HRP20110043T1 - Derivati 5-piridazinil-1-azabiciklo[3.2.1]oktana, njihovo dobivanje i njihova upotreba u terapiji - Google Patents
Derivati 5-piridazinil-1-azabiciklo[3.2.1]oktana, njihovo dobivanje i njihova upotreba u terapiji Download PDFInfo
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- HRP20110043T1 HRP20110043T1 HR20110043T HRP20110043T HRP20110043T1 HR P20110043 T1 HRP20110043 T1 HR P20110043T1 HR 20110043 T HR20110043 T HR 20110043T HR P20110043 T HRP20110043 T HR P20110043T HR P20110043 T1 HRP20110043 T1 HR P20110043T1
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- Prior art keywords
- compound
- formula
- azabicyclo
- octane
- pyridazin
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- 239000003814 drug Substances 0.000 title claims 13
- 238000002360 preparation method Methods 0.000 title claims 13
- DSXZGIRPYFTAGF-UHFFFAOYSA-N 5-pyridazin-3-yl-1-azabicyclo[3.2.1]octane Chemical class C1N(CCC2)CCC21C1=CC=CN=N1 DSXZGIRPYFTAGF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 10
- 125000005843 halogen group Chemical group 0.000 claims abstract 10
- -1 nitro, amino Chemical group 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 239000012453 solvate Substances 0.000 claims abstract 6
- 239000002253 acid Substances 0.000 claims abstract 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 4
- 125000002541 furyl group Chemical group 0.000 claims abstract 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims abstract 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 3
- 125000001425 triazolyl group Chemical group 0.000 claims abstract 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims abstract 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 229940079593 drug Drugs 0.000 claims 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 claims 5
- 230000032683 aging Effects 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 208000028867 ischemia Diseases 0.000 claims 4
- 210000003141 lower extremity Anatomy 0.000 claims 4
- 230000007170 pathology Effects 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 3
- 229910052763 palladium Inorganic materials 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- 208000006264 Korsakoff syndrome Diseases 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 241000208125 Nicotiana Species 0.000 claims 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010034010 Parkinsonism Diseases 0.000 claims 2
- 206010039580 Scar Diseases 0.000 claims 2
- 206010044688 Trisomy 21 Diseases 0.000 claims 2
- 208000000558 Varicose Ulcer Diseases 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 208000029650 alcohol withdrawal Diseases 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- 206010003230 arteritis Diseases 0.000 claims 2
- 230000009901 attention process Effects 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 230000003920 cognitive function Effects 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000006870 function Effects 0.000 claims 2
- 230000001146 hypoxic effect Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 210000003625 skull Anatomy 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 201000002282 venous insufficiency Diseases 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
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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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
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Abstract
Spoj formule (I) naznačen time što: R jebilo atom vodika ili halogena; ili fenilna skupina, izborno supstituirana s jednim ili više atoma halogena, ili s jednom ili više skupina, koje se bira između (C1-C6)alkilne, (C1-C6)alkoksi, nitro, amino, di(C1-C3)alkilamino, trifluormetilne, trifluormetoksi, cijano, hidroksilne, acetilne ili metilendioksi skupine; ili skupina koju se bira između piridinila, pirazolila, imidazolila, triazolila, tetrazolila, oksazolila, tiazolila, oksadiazolila, tiadiazolila, tienila, furila, izoksazolila, izotiazolila, pirolila i naftila, gdje ova skupina može biti izborno supstituirana s jednom ili više skupina, koje se bira između atoma halogena i (C1-C6)alkilne, (C1-C6)alkoksi, trifluormetoksi, trifluormetilne, nitro, cijano, hidroksilne, amino, (C1-C6)alkilamino ili di(C1-C6)alkilamino skupine; u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata. Patent sadrži još 18 patentnih zahtjeva.
