HRP20100573T1 - Triazolopiridinkarboksamidni derivati, njihovo dobivanje i njihova upotreba u terapiji - Google Patents
Triazolopiridinkarboksamidni derivati, njihovo dobivanje i njihova upotreba u terapiji Download PDFInfo
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- HRP20100573T1 HRP20100573T1 HR20100573T HRP20100573T HRP20100573T1 HR P20100573 T1 HRP20100573 T1 HR P20100573T1 HR 20100573 T HR20100573 T HR 20100573T HR P20100573 T HRP20100573 T HR P20100573T HR P20100573 T1 HRP20100573 T1 HR P20100573T1
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- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 24
- 150000001875 compounds Chemical class 0.000 claims abstract 24
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 16
- 125000005843 halogen group Chemical group 0.000 claims abstract 12
- 239000012453 solvate Substances 0.000 claims abstract 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 239000002253 acid Substances 0.000 claims abstract 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 3
- 125000004429 atom Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 208000002193 Pain Diseases 0.000 claims 4
- 230000001154 acute effect Effects 0.000 claims 4
- 230000001575 pathological effect Effects 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 208000032928 Dyslipidaemia Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- 206010028813 Nausea Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 229910020008 S(O) Inorganic materials 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 206010047700 Vomiting Diseases 0.000 claims 2
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 2
- 208000005298 acute pain Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052801 chlorine Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 201000003146 cystitis Diseases 0.000 claims 2
- 208000002173 dizziness Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 210000003734 kidney Anatomy 0.000 claims 2
- 210000004072 lung Anatomy 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 230000008693 nausea Effects 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 230000003071 parasitic effect Effects 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 230000003612 virological effect Effects 0.000 claims 2
- 230000008673 vomiting Effects 0.000 claims 2
- RCRCTBLIHCHWDZ-DOFZRALJSA-N 2-arachidonoylglycerol Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)OC(CO)CO RCRCTBLIHCHWDZ-DOFZRALJSA-N 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 235000016709 nutrition Nutrition 0.000 claims 1
- 230000035764 nutrition Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
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Abstract
Spoj formule (I) naznačen time što: X je atom vodika, atom halogena, ili (C1-C6)alkilna, (C1-C6)alkoksi, halogen(C1-C6)alkilna, S(O)mR", hidroksilna ili cijano skupina, A je odsutan ili je veza, atom kisika, atom sumpora, skupina NR, C(C)NR' ili NR', (C1-C2)alkilenska skupina ili (C2)alkenilna skupina, R1 i R2 su, međusobno neovisno, jedna ili više skupina, koje se bira između atoma vodika, (C1-C6)alkilne skupine, (C1-C6)alkoksi skupine, (C3-C7)cikloalkilne skupine, (C3-C7)cikloalkil(C1-C6)alkilne skupine, (C3-C7)cikloalkil(C1-C6)alkoksi skupine, atoma halogena, cijano skupine, skupine C(O)R', C(O)OR', C(O)NR10R20 ili NO2, ili skupine NR10R20 ili NR10C(O)-R20, gdje su (C1-C6)alkilna i (C1-C6)alkoksi skupina being izborno supstituirane s jednim ili više atoma ili skupina, koje se, međusobno neovisno, bira između atoma halogena i hidroksilne, amino ili skupine NR10R20,R je skupina koju se bira između atoma vodika, te (C1-C6)alkilne, (C3-C7)cikloalkilne, (C3-C7)cikloalkil(C1-C6)alkilne, skupine C(O)R', R", CO2R" ili C(O)NR10R20,R' je skupina koju se bira između atoma vodika, (C1-C6)alkilne skupine, (C3-C7)cikloalkilne skupine i (C3-C7)cikloalkil(C1-C6)alkilne skupine, R" je skupina koju se bira između (C1-C6)alkilne skupine, (C3-C7)cikloalkilne skupine i (C3-C7)cikloalkil(C1-C6)alkilne skupine, R10 i R20 su, međusobno neovisno, jedna ili više skupina, koje se bira između atoma vodika, (C1-C6)alkilne skupine, (C3-C7)cikloalkilne skupine i (C3-C7)cikloalkil(C1-C6)alkilne skupine, ili R10 i R20 mogu tvoriti zasićeni ili djelomično nezasićeni prsten s 5 do 7 atoma ugljika i izborno sadrži heteroatom, kojeg se bira između O, N ili S(O)m,m predstavlja 0, 1 ili 2, u obliku baze ili adicijske soli s kiselinom, a također i u obliku hidrata ili solvata. Patent sadrži još 13 patentnih zahtjeva.
