SI20269B - Derivati acil-piperazinil-pirimidinov, njihova priprava in uporaba kot zdravila - Google Patents
Derivati acil-piperazinil-pirimidinov, njihova priprava in uporaba kot zdravila Download PDFInfo
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- SI20269B SI20269B SI9820053A SI9820053A SI20269B SI 20269 B SI20269 B SI 20269B SI 9820053 A SI9820053 A SI 9820053A SI 9820053 A SI9820053 A SI 9820053A SI 20269 B SI20269 B SI 20269B
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- piperazinyl
- methoxypyrimidine
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Claims (18)
- λ PATENTNI ZAHTEVKI 1. Derivat acil-piperazinil-pirimidina s splošno formulo (I)
- 2. Spojina po zahtevku 1, v katerem je Ri metoksi, etoksi, propoksi, izopropoksi, butoksi, sec-butoksi ali tert-butoksi.
- 3. Spojina po zahtevku 1, v katerem je R2 metil, etil, propil, izopropil, butil, izobutil, sec-butil, tert-butil, pentil, izopentil, neopentil ali heksil.
- 4. Spojina po zahtevku 1, v katerem je R2 ciklopropil, ciklobutil, ciklopentil ali cikloheksil.
- 5. Spojina po zahtevku 1, v katerem je R2 2-aziridinil, 2-tetrahidrofuril, 3-tetrahidrofuril, 2-tetrahidrotienil, 3-tetrahidrotienil, 2-azetidinil, 2-pirolidinil, 3-pirolidinil, 2-piperidinil, 3-piperidinil ali 4-piperidinil. 3
- 6. Spojina po zahtevku 1, v katerem je R2 2-fluorofenil, 3- fluorofenil, 4-fluorofenil, 2-klorofenil, 3-klorofenil, 4-klorofenil, 2- bromofenil, 3-bromofenil, 4-bromofenil, 2-aminofenil, 3-aminofenil, 4- 5 aminofenil, 2-nitrofenil, 3-nitrofenil, 4-nitrofenil. 2-acetamidofenil, 3- acetamidofenil, 4-acetamidofenil, 2-nitrofenil. 3-nitrofenil, 4-nitrofenil, 2-metilfenil, 3-metilfenil, 4-metilfenil, 2-(trifluorometil)fenil, 3-(trifluorometil)fenil, 4-(trifluorometil)fenil, 2-metoksifenil, 3-metoksifenil, 4-metoksifenil, 2,3-difluorofenil, 3,4-difluorofenil, 2,4-difluorofenil, 2,3- io dibromofenil, 3,4-dibromofenil, 2,4-dibromofenil, 2,3-dimetilfenil, 3,4- dimetilfenil, 2,4-dimetilfenil, 2,3-dimetoksifenil, 3,4-dimetoksifenil, 2,4- dimetoksifenil.
- 7. Spojina po zahtevku 1, v katerem je R2 fenilmetil, l-feniletil, is 2-feniletil, 3-fenilpropil, po možnosti zamenjan na aromatskem obroču.
- 8. Spojina po zahtevku 1, v katerem je R2 2-furil, 3-furil, 2-tienil, 3-tienil, 3-metil-2-tienil, 5-metil-2-tienil, 3-metoksi-2-tienil, 3-kloro-2-tienil, 5-kloro-2-tienil, 2-pirolil, 3-pirolil, 2-piridil, 3-piridil, 4-piridil, 2- 2o indolil, 3-indolil, 2-benzo[b]tienil, 3-benzo[b]tienil, 3-kloro-2-benzo[b]tienil, pirazolil, imidazolil, pirimidmil, piridazinil, pirazinil, benzimidazolil, kinolil, oksazolil ali tiazolil.
- 9. Spojina po zahtevku 1, v katerem je R2 2-tienilmetil, 2-benzo[b]tienmetil ali 3-(4-kloropirazolil)propil.
