JP2021119131A5 - - Google Patents
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- JP2021119131A5 JP2021119131A5 JP2021012154A JP2021012154A JP2021119131A5 JP 2021119131 A5 JP2021119131 A5 JP 2021119131A5 JP 2021012154 A JP2021012154 A JP 2021012154A JP 2021012154 A JP2021012154 A JP 2021012154A JP 2021119131 A5 JP2021119131 A5 JP 2021119131A5
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- phenyl
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- benzenesulfonamide
- pharmaceutical composition
- propanoic acid
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 42
- 208000033808 peripheral neuropathy Diseases 0.000 claims 30
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 26
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 21
- 235000019260 propionic acid Nutrition 0.000 claims 21
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 16
- 201000001119 neuropathy Diseases 0.000 claims 14
- 230000007823 neuropathy Effects 0.000 claims 14
- 125000002947 alkylene group Chemical group 0.000 claims 12
- 239000003795 chemical substances by application Substances 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 230000004112 neuroprotection Effects 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 5
- 210000004116 schwann cell Anatomy 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 4
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 239000002246 antineoplastic agent Substances 0.000 claims 4
- 208000015114 central nervous system disease Diseases 0.000 claims 4
- 229940127089 cytotoxic agent Drugs 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 101100273648 Mus musculus Ccna2 gene Proteins 0.000 claims 3
- 101100059444 Mus musculus Ccnb1 gene Proteins 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 230000024245 cell differentiation Effects 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 210000004498 neuroglial cell Anatomy 0.000 claims 3
- 230000000324 neuroprotective effect Effects 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 230000001737 promoting effect Effects 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 206010003497 Asphyxia Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000032514 Leukocytoclastic vasculitis Diseases 0.000 claims 2
- 208000010641 Tooth disease Diseases 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 239000003242 anti bacterial agent Substances 0.000 claims 2
- 229940125681 anticonvulsant agent Drugs 0.000 claims 2
- 239000001961 anticonvulsive agent Substances 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 2
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 230000037406 food intake Effects 0.000 claims 2
- 229910001385 heavy metal Inorganic materials 0.000 claims 2
- 230000023105 myelination Effects 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 231100000614 poison Toxicity 0.000 claims 2
- 230000003449 preventive effect Effects 0.000 claims 2
