JP2021100969A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2021100969A5 JP2021100969A5 JP2021053182A JP2021053182A JP2021100969A5 JP 2021100969 A5 JP2021100969 A5 JP 2021100969A5 JP 2021053182 A JP2021053182 A JP 2021053182A JP 2021053182 A JP2021053182 A JP 2021053182A JP 2021100969 A5 JP2021100969 A5 JP 2021100969A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- carboxamide
- ethyl
- pyrazole
- dihydro
- 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
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 190
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 172
- -1 -CH 3 Chemical group 0.000 claims 73
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 43
- 239000005711 Benzoic acid Substances 0.000 claims 26
- 235000010233 benzoic acid Nutrition 0.000 claims 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- KGOMUMXJNKZCDA-UHFFFAOYSA-N C1NC=CN1CC2=C(C=C(C=C2)C(F)(F)F)C(F)(F)F Chemical compound C1NC=CN1CC2=C(C=C(C=C2)C(F)(F)F)C(F)(F)F KGOMUMXJNKZCDA-UHFFFAOYSA-N 0.000 claims 6
- ZXLOZYMBPKHFKM-UHFFFAOYSA-N 3-[[2,5-bis(trifluoromethyl)phenyl]methyl]-1,2-dihydroimidazole Chemical compound FC(C1=CC=C(C=C1CN1CNC=C1)C(F)(F)F)(F)F ZXLOZYMBPKHFKM-UHFFFAOYSA-N 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 4
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims 2
- UJHFCEIGEJFCBX-UHFFFAOYSA-N 2-(trifluoromethyl)-4-[[3-(trifluoromethyl)phenyl]methyl]-6,7-dihydro-5H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(C1=NN2C(N(CCC2)CC2=CC(=CC=C2)C(F)(F)F)=C1C(=O)N)(F)F UJHFCEIGEJFCBX-UHFFFAOYSA-N 0.000 claims 2
- KSEWMEXHJLSVPT-UHFFFAOYSA-N 2-(trifluoromethyl)-4-[[4-(trifluoromethyl)phenyl]methyl]-6,7-dihydro-5H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound FC(C1=NN2C(N(CCC2)CC2=CC=C(C=C2)C(F)(F)F)=C1C(=O)N)(F)F KSEWMEXHJLSVPT-UHFFFAOYSA-N 0.000 claims 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 2
- 125000006482 3-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(I)=C1[H])C([H])([H])* 0.000 claims 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 2
- IDNXVUDDZDHJGX-UHFFFAOYSA-N 4-[(2-chlorophenyl)methyl]-2-(trifluoromethyl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound ClC1=C(CN2C=3N(CCC2)N=C(C3C(=O)N)C(F)(F)F)C=CC=C1 IDNXVUDDZDHJGX-UHFFFAOYSA-N 0.000 claims 2
- AMMRJINDLHDRIJ-UHFFFAOYSA-N 4-[(3-chlorophenyl)methyl]-2-(trifluoromethyl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound ClC=1C=C(CN2C=3N(CCC2)N=C(C3C(=O)N)C(F)(F)F)C=CC1 AMMRJINDLHDRIJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 2
- JEXOSIVOIFWCSU-UHFFFAOYSA-N CC(C1=CC=C(C(F)(F)F)C=C1C)N1C=CNC1 Chemical compound CC(C1=CC=C(C(F)(F)F)C=C1C)N1C=CNC1 JEXOSIVOIFWCSU-UHFFFAOYSA-N 0.000 claims 2
