HRP20240027T1 - Postupci za proizvodnju brivaracetama - Google Patents

Postupci za proizvodnju brivaracetama Download PDF

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HRP20240027T1
HRP20240027T1 HRP20240027TT HRP20240027T HRP20240027T1 HR P20240027 T1 HRP20240027 T1 HR P20240027T1 HR P20240027T T HRP20240027T T HR P20240027TT HR P20240027 T HRP20240027 T HR P20240027T HR P20240027 T1 HRP20240027 T1 HR P20240027T1
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compound
formula
alkyl
image
aryl
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HRP20240027TT
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Peng Wang
Pixu Li
Qiang Wei
Yuanhua Liu
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Suzhou Pengxu Pharmatech Co., Ltd.
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Priority claimed from CN201510271449.6A external-priority patent/CN106279074B/zh
Priority claimed from CN201510430387.9A external-priority patent/CN106365986B/zh
Priority claimed from CN201510648574.4A external-priority patent/CN106432030B/zh
Application filed by Suzhou Pengxu Pharmatech Co., Ltd. filed Critical Suzhou Pengxu Pharmatech Co., Ltd.
Publication of HRP20240027T1 publication Critical patent/HRP20240027T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
    • C07C209/08—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/38—Acyl halides
    • C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
    • C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/63—Halogen-containing esters of saturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C71/00—Esters of oxyacids of halogens

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrrole Compounds (AREA)

Claims (18)

