GB1476684A - Fused-ring benzothiadiazepine and benzo-thiadiazocine deri vatives - Google Patents

Fused-ring benzothiadiazepine and benzo-thiadiazocine deri vatives

Info

Publication number
GB1476684A
GB1476684A GB2952174A GB2952174A GB1476684A GB 1476684 A GB1476684 A GB 1476684A GB 2952174 A GB2952174 A GB 2952174A GB 2952174 A GB2952174 A GB 2952174A GB 1476684 A GB1476684 A GB 1476684A
Authority
GB
United Kingdom
Prior art keywords
bromo
formula
trifluoro
reacting
alkyl
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
GB2952174A
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.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
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 ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Publication of GB1476684A publication Critical patent/GB1476684A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1476684 Pyrimidino - benzothiadiazepines and -benzothiadiazocines and intermediates therefor E R SQUIBB & SONS Inc 3 July 1974 [26 July 1973] 29521/74 Heading C2C Novel pyrimidino benzothiadiazepines and pyrimidino benzothiadiazocines of the Formula I wherein m is 1 or 2, n is 0 or 1, Z is -S- or -SO 2 -, R<SP>11</SP> is a hydrogen atom or a C 1-4 alkyl group, R is a hydrogen, fluorine, chlorine or bromine atom or a C 1-4 alkyl, benzyl, phenyl or monosubstituted phenyl group, the substituent being fluorine, chlorine, bromine, iodine, C 1-4 alkyl, C 1-4 alkoxy or CF 3 , and R<SP>1</SP> is a hydrogen, fluorine, chlorine or bromine atom or a trifluoromethyl, C 1-4 alkyl or di-(C 1-4 alkyl) sulphamoyl group, and salts thereof, provided that when m is 1, R occupies position -4 or -5 of the pyrimidine ring, but when R is halogen it occupies only position-5, and when m is 2 the two Rs occupy the 4- and 5-positions but only one of them can be halogen and it must occupy the 5-position, are obtained by cyclizing compounds of the Formula IV or V in which X is a chlorine or bromine atom. Compounds of the Formula IV above may be obtained by reacting appropriate 2-aminopyrimidines with haloalkyl o-bromo phenyl thioethers of the Formula III Compounds of the Formula V above may be obtained by reacting compounds of the Formula IV with water-miscible alcohols and alkali metal C 1-3 alkoxides. Haloalkyl o-bromophenyl thioethers of the Formula III above in which Z is a sulphur atom, may be obtained by reacting the corresponding o-bromophenyl thiols (obtainable from the corresponding o-bromo anilines) with haloalkane sulphonic acid, sodium salts and halogenating the o-bromophenylthio alkane sulphonic acid sodium salts so produced, or by reacting the o-bromophenyl thiols with dihaloalkanes. 3 - Bromo - 4 - aminobenzotrifluoride may be obtained by brominating p-aminobenzotrifluoride. 2 - Bromo - α,α,α - trifluoro - m - tolyl bromomethyl sulphone may be obtained by acetylating α,α,α - trifluoro m - toluidine to give α,α,α- trifluoroacetotoluidide, further acetylating this to α,α,α - trifluoro - m - N,N - diacetotoluidide, brominating this to 2-bromo-α,α,α-m-N,N-diacetotoluidide, hydrolysing this with hydrochloric acid to give 2-bromo-α,α,α-trifluoro-mtoluidine hydrochloride, converting this via 2- bromo-α,α,α-trifluoro-m-toluene sulphonyl chloride to sodium 2 - bromo - α,α,α - trifluoro - mtoluene sulphonate and reacting this with dibromomethane. Pharmaceutical compositions contain compounds of Formula I as active ingredients.
GB2952174A 1973-07-26 1974-07-03 Fused-ring benzothiadiazepine and benzo-thiadiazocine deri vatives Expired GB1476684A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US382802A US3875162A (en) 1973-07-26 1973-07-26 Certain 6H-pyrimido{8 1,2-c{9 {8 1,3,5{9 benzothiadiaza compounds

Publications (1)

Publication Number Publication Date
GB1476684A true GB1476684A (en) 1977-06-16

Family

ID=23510466

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2952174A Expired GB1476684A (en) 1973-07-26 1974-07-03 Fused-ring benzothiadiazepine and benzo-thiadiazocine deri vatives

Country Status (6)

