JP2016508994A5 - - Google Patents
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- Publication number
- JP2016508994A5 JP2016508994A5 JP2015553925A JP2015553925A JP2016508994A5 JP 2016508994 A5 JP2016508994 A5 JP 2016508994A5 JP 2015553925 A JP2015553925 A JP 2015553925A JP 2015553925 A JP2015553925 A JP 2015553925A JP 2016508994 A5 JP2016508994 A5 JP 2016508994A5
- Authority
- JP
- Japan
- Prior art keywords
- aminomethyl
- methyl
- acid
- hexanoic acid
- phenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 201000010099 disease Diseases 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 208000035475 disorder Diseases 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 24
- KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 208000017520 skin disease Diseases 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 201000008937 atopic dermatitis Diseases 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 208000010668 atopic eczema Diseases 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 14
- -1 3-aminomethyl-5-benzyl-hexanoic acid (S) -3-aminomethyl-5-methylhexanoic acid Chemical compound 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 230000035876 healing Effects 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 11
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
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- 125000003118 aryl group Chemical group 0.000 claims description 8
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 230000003628 erosive effect Effects 0.000 claims description 6
- 230000003176 fibrotic effect Effects 0.000 claims description 6
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
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- 239000002085 irritant Substances 0.000 claims description 6
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- 150000003141 primary amines Chemical class 0.000 claims description 6
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- 125000004429 atom Chemical group 0.000 claims description 5
- FEWJHICLKRAPHS-OCCSQVGLSA-N (3s,5r)-3-(aminomethyl)-5-methyl-7-phenylheptanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CCC1=CC=CC=C1 FEWJHICLKRAPHS-OCCSQVGLSA-N 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 206010034277 Pemphigoid Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 230000001363 autoimmune Effects 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 208000015606 cardiovascular system disease Diseases 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 4
- 230000006589 gland dysfunction Effects 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 210000004561 lacrimal apparatus Anatomy 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- AYXYPKUFHZROOJ-SSDOTTSWSA-N pregabalin Chemical compound CC(C)C[C@@H](CN)CC(O)=O AYXYPKUFHZROOJ-SSDOTTSWSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 231100000241 scar Toxicity 0.000 claims description 4
- 231100000331 toxic Toxicity 0.000 claims description 4
- 230000002588 toxic effect Effects 0.000 claims description 4
- JBBFMHZVKGOWPT-YPMHNXCESA-N (3s,5s)-3-(aminomethyl)-5-methyl-6-phenylhexanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CC1=CC=CC=C1 JBBFMHZVKGOWPT-YPMHNXCESA-N 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 208000024891 symptom Diseases 0.000 claims description 3
- IASDTUBNBCYCJG-SFYZADRCSA-N (3r,4r)-3-(azaniumylmethyl)-4,5-dimethylhexanoate Chemical compound CC(C)[C@@H](C)[C@H](CN)CC(O)=O IASDTUBNBCYCJG-SFYZADRCSA-N 0.000 claims description 2
