JP2018534257A5 - - Google Patents
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- JP2018534257A5 JP2018534257A5 JP2018515975A JP2018515975A JP2018534257A5 JP 2018534257 A5 JP2018534257 A5 JP 2018534257A5 JP 2018515975 A JP2018515975 A JP 2018515975A JP 2018515975 A JP2018515975 A JP 2018515975A JP 2018534257 A5 JP2018534257 A5 JP 2018534257A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- ethyl
- amine
- oxaspiro
- decan
- 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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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NVGSPCSQFOQQPW-OAHLLOKOSA-N 2-[(9r)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]acetaldehyde Chemical compound C([C@@](C1)(CC=O)C=2N=CC=CC=2)COC21CCCC2 NVGSPCSQFOQQPW-OAHLLOKOSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- -1 sodium triacetoxyborohydride Chemical compound 0.000 description 3
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 3
- IGDBSYLULISNJI-UWVGGRQHSA-N (1S,2S)-2-methoxy-2,3-dihydro-1H-inden-1-amine Chemical compound CO[C@H]1Cc2ccccc2[C@@H]1N IGDBSYLULISNJI-UWVGGRQHSA-N 0.000 description 2
- HPESSUIKVPPELT-ZKMPZPQNSA-N (1S,2S)-2-methoxy-N-[2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]ethyl]-2,3-dihydro-1H-inden-1-amine Chemical compound CO[C@@H]1[C@H](C2=CC=CC=C2C1)NCC[C@]1(CCOC2(CCCC2)C1)C1=NC=CC=C1 HPESSUIKVPPELT-ZKMPZPQNSA-N 0.000 description 2
- YUMLNLMFBWBKSK-OHSXHVKISA-N (1S,4S)-4-ethoxy-N-[2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]ethyl]-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C(C)O[C@H]1CC[C@@H](C2=CC=CC=C12)NCC[C@]1(CCOC2(CCCC2)C1)C1=NC=CC=C1 YUMLNLMFBWBKSK-OHSXHVKISA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- POGYITUWKDFDGK-AZGAKELHSA-N (1'S)-N-[2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]ethyl]spiro[1,3-dioxolane-2,4'-2,3-dihydro-1H-naphthalene]-1'-amine Chemical compound N1=C(C=CC=C1)[C@@]1(CCOC2(CCCC2)C1)CCN[C@H]1CCC2(OCCO2)C2=CC=CC=C12 POGYITUWKDFDGK-AZGAKELHSA-N 0.000 description 1
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- DJHGTASRHCFVNH-RYUDHWBXSA-N (1S,4S)-4-ethoxy-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C(C)O[C@H]1CC[C@@H](C2=CC=CC=C12)N DJHGTASRHCFVNH-RYUDHWBXSA-N 0.000 description 1
- AEVBPXDFDKBGLT-YOUFYPILSA-N (2s,3s,4r,5r)-n-[2-[4-(diethoxyphosphorylmethyl)anilino]-2-oxoethyl]-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolane-2-carboxamide Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NC(=O)CNC(=O)[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(NC(=O)C=C2)=O)O1 AEVBPXDFDKBGLT-YOUFYPILSA-N 0.000 description 1
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
- UEXSVCDRFKTEDD-ZEQKJWHPSA-N (4R)-1-ethyl-N-[2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]ethyl]-3,4-dihydro-2H-quinolin-4-amine Chemical compound C12(OCC[C@](C1)(C1=NC=CC=C1)CCN[C@H]1C3=CC=CC=C3N(CC1)CC)CCCC2 UEXSVCDRFKTEDD-ZEQKJWHPSA-N 0.000 description 1
- UEXSVCDRFKTEDD-JYFHCDHNSA-N (4S)-1-ethyl-N-[2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]ethyl]-3,4-dihydro-2H-quinolin-4-amine Chemical compound CCN1CC[C@H](NCC[C@]2(CCOC3(CCCC3)C2)c2ccccn2)c2ccccc12 UEXSVCDRFKTEDD-JYFHCDHNSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DAPOGWRBGOPUFG-UHFFFAOYSA-N 1-ethyl-3,4-dihydro-2h-quinolin-4-amine Chemical compound C1=CC=C2N(CC)CCC(N)C2=C1 DAPOGWRBGOPUFG-UHFFFAOYSA-N 0.000 description 1
- UEXSVCDRFKTEDD-ANWICMFUSA-N 1-ethyl-N-[2-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]ethyl]-3,4-dihydro-2H-quinolin-4-amine Chemical compound C1C2(OCC[C@](C2)(C2=NC=CC=C2)CCNC2C3=C(C=CC=C3)N(CC2)CC)CCC1 UEXSVCDRFKTEDD-ANWICMFUSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- WUZBOJXXYMKMMF-UHFFFAOYSA-N COC1=CC2=NC=3N(C(N(C(C=3N2C=C1)=O)CCC)=O)CCCCNC(=O)C1=CC=C(C=C1)S(=O)(=O)F Chemical compound COC1=CC2=NC=3N(C(N(C(C=3N2C=C1)=O)CCC)=O)CCCCNC(=O)C1=CC=C(C=C1)S(=O)(=O)F WUZBOJXXYMKMMF-UHFFFAOYSA-N 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- 229940126639 Compound 33 Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510665328.X | 2015-10-15 | ||
| CN201510665328 | 2015-10-15 | ||
| CN201511032876 | 2015-12-31 | ||
| CN201511032876.5 | 2015-12-31 | ||
| PCT/CN2016/101064 WO2017063509A1 (zh) | 2015-10-15 | 2016-09-30 | 氧杂螺环类衍生物、其制备方法及其在医药上的应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018534257A JP2018534257A (ja) | 2018-11-22 |
| JP2018534257A5 true JP2018534257A5 (enExample) | 2019-10-10 |
| JP6824502B2 JP6824502B2 (ja) | 2021-02-03 |
Family
ID=58517778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018515975A Active JP6824502B2 (ja) | 2015-10-15 | 2016-09-30 | オキサスピロ誘導体、その製造方法、及び医薬におけるその適用 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US10442793B2 (enExample) |
| EP (1) | EP3354649B1 (enExample) |
| JP (1) | JP6824502B2 (enExample) |
| KR (1) | KR102703513B1 (enExample) |
| CN (1) | CN107001347B (enExample) |
| AU (1) | AU2016339404B2 (enExample) |
| CA (1) | CA3000761C (enExample) |
| DK (1) | DK3354649T3 (enExample) |
| ES (1) | ES2772689T3 (enExample) |
| HU (1) | HUE048032T2 (enExample) |
| MX (1) | MX382815B (enExample) |
| PL (1) | PL3354649T3 (enExample) |
| PT (1) | PT3354649T (enExample) |
| RU (1) | RU2733373C2 (enExample) |
| TW (1) | TWI727981B (enExample) |
| WO (1) | WO2017063509A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX388643B (es) * | 2017-04-14 | 2025-03-20 | Jiangsu Hengrui Medicine Co | Composicion farmaceutica que contiene agonista de mor y agonista de kor, y sus usos |
| EP3610875B1 (en) * | 2017-04-14 | 2020-10-07 | Jiangsu Hengrui Medicine Co., Ltd. | Opioid receptor (mor) agonist salt, fumarate salt i crystal form thereof and preparation method thereof |
| CN108727347B (zh) * | 2017-04-14 | 2020-06-16 | 江苏恒瑞医药股份有限公司 | 一种阿片样物质受体(mor)激动剂的晶型及其制备方法 |
