AR037479A1 - 1,3-DIARILPROP-2-EN-1-ONAS, COMPOSITIONS THAT CONTAIN THEM AND ITS USE - Google Patents

1,3-DIARILPROP-2-EN-1-ONAS, COMPOSITIONS THAT CONTAIN THEM AND ITS USE

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Publication number
AR037479A1
AR037479A1 ARP020104618A ARP020104618A AR037479A1 AR 037479 A1 AR037479 A1 AR 037479A1 AR P020104618 A ARP020104618 A AR P020104618A AR P020104618 A ARP020104618 A AR P020104618A AR 037479 A1 AR037479 A1 AR 037479A1
Authority
AR
Argentina
Prior art keywords
alkyl
group
substituted
cycloalkyl
methoxy
Prior art date
Application number
ARP020104618A
Other languages
Spanish (es)
Original Assignee
Aventis Pharma Sa
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
Priority claimed from FR0115739A external-priority patent/FR2833008B1/en
Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa
Publication of AR037479A1 publication Critical patent/AR037479A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
    • C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
    • C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide 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
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/30—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
    • C07C279/32—N-nitroguanidines
    • C07C279/36—Substituted N-nitroguanidines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Abstract

1,3-Diarilprop-2-en-1-onas y derivados, composiciones que los contienen, procedimiento para la fabricación y utilización. La presente se refiere, principalmente, a nuevas 1,3-diarilprop-2-en-1-onas sustituidas, que tienen una actividad terapéutica, utilizadas, en particular, en oncología. Reivindicación 1: Producto que responde a la fórmula (1) en la que: a) Y se elige el grupo formado por halógeno, alquilo lineal C1-7, alquilo ramificado C1-7, alquilo lineal C1-7 sustituido, alquilo ramificado C1-7 sustituido, cicloalquilo, cicloalquilo sustituido, NH2, NH(R4), N(R4)2, aralquilo, aralquilo sustituido, COOH, COO(R4), CONH2, CONH(R4), CON(R4)2, CN, en el que R4 representa un grupo alquilo o cicloalquilo C1-7 eventualmente sustituido, y cuando estén presente dos R4, pueden estar enlazados entre sí para formar un ciclo; b) Ar2 se elige del grupo formado por: fórmula (2), (3) en la que: 1) cuando Ar2 es fórmula (2), entonces uno de R1, R2 se elige del grupo formado por NH2, NH2 HZ, NHC(O)-ácido aminado, NH-(GP); N=(GP); en el que el ácido aminado es preferentemente la serina; en el que GP es un sustituyente metabolizable que permita el cambio de grupo funcional: NH-(GP) ---NH2 ó N=(GP) --- NH2 y en el que HZ es un ácido orgánico ó mineral; y el otro de R1, R2 se elige del grupo formado por CH3, C2H5, OCH3, OC2H5, SCH3, NH(R5), N(R5)2, N(R5)(GP), N(R5)C(O)-ácido aminado, en el que R5 representa un grupo alquilo C1-2 y cuando dos R5 estén presente, pueden estar enlazados entre sí para formar un ciclo; 2) cuando Ar2 es fórmula (3), entonces A es un heterociclo con 5 ó 6 eslabones, condensado sobre un ciclo bencénico B, siendo el citado heterociclo A aromático ó no-aromático, que comprende 1 ó 2 heteroátomos, uno de los cuales, al menos, es un átomo de nitrógeno directamente enlazado con B y portador de una cadena lateral R8, en el que R8 se elige del grupo constituido por H, alquilo C1-3, alquilo C1-3-OH, alquilo C1-3-O alquilo C1-3, alquilo C1-3-NH2, alquilo C1-3-NH(R7), alquilo C1-3-N(R7)2, fórmula (4) en el que R9 se elige entre H, alquilo C1-3, en el que cada R7 representa independientemente un grupo alquilo C1-3 ó cicloalquilo C1-3, ó bien, cuando dos R7 estén presentes, están enlazadas entre sí para formar un heterociclo con 5 eslabones; c) X se elige del grupo formado por O, NOH, NO(R3), en el que R3 se elige del grupo formado por H, alquilo lineal C1-7, alquilo ramificado C1-7, cicloalquilo, alquilo lineal C1-7 halogenado, alquilo ramificado C1-7 halogenado, cicloalquilo sustituido, cicloalquilo halogenado, aralquilo, aralquilo sustituido; y d) Ar se elige del grupo formado por 2,5-dimetoxifenilo, 2,3,4-trimetoxifenilo, 3,4-5-trimetoxifenilo, 2,3-5-trimetoxifenilo, 2,4,5-trimetoxifenilo, 2,3,4,5-tetrametoxifenilo, 3-metoxi-4,5-metilendioxi, 3-metoxi-4,5-etilendioxi, 2-metoxi-4,5-metilendioxi, 2-metoxi-4,5-etilendioxi, 2-metoxi-3,4-metilendioxi, 2-metoxi-3,4-etilendioxi.1,3-Diarylprop-2-en-1-ones and derivatives, compositions containing them, process for manufacturing and use. This refers mainly to new substituted 1,3-diarylprop-2-in-1-ones, which have a therapeutic activity, used, in particular, in oncology. Claim 1: Product that responds to formula (1) in which: a) The group consisting of halogen, C1-7 linear alkyl, C1-7 branched alkyl, substituted C1-7 linear alkyl, C1- branched alkyl is chosen 7 substituted, cycloalkyl, substituted cycloalkyl, NH2, NH (R4), N (R4) 2, aralkyl, substituted aralkyl, COOH, COO (R4), CONH2, CONH (R4), CON (R4) 2, CN, in that R4 represents an optionally substituted C1-7 alkyl or cycloalkyl group, and when two R4 are present, they can be linked together to form a cycle; b) Ar2 is chosen from the group consisting of: formula (2), (3) in which: 1) when Ar2 is formula (2), then one of R1, R2 is chosen from the group consisting of NH2, NH2 HZ, NHC (O) -aminated acid, NH- (GP); N = (GP); wherein the amino acid is preferably serine; in which GP is a metabolizable substituent that allows the change of functional group: NH- (GP) --- NH2 or N = (GP) --- NH2 and in which HZ is an organic or mineral acid; and the other of R1, R2 is chosen from the group consisting of CH3, C2H5, OCH3, OC2H5, SCH3, NH (R5), N (R5) 2, N (R5) (GP), N (R5) C (O) -aminated acid, in which R5 represents a C1-2 alkyl group and when two R5 are present, they can be linked together to form a cycle; 2) when Ar2 is formula (3), then A is a heterocycle with 5 or 6 links, condensed on a benzene cycle B, said aromatic or non-aromatic heterocycle A, comprising 1 or 2 heteroatoms, one of which At least it is a nitrogen atom directly linked to B and a carrier of a side chain R8, in which R8 is selected from the group consisting of H, C1-3 alkyl, C1-3-OH alkyl, C1-3 alkyl- Or C1-3 alkyl, C1-3-NH2 alkyl, C1-3-NH alkyl (R7), C1-3-N alkyl (R7) 2, formula (4) in which R9 is selected from H, C1- alkyl 3, in which each R7 independently represents a C1-3 alkyl or C1-3 cycloalkyl group, or, when two R7 are present, are linked together to form a 5-link heterocycle; c) X is chosen from the group consisting of O, NOH, NO (R3), in which R3 is selected from the group consisting of H, C1-7 linear alkyl, C1-7 branched alkyl, cycloalkyl, halogenated C1-7 linear alkyl , halogenated C1-7 branched alkyl, substituted cycloalkyl, halogenated cycloalkyl, aralkyl, substituted aralkyl; and d) Ar is selected from the group consisting of 2,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl, 3,4-5-trimethoxyphenyl, 2,3-5-trimethoxyphenyl, 2,4,5-trimethoxyphenyl, 2,3 , 4,5-tetramethoxyphenyl, 3-methoxy-4,5-methylenedioxy, 3-methoxy-4,5-ethylenedioxy, 2-methoxy-4,5-methylenedioxy, 2-methoxy-4,5-ethylenedioxy, 2-methoxy -3,4-methylenedioxy, 2-methoxy-3,4-ethylenedioxy.

ARP020104618A 2001-12-05 2002-11-29 1,3-DIARILPROP-2-EN-1-ONAS, COMPOSITIONS THAT CONTAIN THEM AND ITS USE AR037479A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0115739A FR2833008B1 (en) 2001-12-05 2001-12-05 1,3-DIARYLPROP-2-IN-1-ONES, COMPOSITIONS CONTAINING THEM, AND USE
FR0214217 2002-11-14

Publications (1)

Publication Number Publication Date
AR037479A1 true AR037479A1 (en) 2004-11-10

Family

ID=26213287

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP020104618A AR037479A1 (en) 2001-12-05 2002-11-29 1,3-DIARILPROP-2-EN-1-ONAS, COMPOSITIONS THAT CONTAIN THEM AND ITS USE

Country Status (23)

Country Link
EP (1) EP1453790A2 (en)
JP (1) JP2005531494A (en)
KR (1) KR20050044712A (en)
CN (1) CN1612856A (en)
AR (1) AR037479A1 (en)
AU (1) AU2002365644A1 (en)
BR (1) BR0214694A (en)
CA (1) CA2469193A1 (en)
CO (1) CO5580759A2 (en)
EA (1) EA006803B1 (en)
HR (1) HRP20040508A2 (en)
HU (1) HUP0500100A2 (en)
IL (1) IL162223A0 (en)
MA (1) MA27351A1 (en)
MX (1) MXPA04005226A (en)
NZ (1) NZ533224A (en)
PA (1) PA8558501A1 (en)
PE (1) PE20030758A1 (en)
PL (1) PL370676A1 (en)
RS (1) RS47804A (en)
SV (1) SV2003001422A (en)
TW (1) TW200300685A (en)
WO (1) WO2003048106A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2854399B1 (en) * 2003-04-30 2006-11-17 Aventis Pharma Sa 1-ARYL-3- (INDOL-5-YL) -PROP-2-EN-1-ONES, COMPOSITIONS CONTAINING SAME AND USE THEREOF
EP1598353A1 (en) 2004-05-17 2005-11-23 Boehringer Ingelheim International GmbH Pyrrolobenzimidazolones and their use as antiproliferative agents
WO2017103637A1 (en) 2015-12-18 2017-06-22 Blirt S.A. Diphenylpropane compounds and their cytotoxic activity
CN109467549B (en) * 2018-12-07 2021-02-09 中国药科大学 Quinoline-substituted chalcone compound, preparation method and application thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4904697A (en) * 1987-04-09 1990-02-27 Merrell Dow Pharmaceuticals Inc. Controlling the growth of certain tumor tissue with chalcone derivatives
JPH08277242A (en) * 1995-02-08 1996-10-22 Kyowa Hakko Kogyo Co Ltd Propenone derivative
ATE259353T1 (en) * 1995-12-01 2004-02-15 Kyowa Hakko Kogyo Kk PROPENONE DERIVATIVES
WO1999000114A2 (en) * 1997-06-26 1999-01-07 Statens Serum Institut Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones

Also Published As

Publication number Publication date
AU2002365644A1 (en) 2003-06-17
IL162223A0 (en) 2005-11-20
HRP20040508A2 (en) 2005-08-31
SV2003001422A (en) 2003-07-10
MA27351A1 (en) 2005-06-01
WO2003048106A3 (en) 2004-03-25
BR0214694A (en) 2004-12-14
CN1612856A (en) 2005-05-04
PA8558501A1 (en) 2003-09-05
HUP0500100A2 (en) 2005-05-30
TW200300685A (en) 2003-06-16
PE20030758A1 (en) 2003-10-07
EP1453790A2 (en) 2004-09-08
WO2003048106A2 (en) 2003-06-12
PL370676A1 (en) 2005-05-30
MXPA04005226A (en) 2004-10-11
EA006803B1 (en) 2006-04-28
KR20050044712A (en) 2005-05-12
JP2005531494A (en) 2005-10-20
NZ533224A (en) 2006-03-31
CA2469193A1 (en) 2003-06-12
RS47804A (en) 2006-12-15
CO5580759A2 (en) 2005-11-30
EA200400764A1 (en) 2004-12-30

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