1. Postupak za pripremu brivaracetama XII a) od VII [image] gdje je R1 zasićen ili nezasićen C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran; a X je Cl, Br, I, OMs, OTs, ONs; ili alternativno, b) iz spoja formule X, [image]
2. Postupak sukladno patentnom zahtjevu 1, naznačen time, da se spoj formule XIII pripravlja iz spoja formule IV, [image] gdje je R zasićen ili nezasićen C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran, pri čemu postupak uključuje korake dekarboksilacije spoja formule IV [image] za proizvodnju spoja formule VI [image] otvaranje prstena spoja formule VI da se dobije spoj formule VIII [image] gdje je R1 zasićen ili nezasićen C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran; a X je Cl, Br, I, OMs, OTs, ONs; ili spoj formule X [image] zatim pretvorbom VII ili X reakcijom s (S)-2-aminobutanamidom ili njegovom soli ili alkil (S)-2- aminobutanoatom da se dobije spoj formule XII.
3. Postupak sukladno patentnom zahtjevu 2, gdje se spoj formule IV prevodi u spoj formule VI kako slijedi: [image] a) spoj formule IV se prevodi u spoj formule VI u prisutnosti otapala i soli ili baze; i gdje je R C1-20 zasićeni ili nezasićeni alkil; ili b) spoj formule IV se prevodi u spoj formule V [image] koji se pak pretvara u spoj formule VI.
4. Postupak sukladno patentnom zahtjevu 2, naznačen time, da je postupak za pripravu VII iz VI [image] sastoji se od koraka a) prevođenje spoja formule VI u spoj formule VIII u prisutnosti otapala I TMSI, TMSBr, HBr, HCl ili HI; ili b) otvaranje prstena spoja formule VI i hidroliza pod bazičnim uvjetima u otapalu, nakon čega slijedi esterifikacijom i reakcijom sa sulfonil kloridom, pri čemu je sulfonil klorid odabran iz skupine koja se sastoji od MsCI, TsCI i NsCI, da se dobije spoj formule VII; gdje je R1 zasićen ili nezasićen C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran; i X je Cl, Br, I, OMs, OTs ili ONs.
5. Postupak sukladno patentnom zahtjevu 1, naznačen time što postupak za pripravu brivaracetama XII uključuje provođenje alternative a) iz VII [image] gdje je R1 zasićen ili nezasićen C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran; i X je Cl, Br, I, OMs, OTs, ONs.
6. Postupak sukladno patentnom zahtjevu 5 [image] pri čemu postupak uključuje reakciju spoja formule VII s (S)-2-aminobutanamidom ili njegovom soli ili alkilom (S)-2-aminobutanoat u otapalu pod bazičnim uvjetima za proizvodnju spoja formule IX ili IX-a, gdje R1 je zasićen ili nezasićen C1-20 alkil ili C1-20 alkil ili C1-20 alkil, gdje je aril nesupstituiran; i R2 je alkil.
7. Postupak za pripremu brivaracetama XII sukladno patentnom zahtjevu 6, naznačen time, da postupak dalje uključuje reakciju zatvaranja prstena [image] za proizvodnju brivaracetama XII; ili [image] za proizvodnju brivaracetama XII, gdje je R1 zasićen ili nezasićen C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran; i R2 je alkil.
8. Postupak sukladno patentnom zahtjevu 2, naznačen time, da postupak uključuje pripravu spoja formule X iz spoja formule VI [image]
9. Postupak sukladno patentnom zahtjevu 8, koji obuhvaća korak reakcije spoja VI sa SOCl2 i katalizatorom Lewisove kiseline da se dobije spoj formule X.
10. Postupak sukladno patentnom zahtjevu 1, naznačen time, da postupak dobivanja spoja formule XII (brivaracetama) uključuje provođenje alternative b) iz spoja formule X [image]
11. Postupak sukladno patentnom zahtjevu 10, naznačen time što obuhvaća korak reakcije spoja Formule X s alkil (S)-2-aminobutanoatom za proizvodnju spoja formule XII-a, nakon čega slijedi aminoliza ili hidroliza/formiranje amida za proizvodnju spoja formule XII (brivaracetam), gdje je R NH2, C1-C20 alkoksil; ako je R NH2, XIII-a je XII; ili [image] reakciju spoja formule X s (S)-2-aminobutanamidom ili njegovom soli da se dobije spoj formule XI; i prevođenje spoja formule XI u spoj XIII (brivaracetam); ili reakciju spoja formule X s alkil (S)-2-aminobutanoatom da se dobije spoj formule XI-a; i prevođenje spoja formule XI-a u spoj XII-a; zatim pretvarajući spoj od XII-a do XII [image] gdje je R NH2, C1-C20 alkoksil; ako je R NH2, tada je XI-a XI, a Xll-a je XII.
12. Postupak sukladno patentnom zahtjevu 2, za pripremu spoja formule XII (brivaracetam), koji uključuje korake od: [image]
13. Postupak sukladno patentnom zahtjevu 2, za pripremu spoja formule XII (brivaracetam), koji uključuje korake od: [image]
14. Spoj formule VII: [image] gdje je R1 H ili zasićeni ili nezasićeni C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran, a X je Cl, Br, I, OMs, OTs, ONs.
15. Spoj formule IX: [image] gdje je R1 zasićen ili nezasićen C1-20 alkil ili C1-alkil-aril gdje je aril nesupstituiran.
16. Spoj formule X [image]
17. Spoj formule XI-b: [image] gdje je R NH2 ili C1-C29 alkoksil; i X je Cl, Br, I, OMs, OTs, ONs.
18. Spoj sukladno patentnom zahtjevu 17, naznačen time, da R je NH2, a X je Cl [image]
HRP20240027TT 2015-05-25 2016-05-24 Postupci za proizvodnju brivaracetama HRP20240027T1 (hr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CN201510271449.6A CN106279074B (zh) 2015-05-25 2015-05-25 一种化合物及其制备方法和在合成布瓦西坦中的用途
CN201510430387.9A CN106365986B (zh) 2015-07-21 2015-07-21 化合物及其制备方法和在合成布瓦西坦中的用途
CN201510648574.4A CN106432030B (zh) 2015-10-10 2015-10-10 布瓦西坦的一种制备方法
CN201610099672 2016-02-24
PCT/US2016/033965 WO2016191435A1 (en) 2015-05-25 2016-05-24 Processes to produce brivaracetam
EP16800643.5A EP3302441B1 (en) 2015-05-25 2016-05-24 Processes to produce brivaracetam

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HRP20240027T1 true HRP20240027T1 (hr) 2024-04-26

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US (3) US10221134B2 (hr)
EP (1) EP3302441B1 (hr)
JP (1) JP6872500B2 (hr)
KR (1) KR102630456B1 (hr)
BR (1) BR112017025266A2 (hr)
CA (1) CA2984832A1 (hr)
ES (1) ES2965746T3 (hr)
HR (1) HRP20240027T1 (hr)
HU (1) HUE064612T2 (hr)
IL (1) IL255880B (hr)
MX (1) MX2017015133A (hr)
PL (1) PL3302441T3 (hr)
WO (1) WO2016191435A1 (hr)

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