GB1527497A - Phosphoric acid diamide derivatives - Google Patents

Phosphoric acid diamide derivatives

Info

Publication number
GB1527497A
GB1527497A GB47320/75A GB4732075A GB1527497A GB 1527497 A GB1527497 A GB 1527497A GB 47320/75 A GB47320/75 A GB 47320/75A GB 4732075 A GB4732075 A GB 4732075A GB 1527497 A GB1527497 A GB 1527497A
Authority
GB
United Kingdom
Prior art keywords
compounds
group
formula
ozone
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
GB47320/75A
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co Ltd
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 Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Publication of GB1527497A publication Critical patent/GB1527497A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
    • C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
    • C07F9/65842—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring
    • C07F9/65846—Cyclic amide derivatives of acids of phosphorus, in which one nitrogen atom belongs to the ring the phosphorus atom being part of a six-membered ring which may be condensed with another ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
    • C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2404—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2412—Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic alcohols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1527497 Phosphoric acid diamide derivatives SHIONOGI & CO Ltd 17 Nov 1975 [20 Nov 1974] 47320/75 Heading C2P The invention comprises compounds of the general formula wherein one of X and Y is halogen, e.g. Cl, Br or I, and the other of X and Y is an alkanesulphonyloxy group, R is alkyl and either A is hydrogen and B is a group -CH=C(R 1 )(R 2 ) wherein each of R 1 and R 2 is independently a group which does not interfere with ozone oxidation of the adjacent double bond, or A and B taken together represent the group >CH-OOH. Compounds of the latter type having the Formula I wherein one of X and Y is halogen and the other is a C 1 -C 5 alkane sulphonyloxy group and R is C 1 -C 5 alkyl are therapeutically useful compounds as antitumour agents and as immunosuppressive agents and may be obtained by oxidation with ozone (suitably in the presence of a peroxide, e.g. H 2 O 2 ) of compounds having the Formula II wherein X, Y and R are as defined for (I) and R 1 and R 2 are each independently H, alkyl, aryl or aralkyl. The ozone oxidation may be carried out in a suitable inert solvent using ozone, or oxygen or air containing ozone. Analogous compounds of Formula I but in which R is any alkyl radical and one of X and Y is any alkane sulphonyloxy group may be obtained similarly from the corresponding comnounds in which A is H and B is -CH=C(R 1 )(R 2 ). The compounds II where X is Cl and Y is CH 3 SO 3 , may be prepared by the following reaction scheme and compounds II in which X is CH 3 SO 3 and Y is Cl may be obtained by the following reaction scheme Other compounds II may be prepared similarly. The compounds having the Formula I may be used as active ingredients in pharmaceutical or veterinary compositions in conjunction with appropriate diluents, carriers or excipients.
GB47320/75A 1974-11-20 1975-11-17 Phosphoric acid diamide derivatives Expired GB1527497A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP49133257A JPS5159886A (en) 1974-11-20 1974-11-20

Publications (1)

Publication Number Publication Date
GB1527497A true GB1527497A (en) 1978-10-04

Family

ID=15100374

Family Applications (1)

Application Number Title Priority Date Filing Date
GB47320/75A Expired GB1527497A (en) 1974-11-20 1975-11-17 Phosphoric acid diamide derivatives

Country Status (9)

Country Link
JP (1) JPS5159886A (en)
AU (1) AU500813B2 (en)
CA (1) CA1051914A (en)
CH (1) CH602777A5 (en)
DE (1) DE2552135A1 (en)
FR (1) FR2291763A1 (en)
GB (1) GB1527497A (en)
NL (1) NL7513590A (en)
SE (1) SE7513007L (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3133309A1 (en) * 1980-09-10 1982-04-15 Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld 4-Carbamoyloxyoxazaphosphorines, processes for their preparation, and pharmaceutical preparations containing these compounds
DE3111428A1 (en) * 1981-03-24 1982-10-07 Asta-Werke Ag, Chemische Fabrik, 4800 Bielefeld OXAZAPHOSPHORIN-4-THIO-ALKANESULPHONIC ACIDS AND THEIR NEUTRAL SALTS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS CONTAINING THEM
ZA851062B (en) * 1984-03-01 1985-11-27 Asta Werke Ag Chem Fab Salts of oxazaphosphorine derivatives and process for their production
EP1185276B1 (en) * 1999-05-24 2003-12-10 Southern Research Institute Isophosphoramide mustard analogs and use thereof
CA2585125C (en) 2004-10-25 2014-04-22 Lee Morgan Salts of isophosphoramide mustard and analogs thereof as anti-tumor agents
US7964583B2 (en) 2006-02-17 2011-06-21 Ziopharm Oncology, Inc. Salts of isophosphoramide mustard and analogs thereof as anti-tumor agents
PT2155682E (en) 2007-04-06 2015-10-15 Ziopharm Oncology Inc Salts of isophosphoramide mustard and analogs thereof

Also Published As

Publication number Publication date
CA1051914A (en) 1979-04-03
JPS5159886A (en) 1976-05-25
DE2552135A1 (en) 1976-05-26
NL7513590A (en) 1976-05-24
FR2291763A1 (en) 1976-06-18
SE7513007L (en) 1976-05-21
CH602777A5 (en) 1978-07-31
AU500813B2 (en) 1979-05-10
AU8681675A (en) 1977-05-26

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee