WO2006093339A1 - シンナモイル化合物の用途 - Google Patents
シンナモイル化合物の用途 Download PDFInfo
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- WO2006093339A1 WO2006093339A1 PCT/JP2006/304539 JP2006304539W WO2006093339A1 WO 2006093339 A1 WO2006093339 A1 WO 2006093339A1 JP 2006304539 W JP2006304539 W JP 2006304539W WO 2006093339 A1 WO2006093339 A1 WO 2006093339A1
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- 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
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- 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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- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—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
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/02—1,2-Thiazines; Hydrogenated 1,2-thiazines
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Definitions
- the present invention relates to uses of cinnamoyl compounds.
- Cirrhosis chronic vaginitis, Skills gastric cancer, interstitial lung disease, asthma, chronic obstructive pulmonary disease, glomerulonephritis, lupus nephritis, tubulointerstitial nephritis, IgA nephropathy, nephrosclerosis, diabetic nephropathy Hereditary kidney disease, myocardial fibrosis, heart failure, restenosis after PTCA, arteriosclerosis, myelofibrosis, rheumatoid arthritis, post-inflammation hyperplasia, postoperative scar, burn scar, atopic dermatitis In hypertrophic scars, uterine fibroids, benign prostatic hyperplasia, scleroderma, Alzheimer's disease, sclerosing peritonitis, diabetic retinopathy, type I diabetes, excessive extracellular matrix such as collagen and fibronectin Accumulation causes the tissue to become fibrotic and hardened, resulting in a decrease in
- TGF-3 a kind of site force-in
- Ding 0-3 has been shown to increase the expression level of extracellular matrix genes and to be involved in the enhancement of extracellular matrix protein production and, in turn, tissue fibrosis (J. I nv est. D e rma tol., 94, 365, (1 9 9 0); La b. I nvest., 6 3, 1 7 1, (1 9 9 0)).
- tissue fibrosis model animals improves tissue fibrosis and accompanying improvements in tissue function.
- hypertension organ fibrosis is one of the causes of heart failure such as left ventricular diastolic dysfunction and renal failure such as diabetic nephropathy and nephrosclerosis.
- agents that improve the fibrosis of tissues by decreasing the amount of extracellular matrix gene expression in the tissue and decreasing the amount of extracellular matrix accumulation ie, extracellular matrix accumulation inhibitors and fibrosis therapeutic agents
- the development of a therapeutic agent for heart failure ie, extracellular matrix accumulation inhibitors and fibrosis therapeutic agents.
- the present invention relates to the use of compounds represented by the following formulas (I) to (V), (1 ′), ( ⁇ ′) and (V), which have the ability to suppress transcription of extracellular matrix genes. That is, the present invention
- A represents a benzene ring or a pyridine ring
- ⁇ ⁇ is a substituent on the carbon atom, Group or eagle.
- M a is an R b — group (R b represents a CI-C10 alkyl group which may be substituted with a halogen atom), halogen atom, nitro group, cyan Group, hydroxyl group, R c 1 B a — R d — group (R c represents a C1-C10 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 sulfo group.
- R 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 a C1-C10 alkyl group that may be substituted with a hydrogen atom or a halogen atom, and R d has the same meaning as described above.
- HO — C ⁇ — CH CH— group, R e R e , N_R d — group (R e and R e 'are the same or different, R e has the same meaning as described above, R e ' has the same meaning as R e , R d represents the same meaning as described above.)
- R b — S 0 2 -NR e 1 R d — group (R b , R e and R d are as defined above;), R e R e 'N— S0 2 — R d— represents a group (R e , R e and R d have the same meaning as described above), a C2-C10 alkenyl group or a C2-C10 alkynyl group.
- M b Q — R d — group [M b 0 is a group of M c 0 ⁇ M c . M d . — R d ' ⁇ group ⁇ M d . May be substituted with a M a — group (M a represents the same meaning as described above), or a 6-10-membered aryl group or a M a — group (M a is the same as defined above).
- the 5- to 10-membered heteroaryl group which may be substituted with) or the M a — group (M a has the same meaning as defined above), and the unsaturated group which may be substituted with 3 A group that forms a 10-membered hydrocarbon ring or heterocyclic ring that may contain a bond, or
- G. represents an optionally substituted, saturated, non-aromatic, 5-14 membered hydrocarbon ring or heterocyclic ring.
- 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.
- ⁇ Forming a 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group.
- R d ' are the same or different and R d, it represents the same meaning as R d. ⁇ . ⁇ , M c .
- R e represent the same meaning as above.
- M c. R e N— C 0 — NR e '— group (M c , R e and R e ' represent the same meaning as described above)
- M c 0 R e NC ( NR e ') — NR e “—Group (M c , R e , R e , and R e ” represents the same meaning as described above;)
- One S0 2 — NR e — group (M c 0 and Re represent the same meaning as described above) or M c 0 R e N-S0 2 one group (M c, and Re are the same as defined above)
- R d represents the same meaning as described above.
- halogen atom CI-CIO 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 ⁇ ring is there.
- Q a represents an optionally substituted hydroxyl group or an optionally substituted amino group.
- W a is (are T alpha, hydrogen atom, or represents.
- a location substituent on the nitrogen atom) oxygen atom or one NT a _ group represents a.
- T alpha represents the same meaning as, L B represents a hydroxyl group or a methyl group.
- T a represents the same meaning as, L Y represents CI- C10 alkyl group.
- T alpha represents the same meaning, the kappa beta, Shiano group or UOCO- group (U represents. A hydrogen atom or a C1-C10 alkyl group);. ]
- W a represents the same meaning as described above, and ⁇ ⁇ and L 8 may have a substituent or a 3-C10 alkylene group or a substituent. Forms an alkenylene group.
- T a represents the same meaning as, Q B represents a hydroxyl group which may be substituted.
- An extracellular matrix gene transcription repressing composition comprising a cinnamoyl compound represented by the formula (1) and an inert carrier;
- I. ⁇ represents a benzene ring or a pyridine ring
- ⁇ ⁇ is a substituent on the carbon atom, Group or eagle.
- ⁇ ⁇ 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, ⁇ ⁇ is the same or different, and ⁇ and Q The sum is 5 or less.
- M a is R b — group (R b represents a C1-C10 alkyl group which may be substituted with a halogen atom), halogen atom, nitro group, cyano group, hydroxyl group, R c -B a one R d — group (R c represents a C1-C10 alkyl group which may be substituted with a halogen atom, B a represents an oxy group, a thio group, a sulfier group or a sulfonyl group; R, represents a single bond or CI- C10 alkylene group), H_ ⁇ _R d -.
- R E represents a hydrogen atom or a C1-C10 alkyl group optionally substituted with a halogen atom
- R D represents the same meaning as described above.
- R E — CO— O— R D — group R E and R D have the same meaning as above
- R E 0_C ⁇ — R D — group R E and R D are Represents the same meaning as above.
- H 0 1 C 0 1 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 R E
- R D represents the same meaning as described above.
- R B O—CO—N E ) — R D — a group (R B , R e, and R D are ), R E R E , N—CO—R D — group (where R E , R E , and R D represent the same meaning as above), R E R E 'N—C O—NR E “
- R E represents the same meaning as R E, and R D represents the same meaning as described above.
- R B - represents the same meaning as described R E, R D represents the same meaning
- R E R E 'N-S0 2 i R D — group R E , R E ' and R D are the same meanings as described above
- M B Q— R D — group [M B. M C. —Group ⁇ M C. M D. — R D ' ⁇ group ⁇ M D. May be substituted with a M A — group (M A represents the same meaning as described above). 6—10-membered aryl group or M A — group (M A is the same as above. ) Which may be substituted with 5- to 10-membered heteroaryl group or M A — group (M A represents the same meaning as described above) and unsaturated which may be substituted with 3 A group that forms a 10-membered hydrocarbon ring or heterocyclic ring that may contain a bond, or
- G. represents a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent.
- Ri is a hydrogen atom, or a CI-C10 alkyl group, or a halogen atom, or an 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).
- a C2-C10 alkyl group, or a C3-C10 alkenyl group, or a C3-C10 alkynyl group is represented.
- ⁇ Forming a 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group.
- R e N—CO—NR e ′ (M c , R e and R e ′ represent 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 Q and R e represent the same meaning as described above), and R d represents the same meaning as described above. ] (3) Z.
- Halogen atom C ⁇ C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfur group or sulfonyl group It may be a 5- to 12-membered hydrocarbon ring or heterocyclic ring, which is an aromatic or non-aromatic monocyclic or condensed ring, and is a group that is condensed with the ⁇ ring. .
- 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 —NT a — group ( ⁇ ⁇ represents a hydrogen atom or a substituent on a nitrogen atom).
- T alpha represents the same meaning as, L B represents a hydroxyl group or a methyl group.
- T alpha represents the same meaning as described above.
- ⁇ represents the same meaning as described above, and ⁇ represents a cyano group or a UO CO— group (U represents a hydrogen atom or a CI—C10 alkyl group). ]
- W a represents the same meaning as described above, and ⁇ and L 8 each may have a C 3 -C 10 alkylene group which may have a substituent or a C 4 to C 10 which may have a substituent.
- ⁇ and L 8 each may have a C 3 -C 10 alkylene group which may have a substituent or a C 4 to C 10 which may have a substituent.
- T a represents the same meaning as above, Q B is o representing a hydroxyl group which may be substituted]
- I. AO represents a benzene ring or a pyridine ring.
- X AQ is a substituent on a carbon atom, N from the group. Represents a group included in any group up to the group, p represents 0, 1, 2, 3, 4 or 5, and when p is 2 or more, X A. Are the same or different.
- a group 0 : — R 4 — group is — (O) k —) Eight N— ( ⁇ ) k '— group is a hydrogen atom, CI-C10 alkyl group, halogen atom, or R
- R 2 represents a CI-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group
- B t represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group.
- R represents an optionally substituted CI-C10 alkyl group, or a C2-C10 alkenyl group, or a C2-C10 alkynyl group; Represents a hydrogen atom, a C1-C10 alkyl group or a C2-C10 haloalkyl group, m represents 0 or 1, B 2 represents a single bond, an oxy group, a thio group or —N ((O) n R) — Represents a group (Ri ′ is the same as or different from, and represents the same meaning as, n represents 0 or 1), B 3 represents a carbonyl group, a thiocarbonyl group, or a sulfonyl group, m ′ represents 0 or 1, and when 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 C1-C10 alkylene group.
- R. 'R. “N—R 4 — group (R., and R.” is the same as or different from R. and represents the same meaning as R. R 4 represents the same meaning as described above.)
- N C (—O R 2 ) — 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 ⁇ S ⁇ 2 — group (I ⁇ represents the same meaning as described above), and R 4 represents the same meaning as described above. Represents. ⁇ Or OS ⁇ 2 — group (where R ⁇ has the same meaning as above).
- E. represents an optionally substituted, saturated or unsaturated, aromatic or non-aromatic 5- to 14-membered hydrocarbon ring or heterocyclic ring, It represents the same meaning as above.
- CO_R 4 - (O) n -N C (R 3) one group ⁇ Ri, R 4, n And R 3 represents the same meaning as described above, and B Q represents an oxy group, a thio group, or _N ((O) m R x ') — group (I ⁇ ' and m represent the same meaning as described above).
- G. may have a substituent, a saturated or unsaturated, non-aromatic, 5-14 membered hydrocarbon ring or heterocyclic ring.
- J. may contain a nitrogen atom, forms an aromatic 5- to 7-membered ring
- R 4 represents the same meaning as described above.
- a halogen atom R 2 -B x _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 R 4 represent the same meaning as described above), D 5 — group (D 5 represents the same meaning as described above), — R 4 — group and R 4 represent the same meaning as described above.
- D 2 — group (D 2 represents the same meaning as described above) or D 3 — R 4 — group (D 3 and R 4 represent the same meaning as described above) substituted with C2 -C10 alkynyl group
- R 5 is not a vinylene group.
- ⁇ A 3 is a hydrogen atom, 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 4 ) m group
- R a represents an optionally substituted 5- to 7-membered aryl group or heteroaryl group, and R 4 and m have the same meanings as described above
- a 4 — S ⁇ 2 — R 4 — group ⁇ A 4 is (b.) Single group ((b.) Represents the same meaning as described above.), (C.) Single group ((c Q ) represents the same meaning as described above.) Or R, 'N-group and, represent the same meaning as described above. R 4 represents the same meaning as described above.
- ⁇ Represents a CI-C10 alkyl group substituted with
- B 4 represents an oxy group, a thio group, or —N ((O) m 1 ⁇ ) — group and m have the same meaning as described above. ). However, when B 4 is a thio group, A 3 is not a hydrogen atom. ⁇ ,
- R 5 represents a C2-C10 alkenylene group which may be substituted with a halogen atom, or And C2-C10 alkynylene group.
- a 5 — B 5 — R 6 — group [A 5 represents a 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 _S 0 2 — group (A 4 represents the same meaning as described above) substituted with C2-C10 An alkyl group, or a group of R 2 -B x (R 2 and are as defined above), D 2 — group (D 2 is as defined above), D 5 — A group (D 5 represents the same meaning as described above) or an A 2 -CO 1 group (A 2 represents the same meaning as described above) substituted with a CI-C10 alkyl group.
- B 5 represents a — group (B represents the same meaning as described above) or a single — group (A 1 represents the same meaning as described above), and R 6 represents a single bond or C1- Represents a C10 alkylene group.
- a 5 represents
- [A 6 is a (a Q ) — R 4 — group ((a Q ) and R 4 are as defined above.), Or a C2-C10 alkenyl group, or a C2-C10 alkynyl group, Or a halogen atom, R 2 -B x 1 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 — CO— group (A 2 represents the same meaning as described above) substituted with a C 2 -C 10 alkenyl 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 single group (D 2 Represents the same meaning as described above.) Or a C 2 -C 10 alkynyl group substituted with an A 2 —CO— group (A 2 represents the same meaning as described above), or (b.) —
- D 2 — N (— ( ⁇ ) n -A x ) — R 6 — group (D 2 , n, A, and R 6 have the same meaning as above), D 2 — group (D 2 Represents the same meaning as described above, except for the cyan group;), '( ⁇ ) n ) N-CR X " N—R 6 —group (I ⁇ , R, n and R 6 are It represents the same meaning as above, and the shaku "" is the same as or different from, and represents the same meaning as.;), — ( ⁇ ) n — , NR 2 — R 6 — group (Ri, n, Ri, R 2 and R 6 represent the same meaning as described above.
- R 2 — B 3 —NR X —CO—NRi, —R 6 — group (R 2 , B 3 ,, and R 6 have the same meaning as above), D 2 —CO—NR x 1 R 6 — group (D 2 , R x and R 6 are as defined above) or A 2 —COCO—NRi —R 6 1 group (A 2 , R x and R 6 are Represents the same meaning as
- a 7 is an optionally substituted C2-C10 alkenyl group, C2-C10 alkynyl group, C3-C10 haloalkynyl.
- B 6 represents a force sulfonyl group or a thiocarbonyl group
- n, R, and R 6 represent the same meaning as described above.
- a 8 represents a hydrogen atom or a C1-C10 alkyl group optionally substituted with a halogen atom
- n, R 1 and R 6 represent the same meaning as described above.
- One R 6 — group [A 7 ' is an optionally substituted C3-C10 alkenyl group, substituted with a halogen atom which may be C3-C10 alkynyl group, R 2 - 1 - R 4 , one group, (R 2 and B represents the same meaning as above, R 4, represents a C2- C10 alkylene group.)
- B 3 , n, R, and R 6 represent the same meaning as described above.
- a 8 ,-B 2 '-CS-N ((O) n R,) — R 6 -group [A 8 represents a CI-CIO alkyl group or a C2-CIO haloalkyl group, and B 2 ' represents And the same meaning as described above, and n and R 6 represent the same meaning as described above.
- a 8 ', n, R ⁇ and R 6 represent the same meaning as above, and B 3 represents a carbonyl group or a sulfonyl group.
- a 7 " is a C2- CIO alkenyl group, a C3- C10 alkenyl group substituted with a halogen atom, a halogen atom optionally substituted C3-C10 alkynyl group, R 2 -B, - R 4 '- group (R 2, B, and R 4'.
- a 9 CS-8 '-R 6 — group (A 9 ,' and R 6 represent the same meaning as above), or A 7 "— S ⁇ 2 -B 1 , — R 6 — group (A 7 ′′, 1 , and R 6 represent the same meaning as described above.)
- a 8 -S0 2 -B 1 '-R 6 — group (A 8 , B 1 ′ and R 6 represent the same meaning as described above, except that A 8 cannot be a hydrogen atom.)
- a 9 , —B 2 ′ — B 3 — ′ — R 6 — group (A 9 ′, B 2 , B 3 , B 1 , and R 6 represent the same meaning as described above.)
- One group ((b.) Is , Or (c.)
- a single group ((c.) Represents the same meaning as described above.) It has been C2- C10 alkenyl group
- R 2 OCH 2 single group R 2 is represents the same meaning as
- a 2 -. C_ ⁇ one R 4 -. group (a 2 and R 4 are the representative of the same meaning as) or a 2 -CO-CH (CH 2 CO- A 2 ) represents one group (A 2 represents the same meaning as described above), and n, 1 ⁇ and R 6 represent the same meaning as described above.
- R 2 —CO— group R 2 has the same meaning as above)
- a 2 —CO—R 4 — group A 2 and R 4 are as defined above
- a 2 —CO—CH CH 2 CO—A 2
- a 2 represents the same meaning as described above
- n, R, and R 6 represent the same meaning as described above.
- N, and R 6 represent the same meaning as described above.
- N 0 group: ⁇ — P ( 0) (ORi ') — R 4 — group [ ⁇ ⁇ is — group (Ri represents the same meaning as above), O— R 6 — group And R 6 represent the same meaning as described above. ) Or OCO—CHR Q — group and R Q represent the same meaning as described above. ) And 'and R 4 represent the same meaning as described above. ]
- Y A. Is a substituent on a carbon atom
- X below.
- Group and Y. Represents a group of groups, Q represents 0, 1, 2, 3, 4 or 5, p (p represents the same meaning as described above) and Q is 5 or less, Q is Y A when 2 or greater. Are the same or different, and when Q is 2 or more, two adjacent Y A that are the same or different.
- Z. It may be condensed with the AO ring as a group.
- 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 e — B a — R ri group R c represents a CI-C10 alkyl group which may be substituted with a halogen atom
- B a represents an oxy group, a thio group, a sulfiel group or a sulfonyl group
- R d represents a single bond or a CI-C10 alkylene group.
- R d represents the same meaning as described above
- R e — CO— R d — group R e may be replaced by a hydrogen atom or a halogen atom
- R d represents the same meaning as described above
- R e —CO—O—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 have the same meaning as above), HO—C O — CH ⁇ CH— group, R e R e 'N— R d —Group (R e and R e are the same or different, R e has the same meaning as above, R e ′ has the same meaning as R e, and R d is the same as above.
- R e -CO-NR e 'one R d — group R e , R e ' and R d have the same meaning as above
- R b O-CO-N R e
- R e R e 'N— CO— R d — group R e , R e 'And R d have the same meaning as above
- R e R e ' N—CO—NR e "-R d — group R e , R e 'and R e " are the same or R e and R e ′ have the same meaning as described above
- R e ′′ represents the same meaning as R e
- R d represents the same meaning as described above;
- R e R e , N—C ( NR e ") — NR e "'— R d — group (R e , R e e , R e ' and R d have the same meaning as above)
- M b 0 R d — group [M b o is M c . —The group ⁇ M c o is M d .
- One R d '— group ⁇ M d 0 is a single M a group (M a represents the same meaning as described above) 6- to 10-membered aryl group, or M a — A 5- to 10-membered heteroaryl group which may be substituted with a group (M a represents the same meaning as described above), or a M a — group (M a has the same meaning as described above).
- M c Q and R e represent the same meaning.
- M c Q R e N- C0-NR e '- group M c Q, R e and R e , represents the same meaning as above.
- M c Q, R e and R e represents the same meaning as above.
- Halogen atom C1-C10 alkoxy group, C3-C10 alkenyloxy group, C3-C10 alkynyloxy group, carbonyl group, thiocarbonyl group, oxy group, thio group, sulfinyl group or sulfonyl group
- Q A. Is a hydroxyl group, (b.) One group ((b Q ) represents the same meaning as described above.), A 9 — B 6 — B c — group [A 9 and B 6 have the same meaning as described above. B c represents an oxy group or one N (( ⁇ ) m ) — group (m and represent the same meaning as described above). However, when A 9 is a hydrogen atom, B c is not a sulfonyl group.
- a 7 "— S ⁇ 2 -B c — group (A 7 ” and B c have the same meaning as above;), A 8 — S ⁇ 2 -B c — group (A 8 and B c represents the same meaning as above, except that A 8 is not a hydrogen atom.), R, N—S 0 2 — B c — group (Ri,, and B c are the same as above ), (B.) 1 S0 2 -B c 1 group ((b.) And B c are Represents the same meaning as above.
- a 9 , 1 B e — group ( ⁇ 9 ′ and B c are as defined above), D 5 — R 4 -B c — group (D 5 , R 4 and B c are Represents the same meaning as described above.), M c . -B 3 — B c — group (M c , B 3 and B c have the same meaning as described above) or M c . 1 B c to group (M c Q and B c represent the same meaning as described above).
- T AQ represents the same meaning as described above, and L B. Represents a hydroxyl group or a methyl group.
- T A Represents the same meaning as described above, and K B. Represents a cyano group or a UOCO— group (U represents a hydrogen atom or a CI—C10 alkyl group). ]
- 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 of the following groups A to N, p is 0, It represents 1, 2, 3, 4 or 5, and when p is 2 or more, X A is the same or different.
- Group A -R 4 group is-(O) k one) A, N- (O) k 'group (R t is a hydrogen atom or CI-C10 alkyl group or halogen Atom or R 2 —B x — group (R 2 represents a CI-CIO alkyl group, a C3-CIO alkenyl group, or a C3-CIO alkynyl group, represents an oxy group, a thio group, a sulfiel group, or a sulfonyl group.) in substituted C2- C10 alkyl group, or, C3- C10 alkenyl group, or represents a C3- C10 ⁇ Rukiniru group, k represents 0 or 1, k is, R 3 - (.
- m - (B 2 -B 3) m ' - groups ⁇ R 3 is a hydrogen atom or a halogen atom or an R 2 - group (.
- R 2 and may represent the same meanings as the above) may be substituted with CI -Represents a C10 alkyl group, or a C2-C10 alkenyl group, or a C2-C10 alkynyl group, R Q represents a hydrogen atom, a C1-C10 alkyl group, or a C2-C10 haloalkyl group, and m is 0 or 1 and B 2 is a single bond, an oxy group, a thio group or one N ((O) n ) — group (I ⁇ 'is the same as or different from R 1 and has the same meaning as N represents 0 or 1.
- B 3 represents a carbonyl group, a thiocarbonyl group or a sulfonyl group, m 'represents 0 or 1, and B 3 represents a sulfonyl group.
- R 3 cannot be a hydrogen atom.
- ⁇ , And k ′ represents 0 or 1.
- ⁇ And R 4 represents a C ⁇ C10 alkylene group.
- R. , R Q “N—R 4 — group (R., and R.” is the same as or different from R. and represents the same meaning as R Q, and R 4 represents the same meaning as described above. ) except for.
- [In (a), E! And E! 'Is a C1-C10 alkyl group or CI-C10 alkoxy Represents a methylene group which may be substituted with a group, or a strong phenyl group. However, £ e and Ee cannot be a carbonyl group at the same time.
- E 2 represents an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or one or one group 'has the same meaning as described above.
- C2-C10 alkylene group which may be substituted with, or an oxy group, a thio group, a sulfinyl group, a sulfonyl group or one NI ⁇ , one group 'has the same meaning as described above.
- R 4 - ( ⁇ ) n -N C (R 3 ) - group, R 4, n and R 3 represent the same meanings as above, B.
- ⁇ , D 2 1 R 4 — (0) n -N C (R 3 ) 1 group (D 2 , R 4 , n and R 3 represent the same meaning as above) or
- N— N C (R 3 ) — represents a group (e, A 1 and R 3 represent the same meaning as described above).
- AN—O— R 4 — group (Ri, A, and R 4 have the same meaning as above.), (Ai-(O) n one) N— group (I ⁇ , A 1 and n Represents the same meaning as described above), D 2 — group (D 2 represents the same meaning as described above) or D 3 — group (D 3 represents the same meaning as described above).
- Substituted C2-C10 alkenyl group (Ri, A, and R 4 have the same meaning as above.), (Ai-(O) n one) N— group (I ⁇ , A 1 and n Represents the same meaning as described above), D 2 — group (D 2 represents the same meaning as described above) or D 3 — group (D 3 represents the same meaning as described above).
- R 4 — group [In (b), G 2 , G 4 and G 5 are single bonds with adjacent atoms.
- G 3 is a single bond Or a double bond or a methyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or a ⁇ ⁇ — group (1 ⁇ represents the same meaning as described above).
- (In (c),] 1 ] 2 and] 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 has the same meaning as described above. ), Halogen atom, R 2 -B x — R 4 — group (where R 2 , B 1 and R 4 have the same meaning as above), D 4 — R 4 — group (D 4 and R 4 represents the same meaning as described above.), D 5 — group (D 5 represents the same meaning as described above), — R 4 — group, and R 4 represent the same meaning as described above. ), A D 2 _ group (D 2 represents the same meaning as described above) or a D 3 — R 4 — group (D 3 and R 4 represent the same meaning as described above). C2-C10 alkynyl group
- R 5 is not a vinylene group.
- ⁇ A 3 is a hydrogen atom, a CI-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.
- C3-C10 alkynyl group or R a- (R 4 ) m mono group R a is substituted with a halogen atom, a C1-C10 alkyl group, a C1-C10 alkoxy group or a nitro group.
- R 4 and m represent the same meaning as described above.
- R 4 and m represent the same meaning as described above.
- R 2 — — R 4 — group (R 2 , ⁇ ⁇ and R 4 represent the same meaning as above)
- D 4 — R 4 — group (D 4 and R 4 represents the same meaning as above)
- D 5 -. group (D 5 represents the same meaning as above)
- -. R 4 -. group E and R 4 are the same meaning Represents.
- B 4 represents an oxy group, a thio group, or a single group of N ((O) m R,) (1 ⁇ and m represent the same meaning as described above). However, when B 4 is a thio group, A 3 is not a hydrogen atom. ⁇ ,
- Rx — B 4 — CO— R 4 — B 4 '— group (I ⁇ , B 4 and R 4 have the same meaning as above, and ⁇ 4 ' is the same as or different from ⁇ 4. represent the same meaning as beta 4 provided that when beta 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 is And the same meaning as above.
- R 5 represents a C2-C10 alkenylene group which may be substituted with a halogen atom, or C2-C10 represents an alkynylene group.
- Group F A 5 — B 5 —R 6 single group [A 5 represents D 4 — group (D 4 represents the same meaning as described above), — group represents the same meaning as described above Represents. ), D 3 — group (D 3 Represents the same meaning as described above.
- a 4 —S ⁇ 2 — group (A 4 represents the same meaning as described above) or a C2-C10 alkyl group substituted with R 2 — — group (R 2 and ), 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 — Represents a CI-C10 alkyl group substituted with a group (A 2 represents the same meaning as described above), and B 5 represents a B — group represented the same meaning as described above. ) Or —NAi— group (Yawata represents the same meaning as described above), and R 6 represents a single bond or a CI—C10 alkylene group. ]
- [A 6 represents (a) — R 4 — group ((a) and R 4 represent the same meaning as described above), or C2-C10 alkenyl group, or C2-C10 alkynyl group, or Halogen atom, R 2 monogroup (R 2 and are as defined above), D 5 — group (D 5 is
- a D 2 — group (D 2 represents the same meaning as described above) or an A 2 — CO— group (A 2 represents the same meaning as described above) substituted with a C2-C10 alkenyl Group, or halogen atom, R 2 — group (R 2 and are as defined above), D 5 _ group (D 5 is as defined above), D 2 _ A C2-C10 alkynyl group substituted with a group (D 2 represents the same meaning as described above) or an A 2 —CO— group (A 2 represents the same meaning as defined above), or (b ) — Group ((b) represents the same meaning as described above), (c) one group ((c) represents the same meaning as described above;), D 4 — group (D 4 represents The same meaning as described above is represented :), — The group represents the same meaning as described above.
- 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).
- — Group has the same meaning as described above.
- 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 have the same meaning as described above.
- [A 7 is an optionally substituted C2-C10 alkenyl group, C2-C10 alkynyl group, C3-C10 haloalkynyl group , R 2 -B x 1 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 R 4 represent the above and ), D 5 — R 4 — group (D 5 and R 4 are as defined above), — R 4 — group (0 and R 4 are the same as above) ), (B) — R 4 — group ((b) and R 4 represent the same meaning as above), (c) — R 4 — group ((c) and R 4 are ), D 2 — R 4 — group (D 2 and R 4 represent the same meaning as above;), D 3 — R 4 single group (D 3 and R 4 represents the same meaning as), a 4
- a 7 is substituted with a halogen atom
- R 2 — R 4 one group (R 2 and are the same as defined above, R 4 , represents a C2-C10 alkylene group)
- (c) — R 4 , — group ((c) and R 4 ′ have the same meaning as described above.)
- ⁇ ′ is the same as or different from ⁇ and represents the same meaning as ⁇ ,, represents the same meaning as described above.
- B 3 , n, R, and R 6 are the same as described above.
- a 8 ' represents a C ⁇ C10 alkyl group or a C2-C10 eight-necked alkyl group
- B 2 ′ represents the same meaning as described above
- n, R 1 and R 6 represent the same meaning as described above.
- a 7 " is a C2-CIO alkenyl group, a C3-C10 alkenyl group substituted with a halogen atom, a halogen which may be substituted C3-C10 alkynyl group in atom, R 2 ⁇ , one R 4 '- group (R 2,: 6 1 and 1 4'. is representing the same meaning as above), D 4 - R 4 '- group (D 4 and R 4' represents the same meaning.), D 5 _R 4 - group (. D 5 and R 4 represent the same meaning as described above), D t - R 4 '—.
- R 4 ' represent the same meaning as described above. ),. (B) - R 4 '- group ((b) and R 4', wherein the same meaning as Table to), (c) one R 4, one group ((c) and R 4, the And 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 Or A 2 — CO— R 4 — group (A 2 and R 4 represent the same meaning as described above), and n, R 1 and R 6 represent the same as defined above. Represents meaning. ]
- Group K — N (( ⁇ ) n R,) — CO— R 6 — group [Yawata. Is a hydrogen atom (where n is not 0), A 7 "— S0 2 — group (A 7 ” represents the same meaning as above), A 8 — S0 2 — group (A 8 Represents the same meaning as described above, provided that A 8 is not a hydrogen atom.), A 9 , O 1 group ( ⁇ 9 ′ represents the same meaning as described above. ⁇ and ⁇ is 1 ), ⁇ 9 '— group ( ⁇ 9 , represents the same meaning as above.
- R 2 OCH 2 single group R 2 Represents the same meaning as described above.
- a 2 — C ⁇ 1 R 4 — group A 2 and R 4 represent the same meaning as described above
- a 2 —CO—CH CH 2 C0—A 2 ) — group
- n, and R 6 represent the same meaning as described above.
- R 2 — CO— group R 2 is Represents the same meaning
- 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
- one group A 2 represents the same meaning as described above
- n, R x 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 above) and q is 5 or less, and when q is 2 or more, Y A is the same or different and Q is 2 or more When two adjacent or identical Y A are , Z group may be fused with the A ring.
- M a is an R b — group (R b represents a CI-C10 alkyl group which may be substituted with a halogen atom), halogen atom, nitro group, cyan A group, R e — B a one R d — group (R c represents a C1-C10 alkyl group which may be substituted with a halogen atom, and B a represents an oxy group, a thio group, a sulfiel group or a sulfo group.
- R d represents a single bond or a CI-C10 alkylene group)), HO—R 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 CI-C10 alkyl group optionally substituted with a halogen atom, R d represents the same meaning as described above), R e — CO— O— R d - group (R e and R d represent the same meaning.), R e ⁇ _CO- R d - radical (.
- H_ ⁇ - CO- CH CH- group, R e R e, N R d - group (R e and R e, is, unlike the same or different, R e represents the same meaning as, R e 'represents the same meaning as R e, R d, the ), R e — CO— NR e ′ — R d — group (R e , R e ′ and R d have the same meaning as above), R b O—CO— N (R e) _R d - group (R b, R e and R d represent the same meaning.), R e R e ' N- C_ ⁇ one R d - group (R e, R e , And R d represent the same meaning as described above.) R e R e 'N-CO-NR e "-R d — group (R e , R e ' and R e
- M a representing the same meaning as) which may be substituted with phenyl group
- M a - group (M a, the represent the same meaning as) which may be substituted with a pyridyl group, M a -.
- group (M a represents the same meaning as described above.)
- a naphthyl group which may be substituted with (B) — group ((b) represents the same meaning as above;), (c) — group ((c) represents the same meaning as described above),
- (e) - group (. 1 and B b are representing the same meaning as above) it represents, R d 'are different from R d and same or different, represent the same meaning as R d. ⁇ . ⁇ , M c — B a — group (M c and B a represent the same meaning as described above), M c — C 0 group (M c represents the same meaning as described above), M c - CO- O- group (. M c is representative of the same meaning as), M c 0_C_ ⁇ one group (. M e is representative of the same meaning as above;), M c R e N - group (M c and R e represent the same meaning.), M e - CO- NR e - group (.
- M c and R e which represents the same meaning as above
- M c 0_C ⁇ _NR e - group (. M c and R e, wherein represents the same meaning as)
- M c R e N-C_ ⁇ one group (M c and R e represent the same meaning as above.
- Group (M c and R e represent a representative) the same meaning as above, R d is a representative] the same meaning as above. is there.
- Y C -OY C '— ⁇ — group Y C and Y C are the same or different,
- Q A is a hydroxyl group, (b) — group ((b) represents the same meaning as described above), A 9 and B 6 -B c — group [A 9 and B 6 are B c represents an oxy group or —N ((O) m 1 ⁇ ) _ group (m and represent the same meaning as described above).
- a 9 is a hydrogen atom
- B e is not a sulfonyl group.
- B c _ group (D 5, R 4 and B c are representative of the same meaning as above), M c - B 3 - B c - groups (M c, B 3 and B e are the same meaning and.) or M c - B c - groups (M c and B c are the same meaning as above Represents).
- 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 as above.), D 5 _R 4 - group (D s and R 4 are the represent the same meaning as.) or M e - group (M e represents the same meaning as above.) represents the. ].
- T A is a hydrogen atom, ⁇ 9 '— group ( ⁇ 9 ′ represents the same meaning as described above), D 5 and R 4 — group (D 5 and R 4 represent the same meaning as described above) .) or M e - group (M c represents a represents) the same meaning as above..
- L R represents a hydroxyl group or a methyl group.
- T Alpha represents the same meaning as, L r represents CI- C10 alkyl group.
- T A represents the same meaning as described above, and K B represents a cyano group or a UOCO1 group (U represents a hydrogen atom or a CI-C10 alkyl group). ]
- T A represents the same meaning as described above, Q B represents a hydroxyl group, A 9 — B 6 — O— group, and A 9 and B 6 represent the same meaning as described above.
- a 7 “— S ⁇ 2 — ⁇ ⁇ ⁇ (A 7 ” represents the same meaning as described above), A 8 — S ⁇ 2 — 0— group (A 8 represents the same meaning as described above) However, A 8 is not a hydrogen atom.), 1 ⁇ 1 ⁇ 'N— S ⁇ 2 — ⁇ — group (R x and' represent the same meaning as above.), (B) — S0 2 — 0_ group ((b) represents the same meaning as above.), A 9 , 101 groups ( ⁇ 9 ′ represents the same meaning as above;), — R 4 — ⁇ One group (Ds and R 4 have the same meaning as above.)
- M c one B 3 _0- group (M c and B 3, the. Represents the same meaning as) or M o one group (M e represents. The same meanings as the above) represents a. ]
- “representing the same meaning as described above” in the same symbol between a plurality of substituents indicates that the plurality of substituents represent the same meaning as described above while being independent of each other.
- the range of choices of substituents selected is the same among groups, but as long as it is selected within the range, the selected substituents may be the same or different. . ]
- I. a represents a benzene ring or a pyridine ring
- X a is a substituent on a carbon atom, a C1-C10 alkyl group substituted with a cyano group, or a tetrahydropyran-4 monoylidene group CI-C10 alkyl group, or a C2-C10 alkenyl group substituted with a halogen atom or a cyano group, or a C2-C10 alkenyl group substituted with a C1-C10 alkoxycarbonyl group, or a hydroxy group A substituted C3-C10 alkynyl group or a. - ⁇ ⁇ -b- r, '-3 ⁇ 4 ⁇ a.
- r 2 represents a C1-C10 alkyl group substituted with a CI-C10 alkyl group or a hydroxyl group
- r 2 represents a C1-C10 alkyl group substituted with a CI-C10 alkyl group or a hydroxyl group
- a carboxy group 1 ", 1 ⁇ -(: ⁇ -group ( r and r ′ are the same or different and each represents a hydrogen atom or a C ⁇ C10 alkyl group;)
- — NH—CO— group represents a C2-C10 alkyl group substituted with a C ⁇ C10 alkoxy group
- A′—C ⁇ — group represents a morpholino group)
- r 2 represents a C1-C10 alkyl group substituted with a C1-C10 alkylsulfinyl group, a methyl group substituted with a C1-C10 alkylsulfonyl group, a C2-C10 alken
- r represents a C Bok CIO alkyl group, 1 represents 0 or 1..
- r one OCH 2 - group (r, the a One meaning.)
- R. One CO- group (r Q, said. Representing the same meaning as) represents a Shiano group or sulfomethyl group
- r represents the 'C1-C10 alkylene group
- ri represents a single bond or a CI-C10 alkylene group
- b represents an oxy group, a thio group, a sulfier group, a sulfonyl group, or Represents an imino group.
- a 2 —y—CO—NH— group (a 2 represents a C2-C10 alkyl group substituted with a CI-C10 alkoxy group, and y represents an oxy group or an imino group).
- r ⁇ COCO—NH— group (where r represents the same meaning as described above) or a 3 — z_NH— group (a 3 represents a C2-C10 alkenyl group or CI-C10 alkoxy Group represents a C1-C10 alkoxycarbonyl group, a C1-C10 alkyl group substituted with a strong lpoxy group or a cyano group, and z represents a sulphonyl group or a sulfonyl group.)
- a 4 NHCO— Group ⁇ a 4 is a C1-C10 alkoxy group, or a C3-C10 alkenyloxy group, or r.
- a 5 — NHS 0 2 — group (a 5 + represents a C2-C10 alkyl group substituted with a CI—C10 alkoxy group), or r Q 0 N ⁇ CH— group (r. Represents the same meaning as described above.)
- r Q NHCSNH— group (where r represents the same meaning as described above) or r.
