US 7,691,883 B2Granted

Cinnamoyl compound and use of the same

AssigneeSumitomo Chemical Company, Limited

InventorsYoshitaka Tomigahara, Kiyoshi Higashi, Junya Takahashi, Chizuko Takahashi

Life of this patent

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Abstract

The present invention relates to a cinnamoyl compound represented by the formula (I):

Claims27

Dependent claims

A cinnamoyl compound represented by the formula (I):

wherein:
(I) A represents a phenyl ring or a pyridyl ring;
and in (Yα)q, Yα is a substituent on a carbon atom and represents a group included in the following X0 group or Y0 group, q represents 0, 1, 2, 3 or 4, and Yαs are the same or different when q is 2 or more and the adjacent two same or different Yαs together may form a group included in the Z0 group to be fused to the A ring when q is 2 or more;
and in (Xα)p, Xα is a substituent on a carbon atom and represents a3-1-CH2—CO—NH- (wherein a3-1 represents a C1-C10 alkoxy group), p represents 1, 2, 3, 4 or 5, and Xαs may be the same or different when p is 2 or more;
and the sum of p and q is 5 or less;
(1) the X0 group:
a Ma-group, wherein Ma represents a Rb- group (wherein Rb represents a C1-C10 alkyl group optionally substituted with a halogen atom), a halogen atom, a nitro group, a cyano group, a hydroxy group, a Rc—Ba—Rd- group (wherein Rc represents a C1-C10 alkyl group optionally substituted with a halogen atom, Ba represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and Rd represents a single bond or a C1-C10 alkylene group), a HORd- group (wherein Rd is as defined above), a Re—CO—Rd- group (wherein Re represents a hydrogen atom, or a C1-C10 alkyl group optionally substituted with a halogen atom, and Rd is as defined above), a Re—CO—O—Rd- group (wherein Re and Rd are as defined above), a ReO—CO—Rd- group (wherein Re and Rd are as defined above), a HO—CO—CH═CH- group, a ReRe′N—Rd- group (wherein Re and Re′ are the same or different, Re is as defined above, Re′ has the same meaning as Re has, and Rd is as defined above), a Re—CO—NRe′—Rd- group (wherein Re, Re′ and Rd are as defined above), a RbO—CO—N(Re)—Rd- group (wherein Rb, Re and Rd are as defined above), a ReRe′N—CO—Rd- group (wherein Re, Re′ and Rd are as defined above), a ReRe′N—CO—NRe″—Rd— group (wherein Re, Re′ and Re″ are the same or different, Re and Re′ are as defined above, Re″ has the same meaning as Re has, and Rd is as defined above), a ReRe′N—C(═NRe″)—NRe′″—Rd- group (wherein Re, Re′, Re″ and Re′″ are the same or different, Re, Re′ and Re″ are as defined above, Re′″ has the same meaning as Re has, and Rd is as defined above), a Rb—SO2—NRe—Rd— group (wherein Rb, Re and Rd are as defined above), a ReRe′N—SO2—Rd— group (wherein Re, Re′ and Rd are as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl group;
(2) the Y0 group:
a Mb0-Rd- group, wherein Mb0 represents a Mc0-group
wherein Mco represents a Mdo-Rd′- group (wherein Mdo represents a 6 to 10-membered aryl group optionally substituted with a Ma- group (wherein Ma is as defined above), a 5 to 10-membered heteroaryl group optionally substituted with a Ma- group (wherein Ma is as defined above), a 3 to 10-membered cyclic hydrocarbon or heterocyclic group optionally substituted with a Ma- group (wherein Ma is as defined above) and optionally containing an unsaturated bond, a (b0)- group
(in the (b0)- group, G0 forms an optionally substituted, saturated or unsaturated, nonaromatic 5 to 14-membered cyclic hydrocarbon or heterocyclic ring), a (c0)- group
(in the (C0)- group, J0 forms a 5 to 7-membered aromatic ring optionally containing a nitrogen atom), a (d0)- group
(wherein d0 forms a 5 to 12-membered hydrocarbon ring which is substituted with a carbonyl group or a thiocarbonyl group and further which may be optionally substituted with an oxy group, a thio group, a —NR1- group {wherein R1 represents a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkyl group substituted with a halogen atom or a R2—B1- group (wherein R2 represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group, and B1 represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group), a C3-C10 alkenyl group, or a C3-C10 alkynyl group}, a sulfinyl group or a sulfonyl group) or a(e0)- group
{wherein e0 forms a 5 to 12-membered hydrocarbon ring optionally substituted with a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR1- group (wherein R1 is as defined above), a sulfinyl group or a sulfonyl group};
and Rd′ is the same as or different from Rd and has the same meaning as Rd has)),
a Mc0-Ba- group (wherein Mc0 and Ba are as defined above), a Mc0-CO- group (wherein Mc0 is as defined above), a Mc0-CO—O- group (wherein Mc0 is as defined above), a Mc0O—CO- group (wherein Mc0 is as defined above), a Mc0ReN- group (wherein Mc0 and Re are as defined above), a Mc0-CO—NRe- group (wherein Mc0 and Re are as defined above), a Mc0O—CO—NRe- group (wherein Mc0 and Re are as defined above), a Mc0ReN—CO- group (wherein Mc0 and Re are as defined above), a Mc0ReN—CO—NRe′- group (wherein Mc0, Re and Re′ are as defined above), a Mc0ReN—C(═NRe′)—NRe″- group (wherein Mc0, Re, Re′ and Re″ are as defined above), a Mc0-SO2—NRe- group (wherein Mc0 and Re are as defined above) or a Mc0ReN—SO2- group (wherein Mc0 and Re are as defined above), and
Rd is as defined above;
(3) the Z0 group:
a 5 to 12-membered cyclic hydrocarbon or heterocyclic ring optionally substituted with a halogen atom, a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, a C3-C10 alkynyloxy group, a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a sulfinyl group or a sulfonyl group, which is an aromatic or nonaromatic and monocyclic or fused ring and which is fused to the A ring;
(II) Qα represents an optionally substituted hydroxy group, or an optionally substituted amino group;
(III) Kα and Lα are the same or different, and represent a hydrogen atom, or a substituent on a carbon atom, or Kα and Lα may form a C1-C10 alkylene group optionally having a substituent or a C1-C10 alkenylene group optionally having a substituent;
and
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

