JP2016525072A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016525072A5 JP2016525072A5 JP2016520388A JP2016520388A JP2016525072A5 JP 2016525072 A5 JP2016525072 A5 JP 2016525072A5 JP 2016520388 A JP2016520388 A JP 2016520388A JP 2016520388 A JP2016520388 A JP 2016520388A JP 2016525072 A5 JP2016525072 A5 JP 2016525072A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- dcm
- methyl
- meoh
- vacuo
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 6
- -1 and vitorterol) Chemical compound 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 2
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HUCJFAOMUPXHDK-UHFFFAOYSA-N Xylometazoline Chemical compound CC1=CC(C(C)(C)C)=CC(C)=C1CC1=NCCN1 HUCJFAOMUPXHDK-UHFFFAOYSA-N 0.000 description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- WYWIFABBXFUGLM-UHFFFAOYSA-N oxymetazoline Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CC1=NCCN1 WYWIFABBXFUGLM-UHFFFAOYSA-N 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229960002052 salbutamol Drugs 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- NDAUXUAQIAJITI-LBPRGKRZSA-N (R)-salbutamol Chemical compound CC(C)(C)NC[C@H](O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-LBPRGKRZSA-N 0.000 description 1
- ZEBFPAXSQXIPNF-UHFFFAOYSA-N 2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1 ZEBFPAXSQXIPNF-UHFFFAOYSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- OTZJQCOQHUZTDP-UHFFFAOYSA-N 2-[2-[tert-butylsilyloxy(diphenyl)methyl]-4-[2-ethyl-3-[[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-methylamino]imidazo[1,2-b]pyridazin-6-yl]piperazin-1-yl]-1-pyrrolidin-1-ylethanone Chemical compound C(C)(C)(C)[SiH2]OC(C1N(CCN(C1)C=1C=CC=2N(N1)C(=C(N2)CC)N(C)C=2SC=C(N2)C2=CC=C(C=C2)F)CC(=O)N2CCCC2)(C2=CC=CC=C2)C2=CC=CC=C2 OTZJQCOQHUZTDP-UHFFFAOYSA-N 0.000 description 1
- IZEGJNWOOPXVJG-UHFFFAOYSA-N 2-chloro-1-(2,5-dimethylpyrrolidin-1-yl)ethanone Chemical compound CC1CCC(C)N1C(=O)CCl IZEGJNWOOPXVJG-UHFFFAOYSA-N 0.000 description 1
- OUVFWIHVZPQHJF-UHFFFAOYSA-N 5-ethenyl-5-methylcyclohexa-1,3-diene Chemical compound C=CC1(C)CC=CC=C1 OUVFWIHVZPQHJF-UHFFFAOYSA-N 0.000 description 1
- PJFHZKIDENOSJB-UHFFFAOYSA-N Budesonide/formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1.C1CC2=CC(=O)C=CC2(C)C2C1C1CC3OC(CCC)OC3(C(=O)CO)C1(C)CC2O PJFHZKIDENOSJB-UHFFFAOYSA-N 0.000 description 1
- UUSPQIGPKPHYBV-QFIPXVFZSA-N CCc1nc2ccc(nn2c1N(C)c1nc(cs1)-c1ccc(F)cc1)N1CCN(CC(=O)N2CCCC2)[C@H](CO)C1 Chemical compound CCc1nc2ccc(nn2c1N(C)c1nc(cs1)-c1ccc(F)cc1)N1CCN(CC(=O)N2CCCC2)[C@H](CO)C1 UUSPQIGPKPHYBV-QFIPXVFZSA-N 0.000 description 1
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 1
- YYAZJTUGSQOFHG-IAVNQIGZSA-N [(6s,8s,10s,11s,13s,14s,16r,17r)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate;2-(hydroxymethyl)-4-[1-hydroxy-2-[6-(4-phenylbutoxy)hexylamino]eth Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)C1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O YYAZJTUGSQOFHG-IAVNQIGZSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 229960003060 bambuterol Drugs 0.000 description 1
- ANZXOIAKUNOVQU-UHFFFAOYSA-N bambuterol Chemical compound CN(C)C(=O)OC1=CC(OC(=O)N(C)C)=CC(C(O)CNC(C)(C)C)=C1 ANZXOIAKUNOVQU-UHFFFAOYSA-N 0.000 description 1
- 102000016966 beta-2 Adrenergic Receptors Human genes 0.000 description 1
- 108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229940080593 budesonide / formoterol Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 1
- 229960000876 cinnarizine Drugs 0.000 description 1
- 229940109248 cromoglycate Drugs 0.000 description 1
