ME02469B - Proces za pripremu jedinjenja koja su korisna kao inhibitori sglt2 - Google Patents
Proces za pripremu jedinjenja koja su korisna kao inhibitori sglt2Info
- Publication number
- ME02469B ME02469B MEP-2016-153A MEP2016153A ME02469B ME 02469 B ME02469 B ME 02469B ME P2016153 A MEP2016153 A ME P2016153A ME 02469 B ME02469 B ME 02469B
- Authority
- ME
- Montenegro
- Prior art keywords
- ring
- formula
- compound
- optionally substituted
- zinc salt
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 22
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000003751 zinc Chemical class 0.000 claims 12
- 238000000034 method Methods 0.000 claims 10
- 239000003153 chemical reaction reagent Substances 0.000 claims 8
- 125000001979 organolithium group Chemical group 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical group Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 229930195733 hydrocarbon Natural products 0.000 claims 4
- 150000002430 hydrocarbons Chemical class 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 3
- 150000001555 benzenes Chemical group 0.000 claims 3
- 229910052725 zinc Inorganic materials 0.000 claims 3
- 239000011701 zinc Substances 0.000 claims 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (11)
1. Proces za pripremu jedinjenja formule (I)pri čemu su Prsten A, i Prsten B jedan od sledećih:(1) Prsten A je opciono supstituisani nezasićeni monociklični heterociklični prsten, i Prsten B je opciono supstituisani nezasićeni monociklični heterociklični prsten, opciono supstituisani nezasićeni fuzionisani heterobiciklični prsten, ili opciono supstituisani benzenov prsten; ili(2) Prsten A je opciono supstituisani benzenov prsten, i Prsten B je opciono supstituisani nezasićeni monociklični heterociklični prsten, ili opciono supstituisani nezasićeni fuzionisani heterobiciklični prsten pri čemu je Y povezan na heterociklični prsten fuzionisanog heterobicikličnog prstena; ili(3) Prsten A je opciono supstituisani nezasićeni fuzionisani heterobiciklični prsten, pri čemu su šećerni ostatak X- (šećer) i ostatak-Y-(prsten B), oba na istom heterocikličnom prstenu fuzionisanog heterobicikličnog prstena, i Prsten B je opciono supstituisani nezasićeni monociklični heterociklični prsten, opciono supstituisani nezasićeni fuzionisani heterobiciklični prsten, ili opciono supstituisani benzenov prsten;X je atom ugljenika;Y je -(CH2)n-; pri čemu je n 1 ili 2;obezbedjujući da je u Prstenu A, X deo nezasićene veze;ili njegova farmaceutski prihvatljiva so ili solvat; obuhvatajućireagovanje jedinjenja formule (V) pri čemu je LG1 odlazća grupa, sa smešom cinkove soli i organolitijumovog reagensa; u prvom ugljovodoničnom rastvaraču; na temperaturi u rasponu od oko -78°C do oko sobne temperature; da se dobije smeša odgovarajućeg jedinjenja formule (VI), pri čemu je M1 litijum i cinkova so;mešanje u smešu jedinjenja formule (VI) i cinkove soli u prvom etarskom rastvaraču; da se dobije odgovarajuće jedinjenje formule (VII), pri čemu je M2 cink reaktivnih vrsta;reagovanje jedinjenja formule (VII), sa jedinjenjem formule (VIII), pri čemu svaka Z je nezavisno izabrana kiseonik zaštitna grupa i pri čemu je LG2 odlazeća grupa; da se dobije odgovarajuće jedinjenje formule (IX);uklanjanje zaštite jedinjenja formule (IX); da se dobije odgovarajuće jedinjenje formule (I).
2. Proces prema patentnom zahtevu 1 za pripremu jedinjenja formule (IS) ili njegove farmaceutski prihvatljive soli ili solvata; koji sadrži reagovanje jedinjenja formule (V-S) pri čemu je LG1 odlazća grupa, sa smešom cinkove soli i organolitijumovog reagensa; u prvom ugljovodoničnom rastvaraču; na temperaturi u rasponu od oko -78°C do oko sobne temperature; da se dobije smeša odgovarajućeg jedinjenja formule (VI-S), pri čemu je M1 litijum i cinkova so; mešanje u smešu jedinjenja formule (VI-S) i cinkove soli u prvom etarskom rastvaraču; da se dobije odgovarajuće jedinjenje formule (VII-S), pri čemu je M2 cink reaktivnih vrsta; reagovanje jedinjenja formule (VII-S), pri čemu je M2 vrste cinka, sa jedinjenjem formule (VIII-S), pri čemu je svaka Z nezavisno izabrana kiseonik zaštitna grupa i pri čemu je LG2 odlazeća grupa; da se dobije odgovarajuće jedinjenje formule (IX-S); uklanjanje zaštite jedinjenja formule (IX-S); da se dobije odgovarajuće jedinjenje formule (I-S).
3. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu je cinkova so ZnBr2 i pri čemu je organo-litijumov reagens n-butil litijum.
4. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu su cinkova so, i organo-litijumov reagens prisutni u molarnom odnosu od oko 1:2.
5. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu su cinkova so, i organo-litijumov reagens prethodno mešani tokom perioda od oko 1 do oko 2 sata.
6. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu je prvi ugljovodonični rastvarač toluen.
7. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu je LG1 jod, zinkova so je ZnBr2, organolitijumov reagens je n-butil litijum, cinkova so i organo-litijumov reagens su pretrhodno-pomešani, prvi ugljovodonični rastvarač je toluen, i pri čemu je jedinjenje formule (V) reagovalo sa smešom cinkove soli i organolitijumovim reagensom na temperaturi od oko 0°C.
8. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu je prvi etarski rastvarač din-butil etar.
9. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu je prvi etarski rastvarač prisutan u količini u rasponu od oko 7% do oko 10% po zapremini.
10. Proces prema patentnom zahtevu 1 ili patentnom zahtevu 2, pri čemu je LG1 jod, Z je pivaloil i LG2 je brom.
11. Proces prema patentnom zahtevu 1, pri čemu X je atom ugljenika; Prsten A je izabran iz grupe koja se sastoji od 4-metilfenila i 4-hlorofenila; Y je -CH2- i vezan je na 3-poziciji Prstena A; i Prsten B je izabran iz grupe koja ses sastoji od 2-(5-(4-fluorofenil)-tienila) i 2-(5-(6-fluoro-pirid-3-il)-tienila). Janssen Phamaceutica NV., BE 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161474936P | 2011-04-13 | 2011-04-13 | |
| EP12715362.5A EP2697218B1 (en) | 2011-04-13 | 2012-04-12 | Process for the preparation of compounds useful as inhibitors of sglt2 |
| PCT/EP2012/056649 WO2012140120A1 (en) | 2011-04-13 | 2012-04-12 | Process for the preparation of compounds useful as inhibitors of sglt2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02469B true ME02469B (me) | 2017-02-20 |
Family
ID=45976924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-153A ME02469B (me) | 2011-04-13 | 2012-04-12 | Proces za pripremu jedinjenja koja su korisna kao inhibitori sglt2 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US10544135B2 (me) |
| EP (1) | EP2697218B1 (me) |
| JP (1) | JP5973551B2 (me) |
| KR (1) | KR101913587B1 (me) |
| CN (1) | CN103596944B (me) |
| AU (1) | AU2012241897C1 (me) |
| CA (1) | CA2832938C (me) |
| CY (1) | CY1117989T1 (me) |
| DK (1) | DK2697218T3 (me) |
| EA (1) | EA028946B1 (me) |
| ES (1) | ES2586846T3 (me) |
| HR (1) | HRP20161062T1 (me) |
| HU (1) | HUE030116T2 (me) |
| ME (1) | ME02469B (me) |
| PL (1) | PL2697218T3 (me) |
| PT (1) | PT2697218T (me) |
| RS (1) | RS55056B1 (me) |
| SI (1) | SI2697218T1 (me) |
| SM (1) | SMT201600274B (me) |
| WO (1) | WO2012140120A1 (me) |
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| WO2014132940A1 (ja) | 2013-02-26 | 2014-09-04 | 田辺三菱製薬株式会社 | α－ハロテトラアシルグルコースの製造方法 |
| CN104557894A (zh) * | 2013-10-18 | 2015-04-29 | 上海信谊药厂有限公司 | 坎格列汀晶型及其制备方法 |
| CN104672227A (zh) * | 2013-11-28 | 2015-06-03 | 镇江新元素医药科技有限公司 | 一类新型sglt2抑制剂化合物及其药物组合物 |
| EP2918579A1 (en) * | 2014-03-14 | 2015-09-16 | LEK Pharmaceuticals d.d. | Synthesis of 2-arylmethyl-5-aryl-thiophene |
