HRP20171899T1 - N-acilsulfonamidni promotori apoptoze - Google Patents

N-acilsulfonamidni promotori apoptoze Download PDF

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HRP20171899T1
HRP20171899T1 HRP20171899TT HRP20171899T HRP20171899T1 HR P20171899 T1 HRP20171899 T1 HR P20171899T1 HR P20171899T T HRP20171899T T HR P20171899TT HR P20171899 T HRP20171899 T HR P20171899T HR P20171899 T1 HRP20171899 T1 HR P20171899T1
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compound
formula
pharmaceutically acceptable
acceptable salt
methyl
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HRP20171899TT
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Robert Bruce Diebold
Thomas Gero
Paul Grover
Shan Huang
Stephanos Ioannidis
Claude Afona Ogoe
Jamal Carlos Saeh
Jeffrey Gilbert Varnes
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Astrazeneca Ab
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Publication of HRP20171899T1 publication Critical patent/HRP20171899T1/hr

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    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
    • 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Claims (16)

1. Spoj s Formulom (I) [image] ili njegova farmaceutski prihvatljiva sol, naznačen time da, R1 je -OH; R2 je -S(O)2CF3; R3 je C1-2alkil, pri čemu je navedeni C1-2alkil proizvoljno supstituiran s jednim ili više R40; R4 je C1-2alkil, pri čemu je navedeni C1-2alkil proizvoljno supstituiran s jednim ili više R40; R40 je kod svake pojave odabran od -OR40a i -OP(=O)(OH)2; i R40a je H.
2. Spoj prema zahtjevu 1, ili njegova farmaceutski prihvatljiva sol, naznačen time da spoj ima slijedeću stereokemiju: [image]
3. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, kako je zatraženo u zahtjevu 2, naznačen time da spoj je 4-(4-((R)-(4'-klorobifenil-2-il)(hidroksi)metil)piperidin-1-il)-N-(4-((R)-4-((2-hidroksietil)(metil)amino)-1-(feniltio)butan-2-ilamino)-3-(trifluorometilsulfonil)fenilsulfonil)benzamid.
4. Spoj s Formulom (I) kako je zatraženo u zahtjevu 2, naznačen time da spoj je 4-(4-((R)-(4'-klorobifenil-2-il)(hidroksi)metil)piperidin-1-il)-N-(4-((R)-4-((2-hidroksietil)(metil)amino)-1-(feniltio)butan-2-ilamino)-3-(trifluorometilsulfonil)fenilsulfonil)benzamid.
5. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, kako je zatraženo u zahtjevu 2, naznačen time da spoj je 2-(((R)-3-(4-(N-(4-(4-((R)-(4'-klorobifenil-2-il)(hidroksi)metil)piperidin-1-il)benzoil)sulfamoil)-2-(trifluorometilsulfonil)fenilamino)-4-(feniltio)butil)(metil)amino)etil dihidrogen fosfat.
6. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, kako je zatraženo u zahtjevu 2, naznačen time da spoj je 4-(4-((R)-(4'-klorobifenil-2-il)(hidroksi)metil)piperidin-1-il)-N-(4-((R)-4-(etil(2-hidroksietil)amino)-1-(feniltio)butan-2-ilamino)-3-(trifluorometilsulfonil)fenilsulfonil)benzamid.
7. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, kako je zatraženo u zahtjevu 2, naznačen time da spoj je 2-(((R)-3-(4-(N-(4-(4-((R)-(4'-klorobifenil-2-il)(hidroksi)metil)piperidin-1-il)benzoil)sulfamoil)-2-(trifluorometilsulfonil)fenilamino)-4-(feniltio)butil)(etil)amino)etil dihidrogen fosfat.
8. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva 1 do 7, naznačen time da je uporabu kao lijek.
9. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva 1 do 7, naznačen time da je uporabu za dobivanje anti-proliferacijskog i/ili pro-apoptotičkog djelovanja.
10. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva 1 do 7, naznačen time da je uporabu za liječenje raka kod toplokrvne životinje kao što je čovjek.
11. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva 1 do 7 naznačen time da je za upotrebu za liječenje raka mokraćnog mjehura, raka dojke, raka debelog crijeva, raka jajnika, AML, difuznog limfoma velikih B-stanica (DLBCL), CLL; karcinoma pluća malih stanica (SCLC), karcinoma pluća ne-malih stanica (NSCLC), uključujući ne-skvamozne i skvamozne podtipove, karcinom gušterače, karcinom prostate, ne-Hodgkinove limfome, folikularni limfom (FL), limfom plaštenih stanica (MCL), limfom plaštene zone (MZL), leukemija vlasastih stanica (HCL), te limfom perifernih T-stanica (PTCL).
12. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva 1 do 7 naznačen time da je za upotrebu u liječenju difuznog limfoma velikih B-stanica (DLBCL).
13. Spoj s Formulom (I), ili njegova farmaceutski prihvatljiva sol, prema bilo kojem od zahtjeva 1 do 7 naznačen time da je za upotrebu u liječenju karcinoma pluća ne-malih stanica (NSCLC).
14. Farmaceutski pripravak naznačen time da sadrži spoj s Formulom (I), ili njegovu farmaceutski prihvatljivu sol, prema bilo kojem od zahtjeva 1 do 7, te barem jedan farmaceutski prihvatljiv nosač, otapalo, ili pomoćno sredstvo.
15. Postupak za pripremanje spoja s Formulom (I), ili njegove farmaceutski prihvatljive soli, prema bilo kojem od zahtjeva 1 do 7, naznačen time da navedeni postupak obuhvaća: (i) osiguravanje spoja karboksilne kiseline s formulom (1-f): [image] (ii) osiguravanje sulfonamidnog spoja s formulom (1-g): [image] i (iii) sprezanje spoja karboksilne kiseline s formulom (1-f) sa sulfonamidnim spojem s formulom (1-g).
16. Postupak za pripremanje spoja s Formulom (2-g) i (2-h), naznačen time da navedeni postupak obuhvaća: [image] provođenje enantioselektivne redukcije u spoj s Formulom (3-c).
HRP20171899TT 2010-08-06 2017-12-07 N-acilsulfonamidni promotori apoptoze HRP20171899T1 (hr)

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US37164810P 2010-08-06 2010-08-06
US38417010P 2010-09-17 2010-09-17
EP11746295.2A EP2601177B1 (en) 2010-08-06 2011-08-05 N-acylsulfonamide apoptosis promoters
PCT/GB2011/051484 WO2012017251A1 (en) 2010-08-06 2011-08-05 N-acylsulfonamide apoptosis promoters

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