- 229940125723 sedative agent Drugs 0.000 claims 2
- 239000000932 sedative agent Substances 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 239000003440 toxic substance Substances 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 1
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 1
- WJIJCKFLRPPSLM-IZZNHLLZSA-N 3-[2-[(3S)-3-hydroxy-5-[3-[(1R)-1-hydroxy-2-phenylethyl]phenyl]pentoxy]phenyl]propanoic acid Chemical compound O[C@H](CCOC1=C(C=CC=C1)CCC(=O)O)CCC1=CC(=CC=C1)[C@@H](CC1=CC=CC=C1)O WJIJCKFLRPPSLM-IZZNHLLZSA-N 0.000 claims 1
- WJIJCKFLRPPSLM-UIOOFZCWSA-N 3-[2-[(3S)-3-hydroxy-5-[3-[(1S)-1-hydroxy-2-phenylethyl]phenyl]pentoxy]phenyl]propanoic acid Chemical compound O[C@H](CCOC1=C(C=CC=C1)CCC(=O)O)CCC1=CC(=CC=C1)[C@H](CC1=CC=CC=C1)O WJIJCKFLRPPSLM-UIOOFZCWSA-N 0.000 claims 1
- LAZNIUILWXDFHF-VKXNWWILSA-N 3-[2-[(E,3R)-5-[3-(cyclopentylsulfonylamino)phenyl]-3-hydroxypent-4-enoxy]phenyl]propanoic acid Chemical compound C1(CCCC1)S(=O)(=O)NC=1C=C(C=CC=1)/C=C/[C@@H](CCOC1=C(C=CC=C1)CCC(=O)O)O LAZNIUILWXDFHF-VKXNWWILSA-N 0.000 claims 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
- 101100112680 Ostreococcus tauri CycD gene Proteins 0.000 claims 1
- 208000035217 Ring chromosome 1 syndrome Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 claims 1
- 230000002518 glial effect Effects 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 125000000232 haloalkynyl group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000001620 monocyclic carbocycle group Chemical group 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
Claims (36)
R11、R13、R16、R17、R18、およびR20は、それぞれ独立して、(1)1~3個のハロゲン原子で置換されていてもよいC1~6アルキレン基、(2)1~3個のハロゲン原子で置換されていてもよいC2~6アルケニレン基、または(3)1~3個のハロゲン原子で置換されていてもよいC2~6アルキニレン基を表し、基中、アルキレン基、アルケニレン基またはアルキニレン基が分枝鎖の場合、同一の炭素原子から分枝した2個のC1~2アルキル基は一緒になってC3~5の飽和炭素環を形成してもよく、
R12、R14、R15およびR19は、それぞれ独立して、(1)水素原子、(2)C1~4アルキル基、または(3)C1~4ハロアルキル基を表し、
CycDは、トリアゾールまたはテトラゾールを表し、
R2は、(1)ハロゲン原子、(2)C1~4アルキル基、または(3)C1~4ハロアルキル基を表し、pは0から3の整数を表し、pが2以上のとき複数のR2はそれぞれ同じでも異なっていてもよく、
Xは、(1)CH2、または(2)酸素原子を表し、
L1は、(1)1~4個のRL1aで置換されていてもよい直鎖のC3~7アルキレン基、(2)1~4個のRL1aで置換されていてもよい直鎖のC3~7アルケニレン基、(3)1~4個のRL1aで置換されていてもよい直鎖のC3~7アルキニレン基、または(4)(1~2個のRL1aで置換されていてもよい直鎖のC1~3アルキレン基)-O-(1~2個のRL1aで置換されていてもよい直鎖のC1~3アルキレン基)を表し、
RL1aは、(1)ハロゲン原子、(2)水酸基、(3)オキソ基、または(4)C1~2アルキル基を表し、RL1aが2個以上のとき複数のRL1aは同じでも異なっていてもよく、さらに同一の炭素原子に結合する2個のRL1aがそれぞれC1~2アルキル基のとき、該C1~2アルキル基は結合する炭素原子と一緒になってC3~5の飽和炭素環を形成してもよく、
R3は、(1)水素原子、(2)ハロゲン原子、(3)水酸基、(4)C1~2アルキル基、または(5)メチリデン基を表し、qは0から2の整数を表し、
CycAは、(1)C5~10単環式もしくは二環式炭素環、または(2)5~10員の単環式もしくは二環式複素環を表し、
R4は、(1)ハロゲン原子、(2)水酸基、(3)C1~4アルキル基、(4)C1~4ハロアルキル基、(5)C1~4アルコキシ基、(6)C1~4ハロアルコキシ基、(7)シアノ基、または(8)-SO2-C1~2アルキル基を表し、rは0から6の整数を表し、rが2以上のとき複数のR4はそれぞれ同じでも異なっていてもよく、
L2は、-R31-L3-R32-を表し、
L3は、(1)-NR201-S(O)-、(2)-NR202-S(O)2-、(3)-NR203-C(O)-、(4)-CR204(OH)-、(5)-NR205-、(6)-S(O)-、または(7)-S(O)2-を表し、
R201、R202、R203、R204、およびR205は、それぞれ独立して、(1)水素原子、(2)C1~4アルキル基、または(3)C1~4ハロアルキル基を表し、基中、アルキル基またはハロアルキル基は、(1)水酸基、(2)オキソ基、(3)C3~6単環式炭素環、または(4)3~6員の単環式複素環で置換されていてもよく、
