# US 9,040,709 B2 · Method for producing pyridazinone compounds and intermediate thereof

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- Number: US 9,040,709 B2
- Document ID: US9040709B2
- Status: Granted
- Kind: B2
- Application number: 14/483,508
- Filed: 2014-09-11
- Published: 2014-12-25
- Granted: 2015-05-26
- Earliest claimed: 2010-09-08
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Sumitomo Chemical Company, Limited
- Inventors: Markus Jachmann; Takayuki Wakamatsu; Mitsuharu Anryu
- Web page: https://patentgrep.com/patent/US9040709B2

## CPC

- C07C 323/48: to nitrogen atoms
- A61P 33/00: Antiparasitic agents
- C07C 59/84: containing six membered aromatic rings
- C07C 59/88: containing halogen
- C07C 69/738: Esters of keto-carboxylic acids {or aldehydo-carboxylic acids}
- C07C 243/32: the carbon skeleton containing rings
- C07C 251/76: to carbon atoms of a saturated carbon skeleton
- C07C 315/04: by reactions not involving the formation of sulfone or sulfoxide groups
- C07C 317/28: with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C 319/20: by reactions not involving the formation of sulfide groups
- C07D 209/18: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 209/24: with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
- C07D 213/56: Amides
- C07D 237/16: Two oxygen atoms
- C07D 237/18: Sulfur atoms
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to a novel method for producing a pyridazinone compound and an intermediate thereof as shown in the following scheme: wherein the symbols are as defined in the specification.

## Claims

### Claim 1

A compound of the formula (4A):
wherein the symbols in the formula (4A) are defined as follows:
R2-4A represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a (C1-C6 alkylsulfinyl)C1-C6 alkyl group, a (C1-C6 alkylsulfonyl)C1-C6 alkyl group, a phenyl group, or a 5- or 6-membered heteroaryl group;
wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the (C1-C6 alkylsulfinyl)C1-C6 alkyl group, and the (C1-C6 alkylsulfonyl)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different, the phenyl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 2-4A, provided that when they have two or more substituents, then the substituents may be same or different;
the Group 2-4A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino group, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
in the Group 2-4A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
R3-4A represents hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a (C1-C6 alkylthio)C1-C6 alkyl group, a C1-C6 alkylsulfonyl group, a (C1-C6 alkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a phenyl group, a benzyl group, or a phenylsulfonyl group;
wherein the C1-C6 alkyl group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the (C1-C6 alkylthio)C1-C6 alkyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same of different; and the phenyl group, the benzyl group, and the phenylsulfonyl group may optionally have one or more substituents selected from Group 3-4A, provided that when they have two or more substituents, then the substituents may be same or different;
the Group 3-4A consists of halogen, a C1-C6 alkyl group, a C1-C6 alkoxy group, and a (C1-C6 alkoxy)C1-C6 alkyl group;
in the Group 3-4A, the C1-C6 alkyl group, the C1-C6 alkoxy group, and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
R5-4A represents a C1-C6 alkyl group or a phenyl group;
wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different; and the phenyl group may optionally have one or more substituents selected from Group 5-4A, provided that when it has two or more substituents, then the substituents may be same or different;
the Group 5-4A consists of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group;
in the Group 5-4A, the C1-C6 alkyl group, and the C1-C6 alkoxy group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different;
G4A represents a C6-C10 aryl group, a 5- or 6-membered heteroaryl group, or an 8- to 10-membered fused heteroaryl group;
wherein the C6-C10 aryl group, the 5- or 6-membered heteroaryl group, and the 8- to 10-membered fused heteroaryl group may optionally have one or more substituents selected from Group R4-4A, provided that when they have two or more substituents, then the substituents may be same or different;
the Group R4-4A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino gout), a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, a tri(C1-C6 alkyl)silyl group, a C6-C10 aryl group, and a 5- or 6-membered heteroaryl group;
in the Group R44A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different; and the C6-C10 aryl group and the 5- or 6-membered heteroaryl group may optionally have one or more substituents selected from Group 4-4A, provided that when they have two or more substituents, then the substituents may be same or different;
the Group 4-4A consists of halogen, a cyano group, a nitro group, a formyl group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a (C1-C6 alkoxy)C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C3-C6 cycloalkyl group, a C1-C6 alkylthio group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C1-C6 alkylamino mow, a di(C1-C6 alkyl)amino group, a C3-C6 cycloalkylamino group, a (C1-C6 alkyl)carbonyl group, a (C3-C6 cycloalkyl)carbonyl group, a (C1-C6 alkoxy)carbonyl group, a (C1-C6 alkylamino)carbonyl group, a di(C1-C6 alkyl)aminocarbonyl group, a (C3-C6 cycloalkylamino)carbonyl group, and a tri(C1-C6 alkyl)silyl group;
in the Group 4-4A, the C1-C6 alkyl group, the C1-C6 alkoxy group, the (C1-C6 alkoxy)C1-C6 alkyl group, the C2-C6 alkenyl group, the C2-C6 alkynyl group, the C3-C6 cycloalkyl group, the C1-C6 alkylthio group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the (C1-C6 alkyl)carbonyl group, the (C3-C6 cycloalkyl)carbonyl group, and the (C1-C6 alkoxy)carbonyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different; and
n represents an integer of 0, 1 or 2.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein G4A is a phenyl group wherein the phenyl group may optionally have one or more substituents selected from the Group R4-4A, provided that when it has two or more substituents, then the substituents may be same or different.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the Group R4-4A is Group R4-4A-1;
wherein the Group R4-4A-1 consists of halogen, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, a C2-C6 alkynyl group, and a phenyl group;
in the Group R4-4A-1, the C1-C6 alkyl group, the C1-C6 alkoxy group, the C3-C6 cycloalkyl group, and the C2-C6 alkynyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different; and the phenyl group may optionally have one or more substituents selected from Group 4-4A-1, provided that when it has two or more substituents, then the substituents may be same or different;
the Group 4-4A-1 consists of halogen and a C1-C6 alkyl group;
in the Group 4-4A-1, the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different.