- NHC (—S r. ') N— group (r. And r 0 ' represent the same meaning as described above.)
- Y a is a halogen atom, or 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-oxo-oxazolidin-1-yl group, or a [1,3] dioxolan_2-yl group, where the sentence is a CI-C10 alkoxy group substituted with a morpholino group Or a 0 , one b′— group (a.
- b ′ represents an oxy group, a thio group, a sulfinyl group or a sulfo group.
- a nitro group, a cyano group, or an rO-CO mono group (r represents the same meaning as described above), or r. r. , N— group (r. And r 0 ' Represents the same meaning as described above. ), Or r. CO—NH— group (where r represents the same meaning as described above) or r Q r. , NCONH— group (r. And r.
- Q a is, r a _0_ group ⁇ r a is a hydrogen atom, or, C WINCH C10 alkyl group, also, C3- C10 alkenyl group, or, C3- C10 alkynyl group, or, r. r Q , N—CH 2 group (r 0 and r. 'represents the same meaning as described above.), rOCH 2 — group (r represents the same meaning as described above.), r Q — CO— group (r.
- a C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or a cyano group, or r 3 — I ⁇ — group (wherein r 3 represents a phenyl group or a pyridyl group, represents the same meaning as described above).
- r 4 and r 4 ' are the same or different and are a hydrogen atom, CI-C10 alkyl group, or Represents a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a CI-C10 alkoxy group, but does not simultaneously become a hydrogen atom.
- W a represents an oxygen atom or a single NT a - group [T a is r b - group (.
- T a represents the same meaning as above, L b represents a hydroxyl group or a methyl group.
- T a represents the same meaning as, L c represents CI- C10 alkyl group.
- T a represents the same meaning as above.
- T a represents the same meaning
- K b is Shiano group or U_ ⁇ CO represents a hydrogen atom or CI- C10 alkyl group. ) ]
- K r and L ri represent a C3-C10 alkylene group or Forms a C4-CIO alkenylene group.
- T a represents the same meaning as described above
- Q b represents a r a — 0— group (where r a represents the same meaning as described above).
- A represents a benzene ring or a pyridine ring
- X a represents a C1-C10 alkyl group substituted with a cyano group with a substituent on a carbon atom, or tetrahydropyran-4-ylidene.
- An alkynyl group, r 2 O—CO— group (r 2 represents a CI—C10 alkyl group or a C2-C10 alkyl group substituted with a hydroxyl group), a carboxy group, r r′N—CO— group (r and r 'are the same or different, represent a hydrogen atom or a C Bok C10 alkyl group), a t -.
- NH- CO- group (& E is substituted with C Bok C10 alkoxy group C2- C10 alkyl group ), A′—CO— group (a ′ represents a morpholino group), rr, N_CH 2 —group (1 ′′ and 1 ′′ ′ represent the same meaning as described above), r . _ (O)! —CONH—CH 2 — group (r.
- a 2 — y— CO— NH— group (a 2 represents a C2-C10 alkyl group substituted with a CI-CIO alkoxy group, and y represents an oxy group or an imino group).
- rO_COCO—NH— group (r represents the same meaning as described above), or a 3 — z—NH— group (a 3 represents a C2-C10 alkenyl group, or C ⁇ A C10 alkoxy group, a C1-C10 alkoxycarbonyl group, a C1-C10 alkyl group substituted with a strong alkoxy group or a cyano group, and z represents a strong sulfonyl group or a sulfonyl group.
- ⁇ a 4 is a C ⁇ C10 alkoxy group, or a C3-C10 alkenyloxy group, or r. 1 S0 2 — group (where r. Represents the same meaning as described above), or a C2-C10 alkyl group substituted with a hydroxyl group or a CI-C10 alkoxy group, or r. r.
- a C2-C10 alkyl group substituted with 'N 1 group (where r. Represents the same meaning as above, r.' Is the same as or different from r.
- rO—CO— group (where r represents the same meaning as described above), a cyan group or an aminocarbonyl group CI-CIO alkyl group or rO—CO— (rO—C0CH 2 ) CH— group (wherein r represents the same meaning as described above).
- ⁇ Or a 5 — NHS 0 2 — group (a 5 represents a C2-C10 alkyl group substituted with a CI-C10 alkoxy group), or r.
- ON CH— group (wherein r represents the same meaning as described above), or r.
- NHCSNH— group (r. Represents the same meaning as described above), or r.
- Y a is a halogen atom, or 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 C1-C10 alkoxy group, or a C2-C10 alkenyl group, Or a C2-C10 alkynyl group, or a 2-oxo-oxazolidin-3-yl group, or a [1,3] dioxolan-2-yl group, or a C ⁇ C10 alkoxy group substituted with a morpholino group Or a.
- a.' represents a C1-C10 alkyl group which may be substituted with a halogen atom
- Or nitro group, or cyano group, or rO-CO mono group (r represents the same meaning as described above), or r. r. 'N— group (r. And r 0 ' have the same meaning as described above.)
- Or r Q CO—NH— group (r. Represents the same meaning as described above.), Or r. r 0 'NCONH— group (r.
- r.' represents the same meaning as described above.
- r r'NCO— group (1 "and]: 'represents the same meaning as described above. ), Or represents a hydroxyl group, q represents 0, 1, 2, or 3, and when Q is 2 or more, Y a is the same or different, and when Q is 2 or more, they are adjacent Y a may be condensed with the a ring to form a 2,3-dihydro-benzo [1,4] dioxin ring.]
- Q a is r a - 0- group ⁇ r a is a hydrogen atom, or, CI- C10 alkyl group, or, C3- C10 alkenyl group, or, C3-C10 alkynyl group, or, r . r Q 'N— CH 2 — Group (r. And r. 'Represents the same meaning as described above.), R ⁇ CH 2 — group (r represents the same meaning as above), r Q — CO— group (r Q represents the same meaning as described above.
- r 4 r 4 'N— group (where r 4 and r 4 ' are the same or different, a hydrogen atom, or a C1-C10 alkyl group, or Represents a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a CI-C10 alkoxy group, and does not simultaneously become a hydrogen atom.
- W a represents an oxygen atom or - NT a - group
- T a is r b - group (r b is r unlike a same or different meanings same r a of.) or r 3 '- group (r 3 'is different from r 3 identical or different and represent. the same meaning as r 3) represents a.
- one group (V a, V a V a " and V a"' are the same or different
- a methine group or — N group
- T a represents the same meaning as above, L b represents a hydroxyl group or a methyl group.
- L c represents a CI-C10 alkyl group.
- T a represents the same meaning as above.
- T a represents the same meaning as described above, and K b represents a cyano group or a UOCO— group (U represents a hydrogen atom or a C1-C10 alkyl group). ]
- W a represents the same meaning as described above, and K c and L d form a C3-C10 alkylene group or a C4-C10 alkenylene group.
- T a represents the same meaning as described above
- Q b represents a ra — 0— group (where a represents the same meaning as described above).
- T a and L b represents the same meaning as above.
- T a and L c represent the same meaning as described above.
- T a represents the same meaning as above.
- r represents a hydrogen atom or a C1-C10 alkyl group
- the compound represented by formula (VIII-2) is produced by 3-oxopropylylamidation
- r is hydrogen or a C1-C10 alkyl group
- one group (V a, V a , V a , and V a , "are the same or different and represent a methine group or one N group
- I. ⁇ represents a benzene ring or a pyridine ring, and in ( ⁇ ⁇ ) q , ⁇ ⁇ is a carbon atom A substituent on the child, X below.
- Group or Y. Represents a group of groups, Q represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, ⁇ ⁇ is the same or different, and when Q is 2 or more, they are adjacent Two identical or different ⁇ ⁇ is ⁇ . It may form a group and may be condensed with an ⁇ ring.
- ⁇ ⁇ is the following X.
- ⁇ Swarm and eagle.
- M a is R b — group (R b represents a CI-C10 alkyl group which may be substituted with a halogen atom), halogen atom, nitro group, cyan group, hydroxyl group, R c 1 B a — R d — group (R c represents a C ⁇ C10 alkyl group which may be substituted with a halogen atom, and B a represents an oxy group, a .thio group, a sulfiel group or a sulfo group.
- R d represents a single bond or a CI-C10 alkylene group.
- HOR d — group (R d represents the same meaning as described above)
- R e — CO— R d — group (R e is Represents a C1-C10 alkyl group which may be substituted with a hydrogen atom or a halogen atom, and R d has the same meaning as described above.)
- R e — CO— ⁇ — R d — group (R e and R d represent the same meaning as described above.)
- R e O 1 CO—R d — group (R e and R d represent the same meaning as described above)
- HO—CO— CH CH_ group, R e R e, N-R d - group (R e and R e 'are the same or different phase, R e represents the same meaning as, R e' represents the same meaning as R e, R d represents the same meaning as described above.), R
- R b S ⁇ 2 — NR e — R d — group (R b , R e and R d have the same meaning as above), R e R e , N_S0 2 — R d — group (R e , R e , and R d are This means the same meaning as above. ) Represents a C2-C10 alkenyl group or a C2-C10 alkynyl group.
- M b Q — R d — group [M b o is M c o — group ⁇ M c . M d .
- One R d ' ⁇ group ⁇ M d . May be substituted with a M a — group (M a represents the same meaning as described above) 6- to 10-membered aryl group or a M a — group (M a is the same as defined above)
- G Q forms a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent.
- M c represents the same meaning as described above
- M c . _C_ ⁇ - O- group represents the same meaning as.
- M e. 0—CO— group represents the same meaning as described above
- M c . R e N— group M c . And R e represent the same meaning as described above;
- One CO-NR e — group M c . And R e have the same meaning as described above), M c .
- 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 sulfonyl 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 - group (T alpha denotes a hydrogen atom or a location substituent on the nitrogen atom.) Represents the.
- T alpha represents the same meaning as, L B represents a hydroxyl group or a methyl group.
- T a represents the same meaning as, L Y represents CI- C10 alkyl group.
- ⁇ represents the same meaning as described above, and ⁇ represents a cyano group or a UOCO— group (U represents a hydrogen atom or a C1-C10 alkyl group).
- W a represents the same meaning as described above, and ⁇ and L 8 each may have a C 3 -C 10 alkylene group which may have a substituent or a C 4 to C 10 which may have a substituent.
- ⁇ and L 8 each may have a C 3 -C 10 alkylene group which may have a substituent or a C 4 to C 10 which may have a substituent.
- T a represents the same meaning as, Q B is a group represented by represents a hydroxyl group which may be substituted, or,
- An extracellular matrix gene transcription repressing composition comprising a cinnamoyl compound represented by the formula (1) and an inert carrier;
- Ct represents a benzene ring or a pyridine ring
- Y a is a substituent on the carbon atom, Group or eagle.
- Q represents 0, 1, 2, 3, 4 or 5, when q is 2 or more, Y a are the same or different, when Q is 2 or more, adjacent
- Two identical or different ⁇ ⁇ is Z. It may be condensed with a ring as a group, and in (X a ) p , X a is the following X. Group, Y.
- Z represents a substituent on a carbon atom not belonging to the group Q , p represents 0, 1, 2, 3, 4 or 5, and when p is 2 or more, X a is the same or different, P And the sum of Q is 5 or less.
- 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, B a represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group; R d represents a single bond or CI- C10 alkylene group), H_ ⁇ _R d -.
- R d the Represents the same meaning as
- R E — C ⁇ _R D — group R E represents a hydrogen atom or a C1-C10 alkyl group which may be substituted with a halogen atom, R D represents the same meaning as described above)
- R E — CO— O— R D — group R E and R D have the same meaning as above
- R E 0-CO-R D single group R E and R D are )
- R E R E 'N— R D — group R E and R E ' are the same or different, R E is represents the same meanings, R E, represents the same meanings as R E of, R D represents the same meaning as), R E -CO-NR E '-.
- M B Q— R D — group [M B. M C. —Group ⁇ M C. M D. One R D , one ⁇ M D. May be substituted with a M A — group (M A represents the same meaning as described above), or a 6-10-membered aryl group or a M A — group (M A is the same as defined above).
- the group may be substituted with a 5- to 10-membered heterocyclic group or M A — group (M A represents the same meaning as described above).
- 3 may contain an unsaturated bond 3 1 10-membered hydrocarbon or heterocyclic group, or
- G Q forms a saturated or unsaturated, non-aromatic, 5- to 14-membered hydrocarbon ring or heterocyclic ring which may have a substituent.
- Is substituted with a force Ruponiru group or Chiokaruponiru group, further, O alkoxy group, Chiomoto, - - group ⁇ I ⁇ is a hydrogen atom or, C1-C10 alkyl group, or, eight androgenic atom or R 2 - 1 A — group (R 2 represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group, represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group).
- ⁇ Forming a 5- to 12-membered hydrocarbon ring which may be substituted with a sulfinyl group or a sulfonyl group.
- M c o is representative of the same meaning as above), M e.
- M e. O—CO— group M c Q represents the same meaning as described above
- R e N— group M c .
- M c 0 — CO— NR e — group M c .
- R e have the same meaning as above.
- Mc . ⁇ one C0-NR e one group M c. And R e represent the same meaning as above.
- M c. R e N—CO— group M c .
