JP2020507606A5 - - Google Patents
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- JP2020507606A5 JP2020507606A5 JP2019543998A JP2019543998A JP2020507606A5 JP 2020507606 A5 JP2020507606 A5 JP 2020507606A5 JP 2019543998 A JP2019543998 A JP 2019543998A JP 2019543998 A JP2019543998 A JP 2019543998A JP 2020507606 A5 JP2020507606 A5 JP 2020507606A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- ethyl
- methyl
- alkyl
- fluoro
- 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 91
- 125000000217 alkyl group Chemical group 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 77
- -1 N, N-dimethylaminoethyl Chemical group 0.000 claims description 59
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 102000001708 Protein Isoforms Human genes 0.000 claims description 14
- 108010029485 Protein Isoforms Proteins 0.000 claims description 14
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000009286 beneficial effect Effects 0.000 claims description 7
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 108090000312 Calcium Channels Proteins 0.000 claims description 6
- 102000003922 Calcium Channels Human genes 0.000 claims description 6
- 102000003691 T-Type Calcium Channels Human genes 0.000 claims description 6
- 108090000030 T-Type Calcium Channels Proteins 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 235000001484 Trigonella foenum graecum Nutrition 0.000 claims description 3
- 244000250129 Trigonella foenum graecum Species 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- IWJOAMCMDKUPSS-NMMIHGMASA-N 3-[(1S,2S)-2-[2-[3-[4,6-bis(trifluoromethyl)-1H-benzimidazol-2-yl]propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl]morpholine-4-carboxylic acid Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=C(C=C(C=C4N3)C(F)(F)F)C(F)(F)F)C5COCCN5C(=O)O)C=C(C=C2)F IWJOAMCMDKUPSS-NMMIHGMASA-N 0.000 claims description 2
- IWJOAMCMDKUPSS-UHFFFAOYSA-N 3-[2-[2-[3-[4,6-bis(trifluoromethyl)-1H-benzimidazol-2-yl]propyl-methylamino]ethyl]-6-fluoro-1-propan-2-yl-3,4-dihydro-1H-naphthalen-2-yl]morpholine-4-carboxylic acid Chemical compound CC(C)C1C2=C(CCC1(CCN(C)CCCC3=NC4=C(C=C(C=C4N3)C(F)(F)F)C(F)(F)F)C5COCCN5C(=O)O)C=C(C=C2)F IWJOAMCMDKUPSS-UHFFFAOYSA-N 0.000 claims description 2
- HLKUAFQXZIWWAX-UHFFFAOYSA-N CC(C)C(C(CCN(C)CCC(C)(C)C1=NC(C=CC=C2)=C2N1)(CCC1=C2)C(COCC3)N3C(O)=O)C1=CC=C2F Chemical compound CC(C)C(C(CCN(C)CCC(C)(C)C1=NC(C=CC=C2)=C2N1)(CCC1=C2)C(COCC3)N3C(O)=O)C1=CC=C2F HLKUAFQXZIWWAX-UHFFFAOYSA-N 0.000 claims description 2
- VFGMKSLSMTYVIH-UHFFFAOYSA-N CC(C)C(C(CCN(C)CCC(C)(C)C1=NC(C=CC=C2)=C2N1)(CNC(O)=O)CCC1=C2)C1=CC=C2F Chemical compound CC(C)C(C(CCN(C)CCC(C)(C)C1=NC(C=CC=C2)=C2N1)(CNC(O)=O)CCC1=C2)C1=CC=C2F VFGMKSLSMTYVIH-UHFFFAOYSA-N 0.000 claims description 2
- YVSVPYDBLWZNOA-UHFFFAOYSA-N CC(C)C(C(CCN(C)CCC1(CC1)C1=NC(C=CC=C2)=C2N1)(CCC1=C2)C(COCC3)N3C(O)=O)C1=CC=C2F Chemical compound CC(C)C(C(CCN(C)CCC1(CC1)C1=NC(C=CC=C2)=C2N1)(CCC1=C2)C(COCC3)N3C(O)=O)C1=CC=C2F YVSVPYDBLWZNOA-UHFFFAOYSA-N 0.000 claims description 2
- HHNVXQFSIYTYLZ-UHFFFAOYSA-N CC(C)C(C(CCN(C)CCCC1=NC(C(C)=CC=C2C)=C2N1)(CCC1=C2)C(COCC3)N3C(O)=O)C1=CC=C2F Chemical compound CC(C)C(C(CCN(C)CCCC1=NC(C(C)=CC=C2C)=C2N1)(CCC1=C2)C(COCC3)N3C(O)=O)C1=CC=C2F HHNVXQFSIYTYLZ-UHFFFAOYSA-N 0.000 claims description 2