- CKDONALRQYMQNJ-UHFFFAOYSA-N CC1=CC(=CC=C1CN1CNC=C1)C(F)(F)F Chemical compound CC1=CC(=CC=C1CN1CNC=C1)C(F)(F)F CKDONALRQYMQNJ-UHFFFAOYSA-N 0.000 claims 2
- RSQWFGBLKPLJQP-UHFFFAOYSA-N CCC1=CC=C(C(F)(F)F)C=C1CN1C=CNC1 Chemical compound CCC1=CC=C(C(F)(F)F)C=C1CN1C=CNC1 RSQWFGBLKPLJQP-UHFFFAOYSA-N 0.000 claims 2
- ZGFKPECFBHRPGJ-UHFFFAOYSA-N CN1CN(C=C1)CC1=CC(=CC=C1C(F)(F)F)C(F)(F)F Chemical compound CN1CN(C=C1)CC1=CC(=CC=C1C(F)(F)F)C(F)(F)F ZGFKPECFBHRPGJ-UHFFFAOYSA-N 0.000 claims 2
- RXLTVXRSZUCFCL-UHFFFAOYSA-N ClC1=CC=C(CN2C=3N(CCC2)N=C(C3C(=O)N)C(F)(F)F)C=C1 Chemical compound ClC1=CC=C(CN2C=3N(CCC2)N=C(C3C(=O)N)C(F)(F)F)C=C1 RXLTVXRSZUCFCL-UHFFFAOYSA-N 0.000 claims 2
- QMVDXRGZLCWHBY-UHFFFAOYSA-N FC(C(C=C1C(F)(F)F)=CC=C1N1C=CNC1)(F)F Chemical compound FC(C(C=C1C(F)(F)F)=CC=C1N1C=CNC1)(F)F QMVDXRGZLCWHBY-UHFFFAOYSA-N 0.000 claims 2
- ZYTVUAXKDWNTNW-UHFFFAOYSA-N FC(C(C=C1CN2C=CNC2)=CC=C1C1=CC=CC=C1)(F)F Chemical compound FC(C(C=C1CN2C=CNC2)=CC=C1C1=CC=CC=C1)(F)F ZYTVUAXKDWNTNW-UHFFFAOYSA-N 0.000 claims 2
- HUCTVUPALHMDMU-UHFFFAOYSA-N FC(C1=CC=C(C(F)(F)F)C(N2C=CNC2)=C1)(F)F Chemical compound FC(C1=CC=C(C(F)(F)F)C(N2C=CNC2)=C1)(F)F HUCTVUPALHMDMU-UHFFFAOYSA-N 0.000 claims 2
- KZUCYBAYBWNPEB-UHFFFAOYSA-N FC(C1=CC=C(C=C1CN1CNC=C1)C(F)(F)F)F Chemical compound FC(C1=CC=C(C=C1CN1CNC=C1)C(F)(F)F)F KZUCYBAYBWNPEB-UHFFFAOYSA-N 0.000 claims 2
- WXGKQRCUUWPJSW-UHFFFAOYSA-N FC(C1=CC=CC(C(F)(F)F)=C1CN1C=CNC1)(F)F Chemical compound FC(C1=CC=CC(C(F)(F)F)=C1CN1C=CNC1)(F)F WXGKQRCUUWPJSW-UHFFFAOYSA-N 0.000 claims 2
- JCCWSGDPKMLGTD-UHFFFAOYSA-N FC(C1=NN2C(N(CCC2)C2=CC=C(C=C2)C(F)(F)F)=C1C(=O)N)(F)F Chemical compound FC(C1=NN2C(N(CCC2)C2=CC=C(C=C2)C(F)(F)F)=C1C(=O)N)(F)F JCCWSGDPKMLGTD-UHFFFAOYSA-N 0.000 claims 2
- YKJDETHKFXRFSK-UHFFFAOYSA-N FC(C1=NN2C(N(CCC2)CC2=C(C=CC=C2)C(F)(F)F)=C1C(=O)N)(F)F Chemical compound FC(C1=NN2C(N(CCC2)CC2=C(C=CC=C2)C(F)(F)F)=C1C(=O)N)(F)F YKJDETHKFXRFSK-UHFFFAOYSA-N 0.000 claims 2
- OMUHVUSRKIFYBS-UHFFFAOYSA-N FC(CO)(F)C1=CC=C(C=C1CN1CNC=C1)C(F)(F)F Chemical compound FC(CO)(F)C1=CC=C(C=C1CN1CNC=C1)C(F)(F)F OMUHVUSRKIFYBS-UHFFFAOYSA-N 0.000 claims 2
- DUYTUUFUZIJQED-UHFFFAOYSA-N FCC1=CC=C(C=C1CN1CNC=C1)C(F)(F)F Chemical compound FCC1=CC=C(C=C1CN1CNC=C1)C(F)(F)F DUYTUUFUZIJQED-UHFFFAOYSA-N 0.000 claims 2
- AYCDVHZVHJJZOS-HNNXBMFYSA-N N-[(1S)-1-(4-cyclopropylphenyl)ethyl]-6-(trifluoromethyl)-1-[[4-(trifluoromethyl)phenyl]methyl]-2,3-dihydroimidazo[1,2-b]pyrazole-7-carboxamide Chemical compound C[C@H](NC(=O)C1=C2N(CC3=CC=C(C=C3)C(F)(F)F)CCN2N=C1C(F)(F)F)C1=CC=C(C=C1)C1CC1 AYCDVHZVHJJZOS-HNNXBMFYSA-N 0.000 claims 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 229940081066 picolinic acid Drugs 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- LRAVTXYAIWWXLQ-UHFFFAOYSA-N 2-(trifluoromethyl)-3-[[3-(trifluoromethyl)phenyl]methyl]-1,2-dihydroimidazole Chemical compound FC(F)(F)C1N(C=CN1)CC1=CC(=CC=C1)C(F)(F)F LRAVTXYAIWWXLQ-UHFFFAOYSA-N 0.000 claims 1
- ZQYAIENGHRVVNX-SFHVURJKSA-N N-[(1S)-1-[4-(benzenesulfonylcarbamoyl)phenyl]ethyl]-1-[[3-(trifluoromethoxy)phenyl]methyl]-6-(trifluoromethyl)-2,3-dihydroimidazo[1,2-b]pyrazole-7-carboxamide Chemical compound C[C@H](NC(=O)c1c(nn2CCN(Cc3cccc(OC(F)(F)F)c3)c12)C(F)(F)F)c1ccc(cc1)C(=O)NS(=O)(=O)c1ccccc1 ZQYAIENGHRVVNX-SFHVURJKSA-N 0.000 claims 1
- VXNCSZWNPZTPID-UHFFFAOYSA-N [2-(1,2-dihydroimidazol-3-ylmethyl)-4-(trifluoromethyl)phenyl]methanol Chemical compound OCC1=CC=C(C=C1CN1CNC=C1)C(F)(F)F VXNCSZWNPZTPID-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 0 C*([C@](*=C)c1ccccc1)N1c2c(C(N[C@](C)(C=C=C=*)C3=CC=C(*)**3)=O)c(C)n[n]2C*C*1 Chemical compound C*([C@](*=C)c1ccccc1)N1c2c(C(N[C@](C)(C=C=C=*)C3=CC=C(*)**3)=O)c(C)n[n]2C*C*1 0.000 description 3
- MMKXTBJWOWAZBO-OMAAJBKGSA-N CC(C(F)(F)F)/C(/C(N[C@@H](C)C(C=C1)=CCC1C(N=O)=O)=O)=C(/N(Cc1cccc(C(F)(F)F)c1)CC1)\N1N Chemical compound CC(C(F)(F)F)/C(/C(N[C@@H](C)C(C=C1)=CCC1C(N=O)=O)=O)=C(/N(Cc1cccc(C(F)(F)F)c1)CC1)\N1N MMKXTBJWOWAZBO-OMAAJBKGSA-N 0.000 description 1
- YDXGJXMMZFGYHU-AWEZNQCLSA-N C[C@@H](c(cc1)ccc1C(O)=O)NC(c1c(N(Cc2ccccc2)CC2)[n]2nc1C(F)(F)F)=O Chemical compound C[C@@H](c(cc1)ccc1C(O)=O)NC(c1c(N(Cc2ccccc2)CC2)[n]2nc1C(F)(F)F)=O YDXGJXMMZFGYHU-AWEZNQCLSA-N 0.000 description 1
- KJRRQXYWFQKJIP-UHFFFAOYSA-N Cc1c[o]cc1 Chemical compound Cc1c[o]cc1 KJRRQXYWFQKJIP-UHFFFAOYSA-N 0.000 description 1
- XZGLNCKSNVGDNX-UHFFFAOYSA-N Cc1n[nH]nn1 Chemical compound Cc1n[nH]nn1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562242734P | 2015-10-16 | 2015-10-16 | |
| US201562242748P | 2015-10-16 | 2015-10-16 | |
| US62/242,734 | 2015-10-16 | ||
| US62/242,748 | 2015-10-16 | ||
| BD252/2016 | 2016-10-13 | ||
| BD2522016 | 2016-10-13 | ||
| JP2018519749A JP6860559B2 (ja) | 2015-10-16 | 2016-10-14 | Ｅｐ４アンタゴニスト |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018519749A Division JP6860559B2 (ja) | 2015-10-16 | 2016-10-14 | Ｅｐ４アンタゴニスト |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021100969A JP2021100969A (ja) | 2021-07-08 |
| JP2021100969A5 true JP2021100969A5 (enExample) | 2021-10-14 |
| JP7090770B2 JP7090770B2 (ja) | 2022-06-24 |
Family
ID=58518017
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018519749A Active JP6860559B2 (ja) | 2015-10-16 | 2016-10-14 | Ｅｐ４アンタゴニスト |
| JP2021053182A Active JP7090770B2 (ja) | 2015-10-16 | 2021-03-26 | Ｅｐ４アンタゴニスト |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018519749A Active JP6860559B2 (ja) | 2015-10-16 | 2016-10-14 | Ｅｐ４アンタゴニスト |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US10316040B2 (enExample) |
| EP (1) | EP3362454B1 (enExample) |
| JP (2) | JP6860559B2 (enExample) |
| KR (1) | KR102684436B1 (enExample) |