Claims (14)
1. Spoj formule (I)
[image]
naznačen time što:
X je atom vodika, atom halogena, ili (C1-C6)alkilna, (C1-C6)alkoksi, halogen(C1-C6)alkilna, S(O)mR", hidroksilna ili cijano skupina,
A je odsutan ili je veza, atom kisika, atom sumpora, skupina NR, C(C)NR' ili NR', (C1-C2)alkilenska skupina ili (C2)alkenilna skupina,
R1 i R2 su, međusobno neovisno, jedna ili više skupina, koje se bira između atoma vodika, (C1-C6)alkilne skupine, (C1-C6)alkoksi skupine, (C3-C7)cikloalkilne skupine, (C3-C7)cikloalkil(C1-C6)alkilne skupine, (C3-C7)cikloalkil(C1-C6)alkoksi skupine, atoma halogena, cijano skupine, skupine C(O)R', C(O)OR', C(O)NR10R20 ili NO2, ili skupine NR10R20 ili NR10C(O)-R20, gdje su (C1-C6)alkilna i (C1-C6)alkoksi skupina being izborno supstituirane s jednim ili više atoma ili skupina, koje se, međusobno neovisno, bira između atoma halogena i hidroksilne, amino ili skupine NR10R20,
R je skupina koju se bira između atoma vodika, te (C1-C6)alkilne, (C3-C7)cikloalkilne, (C3-C7)cikloalkil(C1-C6)alkilne, skupine C(O)R', R", CO2R" ili C(O)NR10R20,
R' je skupina koju se bira između atoma vodika, (C1-C6)alkilne skupine, (C3-C7)cikloalkilne skupine i (C3-C7)cikloalkil(C1-C6)alkilne skupine,
R" je skupina koju se bira između (C1-C6)alkilne skupine, (C3-C7)cikloalkilne skupine i (C3-C7)cikloalkil(C1-C6)alkilne skupine,
R10 i R20 su, međusobno neovisno, jedna ili više skupina, koje se bira između atoma vodika, (C1-C6)alkilne skupine, (C3-C7)cikloalkilne skupine i (C3-C7)cikloalkil(C1-C6)alkilne skupine, ili R10 i R20 mogu tvoriti zasićeni ili djelomično nezasićeni prsten s 5 do 7 atoma ugljika i izborno sadrži heteroatom, kojeg se bira između O, N ili S(O)m,
m predstavlja 0, 1 ili 2,
u obliku baze ili adicijske soli s kiselinom, a također i u obliku hidrata ili solvata.
2. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što:
X je atom vodika ili halogena,
A je odsutan ili je veza, atom kisika, atom sumpora, skupina NR, C(O)NR' ili NR', (C1-C2)alkilenska skupina ili (C2)alkenilna skupina,
u obliku baze ili adicijske soli s kiselinom, a također i u obliku hidrata ili solvata.
3. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 i 2, naznačen time što:
X je atom vodika ili halogena,
A je odsutan ili je veza ili (C1-C2)alkilenska skupina,
R1 i R2 su, međusobno neovisno, jedna ili više skupina, koje se bira između atoma vodika, atoma halogena, cijano skupine ili alkoksi skupine,
u obliku baze ili adicijske soli s kiselinom, a također i u obliku hidrata ili solvata.
4. Spoj formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 3, naznačen time što:
X je atom vodika ili halogena,
A je odsutan ili je veza ili etilenska skupina,
R1 i R2 su, međusobno neovisno, jedna ili više skupina, koje se bira između atoma vodika ili halogena,
u obliku baze ili adicijske soli s kiselinom, a također i u obliku hidrata ili solvata.
5. Spoj formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što:
X je atom vodika ili klora,
A je odsutan ili je veza ili etilenska skupina,
R1 i R2 su, međusobno neovisno, jedna ili više skupina, koje se bira između atoma vodika, fluorine atom ili atom klora,
u obliku baze ili adicijske soli s kiselinom, a također i u obliku hidrata ili solvata.
6. Spoj formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što ga se bira između:
– (4-benzhidrilpiperazin-1-il)-1,2,3-triazolo[4,5-b]piridin-1-ilmetanona
– (4-benzhidrilpiperazin-1-il)(6-klor-1,2,3-triazolo[4,5-b]piridin-1-il)metanona
– {4-[bis(4-fluorfenil)metil]piperazin-1-il}-1,2,3-triazolo[4,5-b]piridin-1-ilmetanona
– {4-[bis(4-klorfenil)metil]piperazin-1-il}-1,2,3-triazolo[4,5-b]piridin-1-ilmetanona
– {4-[bis(4-fluorfenil)metil]piperazin-1-il}(6-klor-1,2,3-triazolo[4,5-b]piridin-1-il)metanona
– {4-[bis(4-klorfenil)metil]piperazin-1-il}(6-klor-1,2,3-triazolo[4,5-b]piridin-1-il)metanona
– [4-(10,11-dihidro-5H-dibenzo[a,d]ciklohepten-5-il)piperazin-1-il]-1,2,3-triazolo[4,5-b]piridin-1-ilmetanona
– [4-(9H-fluoren-9-il)piperazin-1-il]-1,2,3-triazolo[4,5-b]piridin-1-ilmetanona.