20 more elements

A cinnamoyl compound represented by the formula (II):

wherein:
(I) A represents a phenyl ring or a pyridyl ring;
(II) in (XA0)p, XA0 is a substituent on a carbon atom and represents a3-1-CH2—CO—NH— (wherein a3-1 represents a C1-C10 alkoxy group) and p represents 1, 2, 3, 4 or 5, and when p is 2 or more, XA0s are the same or different;
(III) in (YA0)q, YA0 is a substituent on a carbon atom and represents a group included in the following X0 group and Y0 group, q represents 0, 1, 2, 3 or 4, the sum of p (wherein p is as defined above) and q is 5 or less, YA0s are the same as or different when q is 2 or more, and the adjacent two same or different YA0s may form a group included in the Z0 group to be fused to the A ring when q is 2 or more;
(1) the X0 group:
a Ma- group, wherein Ma represents a Rb- group (wherein Rb represents a C1-C10 alkyl group optionally substituted with a halogen atom), a halogen atom, a nitro group, a cyano group, a hydroxy group, a Rc—Ba—Rd- group (wherein Rc represents a C1-C10 alkyl group optionally substituted with a halogen atom, Ba represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and Rd represents a single bond or a C1-C10 alkylene group), a HORd- group (wherein Rd is as defined above), a Re—CO—Rd- group (wherein Re represents a hydrogen atom, or a C1-C10 alkyl group optionally substituted with a halogen atom, and Rd is as defined above), a Re—CO—O—Rd- group (wherein Re and Rd are as defined above), a ReO—CO—Rd- group (wherein Re and Rd are as defined above), a HO—CO—CH═CH- group, a ReRe′N—Rd- group (wherein Re and Re′ are the same or different, Re is as defined above, Re′ has the same meaning as Re has, and Rd is as defined above), a Re—CO—NRe′—Rd- group (wherein Re, Re′ and Rd are as defined above), a RbO—CO—N(Re)—Rd- group (wherein Rb, Re and Rd are as defined above), a ReRe′N—CO—Rd- group (wherein Re, Re′ and Rd are as defined above), a ReRe′N—CO—NRe″—Rd- group (wherein Re, Re′ and Re″ are the same or different, Re and Re′ are as defined above, Re″ has the same meaning as Re has, and Rd is as defined above), a ReRe′N—C(═NRe″)—NRe′″—Rd- group (wherein Re, Re′, Re″ and Re′″ are the same or different, Re, Re′ and Re″ are as defined above, Re′″ has the same meaning as Re has, and Rd is as defined above), a Rb—SO2—NRe—Rd- group (wherein Rb, Re and Rd are as defined above), a ReRe′N—SO2—Rd- group (wherein Re, Re′ and Rd are as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl group;
(2) the Y0 group:
a Mb0-Rd- group, wherein Mb0 represents a Mc0- group (wherein Mc0 represents a Md0-Rd′- group (wherein Md0 represents a 6 to 10-membered aryl group optionally substituted with a Ma- group (wherein Ma is as defined above), a 5 to 10-membered heteroaryl group optionally substituted with a Ma- group (wherein Ma is as defined above), a 3 to 10-membered cyclic hydrocarbon or heterocyclic group which is optionally substituted with a Ma- group (wherein Ma is as defined above) and which optionally contains an unsaturated bond, or a (bo)- group
(wherein (bo) forms as defined above), a (co)- group
(wherein (co) forms as defined above), a (do)- group
{wherein do forms a 5 to 12-membered hydrocarbon ring which is substituted with a carbonyl group or a thiocarbonyl group and further which may be optionally substituted with an oxy group, a thio group, a —NR1- group (wherein R1 is a hydrogen atom, or a C1-C10 alkyl group, or a C2-C10 alkyl group substituted with a halogen atom or a R2—B1-group (wherein R2 represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alknyl group, and B1 represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group), or a C3-C10 alkenyl group, or a C3-C10 alkynyl group), a sulfinyl group or a sulfonyl group} or a (e0)- group
{wherein e0 forms a 5 to 12-membered hydrocarbon ring optionally substituted with a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR1- group (wherein R1 is as defined above), a sulfinyl group or a sulfonyl group}, and Rd′ is the same as or different from Rd and has the same meaning as Rd has)),
a Mc0-Ba- group (wherein Mc0 and Ba are as defined above), a Mc0-CO- group (wherein Mc0 is as defined above), a Mc0-CO—O- group (wherein Mc0 is as defined above), a Mc0O—CO- group (wherein Mc0 is as defined above), a Mc0ReN- group (wherein Mc0 and Re are as defined above), a Mc0-CO—NRe- group (wherein Mc0 and Re are as defined above), a Mc0O—CO—NRe- group (wherein Mc0 and Re are as defined above), a Mc0ReN—CO- group (wherein Mc0 and Re are as defined above), a Mc0ReN—CO—NRe′- group (wherein Mc0, Re and Re′ are as defined above), a Mc0ReN—C(═NRe′)—NRe″- group (wherein Mc0, Re, Re′ and Re″ are as defined above), a Mc0-SO2—NRe- group (wherein Mc0 and Re are as defined above) or a Mc0ReN—SO2- group (wherein Mco and Re are as defined above), and
Rd is as defined above;
(3) the Z0 group:
a 5 to 12-membered cyclic hydrocarbon or heterocyclic ring optionally substituted with a halogen atom, a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, a C3-C10 alkynyloxy group, a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a sulfinyl group or a sulfonyl group, which is an aromatic or nonaromatic and monocyclic or fused ring and which is fused to the A ring;
(IV) QA0 represents a hydroxyl group, a (b0)- group (wherein (b0) is as defined above), an A9-B6—Be- group (wherein A9 and B6 are as defined above, and Bc represent an oxy group or a —N((O)mR1)- group (wherein m and R1 are as defined above), provided that Bc is not a sulfonyl group when A9 is a hydrogen atom), an A7″-SO2—Bc- group (wherein A7″ and Bc are as defined above), an A8-SO2—Bc- group (wherein A8 and Bc are as defined above, provided that A8 is not a hydrogen atom), a R1R1′N—SO2—Bc- group (wherein R1, R1′ and Bc are as defined above), a (b0)-SO2—Bc- group (wherein (b0) and Bc are as defined above), an A9′-Bc- group (wherein A9′ and Bc are as defined above), a D5-R4—Bc- group (wherein D5, R4 and Bc are as defined above), a Mc0-B3—Bc- group (wherein Mc0, B3 and Bc are as defined above) or a Mc0-Bc- group (wherein Mc0 and Bc are as defined above);
(V) KA0 represents a hydrogen atom, a halogen atom, or a C10 alkyl group, LA0 represents a hydrogen atom, or a Mb0-group (Mb0 is as defined above), or KA0 and LA0 may form a C1-C10 alkylene group, or a C1-C10 alkenylene group optionally substituted with single or the same or different plural Ma groups;
and
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

17 more elements

A cinnamoyl compound represented by the formula (III):

wherein:
(I) A represents a phenyl ring or a pyridyl ring;
(II) in (XA)p, XA is a substituent on a carbon atom and represents a3-1-CH2—CO—NH— (wherein a3-1 represents a C1-C10 alkoxy group) and p represents 1, 2, 3, 4 or 5, and XAs are the same or different when p is 2 or more;
(III) in (YA)q, YA is a substituent on a carbon atom and represents a group included in the following X group or Y group, q represents 0, 1, 2, 3 or 4, the sum of p (wherein p is as defined above) and q is 5 or less, YAs are the same or different when q is 2 or more, and the adjacent two same or different YAs together may form a group included in the Z group to be fused to the A ring when q is 2 or more,
(1) the X group:
a Ma- group
wherein Ma represents a Rb- group (wherein Rb represents a C1-C10 alkyl group optionally substituted with a halogen atom), a halogen atom, a nitro group, a cyano group, a Rc—Ba—Rd- group (wherein Rc represents a C1-C10 alkyl group optionally substituted with a halogen atom, Ba represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and Rd represents a single bond or a C1-C10 alkylene group), a HORd- group (wherein Rd is as defined above), a Re—CO—Rd- group (wherein Re represents a hydrogen atom, or a C1-C10 alkyl group optionally substituted with a halogen atom, and Rd is as defined above), a Re—CO—O—Rd- group (wherein Re and Rd are as defined above), a ReO—CO—Rd- group (wherein Re and Rd are as defined above), a HO—CO—CH═CH- group, a ReRe′N—Rd- group (wherein Re and Re′ are the same or different, Re is as defined above, Re′ has the same meaning as Re has, and Rd is as defined above), a Re—CO—NRe′—Rd- group (wherein Re, Re′ and Rd are as defined above), a RbO—CO—N(Re)—Rd- group (wherein Rb, Re and Rd are as defined above), a ReRe′N—CO—Rd- group (wherein Re, Re′ and Rd are as defined above), a ReRe′N—CO—NRe″—Rd- group (wherein Re, Re′ and Re″ are the same or different, Re and Re′ are as defined above, Re″ has the same meaning as Re has, and Rd is as defined above), a ReRe′N—C(═NRe″)—NRe′″—Rd- group (wherein Re, Re′, Re″ and Re′″are the same or different, Re, Re′ and Re″ are as defined above, Re′″ has the same meaning as Re has, and Rd is as defined above), a Rb—SO2—NRe—Rd- group (wherein Rb, Re and Rd are as defined above), a ReRe′N—SO2—Rd- group (wherein Re, Re′ and Rd are as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl group;
(2) the Y group:
a Mb-Rd-group, wherein Mb represents a Mc-group
(wherein Mc represents a Md-Rd′- group (wherein Md represents a phenyl group optionally substituted with a Ma- group (wherein Ma is as defined above), a pyridyl group optionally substituted with a Ma- group (wherein Ma is as defined above), a naphthyl group optionally substituted with a Ma- group (wherein Ma is as defined above), a (b)- group (wherein (b) is as defined above), a (c)- group (wherein (c) is as defined above), a (d)- group
(wherein 1 is 2, 3 or 4, Bb represents an oxy group or a thio group) or an (e)- group
(wherein 1 and Bb are as defined above), and Rd′ is the same as or different from Rd and has the same meaning as Rd has)),
a Mc-Ba- group (wherein Mc and Ba are as defined above), a Mc-CO- group (wherein Mc is as defined above), a Mc-CO—O- group (wherein Mc is as defined above), a McO—CO- group (wherein Mc is as defined above), a McReN- group (wherein Me and Re are as defined above), a Mc—CO—NRe- group (wherein Mc and Re are as defined above), a Mc—CO—NRe- group (wherein Mc and Re are as defined above), a McReN—CO- group (wherein Mc and Re are as defined above), a McReN—CO—NRe′- group (wherein Mc, Re and Re′ are as defined above), a McReN—C(═NRe′)—NRc″- group (wherein Mc, Re, Re′ and Re″ are as defined above), a Mc—SO2—NRe- group (wherein Mc and Re are as defined above) or a McReN—SO2- group (wherein Mc and Re are as defined above), and