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 229960003592 fexofenadine Drugs 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940114006 fluticasone / salmeterol Drugs 0.000 description 1
- 229960002848 formoterol Drugs 0.000 description 1
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- YZPMCVBCSSNXJG-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-2-carbaldehyde Chemical compound N1=CC=CC2=NC(C=O)=CN21 YZPMCVBCSSNXJG-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229960001361 ipratropium bromide Drugs 0.000 description 1
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 1
- 229960004958 ketotifen Drugs 0.000 description 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 description 1
- 229950008204 levosalbutamol Drugs 0.000 description 1
- 229940127212 long-acting beta 2 agonist Drugs 0.000 description 1
- 229940125386 long-acting bronchodilator Drugs 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- 229960005016 naphazoline Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229960000470 omalizumab Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960001528 oxymetazoline Drugs 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000012622 synthetic inhibitor Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229960001262 tramazoline Drugs 0.000 description 1
- QQJLHRRUATVHED-UHFFFAOYSA-N tramazoline Chemical compound N1CCN=C1NC1=CC=CC2=C1CCCC2 QQJLHRRUATVHED-UHFFFAOYSA-N 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 229960000833 xylometazoline Drugs 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361836831P | 2013-06-19 | 2013-06-19 | |
| US61/836,831 | 2013-06-19 | ||
| PCT/EP2014/062241 WO2014202458A1 (en) | 2013-06-19 | 2014-06-12 | Novel compounds and pharmaceutical compositions thereof for the treatment of inflammatory disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016525072A JP2016525072A (ja) | 2016-08-22 |
| JP2016525072A5 true JP2016525072A5 (https=) | 2017-08-10 |
| JP6435323B2 JP6435323B2 (ja) | 2018-12-05 |
Family
ID=50942280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016520388A Active JP6435323B2 (ja) | 2013-06-19 | 2014-06-12 | 炎症性障害の治療のための新規化合物及びその医薬組成物 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9796719B2 (https=) |
| EP (1) | EP3010922B1 (https=) |
| JP (1) | JP6435323B2 (https=) |
| CN (1) | CN105339370B (https=) |
| WO (1) | WO2014202458A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201501870D0 (en) * | 2015-02-04 | 2015-03-18 | Cancer Rec Tech Ltd | Autotaxin inhibitors |
| WO2016144706A2 (en) * | 2015-03-11 | 2016-09-15 | Pharmakea, Inc. | Autotaxin inhibitor compounds and uses thereof |
| AU2016270373A1 (en) | 2015-06-05 | 2018-01-04 | Vertex Pharmaceuticals Incorporated | Triazoles for the treatment of demyelinating diseases |
| WO2018106643A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Heterocyclic azoles for the treatment of demyelinating diseases |
| WO2018106641A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Pyrazoles for the treatment of demyelinating diseases |
| WO2018106646A1 (en) | 2016-12-06 | 2018-06-14 | Vertex Pharmaceuticals Incorporated | Aminotriazoles for the treatment of demyelinating diseases |
| US20200253959A1 (en) | 2017-08-09 | 2020-08-13 | Galapagos Nv | Compounds and pharmaceutical compositions thereof for use in the treatment of fibrotic diseases |
| CN109384803B (zh) * | 2017-08-09 | 2021-08-31 | 广州市恒诺康医药科技有限公司 | Atx抑制剂及其制备方法和应用 |
| CN111620865B (zh) * | 2018-02-14 | 2021-06-11 | 苏州信诺维医药科技股份有限公司 | 一种杂环化合物、其应用及含其的药物组合物 |
| CA3108809C (en) * | 2018-05-24 | 2023-08-29 | Guangzhou Henovcom Bioscience Co., Ltd. | Heteroaromatic compounds, pharmaceutical compositions and uses thereof |
| WO2019228403A1 (en) | 2018-05-29 | 2019-12-05 | Fronthera U.S. Pharmaceuticals Llc | Autotaxin inhibitors and uses thereof |
| IL279702B2 (en) | 2018-07-27 | 2024-05-01 | Mitsubishi Tanabe Pharma Corp | 3, 5-disubstituted pyridine and 3, 5-disubstituted pyridazine derivatives and pharmaceutical use of same |
| BR112021005445A2 (pt) * | 2018-10-29 | 2021-06-15 | Boehringer Ingelheim International Gmbh | piridazinas |
| IL284994B2 (en) | 2019-02-01 | 2024-10-01 | Wuhan Humanwell Innovative Drug Res And Development Center Limited Company | Pyrrolopyrimidine derivative and use thereof |
| TW202110831A (zh) * | 2019-06-04 | 2021-03-16 | 大陸商江蘇恆瑞醫藥股份有限公司 | 吡啶酮類衍生物、其製備方法及其在醫藥上的應用 |
| US11465982B2 (en) | 2019-07-22 | 2022-10-11 | Boehringer Ingelheim International Gmbh | Pyridazines |
| CN114127054B (zh) * | 2019-07-22 | 2024-04-09 | 勃林格殷格翰国际有限公司 | 作为用于治疗炎性气道或纤维化疾病的自分泌运动因子(atx)调节剂的n-甲基、n-(6-(甲氧基)哒嗪-3-基)胺衍生物 |
| US11485727B2 (en) | 2019-07-22 | 2022-11-01 | Boehringer Ingelheim International Gmbh | N-methyl, n-(6-(methoxy)pyridazin-3-yl) amine derivatives as autotaxin (ATX) modulators |
| CN112457296B (zh) | 2019-09-06 | 2023-11-07 | 武汉人福创新药物研发中心有限公司 | 嘧啶类化合物及其制备方法 |
| CN112778334B (zh) * | 2019-11-07 | 2022-04-15 | 广州市恒诺康医药科技有限公司 | 芳杂环化合物、其药物组合物及其应用 |
| JP2023505155A (ja) * | 2019-12-04 | 2023-02-08 | アプティニックス インコーポレイテッド | 神経変性疾患に関連する認知障害を治療する方法 |
| CN113493453B (zh) * | 2020-04-07 | 2023-06-16 | 江苏恒瑞医药股份有限公司 | 稠合芳香环类衍生物、其制备方法及其在医药上的应用 |
| US20230159931A1 (en) * | 2020-04-24 | 2023-05-25 | Cornell University | Targeting the palmotylation/depalmotylation cycle to treat inflammatory diseases |
| US20230295159A1 (en) * | 2020-07-09 | 2023-09-21 | Suzhou Ark Biopharmaceutical Co., Ltd. | Atx inhibitor, and preparation method therefor and use thereof |
| CN114315825A (zh) * | 2020-09-30 | 2022-04-12 | 江西济民可信集团有限公司 | 吡啶并咪唑衍生物及其制备方法和应用 |
| WO2022074459A2 (en) * | 2020-10-06 | 2022-04-14 | Ildong Pharmaceutical Co., Ltd. | Autotaxin inhibitor compounds |
| EP4242208A4 (en) * | 2020-11-04 | 2025-01-15 | Xizang Haisco Pharmaceutical Co., Ltd. | DEUTERATED DERIVATIVE USED AS ATX INHIBITOR, AND ITS APPLICATION |
| WO2022100727A1 (zh) * | 2020-11-16 | 2022-05-19 | 广州市恒诺康医药科技有限公司 | 咪唑并噻唑类化合物、其药物组合物及其用途 |
| JP2024502337A (ja) | 2021-01-05 | 2024-01-18 | ザイダス ライフサイエンシズ リミティド | オートタキシンの新規阻害剤 |
| IL313087B2 (en) * | 2021-11-25 | 2026-02-01 | Shanghai Jemincare Pharmaceuticals Co Ltd | ATX inhibitors, their preparation method, their application and their medicinal salt |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7893058B2 (en) * | 2006-05-15 | 2011-02-22 | Janssen Pharmaceutica Nv | Imidazolopyrazine compounds useful for the treatment of degenerative and inflammatory diseases |
| PT2029602E (pt) * | 2006-05-31 | 2010-07-08 | Galapagos Nv | Compostos de triazolopirazina uteis para o tratamento de doenãas degenerativas e inflamatërias |
| CN101454326A (zh) * | 2006-05-31 | 2009-06-10 | 加拉帕戈斯股份有限公司 | 用于治疗变性和炎性疾病的三唑并吡嗪化合物 |
| US8227603B2 (en) | 2006-08-01 | 2012-07-24 | Cytokinetics, Inc. | Modulating skeletal muscle |
| US8148369B2 (en) * | 2007-05-10 | 2012-04-03 | Janssen Pharmaceutica Nv | Fused pyrazine compounds useful for the treatment of degenerative and inflammatory diseases |
| CL2009001064A1 (es) * | 2008-05-07 | 2009-10-09 | Galapagos Nv | Compuestos derivados de imidazol-pirazina o triazol-pirazina fusionados, inhibidores de mapkapk5; composicion farmaceutica que comprende dichos compuestos; y uso para preparar un medicamento destinado al tratamiento de inflamacion, especialmente en la artritis reumatoide. |
| DE102008028905A1 (de) * | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| JO3041B1 (ar) * | 2008-07-25 | 2016-09-05 | Galapagos Nv | مركبات جديدة مفيدة لمعالجة الأمراض التنكسية والالتهابية |
| CN102216299B (zh) * | 2008-12-01 | 2015-02-11 | 默克专利有限公司 | 作为自体毒素抑制剂的2,5-二氨基取代的吡啶并[4,3-d]嘧啶化合物 |
| DE102008063667A1 (de) * | 2008-12-18 | 2010-07-01 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-°[1,2,4]triazolo[4,3-b]pyrimidin-derivate |
| TW201120043A (en) * | 2009-11-05 | 2011-06-16 | Galapagos Nv | Fused pyrazine compounds as their salts, useful for the treatment of degenerative and inflammatory diseases |
| CA2834166A1 (en) * | 2011-04-29 | 2012-11-01 | Amgen Inc. | Bicyclic pyridazine compounds as pim inhibitors |
| EP2714680B1 (en) * | 2011-05-27 | 2015-11-25 | Amira Pharmaceuticals, Inc. | Heterocyclic autotaxin inhibitors and uses thereof |
| RU2675818C2 (ru) | 2013-03-14 | 2018-12-25 | Галапаго Нв | Новые соединения и фармацевтические композиции, их содержащие, для лечения воспалительных расстройств |
-
2014
- 2014-06-12 EP EP14729895.4A patent/EP3010922B1/en active Active
- 2014-06-12 CN CN201480035018.3A patent/CN105339370B/zh active Active
- 2014-06-12 WO PCT/EP2014/062241 patent/WO2014202458A1/en not_active Ceased
- 2014-06-12 JP JP2016520388A patent/JP6435323B2/ja active Active
- 2014-06-12 US US14/898,327 patent/US9796719B2/en active Active
-
2017
- 2017-09-15 US US15/706,073 patent/US20180127425A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016525072A5 (https=) | ||
| JP2016503765A5 (https=) | ||
| DK2935274T3 (en) | 3-OXO-2,3,5,8-TETRAHYDRO- [1,2,4] TRIAZOLO [4,3-A] PYRIMIDINE DERIVATIVES FOR THE TREATMENT OF AIR TRACT | |
| JP2011529032A5 (https=) | ||
| JP4150672B2 (ja) | ナフチリジン誘導体、その製造およびそのホスホジエステラーゼイソ酵素４（ｐｄｅ４）阻害剤としての使用 | |
| Rano et al. | Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1, 2, 3, 4-tetrahydroquinoline platform | |
| TWI568735B (zh) | 新穎化合物 | |
| Banoglu et al. | 4, 5-Diarylisoxazol-3-carboxylic acids: A new class of leukotriene biosynthesis inhibitors potentially targeting 5-lipoxygenase-activating protein (FLAP) | |
| JP2011503118A (ja) | ヒト免疫不全ウイルスの複製阻害薬 | |
| NZ592723A (en) | Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd | |
| JP2011529033A5 (https=) | ||
| JP2007514704A (ja) | ピラゾロ［３，４−ｂ］ピリジン化合物およびホスホジエステラーゼ阻害剤としてのその使用 | |
| JP2007529485A (ja) | ピラゾロ’３，４−ｂ！ピリジン化合物、および４型ホスホジエステラーゼ（ｐｄｅ４）阻害剤としてのその使用 | |
| JP2014525919A5 (ja) | Ｐｉｍキナーゼ阻害剤及びその製造方法、並びに製薬上の使用 | |
| Pepe et al. | Synthesis and structure–activity relationship studies of novel dihydropyridones as androgen receptor modulators | |
| TWI568732B (zh) | 激酶抑制劑 | |
| EP2129661B1 (en) | Quinoline derivatives as crth2 receptor ligands | |
| JP2010522149A (ja) | Ｃｒｔｈ２アンタゴニストとしてのインドリジン酢酸誘導体 | |
| US20160168119A1 (en) | Autotaxin inhibitors | |
| US8551992B2 (en) | Aminooxazole inhibitors of cyclin dependent kinases | |
| Yarmolchuk et al. | An entry into hexahydro-2 H-thieno [2, 3-c] pyrrole 1, 1-dioxide derivatives | |
| CN101605544A (zh) | Crth2拮抗剂 | |
| Nagashima et al. | Novel quinuclidinyl heteroarylcarbamate derivatives as muscarinic receptor antagonists | |
| JP2011530587A (ja) | ムスカリン受容体アンタゴニストおよびβ２−アドレナリン受容体アゴニストを含む医薬品 | |
| Mallikarjuna et al. | Synthesis, anticancer and antituberculosis studies for [1-(4-chlorophenyl) Cyclopropyl](Piperazine-yl) Methanone derivates |