HRP20191943T1 - Postupci za proizvodnju spojeva (ciklopentil[d]pirimidin-4-il)piperazina - Google Patents

Postupci za proizvodnju spojeva (ciklopentil[d]pirimidin-4-il)piperazina Download PDF

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HRP20191943T1
HRP20191943T1 HRP20191943TT HRP20191943T HRP20191943T1 HR P20191943 T1 HRP20191943 T1 HR P20191943T1 HR P20191943T T HRP20191943T T HR P20191943TT HR P20191943 T HRP20191943 T HR P20191943T HR P20191943 T1 HRP20191943 T1 HR P20191943T1
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compound
formula
salt
salts
protecting group
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HRP20191943TT
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Francis Gosselin
Chong Han
Hans Iding
Reinhard Reents
Scott Savage
Beat Wirz
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F. Hoffmann - La Roche Ag
Genentech, Inc.
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Publication of HRP20191943T1 publication Critical patent/HRP20191943T1/hr

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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
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    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
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    • C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
    • C07C255/22—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton containing cyano groups and at least two carboxyl groups bound to the carbon skeleton
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C12N9/14—Hydrolases (3)
    • C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
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Claims (15)

1. Postupak za proizvodnju spoja formule I: ili njegove soli, naznačen time, da postupak obuhvaća dovođenje u doticaj spoja formule III: ili njegove soli, s metalizacijskim sredstvom u svrhu tvorbe spoja formule I, ili njegove soli; pri čemu R1 je vodik ili amino zaštitna skupina.
2. Postupak prema patentnom zahtjevu 1, naznačen time, da se spoj formule III, ili njegova sol, proizvodi dovođenjem u doticaj spoja formule IV: ili njegove soli, gdje Y je brom ili klor, sa spojem piperazina koji ima sljedeću strukturu: ili s njegovom soli, pri čemu je Lv izlazna skupina i R1 je amino zaštitna skupina.
3. Postupak prema patentnom zahtjevu 2, naznačen time, da Y je brom.
4. Postupak prema patentnom zahtjevu 2 ili zahtjevu 3, naznačen time, da je Lv odabrana od vodika i halogena, a R1 je odabrana od sljedećih: acetil, trifluoroacetil, ftalimidil, benzil, trifenilmetil, benzilidenil, p-toluensulfonil, p-metoksibenzil, tertbutiloksikarbonil, 9-fluorenilmetiloksikarbonil i karbobenziloksi.
5. Postupak prema bilo kojem od patentnih zahtjeva 2 do 4, naznačen time, da se spoj formule IV, ili njegova sol, dovodi u doticaj s oko jednim molarnim ekvivalentom do oko 1,5 molarnih ekvivalenata spoja piperazina.
6. Postupak prema bilo kojem od patentnih zahtjeva 2 do 5, naznačen time, da se spoj formule IV, ili njegova sol, dovodi u doticaj sa spojem piperazina na sobnoj temperaturi.
7. Postupak prema bilo kojem od patentnih zahtjeva 2 do 6, naznačen time, da se spoj formule IV, ili njegova sol, proizvodi pomoću brominacije spoja formule V: ili njegove soli, gdje je svaki X neovisno odabran od klora i hidroksila.
8. Postupak prema patentnom zahtjevu 7, naznačen time, da je svaki X klor ili alternativno svaki X je hidroksil.