| CN109206417B (zh) * | 2017-07-04 | 2023-01-03 | 四川海思科制药有限公司 | 阿片受体激动剂及其应用 |
| US11072601B2 (en) | 2017-09-18 | 2021-07-27 | Shanghai Synergy Pharmaceutical Sciences Co., Ltd. | μ-opioid receptor agonist and preparation method therefor and use thereof in field of medicine |
| WO2019062804A1 (zh) | 2017-09-28 | 2019-04-04 | 江苏恒瑞医药股份有限公司 | 一种氧杂螺环类衍生物的制备方法及其中间体 |
| AU2018349930A1 (en) * | 2017-10-13 | 2020-04-16 | Shandong Luye Pharmaceutical Co., Ltd. | 2,6-dioxaspiro (4,5) decane derivatives and preparation method therefor and pharmaceutical applications thereof |
| JP2021505547A (ja) * | 2017-12-06 | 2021-02-18 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 疼痛を治療するための薬物の製造におけるｍｏｒアゴニストと組み合わせたｋｏｒアゴニストの使用 |
| CN111836807A (zh) * | 2018-04-28 | 2020-10-27 | 四川科伦博泰生物医药股份有限公司 | 氧杂螺环类化合物及其制备方法和用途 |
| CN108424372B (zh) * | 2018-05-11 | 2021-08-10 | 浙江华贝药业有限责任公司 | 2，2，2-三氟-n-[(s)-4-羰基四氢萘-1-基]-乙酰胺的纯化工艺 |
| CN111163778B (zh) * | 2018-05-14 | 2023-01-24 | 江苏恒瑞医药股份有限公司 | 一种mor受体激动剂药物组合物 |
| CN108707086B (zh) * | 2018-05-15 | 2021-08-10 | 浙江华贝药业有限责任公司 | 一种(1s，4s)-n-（4-羟基四氢萘-1-基）叔丁氧基碳酰胺的纯化工艺 |
| WO2020073985A1 (zh) * | 2018-10-12 | 2020-04-16 | 江苏恒瑞医药股份有限公司 | 一种阿片样物质受体(mor)激动剂的结晶形式及制备方法 |
| WO2020073984A1 (zh) * | 2018-10-12 | 2020-04-16 | 江苏恒瑞医药股份有限公司 | 一种阿片样物质受体(mor)激动剂的结晶形式及制备方法 |
| CN112334465B (zh) * | 2019-01-17 | 2024-06-11 | 上海海雁医药科技有限公司 | 三环取代的氧杂螺环衍生物、其制法与医药上的用途 |
| CN111662284B (zh) * | 2019-03-06 | 2021-08-10 | 上海海雁医药科技有限公司 | 双杂环取代的氧杂螺环衍生物、其制法与医药上的用途 |
| WO2021027304A1 (zh) * | 2019-08-14 | 2021-02-18 | 上海海雁医药科技有限公司 | 镇痛化合物、其制法与医药上的用途 |
| EP4092031A4 (en) * | 2020-01-17 | 2024-02-21 | Shanghai Haiyan Pharmaceutical Technology Co., Ltd. | AZABICYCLIC SUBSTITUTED OXASPIRO DERIVATIVE, METHOD FOR THE PRODUCTION THEREOF AND ITS MEDICAL USE |
| CN118221680A (zh) | 2020-01-17 | 2024-06-21 | 上海海雁医药科技有限公司 | 光学纯的氧杂螺环取代的吡咯并吡唑衍生物、其制法与医药上的用途 |
| CN113214264B (zh) * | 2020-01-21 | 2022-08-09 | 上海海雁医药科技有限公司 | 二氢吡咯并五元杂芳基取代的氧杂螺环衍生物、其制法与医药上的用途 |
| JP7781064B2 (ja) | 2020-01-22 | 2025-12-05 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 抗ｔｒｏｐ－２抗体－エキサテカン類似体複合体及びその医薬用途 |
| CN114075141B (zh) * | 2020-08-20 | 2025-02-25 | 上海致根医药科技有限公司 | 阿片受体“偏向性”配体、其制备方法及其在医药上的应用 |
| CN114539257B (zh) * | 2020-11-24 | 2023-08-11 | 江苏恒瑞医药股份有限公司 | 嘧啶二酮类螺环衍生物、其制备方法及其在医药上的应用 |
| JP7751645B2 (ja) | 2020-12-29 | 2025-10-08 | 上海海雁医薬科技有限公司 | オキシスピロ環置換ピロロピラゾール誘導体及びその中間体並びにその調製方法 |
| WO2023284788A1 (zh) | 2021-07-13 | 2023-01-19 | 上海海雁医药科技有限公司 | Mor受体激动剂的药学上可接受的盐、其多晶型物及其用途 |
| WO2023011422A1 (zh) * | 2021-08-02 | 2023-02-09 | 上海枢境生物科技有限公司 | 氧杂螺环类衍生物、制备方法及其用途 |
| CN117263956A (zh) * | 2022-01-19 | 2023-12-22 | 天地恒一制药股份有限公司 | 阿片受体激动剂及其制备方法和用途 |
| CN116589451B (zh) * | 2022-02-11 | 2024-07-09 | 成都硕德药业有限公司 | 一种6-氧杂螺[4,5]癸烷类化合物的新晶型、用途及其制备方法 |
| CN117624138A (zh) * | 2022-08-29 | 2024-03-01 | 江苏恒瑞医药股份有限公司 | 一种氧杂螺环类衍生物的可药用盐、晶型及制备方法 |
| CN119894904B (zh) * | 2022-09-27 | 2025-12-30 | 上海枢境生物科技有限公司 | 一种含螺环类衍生物的盐、晶型及其制备方法和应用 |
| KR20250137614A (ko) | 2023-01-18 | 2025-09-18 | 상하이 센후이 메디슨 컴퍼니 리미티드 | 테트라히드로-1-나프틸아민 및 이의 유도체의 제조 방법 |
| WO2026026772A1 (zh) * | 2024-07-30 | 2026-02-05 | 上海枢境生物科技有限公司 | 氧杂螺环类衍生物的富马酸盐晶型及其制备方法和应用 |
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| ES2160534B1 (es) | 1999-12-30 | 2002-04-16 | Vita Invest Sa | Nuevos esteres derivados de (rr,ss)-2-hidroxibenzoato de 3-(2-dimetilaminometil-1-hidroxiciclohexil) fenilo. |
| DE10044649A1 (de) | 2000-09-08 | 2002-07-04 | Gruenenthal Gmbh | Substituierte 4-Phenyl-1-(1-phenyl-cyclohexyl)-1,2,3,6-tetrahydropyridine |
| DE102006033109A1 (de) * | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| US7999107B2 (en) * | 2007-01-31 | 2011-08-16 | Merck Sharp & Dohme Corp. | Substituted pyrano[2,3-B]pyridine derivatives as cannabinoid-1 receptor modulators |
| US20090028873A1 (en) | 2007-07-27 | 2009-01-29 | Auspex Pharmaceuticals, Inc. | Substituted cyclohexanols |
| AU2009308769B2 (en) | 2008-10-31 | 2015-03-12 | Pain Therapeutics, Inc. | Filamin A-binding anti-inflammatory analgesic |
| CN102741258B (zh) | 2009-06-17 | 2015-09-30 | 德州大学体系董事会 | 作为分离剂的环果聚糖的组成物及方法 |
| SI2688403T1 (sl) * | 2011-03-23 | 2017-08-31 | Trevena, Inc. | Ligandi opioidnih receptorjev in metode uporabe in izdelave istega |
| CN104159902B (zh) | 2011-12-12 | 2016-05-04 | 格吕伦塔尔有限公司 | 制备(1r,4r)-6’-氟-(N,N-二甲基-和N-甲基)-4-苯基-4’,9’-二氢-3’H-螺[环己烷-1,1’-吡喃并[3,4,b]吲哚]-4-胺的方法 |
| PL2880037T3 (pl) | 2012-08-03 | 2019-07-31 | Johnson Matthey Public Limited Company | Sposób wytwarzania oksykodonu |
| RS55593B1 (sr) | 2012-11-13 | 2017-06-30 | Array Biopharma Inc | Jedinjenja biciklične uree, tiouree, guanidina i cijanoguanidina korisna za lečenje bola |
-
2016
- 2016-09-30 WO PCT/CN2016/101064 patent/WO2017063509A1/zh not_active Ceased
- 2016-09-30 AU AU2016339404A patent/AU2016339404B2/en active Active
- 2016-09-30 DK DK16854888.1T patent/DK3354649T3/da active
- 2016-09-30 CA CA3000761A patent/CA3000761C/en active Active
- 2016-09-30 EP EP16854888.1A patent/EP3354649B1/en active Active
- 2016-09-30 JP JP2018515975A patent/JP6824502B2/ja active Active
- 2016-09-30 ES ES16854888T patent/ES2772689T3/es active Active
- 2016-09-30 HU HUE16854888A patent/HUE048032T2/hu unknown
- 2016-09-30 MX MX2018004175A patent/MX382815B/es unknown
- 2016-09-30 RU RU2018115569A patent/RU2733373C2/ru active
- 2016-09-30 PT PT168548881T patent/PT3354649T/pt unknown
- 2016-09-30 KR KR1020187012600A patent/KR102703513B1/ko active Active
- 2016-09-30 PL PL16854888T patent/PL3354649T3/pl unknown
- 2016-09-30 CN CN201680003945.6A patent/CN107001347B/zh active Active
- 2016-09-30 US US15/766,985 patent/US10442793B2/en active Active
- 2016-10-14 TW TW105133229A patent/TWI727981B/zh active
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