WO2018171698A1 - Dérivés d'un hétéroaryle et d'une pyrimidinone, leur procédé de préparation et leur application - Google Patents
Dérivés d'un hétéroaryle et d'une pyrimidinone, leur procédé de préparation et leur application Download PDFInfo
- Publication number
- WO2018171698A1 WO2018171698A1 PCT/CN2018/080117 CN2018080117W WO2018171698A1 WO 2018171698 A1 WO2018171698 A1 WO 2018171698A1 CN 2018080117 W CN2018080117 W CN 2018080117W WO 2018171698 A1 WO2018171698 A1 WO 2018171698A1
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- WIPO (PCT)
- Prior art keywords
- group
- heteroaryl
- cycloalkyl
- aryl
- alkyl
- Prior art date
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 150000001602 bicycloalkyls Chemical group 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
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- 239000012267 brine Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
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- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 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 description 1
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- XIQUJVRFXPBMHS-UHFFFAOYSA-N hydron;o-prop-2-enylhydroxylamine;chloride Chemical compound Cl.NOCC=C XIQUJVRFXPBMHS-UHFFFAOYSA-N 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 1
- WOXGREIMSJFDPG-UHFFFAOYSA-N o-(2-methylpropyl)hydroxylamine;hydrochloride Chemical compound Cl.CC(C)CON WOXGREIMSJFDPG-UHFFFAOYSA-N 0.000 description 1
- HMMFZNBOQJOULD-UHFFFAOYSA-N o-(cyclopropylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1CC1 HMMFZNBOQJOULD-UHFFFAOYSA-N 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
- FOFBPRRSRZLRBW-UHFFFAOYSA-N o-propan-2-ylhydroxylamine;hydrochloride Chemical compound Cl.CC(C)ON FOFBPRRSRZLRBW-UHFFFAOYSA-N 0.000 description 1
- ZBDXGNXNXXPKJI-UHFFFAOYSA-N o-tert-butylhydroxylamine;hydrochloride Chemical compound Cl.CC(C)(C)ON ZBDXGNXNXXPKJI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000031390 regulation of fatty acid biosynthetic process Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004808 supercritical fluid chromatography Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- NFBQJHOKTSYEDJ-QHCPKHFHSA-N tert-butyl 2-[1-[(2R)-2-(2-methoxyphenyl)-2-(oxan-4-yloxy)ethyl]-5-methyl-6-(1,3-oxazol-2-yl)-2,4-dioxothieno[2,3-d]pyrimidin-3-yl]-2-methylpropanoate Chemical compound COC1=C(C=CC=C1)[C@H](CN1C2=C(C(C)=C(S2)C2=NC=CO2)C(=O)N(C1=O)C(C)(C)C(=O)OC(C)(C)C)OC1CCOCC1 NFBQJHOKTSYEDJ-QHCPKHFHSA-N 0.000 description 1
- WVXXNJXIWBKQKQ-NRFANRHFSA-N tert-butyl 2-[6-bromo-1-[(2R)-2-(2-methoxyphenyl)-2-(oxan-4-yloxy)ethyl]-5-methyl-2,4-dioxothieno[2,3-d]pyrimidin-3-yl]-2-methylpropanoate Chemical compound O(C1=C([C@H](CN2C(=O)N(C(=O)C3=C2SC(=C3C)Br)C(C)(C)C(=O)OC(C)(C)C)OC2CCOCC2)C=CC=C1)C WVXXNJXIWBKQKQ-NRFANRHFSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Definitions
- R a is selected from a hydrogen atom or an alkyl group
- R 4 and R 5 are each independently selected from a hydrogen atom, an alkyl group, -OR 11 , -SR 11 , -NR 9 R 10 , -C(O)NR 9 R 10 , -C(O)R 11 , -OC (O) R 11 , -S(O) n NR 9 R 10 , -C(O)OR 11 or -NR 9 C(O)R 10 ;
- R 6 is selected from the group consisting of halogen, cycloalkyl, heterocyclic, aryl, heteroaryl, -NR 9 R 10 , -C(O)NR 9 R 10 , -C(O)R 11 , -OC(O) R 11 , -S(O) n NR 9 R 10 , -C(O)OR 11 or -NR 9 C(O)R 10 , preferably a heteroaryl group;
- R 1 and R 6 together with the atom to which they are attached form a 3 to 8 membered saturated or partially unsaturated cycloalkyl group, or form a hetero atom having one or more selected from N, O, S(O) n .
- cycloalkyl group, heterocyclic group, aryl group or heteroaryl group is optionally further subjected to one or A plurality selected from the group consisting of hydroxyl, halogen, nitro, cyano, alkyl, alkoxy, cycloalkyl, heterocyclyl, aryl, heteroaryl, -NR 9 R 10 , -C(O)NR 9 R 10, -C (O) R 11 , -OC (O) R 11, -S (O) n NR 9 R 10, -C (O) oR 11 or -NR 9 C (O) R 10 substituents Replace
- n 0, 1, or 2.
- the invention also provides the use of a compound of formula (I) or a pharmaceutical composition thereof for the manufacture of a medicament for the treatment or prevention of a disease or condition associated with ACC, wherein the disease or condition is preferably a metabolic disease, a cancer, a fungus a parasitic or bacterial infection; wherein the metabolic disease is preferably hepatic steatosis, nonalcoholic fatty liver, obesity, dyslipidemia, hyperlipidemia, type II diabetes or metabolic syndrome, wherein the obesity is preferred Is Prader-Willi syndrome, Bardet-Biedl syndrome or Cohen syndrome or MOMO syndrome, wherein the cancer is preferably liver Cell carcinoma, non-small cell lung cancer, small cell lung cancer, gastric cancer, colorectal cancer, head and neck cancer, melanoma, ovarian cancer or cervical cancer, more preferably hepatocellular carcinoma and non-small cell lung cancer.
- the disease or condition is preferably a metabolic disease, a cancer, a fungus a parasitic or bacterial infection
- Examples of monocyclic cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentenyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptatriene
- the alkenyl group, the cyclooctyl group and the like are preferably a cyclopropyl group or a cyclohexenyl group.
- the spirocycloalkyl group is classified into a monospiro, a spiro- or a spirocycloalkyl group, preferably a mono- and bi-spirocycloalkyl group, preferably 4 yuan/5 yuan, 4, depending on the number of common spiro atoms between the rings. Yuan / 6 yuan, 5 yuan / 5 yuan or 5 yuan / 6 yuan.
- the heterocyclyl ring may be fused to an aryl, heteroaryl or cycloalkyl ring wherein the ring to which the parent structure is attached is a heterocyclic group.
- the heterocyclic group may be optionally substituted or unsubstituted.
- Heteroaryl means an aromatic 5 to 6 membered monocyclic or 9 to 10 membered bicyclic ring which may contain from 1 to 4 atoms selected from nitrogen, oxygen and/or sulfur.
- heteroaryl include, but are not limited to, furyl, pyridyl, 2-oxo-1,2-dihydropyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, isoxazolyl , oxazolyl, oxadiazolyl, imidazolyl, pyrrolyl, pyrazolyl, triazolyl, tetrazolyl, thiazolyl, isothiazolyl, 1,2,3-thiadiazolyl, benzo Dioxolyl, benzimidazolyl, fluorenyl, isodecyl, 1,3-dioxo-isoindenyl, quinolyl, ox
- Amino means -NH 2 .
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Font l'objet de la présente invention des dérivés d'un hétéroaryle et d'une pyrimidinone de formule I, leur procédé de préparation et leur application thérapeutique, particulièrement leur application comme inhibiteurs de l'acétyl coenzyme A carboxylase (ACCase), la définition de chaque substituant de formule I étant semblable à celle contenue dans la description.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201880018956.0A CN110431143B (zh) | 2017-03-24 | 2018-03-23 | 杂芳基并嘧啶酮类衍生物及其制备方法和用途 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710182530.6 | 2017-03-24 | ||
| CN201710182530 | 2017-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2018171698A1 true WO2018171698A1 (fr) | 2018-09-27 |
Family
ID=63584121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2018/080117 WO2018171698A1 (fr) | 2017-03-24 | 2018-03-23 | Dérivés d'un hétéroaryle et d'une pyrimidinone, leur procédé de préparation et leur application |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN110431143B (fr) |
| WO (1) | WO2018171698A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10759812B2 (en) | 2017-01-22 | 2020-09-01 | Sunshine Lake Pharma Co., Ltd. | Thienopyrimidine derivative and use thereof in medicine |
| WO2021000242A1 (fr) * | 2019-07-02 | 2021-01-07 | 广东东阳光药业有限公司 | Dérivés de thiénopyrimidine ayant des configurations stéréo et leur utilisation en médecine |
| CN112739705A (zh) * | 2018-11-20 | 2021-04-30 | 中国医药研究开发中心有限公司 | 螺环类化合物及其医药用途 |
| WO2022138812A1 (fr) | 2020-12-24 | 2022-06-30 | モジュラス株式会社 | Composé de tétrahydrothiénopyridinesulfonamide |
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| WO2013071169A1 (fr) * | 2011-11-11 | 2013-05-16 | Nimbus Apollo, Inc. | Inhibiteurs de l'acc et utilisations associées |
| WO2014182945A1 (fr) * | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Inhibiteurs de l'acc et leurs utilisations |
| WO2014182950A1 (fr) * | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Inhibiteurs de l'acc et utilisations associées |
| WO2014182943A1 (fr) * | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Inhibiteurs de l'acc et utilisations associées |
| WO2017091600A1 (fr) * | 2015-11-25 | 2017-06-01 | Gilead Apollo, Llc | Inhibiteurs de l'acc à base de pyrazole et utilisations associées |
| WO2017091617A1 (fr) * | 2015-11-25 | 2017-06-01 | Gilead Apollo, Llc | Inhibiteurs d'acc à base de triazole et utilisations associées |
| WO2017091602A1 (fr) * | 2015-11-25 | 2017-06-01 | Gilead Apollo, Llc | Inhibiteurs de l'acc à base d'esters et utilisations associées |
-
2018
- 2018-03-23 WO PCT/CN2018/080117 patent/WO2018171698A1/fr active Application Filing
- 2018-03-23 CN CN201880018956.0A patent/CN110431143B/zh active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US10759812B2 (en) | 2017-01-22 | 2020-09-01 | Sunshine Lake Pharma Co., Ltd. | Thienopyrimidine derivative and use thereof in medicine |
| CN112739705A (zh) * | 2018-11-20 | 2021-04-30 | 中国医药研究开发中心有限公司 | 螺环类化合物及其医药用途 |
| CN112739705B (zh) * | 2018-11-20 | 2022-08-16 | 中国医药研究开发中心有限公司 | 螺环类化合物及其医药用途 |
| WO2021000242A1 (fr) * | 2019-07-02 | 2021-01-07 | 广东东阳光药业有限公司 | Dérivés de thiénopyrimidine ayant des configurations stéréo et leur utilisation en médecine |
| JP2022540560A (ja) * | 2019-07-02 | 2022-09-16 | ▲広▼▲東▼▲東▼▲陽▼光▲薬▼▲業▼有限公司 | 立体配置を有するチエノピリミジン誘導体及び薬物におけるその応用 |
| JP7374233B2 (ja) | 2019-07-02 | 2023-11-06 | ▲広▼▲東▼▲東▼▲陽▼光▲薬▼▲業▼有限公司 | 立体配置を有するチエノピリミジン誘導体及び薬物におけるその応用 |
| WO2022138812A1 (fr) | 2020-12-24 | 2022-06-30 | モジュラス株式会社 | Composé de tétrahydrothiénopyridinesulfonamide |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110431143B (zh) | 2022-08-12 |
| CN110431143A (zh) | 2019-11-08 |
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