9. Postupak prema bilo kojem od patentnih zahtjeva 2 do 6, naznačen time, da se spoj ili sol formule IV proizvodi putem sljedećih koraka: (i) klorinacija spoja formule Vb: ili njegove soli, u svrhu tvorbe spoja formule Vc: ili njegove soli; i (ii) brominacija spoja ili soli formule Vc u svrhu tvorbe spoja formule IV, ili njegove soli.
10. Postupak prema patentnom zahtjevu 9, naznačen time, da se spoj ili sol formule Vbproizvodi ciklizacijom spoja formule VIb: ili njegove soli.
11. Postupak prema patentnom zahtjevu 10, naznačen time, da se spoj formule IVb ili njegova sol, proizvodi putem sljedećih koraka: (i) dovođenje u doticaj krotononitrila s malonatom u svrhu tvorbe izomerne mješavine koja sadrži spoj formule VIa: ili njegovu sol, i spoj formule VIb, ili njegovu sol; i (ii) razdvajanje spoja formule VIb, ili njegove soli, od spoja formule VIa, ili njegove soli.
12. Postupak prema bilo kojem od patentnih zahtjeva 1 do 11, naznačen time, da (a) R1 je amino zaštitna skupina ili (b) R1 je amino zaštitna skupina koja je odabrana od acetila, trifluoroacetila, ftalimidila, benzila, trifenilmetila, benzilidenila, p-toluensulfonila, p-metoksibenzila, tertbutiloksikarbonila, 9-fluorenilmetiloksikarbonila i karbobenziloksi.
13. Postupak prema bilo kojem od patentnih zahtjeva 1 do 12, naznačen time, da (a) metalizacijsko sredstvo je organometalni spoj ili (b) metalizacijsko sredstvo je organometalni spoj koji je odabran od sljedećih: izopropilmagnezijev klorid, kompleks izopropilmagnezijevog klorida i litijevog klorida, sek-butilmagnezijev klorid, n-butillitij, sek-butillitij, t-butillitij, litijev tri-n-butilmagnezijat, litijev triizopropilmagnezijat, i litijev (izopropil)(di-n-butil)magnezijat.
14. Postupak za proizvodnju spoja formule IX: ili njegove soli, naznačen time, da R2 je vodik ili amino zaštitna skupina, pri čemu postupak obuhvaća sljedeće korake: (i) dovođenje u doticaj spoja formule III: ili njegove soli, pri čemu R1 je vodik ili amino zaštitna skupina, s metalizacijskim sredstvom u svrhu tvorbe spoja formule I: ili njegove soli; (ii) reduciranje spoja formule I, ili njegove soli, u svrhu tvorbe spoja formule VIIa: ili njegove soli; (iii) prema potrebi uklanjanje zaštite spoja formule VIIa, ili njegove soli, u svrhu tvorbe spoja formule VIIb: ili njegove soli; i (iv) dovođenje u doticaj spoja formule VIIb, ili njegove soli, sa spojem formule VIII: ili s njegovom soli, u svrhu tvorbe spoja formule IX, ili njegove soli.
15. Spoj, naznačen time, da je predstavljen sljedećim formulama Vb, Vc, IVb, IVc ili III:
ili njegova sol, pri čemu R1 je vodik ili amino zaštitna skupina.
HRP20191943TT 2014-09-26 2019-10-24 Postupci za proizvodnju spojeva (ciklopentil[d]pirimidin-4-il)piperazina HRP20191943T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201462055893P 2014-09-26 2014-09-26
PCT/US2015/052143 WO2016049414A1 (en) 2014-09-26 2015-09-25 PROCESSES FOR PREPARING (CYCLOPENTYL[d]PYRIMIDIN-4-YL)PIPERAZINE COMPOUNDS
EP15782120.8A EP3197875B1 (en) 2014-09-26 2015-09-25 Processes for preparing (cyclopentyl[d]pyrimidin-4-yl)piperazine compounds

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CN107001287B (zh) * 2014-09-26 2020-09-04 豪夫迈·罗氏有限公司 用于制备(环戊并[d]嘧啶-4-基)哌嗪化合物的方法
EP4165026A1 (en) 2020-06-16 2023-04-19 F. Hoffmann-La Roche AG Process for making hydroxylated cyclopentylpyrimidine compounds
CN112359078A (zh) * 2021-01-12 2021-02-12 凯莱英生命科学技术(天津)有限公司 异丁酸酯类化合物的手性拆分方法

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