Rd is as defined above;
(3) the Z group:
a —N═C(Ya)—Ya′- group (wherein Ya represents a hydrogen atom, or a C1-C10 alkyl group optionally substituted with a halogen atom, or a C1-C10 alkoxy group, and Ya′ represents an oxy group, a thio group, or an imino group optionally substituted with a C1-C10 alkyl group),
a —Yb—Yb′—Yb″- group (wherein Yb and Yb″ are the same or different, and represent a methylene group, an oxy group, a thio group, a sulfinyl group, or an imino group optionally substituted with a C1-C10 alkyl group, and Yb′ represents a C1-C4 alkylene group optionally substituted with a halogen atom, or a C1-C4 alkylene group optionally having an oxo group) or
a —Yc—O—Yc′—O- group (wherein Yc and Yc′ are the same or different, and represent a C1-C10 alkylene group);
(IV) QA represents a hydroxyl group, a (b)- group (wherein (b) is as defined above), an A9-B6—Bc- group (wherein A9 and B6 are as defined above, and Bc represents an oxy group or a —N((O)mR1)- group (wherein m and R1 are as defined above), provided that Bc is not a sulfonyl group when A9 is a hydrogen atom), an A7″-SO2—Bc- group (wherein A7″ and Bc are as defined above), an A8-SO2—Bc- group (wherein A8 and Bc are as defined above, provided that A8 is not a hydrogen atom), a R1R1′N—SO2—Bc- group (wherein R1, R1′ and Bc are as defined above), a (b)-SO2—Bc- group (wherein (b) and Bc are as defined above), an A9′-Bc- group (wherein A9′ and Bc are as defined above), a D5-Rc—Bc- group (wherein D5, R4 and Bc are as defined above), a Mc-B3—Bc- group (wherein Mc, B3 and Bc are as defined above) or a Mc-Bc- group (wherein Mc and Bc are as defined above);
(V) KA represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, LA represents a hydrogen atom, a C1-C10 alkyl group or a Mb-group (Mb is as defined above), or KA and LA may form a C1-C10 alkylene group or a —C(Ma′)=C(Ma″)-C(Ma′″)=C(Ma″″)- group (Ma′, Ma″, Ma′″ and Ma″″ are the same or different, are the same as or different from Ma, and represent a hydrogen atom or Ma);
and
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

19 more elements

A cinnamoyl compound represented by the formula (IV):

wherein:
A represents a phenyl ring or a pyridyl ring,
Xa is a substituent on a carbon atom, and represents a3-1-CH2—CO—NH— (wherein a3-1 represents a C1-C10 alkoxy group)
p represents 1, 2 or 3, and when p is 2 or more, Xas are the same or different;
Ya represents a halogen atom, a nitro group, a r0CO—NH- group (wherein r0 is a C1-C10 alkyl group), a C1-C10 alkyl group or a C1-C10 alkoxy group;
q represents 0, 1 or 2, and when q is 2 or more, Yas are the same or different;
qa represents a ra-O- group {wherein ra represents a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a C1-C10 alkyl group substituted with a r0r0′N—CH2- group (wherein r0 is as defined above and r0′ is the same as the different from r0 and has the same meaning as r0 has), a rOCH2- group (wherein r is a hydrogen atom or a C1-C10 alkyl group), a r0-CO- group (wherein r0 is as defined above), a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or a cyano group, or a r3-r1- group (wherein r3 represents a phenyl group or a pyridyl group, and r1 is a C1-C10 alkylene group)};
a piperidino group;
a morpholino group;
or a r4r4′N- group (wherein r4 and r4′ are the same or different, and represent a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, provided that r4 and r4′ are not a hydrogen atom at the same time);
Ka represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, and La represents a hydrogen atom or a C1-C10 alkyl group;
or
Ka and La together may form a C1-C10 alkylene group or a 1,3-butadienylene group;
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

