JP2019525913A5 - - Google Patents
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- Publication number
- JP2019525913A5 JP2019525913A5 JP2019500355A JP2019500355A JP2019525913A5 JP 2019525913 A5 JP2019525913 A5 JP 2019525913A5 JP 2019500355 A JP2019500355 A JP 2019500355A JP 2019500355 A JP2019500355 A JP 2019500355A JP 2019525913 A5 JP2019525913 A5 JP 2019525913A5
- Authority
- JP
- Japan
- Prior art keywords
- amount
- organic solvent
- formula
- temperature
- membered heteroaryl
- 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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- 238000000034 method Methods 0.000 claims description 69
- 239000003960 organic solvent Substances 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 150000001412 amines Chemical class 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 24
- 239000003153 chemical reaction reagent Substances 0.000 claims description 24
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- -1 pyrazole ester Chemical class 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 20
- 239000002184 metal Substances 0.000 claims description 20
- 239000003586 protic polar solvent Substances 0.000 claims description 20
- 238000009901 transfer hydrogenation reaction Methods 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- 150000002009 diols Chemical class 0.000 claims description 12
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 11
- YLZYSVYZMDJYOT-UHFFFAOYSA-N 2-methoxypyrimidine Chemical compound COC1=NC=CC=N1 YLZYSVYZMDJYOT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001409 amidines Chemical class 0.000 claims description 10
- 230000000382 dechlorinating effect Effects 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- 238000005576 amination reaction Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 230000009435 amidation Effects 0.000 claims description 4
- 238000007112 amidation reaction Methods 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000006298 dechlorination reaction Methods 0.000 claims description 4
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 150000003840 hydrochlorides Chemical class 0.000 claims description 4
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 claims description 4
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZDXJMHCHULQXIS-UHFFFAOYSA-N 3-fluorooxy-3-oxopropanoic acid Chemical compound OC(=O)CC(=O)OF ZDXJMHCHULQXIS-UHFFFAOYSA-N 0.000 claims 2
- BEIMPPDDPZOYBR-UHFFFAOYSA-N 6-fluoro-1h-pyrimidin-2-one Chemical compound FC=1C=CNC(=O)N=1 BEIMPPDDPZOYBR-UHFFFAOYSA-N 0.000 claims 1
- 0 *C[n](c(*)c1)nc1-c(nc1O)nc(O)c1F Chemical compound *C[n](c(*)c1)nc1-c(nc1O)nc(O)c1F 0.000 description 7
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- JYAHXBWSCRHPMZ-UHFFFAOYSA-N Fc1c(C[n](c(-c2n[o]cc2)c2)nc2-c(nc2Cl)nc(Cl)c2F)cccc1 Chemical compound Fc1c(C[n](c(-c2n[o]cc2)c2)nc2-c(nc2Cl)nc(Cl)c2F)cccc1 JYAHXBWSCRHPMZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- UXYRXGFUANQKTA-UHFFFAOYSA-N OC(c1n[o]cc1)=O Chemical compound OC(c1n[o]cc1)=O UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 description 1
- BNQFOSYFEVDOMJ-UHFFFAOYSA-N Oc(nc(-c1n[n](Cc(cccc2)c2F)c(-c2n[o]cc2)c1)nc1Cl)c1F Chemical compound Oc(nc(-c1n[n](Cc(cccc2)c2F)c(-c2n[o]cc2)c1)nc1Cl)c1F BNQFOSYFEVDOMJ-UHFFFAOYSA-N 0.000 description 1
- LIVYVCAUBHXIMI-UHFFFAOYSA-N Oc1nc(-c2n[n](Cc(cccc3)c3F)c(-c3n[o]cc3)c2)ncc1F Chemical compound Oc1nc(-c2n[n](Cc(cccc3)c3F)c(-c3n[o]cc3)c2)ncc1F LIVYVCAUBHXIMI-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662359453P | 2016-07-07 | 2016-07-07 | |
| US62/359,453 | 2016-07-07 | ||
| PCT/US2017/040810 WO2018009597A1 (en) | 2016-07-07 | 2017-07-06 | Novel processes for preparation of soluble guanylate cyclase stimulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019525913A JP2019525913A (ja) | 2019-09-12 |
| JP2019525913A5 true JP2019525913A5 (enExample) | 2020-08-20 |
| JP7112384B2 JP7112384B2 (ja) | 2022-08-03 |
Family
ID=59416789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019500355A Active JP7112384B2 (ja) | 2016-07-07 | 2017-07-06 | 可溶性グアニル酸シクラーゼ刺激剤の新規な調製方法 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US11319308B2 (enExample) |
| EP (2) | EP4249488A3 (enExample) |
| JP (1) | JP7112384B2 (enExample) |
| KR (1) | KR102487872B1 (enExample) |
| CN (1) | CN109563077A (enExample) |
