AR065154A1 - PROCEDURE FOR PREPARATION OF SULFANYLAMIDES AND FLUORATED SULFINAMIDINS AND THEIR USES - Google Patents

PROCEDURE FOR PREPARATION OF SULFANYLAMIDES AND FLUORATED SULFINAMIDINS AND THEIR USES

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Publication number
AR065154A1
AR065154A1 ARP080100448A ARP080100448A AR065154A1 AR 065154 A1 AR065154 A1 AR 065154A1 AR P080100448 A ARP080100448 A AR P080100448A AR P080100448 A ARP080100448 A AR P080100448A AR 065154 A1 AR065154 A1 AR 065154A1
Authority
AR
Argentina
Prior art keywords
formula
group
optionally substituted
compound
aryl
Prior art date
Application number
ARP080100448A
Other languages
Spanish (es)
Inventor
Bernard Langlois
Thierry Billard
Aurelien Ferry
Youssef El-Ahmad
Eric Bacque
Original Assignee
Aventis Pharma Sa
Centre Nat Rech Scient
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 Aventis Pharma Sa, Centre Nat Rech Scient filed Critical Aventis Pharma Sa
Publication of AR065154A1 publication Critical patent/AR065154A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/08—Sulfenic acids; Derivatives thereof
    • C07C313/18—Sulfenamides
    • C07C313/20—Sulfenamides having sulfur atoms of sulfenamide groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/08—Sulfenic acids; Derivatives thereof
    • C07C313/18—Sulfenamides
    • C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C313/30—Y being a hetero atom
    • C07C313/32—X and Y not being nitrogen atoms, e.g. N-sulfenylcarbamic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • 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
    • C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07C323/23—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/46—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
    • C07C323/49—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 nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/06—Compounds containing sulfur atoms only bound to two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/36—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicacion 1: Procedimiento de preparacion del compuesto sulfanilamida de formula (1) y del compuesto sulfinamidina de formula (2) en las que a) R1 representa: bien un grupo arilo opcionalmente sustituido; bien un grupo heteroarilo opcionalmente sustituido; bien un grupo alquilo opcionalmente sustituido; bien un grupo cicloalquilo opcionalmente sustituido; bien un grupo heterocicloalquilo opcionalmente sustituido; bien un grupo -SO2-arilo en el que el arilo está opcionalmente sustituido; bien un grupo -SO2-heteroarilo en el que el heteroarilo está opcionalmente sustituido; bien un grupo -SO2-fluoroalquilo; bien un grupo -CO2-arilo en el que el arilo está opcionalmente sustituido; bien un grupo -CO2-heteroarilo en el que el heteroarilo está opcionalmente sustituido; bien un grupo -CO2-alquilo en el que el alquilo está opcionalmente sustituido; b) R2 representa un grupo perfluoroalquilo o difluorometileno sustituido por un grupo -S-arilo, -S-heteroarilo o benzoxazol-2- ilo opcionalmente sustituido, c) R3 y R4 representan independientemente uno del otro un grupo alquilo, alcoxialquilo o cicloalquilo o bien R3 y R4 forman junto con el átomo de nitrogeno al que están unidos, un heterociclo saturado o insaturado de 3 a 7 eslabones que comprende opcionalmente otro heteroátomo (tal como piperidinilo, pirrolidinilo o morfolinilo); caracterizado porque se ejecutan las etapas siguientes: una primera etapa, en la que el compuesto de formula (4) se condensa con un compuesto de formula (5) en presencia de una amina terciaria en un disolvente orgánico, para dar el compuesto de formula (3), en las que R1, R2, R3 y R4 son tales como se ha definido anteriormente y R5, R6 y R7 representan independientemente uno del otro un grupo seleccionado entre los grupos alquilo o arilo opcionalmente sustituido; una segunda etapa, en la que el compuesto de formula (3) está condensado con un compuesto de formula R1NH2, en la que R1 es tal como se ha se ha definido anteriormente, en presencia de una amina terciaria en un disolvente orgánico, para dar sulfanilamida de formula (1) y/o un compuesto sulfinamidina de formula (2), en la que R1, R2, R3 y R4 son tales como se ha definido anteriormente; opcionalmente una tercera etapa, en la que el compuesto sulfinamidina de formula (2) o la mezcla sulfanilamida de formula (1) y sulfinamidina de formula (2) se transforma en un disolvente orgánico en presencia de un ácido para dar un compuesto sulfanilamida de formula (1), en las que R1 y R2, R3 y R4 son tales como se ha definido anteriormente.Claim 1: Preparation process of the sulfanilamide compound of formula (1) and of the sulfinamidine compound of formula (2) in which a) R 1 represents: either an optionally substituted aryl group; either an optionally substituted heteroaryl group; either an optionally substituted alkyl group; either an optionally substituted cycloalkyl group; either an optionally substituted heterocycloalkyl group; or a -SO2-aryl group in which the aryl is optionally substituted; or a -SO2-heteroaryl group in which the heteroaryl is optionally substituted; either a -SO2-fluoroalkyl group; or a -CO2-aryl group in which the aryl is optionally substituted; or a -CO2-heteroaryl group in which the heteroaryl is optionally substituted; or a -CO2-alkyl group in which the alkyl is optionally substituted; b) R2 represents a perfluoroalkyl or difluoromethylene group substituted by an optionally substituted -S-aryl, -S-heteroaryl or benzoxazol-2- yl group, c) R3 and R4 independently represent each other an alkyl, alkoxyalkyl or cycloalkyl group or R3 and R4 together with the nitrogen atom to which they are attached, a saturated or unsaturated heterocycle of 3 to 7 links optionally comprising another heteroatom (such as piperidinyl, pyrrolidinyl or morpholinyl); characterized in that the following steps are executed: a first stage, in which the compound of formula (4) is condensed with a compound of formula (5) in the presence of a tertiary amine in an organic solvent, to give the compound of formula ( 3), wherein R1, R2, R3 and R4 are as defined above and R5, R6 and R7 independently represent one another from a group selected from the optionally substituted alkyl or aryl groups; a second step, in which the compound of formula (3) is condensed with a compound of formula R1NH2, in which R1 is as defined above, in the presence of a tertiary amine in an organic solvent, to give sulfanilamide of formula (1) and / or a sulfinamidine compound of formula (2), wherein R1, R2, R3 and R4 are as defined above; optionally a third step, in which the sulfinamidine compound of formula (2) or the sulfanilamide mixture of formula (1) and sulfinamidine of formula (2) is transformed into an organic solvent in the presence of an acid to give a sulfanilamide compound of formula (1), in which R1 and R2, R3 and R4 are as defined above.