11 more elements

A cinnamoyl compound represented by the formula (V):

wherein:
a represents a phenyl ring or a pyridyl ring;
x represents a methine group or a nitrogen atom;
Xa is a substituent on a carbon atom, and represents a3-1-CH2—CO—NH- (wherein a3-1 represents a C1-C10 alkoxy group)
p represents 1, 2 or 3, and when p is 2 or more, Xas are the same or different;
Ya represents a halogen atom, a nitro group, a r0CO—NH- group (wherein r0 a C1-C10 alkyl group), a C1-C10 alkyl group or a C1-C10 alkoxy group;
q represents 0, 1 or 2, and when q is 2 or more, Yas are the same or different;
qa represents a ra-O- group {wherein ra represents a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a C1-C10 alkyl group substituted with a r0r0′N—CH2- group (wherein r0 is as defined above and r0′ is the same as the different from r0 and has the same meaning as r0 has), a rOCH2- group (wherein r is a hydrogen atom or a C1-C10 alkylene group), a r0-CO- group (wherein r0 is as defined above), a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or a cyano group, or a r3-r1- group (wherein r3 represents a phenyl group or a pyridyl group, and r1 is a C1-C10 alkylene group)};
a piperidino group;
a morpholino group;
or a r4r4′N- group (wherein r4 and r4′ are the same or different, and represent a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, provided that r4 and r4′ are not a hydrogen atom at the same time);
ta represents a rb- group (wherein rb is the same as or different from ra, and has the same meaning as ra has) or a r3′- group (wherein r3′ is the same as or different from r3, and has the same meaning as r3 has);
Ka represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, and La represents a hydrogen atom or a C1-C10 alkyl group;
or
Ka and La together may form a C1-C10 alkylene group or a 1,3-butadienylene group;
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

13 more elements

A 2H-1-benzopyran-2-one compound represented by the formula (VIII):

wherein:
a represents a phenyl ring or a pydridyl ring;
x represents a methine group or a nitrogen atom;
Xa is a substituent on a carbon atom, and represents a3-1-CH2—CO—NH— (wherein a3-1 represents a C1-C10 alkoxy group)
p represents 1, 2 or 3, and when p is 2 or more, Xas are the same or different;
Ya represents a halogen atom, a nitro group, a r0CO—NH- group (wherein r0 is a C1-C10 alkyl group), a C1-C10 alkyl group or a C1-C10 alkoxy group;
q represents 0, 1 or 2, and when q is 2 or more, Yas are the same or different;
qa represents a ra-O- group {wherein ra represents a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a C1-C10 alkyl group substituted with a r0r0′N—CH2- group (wherein r0 is as defined above and r0′ is the same as the different from r0 and has the same meaning as r0 has), a rOCH2- group (wherein r is a hydrogen atom or a C1-C10 alkyl group), a r0-CO- group (wherein r0 is as defined above), a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or a cyano group, or a r3-r1- group (wherein r3 represents a phenyl group or a pyridyl group, and r1 is a C1-C10 alkylene group)};
a piperidino group;
a morpholino group;
or a r4r4′N- group (wherein r4 and r4′ are the same or different, and represent a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, provided that r4 and r4′ are not a hydrogen atom at the same time);
ta represents a rb- group (wherein rb is the same as or different from ra, and has the same meaning as ra has) or a r3′- group (wherein r3′ is the same as or different from r3, and has the same meaning as r3 has);
Ka represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, and La represents a hydrogen atom or a C1-C10 alkyl group;
or
Ka and La together may form a C1-C10 alkylene group or a 1,3-butadienylene group;
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

13 more elements

A process for producing a cinnamoyl compound represented by the formula (XLVII″):

