or 3, p is 0 or 1 and -CH=Y is an N-C 1-4 alkyl-pyrrolidinyl, N-C 1-4 alkyl-piperidyl, N-C 1-4 alkyl. perhydroazepinyl, quinuclidinyl, tropanyl or scopyl group, the tropanyl or scopyl group being connected to the 2-nitrogen atom of the phthalazinone directly by way of a ring carbon atom of this tropanyl or scopyl group, and the other groups being connected to the 2-nitrogen atom of the phthalazinone directly or by way of a -CH 2 - or -CH(CH 3 )- group, and physiologically acceptable acid addition salts thereof are prepared (a) by reacting an α-phenyl-acetophenone-o-carboxylic acid of the general formula or a reactive derivative thereof with a hydrazine of the general formula H 2 N-NHR 3 , wherein R 3 is a hydrogen atom or group; (b) by reacting an α-phenyl-acetophenone of the general formula with a hydrazine of the general formula wherein R 4 is a C 1-4 alkyl group; (c) by reacting a hydrazide of the general formula with a phenylacetic acid or derivative thereof of the general formula wherein Z is a halogen atom or a hydroxy or alkoxy group; or (d) when -CH=Y is an N-C 1-4 alkyl-pyrrolidinyl, N-C 1-4 alkyl-piperidyl or N-C 1-4 alkyl-perhydroazepinyl group, by alkylating the corresponding compound in which -CH=Y is a pyrrolidinyl, piperidyl or perhydroazepinyl group; and reacting a benzylphthalazinone of the general formula wherein R 3 is a hydrogen atom, resulting from (a), (b) or (c), with a compound of the general formula Q-R 3 , wherein Q is an atom or group which, upon substitution of the amide group, is split off together with its electron doublet, and R 3 is -(X) p -CH=Y, and optionally converting the resulting benzyl-phthalazinone into a physiologically acceptable acid addition salt thereof or optionally converting a resulting salt of a benzyl-phthalazinone into the free base. Pharmaceutical compositions having histaminolytic activity comprise, as active ingredient, a 4-benzyl-1(2H)-phthalazinone of the first general formula above or a physiologically acceptable acid addition salt thereof, together with a suitable carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH101271A CH572914A5 (en) | 1971-01-22 | 1971-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1377231A true GB1377231A (en) | 1974-12-11 |
Family
ID=4200381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB143372A Expired GB1377231A (en) | 1971-01-22 | 1972-01-12 | Basically substituted benzyl-phthalazinone derivatives acid addition salts thereof and process for the production thereof |
Country Status (21)
| Country | Link |
|---|---|
| AR (1) | AR197293A1 (en) |
| AT (1) | AT313288B (en) |
| AU (1) | AU3767472A (en) |
| BE (1) | BE778269A (en) |
| CA (1) | CA1010041A (en) |
| CH (1) | CH572914A5 (en) |
| DE (1) | DE2164058C3 (en) |
| DK (1) | DK136981B (en) |
| ES (1) | ES398949A1 (en) |
| FI (1) | FI53704C (en) |
| FR (1) | FR2122517B1 (en) |
| GB (1) | GB1377231A (en) |
| HK (1) | HK62577A (en) |
| HU (1) | HU163979B (en) |
| IL (1) | IL38496A (en) |
| NL (1) | NL177116C (en) |
| OA (1) | OA04087A (en) |
| PL (1) | PL88930B1 (en) |
| SE (1) | SE404604B (en) |
| YU (1) | YU35361B (en) |
| ZA (1) | ZA718712B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU609210B2 (en) * | 1987-11-13 | 1991-04-26 | Viatris Gmbh & Co. Kg | Azelastine embonate, processes for its preparation and pharmaceutical formulations which contain azelastine embonate as active substance |
| US5164194A (en) * | 1987-11-13 | 1992-11-17 | Asta Pharma Ag | Azelastine containing medicaments |
| US8071073B2 (en) | 2004-11-24 | 2011-12-06 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| US8758816B2 (en) | 2004-11-24 | 2014-06-24 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| US10064817B2 (en) | 2004-11-24 | 2018-09-04 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE49205T1 (en) * | 1984-09-14 | 1990-01-15 | Asta Pharma Ag | SUBSTITUTE BENZYLPHTHALAZINONE DERIVATIVES. |
| DE3850044D1 (en) * | 1987-11-13 | 1994-07-14 | Asta Medica Ag | Azelastine embonate, process for its preparation and pharmaceutical preparations containing azelastine embonate as active ingredient. |
| DE3836579A1 (en) * | 1987-11-13 | 1989-05-24 | Asta Pharma Ag | Azelastine-containing pharmaceutical compositions for use in the nose and/or on the eye |
| DE3912292A1 (en) * | 1988-04-20 | 1989-11-09 | Asta Pharma Ag | Azelastine-containing pharmaceuticals with controlled release of active substance |
| US5110814A (en) * | 1989-01-11 | 1992-05-05 | Asta Pharma Ag | Azelastine and its salts used to combat psoriasis |