### Claim 4 (depends on 3)

The compound according to claim 3, wherein R2-4A is hydrogen or a C1-C6 alkyl group wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different;
R3-4A is hydrogen, a C1-C6 alkyl group, a (C1-C6 alkoxy)C1-C6 alkyl group, or a benzyl group wherein the C1-C6 alkyl group and the (C1-C6 alkoxy)C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different; and the benzyl group may optionally have one or more substituents selected from the group consisting of halogen, a C1-C6 alkyl group, and a C1-C6 alkoxy group, provided that when it has two or more substituents, then the substituents may be same or different;
R5-4A is a C1-C6 alkyl group or a phenyl group wherein the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different; and the phenyl group has one or more C1-C6 alkyl groups, provided that when it has two or more C1-C6 alkyl groups, then the C1-C6 alkyl groups may be same or different; and
G4A is a phenyl group, a pyridyl group, an indolyl group or a pyrazolyl group wherein the phenyl group, the pyridyl group, the indolyl group and the pyrazolyl group may optionally have one or more substituents selected from Group R4-4A-1, provided that when they have two or more substituents, then the substituents may be same or different.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein R2-4A is a methyl group, a 4-fluorophenyl group or a trifluoromethyl group, R3-4A is a methyl group or a benzyl group, R5-4A is a methyl group or a 4-methylphenyl group, and G4A is a 2,4,6-triethylphenyl group, a 2-ethyl-5-(4-chlorophenyl)phenyl group, a 5-ethyl-3-(4-trifluoromethylphenyl)pyrazol-1-yl group, a 1-methylindol-3-yl group or a 2,6-diethyl-4-methylphenyl group.

### Claim 6 (depends on 2)

The compound according to claim 2, wherein the Group R4-4A is Group R4-4A-1;
wherein the Group R4-4A-1 consists of halogen, a cyano group, a nitro group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C3-C6 cycloalkyl group, a C2-C6 alkynyl group, and a phenyl group;
in the Group R4-4A-1, the C1-C6 alkyl group, the C1-C6 alkoxy group, the C3-C6 cycloalkyl group, and the C2-C6 alkynyl group may be optionally substituted with one or more halogens, provided that when they are substituted with two or more halogens, then the halogens may be same or different; and the phenyl group may optionally have one or more substituents selected from Group 4-4A-1, provided that when it has two or more substituents, then the substituents may be same or different;
the Group 4-4A-1 consists of halogen and a C1-C6 alkyl group;
in the Group 4-4A-1, the C1-C6 alkyl group may be optionally substituted with one or more halogens, provided that when it is substituted with two or more halogens, then the halogens may be same or different.