- GFAVBVNVVBMGRL-UHFFFAOYSA-N CC(C)C(C(CCN(C)CCCC1=NC(C(OC)=CC=C2OC)=C2N1)(CNC(O)=O)CCC1=C2)C1=CC=C2F Chemical compound CC(C)C(C(CCN(C)CCCC1=NC(C(OC)=CC=C2OC)=C2N1)(CNC(O)=O)CCC1=C2)C1=CC=C2F GFAVBVNVVBMGRL-UHFFFAOYSA-N 0.000 claims description 2
- ARFGYDRJRJNMQI-UHFFFAOYSA-N CC(C)C1C2=C(C=C(C=C2)F)OCC1(CCN(C)CCCC3=NC4=CC=CC=C4N3)CNC(=O)O Chemical compound CC(C)C1C2=C(C=C(C=C2)F)OCC1(CCN(C)CCCC3=NC4=CC=CC=C4N3)CNC(=O)O ARFGYDRJRJNMQI-UHFFFAOYSA-N 0.000 claims description 2
- DXZSWYQYGILTFX-UHFFFAOYSA-N CC(C)C1C2=C(CCC1(CCN(C)CCCC3=NC4=C(C=CC(=C4N3)OC)Cl)CN(C)C(=O)O)C=C(C=C2)F Chemical compound CC(C)C1C2=C(CCC1(CCN(C)CCCC3=NC4=C(C=CC(=C4N3)OC)Cl)CN(C)C(=O)O)C=C(C=C2)F DXZSWYQYGILTFX-UHFFFAOYSA-N 0.000 claims description 2
- HLKUAFQXZIWWAX-LMALLOCISA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)C5COCCN5C(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)C5COCCN5C(=O)O)C=C(C=C2)F HLKUAFQXZIWWAX-LMALLOCISA-N 0.000 claims description 2
- VFGMKSLSMTYVIH-FREGXXQWSA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)CNC(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC(C)(C)C3=NC4=CC=CC=C4N3)CNC(=O)O)C=C(C=C2)F VFGMKSLSMTYVIH-FREGXXQWSA-N 0.000 claims description 2
- YVSVPYDBLWZNOA-LMALLOCISA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC3(CC3)C4=NC5=CC=CC=C5N4)C6COCCN6C(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCC3(CC3)C4=NC5=CC=CC=C5N4)C6COCCN6C(=O)O)C=C(C=C2)F YVSVPYDBLWZNOA-LMALLOCISA-N 0.000 claims description 2
- DXZSWYQYGILTFX-FREGXXQWSA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=C(C=CC(=C4N3)OC)Cl)CN(C)C(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=C(C=CC(=C4N3)OC)Cl)CN(C)C(=O)O)C=C(C=C2)F DXZSWYQYGILTFX-FREGXXQWSA-N 0.000 claims description 2
- GFAVBVNVVBMGRL-FREGXXQWSA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=C(C=CC(=C4N3)OC)OC)CNC(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=C(C=CC(=C4N3)OC)OC)CNC(=O)O)C=C(C=C2)F GFAVBVNVVBMGRL-FREGXXQWSA-N 0.000 claims description 2
- OPNJAZPBIWUKOY-XTEPFMGCSA-N CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=CC=CC=C4N3)CNC(=O)O)C=C(C=C2)F Chemical compound CC(C)[C@H]1C2=C(CC[C@@]1(CCN(C)CCCC3=NC4=CC=CC=C4N3)CNC(=O)O)C=C(C=C2)F OPNJAZPBIWUKOY-XTEPFMGCSA-N 0.000 claims description 2
- HFCJAYMEPWMHCS-UHFFFAOYSA-N CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CCC3(CCC4=C(C3C(C)C)C=CC(=C4)F)CN(C)C(=O)O Chemical compound CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CCC3(CCC4=C(C3C(C)C)C=CC(=C4)F)CN(C)C(=O)O HFCJAYMEPWMHCS-UHFFFAOYSA-N 0.000 claims description 2
- HHNVXQFSIYTYLZ-CMNOXULISA-N CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@@]3(CCC4=C([C@H]3C(C)C)C=CC(=C4)F)C5COCCN5C(=O)O Chemical compound CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@@]3(CCC4=C([C@H]3C(C)C)C=CC(=C4)F)C5COCCN5C(=O)O HHNVXQFSIYTYLZ-CMNOXULISA-N 0.000 claims description 2
- HHNVXQFSIYTYLZ-ZOAJNJICSA-N CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@]3(CCC4=C([C@@H]3C(C)C)C=CC(=C4)F)C5COCCN5C(=O)O Chemical compound CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@]3(CCC4=C([C@@H]3C(C)C)C=CC(=C4)F)C5COCCN5C(=O)O HHNVXQFSIYTYLZ-ZOAJNJICSA-N 0.000 claims description 2