- M c Q R e N— CO— NR e , — group (M c . R e and R e , Represents the same meaning as described above.), M c . ; E NC ( NR e, ) -NR e " one group (M c R e R e 'and R e ,, represents the same meaning as above;..)., M c - S_ ⁇ 2 - NR e - group (M c and R e are the same meaning and..) or M c Q R e N-S_ ⁇ 2 -.
- R d represents the same meaning as described above.
- a 5- to 12-membered hydrocarbon ring or heterocyclic ring which may have an oxy group, a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a sulfur group or a sulfonyl group, and is aromatic Or, it is a non-aromatic, monocyclic or condensed ring that is condensed with the ⁇ ring.
- 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 —NT a — group ( ⁇ ⁇ represents a hydrogen atom or a substituent on a nitrogen atom).
- T alpha represents the same meaning as, L B represents a hydroxyl group or a methyl group.
- T alpha represents the same meaning as, L Y represents a C1-C10 alkyl group.
- T alpha represents the same meaning as described above.
- W A represents the same meaning as described above, and ⁇ ⁇ and L 8 may have a substituent C 3 -C 10 alkylene group or a substituent C 4 -C 10 Forms an alkenylene group.
- Q B represents a hydroxyl group that may be substituted
- X a is a substituent on a carbon atom, a C1-C10 alkyl group substituted with a cyano group, or a tetrahydropyran 4-1 ylidene group CI-C10 alkyl group, or a C2-C10 alkenyl group substituted with a halogen atom or a cyano group, or a C2-C10 alkenyl group substituted with a CI-C10 alkoxycarbonyl group, or a hydroxy group A substituted C3-C10 alkynyl group or a. -r! -b- r! ⁇ a.
- —CO— group (r Q represents the same meaning as described above), a cyano group or a sulfomethyl group, ri represents a C1-C10 alkylene group, ri, represents a single bond or C1-C10 alkylene B represents an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or an imino group.
- a 2 — y— CO— NH— group (a 2 represents a C2-C10 alkyl group substituted with a —C10 alkoxy group, and y represents an oxy group or an imino group), or , RO—COCO—NH— group (r is as defined above), or a 3 — z—NH— group (a 3 is a C2-C10 alkenyl group, or CI-C10 An alkoxy group, a CI-C10 alkoxycarbonyl group, a C1-C10 alkyl group substituted with a strong lpoxy group or a cyano group, and z represents a strong sulfonyl group or a sulfonyl group.)
- a 4 —NHCO— group ⁇ a 4 is a C ⁇ C10 alkoxy group, or a C3-C10 alkenyloxy group, or r.
- a C2-C10 alkyl group substituted with or rO 1 CO— group (where r represents the same meaning as described above), a C ⁇ C10 alkyl group substituted with a cyano group or an aminocarbonyl group, or r 0 1 C 0 — (r 0 — C 0 CH 2 ) CH— group (where r represents the same meaning as described above).
- r represents the same meaning as ⁇
- a 5 — NHS0 2 — group (a 5 represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group), or r Q ⁇ N ⁇ CH— group (r. It represents the same meaning as described above.) Or r.
- Y a is a halogen atom, or 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 C1-C10 alkoxy group, or a C2-C10 alkenyl group, Or a C2-C10 alkynyl group, or a 2-oxomonoxazolidine-3-yl group, or a CI-C10 alkoxy group substituted with a [1,3] dioxolan_2-yl group, or a morpholino group, Or a.
- a.' represents a C1-C10 alkyl group which may be substituted with a halogen atom
- Or r Q CO—NH— group (r. Represents the same meaning as described above.), Or r. r 0 'NC ⁇ NH— group (r.
- r.' represents the same meaning as above.) or r r'NCO— group (1 "and 1"'have the same meaning as above. Table to.), or represents a hydroxyl group
- Q is 0, 1 represents 2 or 3, when Q is 2 or more, Y a are the same or different, when q is 2 or more, adjacent Y a may be condensed with a ring to form a 2,3-dihydro-benzo [1,4] dioxin ring.
- Q a is r a - ⁇ one group ⁇ r a is a hydrogen atom, or, C1-C10 alkyl groups, or, C3-C10 alkenyl group, or, C3- C10 alkynyl group, or, r . r Q 'N—CH 2 group (r. and r.' represents the same meaning as described above), rOCH 2 — group (r represents the same meaning as described above), r. A CO— group (where r.
- a CI-C10 alkoxycarbonyl group a carboxy group, an aminocarbonyl group, or a CI-C10 alkyl group substituted with a cyano group
- r 3 — — Represents a group (wherein r 3 represents a phenyl group or a pyridyl group, represents the same meaning as described above).
- r 4 and r 4 are the same or different and are a hydrogen atom or a C ⁇ C10 alkyl group, or A C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, but not simultaneously a hydrogen atom.
- a represents an oxygen atom or - NT a - group [T a, r b - group (r b is different r a same or different and each represents the same meaning as r a.) or r 3 '- group ( r 3, is different from r 3 and same or different, represent a representative.) the same meaning as r 3.
- T a represents the same meaning as above, L b represents a hydroxyl group or a methyl group.
- T a represents the same meaning as, L c represents CI- C10 alkyl group.
- T a represents the same meaning as, K b is Shiano group or U_ ⁇ _C_ ⁇ one group (U represents. A hydrogen atom or a C1-C10 alkyl group);. ]
- W a represents the same meaning as described above, and K c and L d form a C3-C10 alkylene group or a C4-C10 alkenylene group.
- T a represents the same meaning as described above, and represents O— 3 ⁇ 4 (r fl represents the same meaning as ⁇ ). ]
- An extracellular matrix gene transcription repressing composition comprising the compound according to 2-5, 13 or 14 above and an inert carrier;
- An extracellular matrix gene transcription repressing composition comprising the compound according to 5 or 14 above and an inert carrier;
- composition according to 1 or 12 above as an active ingredient for improving tissue fibrosis by reducing the amount of extracellular matrix accumulation by decreasing the expression level of an extracellular matrix gene 2.
- An effective amount of a cinnamoyl compound contained as an active ingredient in the composition described in the preceding paragraph 1 or 12 is administered to a mammalian patient in need of treatment for improving tissue fibrosis.
- a method for improving tissue fibrosis comprising administering an effective amount of the compound described in 2 to 5, 13 or 14 to a mammalian patient in need of treatment for improving tissue fibrosis Law;
- An effective amount of the cinnamoyl compound contained as an active ingredient in the composition described in the preceding paragraph 1 or 12, or the compound described in the preceding paragraph 2 to 5, 13 or 14, for treatment of chronic renal failure A method for treating chronic renal failure, comprising administering to a mammal patient in need. 2 7.
- An effective amount of a cinnamoyl compound contained as an active ingredient in the composition described in the preceding paragraph 1 or 12, or a compound described in the preceding paragraph 2 to 5, 13, or 14, requires treatment for heart failure treatment
- a method of treating heart failure comprising administering to a mammalian patient
- a TGF- ⁇ action-suppressing composition comprising a cinnamoyl compound contained as an active ingredient in the composition described in the preceding paragraph 1 or 12 and an inert carrier; 3 1.
- a composition for inhibiting TGF- ⁇ action comprising a compound according to 5, 13 or 14, and an inert carrier; 3 2.
- a hair nourishing composition characterized;
- a hair-growth method comprising administering to a mammalian patient;
- the saturated hydrocarbon group in the alkyl group, haloalkyl group, alkoxy group, alkoxycarbonyl group, alkylthio group, alkylsulfinyl group, alkylsulfonyl group and alkylene group may be branched, and the carbon atom Or an unsaturated hydrocarbon group in the alkenyl group, alkenyloxy group, alkynyl group, alkynyloxy group, alkenylene group and alkynylene group may be branched. Alternatively, 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-trifluoro.
- Examples of the Si group include a methoxy group, an ethoxy group, a cyclopentyloxy group, and 2-cyclohexyl ethoxy group.
- examples of the alkylthio group include a methylthio group.
- examples of the alkylsulfinyl group include, for example, A methylsulfinyl group, and the like.
- Examples of the alkylsulfonyl group include a methylsulfonyl group.
- Examples of the alkylene group include a methylene group, an ethylethylene group, and a 1,4-cyclohexylene group.
- Examples of the alkenyl group include a vinyl group, 2-propenyl group, 3-methyl-2-butenyl group, 1,3-butenyl group, 3-cyclohexenyl group, and the like.
- Examples of the group include ethynyl group, 2-propynyl group, 2-pentene-4-yl group and the like.
- alkynylene groups for example, Echiniren group, propenylene group and the like.
- examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- the pyridyl group includes a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group
- the furyl group includes a 2-furyl group and a 3-furyl group
- the cheryl group is a 2-
- the naphthyl group includes a 1-naphthyl group and a 2-naphthyl group.
- Cinnamoyl compounds represented by formulas (I), (II), (III), (IV), (V), (VI), (VI '), ( ⁇ ), ( ⁇ ) and (V) , Compounds (I), (II), (III), (IV), (V), (VI), (VI '), ( ⁇ ), ( ⁇ ') and (V)) , ⁇ ring, AO ring, A ring and a ring are pyridine rings, their N-oxides are also included.
- Compounds (I) to (V), ( ⁇ ), ( ⁇ ) and (V) (hereinafter sometimes referred to as the compound of the present invention) also represent pharmacologically acceptable salts thereof.
- the pharmacologically acceptable salts are the salts of the compounds (I) to (V), ( ⁇ ), ( ⁇ ⁇ ') and (V) with inorganic acids.
- examples of the salt with an inorganic acid include hydrochloride and hydrobromide, and examples of the salt with an organic acid include acetate and benzoate, and a salt with an inorganic base.
- Examples include potassium salts and sodium salts.
- salts with organic bases include pyridine salts and morpholine salts.
- TA 0 are D 1 D 2 , D 3 , D 4 , D 5 , R independently of each other. , R. ,, R 0 ',, R x , R ′', R x '', R 2 , R 2 'R 3 , R 4 , R 4 ', R 5 , R 6 , A,, A 2 , A 3, A 4 , A 5 A 6 > A 7 A 7, A 7 A 8 , A 8 ⁇ A 9 , A 9 , A 9 , A 9 , A
- 1, m, m ′, n and n ′ are represented by integers.
- 6- to 10-membered aryl group refers to a group that forms a monocyclic or condensed aromatic hydrocarbon ring, such as a phenyl group, a 1-naphthyl group, a 2-naphthyl group, 6-indanyl group, etc.
- “5- to 10-membered heteroaryl group” means a group that forms a monocyclic or condensed aromatic heterocycle, such as 2-furyl group, 3-furyl group, etc.
- Hydrocarbon ring or heterocyclic group '' includes a single ring or a condensed ring, such as 2-cyclohexenyl group, 2-morpholinyl group, 4-piperidyl group, etc., which are singular or the same or different.
- a plurality of said M a — groups may be substituted.
- Compound (I), (II), Te (1 ') and (Iotaganma) of ⁇ substituents Z Q group odor can take the alpha, "alpha ring fused to 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 sulfonyl group, one or the same or different plural atoms or It may have a group.
- R a 0 of the group “optionally substituted 5- to 7-membered aryl group or heteroaryl group” means a group forming a monocyclic or condensed aromatic hydrocarbon ring or a monocyclic or condensed ring
- a phenyl group, 1-naphthyl group, 2-naphthyl group, 6-indanyl group, 2-furyl group, 3-furyl group, 2-cenyl group, 3- Examples include a chenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-monopyridyl group, a 2-quinolyl group, and the like, and these may be substituted with a single or the same or different plural Ma-groups.
- group (a) of the group B which can be substituted with X A in the compound (IV) “oxy group, thio group, sulfinyl group, sulfonyl group or single group (Ri ′” has the same meaning as above.
- a C2-C10 alkylene group optionally substituted with means that one or more carbon atoms are an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or a —NR,
- — group (1 ⁇ ′ is Represents a C2-C10 alkylene group which may be replaced by a single group or a plurality of groups which are the same or different from each other, and selected from “oxy group, thio group, sulfinyl group, sulfonyl”
- a C3-C10 alkenylene group which may be substituted with a group or one NRi ′ group means that one or more carbon atoms are an oxy group, Group, sulfinyl group, sulfonyl group Or one NI ⁇ 'group (1 ⁇ ' represents the same meaning as described above) may be replaced by one or a plurality of groups selected from
- the CI-C10 alkylene group which may be substituted with a) is a group in which one or more carbon atoms may be substituted with a methyl group, or one or more carbon atoms are Substituted with one or a plurality of the same or different groups selected from an oxy group, a thio group, a sulfinyl group, a sulfonyl group or a —NI ⁇ — group (where R 1 represents the same meaning as described above).
- -C10 alkenylene group One or more of the above may be substituted with a methyl group, or one or more of the carbon atoms may be an oxy group, a thio group, a sulfinyl group, a sulfonyl group, or a —NI ⁇ — group (1 ⁇ It represents the same meaning, and represents a C2-C10 alkenylene group which may be replaced by a single group or a plurality of the same or different groups selected from Compound (I), (II), can take Upsilon alpha (1 ') and (Iotaganma) X. Group, ⁇ . Swarm and eagle. Examples of groups belonging to the group are shown in Table 24, Table 25 and Table 26 below.