wherein A, Xc, Ya, p, q, rc, Ka and La are as defined below, and the term “as defined above (or below)” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above (or below) and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range;
which comprises reacting a cinnamoyl compound represented by the formula (XLVII):
wherein
A represents a phenyl ring or a pyridyl ring,
Xc is a substituent on a carbon atom, and represents a3-1-CH2—CO—N— (wherein a3-1 represents a C1-C10 alkoxy group)
p represents 1, 2 or 3, and when p is 2 more, Xcs are the same or different;
Ya represents a halogen atom, a nitro group, a r0CO—NH- group (wherein r0 is a C1-C10 alkyl group), a C1-C10 alkyl group or a C1-C10 alkoxy group;
q represents 0, 1 or 2, and when q is 2 or more, Yas are the same or different;
Ka represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, and La represents a hydrogen atom or a C1-C10 alkyl group, or
Ka and La together may form a C1-C10 alkylene group or a 1,3-butadienylene group, and
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range, with a compound represented by the formula (XLVII′):
rc-V (XLVII′)
wherein rc represents a tc′- group {wherein tc′ represents a C1-C10 alkyl group;
a C3-C10 alkenyl group;
a C3-C10 alkynyl group;
a C1-C10 alkyl group substituted with a r0r0′N—CH2- group (wherein r0 is as defined above and r0′ is the same as the different from r0 and has the same meaning as r0 has), a rOCH2- group (wherein r is a hydrogen atom or a C1-C10 alkyl group), a r0-CO- group (wherein r0 is as defined above), a C1-C10 alkoxycarbonyl group, an aminocarbonyl group or a cyano group;
or a r3-r1- group (wherein r3 represents a phenyl group or a pyridyl group, and r1 is a C1-C10 alkylene group)}, and V represents a leaving group, and
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

15 more elements

A process for producing a cinnamoyl compound represented by the formula (XLVIII′):

wherein:
A is as defined below,
Xd′ is a substituent on a carbon atom, and represents a3-1-CH2— CO—NH— (wherein a3-1 represents a C1-C10 alkoxy group)
p is as defined below and, and when p is 2 or more, Xd′s are the same or different,
Ya and q are as defined below,
qd′ represents a rd″-O- group {wherein rd″ represents a hydrogen atom;
a C1-C10 alkyl group;
a C3-C10 alkenyl group;
a C3-C10 alkynyl group;
a C1-C10 alkyl group substituted with a r0r0′N—CH2- group (wherein r0 and r0′ are as defined below), a rOCH2- group (wherein r is as defined below), a r0-CO- group (wherein r0 is as defined below), a carboxy group, an aminocarbonyl group or a cyano group;
or a r3-r1- group (wherein r3 represents a phenyl group or a pyridyl group, and r1 is as defined below)}, a piperidino group, a morpholino group, or a r4r4′N- group (wherein r4 and r4′ are as defined below, provided that they are not hydrogen atom at the same time),
Ka and La are as defined below, and
the term “as defined above (or below)” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above (or below) and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range;
which comprises hydrolyzing a cinnamoyl compound represented by the formula (XLVIII):
wherein:
A represents a benzene ring or a pyridine ring,
Xd is a substituent on a carbon atom, and represents an a0d-r1-b-r1′- group {wherein a0d represents a r2O—CO- group (wherein r2 represents a C1-C10 alkyl group, or a C2-C10 alkyl group substituted with a hydroxy group), r1 represents a C1-C10 alkylene group, r1′ represents a single bond or a C1-C10 alkylene group, and b represents an oxy group, a thio group, a sulfinyl group, a sulfonyl group or an imino group}, a r0O—COCO—NH- group (wherein r0 represents a C1-C10 alkyl group), an a3d-z-NH- group (wherein a3d represents a C1-C10 alkyl group substituted with a C1-C10 alkoxycarbonyl group, and z represents a carbonyl group or a sulfonyl group), or an a4d-NHCO- group {wherein a4d represents a C1-C10 alkyl group substituted with a r0O—CO- group (wherein r0 is as defined above), or a r0O—CO-(r0O—COCH2)CH- group (wherein r0 is as defined above)},
p represents 1, 2 or 3, and when p is 2 or more, Xds are the same or different,
Ya represents a halogen atom, a nitro group, a r0CO—NH- group (wherein r0 is as defined above), a C1-C10 alkyl group or a C1-C10 alkoxy group,
q represents 0, 1 or 2, and when q is 2 or more, Ya s are the same or different;
qd represents a rd—O- group {wherein rd represents a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a C1-C10 alkyl group substituted with a r0r0′N—CH2- group (wherein r0 is as defined above, and r0′is the same as or different from r0 and has the same meaning as r0 has), a rOCH2- group (wherein r is as defined above), a r0-CO- group (wherein r0 is as defined above), a C1-C10 alkoxycarbonyl group, a carboxy group, an aminocarbonyl group or a cyano group, or a r3-r1-group (wherein r3 represents a phenyl group or a pyridyl group, and r1 is as defined above)};
a piperidino group;
a morpholino group;
or a r4r4′N- group (wherein r4 and r4′ represent a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, provided that they are not a hydrogen atom at the same time),
Ka represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, and La represents a hydrogen atom or a C1-C10 alkyl group, or
Ka and La together may form a C1-C10 alkylene group or a 1,3-butadienylene group,
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