Claims (19)
1. Spoj formule (I)
[image]
naznačen time što:
R je
bilo atom vodika ili halogena;
ili fenilna skupina, izborno supstituirana s jednim ili više atoma halogena, ili s jednom ili više skupina, koje se bira između (C1-C6)alkilne, (C1-C6)alkoksi, nitro, amino, di(C1-C3)alkilamino, trifluormetilne, trifluormetoksi, cijano, hidroksilne, acetilne ili metilendioksi skupine;
ili skupina koju se bira između piridinila, pirazolila, imidazolila, triazolila, tetrazolila, oksazolila, tiazolila, oksadiazolila, tiadiazolila, tienila, furila, izoksazolila, izotiazolila, pirolila i naftila, gdje ova skupina može biti izborno supstituirana s jednom ili više skupina, koje se bira između atoma halogena i (C1-C6)alkilne, (C1-C6)alkoksi, trifluormetoksi, trifluormetilne, nitro, cijano, hidroksilne, amino, (C1-C6)alkilamino ili di(C1-C6)alkilamino skupine;
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
2. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što
R je
bilo halogen atom,
ili fenilna skupina, izborno supstituirana s jednim ili više atoma halogena ili s jednom ili više skupina koje se bira između (C1-C6)alkilne i (C1-C6)alkoksi skupine;
ili skupina koju se bira između piridinila, pirazolila, imidazolila, triazolila, tetrazolila, oksazolila, tiazolila, oksadiazolila, tiadiazolila, tienila, furila, izoksazolila, izotiazolila, pirolila i naftila, gdje ova skupina može biti izborno supstituirana s jednom ili više (C1-C6)alkilnih skupina,
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
3. Spoj formule (I) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što
R je
bilo halogen atom;
ili fenilna skupina, izborno supstituirana s jednim ili više atoma halogena ili s jednom ili više skupina koje se bira između (C1-C6)alkilne i (C1-C6)alkoksi skupine;
ili skupina koju se bira između piridinila, pirazolila, imidazolila, tienila, furila i pirolila, gdje ova skupina može biti izborno supstituirana s jednom ili više (C1-C6)alkilnih skupina;
u obliku baze ili adicijske soli s kiselinom, te također u obliku hidrata ili solvata.
4. Spoj formule (I) u skladu s jedan od patentnih zahtjeva 1 do 3, naznačen time što ga se bira između:
– 5-(6-fenilpiridazin-3-il)-1-azabiciklo[3.2.1]oktana
– 5-(6-(3-furil)piridazin-3-il)-1-azabiciklo[3.2.1]oktana
– 5-(6-(4-metil-2-tienil)piridazin-3-il)-1-azabiciklo[3.2.1]oktana
– 5-(6-klorpiridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– 5-(6-(5-metil-2-tienil)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– 5-(6-(3,5-dimetil)fenilpiridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– 5-(6-(4-metoksi)fenilpiridazin-3-il)-1-azabiciklo-[3.2.1]oktan-hidroklorida (1:1)
– 5-(6-(2-furil)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– 5-(6-(3,4-dimetoksi)fenilpiridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– 5-(6-(3-fluor)fenilpiridazin-3-il)-1-azabiciklo-[3.2.1]oktan-hidroklorida (1:1)
– 5-(6-(3-klor)fenilpiridazin-3-il)-1-azabiciklo-[3.2.1]oktan-hidroklorida (1:1)
– (+)-5-(6-(3,5-dimetil-4-pirazolil)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– (+)-5-(6-(1H-pirol-2-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktana
– 5-(6-(1H-piridin-3-il)piridazin-3-il)-1-azabiciklo-[3.2.1]oktana
– (–)-5-(6-(5-metil-2-tienil)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– (+)-5-(6-(3-furil)piridazin-3-il)-1-azabiciklo-[3.2.1]oktan-hidroklorida (1:1)
– (+)-5-(6-(5-metil-2-tienil)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– (–)-5-(6-(1H-imidazol-4-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– (+)-5-(6-(1H-imidazol-4-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidroklorida (1:1)
– (–)-5-(6-(1H-pirazol-4-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2)
– (–)-5-(6-(1-metil-1H-pirazol-4-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2)
– (+)-5-(6-(1H-pirazol-4-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2)
– (+)-5-(6-(1-metil-1H-pirazol-4-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2)
– (–)-5-(6-(1H-imidazol-2-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2)
– (+)-5-(6-(1H-imidazol-1-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktana
– (–)-5-(6-(1H-imidazol-1-il)piridazin-3-il)-1-azabiciklo[3.2.1]oktana.
5. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što spoj formule (VII)
[image]
reagira
bilo s boronskom kiselinom formule R-B(OH)2, u kojoj R je kao što je definirano u formuli (I), u prisutnosti paladijskog katalizatora;
ili sa spojem formule R-H, u kojoj R je kao što je definirano u formuli (I), u prisutnosti jake baze, u otapalu;
ili s derivatom kositra formule R-Sn[(CH2)3CH3)]3, u kojoj R je kao što je definirano u formuli (I), u prisutnosti paladijskog katalizatora;
ili sa spojem formule R-H, u kojoj R je kao što je definirano u formuli (I), u prisutnosti n-butillitija, cinkovog klorida i paladijskog katalizatora.
6. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili adicijsku sol ovog spoja s farmaceutski prihvatljivom kiselinom, ili njegov hidrat ili solvat.
7. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, ili farmaceutski prihvatljivu sol, hidrat ili solvat ovog spoja, te također najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
8. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju i sprječavanju poremećaja kognitivnih funkcija; pogođenih procesa pažljivosti; problema s egzekutivnim funkcijama povezanih s Alzheimerovom bolešću, s patološkim starenjem ili normalnim starenjem, s Parkinsonovim sindromom, s trisomijom 21, s psihijatrijskim patologijama, s alkoholnim Korsakovljevim sindromom, s vaskularnim demencijama, s ozljedama lubanje; motoričkih problema, opaženih kod Parkinsonove bolesti ili drugih neuroloških bolesti ili anatomsko-histopatološkog oštećenja, povezanog s gore navedenim neurodegenerativnim bolestima.
9. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju i sprječavanju cerebralnih inzulta, hipoksičnih epizoda u mozgu ili psihijatrijskih patologija.
10. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u sprječavanju simptoma ustezanja od duhana, ustezanja od alkohola ili ustezanja od različitih tvari koje uzrokuju ovisnost.
11. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju boli.
12. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju ishemije donjih udova, obliterativnog arteritisa donjih udova, ishemije srca, infarkta miokarda, insuficijencije srca, deficijencije ožiljavanja kože kod dijabetičnih pacijenata, te varikoznih ulkusa kod venske insuficijencije.
13. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju upalnih procesa.
14. Spoj formule (I) u skladu s jedan od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju i sprječavanju poremećaja kognitivnih funkcija; pogođenih procesa pažljivosti; problema s egzekutivnim funkcijama povezanih s Alzheimerovom bolešću, s patološkim starenjem ili normalnim starenjem, s Parkinsonovim sindromom, s trisomijom 21, s psihijatrijskim patologijama, s alkoholnim Korsakovljevim sindromom, s vaskularnim demencijama, s ozljedama lubanje; motoričkih problema, opaženih kod Parkinsonove bolesti ili drugih neuroloških bolesti ili anatomsko-histopatološkog oštećenja, povezanog s gore navedenim neurodegenerativnim bolestima.
15. Spoj formule (I) u skladu s jedan od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju i sprječavanju cerebralnih inzulta, hipoksičnih epizoda u mozgu ili psihijatrijskih patologija.
16. Spoj formule (I) u skladu s jedan od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u sprječavanju simptoma ustezanja od duhana, ustezanja od alkohola ili ustezanja od različitih tvari koje uzrokuju ovisnost.
17. Spoj formule (I) u skladu s jedan od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju boli.
18. Spoj formule (I) u skladu s jedan od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju ishemije donjih udova, obliterativnog arteritisa donjih udova, ishemije srca, infarkta miokarda, insuficijencije srca, deficijencije ožiljavanja kože kod dijabetičnih pacijenata, te varikoznih ulkusa kod venske insuficijencije.
19. Spoj formule (I) u skladu s jedan od patentnih zahtjeva 1 do 4, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju upalnih procesa.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0508594A FR2889847B1 (fr) | 2005-08-18 | 2005-08-18 | Derives de 5-pyridazinyl-1-azabicyclo[3.2.1]octave, leur preparation en therapeutique. |
| PCT/FR2006/001911 WO2007020343A1 (fr) | 2005-08-18 | 2006-08-07 | Derives de 5-pyridazinyl-1-azabicyclo[3.2.1]octane, leur preparation et leur application en therapeutique |
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| Publication Number | Publication Date |
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| HRP20110043T1 true HRP20110043T1 (hr) | 2011-02-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| HR20110043T HRP20110043T1 (hr) | 2005-08-18 | 2011-01-20 | Derivati 5-piridazinil-1-azabiciklo[3.2.1]oktana, njihovo dobivanje i njihova upotreba u terapiji |
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| Country | Link |
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| US (3) | US7476674B2 (hr) |
| EP (1) | EP1922320B1 (hr) |
| JP (1) | JP5249758B2 (hr) |
| KR (1) | KR101260546B1 (hr) |
| CN (2) | CN102558177A (hr) |
| AR (1) | AR056461A1 (hr) |
| AT (1) | ATE486073T1 (hr) |
| AU (1) | AU2006281340B2 (hr) |
| BR (1) | BRPI0614796A2 (hr) |
| CA (1) | CA2618110C (hr) |
| CR (1) | CR9693A (hr) |
| CY (1) | CY1111101T1 (hr) |
| DE (1) | DE602006017854D1 (hr) |
| DK (1) | DK1922320T3 (hr) |
| DO (1) | DOP2006000191A (hr) |
| EA (1) | EA013601B1 (hr) |
| EC (1) | ECSP088182A (hr) |
| ES (1) | ES2354833T3 (hr) |
| FR (1) | FR2889847B1 (hr) |
| HK (1) | HK1125628A1 (hr) |
| HN (1) | HN2008000276A (hr) |
| HR (1) | HRP20110043T1 (hr) |
| IL (1) | IL189014A0 (hr) |
| JO (1) | JO2680B1 (hr) |
| MA (1) | MA29913B1 (hr) |
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| MY (1) | MY145923A (hr) |
| NO (1) | NO20081289L (hr) |
| NZ (1) | NZ565537A (hr) |
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| PT (1) | PT1922320E (hr) |
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| SI (1) | SI1922320T1 (hr) |
| TN (1) | TNSN08026A1 (hr) |
| TW (1) | TWI322808B (hr) |
| UA (1) | UA92360C2 (hr) |
| UY (1) | UY29756A1 (hr) |
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| US9249307B2 (en) | 2011-08-16 | 2016-02-02 | Pierce Biotechnology, Inc. | Benzocyanine compounds |
| US20220347175A1 (en) | 2018-07-19 | 2022-11-03 | Sumitomo Dainippon Pharma Co., Ltd. | Pyridazinone derivative |
| US20230109839A1 (en) | 2020-01-07 | 2023-04-13 | Sumitomo Pharma Co., Ltd. | Therapeutic agent for tauopathies |
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| FR2786770B1 (fr) * | 1998-12-04 | 2001-01-19 | Synthelabo | Derives de 1,4-diazabicyclo[3.2.2.]nonane, leur preparation et leur application en therapeutique |
| FR2786769B1 (fr) * | 1998-12-04 | 2002-10-25 | Synthelabo | Derives de 2,5-diazabicyclo[2.2.1]heptane, leur preparation et leur application en therapeutique |
| US6277855B1 (en) | 2000-04-21 | 2001-08-21 | Inspire Pharmaceuticals, Inc. | Method of treating dry eye disease with nicotinic acetylcholine receptor agonists |
| ES2223209B1 (es) | 2001-12-11 | 2005-10-01 | Esteve Quimica, S.A. | Nuevas formas cristalinas del meloxicam y procedimientos para su preparacion e interconversion. |
| JP4312456B2 (ja) | 2000-10-13 | 2009-08-12 | ニューロサーチ、アクティーゼルスカブ | ニコチン性レセプターアゴニスト及びモノアミン作動性物質の組み合わせ作用による情動障害の治療法 |
| FR2834511B1 (fr) * | 2002-01-07 | 2004-02-13 | Sanofi Synthelabo | Derives de 5-(pyridin-3-yl)-1-azabicyclo[3.2.1]octane, leur preparation et leur application en therapeutique |
| US6644511B2 (en) | 2002-01-11 | 2003-11-11 | Unilever Home & Personal Care Usa, A Division Of Conopco, Inc. | Container for dispensing a dual phase fluid product |
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