- ⁇ of compound (III). ⁇ which can take. Group, ⁇ . Group, C. Group, D. Group, ⁇ . Group, F 0 group, G Q group, H. Group, I. Group, J Q group, K. Group, L. Group, a group belonging to M Q group and N Q groups, respectively, Table 1 below, Table 2, Table 3, Table 4, Table 5-8, Table 9-12, Table 13-16, Table 17, Illustrated in Table 18, Table 19, Table 20, Table 21, Table 22 and Table 23, Y A. Possible X. Group, Y. Group and Z. The groups belonging to the group are exemplified in Table 24, Table 25 and Table 26 below, respectively, and Q A. And T A. Are shown in Table 27 to Table 28 and Table 29 below.
- the groups belonging to the groups are respectively shown in Table 1, Table 2, Table 3, Table 4, Table 5, Tables 8 to 8, Tables 9 to 12, Table 13 to: L 6, Table 17, Table 18, Table 19 Exemplified in Table 20, Table 21, Table 22 and Table 23, Y A can take X group, Y group and Exemplified groups belonging to group Z, respectively, Table 2 4 below, and illustrated in Table 2 5 and Table 2 6, the Q A and T A, respectively, in Table 2 7 Table 2 8 and Table 2 9 below To do.
- A. Group ⁇ N Examples of groups and groups belonging to Group A to Group N are shown in Tables 1 to 23 below. In the case of groups capable of geometric isomerism, all the geometric isomers are meant and tautomerism is possible. In the case of a radical, all 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.
- Z H3 H0 Z H0OO0 S H0O- ⁇ 0 2 ⁇ 0 2 ⁇ ⁇ ⁇ - OC
- Table 17 shows the groups belonging to Group and Group H. Table 1 7
- Table 18 shows the groups belonging to I o group and I group.
- Table 21 shows the groups belonging to the L Q group and the L group.
- Table 22 shows the groups belonging to the group and M group. Table 2 2
- Group ⁇ Z Examples of groups belonging to Group X and Group X to Group Z are shown in Table 24 to Table 26 below. In the case of groups capable of geometric isomerism, all geometric isomers are meant and tautomerism is possible. In the case of a group, all tautomers thereof are meant.
- Table 26 shows examples of ⁇ -ring, AO-ring or ⁇ -ring condensed with group or ⁇ group.
- T alpha is a hydrogen atom or CI- C10 alkyl group, or a hydroxyl group that group ( ⁇ '_7), and T alpha is CI- C10 alkyl group If, or a T alpha hydrogen atom or CI- C10 alkyl group ( ⁇ '- 8), and, if U is a hydrogen atom. More specifically, cinnamoyl compounds' and have contact to,] 3 ( ⁇ ) '' is a group ( ⁇ '' -1), if T alpha is a case of a hydrogen atom or a C1-C10 alkyl group Can be given.
- X A when, is 2 or more. Are the same or different, and the sum of p and q is 3 or less,
- T AQ represents the same meaning as described above.
- T A a group represented by T A.
- Q B of the group (III'-7) is a hydrogen atom or a CI-C10 alkyl group, or Q B of the group (III'-7).
- T A 0 is a C1-C10 alkyl group, or T A of the group ( ⁇ -8).
- B 0 ' is a group ( ⁇ '-1)
- T AQ is a hydrogen atom or a Cl-C 10 alkyl group. It is done.
- cinnamoyl compound shown by these is mention
- X is a methine group, and the methine group has no substituent.
- B ' is a group (IV -1), a group (IV' -7) or a group (IV '-8), and the group (IV, -1) is , Formula (IV ',-1)
- T A represents the same meaning as above.
- T A is a hydrogen atom or a CI-C10 alkyl group, or Q B of the group (IV′-7) is a hydroxyl group, and T A is C1-C10 In the case of an alkyl group, or the case where T A of the group (IV′-8) is a hydrogen atom or a CI—C10 alkyl group, and U is a hydrogen atom. More specifically, 'to have you to, B cinnamoyl compound (IV)' a group (IV '' - 1) a A, if T A is the case for hydrogen atom or a C Bok C10 alkyl group .
- T a represents the same meaning as above.
- T a represents the same meaning as above.
- T a is a hydrogen atom or a C1-G10 alkyl group
- T a of the group (V ′, ⁇ 7) is a C1-C10 alkyl group
- a group ( V ', - T a of 8) is a hydrogen atom or CI- C10 alkyl group
- U may be mentioned is the case of the hydrogen atom.
- b ′′ is a group (V ′ ′′-1) and TA is a hydrogen atom or a CI—C10 alkyl group.
- the formula ( ⁇ ′ ′′) is a compound (V), more specifically, the formula ( ⁇ ′ ′′)
- X a ′ represents CH 3 ⁇ CH 2 CONH— group, CH 3 ⁇ COCH 2 NHC ⁇ group, HOCOCH 2 NHC ⁇ 1 group, CH 3 ⁇ _CH 2 CH 2 NHCO- group, CH 3 OC_ ⁇ _CH 2 ⁇ one group, H0C0CH 2 0- group, HOCH 2 CH 2 ⁇ one group, CH 3 ⁇ _CH 2 CH 2 OCONH- group or (CH 3) 2 NCH 2 CH 2 0— represents a group, b ''''''''
- r x represents a hydrogen atom or a methyl group.
- the same meanings as the above) represented by compounds of formula (/ 3) (wherein jS represents the same meaning as described above) can be produced by reacting with a compound represented by
- the compound (a) when / 3 is a group represented by the above formula (1-1), (1-4), (1-5) or (1-7), the compound (a) is converted to / 3 Can be produced by reacting the compound ( ⁇ ) with the group (1-1), (1-4), (1-5) or (1-7).
- the reaction temperature range is usually from room temperature to the solvent reflux temperature
- the reaction time range is usually from instantaneous to about 24 hours.
- the reaction is usually performed in the presence of a base.
- bases that can be used include piperidine, pyridine, trytylamine, N, N-dimethylamine, triptylamin, morpholine, N-methylmorpholine and other organic bases, sodium hydroxide, potassium hydroxide, potassium carbonate and other inorganic substances.
- the amount of the reagent used for the reaction is usually 0.5 to 2 mol for the compound (3) and usually 0.1 to 1.0 mol for the base with respect to 1 mol of the compound ( ⁇ ).
- a solvent is not always necessary, but it is usually performed in the presence of a solvent.
- Solvents that can be used for the reaction include lower alcohols such as methanol and ethanol, aliphatic hydrocarbons such as hexane and petroleum ether, aromatic hydrocarbons such as benzene and toluene, chloroform, dichloroethane, and the like.
- Halogenated hydrocarbons such as jetyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate and jetyl carbonate, nitriles such as acetonitrile and isobutyl nitrile , Amides such as formamide, ⁇ , ⁇ -dimethylformamide, sulfur compounds such as dimethyl sulfoxide, etc., or a mixture thereof.
- reaction solution after completion of the reaction is subjected to usual post-treatment such as organic solvent extraction, washing with water, and concentration of the organic layer under reduced pressure. If necessary, the reaction solution is purified by operations such as chromatography and recrystallization.
- the compound ( ⁇ ) can be obtained.
- Compound (III) is, for example, a compound represented by the formula (AO) (wherein A 0, X A , Y A , p and q represent the same meaning as described above), and the formula (B0) (Wherein B 0 represents the same meaning as described above.) Can be produced by reacting in the same manner as described above.
- Compound (IV) is, for example, a compound represented by the formula (A) (wherein A, X A ′, Y A , p and q represent the same meaning as described above). It can be produced by reacting a compound represented by the formula (B) (wherein B represents the same meaning as described above) in the same manner as described above.
- Compound (V) includes, for example, a compound represented by formula (a) (wherein a, X A , Y A , p and Q have the same meaning as described above), and a compound represented by formula (b) (formula In the formula, b represents the same meaning as described above, and can be produced by reacting the compound represented by) in the same manner as described above.
- a part of the compound represented by the formula (a) is known, for example, described in the literature (EP 330645) and can be produced by the method described in the literature (W02005 / 028439).
- Some of the compounds represented by the formula (b) are known, for example, described in the literature (J. Organic Chem. (1965) 30, 2241).
- the compound represented by the above formula (VI 1-3) which is a part of the compound represented by the formula (VI 1-3) is a novel substance with no examples reported so far.
- Compound (VII-3) can be produced, for example, by subjecting the compound represented by the formula (VII-2) to a cyclization reaction.
- 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 cyclization reaction is usually carried out in the presence of a base.
- the base to be used include sodium mettodikido, sojumudetoxide, n-butyllithium, pyridine, triethylamine, N, N-dimethylaniline.
- Organic bases such as triptylamin, N-methylmorpholine, sodium hydride, sodium hydroxide, potassium hydroxide And inorganic bases such as potassium carbonate.
- the amount of the reagent used for the reaction is usually 0.8 to 2 mol of the base with respect to 1 mol of the compound (VI I-2).
- a solvent is not necessarily required, but it is usually carried out in the presence of a solvent.
- Solvents that can be used in the reaction include lower alcohols such as methanol and ethanol, aliphatic hydrocarbons such as hexane and petroleum ether, aromatic hydrocarbons such as benzene and toluene, chloroform, and dichloromethane.
- Halogenated hydrocarbons such as ethylene, ethers such as jetyl ether, dioxane, and tetrahydrofuran, ketones such as acetone and methylethylketone, esters such as ethyl acetate and jetyl carbonate, acetonitrile, isobutylnitrile, etc.
- ketones such as acetone and methylethylketone
- esters such as ethyl acetate and jetyl carbonate
- acetonitrile isobutylnitrile
- examples thereof include nitriles, formamides, amides such as N, N-dimethylformamide, sulfur compounds such as dimethylsulfoxide, and the like, or mixtures thereof.
- reaction solution after completion of the reaction is subjected to usual post-treatments such as organic solvent extraction, washing with water, and concentration of the organic layer under reduced pressure, etc., and if necessary, it is purified by operations such as chromatography and recrystallization.
- Compound (VI I-3) can be obtained.
- the compound (VI I-2) is a novel substance with no examples reported so far.
- Compound (VI 1-2) can be produced by subjecting the compound represented by the formula (VI I-1) to 3-oxopropylylamidation.
- 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 carried out in the presence of a 3-oxoptylylamidating agent.
- the 3-oxoptyrylamidating agent to be used include diketene, 2, 2, 6-trimethyl-4H-1, 3-dioxin. Examples thereof include methyl acetoacetate and t-butyl acetoacetate.
- the amount of the reagent to be used for the reaction is usually 0.8 to 7 mol per 3 mol of compound (VI I-1) relative to 1 mol of compound (VI I-1).
- a solvent is not necessarily required, but it is usually performed in the presence of a solvent.
- Solvents that can be used in the reaction include lower alcohols such as methanol and ethanol, aliphatic hydrocarbons such as hexane and petroleum ether, aromatic hydrocarbons such as benzene, toluene, and xylene, , Halogenated hydrocarbons such as dichloroethane, ethers such as jetyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methylethyl ketone, esters such as ethyl acetate and jetyl carbonate, acetononitrile Nitriles such as isobutyl nitrile, formamide, amides such as N, N-dimethylformamide, sulfur compounds such as dimethyl sulfoxide, and the like, or a mixture thereof.
- lower alcohols such as methanol and ethanol
- aliphatic hydrocarbons such as hexane and petroleum ether
- aromatic hydrocarbons such as benzene, to
- the reaction mixture after completion of the reaction is post-treated in the same manner as in the cyclization reaction of compound (VI I-2) and purified in the same manner to give compound (VI I-2).
- the compound (VI I-1) is described in, for example, the literature (T etrahedron (1 997), 5 3 (4 7), 1 6 0 6 1) and is a known compound (VI I-3
- the compound represented by the formula (XI-2) which is a part of the compound (VI) is obtained by alkylating the compound represented by the formula (XI-1) which is a part of the compound (VI I-3). Can be manufactured.
- reaction method examples include a method of reacting compound (XI-1) with an alkylating agent in the presence of a base.
- the reaction of compound (XI-1) with an alkylating agent in the presence of a base does not necessarily require a solvent, but is usually carried out in a solvent.
- the solvent used in the reaction include acid amides such as N, N-dimethylformamide and N, N-dimethylacetamide, sulfoxides such as dimethylsulfoxide, and phosphoramide compounds such as hexamethylphosphoramide. And ketones such as acetone and methyl ethyl ketone.
- the base used in the reaction include alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, silver oxide and the like.
- alkylating agent examples include alkyl sulfonic acid esters such as methyl methane sulfonate, methyl ester of p-toluene sulfonic acid, aryl sulfonic acid esters such as ethyl ester of p-toluene sulfonic acid, and sulfuric acid such as dimethyl sulfate.
- alkyl sulfonic acid esters such as methyl methane sulfonate, methyl ester of p-toluene sulfonic acid, aryl sulfonic acid esters such as ethyl ester of p-toluene sulfonic acid, and sulfuric acid such as dimethyl sulfate.
- esters, halides such as methyl iodide and bromide chill.
