JP2016503765A5 - - Google Patents
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- JP2016503765A5 JP2016503765A5 JP2015548428A JP2015548428A JP2016503765A5 JP 2016503765 A5 JP2016503765 A5 JP 2016503765A5 JP 2015548428 A JP2015548428 A JP 2015548428A JP 2015548428 A JP2015548428 A JP 2015548428A JP 2016503765 A5 JP2016503765 A5 JP 2016503765A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- dihydro
- mmol
- acid
- ylmethoxy
- 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 description 14
- -1 C 6-10 arylene Rue ester Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000007429 general method Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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
- 229960000549 4-dimethylaminophenol Drugs 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
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002148 esters Chemical class 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
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229960002052 salbutamol Drugs 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-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
- LQMDOONLLAJAPZ-UHFFFAOYSA-N 1-ethynylcyclopentan-1-ol Chemical compound C#CC1(O)CCCC1 LQMDOONLLAJAPZ-UHFFFAOYSA-N 0.000 description 1
- VNPSLFACFFRWOZ-UHFFFAOYSA-N 1-prop-2-ynylimidazolidine-2,4-dione Chemical compound O=C1CN(CC#C)C(=O)N1 VNPSLFACFFRWOZ-UHFFFAOYSA-N 0.000 description 1
- PVKCAQKXTLCSBC-UHFFFAOYSA-N 1h-isoquinolin-4-one Chemical compound C1=CC=C2C(=O)C=NCC2=C1 PVKCAQKXTLCSBC-UHFFFAOYSA-N 0.000 description 1
- DDSYRKBWRSZSLA-UHFFFAOYSA-N 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-2-ylmethoxy)-n-(oxan-4-yl)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinoline-9-carboxamide Chemical compound C=1C=C(C=2N(C(N=C(OCC3OC4=CC=CN=C4OC3)C=2)=O)CC2)C2=CC=1C(=O)NC1CCOCC1 DDSYRKBWRSZSLA-UHFFFAOYSA-N 0.000 description 1
- RVXVETWLKMPLCF-UHFFFAOYSA-N 2-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-2-ylmethoxy)-n-(oxetan-3-ylmethyl)-4-oxo-6,7-dihydropyrimido[6,1-a]isoquinoline-9-carboxamide Chemical compound C=1C=C(C=2N(C(N=C(OCC3OC4=CC=CN=C4OC3)C=2)=O)CC2)C2=CC=1C(=O)NCC1COC1 RVXVETWLKMPLCF-UHFFFAOYSA-N 0.000 description 1
- CZNVPYABQUWSGP-UHFFFAOYSA-N 2-bromo-n-methyl-n-propan-2-ylacetamide Chemical compound CC(C)N(C)C(=O)CBr CZNVPYABQUWSGP-UHFFFAOYSA-N 0.000 description 1
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 1
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-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
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-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
- 241000124008 Mammalia Species 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
- 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
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 229940126157 adrenergic receptor agonist Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 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
- 125000003118 aryl group Chemical group 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
- 230000003796 beauty Effects 0.000 description 1
- 229940080593 budesonide / formoterol Drugs 0.000 description 1
- 229960001803 cetirizine Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 230000003111 delayed effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 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
- 229960003592 fexofenadine Drugs 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
- 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
- 229940125386 long-acting bronchodilator Drugs 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
- 229960005016 naphazoline Drugs 0.000 description 1
- 229960000470 omalizumab Drugs 0.000 description 1
- AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 1
- KTHZBRAXOLUNBN-UHFFFAOYSA-N oxetan-3-ylmethanamine Chemical compound NCC1COC1 KTHZBRAXOLUNBN-UHFFFAOYSA-N 0.000 description 1
- 229960001528 oxymetazoline Drugs 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 229960002586 roflumilast Drugs 0.000 description 1
- MNDBXUUTURYVHR-UHFFFAOYSA-N roflumilast Chemical compound FC(F)OC1=CC=C(C(=O)NC=2C(=CN=CC=2Cl)Cl)C=C1OCC1CC1 MNDBXUUTURYVHR-UHFFFAOYSA-N 0.000 description 1
- 229960004017 salmeterol Drugs 0.000 description 1
- 150000003431 steroids Chemical class 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
- 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
- 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 |
|---|---|---|---|
| US201261740028P | 2012-12-20 | 2012-12-20 | |
| US61/740,028 | 2012-12-20 | ||
| PCT/EP2013/076818 WO2014095798A1 (en) | 2012-12-20 | 2013-12-17 | Novel dihydropyrimidinoisoquinolinones and pharmaceutical compositions thereof for the treatment of inflammatory disorders (gpr84 antagonists) |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016503765A JP2016503765A (ja) | 2016-02-08 |
| JP2016503765A5 true JP2016503765A5 (https=) | 2017-01-26 |
| JP6293784B2 JP6293784B2 (ja) | 2018-03-14 |
Family
ID=49841660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015548428A Expired - Fee Related JP6293784B2 (ja) | 2012-12-20 | 2013-12-17 | 炎症性障害の治療のための新規ジヒドロピリミジノイソキノリノン及びその医薬組成物（ｇｐｒ８４アンタゴニスト） |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9708312B2 (https=) |
| EP (1) | EP2935262B1 (https=) |
| JP (1) | JP6293784B2 (https=) |
| CN (1) | CN104870445B (https=) |
| WO (1) | WO2014095798A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR089284A1 (es) | 2011-12-22 | 2014-08-13 | Galapagos Nv | Dihidropirimidinoisoquinolinonas y composiciones farmaceuticas de las mismas para el tratamiento de trastornos inflamatorios |
| GB201506894D0 (en) | 2015-04-23 | 2015-06-10 | Galapagos Nv | Novel dihydropyridoisoquinolinones and pharmaceutical compositions thereof for the treatment of inflammatory disorders |
| CN108530480B (zh) * | 2017-03-06 | 2022-06-28 | 中国科学院上海药物研究所 | Gpr84受体拮抗剂及其应用 |
| EP3403649A1 (en) | 2017-05-16 | 2018-11-21 | Bayer Pharma Aktiengesellschaft | Inhibitors and antagonists of gpr84 for the treatment of endometriosis |
| CN111343986A (zh) | 2017-11-15 | 2020-06-26 | 加拉帕戈斯股份有限公司 | 用于治疗纤维化疾病的化合物及其药物组合物 |
| WO2020007342A1 (zh) * | 2018-07-06 | 2020-01-09 | 中国科学院上海药物研究所 | 联苯磷酸酯类化合物作为gpr84拮抗剂的应用 |
| CR20220291A (es) * | 2019-12-19 | 2022-08-10 | Bayer Ag | Derivados de furoindazol |
| WO2021123394A1 (en) | 2019-12-20 | 2021-06-24 | University Of Copenhagen | G protein-coupled receptor modulators and a pharmaceutical composition |
| JP2024506858A (ja) | 2021-02-02 | 2024-02-15 | リミナル・バイオサイエンシーズ・リミテッド | Ｇｐｒ８４アンタゴニストおよびその使用 |
| CA3211437A1 (en) | 2021-02-23 | 2022-09-01 | Bayer Aktiengesellschaft | Furoindazole derivatives as gpr84 antagonists |
| WO2022194267A1 (zh) * | 2021-03-18 | 2022-09-22 | 武汉人福创新药物研发中心有限公司 | 一种gpr84拮抗剂及其制备方法和用途 |
| WO2022218372A1 (zh) * | 2021-04-14 | 2022-10-20 | 武汉人福创新药物研发中心有限公司 | 一种二氢嘧啶并异喹啉酮类衍生物及用途 |
| CA3218018A1 (en) | 2021-04-29 | 2022-11-03 | Bayer Aktiengesellschaft | Furoindazole derivatives as antagonists or inhibitors of gpr84 |
| US20250066335A1 (en) | 2021-06-18 | 2025-02-27 | University Of Copenhagen | Polysubstituted 4-hydroxypyridine and 4-hydroxyquinoline derivatives as gpr84 antagonists |
| JP7705966B2 (ja) * | 2021-06-21 | 2025-07-10 | 武漢人福創新薬物研発中心有限公司 | Ｇｐｒ８４アンタゴニストとしての三環式化合物 |
| CN115611944A (zh) * | 2021-07-15 | 2023-01-17 | 中国科学院上海药物研究所 | 不对称gpr84拮抗剂及其用途 |
| US20250171436A1 (en) | 2022-01-21 | 2025-05-29 | Xizang Haisco Pharmaceutical Co., Ltd. | Tricyclic Fused Heterocyclic PDE3/4 Dual Inhibitor and Use Thereof |
| WO2024083705A1 (en) | 2022-10-18 | 2024-04-25 | Bayer Aktiengesellschaft | Furoindazole derivatives for the treatment of pain |
| CN120569392A (zh) * | 2022-12-30 | 2025-08-29 | 广州市联瑞制药有限公司 | 三环类化合物及其制备方法和应用 |
| WO2024220480A2 (en) * | 2023-04-17 | 2024-10-24 | The Board Of Trustees Of The Leland Stanford Junior University | Method for detecting innate immune action in vivo using gpr84-pet |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2720085A1 (de) * | 1977-05-05 | 1978-11-16 | Hoechst Ag | Pyrimido(6,1-a)isochinolin-2-on- derivate |
| US7501512B2 (en) * | 2003-07-08 | 2009-03-10 | Smithkline Beecham Corporation | Chemical compounds |
| CA2621144A1 (en) * | 2005-09-02 | 2007-03-08 | Arena Pharmaceuticals, Inc. | Human g protein-coupled receptor and modulators thereof for the treatment of atherosclerosis and atherosclerotic disease and for the treatment of conditions related to mcp-1 expression |
| JP2011088847A (ja) * | 2009-10-21 | 2011-05-06 | Takeda Chem Ind Ltd | 三環性化合物およびその用途 |
| AR089284A1 (es) * | 2011-12-22 | 2014-08-13 | Galapagos Nv | Dihidropirimidinoisoquinolinonas y composiciones farmaceuticas de las mismas para el tratamiento de trastornos inflamatorios |
-
2013
- 2013-12-17 EP EP13811181.0A patent/EP2935262B1/en active Active
- 2013-12-17 US US14/653,323 patent/US9708312B2/en not_active Expired - Fee Related
- 2013-12-17 WO PCT/EP2013/076818 patent/WO2014095798A1/en not_active Ceased
- 2013-12-17 CN CN201380067345.2A patent/CN104870445B/zh not_active Expired - Fee Related
- 2013-12-17 JP JP2015548428A patent/JP6293784B2/ja not_active Expired - Fee Related
-
2017
- 2017-05-30 US US15/608,331 patent/US20180016275A1/en not_active Abandoned
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