24 more elements

A process for producing a cinnamoyl compound represented by the formula (XLIX″):

wherein Xe′ is a substituent on a carbon atom and represents a3-1-CH2—CO—NH— (wherein a3-1 represents a C1-C10 alkoxy group), and A, Ya, p, q, qe, Ka and La are as defined below, and the term “as defined above (or below)” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above (or below) and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range;
which comprises reacting a cinnamoyl compound represented by the formula (XLIX):
wherein:
A represents a benzene ring or a pyridine ring,
Xe is a substituent on a carbon atom, and represents a H-b″- group (wherein b″ represents an oxy group or a thio group),
p represents 1, 2 or 3 and, when p is 2 or more, Xcs are the same or different,
Ya represents a halogen atom, a nitro group, a r0CO—NH- group (wherein r0 is a C1-C10 alkyl group), a C1-C10 alkyl group or a C1-C10 alkoxy group,
q represents 0, 1 or 2, and when q is 2 or more, Ya s are the same or different;
qe represents a re-O- group {wherein re represents a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, a C1-C10 alkyl group substituted with a r0r0′N—CH2- group (wherein r0 is as defined above, and r0′ is the same as or different from r0 and has the same meaning as r0 has), a rOCH2- group (wherein r represents a hydrogen atom or a C1-C10 alkyl group), a r0-CO- group (wherein r0 is as defined above), a C1-C10 alkoxycarbonyl group, an aminocarbonyl group or a cyano group, or a r3-r1- group (wherein r3 represents a phenyl group or a pyridyl group, and r1 represents a C1-C10 alkylene group)};
a piperidino group;
a morpholino group;
or a r4r4′N- group (wherein r4 and r4′ represent a hydrogen atom, a C1-C10 alkyl group, a C3-C10 alkenyl group, a C3-C10 alkynyl group, or a C2-C10 alkyl group substituted with a C1-C10 alkoxy group, provided that they are not a hydrogen atom at the same time),
Ka represents a hydrogen atom, a halogen atom or a C1-C10 alkyl group, and La represents a hydrogen atom or a C1-C10 alkyl group, or
Ka and La together may form a C1-C10 alkylene group or a 1,3-butadienylene group, and
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range,
with a compound represented by the formula (XLIX′):
a0e-r1″-V′ (XLIX′)
wherein
a0e represents a methyl group substituted with a C1-C10 alkylthio group, a methyl group substituted with a C1-C10 alkylsulfinyl group, a methyl group substituted with a C1-C10 alkylsulfonyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a r2O—CO- group (wherein r2 represents a C1-C10 alkyl group, or a C2-C10 alkyl group substituted with a hydroxy group), a rr′N—CO- group (wherein r and r′ are the same or different, and represent a hydrogen atom or a C1-C10 alkyl group), an a1-NH—CO- group (wherein a1 represents a C2-C10 alkyl group substituted with a C1-C10 alkoxy group), an a1′-CO- group (wherein a1′ represents a morpholino group), a rr′N—CH2- group (wherein r is as defined above, r′ is the same as or different from r and has the same meaning as r has), a r0-(O)1—CONH—CH2- group (wherein r0 is as defined above, and l represents 0 or 1), a r-OCH2- group (wherein r is as defined above), a r0—CO- group (wherein r0 is as defined above) or a cyano group,
r1″ is the same as or different from r1 and has the same meaning as r1 has, and V′ represents a leaving group or a hydroxy group, or 1,3-propanesultone or 1,4-butanesultone
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

18 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/572,639Filed 16 Sep 2004
Priority: JP 2003-32414917 Sep 2003
Published: US 2007/0265228 A115 Nov 2007
Granted: 6 Apr 2010
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07C 47/55
Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings: containing halogen
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 9/12
Drugs for disorders of the cardiovascular system: antihypertensives

Family

US 2007/0265228 A1Pre-grant publication · published 15 Nov 2007
US 7,691,883 B2This patent

From the US filing history. Foreign family members aren’t listed.

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A cinnamoyl compound represented by the formula (I):