ARP080100448A 2007-02-05 2008-02-04 PROCEDURE FOR PREPARATION OF SULFANYLAMIDES AND FLUORATED SULFINAMIDINS AND THEIR USES AR065154A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0700792A FR2912132A1 (en) 2007-02-05 2007-02-05 Preparation of fluorinated sulfanylamide and sulfinamidine for use as substitutes for bioactive molecules, involves reacting dialkylamino sulfur trifluoride with perfluoroalkylsilane and then with prim. amine

Publications (1)

Publication Number Publication Date
AR065154A1 true AR065154A1 (en) 2009-05-20

Family

ID=38515783

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP080100448A AR065154A1 (en) 2007-02-05 2008-02-04 PROCEDURE FOR PREPARATION OF SULFANYLAMIDES AND FLUORATED SULFINAMIDINS AND THEIR USES

Country Status (13)

Country Link
EP (1) EP2114874A2 (en)
JP (1) JP2010517985A (en)
KR (1) KR20090106595A (en)
CN (1) CN101668735A (en)
AR (1) AR065154A1 (en)
AU (1) AU2008224784A1 (en)
BR (1) BRPI0807119A2 (en)
CA (1) CA2677295A1 (en)
FR (1) FR2912132A1 (en)
IL (1) IL200190A0 (en)
MX (1) MX2009008314A (en)
TW (1) TW200840576A (en)
WO (1) WO2008110698A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9682960B2 (en) * 2013-12-19 2017-06-20 Endorecherche, Inc. Non-steroidal antiandrogens and selective androgen receptor modulators with a pyridyl moiety
CN104945348B (en) * 2014-03-31 2017-08-29 深圳市中科邦奇氟医学材料有限公司 Trifluoromethylthio reagent, synthetic method and its application
CN106748915A (en) * 2015-11-20 2017-05-31 南京理工大学 A kind of trifluoromethylthio reagent and its application
CN115772107A (en) * 2022-12-15 2023-03-10 岭南师范学院 Preparation method of sulfimide ester/amide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3976769A (en) * 1970-09-11 1976-08-24 Airwick Industries, Inc. Pesticidal compositions containing phosphoric esters and divalent sulphur compounds

Also Published As

Publication number Publication date
CA2677295A1 (en) 2008-09-18
KR20090106595A (en) 2009-10-09
JP2010517985A (en) 2010-05-27
FR2912132A1 (en) 2008-08-08
WO2008110698A2 (en) 2008-09-18
WO2008110698A3 (en) 2008-11-06
BRPI0807119A2 (en) 2014-04-08
IL200190A0 (en) 2010-04-15
EP2114874A2 (en) 2009-11-11
CN101668735A (en) 2010-03-10
TW200840576A (en) 2008-10-16
MX2009008314A (en) 2009-08-13
AU2008224784A1 (en) 2008-09-18

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