R31およびR32は、それぞれ独立して、(1)結合手、または(2)ハロゲン原子、水酸基およびオキソ基からなる群から選択される1~3個の置換基で置換されていてもよいC1~3アルキレン基を表し、
CycBは、(1)C5~10単環式もしくは二環式炭素環、または(2)5~10員の単環式もしくは二環式複素環を表し、
R5は、(1)ハロゲン原子、(2)C1~6アルキル基、(3)C2~6アルケニル基、(4)C2~6アルキニル基、(5)C1~6ハロアルキル基、(6)C2~6ハロアルケニル基、(7)C2~6ハロアルキニル基、(8)C1~6アルコキシ基、または(9)C1~6ハロアルコキシ基を表し、tは0から6の整数を表し、tが2以上のとき複数のR5はそれぞれ同じでも異なっていてもよい。]で示される化合物またはその塩を含有する医薬組成物。 General formula (I)
R 11 , R 13 , R 16 , R 17 , R 18 and R 20 are each independently (1) a C1 to 6 alkylene group which may be substituted with 1 to 3 halogen atoms, (2). ) Represents a C2-6 alkenylene group optionally substituted with 1 to 3 halogen atoms, or (3) a C2-6 alkynylene group optionally substituted with 1 to 3 halogen atoms. When the alkylene group, alkenylene group or alkynylene group is a branched chain, two C1-2 alkyl groups branched from the same carbon atom may be combined to form a saturated carbon ring of C3-5.
R 12 , R 14 , R 15 and R 19 independently represent (1) a hydrogen atom, (2) a C1-4 alkyl group, or (3) a C1-4 haloalkyl group, respectively.
CycD stands for triazole or tetrazole,
R 2 represents (1) a halogen atom, (2) a C1-4 alkyl group, or (3) a C1-4 haloalkyl group, p represents an integer from 0 to 3, and when p is 2 or more, a plurality of Rs. 2 may be the same or different,
X represents (1) CH 2 or (2) oxygen atom.
L 1 is (1) a linear C3 to 7 alkylene group which may be substituted with 1 to 4 RL1a , and (2) a linear chain which may be substituted with 1 to 4 RL1a . C3 to 7 alkenylene groups, (3) may be substituted with 1 to 4 RL1a , linear C3 to 7 alkynylene groups, or (4) may be substituted with 1 to 2 RL1a . A good linear C1-3 alkylene group) -O- (a linear C1-3 alkylene group that may be substituted with 1-2 RL1a ).
RL1a represents (1) a halogen atom, (2) a hydroxyl group, (3) an oxo group, or (4) a C1-2 alkyl group, and when there are two or more RL1a , a plurality of RL1a are the same but different. Further, when two RL1a bonded to the same carbon atom are C1-2 alkyl groups, respectively, the C1-2 alkyl groups are combined with the carbon atom to be bonded to form a saturated carbon ring of C3 to 5. May form,
R 3 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 from 0 to 2.
CycA represents (1) C5-10 monocyclic or bicyclic carbocycles, or (2) 5-10 membered monocyclic or bicyclic heterocycles.
R4 is (1) halogen atom, (2) hydroxyl group, (3) C1-4 alkyl group, (4) C1-4 haloalkyl group, (5) C1-4 alkoxy group, (6) C1-4 haloalkoxy group. Represents a group, (7) cyano group, or (8) -SO2 -C1-2 alkyl group, r represents an integer from 0 to 6, and when r is 2 or more, multiple R4s are the same but different. May,
L 2 represents -R 31 -L 3 -R 32- , and represents.
L 3 is (1) -NR 201 -S (O)-, (2) -NR 202 -S (O) 2- , (3) -NR 203 -C (O)-, (4) -CR 204 Represents (OH)-, (5) -NR 205- , (6) -S (O)-, or (7) -S (O) 2- .