| CN103980262B (zh) * | 2014-04-01 | 2016-06-22 | 天津大学 | 卡格列净的b晶型及其结晶制备方法 |
| CN103980261B (zh) * | 2014-04-01 | 2016-06-29 | 天津大学 | 卡格列净的a晶型及其结晶制备方法 |
| CN103936725B (zh) * | 2014-04-01 | 2016-07-27 | 天津大学 | 卡格列净的c晶型及其结晶制备方法 |
| EP2933255A1 (en) | 2014-04-17 | 2015-10-21 | LEK Pharmaceuticals d.d. | Novel crystalline form of 1-(beta-D-glucopyranosyl)-4- methyl-3-[5-(4-fluorophenyl)-2-thienylmethyl]benzene |
| CN103980263B (zh) * | 2014-04-17 | 2016-08-03 | 海门瑞一医药科技有限公司 | 卡格列净的合成工艺 |
| EP2947077A1 (en) | 2014-05-19 | 2015-11-25 | LEK Pharmaceuticals d.d. | Stereoselective synthesis of intermediates in the preparation of ß-C-arylglucosides |
| CN104109157B (zh) * | 2014-08-04 | 2016-05-25 | 山东康美乐医药科技有限公司 | 卡格列净的制备方法 |
| CN105440025B (zh) * | 2014-09-25 | 2019-02-12 | 深圳翰宇药业股份有限公司 | 一种制备卡格列净及其中间体的方法及所述中间体 |
| CN104817554A (zh) * | 2014-11-10 | 2015-08-05 | 镇江新元素医药科技有限公司 | 一类葡萄糖苷衍生物及其药物组合物 |
| CN104557895B (zh) * | 2015-01-27 | 2017-10-31 | 江苏嘉逸医药有限公司 | 1‑(β‑D‑吡喃葡糖基)‑4‑甲基‑3‑[5‑(4‑氟苯基)‑2‑噻吩基甲基]苯的合成工艺 |
| CN105884755B (zh) * | 2015-02-14 | 2019-05-28 | 正大天晴药业集团股份有限公司 | 氘修饰的碳甙衍生物 |
| CN106188022A (zh) * | 2015-04-30 | 2016-12-07 | 上海医药工业研究院 | 伊格列净的制备方法 |
| CN105153137A (zh) * | 2015-09-17 | 2015-12-16 | 上海应用技术学院 | 一种艾格列净的制备方法 |
| CN105503845A (zh) * | 2015-12-01 | 2016-04-20 | 北京普德康利医药科技发展有限公司 | 去氟卡格列净化合物及其制备方法和应用 |
| CN109988128B (zh) * | 2017-12-29 | 2022-08-19 | 江苏扬农化工股份有限公司 | 一种呋喃醇衍生物的合成方法 |
| CN110054657B (zh) * | 2018-01-18 | 2021-06-29 | 亚宝药业集团股份有限公司 | 吡喃葡萄糖取代的吡唑化合物及其制备方法 |
| CN109111490B (zh) * | 2018-08-09 | 2021-02-23 | 浙江大学 | 卤代新戊酰基吡喃葡萄糖及其用于sglt2抑制剂的制备方法 |
| CN114591313A (zh) * | 2020-12-04 | 2022-06-07 | 南京圣鼎医药科技有限公司 | 一种卡格列净的制备方法 |
| JP2024541058A (ja) * | 2021-11-03 | 2024-11-06 | ハンジョウ ディーエーシー バイオテック シーオー．，エルティディ． | 抗体の特異的共役 |
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- 2012-04-12 HU HUE12715362A patent/HUE030116T2/en unknown
- 2012-04-12 RS RS20160668A patent/RS55056B1/sr unknown
- 2012-04-12 CN CN201280029303.5A patent/CN103596944B/zh active Active
- 2012-04-12 PT PT127153625T patent/PT2697218T/pt unknown
- 2012-04-12 HR HRP20161062TT patent/HRP20161062T1/hr unknown
- 2012-04-12 ME MEP-2016-153A patent/ME02469B/me unknown
-
2016
- 2016-08-11 SM SM201600274T patent/SMT201600274B/it unknown
- 2016-08-18 CY CY20161100815T patent/CY1117989T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI2697218T1 (sl) | 2016-07-29 |
| EA201391522A1 (ru) | 2014-03-31 |
| JP2014510776A (ja) | 2014-05-01 |
| KR101913587B1 (ko) | 2018-10-31 |
| EP2697218A1 (en) | 2014-02-19 |
| DK2697218T3 (en) | 2016-07-25 |
| SMT201600274B (it) | 2016-08-31 |
| US10544135B2 (en) | 2020-01-28 |
| CN103596944A (zh) | 2014-02-19 |
| AU2012241897A1 (en) | 2013-10-24 |
| HUE030116T2 (en) | 2017-04-28 |
| HRP20161062T1 (hr) | 2016-12-16 |
| CY1117989T1 (el) | 2017-05-17 |
| EP2697218B1 (en) | 2016-05-25 |
| AU2012241897B2 (en) | 2016-12-01 |
| KR20140026467A (ko) | 2014-03-05 |
| CN103596944B (zh) | 2017-02-22 |
| AU2012241897C1 (en) | 2017-05-11 |
| US20190194177A1 (en) | 2019-06-27 |
| PT2697218T (pt) | 2016-07-13 |
| ES2586846T3 (es) | 2016-10-19 |
| EA028946B1 (ru) | 2018-01-31 |
| RS55056B1 (sr) | 2016-12-30 |
| JP5973551B2 (ja) | 2016-08-23 |
| CA2832938C (en) | 2019-09-03 |
| PL2697218T3 (pl) | 2016-11-30 |
| WO2012140120A1 (en) | 2012-10-18 |
| CA2832938A1 (en) | 2012-10-18 |
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