- HFCJAYMEPWMHCS-JTSJOTPCSA-N CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@]3(CCC4=C([C@@H]3C(C)C)C=CC(=C4)F)CN(C)C(=O)O Chemical compound CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@]3(CCC4=C([C@@H]3C(C)C)C=CC(=C4)F)CN(C)C(=O)O HFCJAYMEPWMHCS-JTSJOTPCSA-N 0.000 claims description 2
- RFZTVUJIENHCBI-FREGXXQWSA-N CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@]3(CCC4=C([C@@H]3C(C)C)C=CC(=C4)F)CNC(=O)O Chemical compound CC1=C2C(=C(C=C1)C)N=C(N2)CCCN(C)CC[C@]3(CCC4=C([C@@H]3C(C)C)C=CC(=C4)F)CNC(=O)O RFZTVUJIENHCBI-FREGXXQWSA-N 0.000 claims description 2
- PJDNSIZKNZNKCJ-UVOPUAODSA-N CCN(CCCC(=O)NC1=C(C=CC(=C1N)C)C)CC[C@]2(CCC3=C([C@@H]2C(C)C)C=CC(=C3)F)C4COCCN4C(=O)O Chemical compound CCN(CCCC(=O)NC1=C(C=CC(=C1N)C)C)CC[C@]2(CCC3=C([C@@H]2C(C)C)C=CC(=C3)F)C4COCCN4C(=O)O PJDNSIZKNZNKCJ-UVOPUAODSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims 4
- 206010015037 epilepsy Diseases 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 208000014094 Dystonic disease Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000010118 dystonia Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 0 CC(CC=C1C)c2c1nc(*)[n]2C Chemical compound CC(CC=C1C)c2c1nc(*)[n]2C 0.000 description 2
- 208000032612 Glial tumor Diseases 0.000 description 2
- 206010018338 Glioma Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 208000005017 glioblastoma Diseases 0.000 description 2
- 102000038650 voltage-gated calcium channel activity Human genes 0.000 description 2
- 108091023044 voltage-gated calcium channel activity Proteins 0.000 description 2
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- GSWJJXXRQOXFCP-UHFFFAOYSA-N CC(C)c1nc(C=CCC2)c2[n]1C Chemical compound CC(C)c1nc(C=CCC2)c2[n]1C GSWJJXXRQOXFCP-UHFFFAOYSA-N 0.000 description 1
- GWZLMUNEDVTESN-UHFFFAOYSA-N Cc1nc(c(OC)ccc2OC)c2[nH]1 Chemical compound Cc1nc(c(OC)ccc2OC)c2[nH]1 GWZLMUNEDVTESN-UHFFFAOYSA-N 0.000 description 1
- NKHMPCKGOLWJGH-MSLMYCKWSA-N Cc1ncc(/C(/Cl)=C\C=C\OC)[nH]1 Chemical compound Cc1ncc(/C(/Cl)=C\C=C\OC)[nH]1 NKHMPCKGOLWJGH-MSLMYCKWSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762459355P | 2017-02-15 | 2017-02-15 | |
| US62/459,355 | 2017-02-15 | ||
| PCT/US2018/018356 WO2018152317A1 (en) | 2017-02-15 | 2018-02-15 | Calcium channel inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020507606A JP2020507606A (ja) | 2020-03-12 |
| JP2020507606A5 true JP2020507606A5 (https=) | 2021-03-25 |
| JP7134178B2 JP7134178B2 (ja) | 2022-09-09 |
Family
ID=63170001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019543998A Active JP7134178B2 (ja) | 2017-02-15 | 2018-02-15 | カルシウムチャネル阻害剤 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11130750B2 (https=) |
| EP (1) | EP3585376A4 (https=) |
| JP (1) | JP7134178B2 (https=) |
| KR (1) | KR102642063B1 (https=) |
| CN (1) | CN110545806A (https=) |
| AU (1) | AU2018221722B2 (https=) |
| CA (1) | CA3053781A1 (https=) |
| WO (1) | WO2018152317A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11602512B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12478604B1 (en) | 2016-07-22 | 2025-11-25 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11504347B1 (en) | 2016-07-22 | 2022-11-22 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11602513B1 (en) | 2016-07-22 | 2023-03-14 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US12186296B1 (en) | 2016-07-22 | 2025-01-07 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| UY37341A (es) | 2016-07-22 | 2017-11-30 | Flamel Ireland Ltd | Formulaciones de gamma-hidroxibutirato de liberación modificada con farmacocinética mejorada |