- 10. Spojina po zahtevku 1, ki je izbrana iz naslednje skupine: • 2-[4-(2-furilkarbonil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(2-furilkarbonil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 4-metoksi-2-[4-(2-tienilkarbonil)-l-piperazinil]pirimidin, • 4-metoksi-2-[4-(2-tienilkarbonil)-1 -piperaziniljpirimidin klorohidrat, • 2-(4-acetil-l-piperazinil)-4-metoksipirimidin, • 2-{4-[4-(4-kloropirazolil)butanoil]-1-piperazinil}-4-metoksipirimidin, • 2-{4-[4-(4-kloropirazolil)butanoil]-1 -piperazinil}-4-metoksipirimidin klorohidrat, • 2-(4-benzoil-1 -piperazinil)4-metoksipirimidin, • 2-(4-ciklopropilkarbonil-1 -piperazinilH-metoksipirimidin, • 2-[4-(2-furilkarbonil)-l-piperazinil]4-(trifluorometil)pirimidin, • 2-[4-(2-tienilkarbonil)-l-piperazinil]4-(trifluorometil)pirimidin, • 4-metoksi-2-[4-(3-tienilkarbonil)-1 -piperaziniljpirimidin, • 4-metoksi-2-[4-(3-tienilkarbonil)-l-piperazinil]pirimidinklorohidrat, • 2-[4-(5-meti!-2-tienilkarbonil)-1-piperazinil]-4-metoksipirimidin, • 2-[4-(5-metil-2-tienilkarbonil)-1 -piperazinil]-4-metoksipirimidin klorohidrat, • 4-metoksi-2-[4-(3-metoksi-2-tienilkarbonil)-1-piperazinil]pirimidin, • 4-metoksi-2-[4-(3-metoksi-2-tienilkarbonil)-1 -piperaziniljpirimidin klorohidrat, • 2-[4-(2-benzo[b]tienilkarbonil)-l-piperazinil]-4-metokšipirimidin, • 2-[4-(2-benzo[b]tienilkarbonil)-1 -piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(2-indolilkarbonil)-1 -piperazinil]4-metoksipirimidin, • 2-[4-(3-kloro-2-benzo[b]tienilkarbonil)-l-piperazinil]-4- metoksipirimidin, • 2-[4-(3-kloro-2-benzo[b]tienilkarbonil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 4-metoksi-2-[4-(2-pirolilkarbonil)-1-piperazinil]pirimidin, • 4-metoksi-2-[4-(2-pirolilkarbonil)-1-piperazinil]pirimidin klorohidrat, • 4-metoksi-2-[4-(2-tienilacetil)-1 -piperazinil]pirimidin, • 4-metoksi-2-[4-(2-tienilacetil)-1 -piperazinil]pirimidin klorohidrat, • 2-[4-(3-metil-2-tienilkarbonil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(3-metil-2-tienilkarbonil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(3-kloro-2-tienilkarbonil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(3-kloro-2-tienilkarbonil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(3-indolilkarbonil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-{3-benzo[b]tienilacetil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(5-kloro-2-tienilkarbonil)-1-piperazinil]-4-metoksipirimidin, • 2-[4-(5-kloro-2-tienilkarbonil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 4-metoksi-2-[4-(4-klorobenzoil)-l-piperazinil]-4-metoksipirimidin, • 4-metoksi-2-[4-(4-klorobenzoil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(4-fluorobenzoil)-1 -piperazinil]-4-metoksipirimidin, • 2-[4-(4-fluorobenzoil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(4-klorobenzoil)-1 -piperazinil]-4-metoksipirimidin, • 2-[4-(4-klorobenzoil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 4-metoksi-2-[4-(3-metoksibenzoil)-l-piperazinil]pirimidin, • 4-metoksi-2-[4-(3-metoksibenzoil)-1 -piperazinil]pirimidin klorohidrat, • 2-[4-(3-fluorobenzoil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(l-fluorobenzoil)-1 -piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(3-klorobenzoil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(3-klorobenzoil)-1-piperazinil]-4-metoksipirimidin klorohidrat, • 4-metoksi-2-[4-(2-metoksibenzoil)-1 -piperazinil]pirimidin, • 4-metoksi-2-[4-(2-metoksibenzoil)-1 -piperazinil]pirimidin klorohidrat, • 2-[4-(2-(fluorobenzoil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(2-(fluorobenzoil)-l-piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(2-(klorobenzoil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(2-(klorobenzoil)-1 -piperazinil]-4-metoksipirimidin klorohidrat, • 4-metoksi-2-[4-(2-tetrahidrofurilkarbonil)-1-piperazinil]pirimidin, • 4-metoksi-2-(4-tiobenzoil-1 -piperazinil)pirimidin, • 4-metoksi-2-[4-(2-tetrahidrofurilkarbonil)-1 -piperazinil]pirimidin klorohidrat, • 4-metoksi-2-(4-tiobenzoil-1 -piperazinil)pirimidin klorohidrat, • 2-(4-benzoil-1-piperazinil)-4-metoksipirimidin, • 4-metoksi-2-{4-[4-(trifluorometil)benzoil]-l-piperazinil}pirimidin, • 4-metoksi-2-{4-[4-(trifluorometil)benzoil]-l-piperazinil}pirimidin klorohidrat, • 4-metoksi-2-{4-[3-(trifluorometil)benzoil]-l-piperazinil}pirimidin, • 4-metoksi-2-{4-[3-(trifluorometil)benzoil]-1 -piperaziniljpirimidin klorohidrat, • 4-metoksi-2-{4-[2-(trifluorometil)benzoil]-l-piperazinil}pirimidin, • 4-metoksi-2-{4-[2-(trifluorometil)benzoil]-l-piperazinil}pirimidin klorohidrat, • 4-metoksi-2-(4-nikotinoil-1-piperazinil)pirimidin, • 4-metoksi-2-(4-nikotinoil-1 -piperazinil)pirimidin diklorohidrat, • 2-(4-izonikotinoil-1-piperazinil)-4-metoksipirimidin, • 2-(4-izonikotinoil-1 -piperazinil)-4-metoksipirimidin diklorohidrat, • 2-[4-(1-imidazolilkarbonil)-1-piperazinil]-4-metoksipirimidin, • 2-[4-(1 -imidazolilkarbonil)-1 -piperazinil]-4-metoksipirimidin klorohidrat, • 2-(4-nikotinoil-1-piperazinil)-4-(trifluorometil)pirimidin, • 2-(4-nikotinoil-1 -piperazinil)-4-(trifIuorometil)pirimidin klorohidrat, • 4-metoksi-2-,4-(2-piridilkarbonil)-l-piperazinil]pirimidin, • 4-metoksi-2-’4-(2-piridilkarbonil)-1 -piperazinil]pirimidin diklorohidrat, • 4-etoksi-2-[4-(2-tienilkarbonil)-1 -piperazinil]pirimidin, • 4-etoksi-2-[4-(2-tienilkarbonil)-1 -piperazinil]pirimidin klorohidrat, • 2-[4-(3-kloro-2-tienilkarbonil)-l-piperazinil]-4-etoksipirimidin, • 2-[4-{3-kloro-2-tienilkarbonil)-l-piperazinil]-4-etoksipirimidin klorohidrat, • 4-etoksi-2-{4-[2-(trifluorometil)benzoil]-l-piperazinil}pirimidin, • 4-etoksi-2-{4-[2-(trifluorometil)benzoil]-l-piperazinil}pirimidin klorohidrat, • 2-[4-(2-metilbenzoil)-1-piperazinil]-4-metoksipirimidin, • 2-[4-(2-metilbenzoil)-1 -piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(4-fluorobenzoil)-1-piperazinil]-4-izopropoksipirimidin, • 2-[4-(4-fluorobenzoil)-1 -piperazinil]-4-izopropoksipirimidin klorohidrat, • 4-izopropoksi-2-{4-[2-(trifluorometil)benzoil]-1-piperazinil]pirimidin, • 4-izopropoksi-2-{4-[2-(trifluorometil)benzoil]-l-piperazinil]pirimidin klorohidrat, • 2-[4-(3-kloro-2-tienkarbonil)-l-piperazinil]-4-izopropoksipirimidin, • 2-[4-(3-k!oro-2-tienkarbonil)-l-piperazinil]-4-izopropoksipirimidin klorohidrat, • 2-[4-(cikloheksilkarbonil)-1-piperazinil]-4-metoksipirimidin, • 2-[4-(cikloheksilkarbonil)-1 -piperazinil]-4-metoksipirimidin klorohidrat, • 4-etoksi-2[4-(4-fluorobenzoil]-1-piperazinil}pirimidin, • 4-etoksi-2[4-(4-fluorobenzoil]-1 -piperaziniljpirimidin klorohidrat, • 2-[4-(2-tiazoiilkarbonil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(2-aminobenzoil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(2-aminobenzoil)-l-piperazinit]-4-metoksipirimidin klorohidrat, • 2-[4-(3-fluoro-2-tieilkarbonil)-l-piperazinil]-4-metoksipirimidin> • 2-[4-(3-fluoro-2-tieilkarbonil)"l-piperazinil]-4-metoksipirimidin klorohidrat, • 