- the amount of the reagent used in the reaction is usually 1 mol to 2 mol of the base, and the alkylating agent is usually 1 mol to 2 mol with respect to 1 mol of the compound (XI-1). .
- the reaction temperature is usually in the range of 0 ° C to 100 ° C, and the reaction time is usually in the range of instantaneous to 24 hours.
- the reaction mixture after completion of the reaction can be purified in the same manner as in the cyclization reaction of compound (VII-2) to obtain compound (XI-2).
- Table 30 shows the novel compound (VII-3) represented by compound numbers (1A-1) to (1A-8). Table 30
- Table 31 shows the novel compounds (VII-2) represented by compound numbers (IB-1) to (IB-8).
- the compounds represented by the compound numbers (1 b) to (17 b) are represented by the formula (Vb) (Wherein, a, X a, r a and t a represent the same meanings as the above.)
- Table 4 6 Table 4 7
- Table 4 8 Compound (Vc) 0 0 0 0
- Compounds (I) (V) ( ⁇ ) ( ⁇ ⁇ ) and (V) have the ability to suppress transcription of extracellular matrix genes such as type I collagen gene and fibronectin gene. This ability improves the fibrosis of tissues by reducing the amount of extracellular matrix genes such as type I collagen and fibronectin genes, leading to a decrease in the amount of extracellular matrix accumulated such as collagen and fibronectin. It is important for Therefore, the compounds (I) (V) ( ⁇ ) ( ⁇ ⁇ ') and (V) reduce the expression level of extracellular matrix genes such as type I collagen gene and fibronectin gene, thereby reducing the expression of collagen, fibronectin and the like. It can be used as an active ingredient in compositions (pharmaceuticals, cosmetics, food additives, etc.) for improving tissue fibrosis by leading to a decrease in the amount of fine JJ extracapsulated matrix accumulated.
- diseases to which the transcription repressing composition of the present invention or the composition for improving fibrosis of the present invention can be applied include, for example, hardening by tissue fibrosis due to excessive accumulation of extracellular matrix such as collagen and fibronectin, As a result, diseases (ie, fibrosis, etc.) that cause deterioration of the function of tissues such as organs and scar formation can be raised.
- cirrhosis chronic vaginitis, Skills gastric cancer, interstitial lung disease, asthma, chronic obstructive pulmonary disease, glomerulonephritis, lupus nephritis, tubulointerstitial nephritis, Ig A nephropathy, Nephrosclerosis, diabetic nephropathy Hereditary kidney disease, myocardial fibrosis, heart failure, restenosis after PTCA, arteriosclerosis, myelofibrosis, rheumatoid arthritis, post-inflammation hyperplasia, post-operative scar, burn scar, atopic dermatitis, Examples include hypertrophic scars, uterine fibroids, prostatic hypertrophy, scleroderma, Alzheimer's disease, sclerosing peritonitis, diabetic retinopathy, type I diabetes, and the like.
- hepatitis C virus or hepatitis B virus induces chronic inflammation and increases the amount of TGF-j8.
- TGF-j8 ⁇ Accumulation of type III collagen
- ⁇ Accumulation of type III collagen is already known to cause the disease (see, for example, Clin. Liverdiss., 7, 195-210 (2003)).
- interstitial lung disease as an example, it is considered that the amount of GFGF-) 3 increases by inducing lupus inflammation caused by mites, viruses, tuberculosis, etc., causing pulmonary fibrosis and causing the disease It has been.
- TGF-] 3 increases in the glomeruli due to hyperglycemia in the former, and Ig A accumulates in the glomeruli in the latter. It has already been suggested that nephritis is induced and the amount of TGF- / 3 increases, causing renal fibrosis (particularly accumulation of type I and type IV collagen) and causing the disease ( For example, see Am. J. Phy siol. Ren al Ph siol., 278, F 830-F 838 (2000), Kidney Int., 64, 149-159 (2003)).
- the dbZdb mouse which is a model animal for diabetic nephropathy, has a mutation in the leptin receptor that suppresses food intake, resulting in hyperglycemia due to overeating and spontaneously accompanying diabetes.
- blood glucose concentration is about 4 times higher than in normal mice, and glomerular fibrosis and TGF—; 8 levels are increased (for example, Am. J. P at ho l., 158, 1653-1663 (200 1)).
- the anti-Thy-1 rat which is a model animal of IgA nephropathy, is an artificially induced renal fibrosis by administering an anti-Thy-1 antibody to a normal rat.
- renal fibrosis is suppressed by administering an anti-TGF-] 3 receptor antibody to the model animal (for example, Kidney Int., 60, 1745-1755 ( 2001)).
- an anti-TGF-] 3 receptor antibody for example, Kidney Int., 60, 1745-1755 ( 2001)
- the cause of scleroderma is unknown, but skin fibrosis has been improved by administering a TGF-) 3 inhibitor to the Tsk mouse, which is the model animal (eg, J. I nve s t. De rma to l., 118, 461-470 (2001)).
- a compound that suppresses the action of TGF-3 inhibits the promotion of collagen synthesis by TGF-3; 3, suppresses tissue fibrosis, and obtains a therapeutic effect for fibrosis (pharmaceuticals) , Cosmetics, food additives, etc.).
- the pathogenesis of heart failure such as left ventricular diastolic failure is considered to be one of fibrotic heart fibrosis.
- it can be used as an active ingredient in compositions (pharmaceuticals, etc.) to inhibit fibronectin synthesis promotion by TGF- / 3 to suppress tissue fibrosis and obtain a therapeutic effect on heart failure. is there.
- Such a transcription repressing composition of the present invention or a composition for improving fibrosis of the present invention contains the compounds (I) to (V), (1 ′), ( ⁇ ) and (V) and an inert carrier.
- Compounds (I) to (V), ( ⁇ ), ( ⁇ ) and (V) contained in these compositions are usually 0.01% to 99.99% by weight, and are inert carriers. Is usually 99.99% by weight to 0.01% by weight.
- the inert carrier is a pharmaceutically acceptable carrier or excipient, and the present transcription inhibition composition and the present fibrosis improving composition are further used as pharmaceutical additives, cosmetic additives, food additives, etc. It may contain.
- the compounds (I) to (V), ( ⁇ ), ((′) and (V) are, as shown in Examples 3 to 5 described later, a type I collagen gene possessed by TGF—; 8, Inhibits the ability of the fibronectin gene to promote transcription. That is, the compounds (I) to (V), ( ⁇ ), (II ′) and (V) are TGF-3 antagonists capable of suppressing the action of TGF-3. Therefore, the compounds (I) to (V), ( ⁇ ), ( ⁇ ′) and (V) can also be used as active ingredients of the TGF-J3 action inhibitory composition.
- Such a TGF-suppressing composition of the present invention contains the compounds (I) to (V), ( ⁇ ), ( ⁇ ) and (V) and an inert carrier.
- the compounds (I) to (V), ( ⁇ ), ( ⁇ ') and (V) contained in these compositions are usually 0.01% to 99.99% by weight and are inert.
- the carrier is usually 99.99% by weight to 0.01% by weight.
- the inert carrier is a pharmaceutically acceptable carrier, and the TGF- / 3 inhibitor composition and the hair nourishing composition of the present invention are further used as pharmaceutical additives, cosmetic additives, food additives. Including You may have.
- the pharmaceutically acceptable carrier, excipient, pharmaceutical additive, food additive, cosmetic additive and the like used in the composition can be appropriately selected according to the specific use of the composition.
- the form of the composition can be, for example, various solids, liquids, etc., depending on the specific application.
- specific forms include, for example, powders, fine granules, Oral preparations such as granules, tablets, syrups, capsules, suspending agents, emulsions, extracts and pills, injections, transdermal absorption agents such as external solutions and ointments, suppositories and topical agents And the like.
- Oral agents include, for example, gelatin, sodium alginate, starch, corn starch, sucrose, lactose, glucose, mannitol, carboxymethylcellulose, dextrin, polyvinylpyrrolidone, crystalline cellulose, soybean lecithin, sucrose, fatty acid ester, talc, stearic acid Carriers, excipients, binders, disintegrants, surfactants, lubricants, fluidity promoters, diluents, preservatives, colorants, such as magnesium, polyethylene glycol, magnesium silicate, and anhydrous silicate It can be produced according to ordinary methods using pharmaceutical additives such as fragrances, stabilizers, humectants, preservatives, and antioxidants.
- pharmaceutical additives such as fragrances, stabilizers, humectants, preservatives, and antioxidants.
- 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 active ingredient is about 1 mg to about 2 g, preferably about 5 mg to about lg is administered as the amount of active ingredient.
- the daily dose can be administered once or divided into several times.
- injections include water-soluble solvents such as physiological saline and sterile water Ringer's solution, water-insoluble solvents such as plant oil and fatty acid esters, isotonic agents such as glucose and sodium chloride, and solubilizing agents. 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. This To administer such parenteral agents, injection (subcutaneous, intravenous, etc.), transdermal administration, or rectal administration may be used.
- water-soluble solvents such as physiological saline and sterile water Ringer's solution
- water-insoluble solvents such as plant oil and fatty acid esters
- isotonic agents such as glucose and sodium chloride
- solubilizing agents solubilizing agents. It can be produced according to ordinary methods
- the topical agent can be produced, for example, by incorporating the compounds (I) to (V), ( ⁇ ), ( ⁇ ') and (V) into a pellet of a sustained release polymer such as ethylene vinyl acetate polymer. it can. This pellet may be surgically implanted into the tissue to be treated.
- a sustained release polymer such as ethylene vinyl acetate polymer.
- the dosage 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. About 0.1 mg to about 50 Omg may be administered. In addition, the daily dose can be administered once or divided into several times.
- specific forms of cosmetics to which the compounds are added include, for example, Liquid, milky, cream, lotion, ointment, gel, aerosol, mousse and the like can be mentioned. Lotions can be produced according to conventional methods using cosmetic additives such as suspending agents, emulsifying agents, preservatives and the like.
- the dose varies depending on the age, sex, body 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 daily dose can be administered once or divided into several times.
- the specific form of the food to which the additives are added is, for example, powder , Tablets, beverages, mixed liquids with ingestible gels or syrups, for example, seasonings, Japanese sweets, Western confectionery, ice confectionery, beverages, spreads, pastes, pickles, canned bottles, processed meat products, processed fish and fishery products
- General foods and beverages such as processed milk / eggs, processed vegetables, processed fruits, processed cereals, etc. 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, dosage form, etc. 50 Omg should be administered.
- the daily dose can be administered once or divided into several times.
- Example 1 to 1 to 1 to 3 include compound numbers (1 A-1) and (1 A-5) in Table 30 (VII-3) and compound numbers in Table 31
- the synthesis of compound (VII-2) represented by (IB-1) is described below.
- 2-Aminonicotinic acid methyl ester 1. Add 3 ml of 2,2,6-trimethyl-4H-1,3_dioxin-4-one to a solution of 1.52 g of xylene in 3 ml and add 30 ml at 120 ° C for 30 minutes. Heated. The reaction solution was subjected to silica gel column chromatography to obtain 1.15 g of white solid of 2- (3-oxoptyllyamino) nicotinic acid methyl ester [Compound No. (1 B-1)].
- Example 2 Compound numbers 32 to 37 (19 a), (20 a), (29 a), (31 a), (32 a), (36 a), (37 a), (4 0 a), (42 a ), (56 a), (86 a) and (124 a) Compounds (Va), Compound numbers in Tables 38 to 39 (1 b), (2b), (5 b), (9 b ), (10 b), (13 b), (14 b), (16 b) and (17 b) compounds (Vb) and compound numbers (9 c) to (25
- the synthesis of the compound (Vc) represented by c) and the compound (Ve) represented by the compound number (3e) in Table 52 is described.
- Example 2-1 Synthesis of Compound (Va) [Compound No. (19 a)]
- Example 2 except that 0.20 g of 3-[[(methoxycarbonylmethyl) amino] carbonyl] benzaldehyde was used in place of 3- (methoxyacetylamino) benzaldehyde, and 6 ml of methanol was used in place of ethanol.
- Example 2-1 except that 3-((methoxycarbonyl) methoxy] benzaldehyde 0.18 g was used instead of 3- (methoxyacetylamino) benzaldehyde, and methanol 6m 1 was used instead of ethanol. Similarly, 4-hydroxy-1-methyl-3- [3- [3-[(methoxycarbonyl) methoxy] phenyl] acryloyl] -1H- [1,8] naphthyridin-2-one [Compound No. (36 a)] of pale yellow crystals of 0.23 g was obtained.
- Example 2-1 The same procedure as in Example 2-1 was conducted, except that 0.1 g of 6-formyl-2-[(2_methoxyethyl) amino-powered sulfonyl] pyridine was used instead of 3- (methoxyacetylamino) benzaldehyde.
- Compound No. (124a) As a result, 0.05 g of pale yellow crystals were obtained.
- Example 4-13 except that 1.64 g of 6-formyl-2-[(2-methoxyethyl) aminocarbonyl] pyridine was used instead of 3-[(methoxycarbonyl) methoxy] benzaldehyde.