R 201 , R 202 , R 203 , R 204 , and R 205 independently represent (1) a hydrogen atom, (2) a C1-4 alkyl group, or (3) a C1-4 haloalkyl group, respectively. Among them, the alkyl group or haloalkyl group is substituted with (1) a hydroxyl group, (2) an oxo group, (3) a C3 to 6 monocyclic carbocycle, or (4) a 3 to 6 member monocyclic heterocycle. May,
R 31 and R 32 may each be independently substituted with (1) a bond or (2) 1 to 3 substituents selected from the group consisting of halogen atoms, hydroxyl groups and oxo groups. Represents a C1-3 alkylene group
CycB represents (1) C5-10 monocyclic or bicyclic carbocycles, or (2) 5-10 membered monocyclic or bicyclic heterocycles.
R5 is ( 1 ) a halogen atom, (2) a C1 to 6 alkyl group, (3) a C2 to 6 alkenyl group, (4) a C2 to 6 alkynyl group, (5) a C1 to 6 haloalkyl group, and (6) C2. Represents a ~ 6 haloalkenyl group, (7) C2-6 haloalkynyl group, (8) C1-6 alkoxy group, or (9) C1-6 haloalkoxy group, where t represents an integer from 0 to 6 and t is. When the number is 2 or more, the plurality of R5s may be the same or different. ] A pharmaceutical composition containing the compound represented by the above or a salt thereof.
(1)3-[2-[(E,3R)-5-[3-(ベンゼンスルホンアミド)フェニル]-3-ヒドロキシペンタ-4-エノキシ]フェニル]プロパン酸、
(2)3-[2-[(3S)-5-[3-(ベンゼンスルホンアミド)フェニル]-3-ヒドロキシペントキシ]フェニル]プロパン酸、
(3)3-[2-[(3R)-5-[3-(ベンゼンスルホンアミド)フェニル]-3-ヒドロキシペントキシ]フェニル]プロパン酸、
(4)3-[2-[(E,3R)-5-[4-(ベンゼンスルホンアミド)フェニル]-3-ヒドロキシペンタ-4-エノキシ]フェニル]プロパン酸、
(5)3-[2-[(E,3R)-5-[3-(シクロペンチルスルホニルアミノ)フェニル]-3-ヒドロキシペンタ-4-エノキシ]フェニル]プロパン酸、
(6)3-[2-[(E,3R)-5-[3-(ベンゼンスルホンアミド)-2-メチルフェニル]-3-ヒドロキシペンタ-4-エノキシ]フェニル]プロパン酸、
(7)4-[2-[(E,3R)-5-[3-(ベンゼンスルホンアミド)フェニル]-3-ヒドロキシペンタ-4-エノキシ]フェニル]ブタン酸、
(8)3-[2-[(E)-4-[3-(ベンゼンスルホンアミド)フェニル]-2-ヒドロキシブタ-3-エノキシ]フェニル]プロパン酸、
(9)(R)-3-[2-[(E)-6-[3-(ベンゼンスルホンアミド)フェニル]-4-ヒドロキシヘキサ-5-エニル]フェニル]プロパン酸、
(10)(S)-3-[2-[(E)-6-[3-(ベンゼンスルホンアミド)フェニル]-4-ヒドロキシヘキサ-5-エニル]フェニル]プロパン酸、
(11)3-[2-[(E)-5-[3-(ベンゼンスルホンアミド)フェニル]ペンタ-4-エノキシ]フェニル]プロパン酸、
(12)3-[2-[5-[3-(ベンゼンスルホンアミド)フェニル]ペントキシ]フェニル]プロパン酸、
(13)3-[2-[(3S)-3-ヒドロキシ-5-[3-[(1R)-1-ヒドロキシ-2-フェニルエチル]フェニル]ペントキシ]フェニル]プロパン酸、
(14)3-[2-[(3S)-3-ヒドロキシ-5-[3-[(1S)-1-ヒドロキシ-2-フェニルエチル]フェニル]ペントキシ]フェニル]プロパン酸、
(15)3-[2-[2-[2-[3-(ベンゼンスルホンアミド)フェニル]エトキシ]エトキシ]フェニル]プロパン酸、
(16)3-[2-[6-[3-(ベンゼンスルホンアミド)フェニル]-4-オキソヘキシル]フェニル]プロパン酸、もしくは