2-[4-(4-metoksi-2-pirimidinil)-1-piperazinilkarbonil]benzoična kislina • 2-[4-(2-acetoksibenzoil)-l-piperazinil]-4-metoksipirimidin, • 2-[4-(2-hidroksibenzoil)-l-piperazinil]-4-metoksipirimidin, • natrijev 2-[4-(4-metoksi-2-pirimidinil)-l-piperazinilkarbonil]benzoat, • 2-[4-(2-hidroksibenzoil)-1 -piperazinil]-4-metoksipirimidin hidroklorat, • 4-metoksi-2-[4-(2-metoksibenzoil)-l-piperazinill-4-metoksipirimidin, in • 4-etoksi-2[4-(2-piridilkarbonil]-l-piperazinil}pirimidin.N10 kjer je X atom kisika ali žvepla; R1 alkoksi Cm ali trifluorometilni radikal; R2 alkilni radikal C^; nasičeni cikloalkil C^; heterocikloalkil vsebuje obroč s 3 do 6 atomi, v katerem je heteroatom izbran izmed is atoma kisika, žvepla ali dušika, po možnosti je N zamenjan z alkilom Ci -C6; fenil, ki je po možnosti zamenjan z 1, 2 ali 3 identičnimi ali različnimi nadomestki, izbranimi izmed fluora, klora, broma, amino, acetamido, nitro, metila, trifluorometila in metoksi; arilalkil, ki obsega alkilno skupino Cm, ki je zamenjana s fenilnim radikalom, ki je po možnosti zamenjan z 1, 2 ali 3 m identičnimi ali različnimi nadomestki, izbranimi izmed fluora, klora, broma, amino, acetamido, nitro, metila, trifluorometila in metoksi; heteroaril vsebuje obroč s 5 ali 6 heteroatomi, ki so po možnosti zamenjani, ali spojene heteroaromatske sisteme, ki so po možnosti zamenjani, 9 ali 10 1. atomov, ki vsebujejo 1 ali 2 heteroatoma, ki sta izbrana izmed kisika, žvepla in dušika, prej omenjeni nadomestki so izbrani izmed fluora, klora, broma, amino, acetamido, nitro, metila, trifluorometila in metoksi; in heteroalkil, ki vsebuje alkilno skupino iz 1 do 3 ogljikovih atomov, ki so zamenjani s heteroarilnim radikalom, ki obsega 5 ali 6 členski heteroaromatski obroč, ki je po možnosti zamenjan, ali spojeni 9 do 10 členski heteroaromatski sistemi, ki so po možnosti zamenjani z 1 ali 2 heteroatomom, ki sta izbrana izmed kisika, žvepla in dušika, prej omenjeni nadomestki so izbrani izmed fluora, klora, broma, amino, acetamido, nitro, metila, trifluorometila in metoksi; in njihove fiziološko sprejemljive soli.
- 11. Postopek za pripravo spojine s splošno formulo (I), v kateri X predstavlja atom kisika po zahtevku 1, ki obsega reakcijo derivata kloropirimidina s formulo (III) ^ (»O kjer ima R-j pomen, ki je definiran v zahtevku 1, z derivatom piperazina s splošno formulo (IV) X kjer ima R2 pomen, ki je definiran v zahtevku 1 in X predstavlja atom kisika.(V)
- 12. Postopek za pripravo spojine s splošno formulo (I), v kateri X predstavlja atom kisika po zahtevku 1, ki obsega reakcijo amina s formulo (V) kjer ima Ri pomen, ki je definiran v zahtevku 1, s karboksilno kislino s formulo R2COOH (VI) ali s soljo omenjene kisline, v kateri ima R2 pomen, ki je definiran v zahtevku 1.
- 13. Postopek za pripravo spojine s splošno formulo (I), v kateri X predstavlja atom kisika po zahtevku 1, ki obsega reakcijo amina s formulo (V) R(V) kjer ima Ri pomen, ki je definiran v zahtevku 1 Αϋ z derivatnim reagentom R2COY (VII), v katerem ima R2 pomen, ki je definiran v zahtevku 1 in Y predstavlja halogeni atom, azidno skupino, 1-imidazolilno skupino, skupino O-CO-R4, kjer R4 predstavlja alkilni radikal iz 1 do 6 atomov ogljika ali arilnega radikala, ki je po možnosti zamenjan z 5 enim ali večimi halogenimi atomi, ali skupino OR5, kjer R5 predstavlja aromatsko skupino ali en ali dva obroča, zamenjana z enim ali večimi halogenimi atomi ali nitro radikali, ali N-sukcinimid.
