CA1338445C - 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents - Google Patents

1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents

Info

Publication number
CA1338445C
CA1338445C CA000540932A CA540932A CA1338445C CA 1338445 C CA1338445 C CA 1338445C CA 000540932 A CA000540932 A CA 000540932A CA 540932 A CA540932 A CA 540932A CA 1338445 C CA1338445 C CA 1338445C
Authority
CA
Canada
Prior art keywords
amino
hydrocarbyl
hydroxy
independently
halogen
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 - Fee Related
Application number
CA000540932A
Other languages
English (en)
French (fr)
Inventor
William W. Lee
J. Martin Brown
Edward W. Grange
Abelardo P. Martinez
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.)
SRI International Inc
Original Assignee
SRI International Inc
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 SRI International Inc filed Critical SRI International Inc
Application granted granted Critical
Publication of CA1338445C publication Critical patent/CA1338445C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
    • C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
    • A61K41/0038—Radiosensitizing, i.e. administration of pharmaceutical agents that enhance the effect of radiotherapy
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
CA000540932A 1986-09-25 1987-06-30 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents Expired - Fee Related CA1338445C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US91190686A 1986-09-25 1986-09-25
US911,906 1986-09-25

Publications (1)

Publication Number Publication Date
CA1338445C true CA1338445C (en) 1996-07-09

Family

ID=25431084

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000540932A Expired - Fee Related CA1338445C (en) 1986-09-25 1987-06-30 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents

Country Status (5)

Country Link
JP (1) JP2668232B2 (enExample)
CA (1) CA1338445C (enExample)
DE (2) DE3790581B4 (enExample)
GB (1) GB2203151B (enExample)
WO (1) WO1988002366A1 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5175287A (en) * 1986-09-25 1992-12-29 S R I International Process for preparing 1,2,4-benzotriazine oxides
US5616584A (en) 1986-09-25 1997-04-01 Sri International 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents
IE62911B1 (en) * 1988-03-18 1995-03-08 Stanford Res Inst Int 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents
GR1000941B (el) * 1989-03-17 1993-03-16 Stanford Res Inst Int Μεθοδος παρασκευης οξειδιων 1,2,4,βενζοτριαζινης.
EP0478545B1 (en) * 1989-09-18 1999-08-11 Sri International 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents
US5672702A (en) * 1995-12-04 1997-09-30 Sanofi Process for preparing 3 amino 1, 2, 4-benzotriazine dioxide
JP2015500295A (ja) * 2011-12-07 2015-01-05 エスアールアイ インターナショナルＳＲＩ Ｉｎｔｅｒｎａｔｉｏｎａｌ ヒト結核菌を標的とする医薬としてのベンゾトリアジンオキサイド類
US10981953B2 (en) 2013-12-26 2021-04-20 Toagosei Co, Ltd. Method for promoting expression of calreticulin, and synthetic peptide for use in method for promoting expression of calreticulin
JP6872713B2 (ja) 2015-05-29 2021-05-19 東亞合成株式会社 腫瘍細胞の放射線感受性を増大させる合成ペプチド及びその利用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2489352A (en) * 1946-04-10 1949-11-29 Merck & Co Inc Halogen compounds of 3 aminobenzotriazine 1, 2, 4 oxide-1
US2489359A (en) * 1947-01-10 1949-11-29 Merck & Co Inc Benzotriazines
CH487171A (de) * 1963-10-22 1970-03-15 Siegfried Ag Verfahren zur Herstellung therapeutisch wirksamer 1,2-Dihydro-1,2,4-benztriazine
DE1809390A1 (de) * 1968-11-16 1970-06-11 Bayer Ag Phosphor-,Phosphon- bzw.Thionophosphor-(-phosphon)-saeureester und Verfahren zu ihrer Herstellung
IE38778B1 (en) * 1973-02-02 1978-05-24 Ciba Geigy New 1,2,4-benzotriazine derivatives
DE2538179C2 (de) * 1975-08-27 1986-05-28 Bayer Ag, 5090 Leverkusen 3-Alkoxy-benzo-1,2,4-triazine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DE2740887A1 (de) * 1977-09-10 1979-03-22 Bayer Ag Mittel zur bekaempfung von pflanzenbakteriosen

Also Published As

Publication number Publication date
JP2668232B2 (ja) 1997-10-27
JPH01500826A (ja) 1989-03-23
WO1988002366A1 (en) 1988-04-07
GB8810634D0 (en) 1988-07-06
DE3790581T1 (enExample) 1988-08-25
GB2203151B (en) 1991-05-29
DE3790581B4 (de) 2004-12-23
GB2203151A (en) 1988-10-12

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Legal Events

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