| CN (1) | CN108473497B (enExample) |
| AU (1) | AU2016338679B2 (enExample) |
| BR (1) | BR112018007664B1 (enExample) |
| CA (1) | CA3002144C (enExample) |
| IL (1) | IL258737A (enExample) |
| MX (1) | MX390051B (enExample) |
| WO (1) | WO2017066633A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CR20180323A (es) | 2015-11-20 | 2018-08-06 | Idorsia Pharmaceuticals Ltd | Derivados de indol n-sustituídos como moduladores de los receptores de pge2 |
| WO2018210992A1 (en) | 2017-05-18 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | Pyrimidine derivatives |
| AU2018268311B2 (en) | 2017-05-18 | 2022-02-10 | Idorsia Pharmaceuticals Ltd | Pyrimidine derivatives as PGE2 receptor modulators |
| EP3625224B1 (en) | 2017-05-18 | 2021-08-04 | Idorsia Pharmaceuticals Ltd | N-substituted indole derivatives |
| US11325899B2 (en) | 2017-05-18 | 2022-05-10 | Idorsia Pharmaceuticals Ltd | Benzofurane and benzothiophene derivatives as PGE2 receptor modulators |
| WO2018210994A1 (en) | 2017-05-18 | 2018-11-22 | Idorsia Pharmaceuticals Ltd | Phenyl derivatives as pge2 receptor modulators |
| WO2019149286A1 (en) * | 2018-02-05 | 2019-08-08 | Shenzhen Ionova Life Science Co., Ltd. | Heterobicyclic carboxylic acids for treating cancer or inflammatory diseases |
| EP3759114A4 (en) * | 2018-03-02 | 2021-12-15 | Shenzhen Ionova Life Science Co., Ltd. | HETEROBICYCLIC CARBOXYLIC ACIDS AND THEIR SALTS |
| JP7488269B2 (ja) | 2019-01-22 | 2024-05-21 | キーセラ・（スーチョウ）・ファーマシューティカルズ・カンパニー・リミテッド | Ｐｇｅ２／ｅｐ４シグナル伝達を阻害する化合物、その製造方法及びその医薬における応用 |
| WO2022102731A1 (ja) | 2020-11-13 | 2022-05-19 | 小野薬品工業株式会社 | Ｅｐ４拮抗薬と免疫チェックポイント阻害物質との併用によるがん治療 |
Family Cites Families (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE294943C (enExample) | ||||
| GB8426447D0 (en) | 1984-10-19 | 1984-11-28 | Kodak Ltd | Photographic colour couplers |
| JPS6296940A (ja) | 1985-10-24 | 1987-05-06 | Fuji Photo Film Co Ltd | 熱現像感光材料 |
| US5126340A (en) | 1986-10-16 | 1992-06-30 | American Cyanamid Company | 4-[(substituted)alkylcarbonyl]-4,5-dihydro and -4,5,6,7-tetrahydro-7-[(substituted)-phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitriles |
| US4847256A (en) | 1986-10-16 | 1989-07-11 | American Cyanamid Company | 4,5-dihydro and 4,5,6,7-tetrahydropyrazolo(1,5-A)-pyrimidines |
| US4963553A (en) | 1986-10-16 | 1990-10-16 | American Cyanamid Co. | 4-[(substituted) alkylcarbonyl]-4,5-dihydro- and -4,5,6,7-tetrahydro-7-[(substituted)phenyl]pyrazolo[1,5-a]pyrimidines |
| US5215982A (en) | 1989-11-10 | 1993-06-01 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| DD294943A5 (de) | 1990-06-05 | 1991-10-17 | Wilhelm-Pieck-Uni. Rostock Direktorat Fuer Forschung,De | Verfahren zur herstellung von kondensierten n-heterocyclen |