| AU (1) | AU2017291827B2 (enExample) |
| BR (1) | BR112019000291A2 (enExample) |
| CA (1) | CA3029375A1 (enExample) |
| CL (2) | CL2019000016A1 (enExample) |
| EA (1) | EA201990237A1 (enExample) |
| ES (1) | ES2963563T3 (enExample) |
| IL (1) | IL263995B (enExample) |
| MA (1) | MA45603A (enExample) |
| MX (2) | MX389920B (enExample) |
| SG (1) | SG11201900096QA (enExample) |
| WO (1) | WO2018009597A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3029375A1 (en) | 2016-07-07 | 2018-01-11 | Ironwood Pharmaceuticals, Inc. | Novel processes for preparation of soluble guanylate cyclase stimulators |
| WO2018009602A2 (en) * | 2016-07-07 | 2018-01-11 | Ironwood Pharmaceuticals, Inc. | Novel processes for preparation of soluble guanylate cyclase stimulators |
| WO2019161534A1 (en) * | 2018-02-22 | 2019-08-29 | Ironwood Pharmaceuticals, Inc. | Novel processes and intermediates for preparation of soluble guanylate cyclase stimulators |
| JP7357621B2 (ja) | 2018-01-10 | 2023-10-06 | サイクレリオン・セラピューティクス，インコーポレーテッド | 可溶性グアニル酸シクラーゼ刺激剤を調製するための新規のプロセスおよび中間体 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103038229B (zh) * | 2010-05-26 | 2016-05-11 | 桑诺维恩药品公司 | 杂芳基化合物及其使用方法 |
| EP2588465B1 (en) | 2010-06-30 | 2017-01-25 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| CA2861804C (en) | 2011-12-27 | 2021-10-26 | Ironwood Pharmaceuticals, Inc. | 2-benzyl,3(pyrimidin-2-yl)substituted pyrazoles useful as sgc stimulators |
| EP2897953B8 (en) * | 2012-09-19 | 2019-06-26 | Cyclerion Therapeutics, Inc. | Sgc stimulators |
| PT2970243T (pt) * | 2013-03-15 | 2020-03-05 | Cyclerion Therapeutics Inc | Estimuladores de sgc |
| EP3092231B1 (en) * | 2013-12-11 | 2018-06-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| EP3194382B1 (en) * | 2014-09-17 | 2021-09-08 | Cyclerion Therapeutics, Inc. | Pyrazole derivatives as sgc stimulators |
| WO2016044445A2 (en) * | 2014-09-17 | 2016-03-24 | Ironwood Pharmaceuticals, Inc. | sGC STIMULATORS |
| WO2016044446A2 (en) * | 2014-09-17 | 2016-03-24 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| JP2017527605A (ja) * | 2014-09-17 | 2017-09-21 | アイアンウッド ファーマシューティカルズ インコーポレイテッド | ｓＧＣ刺激剤 |
| KR102841419B1 (ko) * | 2015-11-30 | 2025-08-01 | 사이클리온 테라퓨틱스, 인크. | sGC 자극제를 포함하는 고체 분산물 |
| CA3029375A1 (en) | 2016-07-07 | 2018-01-11 | Ironwood Pharmaceuticals, Inc. | Novel processes for preparation of soluble guanylate cyclase stimulators |
| WO2018009602A2 (en) | 2016-07-07 | 2018-01-11 | Ironwood Pharmaceuticals, Inc. | Novel processes for preparation of soluble guanylate cyclase stimulators |
| JP2019524710A (ja) * | 2016-07-07 | 2019-09-05 | アイアンウッド ファーマシューティカルズ インコーポレイテッド | Ｓｇｃ刺激剤の固体形態 |
| KR102745228B1 (ko) * | 2017-12-19 | 2024-12-19 | 사이클리온 테라퓨틱스, 인크. | sGC 자극제 |
| JP7357621B2 (ja) * | 2018-01-10 | 2023-10-06 | サイクレリオン・セラピューティクス，インコーポレーテッド | 可溶性グアニル酸シクラーゼ刺激剤を調製するための新規のプロセスおよび中間体 |
-
2017
- 2017-07-06 CA CA3029375A patent/CA3029375A1/en active Pending
- 2017-07-06 EA EA201990237A patent/EA201990237A1/ru unknown
- 2017-07-06 SG SG11201900096QA patent/SG11201900096QA/en unknown
- 2017-07-06 ES ES17745553T patent/ES2963563T3/es active Active
- 2017-07-06 US US16/315,218 patent/US11319308B2/en active Active
- 2017-07-06 KR KR1020197003459A patent/KR102487872B1/ko active Active
- 2017-07-06 CN CN201780047020.6A patent/CN109563077A/zh active Pending
- 2017-07-06 MA MA045603A patent/MA45603A/fr unknown
- 2017-07-06 AU AU2017291827A patent/AU2017291827B2/en active Active
- 2017-07-06 WO PCT/US2017/040810 patent/WO2018009597A1/en not_active Ceased
- 2017-07-06 EP EP23185002.5A patent/EP4249488A3/en active Pending
- 2017-07-06 MX MX2019000105A patent/MX389920B/es unknown
- 2017-07-06 BR BR112019000291A patent/BR112019000291A2/pt not_active Application Discontinuation
- 2017-07-06 EP EP17745553.2A patent/EP3481818B1/en active Active
- 2017-07-06 JP JP2019500355A patent/JP7112384B2/ja active Active
-
2018
- 2018-12-27 IL IL263995A patent/IL263995B/en active IP Right Grant
-
2019
- 2019-01-04 CL CL2019000016A patent/CL2019000016A1/es unknown
- 2019-01-07 MX MX2022001495A patent/MX2022001495A/es unknown
-
2022
- 2022-03-30 US US17/708,296 patent/US11773089B2/en active Active
-
2023
- 2023-01-24 CL CL2023000228A patent/CL2023000228A1/es unknown
- 2023-08-24 US US18/237,435 patent/US20240059684A1/en not_active Abandoned
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