GB2203151B - 1,2,4-benzotriazine oxides as radiosensitisers and selective cytotoxic agents - Google Patents

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

Info

Publication number
GB2203151B
GB2203151B GB8810634A GB8810634A GB2203151B GB 2203151 B GB2203151 B GB 2203151B GB 8810634 A GB8810634 A GB 8810634A GB 8810634 A GB8810634 A GB 8810634A GB 2203151 B GB2203151 B GB 2203151B
Authority
GB
United Kingdom
Prior art keywords
radiosensitisers
cytotoxic agents
selective cytotoxic
benzotriazine oxides
benzotriazine
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 - Lifetime
Application number
GB8810634A
Other versions
GB2203151A (en
GB8810634D0 (en
Inventor
William W Lee
Abelardo P Martinez
Martin J Brown
Edward W Grange
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
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 SRI International Inc, Stanford Research Institute filed Critical SRI International Inc
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
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 GB2203151A (en) 1988-10-12
GB2203151B true 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) DE3790581T1 (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
US5616584A (en) 1986-09-25 1997-04-01 Sri International 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents
US5175287A (en) * 1986-09-25 1992-12-29 S R I International Process for preparing 1,2,4-benzotriazine oxides
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
DE68929050T2 (en) 1989-09-18 2000-02-03 Stanford Res Inst Int 1,2,4-BENZOTRIAZINOXIDE AS A RADIO-SENSITIVE AND SELECTIVE CYTOTOXIC AGENT
US5672702A (en) * 1995-12-04 1997-09-30 Sanofi Process for preparing 3 amino 1, 2, 4-benzotriazine dioxide
WO2013086467A1 (en) * 2011-12-07 2013-06-13 Sri International Benzotriazine oxides as drugs targeting mycobacterium tuberculosis
WO2015098963A1 (en) 2013-12-26 2015-07-02 東亞合成株式会社 Method for promoting expression of calreticulin, and synthetic peptide for use in method for promoting expression of calreticulin
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

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2489359A (en) * 1947-01-10 1949-11-29 Merck & Co Inc Benzotriazines
US2489352A (en) * 1946-04-10 1949-11-29 Merck & Co Inc Halogen compounds of 3 aminobenzotriazine 1, 2, 4 oxide-1
US3482024A (en) * 1963-10-22 1969-12-02 Siegfried Ag Zofingen Therapeutic treatment with 1,2-dihydro-1,2,4-benzotriazine derivatives
GB1234845A (en) * 1968-11-16 1971-06-09 Bayer Ag Phosphoric, phosphonic, thionophosphonic and thionophosphoric acid esters
DE2404375A1 (en) * 1973-02-02 1974-08-08 Ciba Geigy Ag 1,2,4-BENZTRIAZINE-1,4-DI-N-OXIDE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND AGENTS CONTAINING THESE COMPOUNDS
FR2322140A1 (en) * 1975-08-27 1977-03-25 Bayer Ag NEW 3-ALKOXY-BENZO-1,2,4-TRIAZINES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS FUNGICIDES AND BACTERICIDES
EP0001090A2 (en) * 1977-09-10 1979-03-21 Bayer Ag Use of 3-halo-benzotriazine-1-oxides in combating bacterial diseases of plants

Patent Citations (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
US3482024A (en) * 1963-10-22 1969-12-02 Siegfried Ag Zofingen Therapeutic treatment with 1,2-dihydro-1,2,4-benzotriazine derivatives
GB1234845A (en) * 1968-11-16 1971-06-09 Bayer Ag Phosphoric, phosphonic, thionophosphonic and thionophosphoric acid esters
DE2404375A1 (en) * 1973-02-02 1974-08-08 Ciba Geigy Ag 1,2,4-BENZTRIAZINE-1,4-DI-N-OXIDE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND AGENTS CONTAINING THESE COMPOUNDS
FR2322140A1 (en) * 1975-08-27 1977-03-25 Bayer Ag NEW 3-ALKOXY-BENZO-1,2,4-TRIAZINES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS FUNGICIDES AND BACTERICIDES
EP0001090A2 (en) * 1977-09-10 1979-03-21 Bayer Ag Use of 3-halo-benzotriazine-1-oxides in combating bacterial diseases of plants

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
Chem Abs Vol 106 No 13, 30 Mar 1987, page 29 and Int J. Radiat Oncol Biol Phys 1986 12(7) 1239-42 *
J. Am Chem Soc Vol 76 No 13, 19 Jul 1954, pages 3551-3553 *
J. Am Chem Soc Vol 76 No 18, 20 Sept 1954, page 4612 table 1 *
J. Chem Soc Sect B part 1, 1970, pages 911-916 *
J. Chromat Vol 131, 1977, paages 448-452 *
J. Het Chem Vol 19, May-June 1982, pages 497-501 *
J. Org. Chem. Vol 24 No 6, 14 July 1959, pages 813-818 *
J. Pharm Sci Vol 69 N0 7, July 1980, pages 789-793 *

Also Published As

Publication number Publication date
GB2203151A (en) 1988-10-12
GB8810634D0 (en) 1988-07-06
JP2668232B2 (en) 1997-10-27
CA1338445C (en) 1996-07-09
DE3790581T1 (en) 1988-08-25
JPH01500826A (en) 1989-03-23
WO1988002366A1 (en) 1988-04-07
DE3790581B4 (en) 2004-12-23

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Legal Events

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

Effective date: 20070615