| US11986451B1 (en) | 2016-07-22 | 2024-05-21 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| CN113473980A (zh) | 2019-03-01 | 2021-10-01 | 弗拉梅尔爱尔兰有限公司 | 在进食状态下具有改善的药代动力学的γ-羟基丁酸酯组合物 |
| US11779557B1 (en) | 2022-02-07 | 2023-10-10 | Flamel Ireland Limited | Modified release gamma-hydroxybutyrate formulations having improved pharmacokinetics |
| US11583510B1 (en) | 2022-02-07 | 2023-02-21 | Flamel Ireland Limited | Methods of administering gamma hydroxybutyrate formulations after a high-fat meal |
Family Cites Families (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ213651A (en) * | 1984-10-11 | 1989-07-27 | Hoffmann La Roche | Tetrahydronapthalene derivatives and medicaments |
| CA1319144C (en) * | 1986-11-14 | 1993-06-15 | Quirico Branca | Tetrahydronaphthalene derivatives |
| AU2436792A (en) | 1991-08-16 | 1993-03-16 | Merck & Co., Inc. | Quinazoline derivatives as inhibitors of hiv reverse transcriptase |
| ATE267207T1 (de) | 1996-02-14 | 2004-06-15 | Isis Pharmaceuticals Inc | Kohlenhydratmodifizierte luckenhafte oligonukleotide |
| WO2001062740A1 (en) | 2000-02-25 | 2001-08-30 | South Alabama Medical Science Foundation | Mibefradil analogues and their use |
| AU2003237616B2 (en) | 2002-01-17 | 2007-07-05 | The University Of British Columbia | Bispecific antisense oligonucleotides that inhibit IGFBP-2 and IGFBP-5 and methods of using same |
| WO2004035000A2 (en) | 2002-10-17 | 2004-04-29 | Merck & Co., Inc. | Enhancement of sleep with t-type calcium channel antagonists |
| WO2005007124A2 (en) | 2003-07-23 | 2005-01-27 | Bristol-Myers Squibb Company | Substituted dihydropyrimidine inhibitors of calcium channel function |
| US7166603B2 (en) | 2003-07-23 | 2007-01-23 | Bristol-Myers Squibb Co. | Dihydropyrimidone inhibitors of calcium channel function |
| KR100610731B1 (ko) | 2004-02-24 | 2006-08-09 | 한국과학기술연구원 | Ｔ-형 칼슘 채널 차단제로서 유용한 ３,４-디히드로퀴나졸린유도체 및 그의 제조 방법 |
| US7504431B2 (en) | 2004-04-16 | 2009-03-17 | Bristol-Myers Squibb Company | Sulfonyl amide inhibitors of calcium channel function |
| JP4927735B2 (ja) | 2004-08-20 | 2012-05-09 | ユニバーシテイ・オブ・バージニア・パテント・フアウンデーシヨン | Ｔ型カルシウムチャネル阻害剤 |
| CA2576186A1 (en) | 2004-08-20 | 2006-03-02 | University Of Virginia Patent Foundation | T type calcium channel blockers and the treatment of diseases |
| CA2600868A1 (en) | 2005-03-09 | 2006-09-21 | Merck & Co., Inc. | Quinazolinone t-type calcium channel antagonists |
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2018
- 2018-02-15 AU AU2018221722A patent/AU2018221722B2/en active Active
- 2018-02-15 CA CA3053781A patent/CA3053781A1/en active Pending
- 2018-02-15 JP JP2019543998A patent/JP7134178B2/ja active Active
- 2018-02-15 US US16/486,399 patent/US11130750B2/en active Active
- 2018-02-15 EP EP18755079.3A patent/EP3585376A4/en active Pending
- 2018-02-15 WO PCT/US2018/018356 patent/WO2018152317A1/en not_active Ceased
- 2018-02-15 KR KR1020197027037A patent/KR102642063B1/ko active Active
- 2018-02-15 CN CN201880024040.6A patent/CN110545806A/zh active Pending
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