| DE4013696A1 (en) * | 1989-05-05 | 1990-11-08 | Asta Pharma Ag | New azelastin salts |
| DE4207234A1 (en) * | 1992-03-07 | 1993-09-09 | Asta Medica Ag | NEW AMINOCARBONIC ACID DERIVATIVES WITH ANTIALLERGIC / ANTIASTHMIC EFFECT AND METHOD FOR THE PRODUCTION THEREOF |
| DE4345224C2 (en) * | 1993-12-18 | 1999-07-01 | Asta Medica Ag | Process for the preparation of acid addition salts of azelastine and flezelastin |
| DE4343409C2 (en) * | 1993-12-18 | 1997-03-20 | Asta Medica Ag | Improved process for the production of hexahydroazepinones and hexahydroazepinols |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| DE602007010118D1 (en) * | 2006-04-20 | 2010-12-09 | Glaxo Group Ltd | 2-SUBSTITUTED 4-BENZYLPHTHALAZINE DERIVATIVES AS HISTAMINE H1 AND H3 ANTAGONISTS |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1046625B (en) * | 1957-08-15 | 1958-12-18 | Hydrierwerk Rodleben Veb | Process for the production of basic substituted phthalazones |
| GB1100911A (en) * | 1963-08-20 | 1968-01-24 | Benger Lab Ltd | Phthalazine derivatives |
| DK119061B (en) * | 1966-10-28 | 1970-11-09 | Hydrierwerk Rodleben Veb | Process for the preparation of basic substituted phthalazones or salts or quaternary ammonium compounds thereof. |
-
1971
- 1971-01-22 CH CH101271A patent/CH572914A5/xx not_active IP Right Cessation
- 1971-12-23 DE DE2164058A patent/DE2164058C3/en not_active Expired
- 1971-12-30 ZA ZA718712A patent/ZA718712B/en unknown
-
1972
- 1972-01-03 IL IL38496A patent/IL38496A/en unknown
- 1972-01-06 AU AU37674/72A patent/AU3767472A/en not_active Expired
- 1972-01-11 NL NLAANVRAGE7200400,A patent/NL177116C/en not_active IP Right Cessation
- 1972-01-12 GB GB143372A patent/GB1377231A/en not_active Expired
- 1972-01-13 AT AT25672A patent/AT313288B/en active
- 1972-01-17 YU YU112/72A patent/YU35361B/en unknown
- 1972-01-18 ES ES398949A patent/ES398949A1/en not_active Expired
- 1972-01-18 CA CA132,681A patent/CA1010041A/en not_active Expired
- 1972-01-19 AR AR240139A patent/AR197293A1/en active
- 1972-01-19 FR FR7201729A patent/FR2122517B1/fr not_active Expired
- 1972-01-20 PL PL1972153002A patent/PL88930B1/pl unknown
- 1972-01-20 BE BE778269A patent/BE778269A/en not_active IP Right Cessation
- 1972-01-21 SE SE7200722A patent/SE404604B/en unknown
- 1972-01-21 DK DK30272AA patent/DK136981B/en unknown
- 1972-01-21 HU HUAA695A patent/HU163979B/hu unknown
- 1972-01-21 FI FI160/72A patent/FI53704C/en active
- 1972-05-15 OA OA54568A patent/OA04087A/en unknown
-
1977
- 1977-12-22 HK HK625/77A patent/HK62577A/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU609210B2 (en) * | 1987-11-13 | 1991-04-26 | Viatris Gmbh & Co. Kg | Azelastine embonate, processes for its preparation and pharmaceutical formulations which contain azelastine embonate as active substance |
| US5164194A (en) * | 1987-11-13 | 1992-11-17 | Asta Pharma Ag | Azelastine containing medicaments |
| US8071073B2 (en) | 2004-11-24 | 2011-12-06 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| US8518919B2 (en) | 2004-11-24 | 2013-08-27 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| US8758816B2 (en) | 2004-11-24 | 2014-06-24 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
| US9919050B2 (en) | 2004-11-24 | 2018-03-20 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine |
| US10064817B2 (en) | 2004-11-24 | 2018-09-04 | Meda Pharmaceuticals Inc. | Compositions comprising azelastine and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AT313288B (en) | 1974-02-11 |
| FR2122517A1 (en) | 1972-09-01 |
| SU440838A3 (en) | 1974-08-25 |
| AR197293A1 (en) | 1974-03-29 |
| HU163979B (en) | 1973-12-28 |
| ZA718712B (en) | 1972-09-27 |
| NL7200400A (en) | 1972-07-25 |
| AU3767472A (en) | 1973-07-12 |
| OA04087A (en) | 1979-10-30 |
| FI53704B (en) | 1978-03-31 |
| DK136981B (en) | 1977-12-27 |
| BE778269A (en) | 1972-07-19 |
| YU35361B (en) | 1980-12-31 |
| DE2164058C3 (en) | 1981-08-13 |
| IL38496A0 (en) | 1972-03-28 |
| CH572914A5 (en) | 1976-02-27 |
| IL38496A (en) | 1975-05-22 |
| HK62577A (en) | 1977-12-30 |
| YU11272A (en) | 1980-06-30 |
| FI53704C (en) | 1978-07-10 |
| PL88930B1 (en) | 1976-10-30 |
| ES398949A1 (en) | 1975-06-01 |
| DE2164058A1 (en) | 1972-07-27 |
| DK136981C (en) | 1978-06-05 |
| NL177116B (en) | 1985-03-01 |
| CA1010041A (en) | 1977-05-10 |
| DE2164058B2 (en) | 1980-10-23 |
| FR2122517B1 (en) | 1975-08-01 |
| SE404604B (en) | 1978-10-16 |
| NL177116C (en) | 1985-08-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |