HRP20130215T1 - Hidrobenzoatne soli spojeva metanikotina - Google Patents

Hidrobenzoatne soli spojeva metanikotina Download PDF

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Publication number
HRP20130215T1
HRP20130215T1 HRP20130215TT HRP20130215T HRP20130215T1 HR P20130215 T1 HRP20130215 T1 HR P20130215T1 HR P20130215T T HRP20130215T T HR P20130215TT HR P20130215 T HRP20130215 T HR P20130215T HR P20130215 T1 HRP20130215 T1 HR P20130215T1
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Croatia
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compound
amine
treatment
hydroxybenzoate
cns disorders
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HRP20130215TT
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English (en)
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Julio A. Munoz
John Genus
James R. Moore
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Targacept, Inc.
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Publication of HRP20130215T1 publication Critical patent/HRP20130215T1/hr

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
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    • 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
    • A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
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    • A61P25/34—Tobacco-abuse
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    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Claims (7)

1. Spoj p-hidroksibenzoat (2S)-(4E)-N-metil-5-(5-izopropoksi-3-piridinil)-4-penten-2-amina.
2. Farmaceutski sastav koji sadrži spoj prema zahtjevu 1 i farmaceutski prihvatljiv nosač.
3. Spoj prema zahtjevu 1 za primjenu u liječenju CNS poremećaja.
4. Upotreba spoja prema zahtjevu 1 u proizvodnji lijeka za liječenje CNS poremećaja.
5. Farmaceutski sastav prema zahtjevu 2 za primjenu u liječenju CNS poremećaja.
6. Upotreba farmaceutskog sastava prema zahtjevu 2 u proizvodnji lijeka za liječenje CNS poremećaja.
7. Postupak za dobijanje p-hidroksibenzaota (2S)-(4E)-N-metil-5-(5-izopropoksi-3-piridinil)-4-penten-2-amina, koji obuhvaća korake: a) izvođenja Heckove reakcije spajanja između 3-halo-5-izopropoksipiridina i spoja formule (S)-CH2=CH-CH2-CH(CH3)-N(CH3)(pg), gdje je pg zaštitna skupina za amin i b) skidanja zaštitne skupine amina, ili c) izvođenja reakcije Heckovog spajanja između 3-halo-5-izopropoksipiridina i spoja formule (R)-CH2=CH-CH2-CH(CH3)OH i d) pretvaranja OH skupine u NHCH3skupinu e) gdje b) ili d) dovode do smjese spoja koja obuhvaća (2S)-(4E)-N-metil-5-(5-izopropoksi-3-piridinil)-4-penten-2-amin, odgovarajući spoj Z-metanikotina i druge izomere, f) stvaranje p-hidroksibenzoatne soli reakcijom smjese sa p-hidroksibenzoevom kiselinom, gdje molarni odnos E-metanikotina prema hidroksibenzoevoj kiselini je u opsegu od 1:2 do 2:1.
HRP20130215TT 2004-11-10 2013-03-12 Hidrobenzoatne soli spojeva metanikotina HRP20130215T1 (hr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US62675104P 2004-11-10 2004-11-10

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HRP20130215T1 true HRP20130215T1 (hr) 2013-04-30

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HRP20130215TT HRP20130215T1 (hr) 2004-11-10 2013-03-12 Hidrobenzoatne soli spojeva metanikotina

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US (2) US20060122238A1 (hr)
EP (3) EP1814853A2 (hr)
JP (3) JP2008519766A (hr)
KR (1) KR101268890B1 (hr)
CN (3) CN101068784A (hr)
AU (2) AU2005304526B2 (hr)
BR (1) BRPI0517621A (hr)
CA (3) CA2793138C (hr)
CY (1) CY1113542T1 (hr)
DK (1) DK2371818T3 (hr)
ES (1) ES2404506T3 (hr)
HR (1) HRP20130215T1 (hr)
IL (2) IL182573A (hr)
ME (1) ME01503B (hr)
MX (1) MX2007005710A (hr)
NO (1) NO20072160L (hr)
NZ (1) NZ554689A (hr)
PL (1) PL2371818T3 (hr)
PT (1) PT2371818E (hr)
RS (1) RS52681B (hr)
RU (1) RU2409566C2 (hr)
SG (1) SG157379A1 (hr)
SI (1) SI2371818T1 (hr)
UA (1) UA88792C2 (hr)
WO (2) WO2006053082A2 (hr)
ZA (2) ZA200703759B (hr)

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