NZ772452B2 - Benzene derivative - Google Patents

Benzene derivative Download PDF

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Publication number
NZ772452B2
NZ772452B2 NZ772452A NZ77245219A NZ772452B2 NZ 772452 B2 NZ772452 B2 NZ 772452B2 NZ 772452 A NZ772452 A NZ 772452A NZ 77245219 A NZ77245219 A NZ 77245219A NZ 772452 B2 NZ772452 B2 NZ 772452B2
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NZ
New Zealand
Prior art keywords
phenyl
group
propanoic acid
benzenesulfonamido
salt
Prior art date
Application number
NZ772452A
Other versions
NZ772452A (en
Inventor
Yoshikazu Goto
Tohru Kambe
Takashi Konemura
Shoji Nojima
Kenji Sasaki
Original Assignee
Ono Pharmaceutical Co Ltd
Filing date
Publication date
Application filed by Ono Pharmaceutical Co Ltd filed Critical Ono Pharmaceutical Co Ltd
Priority claimed from PCT/JP2019/029883 external-priority patent/WO2020027150A1/en
Publication of NZ772452A publication Critical patent/NZ772452A/en
Publication of NZ772452B2 publication Critical patent/NZ772452B2/en

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    • A61K31/18—Sulfonamides
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    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
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    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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Abstract

compound represented by general formula (I-1) (in the formula, all symbols are as described in the description) or a salt thereof has a potent nerve-protecting and/or -repairing activity, and therefore can be used as a therapeutic agent for neuropathy (e.g., chronic inflammatory demyelinating polyneuropathy, Guillain-Barre syndrome, periarteritis nodosa, allergic vasculitis, diabetic peripheral neuropathy, entrapment neuropathy, peripheral neuropathy associated with the administration of a chemotherapeutic drug, or peripheral neuropathy associated with Charcot-Marie-Tooth disease).

Claims (17)