| JP2631160B2 (ja) | 1990-11-06 | 1997-07-16 | 富士写真フイルム株式会社 | シアンカプラー、シアン画像形成方法及びハロゲン化銀カラー写真感光材料 |
| JPH04190348A (ja) | 1990-11-26 | 1992-07-08 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| US5210200A (en) | 1990-11-29 | 1993-05-11 | Fuji Photo Film Co., Ltd. | Heterocyclic dye compounds |
| US5880066A (en) | 1990-12-11 | 1999-03-09 | Monsanto Company | Safened herbicidal sulfonamide compositions |
| US5484760A (en) | 1990-12-31 | 1996-01-16 | Monsanto Company | Herbicide antidotes as safeners for reducing phytotoxicity resulting from synergistic interaction between herbicides and other pesticides |
| TW274551B (enExample) | 1991-04-16 | 1996-04-21 | Takeda Pharm Industry Co Ltd | |
| IL102183A (en) | 1991-06-27 | 1999-11-30 | Takeda Chemical Industries Ltd | Biphenyl substituted heterocyclic compounds their production and pharmaceutical compositions comprising them |
| TW284688B (enExample) | 1991-11-20 | 1996-09-01 | Takeda Pharm Industry Co Ltd | |
| JP2893100B2 (ja) | 1991-11-27 | 1999-05-17 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JP2772884B2 (ja) | 1992-01-28 | 1998-07-09 | 富士写真フイルム株式会社 | ハロゲン化銀カラー写真感光材料 |
| JPH05341430A (ja) | 1992-06-12 | 1993-12-24 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
| US5405969A (en) | 1993-12-10 | 1995-04-11 | Eastman Kodak Company | Manufacture of thioether compounds |
| US6472416B1 (en) | 1999-08-27 | 2002-10-29 | Abbott Laboratories | Sulfonylphenylpyrazole compounds useful as COX-2 inhibitors |
| JP4233238B2 (ja) | 2000-07-06 | 2009-03-04 | 富士フイルム株式会社 | インク用着色微粒子分散物、それを用いたインクジェット記録用インクおよびインクジェット記録方法 |
| US6897231B2 (en) | 2000-07-31 | 2005-05-24 | Signal Pharmaceuticals, Inc. | Indazole derivatives as JNK inhibitors and compositions and methods related thereto |
| KR20030082982A (ko) | 2001-03-14 | 2003-10-23 | 그뤼넨탈 게엠베하 | 치환된 피라졸로피리미딘 및 티아졸로피리미딘 |
| US6783558B2 (en) | 2001-03-15 | 2004-08-31 | Kao Corporation | Hair coloring method and composition |
| WO2003004497A1 (en) | 2001-07-05 | 2003-01-16 | Sumitomo Pharmaceuticals Company, Limited | Novel heterocyclic compound |
| JP2003222985A (ja) | 2001-11-22 | 2003-08-08 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料の感度を増加させる方法 |
| JP2003327860A (ja) | 2002-05-09 | 2003-11-19 | Konica Minolta Holdings Inc | 着色組成物、着色微粒子分散物、インクジェット用インク、インクジェット記録方法 |
| CA2494700C (en) | 2002-08-26 | 2011-06-28 | Takeda Pharmaceutical Company Limited | Calcium receptor modulating compound and use thereof |
| JP2004091369A (ja) | 2002-08-30 | 2004-03-25 | Sumitomo Pharmaceut Co Ltd | 新規ビフェニル化合物 |
| WO2004035563A1 (en) | 2002-10-17 | 2004-04-29 | Syngenta Participations Ag | 3-heterocyclylpyridine derivatives useful as herbicides |
| AU2003274025A1 (en) | 2002-10-17 | 2004-05-04 | Syngenta Participations Ag | Pyridine derivatives useful as herbicides |