- IASDTUBNBCYCJG-YUMQZZPRSA-N (3r,4s)-3-(azaniumylmethyl)-4,5-dimethylhexanoate Chemical compound CC(C)[C@H](C)[C@H](CN)CC(O)=O IASDTUBNBCYCJG-YUMQZZPRSA-N 0.000 claims description 2
- IASDTUBNBCYCJG-JGVFFNPUSA-N (3s,4s)-3-(aminomethyl)-4,5-dimethylhexanoic acid Chemical compound CC(C)[C@H](C)[C@@H](CN)CC(O)=O IASDTUBNBCYCJG-JGVFFNPUSA-N 0.000 claims description 2
- BGQCKHBIIZKBJU-ZJUUUORDSA-N (3s,5r)-3-(aminomethyl)-5,7-dimethyloctanoic acid Chemical compound CC(C)C[C@@H](C)C[C@H](CN)CC(O)=O BGQCKHBIIZKBJU-ZJUUUORDSA-N 0.000 claims description 2
- XKLLXPMHSPFOQW-HIFRSBDPSA-N (3s,5r)-3-(aminomethyl)-5-methyl-8-phenyloctanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CCCC1=CC=CC=C1 XKLLXPMHSPFOQW-HIFRSBDPSA-N 0.000 claims description 2
- IMLWGNYZSUWXIA-OLZOCXBDSA-N (3s,5r)-3-(aminomethyl)-5-methyldodecanoic acid Chemical compound CCCCCCC[C@@H](C)C[C@H](CN)CC(O)=O IMLWGNYZSUWXIA-OLZOCXBDSA-N 0.000 claims description 2
- LFUPHGVCYOENSK-ZJUUUORDSA-N (3s,5r)-3-(aminomethyl)-5-methylnon-8-enoic acid Chemical compound C=CCC[C@@H](C)C[C@H](CN)CC(O)=O LFUPHGVCYOENSK-ZJUUUORDSA-N 0.000 claims description 2
- KUSIIZRBOLFILF-ZJUUUORDSA-N (3s,5r)-3-(aminomethyl)-5-methylnonanoic acid Chemical compound CCCC[C@@H](C)C[C@H](CN)CC(O)=O KUSIIZRBOLFILF-ZJUUUORDSA-N 0.000 claims description 2
- YAMOPJPIJYQIGY-BDAKNGLRSA-N (3s,5r)-3-(aminomethyl)-5-methyloct-7-enoic acid Chemical compound C=CC[C@@H](C)C[C@H](CN)CC(O)=O YAMOPJPIJYQIGY-BDAKNGLRSA-N 0.000 claims description 2
- KKXFMWXZXDUYBF-BDAKNGLRSA-N (3s,5r)-3-(aminomethyl)-5-methyloctanoic acid Chemical compound CCC[C@@H](C)C[C@H](CN)CC(O)=O KKXFMWXZXDUYBF-BDAKNGLRSA-N 0.000 claims description 2
- HLRPRVFNTZZSHY-NEPJUHHUSA-N (3s,5r)-3-(aminomethyl)-5-methylundecanoic acid Chemical compound CCCCCC[C@@H](C)C[C@H](CN)CC(O)=O HLRPRVFNTZZSHY-NEPJUHHUSA-N 0.000 claims description 2
- SHMPJXGCBKABBT-KOLCDFICSA-N (3s,5r)-3-(aminomethyl)-6-cyclobutyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CC1CCC1 SHMPJXGCBKABBT-KOLCDFICSA-N 0.000 claims description 2
- LUHAQNAPMJQCNM-YPMHNXCESA-N (3s,5r)-3-(aminomethyl)-6-cyclohexyl-5-methylhexanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CC1CCCCC1 LUHAQNAPMJQCNM-YPMHNXCESA-N 0.000 claims description 2
- SMNXTMSRSMKVKF-NEPJUHHUSA-N (3s,5r)-3-(aminomethyl)-7-(2-chlorophenyl)-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CCC1=CC=CC=C1Cl SMNXTMSRSMKVKF-NEPJUHHUSA-N 0.000 claims description 2
- UHGGXBVJHJAACY-NEPJUHHUSA-N (3s,5r)-3-(aminomethyl)-7-(2-fluorophenyl)-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CCC1=CC=CC=C1F UHGGXBVJHJAACY-NEPJUHHUSA-N 0.000 claims description 2
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- CBBMTFZOSNWURO-YPMHNXCESA-N (3s,5r)-3-(aminomethyl)-7-(4-fluorophenyl)-5-methylheptanoic acid Chemical compound OC(=O)C[C@@H](CN)C[C@H](C)CCC1=CC=C(F)C=C1 CBBMTFZOSNWURO-YPMHNXCESA-N 0.000 claims description 2
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- 2020-02-25 JP JP2020029608A patent/JP2020079305A/ja not_active Withdrawn
-
2021
- 2021-04-12 US US17/227,568 patent/US11701331B2/en active Active
-
2022
- 2022-03-07 US US17/653,827 patent/US11771664B2/en active Active
- 2022-09-22 JP JP2022151228A patent/JP7457401B2/ja active Active
-
2023
- 2023-08-22 US US18/236,795 patent/US12128013B2/en active Active
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2024
- 2024-03-08 JP JP2024036019A patent/JP2024057103A/ja active Pending
- 2024-10-02 US US18/904,373 patent/US20250127733A1/en active Pending
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