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 thereof

Info

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
Application number
GB143372A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Asta Medica GmbH
Original Assignee
Asta Werke AG Chemische Fabrik
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Asta Werke AG Chemische Fabrik filed Critical Asta Werke AG Chemische Fabrik
Publication of GB1377231A publication Critical patent/GB1377231A/en
Expired legal-status Critical Current

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.
GB143372A 1971-01-22 1972-01-12 Basically substituted benzyl-phthalazinone derivatives acid addition salts thereof and process for the production thereof Expired GB1377231A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174464B1 (en) * 1984-09-14 1990-01-03 ASTA Pharma AG Substituted benzyl phthalazinone derivatives
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
EP0316639B1 (en) * 1987-11-13 1994-06-08 ASTA Medica Aktiengesellschaft Azelastin embonate, process for its preparation and pharmaceutical compositions containing azelastin embonate as the active ingredient
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
EP2007735B1 (en) * 2006-04-20 2010-10-27 Glaxo Group Limited 2-substituted 4-benzylphthalazinone derivatives as histamine h1 and h3 antagonists

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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.

Cited By (7)

* Cited by examiner, † Cited by third party
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
AR197293A1 (en) 1974-03-29
FI53704B (en) 1978-03-31
ES398949A1 (en) 1975-06-01
DK136981B (en) 1977-12-27
FR2122517B1 (en) 1975-08-01
HK62577A (en) 1977-12-30
DE2164058B2 (en) 1980-10-23
YU11272A (en) 1980-06-30
PL88930B1 (en) 1976-10-30
DE2164058C3 (en) 1981-08-13
SE404604B (en) 1978-10-16
HU163979B (en) 1973-12-28
DK136981C (en) 1978-06-05
CH572914A5 (en) 1976-02-27
AU3767472A (en) 1973-07-12
IL38496A0 (en) 1972-03-28
FI53704C (en) 1978-07-10
ZA718712B (en) 1972-09-27
DE2164058A1 (en) 1972-07-27
FR2122517A1 (en) 1972-09-01
NL177116C (en) 1985-08-01
BE778269A (en) 1972-07-19
CA1010041A (en) 1977-05-10
OA04087A (en) 1979-10-30
SU440838A3 (en) 1974-08-25
IL38496A (en) 1975-05-22
NL7200400A (en) 1972-07-25
YU35361B (en) 1980-12-31
AT313288B (en) 1974-02-11
NL177116B (en) 1985-03-01

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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