(17)3-[2-[5-[3-(ベンゼンスルホンアミド)フェニル]-3,3-ジフルオロペントキシ]フェニル]プロパン酸またはその塩である、請求項1に記載の医薬組成物。 The compound represented by the general formula (I) or a salt thereof is
(1) 3- [2-[(E, 3R) -5- [3- (benzenesulfonamide) phenyl] -3-hydroxypenta-4-enoxy] phenyl] propanoic acid,
(2) 3- [2-[(3S) -5- [3- (benzenesulfonamide) phenyl] -3-hydroxypentoxy] phenyl] propanoic acid,
(3) 3- [2-[(3R) -5- [3- (benzenesulfonamide) phenyl] -3-hydroxypentoxy] phenyl] propanoic acid,
(4) 3- [2-[(E, 3R) -5- [4- (benzenesulfonamide) phenyl] -3-hydroxypenta-4-enoxy] phenyl] propanoic acid,
(5) 3- [2-[(E, 3R) -5- [3- (cyclopentylsulfonylamino) phenyl] -3-hydroxypenta-4-enoxy] phenyl] propanoic acid,
(6) 3- [2-[(E, 3R) -5- [3- (benzenesulfonamide) -2-methylphenyl] -3-hydroxypenta-4-enoxy] phenyl] propanoic acid,
(7) 4- [2-[(E, 3R) -5- [3- (benzenesulfonamide) phenyl] -3-hydroxypenta-4-enoxy] phenyl] butanoic acid,
(8) 3- [2-[(E) -4- [3- (benzenesulfonamide) phenyl] -2-hydroxybut-3-enoxy] phenyl] propanoic acid,
(9) (R) -3- [2-[(E) -6- [3- (benzenesulfonamide) phenyl] -4-hydroxyhex-5-enyl] phenyl] propionic acid,
(10) (S) -3- [2-[(E) -6- [3- (benzenesulfonamide) phenyl] -4-hydroxyhex-5-enyl] phenyl] propionic acid,
(11) 3- [2-[(E) -5- [3- (benzenesulfonamide) phenyl] penta-4-enoxy] phenyl] propionic acid,
(12) 3- [2- [5- [3- (benzenesulfonamide) phenyl] pentoxy] phenyl] propanoic acid,
(13) 3- [2-[(3S) -3-hydroxy-5- [3-[(1R) -1-hydroxy-2-phenylethyl] phenyl] pentoxy] phenyl] propanoic acid,
(14) 3- [2-[(3S) -3-hydroxy-5- [3-[(1S) -1-hydroxy-2-phenylethyl] phenyl] pentoxy] phenyl] propanoic acid,
(15) 3- [2- [2- [2- [3- (benzenesulfonamide) phenyl] ethoxy] ethoxy] phenyl] propanoic acid,
(16) 3- [2- [6- [3- (benzenesulfonamide) phenyl] -4-oxohexyl] phenyl] propanoic acid, or (17) 3- [2- [5- [3- (benzenesulfone) The pharmaceutical composition according to claim 1, which is amide) phenyl] -3,3-difluoropentoxy] phenyl] propanoic acid or a salt thereof.
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JP2020012078 | 2020-01-29 | ||
JP2020012078 | 2020-01-29 |
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JP2021119131A JP2021119131A (en) | 2021-08-12 |
JP2021119131A5 true JP2021119131A5 (en) | 2022-06-02 |
JP7384179B2 JP7384179B2 (en) | 2023-11-21 |
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