| JP4608869B2 (ja) | 2002-12-12 | 2011-01-12 | コニカミノルタホールディングス株式会社 | 光電変換材料用半導体、光電変換素子及び太陽電池 |
| JP2004277337A (ja) * | 2003-03-14 | 2004-10-07 | Sumitomo Pharmaceut Co Ltd | ピラゾロ［１，５−ａ］ピリミジン誘導体 |
| JP4419421B2 (ja) | 2003-04-15 | 2010-02-24 | コニカミノルタホールディングス株式会社 | 光電変換材料用半導体、光電変換素子及び太陽電池 |
| JP4419424B2 (ja) | 2003-04-17 | 2010-02-24 | コニカミノルタホールディングス株式会社 | 光電変換材料用半導体、光電変換素子及び太陽電池 |
| JP2004355960A (ja) | 2003-05-29 | 2004-12-16 | Konica Minolta Holdings Inc | 光電変換材料用半導体、光電変換素子及び太陽電池 |
| JP2005035932A (ja) | 2003-07-15 | 2005-02-10 | Fuji Photo Film Co Ltd | ４−置換ピラゾロ［１，５−ａ］ピリミジンジオン誘導体の製造方法 |
| US7419978B2 (en) | 2003-10-22 | 2008-09-02 | Bristol-Myers Squibb Company | Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors |
| JP2005239611A (ja) | 2004-02-25 | 2005-09-08 | Takeda Chem Ind Ltd | ピラゾロピリミジン誘導体およびその用途 |
| US7288123B2 (en) | 2004-08-26 | 2007-10-30 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| CA2577119A1 (en) | 2004-08-26 | 2006-03-09 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| CN101142184A (zh) | 2004-10-12 | 2008-03-12 | 解码遗传Ehf公司 | 用于阻塞性动脉疾病的磺酰胺迫位取代的双环化合物 |
| WO2006044415A2 (en) | 2004-10-12 | 2006-04-27 | Decode Genetics, Inc. | Carboxylic acid peri - substituted bicyclics for occlusive artery disease |
| JP2006248195A (ja) | 2005-03-14 | 2006-09-21 | Fuji Photo Film Co Ltd | 感熱記録材料 |
| WO2006138418A2 (en) | 2005-06-14 | 2006-12-28 | President And Fellows Of Harvard College | Improvement of cognitive performance with sirtuin activators |
| WO2007058626A1 (en) | 2005-11-16 | 2007-05-24 | S*Bio Pte Ltd | Indazole compounds |
| JPWO2007102531A1 (ja) | 2006-03-08 | 2009-07-23 | 武田薬品工業株式会社 | 併用薬 |
| WO2007121578A1 (en) * | 2006-04-24 | 2007-11-01 | Merck Frosst Canada Ltd. | Indole amide derivatives as ep4 receptor antagonists |
| WO2008019309A1 (en) | 2006-08-04 | 2008-02-14 | Metabasis Therapeutics, Inc. | Novel inhibitors of fructose 1,6-bisphosphatase |
| AU2008221194B2 (en) | 2007-02-26 | 2013-06-27 | Merck Canada Inc. | Indole and indoline cyclopropyl amide derivatives as EP4 receptor antagonists |
| US8063249B1 (en) | 2008-04-25 | 2011-11-22 | Olema Pharmaceuticals, Inc. | Substituted triphenyl butenes |
| JP5151684B2 (ja) | 2008-05-23 | 2013-02-27 | コニカミノルタビジネステクノロジーズ株式会社 | トナーの製造方法およびトナー |
| JP2009282350A (ja) | 2008-05-23 | 2009-12-03 | Konica Minolta Business Technologies Inc | 静電荷像現像用トナー |
| JP2010026048A (ja) | 2008-07-16 | 2010-02-04 | Konica Minolta Business Technologies Inc | カラートナー |
| EP2320906B1 (en) | 2008-08-14 | 2016-02-24 | Beta Pharma Canada Inc. | Heterocyclic amide derivatives as ep4 receptor antagonists |
| JPWO2010024258A1 (ja) | 2008-08-29 | 2012-01-26 | 塩野義製薬株式会社 | Ｐｉ３ｋ阻害活性を有する縮環アゾール誘導体 |
| US8853125B2 (en) | 2008-09-24 | 2014-10-07 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