Country Link
US (1) US3875162A (en)
JP (1) JPS5041892A (en)
CA (1) CA1051429A (en)
DE (1) DE2435382A1 (en)
FR (1) FR2238491B1 (en)
GB (1) GB1476684A (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010091150A1 (en) 2009-02-05 2010-08-12 Immunogen, Inc. Novel benzodiazepine derivatives
WO2012112708A1 (en) 2011-02-15 2012-08-23 Immunogen, Inc. Cytotoxic benzodiazepine derivatives and methods of preparation
WO2014031566A1 (en) 2012-08-22 2014-02-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
WO2016036804A1 (en) 2014-09-03 2016-03-10 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
WO2018195245A1 (en) 2017-04-20 2018-10-25 Immunogen, Inc. Methods of preparing indolinobenzodiazepine derivatives
WO2018195243A1 (en) 2017-04-20 2018-10-25 Immunogen, Inc. Cytotoxic benzodiazepine derivatives and conjugates thereof
WO2019133652A1 (en) 2017-12-28 2019-07-04 Immunogen, Inc. Benzodiazepine derivatives
WO2020205564A1 (en) 2019-03-29 2020-10-08 Immunogen, Inc. Cytotoxic bis-benzodiazepine derivatives and conjugates thereof with cell-binding agents for inhibiting abnormal cell growth or for treating proliferative diseases
EP3778601A1 (en) 2014-09-03 2021-02-17 ImmunoGen, Inc. Cytotoxic benzodiazepine derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3966733A (en) * 1973-07-26 1976-06-29 E. R. Squibb & Sons, Inc. Intermediates for certain benzothiadiazepine and benzothiadiazocine compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH530412A (en) * 1968-07-15 1972-11-15 Ciba Geigy Ag Process for the preparation of (1) benzothieno- (2,3-d) pyrimidines
GB1275804A (en) * 1969-07-03 1972-05-24 Seperic Improvements in or relating to new sulphur containing derivatives of pyrimidine, their preparation and their applications
US3704303A (en) * 1971-03-17 1972-11-28 American Home Prod 6,7,8,9 - tetrahydropyrimido(2,1-b) - benzothiazole-6-carboxylic acid,alkyl esters

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3360879A1 (en) 2009-02-05 2018-08-15 ImmunoGen, Inc. Benzodiazepine derivatives as cytotoxic agents
WO2010091150A1 (en) 2009-02-05 2010-08-12 Immunogen, Inc. Novel benzodiazepine derivatives
EP3100745A1 (en) 2009-02-05 2016-12-07 Immunogen, Inc. Novel benzodiazepine derivatives
WO2012112708A1 (en) 2011-02-15 2012-08-23 Immunogen, Inc. Cytotoxic benzodiazepine derivatives and methods of preparation
WO2012128868A1 (en) 2011-02-15 2012-09-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
EP3666289A1 (en) 2011-02-15 2020-06-17 ImmunoGen, Inc. Cytotoxic benzodiazepine derivatives
EP3053600A1 (en) 2011-02-15 2016-08-10 ImmunoGen, Inc. Cytotoxic benzodiazepine derivatives
WO2014031566A1 (en) 2012-08-22 2014-02-27 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
WO2016036804A1 (en) 2014-09-03 2016-03-10 Immunogen, Inc. Cytotoxic benzodiazepine derivatives
EP3778601A1 (en) 2014-09-03 2021-02-17 ImmunoGen, Inc. Cytotoxic benzodiazepine derivatives
WO2018195245A1 (en) 2017-04-20 2018-10-25 Immunogen, Inc. Methods of preparing indolinobenzodiazepine derivatives
WO2018195243A1 (en) 2017-04-20 2018-10-25 Immunogen, Inc. Cytotoxic benzodiazepine derivatives and conjugates thereof
WO2019133652A1 (en) 2017-12-28 2019-07-04 Immunogen, Inc. Benzodiazepine derivatives
WO2020205564A1 (en) 2019-03-29 2020-10-08 Immunogen, Inc. Cytotoxic bis-benzodiazepine derivatives and conjugates thereof with cell-binding agents for inhibiting abnormal cell growth or for treating proliferative diseases

Also Published As

Publication number Publication date
FR2238491B1 (en) 1978-07-28
JPS5041892A (en) 1975-04-16
DE2435382A1 (en) 1975-02-13
CA1051429A (en) 1979-03-27
US3875162A (en) 1975-04-01
FR2238491A1 (en) 1975-02-21

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee