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WO2006093336A1 - Emploi d'un composé de type cinnamoyle - Google Patents

Emploi d'un composé de type cinnamoyle Download PDF

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Publication number
WO2006093336A1
WO2006093336A1 PCT/JP2006/304531 JP2006304531W WO2006093336A1 WO 2006093336 A1 WO2006093336 A1 WO 2006093336A1 JP 2006304531 W JP2006304531 W JP 2006304531W WO 2006093336 A1 WO2006093336 A1 WO 2006093336A1
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PCT/JP2006/304531
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English (en)
Japanese (ja)
Inventor
Kiyoshi Higashi
Yoshitaka Tomigahara
Junya Takahashi
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Sumitomo Chemical Company, Limited
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Publication of WO2006093336A1 publication Critical patent/WO2006093336A1/fr

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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/69—Two or more oxygen atoms
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    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4704—2-Quinolinones, e.g. carbostyril
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    • 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
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
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    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
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    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • the present invention relates to the use of cinnamoyl compounds.
  • TGF-jS a kind of cytokine
  • TGF-i3 increases the expression level of fibronectin gene, and is involved in increased production of fibronectin and, in turn, tissue fibrosis.
  • administration of anti-TGF-j3 antibody • or soluble TGF- / 3 receptor to tissue fibrosis model animals improves tissue fibrosis, which in turn improves tissue function.
  • heart failure such as left ventricular diastolic failure
  • hypertension heart fibrosis has been.
  • the present invention relates to the use of a compound represented by the following formulas (I) to (IV) having the ability to suppress the transcription of a fibronectin gene.
  • I. A represents a benzene ring or a pyridine ring
  • (Y a ) g , ⁇ a is a substituent on the carbon atom, Group or Y.
  • Q represents 0, 1, 2, 3, 4 or 5, when Q is 2 or more, Q ⁇ is the same or different, and when q is 2 or more, adjacent to each other
  • ⁇ ⁇ is the following X. Group, ⁇ . Swarm and eagle. Represents a substituent on a carbon atom not belonging to the group, ⁇ represents 0, 1, 2, 3, 4 or 5, and when ⁇ is 2 or more, X a is the same or different, and p and Q The sum of is less than 5.
  • M a is an R b — group (R b represents a CI-C10 alkyl group which may be substituted with a halogen atom), a halogen atom, a nitro group, a cyano group, a hydroxyl group, R c — B a _R d — group (R c represents a CI-CIO alkyl group which may be substituted with a halogen atom, and B a represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group.
  • R d represents a single bond or a C1-C10 alkylene group.
  • H0R d — group R d represents the same meaning as described above
  • R e — CO— R d — group R e represents a hydrogen atom or a C ⁇ C10 alkyl group which may be substituted with a halogen atom, and R d represents the same meaning as described above.
  • R e — CO— NR e , — R d — group (R e , R e , and R d represent the same meaning as described above), R b 0-CO-N (R e ) and R d — group (R b , R e and R d have the same meanings as above), R e R e 'N— C ⁇ 1 R d — group (R e , R e , and R d are ), R e R e 'N—CO—NR e ′, one R d — group (R e , R e , and R e ′ are the same or different, and R e and R e, represents the same meanings, R e, 'represents the same meaning as described R e, R d represents the same meaning as above.), R e R e, N C ( NR e ,,) One NR e ',, -R d (R e ), R
  • M b . —R d — group [M b o is a single M c o group ⁇ M c . Is an M d 0- R d , — group ⁇ M d Q may be substituted with a M a — group (M a represents the same meaning as above) • 6— 10-membered ring aryl Group, or M a — group (M a represents the same meaning as described above.
  • M a represents the same meaning as described above.
  • G. represents a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent.
  • J. may contain a nitrogen atom and is aromatic 5-7 member. :
  • R e N—CO—NR e ′ Mc Q , R e and R e ′ have the same meaning as described above
  • One S_ ⁇ 2 -NR e one group (M c. And R e represent the same meaning.)
  • R e N— S0 2 — represents a group (M e . And R e represent the same meaning as described above), and R d represents the same meaning as described above. ]
  • Z 0 group halogen atom, CI-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfoni group
  • Q a represents a hydroxyl group that may be substituted or an amino group that may be substituted.
  • W a represents an oxygen atom or a single NT a - (the T alpha, hydrogen atom, or represents a substituent on the nitrogen atom.) Group represents a.
  • kappa alpha and L a are the same or different, a hydrogen atom, or represents a substituent on a carbon atom, kappa alpha and A L a, may also be C1-C10 alkylene group which may have a substituent Alternatively, it may form a C1-C10 alkenylene group which may have a substituent.
  • the A ring is a benzene ring
  • a is an oxygen atom
  • L a is a methyl group
  • kappa alpha is hydrogen atom
  • Q a is C1-C4 alkoxy group
  • the a ring is a benzene ring
  • W a is oxygen atom
  • L a is a methyl group
  • K a is hydrogen
  • Q a is C1-C4 alkoxy group
  • q is 1, and
  • Y a is a halogen atom, or a CI-C4 alkyl group optionally substituted with a halogen atom or a CI-C4 alkoxy group, Or a nitro group, or
  • A is a benzene ring
  • W ⁇ is an oxygen atom
  • L a and ⁇ ⁇ are 1,3-butagenylene ⁇
  • Q a is a methoxy group
  • Q is 1 and ⁇ ⁇ is a methoxy group
  • W a is an oxygen atom
  • L a and ⁇ ⁇ are 1,3-butagenylene groups
  • Q a is a hydroxyl group
  • q is 1 and ⁇ ⁇ Is not an ethoxy group.
  • a composition for inhibiting transcription of a fibronectin gene comprising a cinnamoyl compound represented by the formula: and an inert carrier;
  • I. ⁇ represents a benzene ring or a pyridine ring.
  • a group 0 : — R 4 — group is — (O) k1 ) A, N— (O) k ′ one group is a hydrogen atom, or a C ⁇ C10 alkyl group, or a halogen atom.
  • R 2 — — group (R 2 represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group, and represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group.) Represents a C2-C10 alkyl group, a C3-C10 alkenyl group, or a C3-C10 alkynyl group substituted with k, k represents 0 or 1, and A represents R 3 — (CHR) m — ( B 2 — B 3 ) m .
  • R 3 is a hydrogen atom, a halogen atom or an R 2 -B 2 group (R 2 and 8 are the same as defined above)
  • R represents a CI-C10 alkyl group, a C2-C10 alkenyl group, or a C2-C10 alkynyl group.
  • C1-C10 Represents an alkyl group or a C2-CIO haloalkyl group
  • m represents 0 or 1
  • B 2 represents a single bond, an oxy group, a thio group or —N ((O) n R x ′) one group (R ′ Is the same as or different from, and represents the same meaning as, and n represents 0 or 1.)
  • B 3 represents a force Rupoel group, a thiocarbonyl group, or a sulfonyl group
  • m ′ represents When 0 or 1 is represented and B 3 is a sulfonyl group, m is 0 and R 3 is not a hydrogen atom.
  • ⁇ , And k ′ represents 0 or 1.
  • ⁇ And R 4 represents a ⁇ -CIO alkylene group.
  • R. 'R. ', NR 4 single unit R., and R.,' is the same as or different from R, and has the same meaning as R., R 4 has the same meaning as above) .
  • R 2 one group (Ai and R 2 represent the same meaning as described above) or NH 2 _CS— group, and R 4 represents the same meaning as described above. ]
  • D 3 — R 4 — group ⁇ D 3 represents a nitro group or R
  • ⁇ S0 2 — group has the same meaning as described above.
  • R 4 represents the same meaning as described above.
  • ⁇ Or OS ⁇ 2 — group (Ri represents the same meaning as described above).
  • E Q may have a substituent, which is a saturated or unsaturated, aromatic or non-aromatic 5- to 14-membered hydrocarbon ring or heterocyclic ring, and Represents the same meaning as above. .
  • R 4 — group (in (b.), G. is an optionally substituted, saturated or unsaturated, non-aromatic, 5-14 membered hydrocarbon ring or heterocycle; Make a ring)
  • J. may include a nitrogen atom, form a aromatic 5- 7 membered ring, R 4 represents the same meaning as above..
  • a halogen atom R 2 - 1 one R 4 — group (R 2 , B 1 and R 4 are as defined above), D 4 — R 4 — group (D 4 and R 4 are as defined above), D 5 — group (D 5 represents the same meaning as described above), D 1 R 4 — group and R represent the same meaning as described above. ), D 2 — group (D 2 is Represents the same meaning as described above. ) Or D 3 - R 4 - group (D 3 and R 4, have been C2- C10 alkynyl group substituted with representing) the same meaning as above.
  • R 5 is not a vinylene group.
  • ⁇ A 3 is a hydrogen atom, or a C ⁇ C10 alkyl group, or a C2-C10 haloalkyl group, or a C2-C10 alkenyl group that may be substituted with a halogen atom, or a halogen atom.
  • R a D — (R 4 ) m — group R a represents an optionally substituted 5- to 7-membered aryl group or heteroaryl group, 4 and m are ), Or (b Q ) — R 4 — group ((b.) And R 4 represent the same meaning as above), (c Q ) — R 4 — group ((C Q ) and R 4 represent the same meaning as described above.), R 2 -R 4 — group (R 2 , Bu and R 4 represent the same meaning as described above;), D 4 — R 4 — group (D 4 and R 4 have the same meaning as above:), D 5 single group (D 5 has the same meaning as above), — R 4 — group ( 0 and R 4 are ), D 2 — group (D 2 represents the same meaning as described above), D 3 R 4 — group (D 3 and R 4 have the same meaning as described above) Or A 4 — S0 2 — R 4 — group ⁇
  • B 4 represents an oxy group, a thio group, or one N ((O) m ) one group and m represents the same meaning as described above. )
  • B 4 is a thio group
  • a 3 is not a hydrogen atom.
  • Ri _B 4 — CO— R 4 — B 4 one unit (I ⁇ , B 4 and R 4 have the same meaning as above, B 4 ′ is the same as or different from B 4 , B 4 represents the same meaning as the proviso that when B 4 is Chio group, R 2 is not hydrogen atom) or D 2 '-.. R 4 - B 4 - group (D 2, R 4 and B 4 represent the same meaning as described above. ),
  • R x A x N-NR X ' represents one group (Ri, A and R''represent the same meaning as described above), and R 5 may be substituted with a halogen atom.
  • R x A x N-NR X ' represents one group (Ri, A and R''represent the same meaning as described above), and R 5 may be substituted with a halogen atom.
  • a 5 — B 5 — R 6 — group [A 5 represents D 4 — group (D 4 represents the same meaning as described above;), — group represents the same meaning as described above. ), D 3 — group (D 3 represents the same meaning as described above) or A 4 — S0 2 — group (A 4 represents the same meaning as described above) substituted with C2-C10
  • R 6 represents a single bond or a CI-C10 alkylene group.
  • [A 6 is (a.) One R 4 — group ((a.) And R 4 are as defined above.), Or a C2-C10 alkenyl group, or a C2-C10 alkynyl group, Or, a halogen atom, a single R 2 group (R 2 and are the same as defined above :), D 5 — group (D 5 is as defined above), D 2 — group ( D 2 is the representative of the same meaning as) Wakashi clause a 2 -..
  • CO- group (a 2 are C2-C10 an alkenyl group substituted with representing) the same meaning as above, or, A halogen atom, R 2 to B, one group (R 2 and are as defined above), D 5 — group (D 5 is as defined above), D 2 — group (D 2 represents the same meaning as described above) or A 2 —CO— group (A 2 represents the same meaning as described above) substituted with a C2-C10 alkynyl group, or (b ′ .) —Group ((b.) Is the previous This means the same meaning as above.
  • (C Q ) — group ((c.) Represents the same meaning as described above :), D 4 — group (D 4 represents the same meaning as described above), 0 group Represents the same meaning as described above. ) Or D 3 — group (D 3 represents the same meaning as described above) or a C3-C10 alkenyl group substituted with D 4 — group (D 4 represents the same meaning as described above.) 0 group represents the same meaning as described above. ) Or a D 3 — group (D 3 represents the same meaning as described above), and represents a C3-C10 alkynyl group substituted with B 5 and R 6 represent the same meaning as described above. ]
  • n -N CR ' one NR 2 - R 6 — group (R i, n, ', R 2 and R 6 have the same meaning as above), R 2 — B 3 — NR 1 -CO-NRi, one R 6 — group (R 2 , B 3 , ′ and R 6 represent the same meaning as described above.), D 2 —CO—NRi One R 6 — group (D 2 , R x and R 6 represent the same meaning as described above) ) Or A 2 — CO CO— NR — R 6 — group (where A 2 , R x and R 6 • represent the same meaning as described above.)
  • a 7 -B 6 N ((O) n R,) — R 6 — group [A 7 is optionally substituted with a halogen atom C2-C10 alkenyl group, C2-C10 alkynyl group, C3-C10 haloalkynyl Group, R 2 — B ⁇ — R 4 — group (R 2 ,. And R 4 have the same meaning as above), D 4 — R 4 — group (D 4 and R 4 are the same as above) ), D 5 — R 4 — group (D 5 and R 4 have the same meaning as above), D — R 4 — group 'and R 4 have the same meaning as above. To express.
  • One R 6 — group [A 8 represents a hydrogen atom or a C1-C10 alkyl group optionally substituted with a rogen atom, n, R, And R 6 represents the same meaning as described above. ]
  • a 7 ' is a C3-C10 alkenyl group that may be substituted with an octalogen atom, a haguchigen atom
  • a C3-C10 alkynyl group optionally substituted by R 2 — Bi — R 4 ′ one group (R 2 and are the same as defined above, and R 4 ′ represents a C2-C10 alkylene group.
  • One R 6 — group [A 7 , is a C2-CIO alkenyl group, a C3-CIO alkenyl group substituted with a halogen atom, halogen C3-C10 alkynyl group which may be substituted by an atom, R 2 — — R 4 , — group (R 2 and R 4 have the same meaning as above), D 4 — R 4 ′ —
  • the groups (D 4 and R 4 ' ⁇ have the same meaning as above.
  • D 5 — R 4 — group (D 5 and R 4 have the same meaning as above;), — R 4 ′ — group (Di and R 4 ′ have the same meaning as above, P ) (bo) ⁇ R 4 '-group ((b.) and R 4 ' represent the same meaning as above :), (c Q ) — R 4 '— group ((c 0 ) and R 4 'Represents the same meaning as described above;), D 2 — R 4 — group (D 2 and R 4 represent the same meaning as described above), N0 2 ——R 4 — group (R 4 Represents the same meaning as described above.) Or A 2 —CO—R 4 — group (wherein A 2 and R 4 represent the same meaning as described above), and n, R x and R 6 represent Represents the same meaning as above. ]
  • a 9 and R 6 have the same meaning as described above,' represents an oxy group or a thio group, and when 'is an oxy group, A 9 is Not A 8 ), or A 9 -C SB 1 , -R 6 1 group (A 9 , 1 ′ and R 6 are as defined above), or A 7 , '-S0 2 ' One R 6 — group (A 7 ,,, B 1 'and R 6 are
  • a 8 — S0 2 _B 1 '— R 6 — group (A 8. B x ′ and R 6 represent the same meaning as described above, provided that A 8 represents a hydrogen atom. . no), or, a 9, one B 2, -B 3 - 1 'one R 6 - group (a 9,, B 2, , B 3,,' and R 6 are, the same as the )
  • Or (b.) — Group ((b 0 ) represents the same meaning as described above.)
  • Or (c.) — Group ((c Q ) represents the same meaning as described above.
  • A. Is a hydrogen atom (however, n is not 0;), A 7 '' — S0 2 — group '(A 7 ''represents the same meaning as above), A 8 — S ⁇ 2 —Group (A 8 represents the same meaning as above. However, A 8 is not a hydrogen atom.)
  • R 2 is represents the same meaning
  • a 2 -. CO- R 4 -. group (a 2 and R 4 represent the same meanings as the above) or a 2 -CO-CH (CH 2 CO- a 2 )
  • One group (A 2 represents the same meaning as described above), and n, 1 ⁇ and R 6 represent the same meaning as described above. ]
  • L 0 group At 0 '— N ((O) n R x ) — S ⁇ 2 — R 6 — group [A t 0 , is a hydrogen atom (where n is not 0), A 9 'O-group (a 9' represents the same meaning as where, n is not a 1..), a 9.
  • M a — group ⁇ M a is an R b — group (R b represents a CI-C10 alkyl group optionally substituted with a halogen atom), a halogen atom, a nitro group, a cyano group, a hydroxyl group, R c
  • R a — R d group R e represents a C1-C10 alkyl group which may be substituted with a halogen atom, B a represents an oxy group, a thio tomb, a sulfinyl group or a sulfonyl group; d represents a single bond or a C1-C10 alkylene group.
  • HOR d — group R d represents the same meaning as described above
  • R e —CO— R d — group R e represents hydrogen Represents a C ⁇ C10 alkyl group which may be substituted with an atom or a halogen atom, and R d represents the
  • R e , R e , 'and R e ,' are the same or different, R e , R e , and R e , represent the same meaning as described above, and R e ''' E represents the same C meaning, and R d represents the same meaning as described above.
  • R b -S0 2 NR e — R d — group (where R b , R e and R d have the same meaning as above;), R e R e , N—S 0 2 — R d —Group (R e , R e ′ and R d represent the same meaning as described above), a C2-C10 alkenyl group or a C2-C10 alkyl group.
  • M b One R d — group [M b 0 is M c .
  • One group ⁇ M c . M d . 1 R d , 1 group ⁇ M d 0 is a M a — group (M a represents the same meaning as described above) 6- to 10-membered aryl group, or M a — group (M a, the represent the same meaning as.) in which may be substituted also 5- 10 membered heteroaryl group ring to the, or, M a one group (M a represents the same meaning as above. )
  • (e Q ) — group ⁇ e Q is substituted with a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a 1 N-group (Ri represents the same meaning as described above), a sulfinyl group or a sulfonyl group. May form a 5-12 membered hydrocarbon ring. Represents ⁇ , R d 'are the same or different and R d, it represents the same meaning as R d. ⁇ . ⁇ , M c .
  • One B a — group (M c . And B a represent the same meaning as described above :), M c . 1 CO— group (M c .
  • M c Represents the same meaning as described above
  • One C_ ⁇ one O- group M c. Represents the same meaning as above.
  • M e Q O- CO- group M e., The., Which represents the same meaning as described above
  • M. . R e N— group M e .
  • M c . — One CO—NR e group M c Q and R e represent the same meaning as described above :
  • M c . O—CO—NR e ⁇ group (M c . And R e represent the same meaning as described above;), M e .
  • R e N—CO— group (M c 0 and R e are as defined above), M c .
  • R e N—CO—NR e ′ — group (M c Q , R e and R e ′ have the same meaning as described above), M c .
  • One S0 2 —NR e — group (M c Q and R e are as defined above) or M c .
  • R e N— S0 2 — represents a group (M c .
  • R e represent the same meaning as described above
  • R d represents the same meaning as described above.
  • Z Q group halogen atom, -C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group
  • a 5- to 12-membered hydrocarbon ring or heterocyclic ring which may have a group, which is an aromatic or non-aromatic monocyclic or condensed ring, and a group which is condensed with the A ring
  • Q A. Is a hydroxyl group, (b .;) one group ((b.) Represents the same meaning as described above.)
  • a 9 1 B 6 -B c 1 group [A 9 and B 6 represent the same meaning as above, and B c is an oxy group or 1 N ((O) m R) 1 group (m and Represents the same meaning as described above. However, when A 9 is a hydrogen atom, B c is not a sulfonyl group.
  • a 7, 'one S_ ⁇ 2 - B c - group (A 7' 'and B c represent the same meanings as the above;.), A 8 - S 0 2 -B c one group (A 8 And B c have the same meaning as described above, except that A 8 is not a hydrogen atom :),, N_S0 2 — B c — group, R ′ and B c have the same meaning as above.
  • V. W A 0 is an oxygen atom or — NT A.
  • One group [T A 0 is a hydrogen atom, A 9, one group (A 9 'represents the same meaning as above.), D 5 - R 4 - group (D 5 and R 4 are the same Represents one meaning.) Or Me . Represents one group ( ⁇ . 0 represents the same meaning as described above.)
  • V I. K A Represents a hydrogen atom, a halogen atom or a CI-C10 alkyl group
  • L A Are: • a hydrogen atom, a CI-C10 alkyl group or M b .
  • M b represents the same meaning as described above.
  • C1 - C10 alkylene group or unsubstituted or may C1 in one or the same or different from comprising a plurality of M a group - which may form a C10 alkenylene group.
  • a ring is a benzene ring and W A. Is an oxygen atom, L A. Is a methyl group, K A. In but a hydrogen atom, Q A 0 is CI- C4 alkoxy groups, when the C3- C4 Arukeniruokishi group or C3-C4 al Kiniruokishi group, (! In mosquito SO rather, also in ring A benzene ring, W A.
  • L A. Is a methyl group
  • K A. Is a hydrogen atom
  • Q A 0 is a C ⁇ C4 alkoxy group, a C3-C4 alkenyloxy group, or a C3-C4 alkynyloxy group
  • QL is 1
  • Y A 0 is a halogen atom, or a C1-C4 alkyl group that may be substituted with a halogen atom or a C CC4 alkoxy group, or a nitro group, or a CI-C4 alkoxy group, or RB—group (R is CI—C4 represents an eight-chain alkyl group, and B represents an oxy group or a thio group.
  • A is a benzene ring
  • W A Is an oxygen atom
  • K A Is a 1,3-butylene group, and when Q A 0 is a methoxy group, q is 1, Y A 0 is not a methoxy group or an ethoxy group, A is a benzene ring, and WAQ is an oxygen atom And L A.
  • K A Is 1,3-butylene, and when Q AQ is a hydroxyl group, q is 1 and Y A. Is not an ethoxy group.
  • a fibronectin gene transcription repressing composition comprising a cinnamoyl compound represented by the above and an inert carrier;
  • A represents a benzene ring or a pyridine ring.
  • X A is a substituent on a carbon atom and represents a group included in any one of the following groups A to N, and p is 0, 1, Represents 2, 3, 4 or 5, and when p is 2 or more, X A is the same or different.
  • group ⁇ R 3 is a hydrogen atom or a halogen atom or R 2 -B x one group (R 2 ⁇ And represents the same meaning as described above.
  • M represents 0 or 1
  • B 2 represents a single bond, an oxy group, a thio group, or —N ((O) n R, ') one group (Ri' is the same as or different from Represents the same meaning, n represents 0 or 1.) represents, B 3 represents a force sulfonyl group, a thiocarbonyl group or a sulfonyl group, m, represents 0 or 1, and B 3 represents When it is a sulfonyl group, m is 0 and R 3 is not a hydrogen atom.
  • ⁇ , And k ′ represents 0 or 1.
  • ⁇ And R 4 represents a CI-C10 alkylene group. However, R. , R.
  • R.' and R.,, are the same as or different from R, and have the same meaning as R., and R 4 has the same meaning as described above.) except for.
  • D 3 — R 4 — group ⁇ D 3 represents a nitro group or R x OS0 2 -S (R x represents the same meaning as described above), and R 4 represents the same meaning as described above. Represents. ⁇ Or OS0 2 — group (I ⁇ represents the same meaning as described above).
  • Ei and E; L ′ are not carbonyl groups at the same time.
  • E 2 represents a C2-C10 alkylene group which may be substituted with an oxy group, a thio group, a sulfinyl group, a sulfonyl group or a —NI ⁇ ′ — group (where R ⁇ ′ has the same meaning as described above), Or oxy group, thio group, sulfini , A sulfonyl group, or one NRi '-3 ⁇ 4 ⁇ R 1 ' represents the same meaning as described above. ) Represents a C3-C10 alkenylene group which may be substituted, and ⁇ represents the same meaning as described above. ]
  • G, G 2 , G 4 and G 5 are a methylene group which is bonded to an adjacent atom by a single bond and may be substituted with a methyl group, or Represents a methine group which may be substituted with a methyl group, which is connected to an adjacent atom by a double bond, and G 3 is a single bond, a double bond, or a methyl group, an oxy group, a thio group, a sulfinyl group.
  • NI ⁇ — represents a C2-C10 alkenylene group which may be substituted with a group (1 ⁇ has the same meaning as above), and R 4 has the same meaning as described above.
  • J 2 and J 3 are the same or different and each represents a methine group which may be substituted with a methyl group or a nitrogen atom, and R 4 represents the same meaning as described above.
  • R 5 is not a vinylene group.
  • ⁇ A 3 is a hydrogen atom, or a ⁇ -C10 alkyl group, or a C2-C10 octacylalkyl group, or a C2-C10 alkenyl group that may be substituted with a halogen atom, or a halogen atom.
  • R 4 -S (Di and R 4 represent the same meaning as above:
  • R 2 — B 1 — R 4 — group R 2 , B 1 and R 4 are , D 4 — R 4 — group (D 4 and R 4 represent the same meaning as above:), D 5 — group (D 5 is the same as above) ), — R 4 -S (Di and R 4 represent the same
  • B 4 represents an oxy group, a thio group or one N ((O) m 1 ) one group (1 ⁇ and m represent the same meaning as described above).
  • B 4 is a thio group
  • a 3 is not a hydrogen atom.
  • Group F A 5 — B 5 — R 6 — group
  • a 5 represents D 4 — group (D 4 represents the same meaning as described above), — group represents the same meaning as described above.
  • D 3 represents the same meaning as described above
  • a 4 -S0 2 group (A 4 represents the same meaning as described above) substituted with C2-C10 alkyl Group, or R 2 — — group (R 2 and Represents the same meaning as described above.
  • D 2 — group (D 2 represents the same meaning as described above), D 5 — group (D 5 represents the same meaning as described above) or A 2 — CO— group (A 2 represents Represents a C1-C10 alkyl group substituted with), B 5 represents a — group (Bt represents the same meaning as described above), or a single group ⁇ represents Represents the same meaning.
  • R 6 represents a single bond or a CI-C10 alkylene group.
  • [A 6 is a (a) —R 4 — group (where (a) and R 4 are as defined above), or a C2-C10 alkenyl group, or a C2-C10 alkynyl group, or , Halogen atom, R 2 — — group (R 2 and are the same as defined above:), D 5 — group (D 5 is as defined above), D 2 — group ( D 2 represents the same meaning as described above.) Or A 2 mono-CO— group (A 2 represents the same meaning as described above) or a C2-C10 alkenyl group substituted with a halogen atom, R 2 -B x 1 group (R 2 and are as defined above), D 5 — group (D 5 is as defined above), D 2 — group (D 2 is , Or A 2 — CO— group (A 2 represents the same meaning as described above) or a C2-C10 alkynyl group substituted with (b) — group.
  • a 7 is an optionally substituted C2-C10 alkenyl group, C2 C10 alkynyl group, C3-C10 haloalkynyl group , R 2 — B!
  • R 4 — group (R 2 , B x and R 4 represent the same meaning as described above), D 4 — R 4 — group (D 4 and 4 represent the same meaning as described above) , D 5 — R 4 — group (D 5 and R 4 are as defined above), — R 4 — group (and R 4 are as defined above), (b) — R 4 — group ((b) and R 4 have the same meaning as above.), (C) — R 4 — group ((c) and R 4 have the same meaning as above.) , D 2 -R 4 - group (D 2 and R 4 represent the same meanings.), D 3 - 4 one group, (D 3 and R 4 represent the same meanings as the above.) a 4 - S0 2 -R 4 one group (a 4 and R 4 • the representative of the same meaning as.) or a 2 - C_ ⁇ one R 4 - group (a 2 and R 4 are the same represents represents.) an meanings, B 6 represents a carbonyl group or
  • a 8 -CS-N ((O) n R,)
  • One R 6 — group [A 8 represents a hydrogen atom or a C ⁇ C10 alkyl group optionally substituted with a halogen atom, n, 1 ⁇ and R 6 represent the same meaning as described above. ]
  • a 7 ' is a C3-C10 alkenyl group which may be substituted with a halogen atom, substituted with a halogen atom which may be C3- CIO al Kiniru group
  • R 2 - 1 one R 4 '- group (R 2 and represent the same meaning as above, R 4', represents a C2- C10 alkylene group.
  • — R 4 ′ — group and R 4 ′ have the same meaning as above. Represents the taste.
  • One R 6 — group [A 8 , n, and R 6 represent the same meaning as above, B 3 ' Represents a carbonyl group or a sulfonyl group.
  • a 7 , '-S0 2 -N (( ⁇ ) n R 1 )
  • One R 6 — group [A 7 , is a C2-C10 alkenyl group, a C3-C10 alkenyl group substituted with a halogen atom, C3-C10 alkynyl group, R 2, R 4 , 1 group (R 2 , B, and R 4 , which have the same meanings as described above), D 4 — R 4 '— group (D 4 and R 4 ' represent the same meaning as above), D 5 — R 4 — group (D 5 and; 4 represent the same meaning as described above),- R 4 '-group and R 4 ' represent the same meaning as described above.
  • D 2 —CO— group (D 2 represents the same meaning as above), or A 2 — COCO— group (A 2 represents the same meaning as described above) or A 9 -CO-Bi ′ one R 6 one group (A 9 and R 6 represent the same meaning as described above, and , Represents an oxy group or a thio group, and when B ′ is an oxy group, A 9 is not A 8 ), or A 9 -CS-B, 'one R 6 — group (A 9 , B x 'and R 6 are, the represent the same meaning as), or, a 7.', -S0 2 - 1 '- R 6 - group (a 7,,, 1' and R 6, Represents the same meaning as described above.) Or A 8 — S0 2 — ⁇ ′ — R 6 — group (A 8 , 1 B x ′ and R 6 represent the same meaning as described above.
  • a 8 does not become a hydrogen atom.
  • One R 6 — group (A 9 , B 2 , B 3 B x ′ and R 6 represent the same meaning as described above.) or (b) — group ((b) represents the same meaning as described above.)
  • (c) a C2-C10 alkenyl group substituted with a single group (where (c) represents the same meaning as described above)
  • Group K One N ((0) n ) One CO— R 6 — group [At. Is a hydrogen atom (denotes, n is not 0), A 7 '' one S0 2 — group (A 7 , 'means the same as above), A 8 — S ⁇ 2 — Group (A 8 represents the same meaning as described above, provided that A 8 is not a hydrogen atom), A 9 ′ O— group (A 9 ′ represents the same meaning as described above, provided that n is not 1.), A 9 '— group (A 9 ' represents the same meaning as above.
  • R 2 0CH 2 — group R 2 represents the same meaning as described above •.
  • a 2 CO—R 4 — group A 2 and R 4 represent the same meaning as described above
  • a 2 —CO—CH CH 2 CO—A 2
  • n, R x and R 6 represent the same meaning as described above.
  • N, R x and R 6 represent the same meaning as described above.
  • a 9 , is a hydrogen atom or A 9 , one group (A 9 ' is Represents the same meaning as described above.)
  • R, n, 'and R 6 represent the same meaning as described above.
  • Y A is a substituent on a carbon atom and represents a group of the following X group or Y group, and Q is 0, 1, 2, 3, 4 or 5 P (p represents the same meaning as described above) and Q is 5 or less, Q is 2 or more, Y A is the same or different, and q is 2 or more Two adjacent or different Y A may form a group Z and be condensed with the A ring.
  • Group X M a — group
  • R b represents a C1-C10 alkyl group which may be substituted with a halogen atom
  • a halogen atom a nitro group
  • R c represents a C1-C10 alkyl group which may be substituted with a halogen atom
  • B a An oxy group, a thio group, a sulfinyl group or a sulfonyl group, and R d represents a single bond or a -C10 alkylene group.
  • R e represents the same meaning
  • C_ ⁇ one R d - group (R e is a hydrogen atom or substituted with eight androgenic atoms Represents a C1-C10 alkyl group, and R d represents the same meaning as described above.)
  • R e — CO ⁇ 0-R d — group (R e and R d represent the same meaning as described above)
  • R e O—CO—R d — group R e and R d are as defined above
  • HO—CO—CH ⁇ CH— group R e R e ′ N—R d —Group
  • R e and R e ′ are the same or different, R e represents the same meaning as described above, R e ′ represents the same meaning as R e, and R d represents the same as defined above.
  • R e -C0-NR e '— R d — group R e , e ' and R d have the same meaning as above
  • R b 0-CO-N R e
  • R e R e 'N— CO— R d — group R e , R e ′ and R d represents the same meaning as described above.
  • R e R e 'N— CO— NR e ''one R d one group R e , R e ' and R e '' are the same or different, R e and R e 'represent the same meaning as described above, R e ''represents the same meaning as R e, and R d represents the same meaning as described above.
  • R e R e , NC ( NR e ,,) One NR e , '' One R d
  • M c and R e which represents the same meaning as before SL
  • M c 0- C0-NR e one group (M c and R e. representing the meaning of the same one)
  • M c R e N-CO- group (M c and R e represent the same meaning as above. )
  • M c R e N_C_ ⁇ one NR e 'one group (M c, R e and R e' are.
  • M c R e NC ( NR e,) one NR e ,, One group (M c , R e , R e , and R e ', have the same meaning as above), M c — S ⁇ 2 — NR e — group (M c and R e are , And Represents one meaning of.) Or M c R e N-S0 2 one group (M c ⁇ beauty R e represents a representative.) The same meaning as above, R d represents the same meaning as above . ]
  • Z group: One N C (Y a ) One Y a ′ — group (Y a is a C1-C10 alkyl group optionally substituted with a hydrogen atom or a halogen atom, or CI-C10 Y a 'represents an .oxy group, a thio group, or an imino group that may be substituted with a C1-C10 alkyl group.), One Y b — Y b , -Y b , , One group (Y b and Y b , are the same or different and may be substituted with a methylene group, an oxy group, a thio group, a sulfinyl group, or a CI-C10 alkyl group.
  • Alpha 9 is for water atom, B c is not a sulfonyl group.
  • a 7 '' — S 0 2 — B c — group (A 7 '' and B c represent the same meaning as above), A 8 — S0 2 — B c — group (A 8 and B c represents the same meaning as described above, and A 8 is not a hydrogen atom.
  • R, 'N— S0 2 -B c single group (Ri, R x ' and B c represent the same meaning as above), (b) -S0 2 -B c — group ((b) and B c represents the same meaning as above), a 9 '-B c - . group (Alpha 9, and B c represents the same meaning as above), D 5 -.
  • R 4 _B C _ group ( D 5 , R 4 and B c represent the same meaning as described above :), M c — B 3 — B c — group (M c , B 3 and B c represent the same meaning as described above. ) Or a single M c -B c (
  • W A is an oxygen atom or - NT A - group
  • T A is a hydrogen atom
  • a 9 one group (A 9 'represents the same meaning.)
  • D 5 - R 4 - group D 5 and R 4 have the same meaning as above.
  • T A is a hydrogen atom
  • a 9 '— group (A 9 ' represents the same meaning as described above)
  • D 5 _ R 4 — group (D 5 and R 4 represent the same meaning as described above)
  • M e - group (M e represents represents) the same meaning as before follow..
  • K A represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group
  • L A is a hydrogen atom
  • M b represents the same meaning as above .
  • a ring is a benzene ring
  • W A is an oxygen atom
  • L A is a methyl group
  • K A is a hydrogen atom
  • Q A is a CI-C10 alkoxy group, C3-C10 alkenyloxy group, or C3-
  • a ring is a benzene ring
  • W A is an oxygen atom
  • LA is a methyl group
  • K A is a hydrogen atom
  • Q A is a C1-C10 alkoxy group
  • W A is an oxygen atom
  • L A and K A are 1,3-putagenylene groups
  • Q A is a hydroxyl group or
  • Y A is not a CI-C10 alkoxy group.
  • the “same meaning as described above” in the same symbol between a plurality of substituents means that the plural
  • the substituents of the above are independent of each other and represent the same meaning as described above, and the range of choices of substituents selected among the plurality of substituents is the same, but as long as they are selected within the range, This means that the substituents selected may be the same or different.
  • a fibronectin gene transcription repressing composition characterized by comprising a cinnamoyl compound represented by the formula:
  • A represents a benzene ring or a pyridine ring
  • X a is a substituent on a carbon atom, substituted with a CI-C10 alkyl group substituted with a cyano group, or a tetrahydropyran monoalkylene group.
  • Carboxy group, rr, N—CO— group (r and r are the same or different and represent a hydrogen atom or a CI-CIO alkyl group), — NH—CO— group (is CI-C10 Represents a C2-C10 alkyl group substituted with an alkoxy group, and a′—CO—group ′ represents a morpholino group. ;), Rr 'N— CH 2 — group and! ”' Have the same meaning as above.), R 0-(O)! One CONH— CH 2 — group (r. Is CI-C10 alkyl) 1 represents 0 or 1), r_OCH 2 — group (r represents the same meaning as described above), r.
  • y- CO- NH- group (a 2 represents a C2-C10 alkyl group substituted with a C Bok C10 alkoxy group, y is Okishi group Or rO—C OC ⁇ —NH— group (where r represents the same meaning as described above), or a 3 —z—NH— group (a 3 represents C 2 — C10 alkenyl group Or a C ⁇ C10 alkoxy group, a C1-C10 alkoxycarbonyl group, a C1-C10 alkyl group substituted with a carboxy group or a cyano group, and z represents a strong sulfonyl group or a sulfonyl group.
  • a 4 —NHCO— group ⁇ a 4 is a CI-C10 alkoxy group, or a C3-C10 alkenyloxy group, or r. 1 S0 2 — group (r 0 represents the same meaning as described above) ), Or a C2-C10 alkyl group substituted with a hydroxyl group or a C1-C10 alkoxy group, or r.
  • R D ′ N— group (r. Represents the same meaning as described above, and r 0 ′ Is the same as or different from r. And represents the same meaning as r.) C2-C10 alkyl group substituted by) or rO-CO- group (r represents the same meaning as described above).
  • Y a is a halogen atom, a C1-C10 alkyl group that may be substituted with a halogen atom, or a CI-C10 alkyl group that may be substituted with a CI-C10 alkoxy group, or a C2-C10 alkenyl group Or a C2-C10 alkynyl group, or a 2-oxomonoxazolidine-3-yl group, a [1,3] dioxolane-2-yl group, a CI-C10 alkoxy group substituted with a morpholino group, or A. 'One b' — group (a.
  • b' represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group.
  • r. CO 1 NH— group (r. Represents the same meaning as described above :), r. R. 'NCONH— group (r.
  • r Q are the same as defined above)
  • a hydroxyl group Q represents 0, 1, 2 or 3
  • q When Y is 2 or more, Y a is the same or different, and when Q is 2 or more, adjacent Y a is condensed with ring A to form 2,3-dihydro-benzo [1, 4] rather it may also be without the Jiokishin ring, q a is, r a - O Group ⁇ r a is a hydrogen atom, or, C1-C10 alkyl group, or, C3 - C10 Arukenirire group, or, C3- C10 alkynyl group, or, r Q r, N- CH 2 -..
  • K a is to table a hydrogen atom, a halogen atom or CI- C10 alkyl group
  • L a represents a hydrogen atom or CI- C10 alkyl group
  • K a and L a is C1-C10 alkyl May form a ren group or a 1,3-butenegenylene group.
  • the A ring is a benzene ring
  • W a is oxygen atom
  • L a is a methyl group
  • K a is hydrogen
  • Q a is CI- C10 alkoxy groups
  • the a ring is a benzene ring
  • W a is oxygen atom
  • L a is a methyl group
  • K a is hydrogen
  • Q a is C1-C10 alkoxy group
  • p is Y a is a halogen atom q is 1 at 0, or a halogen atom or CI- C10 alkoxy group CI-C10 alkyl group, or nitro group, or
  • a fibronectin gene transcription repressing composition comprising a cinnamoyl compound represented by the above and an inert carrier;
  • a cinnamoyl compound contained as an active ingredient in the composition according to item 1, 2, 3 or 4 as an active ingredient for suppressing fibronectin gene transcription; 6. Decrease the expression level of fibronectin gene; Use of a cinnamoyl compound contained as an active ingredient in the composition of the preceding paragraph 1, 2, 3 or 4 as an active ingredient to improve tissue fibrosis by leading to a decrease in fibronectin accumulation;
  • a method for treating heart failure comprising administering an effective amount of the composition according to item 1, 2, 3, or 4 to a mammalian patient in need of treatment for treating heart failure; 8. Use of a cinnamoyl compound contained as an active ingredient in the composition according to item 1, 2, 3 or 4 as an active ingredient for treating heart failure;
  • a cinnamoyl compound contained as an active ingredient in the composition according to 1, 2, 3 or 4 above and an inert carrier; a therapeutic agent for heart failure; and
  • a method for treating heart failure comprising administering an effective amount of the therapeutic agent for heart failure described in 9 above to a mammal patient in need of treatment for treating heart failure;
  • the saturated hydrocarbon group in the alkyl group, the haloalkyl group, the alkoxy group, the alkoxy group, the alkylthio group, the alkylsulfinyl group, the alkylsulfonyl group and the alkylene group may be branched. Some or all of the carbon atoms may form a ring, and the unsaturated hydrocarbon group in the alkenyl group, alkenyloxy group, alkynyl group, alkynyloxy group, alkenylene group and alkynylene group may be branched. In addition, some or all of the carbon atoms may form a ring, and the number of unsaturated bonds is one or more.
  • examples of the alkyl group include a methyl group, an ethyl group, an isopropyl group, a cyclohexyl group, and a cyclopropylmethyl group.
  • examples of the haloalkyl group include 2, 2, 2—
  • examples of the alkoxy group include a methoxy group, an ethoxy group, a cyclopentyloxy group, and 2-cyclohexyloxy.
  • examples of the alkylthio group include a methylthio group.
  • examples of the alkylsulfinyl group include a methylsulfinyl group.
  • examples of the alkylsulfonyl group include a methylsulfonyl group.
  • alkylene group examples include a methylene group, an ethylethylene group, 1, 4-cyclohexylene group and the like, and an alkenyl group and Examples of the alkynyl group include vinyl group, 2-propenyl group, 3-methyl-2-butenyl group, 1,3-butenyl group, 3-cyclohexenyl group, and the like.
  • Ethynyl group, 2-propini And alkenylene groups include, for example, vinylene group, probeneylene, 1,3-butenegenylene group and the like
  • alkynylene groups include: For example, ethynylene group, propynylene group and the like can be mentioned.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and a silicon atom.
  • a pyridyl group includes a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group
  • a furyl group includes a 2-furyl group and a 3-furyl group
  • naphthyl group includes 1-naphthyl group and 2-naphthyl group.
  • examples of the leaving group include an alkylsulfonyl group such as a mesoxy group, an arylsulfonyloxy group such as a tosyloxy group, and an alkoxysulfonyl group such as a methoxysulfonyloxy group.
  • examples thereof include a xyl group, for example, a halogen atom such as a bromine atom.
  • the pharmacologically acceptable salt represents a salt of the compounds (I) to (IV) with an inorganic acid, a salt with an organic acid, a salt with an inorganic base, or a salt with an organic base.
  • salts with inorganic acids include hydrochlorides and hydrohalates
  • examples of salts with organic acids include acetates and benzoates
  • salts with inorganic bases include potassium salt and sodium salt.
  • Examples of the salt with an organic base include pyridine salt and morpholine salt.
  • T A o are D 1, D 2 , D 3 , D 4 , D 5 , R 0 , R 0 ', R 0 ', R 1 , R x ','', R 2 , R 2 ′, R 3 , R 4 , R 4 ′, R s , R 6 , A, A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 7 ', A 7 '', A s , A 8 ', A 9 , A 9 ', A 9 ,,, A x o, A x o', A x !, B, B,, B 0,.
  • Y A, Q A, K A, L A and T A are independently of one another, D x, D 2, D 3, D 4, D 5, R 0, R 0 ', R 0 'R x ', R x '
  • R d, R d, R e, R e, R e, B a, B have B c, Y a, Y a ,, Y b, Y b,, Y b ′, Y c and Y e ′ and groups represented by k, k ′, 1, m, m ′, n and n ′.
  • X a , Y a , q a and t a are independently of each other a.
  • 6- to 10-membered aryl group means a group forming a monocyclic or condensed aromatic hydrocarbon ring, such as phenyl group, 1-naphthyl group, 2-naphthyl group, 6 —Indanyl group and the like
  • 5- to 10-membered heteroaryl group means a group that forms a monocyclic or condensed aromatic heterocycle, such as a 2-furyl group or a 3-furyl group.
  • 2-Chenyl group, 3-Chenyl group 2-Pyridyl group A 3-pyridyl group, a 4-pyridyl group, a 2-quinolyl group, etc., and a “3- to 10-membered hydrocarbon ring or heterocyclic group that may contain an unsaturated bond” is a monocycle Or, it includes a fused ring, and includes a 2-cyclohexenyl group, a 2-morpholinyl group, a 4-piperidyl group, etc., and these may be substituted by a single or a plurality of the same or different Ma groups.
  • a group condensed with a ring is a halogen atom, CI-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group And may have one or a plurality of atoms or groups selected from the sulfinyl group or the sulfonyl group.
  • a 5- to 2-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group.
  • a C3-C10 alkenylene group optionally substituted by a group, a sulfonyl group or a single N i ⁇ '— group (I ⁇ ' represents the same meaning as described above) means that one or more carbon atoms are , Oxy group, thio group, sulfinyl group, sulfonyl group One NR
  • Good C2-C10 alkenylene group means carbon One or more child may be substituted with a methyl group, or, one or 'more of the carbon atoms, Okishi group, Chiomoto , Sulfinyl group, sulfonyl group or mono-group has the same meaning as described above.
  • groups belonging to the group are shown in Table 22, Table 23 and Table 24 below.
  • ⁇ ⁇ of the compound ( ⁇ ). ⁇ which can take. Group, B Q group, C Q group, D Q group, E Q group, F 0 group, G. Group, H. Group, I. Group, J. Group, K. Group, L. Group, MQ group and N.
  • the groups belonging to the groups are shown in Table 1, Table 2, Table 3, Table 4, Table 5 to 7, Table 8 to 11, Table 12 to 14, Table 15, Table 16, Table 17, and Table 18, respectively. Examples are shown in Table 19, Table 20 and Table 21, Y A. Possible X Q group, Y. Swarm and eagle.
  • the groups belonging to the group are illustrated in Table 22, Table 23 and Table 24 below, respectively Q Q and T. Are shown in Table 25 to Table 26 and Table 27 below, respectively.
  • Groups and groups belonging to Group A to Group N are illustrated in Tables A to N below.
  • groups capable of geometric isomerism all geometric isomers are meant and tautomerism is possible.
  • tautomers thereof are meant.
  • Table 1 shows the groups belonging to the group and group A.
  • Table 3 shows the groups belonging to the group and group C. Table 3
  • Tables 8 to 11 show examples of groups belonging to the F 0 group and the F group.
  • Table 16 shows the groups belonging to the I o group and the I group.
  • Table 17 shows the groups belonging to J o group and J group. 1 7 ..
  • Table 18 shows the groups belonging to group and group K.
  • Table 20 shows the groups belonging to the group and the group M.
  • Table 21 The groups belonging to the group and group N are illustrated in Table 21.
  • Table 2 1 The groups belonging to the group and group N are illustrated in Table 21.
  • the methine group has no substituent.
  • Q a is a hydroxyl group that may be substituted.
  • the cinnamoyl compound shown by these is mention
  • the cinnamoyl compound (II ′) when X is a methine group, the methine group has no substituent.
  • Q A Is a combination of a hydroxyl group, an A 9 '— 0_ group (A 9 ' represents the same meaning as described above), or an M c — 0- group (M c represents the same meaning as described above). Can be given.
  • A, X A, Y A , p, q, Q A and W A represent the same meaning as above, x is, it represents a methine group or a nitrogen atom.
  • the cinnamoyl compound shown by these is mention
  • the methine group has no substituent.
  • Q A is a hydroxyl group
  • Q A is a hydroxyl group, an A 9 ′ —0— group (A 9 ′ represents the same meaning as described above), or an M c — 0— group (M Tavern Represents the same meaning as described above.)
  • a 9 ′ represents the same meaning as described above
  • X one group of X A is in F group, I group or K group. Represents the substituent to which it belongs.
  • the compounds (I) as a typical example of the compound (V)
  • WO 97/35565 publication, JP 09227547 publication, WO 00/2037 1 publication, JP 2002371078 publication, WO 01/79187 publication and WO 92/18483 publication have compounds having a certain conceptual skeleton. Although disclosed, this document does not describe the effect of suppressing transcription of extracellular matrix genes in tissues, and hence the effect of suppressing the amount of extracellular matrix accumulation.
  • Compound (I) for example, formula (shed) (wherein, Alpha, chi alpha, 'a compound Upsilon alpha, is ⁇ and Q representing. Defined above and same) represented by the formula (alpha') (wherein, H kappa alpha and L a represent.
  • Compound (II) is represented, for example, by the formula (AO) (wherein A, X A , Y A , p and q represent the same meaning as described above). And a compound represented by the formula (AO ′) (wherein Q A. , W A 0, K AQ and L AQ have the same meanings as described above) are reacted in the same manner as described above. Can be manufactured.
  • Compound (III) includes, for example, a compound represented by formula (A) (wherein A, X A , Y A , p and Q have the same meanings as described above), and a compound represented by formula ( ⁇ ′) (Wherein Q A , W A , K A and L A represent the same meaning as described above) and can be produced by reacting in the same manner as described above.
  • Compound (IV) is represented, for example, by the formula (a) (wherein A, X a ,' Y a , p and Q have the same meaning as described above).
  • a compound represented by the formula (a ') (wherein, Q a, W a, the K a and L a represent. the same meaning as above) and a compound represented by', are reacted in the same manner as described above And can be manufactured.
  • X b represents a MeOCH 2 C 0— NH— group or a Me 0 CH 2 CH 2 NH— CO 1 group.
  • X b ′ ′ represents one Me SCH 2 CH 2 O group, one H0CH 2 CH 2 OCH 2 group or one NC—CH 2 CH 2 group.
  • the benzaldehyde derivative or 6-formyl-2-[(2-methoxyethyl) aminocarbonyl] pyridine represented by the above formula is a new substance with no examples reported so far.
  • the benzaldehyde derivative is, for example, the formula (XXIX-a)
  • the reaction temperature is usually from room temperature to the solvent reflux temperature, and the reaction time is usually from instantaneous to about 24 hours.
  • the reaction is usually carried out in the presence of a base.
  • the base used include organic bases such as pyridine, trytylamine, N, N-dimethylaniline, triptylamin, N-methylmorpholine, sodium hydroxide, water.
  • inorganic bases such as potassium oxide and potassium carbonate.
  • the amount of the reagent used in the reaction is usually 1 to 2 mol for daricin methyl ester and 1 to 7 mol for the base, relative to 1 mol of compound ( ⁇ -a).
  • solvents that can be used for the reaction include aliphatic hydrocarbons such as hexane and petroleum ether, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as chloroform, dichloroethane, and jetyl ether.
  • Ethers such as dioxane and tetrahydrofuran, ketones such as acetone and methylethyl ketone, esters such as ethyl acetate and jetyl carbonate, nitriles such as acetonitrile and isobutylnitryl, amides such as formamide and N, N-dimethylformamide And sulfur compounds such as dimethyl sulfoxide or a mixture thereof.
  • the reaction solution is subjected to usual post-treatments such as organic solvent extraction, water washing, and concentration of the organic layer under reduced pressure. If necessary, the reaction solution is purified by operations such as chromatography and recrystallization.
  • the benzaldehyde derivative can be obtained by manufacturing.
  • the benzaldehyde derivative is, for example, the formula ⁇ -b) (XXIX-b)
  • the compound represented by the formula (XXIX-b) is, for example, the formula (XXIX-c)
  • reaction can be performed in the same manner as the reaction of (XXIX-a) with glycine methyl ester.
  • benzaldehyde derivative is represented by, for example, the formula (XXIX-d) (XXIX-
  • the compound (XXIX-d) is publicly known, for example, described in documents such as J. Medicina 1Chem. (2 0 0 1), 4 4, 3 62.
  • 6-formyl-2-[(2-methoxyethyl) aminocarbonyl] pyridine has the formula ( ⁇ -e)
  • Compound (XXIX-e) can be produced by reacting 2-strength loxy-6-formylpyridine with a chlorinating agent such as phosphoryl chloride, thionyl chloride or trisyl chloride.
  • a chlorinating agent such as phosphoryl chloride, thionyl chloride or trisyl chloride.
  • the reaction temperature is usually from room temperature to the solvent reflux temperature, and the reaction time is usually from instantaneous to about 24 hours.
  • the amount of the reagent used for the reaction is usually 1 to 10 moles of the chlorinating agent with respect to 1 mole of 2-carboxy-6-formylpyridine.
  • a solvent is not always necessary, but it is usually carried out in the presence of a solvent.
  • Solvents that can be used in the reaction include aliphatic hydrocarbons such as hexane and petroleum ether, aromatic hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as chloroform and dichloroethane, and jetyl. Examples thereof include ethers such as ether, dioxane and tetrahydrofuran, or a mixture thereof.
  • Compounds (I) to (IV) have the ability to suppress the transcription of the fibronectin gene . This ability is important for improving tissue fibrosis by decreasing the expression level of fibronectin gene and leading to a decrease in the accumulation amount of extracellular matrix such as fibronectin. Therefore, compounds (I) to (IV) are compositions (pharmaceuticals) for reducing tissue fibrosis by reducing the amount of fibronectin gene expression and reducing the amount of fibronectin and other extracellular matrix accumulated. , Cosmetics, food additives, etc.).
  • the diseases to which the transcriptional repressive composition of the present invention can be applied include, for example, diseases in which the tissue becomes fibrotic due to excessive accumulation of fibronectin, resulting in a decrease in the function of tissues such as organs, resulting in scar formation. (That is, fibrosis, etc.).
  • diseases in which the tissue becomes fibrotic due to excessive accumulation of fibronectin resulting in a decrease in the function of tissues such as organs, resulting in scar formation.
  • fibrosis etc.
  • chronic vaginitis skills gastric cancer, asthma, myocardial fibrosis, heart failure, restenosis after PTCA, myelofibrosis, rheumatoid arthritis, atopic dermatitis, hypertrophic scar, uterine fibroid, prostate hypertrophy Alzheimer's disease, sclerosing peritonitis, diabetic retinopathy and the like.
  • the active ingredient of the transcriptional repression composition of the present invention is a composition for inhibiting fibronectin synthesis promotion by TGF- / 3 to suppress tissue fibrosis and obtaining a fibrosis treatment effect (medicine, cosmetics, food additives) Etc.) can be used as active ingredients.
  • Such a transcription repressing composition of the present invention comprises compounds (I) to (IV) and an inert carrier.
  • the compounds (I) to (IV) contained in these compositions are usually from 0.01 to 99.9% by weight, and the inert carrier is usually 99.99%. % By weight to 0.01% by weight.
  • the inert carrier is a pharmaceutically acceptable carrier or excipient, and the transcription-suppressing composition of the present invention may further contain a pharmaceutical additive, a cosmetic additive, a food additive and the like.
  • Pharmaceutically acceptable carriers, excipients, pharmaceutical additives, food additives, cosmetic additives, and the like used in the composition can be appropriately selected depending on the specific use of the composition. .
  • the form of the composition can be, for example, various solids, liquids, etc., depending on the specific application.
  • compounds (I) to (IV) when compounds (I) to (IV) are used as active ingredients of pharmaceuticals, specific forms such as powders, fine granules, granules, tablets, syrups, capsules, suspensions, etc. Oral agents such as turbidity agents, emulsions, extracts and pills, transdermal absorption agents such as injections, external liquids and ointments, and parenteral agents such as suppositories and topical agents.
  • Oral preparations include, for example, gelatin, sodium alginate, starch, corn starch, sucrose, lactose, glucose, mannitol, carboxymethylcellulose, dextrin, polyvinylpyrrolidone, crystalline cellulose, soy lecithin, sucrose, fatty acid ester, evening milk , Magnesium stearate, Polyethylene glycol, Magnesium silicate, Anhydrous silicate, etc. It can be produced in accordance with ordinary methods using pharmaceutical additives such as perfumes, stabilizers, moisturizers, preservatives, antioxidants and the like.
  • the dose varies depending on the age, sex, weight, disease level of the mammal to be administered, the type of composition of the present invention, the dosage form, etc.
  • the amount of the active ingredient is about 1 mg to about 2 g, preferably the amount of the active ingredient is about 5 mg to about 1 g.
  • the daily dose can be administered once or divided into several times. '
  • injections are water-soluble solvents such as physiological saline and sterile water Ringer's solution, water-insoluble solvents such as vegetable oil and fatty acid esters, isotonic agents such as glucose and sodium chloride, and dissolution aids. It can be produced according to ordinary methods using pharmaceutical additives such as stabilizers, preservatives, suspending agents and emulsifiers. Liquid preparations for external use, percutaneous absorption agents such as gel ointments, suppositories for rectal administration and the like can also be produced according to conventional methods. In order to administer such a parenteral preparation, injection (subcutaneous, intravenous, etc.), transdermal administration, or rectal administration may be used.
  • the topical agent can be produced, for example, by incorporating the compounds (I) to (IV) into a pellet of a sustained release polymer such as an ethylene vinyl acetate polymer. This pellet may be surgically implanted into the tissue to be treated.
  • the dose varies depending on the age, sex, weight, disease level of the mammal to be administered, the type of the composition of the present invention, the form of administration, etc. About 0.1 mg to about 50 O mg may be administered. In addition, the daily dose can be administered once or divided into several times.
  • compositions (I) to (IV) When compounds (I) to (IV) are added to cosmetics, the compound is added.
  • the cosmetics include liquid, milky, cream, lotion, ointment, gel, aerosol, mousse and the like.
  • Lotions can be produced according to conventional methods using, for example, cosmetic additives such as suspension agents, milk pills, preservatives and the like.
  • the dose varies depending on the age, sex, weight, disease level, type of composition of the present invention, dosage form, etc. of the mammal to be administered. About 5 Omg should be administered. In addition, the above-mentioned daily dose can be administered once or divided into several times.
  • specific forms of foods to which the additives are added include, for example, powders, tablets, beverages, ingestible gels or syrups.
  • Liquid products such as seasonings, Japanese confectionery, Western confectionery, ice confectionery, beverages, sprays, pastes, pickles, canned bottles, processed meat products, processed fish products, processed milk products, processed egg products, processed vegetable products, General foods and beverages such as processed fruit products and processed cereal products, and favorite foods can be listed. It can also be added to feed and feed for domestic animals, poultry, bees, cormorants, fish and other domestic animals.
  • the dose varies depending on the age, sex, weight, disease level of the mammal to be administered, the type of composition of the present invention, the dosage form, etc., but is generally about 0. About 50 Omg should be administered.
  • the above-mentioned daily dose can be administered once or divided into several times.
  • Reference Example 1 Reference Example 1 From 1 to 1 to 1 24, benzaldehyde derivatives (a) to (p), (r) to), and 6-formyl-2-[(2-methoxyethyl) aminocarbonyl] pyridine ( Describe the synthesis of Q).
  • Reference Example 1-1 1 Synthesis of benzaldehyde derivative [Compound No. (a)]
  • 3-Aminobenzil alcohol 12.31 g, tetrahydr b-furan 160 ml and g
  • a solution of 11.42 g of methoxyacetyl chloride in 40 ml of tetrahydrofuran was added at 10 ° C.
  • insoluble matters were filtered off, the filtrate was concentrated under reduced pressure, and the resulting residue was dissolved in 200 ml of ethyl acetate.
  • the organic layer was washed with water, dilute hydrochloric acid and saturated brine in that order, dried over anhydrous magnesium sulfate, and concentrated.
  • a catalytic amount of iodine was added to a mixture of 0.67 g of magnesium and 10 ml of tetrahydrofuran, and a solution of 6.0 g of bromo-3_ (2,2-difluoroethenyl) benzene in 20 ml of tetrahydrofuran was added dropwise at 55 ° C. After stirring at room temperature for 15 minutes, a solution of 3.98 g of 1-formylpiperidine in 5 ml of tetrahydrofuran was added dropwise. The mixture was heated for 15 minutes under reflux, ice water and 10% hydrochloric acid were added, and the mixture was extracted with butyl methyl ether.
  • 4-Hydroxy-3 is the same as Reference Example a-1 except that 3-[(methanesulfonyl) aminocarbonyl] benzaldehyde 0. ⁇ 5 g was used instead of 3-[(methoxycarbonyl) methoxy] benzaldehyde.

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pulmonology (AREA)
  • Dermatology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Ophthalmology & Optometry (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention décrit une préparation d'inhibiteur de transcription du gène de la fibronectine ou une préparation similaire, caractérisée en ce qu'elle contient un composé de type cinnamoyle de formule (I) ci-dessous ainsi qu'un vecteur inerte. (I)
PCT/JP2006/304531 2005-03-02 2006-03-02 Emploi d'un composé de type cinnamoyle WO2006093336A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2005-057365 2005-03-02
JP2005057365A JP2006241045A (ja) 2005-03-02 2005-03-02 シンナモイル化合物の用途

Publications (1)

Publication Number Publication Date
WO2006093336A1 true WO2006093336A1 (fr) 2006-09-08

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PCT/JP2006/304531 WO2006093336A1 (fr) 2005-03-02 2006-03-02 Emploi d'un composé de type cinnamoyle

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JP (1) JP2006241045A (fr)
WO (1) WO2006093336A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007132948A1 (fr) * 2006-05-17 2007-11-22 Sumitomo Chemical Company, Limited Composé de cinnamoyle et leur utilisation
WO2007132945A1 (fr) * 2006-05-17 2007-11-22 Sumitomo Chemical Company, Limited Composé de type cinnamoyle et leur utilisation
WO2007136125A1 (fr) * 2006-05-22 2007-11-29 Sumitomo Chemical Company, Limited Composé ayant un noyau hétérocyclique et son utilisation

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004123620A (ja) * 2002-10-03 2004-04-22 Sumitomo Chem Co Ltd ４−ヒドロキシ−１−ベンゾピラン−２−オン化合物及びその利用
JP2004123621A (ja) * 2002-10-03 2004-04-22 Sumitomo Chem Co Ltd ４−メトキシ−１−ベンゾピラン−２−オン化合物及びその利用
JP2004175780A (ja) * 2002-03-27 2004-06-24 Sumitomo Chem Co Ltd ２−ピロン化合物およびその用途
WO2005028441A1 (fr) * 2003-09-17 2005-03-31 Sumitomo Chemical Company, Limited Derives de cinnamoyle et utilisation de ceux-ci
WO2005028439A1 (fr) * 2003-09-17 2005-03-31 Sumitomo Chemical Company, Limited Compose de cinnamoyle et utilisation de ce compose
WO2005028463A1 (fr) * 2003-09-17 2005-03-31 Sumitomo Chemical Company, Limited Compose cinnamoyle et utilisation associee

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004175780A (ja) * 2002-03-27 2004-06-24 Sumitomo Chem Co Ltd ２−ピロン化合物およびその用途
JP2004123620A (ja) * 2002-10-03 2004-04-22 Sumitomo Chem Co Ltd ４−ヒドロキシ−１−ベンゾピラン−２−オン化合物及びその利用
JP2004123621A (ja) * 2002-10-03 2004-04-22 Sumitomo Chem Co Ltd ４−メトキシ−１−ベンゾピラン−２−オン化合物及びその利用
WO2005028441A1 (fr) * 2003-09-17 2005-03-31 Sumitomo Chemical Company, Limited Derives de cinnamoyle et utilisation de ceux-ci
WO2005028439A1 (fr) * 2003-09-17 2005-03-31 Sumitomo Chemical Company, Limited Compose de cinnamoyle et utilisation de ce compose
WO2005028463A1 (fr) * 2003-09-17 2005-03-31 Sumitomo Chemical Company, Limited Compose cinnamoyle et utilisation associee

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007132948A1 (fr) * 2006-05-17 2007-11-22 Sumitomo Chemical Company, Limited Composé de cinnamoyle et leur utilisation
WO2007132945A1 (fr) * 2006-05-17 2007-11-22 Sumitomo Chemical Company, Limited Composé de type cinnamoyle et leur utilisation
WO2007136125A1 (fr) * 2006-05-22 2007-11-29 Sumitomo Chemical Company, Limited Composé ayant un noyau hétérocyclique et son utilisation

Also Published As

Publication number Publication date
JP2006241045A (ja) 2006-09-14

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