- 14. Postopek za pripravo spojine s splošno formulo (I), v kateri X 10 predstavlja atom žvepla po zahtevku 1, ki obsega reakcijo spojine s splošno formulo (I), v kateri X predstavlja atom kisika, z Lavvessonovim reagentom,(2,4'bis(4-metoksifenil)-1,3,2,4-ditiadifosfaetano-2,4-disulfurid), ali z fosfor pentasulfidom. is
- 15. Postopek za pripravo fiziološko sprejemljivih soli spojin s splošno formulo (I) po zahtevku 1, ki obsega reakcijo spojine s splošno formulo (I) z mineralno kislino ali organsko kislino v ustreznem topilu.
- 16. Farmacevtska zmes, ki je označena s tem, da vsebuje poleg 20 farmacevtsko sprejemljivega nosilca zdravila vsaj eno spojino s splošno formulo (I) ali eno od njenih fiziološko sprejemljivih soli po zahtevkih 1 do 10.
- 17. Uporaba spojine s splošno formulo (I) ali njenih farmacevtsko sprejemljivih soli po kateremkoli izmed zahtevkov 1 do 10 v izdelavi zdravila z delovanjem na centralni živčni sistem sesalcev, vključno s človekom.
- 18. Uporaba spojine s splošno formulo (I) ali njenih farmacevtsko sprejemljivih soli po kateremkoli izmed zahtevkov 1 do 10 v izdelavi zdravila s sedativnim, antikonvulzantnim, analgetičnim, mišično relaksantnim, antitusigenim, anksiolitičnim, antipsihotičnim, antidepresivnim, antimigrenskim in antiishemičnim (v možganih) delovanjem, v izdelavi zdravila za zdravljenje motenj spanja, nevrodegenerativnih bolezni, motenj prepoznavanja in Alzheimerjeve bolezni, uspavalnih sredstev ali sredstev za splošno anastezijo za sesalce, vključno s človekom. Za: LABORATORIOS DEL DR. ESTEVE, S.A.
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ES009701627A ES2125206B1 (es) | 1997-07-21 | 1997-07-21 | Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos. |
PCT/ES1998/000212 WO1999005121A1 (es) | 1997-07-21 | 1998-07-21 | Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos |
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PL375527A1 (en) * | 2002-06-29 | 2005-11-28 | Zentaris Gmbh | Arylcarbonylpiperazines and heteroarylcarbonylpiperazines and the use thereof for treating benign and malignant tumour diseases |
US20040127395A1 (en) * | 2002-09-06 | 2004-07-01 | Desai Pragnya J. | Use of histamine H4 receptor modulators for the treatment of allergy and asthma |
EP1720545B1 (en) | 2004-03-03 | 2014-10-29 | ChemoCentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
US7435831B2 (en) | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
WO2006034279A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
BRPI0515478A (pt) * | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seu uso como mediadores de estearoil-coa-desaturase |
CN101084207A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶抑制剂的用途 |
CN101083982A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 用于治疗硬脂酰CoA去饱和酶介导的疾病的杂环衍生物 |
AU2005329423A1 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
TW200626154A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
CN101083986A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 双环杂环衍生物及其作为硬脂酰CoA去饱和酶(SCD)抑制剂的用途 |
TW200626155A (en) * | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
AR051095A1 (es) * | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso comoinhibidores de la estearoil-coa desaturasa |
BRPI0611187A2 (pt) * | 2005-06-03 | 2010-08-24 | Xenon Pharmaceuticals Inc | derivados aminotiazàis como inibidores da estearoil-coa desaturase humana |
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US8609672B2 (en) | 2010-08-27 | 2013-12-17 | University Of The Pacific | Piperazinylpyrimidine analogues as protein kinase inhibitors |
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JP2016513112A (ja) * | 2013-02-18 | 2016-05-12 | ザ スクリプス リサーチ インスティテュート | 治療的潜在能力を有するバソプレッシン受容体のモジュレーター |
JP2018012645A (ja) * | 2014-11-26 | 2018-01-25 | 持田製薬株式会社 | 新規ジアザビシクロ誘導体 |
KR20240063881A (ko) * | 2021-07-30 | 2024-05-13 | 콘포 테라퓨틱스 엔.브이. | 통증, 특히 신경병증성 통증, 및/또는 at2r 및/또는 at2r 매개 신호전달과 연관된 다른 질환 또는 장애의 치료를 위한 화합물 |
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- 1998-07-21 JP JP2000504120A patent/JP2001510831A/ja active Pending
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- 1998-07-21 DK DK98933660T patent/DK1006110T3/da active
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- 1998-07-21 BR BR9810772-0A patent/BR9810772A/pt not_active Application Discontinuation
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- 1998-07-21 SI SI9820053A patent/SI20269B/sl not_active IP Right Cessation
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2000
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