wherein:
(I) A represents a phenyl ring or a pyridyl ring;
and in (Yα)q, Yα is a substituent on a carbon atom and represents a group included in the following X0 group or Y0 group, q represents 0, 1, 2, 3 or 4, and Yαs are the same or different when q is 2 or more and the adjacent two same or different Yαs together may form a group included in the Z0 group to be fused to the A ring when q is 2 or more;
and in (Xα)p, Xα is a substituent on a carbon atom and represents a3-1-CH2—CO—NH- (wherein a3-1 represents a C1-C10 alkoxy group), p represents 1, 2, 3, 4 or 5, and Xαs may be the same or different when p is 2 or more;
and the sum of p and q is 5 or less;
(1) the X0 group:
a Ma-group, wherein Ma represents a Rb- group (wherein Rb represents a C1-C10 alkyl group optionally substituted with a halogen atom), a halogen atom, a nitro group, a cyano group, a hydroxy group, a Rc—Ba—Rd- group (wherein Rc represents a C1-C10 alkyl group optionally substituted with a halogen atom, Ba represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group, and Rd represents a single bond or a C1-C10 alkylene group), a HORd- group (wherein Rd is as defined above), a Re—CO—Rd- group (wherein Re represents a hydrogen atom, or a C1-C10 alkyl group optionally substituted with a halogen atom, and Rd is as defined above), a Re—CO—O—Rd- group (wherein Re and Rd are as defined above), a ReO—CO—Rd- group (wherein Re and Rd are as defined above), a HO—CO—CH═CH- group, a ReRe′N—Rd- group (wherein Re and Re′ are the same or different, Re is as defined above, Re′ has the same meaning as Re has, and Rd is as defined above), a Re—CO—NRe′—Rd- group (wherein Re, Re′ and Rd are as defined above), a RbO—CO—N(Re)—Rd- group (wherein Rb, Re and Rd are as defined above), a ReRe′N—CO—Rd- group (wherein Re, Re′ and Rd are as defined above), a ReRe′N—CO—NRe″—Rd— group (wherein Re, Re′ and Re″ are the same or different, Re and Re′ are as defined above, Re″ has the same meaning as Re has, and Rd is as defined above), a ReRe′N—C(═NRe″)—NRe′″—Rd- group (wherein Re, Re′, Re″ and Re′″ are the same or different, Re, Re′ and Re″ are as defined above, Re′″ has the same meaning as Re has, and Rd is as defined above), a Rb—SO2—NRe—Rd— group (wherein Rb, Re and Rd are as defined above), a ReRe′N—SO2—Rd— group (wherein Re, Re′ and Rd are as defined above), a C2-C10 alkenyl group or a C2-C10 alkynyl group;
(2) the Y0 group:
a Mb0-Rd- group, wherein Mb0 represents a Mc0-group
wherein Mco represents a Mdo-Rd′- group (wherein Mdo represents a 6 to 10-membered aryl group optionally substituted with a Ma- group (wherein Ma is as defined above), a 5 to 10-membered heteroaryl group optionally substituted with a Ma- group (wherein Ma is as defined above), a 3 to 10-membered cyclic hydrocarbon or heterocyclic group optionally substituted with a Ma- group (wherein Ma is as defined above) and optionally containing an unsaturated bond, a (b0)- group
(in the (b0)- group, G0 forms an optionally substituted, saturated or unsaturated, nonaromatic 5 to 14-membered cyclic hydrocarbon or heterocyclic ring), a (c0)- group
(in the (C0)- group, J0 forms a 5 to 7-membered aromatic ring optionally containing a nitrogen atom), a (d0)- group
(wherein d0 forms a 5 to 12-membered hydrocarbon ring which is substituted with a carbonyl group or a thiocarbonyl group and further which may be optionally substituted with an oxy group, a thio group, a —NR1- group {wherein R1 represents a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkyl group substituted with a halogen atom or a R2—B1- group (wherein R2 represents a C1-C10 alkyl group, a C3-C10 alkenyl group or a C3-C10 alkynyl group, and B1 represents an oxy group, a thio group, a sulfinyl group or a sulfonyl group), a C3-C10 alkenyl group, or a C3-C10 alkynyl group}, a sulfinyl group or a sulfonyl group) or a(e0)- group
{wherein e0 forms a 5 to 12-membered hydrocarbon ring optionally substituted with a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a —NR1- group (wherein R1 is as defined above), a sulfinyl group or a sulfonyl group};
and Rd′ is the same as or different from Rd and has the same meaning as Rd has)),
a Mc0-Ba- group (wherein Mc0 and Ba are as defined above), a Mc0-CO- group (wherein Mc0 is as defined above), a Mc0-CO—O- group (wherein Mc0 is as defined above), a Mc0O—CO- group (wherein Mc0 is as defined above), a Mc0ReN- group (wherein Mc0 and Re are as defined above), a Mc0-CO—NRe- group (wherein Mc0 and Re are as defined above), a Mc0O—CO—NRe- group (wherein Mc0 and Re are as defined above), a Mc0ReN—CO- group (wherein Mc0 and Re are as defined above), a Mc0ReN—CO—NRe′- group (wherein Mc0, Re and Re′ are as defined above), a Mc0ReN—C(═NRe′)—NRe″- group (wherein Mc0, Re, Re′ and Re″ are as defined above), a Mc0-SO2—NRe- group (wherein Mc0 and Re are as defined above) or a Mc0ReN—SO2- group (wherein Mc0 and Re are as defined above), and
Rd is as defined above;
(3) the Z0 group:
a 5 to 12-membered cyclic hydrocarbon or heterocyclic ring optionally substituted with a halogen atom, a C1-C10 alkoxy group, a C3-C10 alkenyloxy group, a C3-C10 alkynyloxy group, a carbonyl group, a thiocarbonyl group, an oxy group, a thio group, a sulfinyl group or a sulfonyl group, which is an aromatic or nonaromatic and monocyclic or fused ring and which is fused to the A ring;
(II) Qα represents an optionally substituted hydroxy group, or an optionally substituted amino group;
(III) Kα and Lα are the same or different, and represent a hydrogen atom, or a substituent on a carbon atom, or Kα and Lα may form a C1-C10 alkylene group optionally having a substituent or a C1-C10 alkenylene group optionally having a substituent;
and
the term “as defined above” used for the same symbols among plural substituents means that the plural substituents independently represent the same meaning as that described above and, among the plural substituents, although the selection range of substituents to be selected is the same, selected substituents may be the same or different as long as they are selected within the range.

20 more elements

Facts

Application

10/572,639Filed 16 Sep 2004

Priority

JP 2003-32414917 Sep 2003

Published

US 2007/0265228 A115 Nov 2007

Granted

6 Apr 2010

Term ends

Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07C 47/55
Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings: containing halogen
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 9/12
Drugs for disorders of the cardiovascular system: antihypertensives