GB2203151A - 1,2,4, benzotriazine oxides as radio sensitizers and selective cytotoxic agents - Google Patents

1,2,4, benzotriazine oxides as radio sensitizers and selective cytotoxic agents

Info

Publication number
GB2203151A
GB2203151A GB08810634A GB8810634A GB2203151A GB 2203151 A GB2203151 A GB 2203151A GB 08810634 A GB08810634 A GB 08810634A GB 8810634 A GB8810634 A GB 8810634A GB 2203151 A GB2203151 A GB 2203151A
Authority
GB
United Kingdom
Prior art keywords
hydrocarbyl
independently
nhr
alkoxy
hydroxy
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.)
Granted
Application number
GB08810634A
Other versions
GB2203151B (en
GB8810634D0 (en
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
Stanford Research Institute
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 Stanford Research Institute filed Critical Stanford Research Institute
Publication of GB8810634D0 publication Critical patent/GB8810634D0/en
Publication of GB2203151A publication Critical patent/GB2203151A/en
Application granted granted Critical
Publication of GB2203151B publication Critical patent/GB2203151B/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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)

Abstract

Compounds of formula (I), wherein when X is OH, OR or NR2, n is 0 or 1, and when X is NH2 or NHR, n is 0, where each R is independently an alkyl of 1-4 carbon atoms or a morpholino moiety and may further be substituted with hydroxy, alkoxy, amino or halogeno substituents, Y<1> and Y<2> are independently either H, halogeno, hydrocarbyl (1-14C) including cyclic and unsaturated hydrocarbyl, optionally substituted with 1 or 2 substituents selected from the group consisting of halogeno, hydroxy, epoxy, alkoxy, alkylthio, amino (including morpholino), acyloxy, acylamido and their thio analogs, carboxy, alkoxycarbonyl, carbamyl or alkylcarbamyl, and wherein the hydrocarbyl can optionally be interrupted by a single ether (-O-) linkage, or wherein Y<1> or Y<2> are independently either NHR', O(CO)R', NH(CO)R', O(SO)R', or O(POR')R' in which R' is a hydrocarbyl optionally substituted as defined above; and wherein when X is NH2 and n is 1, Y<1> and Y<2> are independently either H, saturated or unsaturated hydrocarbyl of between about 7 and 14 carbon atoms, unsaturated hydrocarbyl of betweeen about 1 and 6 carbon atoms, either hydrocarbyl substituents being unsubstituted or substituted with halogen, hydroxy, epoxy, alkoxy, alkylthio, amino, morpholino, acyloxy, acylamide and their thio analogs, and where the hydrocarbyl can be optionally interrupted by a single ether linkage, or wherein Y<1> or Y<2> are independently either NHR', O(CO)R', NH(CO)R', O(SO)R', or O(POR)R', in which R' is a hydrocarbyl optionally substituted as defined above. Compounds within the purview of the formula and related compounds are useful in killing hypoxic tumor cells and as radiosensitizing agents.
GB8810634A 1986-09-25 1987-06-16 1,2,4-benzotriazine oxides as radiosensitisers and selective cytotoxic agents Expired - Lifetime GB2203151B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US91190686A 1986-09-25 1986-09-25
PCT/US1987/001412 WO1988002366A1 (en) 1986-09-25 1987-06-16 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents

Publications (3)

Publication Number Publication Date
GB8810634D0 GB8810634D0 (en) 1988-07-06
GB2203151A true GB2203151A (en) 1988-10-12
GB2203151B GB2203151B (en) 1991-05-29

Family

ID=25431084

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8810634A Expired - Lifetime GB2203151B (en) 1986-09-25 1987-06-16 1,2,4-benzotriazine oxides as radiosensitisers and selective cytotoxic agents

Country Status (5)

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

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
US5624925A (en) 1986-09-25 1997-04-29 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 (en) * 1989-03-17 1993-03-16 Stanford Res Inst Int Method for preparing 1,2,4-benzotriazine oxides
ATE183094T1 (en) * 1989-09-18 1999-08-15 Stanford Res Inst Int 1,2,4-BENZOTRIAZINE OXIDES AS RADIO-SENSITIVE AND SELECTIVE CYTOTOXIC AGENTS
US5672702A (en) * 1995-12-04 1997-09-30 Sanofi Process for preparing 3 amino 1, 2, 4-benzotriazine dioxide
JP2015500295A (en) * 2011-12-07 2015-01-05 エスアールアイ インターナショナルＳＲＩ Ｉｎｔｅｒｎａｔｉｏｎａｌ Benzotriazine oxides as drugs targeting Mycobacterium tuberculosis
JP6654899B2 (en) 2013-12-26 2020-02-26 東亞合成株式会社 Method for promoting calreticulin expression and synthetic peptide used in the method
JP6872713B2 (en) 2015-05-29 2021-05-19 東亞合成株式会社 Synthetic peptides that increase the radiosensitivity of tumor cells and their use

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 (en) * 1963-10-22 1970-03-15 Siegfried Ag Process for the preparation of therapeutically active 1,2-dihydro-1,2,4-benzotriazines
DE1809390A1 (en) * 1968-11-16 1970-06-11 Bayer Ag Phosphorus, phosphonic or thionophosphorus (- phosphonic) acid esters and process for their production
IL44058A (en) * 1973-02-02 1978-10-31 Ciba Geigy Ag 3amino-1,2,4-benzotriazine 1,4-di-noxide derivatives, their preparation and compositions for the control of microorganisms containing them
DE2538179C2 (en) * 1975-08-27 1986-05-28 Bayer Ag, 5090 Leverkusen 3-alkoxy-benzo-1,2,4-triazines, process for their preparation and their use as fungicides
DE2740887A1 (en) * 1977-09-10 1979-03-22 Bayer Ag AGENTS FOR CONTROLLING PLANT BACTERIOS

Also Published As

Publication number Publication date
JP2668232B2 (en) 1997-10-27
CA1338445C (en) 1996-07-09
GB2203151B (en) 1991-05-29
JPH01500826A (en) 1989-03-23
WO1988002366A1 (en) 1988-04-07
GB8810634D0 (en) 1988-07-06
DE3790581B4 (en) 2004-12-23
DE3790581T1 (en) 1988-08-25

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Legal Events

Date Code Title Description
PE20 Patent expired after termination of 20 years

Effective date: 20070615