| WO2010048559A2 (en) | 2008-10-24 | 2010-04-29 | Calcimedica Inc. | Phenylpyrazole inhibitors of store operated calcium release |
| US8809344B2 (en) | 2008-10-29 | 2014-08-19 | Apath, Llc | Compounds, compositions, and methods for control of hepatitis C viral infections |
| WO2010053583A2 (en) | 2008-11-10 | 2010-05-14 | Dana Farber Cancer Institute | Small molecule cd4 mimetics and uses thereof |
| CN101671336B (zh) | 2009-09-23 | 2013-11-13 | 辽宁利锋科技开发有限公司 | 芳杂环并嘧啶衍生物和类似物及其制备方法和用途 |
| US20120295845A1 (en) | 2009-11-23 | 2012-11-22 | Pfizer Inc | Imidazo-pyrazoles as gpr119 inhibitors |
| CN102770159A (zh) * | 2010-02-22 | 2012-11-07 | 拉夸里亚创药株式会社 | Ep-4受体拮抗剂在治疗il-23介导疾病中的用途 |
| KR101478889B1 (ko) | 2010-02-26 | 2015-01-02 | 미쓰비시 타나베 파마 코퍼레이션 | 피라졸로피리미딘 화합물 및 ｐｄｅ10 억제제로서의 그의 용도 |
| WO2011156632A2 (en) | 2010-06-09 | 2011-12-15 | Georgetown University | Compositions and methods of treatment for tumors in the nervous system |
| CN103384668B (zh) | 2010-09-03 | 2017-05-31 | 福马Tm有限责任公司 | 用于抑制nampt的化合物和组合物 |
| GB2483736B (en) | 2010-09-16 | 2012-08-29 | Aragon Pharmaceuticals Inc | Estrogen receptor modulators and uses thereof |
| SMT201700008T1 (it) | 2010-09-21 | 2017-03-08 | Eisai R&D Man Co Ltd | Composizione farmaceutica |
| WO2012103071A2 (en) | 2011-01-25 | 2012-08-02 | Eisai R&D Management Co., Ltd. | Compounds and compositions |
| US9226929B2 (en) | 2011-03-02 | 2016-01-05 | Bayer Intellectual Property Gmbh | Pharmaceutically active disubstituted triazine derivatives |
| WO2012143522A1 (en) | 2011-04-20 | 2012-10-26 | Glaxo Group Limited | Tetrahydropyrazolo [1,5 -a] pyrimidine as anti -tuberculosis compounds |
| DK2729445T3 (en) | 2011-07-04 | 2016-01-18 | Rottapharm Biotech Srl | CYCLIC AMINE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS |
| WO2013036994A1 (en) | 2011-09-16 | 2013-03-21 | Biota Scientific Management Pty Ltd | Compounds for the treatment of hcv |
| US9169205B2 (en) | 2012-10-08 | 2015-10-27 | Boehringer Ingelheim International Gmbh | Pyrrolidine derivatives, pharmaceutical compositions and uses thereof |
| CN102977106B (zh) | 2012-12-12 | 2014-12-10 | 中国药科大学 | 一类具有外周镇痛作用的κ阿片受体激动剂 |
| SMT201700160T1 (it) | 2013-04-25 | 2017-05-08 | Beigene Ltd | Composti eterociclici fusi come inibitori di protein chinasi |
| CA2913035C (en) | 2013-05-20 | 2017-08-01 | University Of Washington Through Its Center For Commercialization | 5-aminopyrazole-4-carboxamide inhibitors of cdpk1 |
| JP5954278B2 (ja) | 2013-08-09 | 2016-07-20 | コニカミノルタ株式会社 | 静電荷像現像用トナー、その製造方法および画像形成方法 |
| FR3014687B1 (fr) | 2013-12-13 | 2016-11-25 | Oreal | Procede de coloration des matieres keratiniques a partir d'oligomeres et/ou de polymeres colores issus de coupleurs, composition et agent de coloration |
| CN110354266A (zh) | 2014-05-23 | 2019-10-22 | 卫材 R&D 管理有限公司 | 用于治疗癌症的组合疗法 |
| WO2016088903A1 (en) | 2014-12-05 | 2016-06-09 | Takeda Pharmaceutical Company Limited | Heterocyclic compounds |
-
2016
- 2016-10-14 CA CA3002144A patent/CA3002144C/en active Active
- 2016-10-14 WO PCT/US2016/057135 patent/WO2017066633A1/en not_active Ceased
- 2016-10-14 US US15/768,668 patent/US10316040B2/en active Active
- 2016-10-14 CN CN201680073562.6A patent/CN108473497B/zh active Active
- 2016-10-14 MX MX2018004664A patent/MX390051B/es unknown
- 2016-10-14 KR KR1020187013843A patent/KR102684436B1/ko active Active
- 2016-10-14 JP JP2018519749A patent/JP6860559B2/ja active Active
- 2016-10-14 AU AU2016338679A patent/AU2016338679B2/en active Active
- 2016-10-14 BR BR112018007664-3A patent/BR112018007664B1/pt active IP Right Grant
- 2016-10-14 EP EP16790486.1A patent/EP3362454B1/en active Active
-
2018
- 2018-04-16 IL IL258737A patent/IL258737A/en unknown
-
2019
- 2019-04-23 US US16/391,882 patent/US10941148B2/en active Active
-
2021
- 2021-01-05 US US17/141,557 patent/US11434246B2/en active Active
- 2021-03-26 JP JP2021053182A patent/JP7090770B2/ja active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2021100969A5 (enExample) | ||
| JP2018530595A5 (enExample) | ||
| CN102666493B (zh) | 作为nep抑制剂的取代的氨基甲酰基甲基氨基乙酸衍生物 | |
| KR101276136B1 (ko) | 화합물, 조성물 및 방법 | |
| ES2232502T3 (es) | Derivados de pirazolo(4,3-d)pirimidina. | |
| JP2004511469A5 (enExample) | ||
| ES2611588T3 (es) | Pirrolo[2,3-b]piridinas y pirrolo[2,3-b]pirimidinas sustituidas con heteroarilo como inhibidores de quinasas Janus | |
| JP5816369B2 (ja) | ２−アミノ−４−（ピリジン−２−イル）−５，６−ジヒドロ−４ｈ−１，３−オキサジン誘導体およびｂａｃｅ−１および／またはｂａｃｅ−２阻害剤としてのそれらの使用 | |
| RU2003112610A (ru) | Производные пиразола для лечения вирксных заболеваний | |
| JP2005509038A5 (enExample) | ||
| JP2009523812A5 (enExample) | ||
| JP2006500393A5 (enExample) | ||
| JP2004524301A5 (enExample) | ||
| JP2020520356A5 (enExample) | ||
| JP2008513515A5 (enExample) | ||
| CA2498275A1 (en) | Hydroxy alkyl substituted 1,3,8-triazaspiro[4.5]decan-4-one derivatives useful for the treatment of orl-1 receptor mediated disorders | |
| JP2007529484A5 (enExample) | ||
| CN101534904A (zh) | 治疗血小板过量的bcl抑制剂 | |
| ES2244752T3 (es) | Derivados de imidazo-pirimidina como ligandos para receptores de gaba. | |
| JP2014501720A (ja) | Ｎｅｐ阻害剤としての置換アミノビスフェニルペンタン酸誘導体 | |
| JP2013519724A5 (enExample) | ||
| CZ2001964A3 (cs) | Lék a farmaceutická kombinace pro léčení diabetu, rezistence na inzulín, obezitu, hyperglykémie, hypeinzulínem nebo zvýąené hladiny mastných kyselin | |
| JP2010513438A5 (enExample) | ||
| RU2010116352A (ru) | Производные 1,1,1-трифтор-2-гидрокси-3-фенилпропана | |
| JP2018532778A5 (enExample) |