- Example 2-22 except that 3-acetyl-6-methyl-2 (1 H) -pyridinone 74 Omg was used instead of 3-acetyl-4,6-dimethyl-2 (1H) -pyridinone Of 3- [3- [3-[(methoxycarbonyl) methoxy] phenyl] -1-oxo-2-propenyl] -6-methyl_2 (1H) -pyridinone [Compound No. (11c)] Pale yellow crystals were obtained.
- the solution was dissolved and heated for 1 hour and 30 minutes under reflux while removing water with a Soxhlet extractor filled with molecular sieves.
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AU2006219222A AU2006219222A1 (en) | 2005-03-02 | 2006-03-02 | Use of cinnamoyl compound |
US11/885,379 US20090143368A1 (en) | 2005-03-02 | 2006-03-02 | Use of Cinnamoyl Compound |
CA002600287A CA2600287A1 (en) | 2005-03-02 | 2006-03-02 | Use of cinnamoyl compound |
EP06728806A EP1857104A4 (en) | 2005-03-02 | 2006-03-02 | USE OF A CINNAMOYL COMPOUND |
Applications Claiming Priority (2)
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JP2005-057364 | 2005-03-02 | ||
JP2005057364 | 2005-03-02 |
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WO2006093339A1 true WO2006093339A1 (ja) | 2006-09-08 |
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PCT/JP2006/304539 WO2006093339A1 (ja) | 2005-03-02 | 2006-03-02 | シンナモイル化合物の用途 |
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US (1) | US20090143368A1 (ja) |
EP (1) | EP1857104A4 (ja) |
AU (1) | AU2006219222A1 (ja) |
CA (1) | CA2600287A1 (ja) |
WO (1) | WO2006093339A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007132948A1 (ja) * | 2006-05-17 | 2007-11-22 | Sumitomo Chemical Company, Limited | シンナモイル化合物及びその用途 |
WO2007132945A1 (ja) * | 2006-05-17 | 2007-11-22 | Sumitomo Chemical Company, Limited | シンナモイル化合物及びその用途 |
WO2007136125A1 (ja) * | 2006-05-22 | 2007-11-29 | Sumitomo Chemical Company, Limited | 含複素環化合物及びその用途 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8524729B2 (en) * | 2003-09-17 | 2013-09-03 | Sumitomo Chemical Company, Limited | Cinnamoyl derivatives and use thereof |
US8614233B2 (en) | 2007-05-29 | 2013-12-24 | Universite De Montreal | Cinnamoyl inhibitors of transglutaminase |
CA2952069C (en) | 2014-06-16 | 2022-06-14 | University Of Rochester | Small molecule anti-scarring agents |
CN110248934B (zh) * | 2016-09-12 | 2022-05-24 | 帕德罗科治疗公司 | 杂芳基pad4抑制剂 |
Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS564604A (en) * | 1979-06-18 | 1981-01-19 | Eastman Kodak Co | Coinitiating agent composition |
JPS61114234A (ja) * | 1984-10-09 | 1986-05-31 | ザ・ミ−ド・コ−ポレ−シヨン | 3−置換クマリンおよび他の光漂白可能な増感剤を含む感光性マイクロカプセルを使用する画像系 |
EP0330645A2 (de) | 1988-02-23 | 1989-08-30 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue aromatische Aldehyde, ihre Herstellung und Verwendung |
JPH02279702A (ja) * | 1989-04-20 | 1990-11-15 | Nippon Oil & Fats Co Ltd | 光重合開始剤組成物 |
WO1992018483A1 (en) | 1991-04-22 | 1992-10-29 | Fujisawa Pharmaceutical Co., Ltd. | Quinoline derivatives |
JPH09227547A (ja) | 1996-02-20 | 1997-09-02 | Mitsui Toatsu Chem Inc | 可視光感光性樹脂組成物およびその用途 |
WO1997035565A1 (fr) | 1996-03-27 | 1997-10-02 | Toray Industries, Inc. | Derives de cetone et usage medicinal |
WO2000020371A1 (en) | 1998-10-07 | 2000-04-13 | Merck Frosst Canada & Co. | Prostaglandin receptor ligands |
WO2001079187A2 (en) | 2000-04-18 | 2001-10-25 | Cytovia, Inc. | Substituted 1,4-thiazepine and analogs and their use as activators of caspases |
JP2002371078A (ja) | 2001-06-12 | 2002-12-26 | Sankyo Co Ltd | キノリン誘導体及びキノロン誘導体 |
JP2003021901A (ja) * | 2001-07-05 | 2003-01-24 | Fuji Photo Film Co Ltd | 感光性平版印刷版の光重合方法 |
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 |
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 |
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 |
WO2005028439A1 (ja) * | 2003-09-17 | 2005-03-31 | Sumitomo Chemical Company, Limited | シンナモイル化合物およびその用途 |
WO2005028463A1 (ja) * | 2003-09-17 | 2005-03-31 | Sumitomo Chemical Company, Limited | シンナモイル化合物およびその用途 |
WO2005028441A1 (ja) * | 2003-09-17 | 2005-03-31 | Sumitomo Chemical Company, Limited | シンナモイル誘導体およびその用途 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5046666A (ja) * | 1973-08-20 | 1975-04-25 | ||
US4278751A (en) * | 1979-11-16 | 1981-07-14 | Eastman Kodak Company | Photopolymerization co-initiator compositions comprising amine-substituted ketocoumarins and certain acetic acid derivative activators |
US4713312A (en) * | 1984-10-09 | 1987-12-15 | The Mead Corporation | Imaging system employing photosensitive microcapsules containing 3-substituted coumarins and other photobleachable sensitizers |
AU2006225887A1 (en) * | 2005-03-02 | 2006-09-28 | Sumitomo Chemical Company, Limited | Cinnamoyl compound and use thereof |
-
2006
- 2006-03-02 EP EP06728806A patent/EP1857104A4/en not_active Withdrawn
- 2006-03-02 AU AU2006219222A patent/AU2006219222A1/en not_active Abandoned
- 2006-03-02 CA CA002600287A patent/CA2600287A1/en not_active Abandoned
- 2006-03-02 WO PCT/JP2006/304539 patent/WO2006093339A1/ja active Application Filing
- 2006-03-02 US US11/885,379 patent/US20090143368A1/en not_active Abandoned
Patent Citations (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS564604A (en) * | 1979-06-18 | 1981-01-19 | Eastman Kodak Co | Coinitiating agent composition |
JPS61114234A (ja) * | 1984-10-09 | 1986-05-31 | ザ・ミ−ド・コ−ポレ−シヨン | 3−置換クマリンおよび他の光漂白可能な増感剤を含む感光性マイクロカプセルを使用する画像系 |
EP0330645A2 (de) | 1988-02-23 | 1989-08-30 | Gerot-Pharmazeutika Gesellschaft m.b.H. | Neue aromatische Aldehyde, ihre Herstellung und Verwendung |
JPH02279702A (ja) * | 1989-04-20 | 1990-11-15 | Nippon Oil & Fats Co Ltd | 光重合開始剤組成物 |
WO1992018483A1 (en) | 1991-04-22 | 1992-10-29 | Fujisawa Pharmaceutical Co., Ltd. | Quinoline derivatives |
JPH09227547A (ja) | 1996-02-20 | 1997-09-02 | Mitsui Toatsu Chem Inc | 可視光感光性樹脂組成物およびその用途 |
WO1997035565A1 (fr) | 1996-03-27 | 1997-10-02 | Toray Industries, Inc. | Derives de cetone et usage medicinal |
WO2000020371A1 (en) | 1998-10-07 | 2000-04-13 | Merck Frosst Canada & Co. | Prostaglandin receptor ligands |
WO2001079187A2 (en) | 2000-04-18 | 2001-10-25 | Cytovia, Inc. | Substituted 1,4-thiazepine and analogs and their use as activators of caspases |
JP2002371078A (ja) | 2001-06-12 | 2002-12-26 | Sankyo Co Ltd | キノリン誘導体及びキノロン誘導体 |
JP2003021901A (ja) * | 2001-07-05 | 2003-01-24 | Fuji Photo Film Co Ltd | 感光性平版印刷版の光重合方法 |
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 |
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 |
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 |
WO2005028439A1 (ja) * | 2003-09-17 | 2005-03-31 | Sumitomo Chemical Company, Limited | シンナモイル化合物およびその用途 |
WO2005028463A1 (ja) * | 2003-09-17 | 2005-03-31 | Sumitomo Chemical Company, Limited | シンナモイル化合物およびその用途 |
WO2005028441A1 (ja) * | 2003-09-17 | 2005-03-31 | Sumitomo Chemical Company, Limited | シンナモイル誘導体およびその用途 |
Non-Patent Citations (35)
Title |
---|
AM. J. PATHOL., vol. 158, 2001, pages 1653 - 1663 |
AM. J. PHYSIOL. RENAL PHSIOL., vol. 278, 2000, pages F830 - F838 |
AUTOIMMUNITY, vol. 35, 2002, pages 277 - 282 |
CARDIOVASC. PATHOL., vol. 13, 2004, pages 119 |
CLIN. LIVER DIS., vol. 7, 2003, pages 195 - 210 |
CLIN. NEPHROL., vol. 44, 1995, pages 211 |
DIABETES, vol. 45, 1996, pages 522 - 530 |
DIMROTH P. ET AL.: "Reaction of diketene with acetoacetamides", LIEBIGS ANNALEN DER CHEMIE, vol. D, no. 6, 1979, pages 769 - 775, XP003003337 * |
HAGGARTY S.J. ET AL.: "Small Molecule Modulation of the Human Chromatid Decatenation Checkpoint", CHEMISTRY & BIOLOGY, vol. 10, no. 12, 2003, pages 1267 - 1279, XP003003333 * |
HASSAN M.A. ET AL.: "Synthesis and reactions of polysubstituted 2(1H)pyridones and pyridines", REVUE ROUMAINE DE CHIMIE, vol. 27, no. 8, 1982, pages 963 - 967, XP003003335 * |
J. AM. SOC. NEPHROL., vol. 15, 2004, pages 2637 |
J. HEPATOL., vol. 29, 1998, pages 263 |
J. HEPATOL., vol. 37, 2002, pages 331 - 339 |
J. HETEROCYCLIC CHEM., vol. 18, no. 3, 1981, pages 603 |
J. INVEST. DERMATOL., vol. 118, 2001, pages 461 - 470 |
J. INVEST. DERMATOL., vol. 94, 1990, pages 365 |
J. MEDICINAL CHEM., vol. 44, 2001, pages 362 |
J. ORGANIC CHEM., vol. 30, 1965, pages 2241 |
KIDNEY INT., vol. 60, 2001, pages 1745 - 1755 |
KIDNEY INT., vol. 64., 2003, pages 149 - 159 |
LAB. INVEST., vol. 63, 1990, pages 171 |
LEVAI A. ET AL.: "Dimethyldioxirane epoxidation of 3-aryl-1-(3-coumarinyl)propen-1-ones", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 41, no. 5, 2004, pages 707 - 709, XP003003332 * |
LIEBIGS ANNALEN DER CHEMIE, vol. D, no. 6, 1979, pages 769 |
LIFE SCI., vol. 71, 2002, pages 1559 - 1606 |
OGANESIAN E.T. ET AL.: "Electronic structure-activity relationships (ESAR) in propene derivatives. 1,4-Carboxyvinylenechalcones and 3-cinnamoylcoumarins", KHIMIKO-FARMATSEVTICHESKII ZHURNAL, vol. 28, no. 11, 1994, pages 36 - 43, XP003003334 * |
POLISH J. CHEM., vol. 56, no. 2, 1982, pages 419 |
POLYAKOV V.K. ET AL.: "Analogs of chalcones from substituted 3-formyland 3-acetylchromones", UKRAINSKII KHIMICHESKII ZHURANL (RUSSIAN EDITION), vol. 48, no. 7, 1982, pages 772 - 775, XP003003336 * |
PROC. NATL. ACAD. SCI. USA, vol. 88, 1991, pages 6642 |
PROC. NATL. ACAD. SCI. USA, vol. 96, 1999, pages 12719 - 12724 |
PROC. NATL. ACAD. SCI. USA, vol. 97, 2000, pages 8015 - 8020 |
See also references of EP1857104A4 * |
SYNTHESIS, 1981, pages 165 |
SYNTHETIC COMMUNICATION, vol. 16, no. 10, 1986, pages 1195 |
TETRAHEDERON, vol. 53, no. 47, 1997, pages 16061 |
UKRAINSKII KHIMICHESKII ZHURNAL, vol. 48, no. 7, 1982, pages 772 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007132948A1 (ja) * | 2006-05-17 | 2007-11-22 | Sumitomo Chemical Company, Limited | シンナモイル化合物及びその用途 |
WO2007132945A1 (ja) * | 2006-05-17 | 2007-11-22 | Sumitomo Chemical Company, Limited | シンナモイル化合物及びその用途 |
WO2007136125A1 (ja) * | 2006-05-22 | 2007-11-29 | Sumitomo Chemical Company, Limited | 含複素環化合物及びその用途 |
Also Published As
Publication number | Publication date |
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US20090143368A1 (en) | 2009-06-04 |
AU2006219222A1 (en) | 2006-09-08 |
EP1857104A1 (en) | 2007-11-21 |
EP1857104A4 (en) | 2011-03-23 |
CA2600287A1 (en) | 2006-09-08 |
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