1. A compound represented by general formula (I-1) 11-1 1-1 5 wherein: R represents a C2-4 alkylene group; L represents a linear C3-4 alkylene group L1a 1 1 which may be substituted by 1 to 2 R s; CycA and CycB each independently represent a C5-6 monocyclic carbocyclic ring; L represents (1) -NH-S(O) - or (2) -CH(OH)-CH -; and wherein: R represents (1) a hydrogen atom, (2) a C1-4 alkyl group or (3) a C1-4 haloalkyl 10 group; R represents (1) a halogen atom, (2) a C1-4 alkyl group or (3) a C1-4 haloalkyl group, and p represents an integer of 0 to 3, wherein, when p is 2 or more, a plurality of R s may be the same as or different from each other; X represents (1) CH or (2) an oxygen atom; 15 R represents (1) a halogen atom, (2) a hydroxyl group, (3) an oxo group or (4) a L1a L1a C1-2 alkyl group, wherein: when there are at least two R s, a plurality of R s may be the same as or different from each other; and when each of two R s bonded to a single carbon atom is a C1-2 alkyl group, the C1-2 alkyl group may form a C3-5 saturated carbocyclic ring in conjunction with the carbon atom to which the C1-2 alkyl group is bonded; represents a single bond, a double bond or a triple bond; R represents (1) a hydrogen atom, (2) a halogen atom, (3) a hydroxyl group, (4) a C1-2 alkyl group, or (5) a methylidene group, and q represents an integer of 0 to 2, wherein: is a single bond and q is 2, a plurality of R s may be the same as or different from each other; and when at least one of R s is a methyl group, the methyl group may form cyclopropane in conjunction with a carbon atom in the adjacent L ; 5 R represents (1) a halogen atom, (2) a hydroxyl group, (3) a C1-4 alkyl group, (4) a C1-4 haloalkyl group, (5) a C1-4 alkoxy group, (6) a C1-4 haloalkoxy group, (7) a cyano group, or (8) a -SO -C1-2 alkyl group, and r represents an integer of 0 to 6, wherein, when r is 2 or more, a plurality of R s may be the same as or different from each other; R represents (1) a halogen atom, (2) a C1-6 alkyl group, (3) a C2-6 alkenyl group, 10 (4) a C2-6 alkynyl group, (5) a C1-6 haloalkyl group, (6) a C2-6 haloalkenyl group, (7) a C2- 6 haloalkynyl group, (8) a C1-6 alkoxy group, or (9) a C1-6 haloalkoxy group, and t represents an integer of 0 to 6, wherein, when t is 2 or more, a plurality of R s may be the same as or different from each other], or a salt thereof.
2. The compound or the salt thereof according to claim 1, wherein X is an oxygen atom. 15
3. The compound or the salt thereof according to claim 1, wherein the compound or the salt thereof is (1) 3-[2-[(E,3R)[3-(benzenesulfonamido)phenyl]hydroxypent enoxy]phenyl]propanoic acid, (2) 3-[2-[(3S)[3-(benzenesulfonamido)phenyl] 20 hydroxypentoxy]phenyl]propanoic acid, (3) 3-[2-[(3R)[3-(benzenesulfonamido)phenyl] hydroxypentoxy]phenyl]propanoic acid, (4) 3-[2-[(E,3R)[4-(benzenesulfonamido)phenyl]hydroxypent enoxy]phenyl]propanoic acid, 25 (5) 3-[2-[(E,3R)[3-(cyclopentylsulfonylamino)phenyl]hydroxypent enoxy]phenyl]propanoic acid, (6) 3-[2-[(E,3R)[3-(benzenesulfonamido)methylphenyl]hydroxypent enoxy]phenyl]propanoic acid, (7) 4-[2-[(E,3R)[3-(benzenesulfonamido)phenyl]hydroxypent 30 enoxy]phenyl]butanoic acid, (8) 3-[2-[(E)[3-(benzenesulfonamido)phenyl]hydroxybut enoxy]phenyl]propanoic acid, (9) (R)[2-[(E)[3-(benzenesulfonamido)phenyl]hydroxyhex enyl]phenyl]propanoic acid, (10) (S)[2-[(E)[3-(benzenesulfonamido)phenyl]hydroxyhex enyl]phenyl]propanoic acid, 5 (11) 3-[2-[(E)[3-(benzenesulfonamido)phenyl]pentenoxy]phenyl]propanoic acid, (12) 3-[2-[5-[3-(benzenesulfonamido)phenyl]pentoxy]phenyl]propanoic acid, (13) 3-[2-[(3S)hydroxy[3-[(1R)hydroxy phenylethyl]phenyl]pentoxy]phenyl]propanoic acid, 10 (14) 3-[2-[(3S)hydroxy[3-[(1S)hydroxy phenylethyl]phenyl]pentoxy]phenyl]propanoic acid, (15) 3-[2-[2-[2-[3-(benzenesulfonamido)phenyl]ethoxy]ethoxy]phenyl]propanoic acid, (16) 3-[2-[6-[3-(benzenesulfonamido)phenyl]oxohexyl]phenyl]propanoic acid, or 15 (17) 3-[2-[5-[3-(benzenesulfonamido)phenyl]-3,3-difluoropentoxy]phenyl]propanoic acid, or a salt thereof.
4. The compound or salt thereof according to claim 1, which is 3-[2-[(E)[3- (benzenesulfonamido)phenyl]pent 20 enoxy]phenyl]propanoic acid or a salt thereof.
5. The compound according to claim 1 represented by the formula:
6. The salt of a compound according to claim 1 represented by the formula:
7. A pharmaceutical composition comprising the compound represented by general formula (I-1) or the salt thereof according to any one of claims 1 to 6.
8. An agent for Schwann cell differentiation promotion comprising the compound 5 represented by general formula (I-1) or the salt thereof according to any one of claims 1 to 6.
9. A prophylactic and/or therapeutic agent for neuropathy, comprising the compound represented by general formula (I-1) or the salt thereof according to any one of claims 1 to 6.
10. Use of the compound represented by general formula (I-1) or the salt thereof according to any one of claims 1 to 6 in the manufacture of a medicament for preventing 10 and/or treating neuropathy.
11. The use according to claim 10, wherein the neuropathy is peripheral neuropathy.
12. The use according to claim 11, wherein the peripheral neuropathy is chronic inflammatory demyelinating polyneuropathy, Guillain-Barre syndrome, periarteritis nodosa, allergic vasculitis, diabetic peripheral neuropathy, entrapment neuropathy, peripheral 15 neuropathy associated with Charcot-Marie-Tooth disease, peripheral neuropathy associated with an infectious disease, a drug-induced peripheral neuropathy associated with the administration of phenytoin, an anti-microbial agent, a chemotherapeutic drug or a sedative agent, multifocal motor neuropathy or a toxic peripheral neuropathy associated with the ingestion of a heavy metal, an organic solvent, a toxic substance or an alcohol. 20
13. The use according to claim 12, wherein the drug-induced peripheral neuropathy is peripheral neuropathy associated with the administration of a chemotherapeutic drug.
14. The use according to claim 10, wherein the neuropathy is central neuropathy.
15. The use according to claim 14, wherein the central neuropathy is amyotrophic lateral sclerosis.
16. Use of the compound represented by general formula (I-1) or the salt thereof according to any one of claims 1 to 6 in the manufacture of a medicament for Schwann cell differentiation promotion.
17. The compound or the salt thereof according to claim 1, substantially as herein 5 described with reference to any one of the Examples and/or
NZ772452A 2019-07-30 Benzene derivative NZ772452B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018143024 2018-07-31
PCT/JP2019/029883 WO2020027150A1 (en) 2018-07-31 2019-07-30 Benzene derivative

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NZ772452B2 true NZ772452B2 (en) 2024-10-08

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