JP2015508415A5 - - Google Patents
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- JP2015508415A5 JP2015508415A5 JP2014552332A JP2014552332A JP2015508415A5 JP 2015508415 A5 JP2015508415 A5 JP 2015508415A5 JP 2014552332 A JP2014552332 A JP 2014552332A JP 2014552332 A JP2014552332 A JP 2014552332A JP 2015508415 A5 JP2015508415 A5 JP 2015508415A5
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- Prior art keywords
- substituted
- branched
- optionally substituted
- compound according
- linear
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 17
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 150000002148 esters Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 239000012453 solvate Substances 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000004122 cyclic group Chemical group 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 238000010276 construction Methods 0.000 claims 8
- -1 2,3-dimethylbutyl Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 5
- 125000004450 alkenylene group Chemical group 0.000 claims 5
- 125000004419 alkynylene group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000005916 2-methylpentyl group Chemical group 0.000 claims 3
- 125000005917 3-methylpentyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004452 carbocyclyl group Chemical group 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WXTWRNDOOKCTTF-OAHLLOKOSA-N C[C@H](c1ccccc1)[n]1c(C(OC2(CCN(C)CC2)C(OC)=O)=O)cnc1 Chemical compound C[C@H](c1ccccc1)[n]1c(C(OC2(CCN(C)CC2)C(OC)=O)=O)cnc1 WXTWRNDOOKCTTF-OAHLLOKOSA-N 0.000 description 1
- FZJZGQQRMUYBNL-MRXNPFEDSA-N C[C@H](c1ccccc1)[n]1c(C(OCCCNCCCC(OC)=O)=O)cnc1 Chemical compound C[C@H](c1ccccc1)[n]1c(C(OCCCNCCCC(OC)=O)=O)cnc1 FZJZGQQRMUYBNL-MRXNPFEDSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261586450P | 2012-01-13 | 2012-01-13 | |
| US61/586,450 | 2012-01-13 | ||
| US201261622627P | 2012-04-11 | 2012-04-11 | |
| US61/622,627 | 2012-04-11 | ||
| PCT/US2013/021245 WO2013106717A1 (en) | 2012-01-13 | 2013-01-11 | Anesthetic compounds and related methods of use |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015508415A JP2015508415A (ja) | 2015-03-19 |
| JP2015508415A5 true JP2015508415A5 (enExample) | 2016-08-18 |
| JP6196986B2 JP6196986B2 (ja) | 2017-09-13 |
Family
ID=48781947
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014552332A Active JP6196986B2 (ja) | 2012-01-13 | 2013-01-11 | 麻酔化合物および関連する使用方法 |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US9156825B2 (enExample) |
| EP (2) | EP2802325B1 (enExample) |
| JP (1) | JP6196986B2 (enExample) |
| CN (2) | CN104168899B (enExample) |
| AU (1) | AU2013207811B2 (enExample) |
| BR (1) | BR112014017230A2 (enExample) |
| CA (1) | CA2861071C (enExample) |
| CY (1) | CY1118842T1 (enExample) |
| DK (1) | DK2802325T3 (enExample) |
| EA (1) | EA027976B1 (enExample) |
| ES (1) | ES2617536T3 (enExample) |
| HR (1) | HRP20170330T1 (enExample) |
| HU (1) | HUE030892T2 (enExample) |
| IN (1) | IN2014DN06132A (enExample) |
| LT (1) | LT2802325T (enExample) |
| NZ (1) | NZ627274A (enExample) |
| PL (1) | PL2802325T3 (enExample) |
| PT (1) | PT2802325T (enExample) |
| RS (1) | RS56025B1 (enExample) |
| SG (1) | SG11201403980VA (enExample) |
| SI (1) | SI2802325T1 (enExample) |
| SM (1) | SMT201700145T1 (enExample) |
| WO (1) | WO2013106717A1 (enExample) |
| ZA (1) | ZA201405248B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3360863B1 (en) * | 2015-10-10 | 2022-04-20 | Jiangsu Nhwaluokang Pharmaceutical Research and Development Co., Ltd. | Etomidate derivative and intermediate, preparation method and use thereof |
| CN105663042A (zh) * | 2016-02-03 | 2016-06-15 | 北京蓝丹医药科技有限公司 | 一种稳定的麻醉药物脂肪乳及其制备方法 |
| CN107382870A (zh) * | 2016-05-17 | 2017-11-24 | 四川海思科制药有限公司 | N‑取代咪唑羧酸酯类化合物及其制备方法和在医药上的用途 |
| CN107445898A (zh) * | 2016-05-30 | 2017-12-08 | 四川海思科制药有限公司 | N‑取代咪唑羧酸酯类化合物及其制备方法和在医药上的用途 |
| CN107522662A (zh) * | 2016-06-16 | 2017-12-29 | 四川海思科制药有限公司 | N‑取代咪唑羧酸酯类化合物及其制备方法和在医药上的用途 |
| CN107641105A (zh) * | 2016-07-22 | 2018-01-30 | 四川海思科制药有限公司 | N‑取代咪唑羧酸酯类化合物及其制备方法和在医药上的用途 |
| CN106432163A (zh) * | 2016-09-29 | 2017-02-22 | 山东东方农药科技实业有限公司 | 一种螺环内酯类化合物、其合成方法以及其用途 |
| CN107652239B (zh) * | 2017-02-24 | 2020-08-04 | 四川大学华西医院 | N-取代咪唑羧酸酯类化合物、制备方法及用途 |
| CN109776509B (zh) * | 2018-01-30 | 2023-07-07 | 成都麻沸散医药科技有限公司 | 一种n-取代咪唑甲酸酯类衍生物及其用途 |
| CN109053410A (zh) * | 2018-08-06 | 2018-12-21 | 兰博尔开封科技有限公司 | 一种合成1-羟基环己基甲酸的新工艺及应用 |
| BR112021004656A2 (pt) | 2018-09-26 | 2021-06-01 | Jiangsu Hengrui Medicine Co., Ltd. | conjugado fármaco-ligante de análogo exatecano, método para preparar o mesmo e aplicação do mesmo |
| MY209065A (en) | 2018-09-30 | 2025-06-18 | Jiangsu Hansoh Pharmaceutical Group Co Ltd | Anti-b7h3 antibody-exatecan analog conjugate and medicinal use thereof |
| CN109761906B (zh) * | 2019-03-02 | 2023-08-11 | 成都麻沸散医药科技有限公司 | 一种取代咪唑甲酸酯类衍生物及其用途 |
| CN110003188B (zh) * | 2019-03-27 | 2022-08-26 | 成都麻沸散医药科技有限公司 | 取代吡咯甲酸酯类衍生物及其用途 |
| AU2020347715A1 (en) | 2019-09-18 | 2022-04-07 | Systimmune, Inc. | Camptothecin derivative and conjugate thereof |
| CN112174890B (zh) * | 2020-10-09 | 2022-05-27 | 成都麻沸散医药科技有限公司 | 酮取代杂环化合物及其麻醉作用 |
| WO2021068943A1 (zh) * | 2019-10-11 | 2021-04-15 | 成都麻沸散医药科技有限公司 | 一种取代氮杂环化合物及其麻醉作用 |
| CN110669017B (zh) * | 2019-10-11 | 2023-08-04 | 成都麻沸散医药科技有限公司 | 多取代三唑甲酸酯类衍生物及其用途 |
| AU2020402006A1 (en) | 2019-12-12 | 2022-07-07 | Jiangsu Hengrui Medicine Co., Ltd. | Anti-claudin antibody-drug conjugate and pharmaceutical use thereof |
| JP7827624B2 (ja) | 2019-12-16 | 2026-03-10 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 抗ｃｅａ抗体－エキサテカン類似体複合体及びその医薬用途 |
| TWI891714B (zh) | 2020-01-22 | 2025-08-01 | 大陸商江蘇恆瑞醫藥股份有限公司 | 抗trop-2抗體-依喜替康類似物偶聯物及其醫藥用途 |
| WO2021148003A1 (zh) | 2020-01-22 | 2021-07-29 | 上海森辉医药有限公司 | 艾日布林衍生物的药物偶联物、其制备方法及其在医药上的应用 |
| US20230140397A1 (en) | 2020-03-25 | 2023-05-04 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | Anti-psma antibody-exatecan analogue conjugate and medical use thereof |
| WO2021190581A1 (zh) | 2020-03-25 | 2021-09-30 | 江苏恒瑞医药股份有限公司 | 一种含抗体药物偶联物的药物组合物及其用途 |
| JP7730836B2 (ja) | 2020-03-25 | 2025-08-28 | 江蘇恒瑞医薬股▲ふん▼有限公司 | 抗体薬物複合体の調製方法 |
| KR20240037267A (ko) | 2021-07-22 | 2024-03-21 | 상하이 센후이 메디슨 컴퍼니 리미티드 | 에리불린 유도체의 약물 접합체 |
| EP4454662A4 (en) | 2021-12-23 | 2025-04-23 | Jiangsu Hengrui Pharmaceuticals Co., Ltd. | ANTI-DLL3 ANTIBODY AND PHARMACEUTICAL USE THEREOF, AND ANTIBODY-DRUG CONJUGATE CONTAINING AN ANTI-DLL3 ANTIBODY |
| KR20260040624A (ko) | 2023-07-25 | 2026-03-25 | 지앙수 헨그루이 파마슈티컬스 컴퍼니 리미티드 | c-Met를 표적으로 하는 항체-약물 접합체 및 이의 의학적 용도 |
| WO2025195256A1 (zh) * | 2024-03-22 | 2025-09-25 | 四川科伦药物研究院有限公司 | 羧酸酯类化合物及其制备方法和用途 |
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| US20080206138A1 (en) | 2003-08-06 | 2008-08-28 | Ilse Zolle | Radiolabelled Phenylethyl Imidazole Carboxylic Acid Ester Derivatives |
| US7189859B2 (en) | 2003-08-06 | 2007-03-13 | Ilse Zolle | Radiolabelled phenylethyl imidazole carboxylic acid ester derivatives |
| JP2008510726A (ja) | 2004-08-20 | 2008-04-10 | エントレメッド インコーポレイテッド | プロテイナーゼ活性化受容体アンタゴニストを含む組成物および方法 |
| US7592362B2 (en) * | 2006-01-19 | 2009-09-22 | Pfizer Limited | Substituted imidazoles |
| CA2636787A1 (en) | 2006-01-24 | 2007-08-02 | Nippon Zoki Pharmaceutical Co., Ltd | Novel histidine derivatives |
| US8071785B2 (en) * | 2006-06-09 | 2011-12-06 | Ge Healthcare Limited | Synthesis and evaluation of 18F-labelled-alkyl-1-[(1R)-1-phenylethyl]-1H-imidazole-5-carboxylate as a tracer for the quantification of β-11-hydroxylase enzyme in the adrenal glands |
| JP5301441B2 (ja) | 2007-07-23 | 2013-09-25 | 日本臓器製薬株式会社 | 新規ヒスチジン誘導体 |
| BRPI0910072A2 (pt) * | 2008-03-31 | 2017-05-30 | Massachusetts Gen Hospital | composto, composição farmaceutic, e, método para prover anestesia a um mamífero. |
| WO2011005969A2 (en) * | 2009-07-10 | 2011-01-13 | The General Hospital Corporation | Etomidate analogues that do not inhibit adrenocortical steroid synthesis |
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