7. Postupak dobivanja spoja formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što spoj formule (II)
[image]
u kojoj X je kao što je definirano u formuli (I), u skladu s patentnim zahtjevom 1, reagira sa spojem formule (III)
[image]
u kojoj A, R1 i R2 su kao što je definirano u formuli (I), u skladu s patentnim zahtjevom 1.
8. Postupak dobivanja spoja formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što spoj formule (IV)
[image]
u kojoj X je kao što je definirano u formuli (I), u skladu s patentnim zahtjevom 1, reagira sa spojem formule (V)
[image]
u kojoj A, R1 i R2 su kao što je definirano u formuli (I), u skladu s patentnim zahtjevom 1, a L predstavlja izlaznu skupinu.
9. Spoj formule (IV)
[image]
naznačen time što X je kao što je definirano u formuli (I), u skladu s patentnim zahtjevom 1.
10. Medikament, naznačen time što sadrži spoj formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 6, ili adicijsku sol navedenog spoja s farmaceutski prihvatljivom kiselinom, ili hidrat ili solvat spoja formule (I).
11. Framaceutski pripravak, naznačen time što sadrži spoj formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 6, ili farmaceutski prihvatljivu sol, hidrat ili solvat navedenog spoja, a također i najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
12. Upotreba spoja formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u liječenju i sprječavanju patološkog stanja u koje su uključeni endogeni 2-arahidonoilglicerol (2-AG) i endogeni 1(3)-arahidonoilglicerol, i/ili bilo koji drugi supstrat kojeg metabolizira enzim MGL.
13. Upotreba spoja formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 6, u obliku farmaceutski prihvatljive baze, hidrata ili solvata, naznačena time što je navedeni spoj namijenjen pripravi medikamenta namijenjenog upotrebi u sprječavanju ili liječenju akutne ili kronične boli, vrtoglavice, povraćanja, mučnine, poremećaja hranjenja, metaboličkog sindroma, dislipidemije, neuroloških i psihičkih patoloških stanja, akutnih ili kroničnih neurodegenerativnih bolesti, epilepsije, poremećaja spavanja, kardiovaskularnih bolesti, ishemije bubrega, raznih oblika raka, poremećaja imunosnog sustava, alergijskih bolesti, parazitskih, virusnih ili bakterijskih zaraznih bolesti, upalnih bolesti, osteoporoze, očnih stanja, plućnih stanja, gastrointestinalnih bolesti, inkontinencije mokraće i upale mokraćnog mjehura.
14. Spoj formule (I), u skladu s bilo kojim od patentnih zahtjeva 1 do 6, u obliku farmaceutski prihvatljive baze, hidrata ili solvata, naznačen time što je namijenjen sprječavanju ili liječenju akutne ili kronične boli, vrtoglavice, povraćanja, mučnine, poremećaja hranjenja, metaboličkog sindroma, dislipidemije, neuroloških i psihičkih patoloških stanja, akutnih ili kroničnih neurodegenerativnih bolesti, epilepsije, poremećaja spavanja, kardiovaskularnih bolesti, ishemije bubrega, raznih oblika raka, poremećaja imunosnog sustava, alergijskih bolesti, parazitskih, virusnih ili bakterijskih zaraznih bolesti, upalnih bolesti, osteoporoze, očnih stanja, plućnih stanja, gastrointestinalnih bolesti, inkontinencije mokraće i upale mokraćnog mjehura.
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FR0702807A FR2915197B1 (fr) | 2007-04-18 | 2007-04-18 | Derives de triazolopyridine-carboxamides, leur preparation et leur application therapeutique. |
PCT/FR2008/000535 WO2008145842A2 (fr) | 2007-04-18 | 2008-04-16 | Dérivés de triazolopyridine-carboxamides, leur préparation et leur application en thérapeutique |
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HRP20100573T1 true HRP20100573T1 (hr) | 2010-11-30 |
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HR20100573T HRP20100573T1 (hr) | 2007-04-18 | 2010-10-19 | Triazolopiridinkarboksamidni derivati, njihovo dobivanje i njihova upotreba u terapiji |
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US (2) | US7868007B2 (hr) |
EP (1) | EP2146991B1 (hr) |
JP (1) | JP2010524907A (hr) |
KR (1) | KR20090130060A (hr) |
CN (1) | CN101657451A (hr) |
AR (1) | AR066103A1 (hr) |
AT (1) | ATE475661T1 (hr) |
AU (1) | AU2008257323A1 (hr) |
BR (1) | BRPI0810430A2 (hr) |
CA (1) | CA2683933A1 (hr) |
CY (1) | CY1111601T1 (hr) |
DE (1) | DE602008001981D1 (hr) |
DK (1) | DK2146991T3 (hr) |
ES (1) | ES2348969T3 (hr) |
FR (1) | FR2915197B1 (hr) |
HR (1) | HRP20100573T1 (hr) |
IL (1) | IL201416A0 (hr) |
MX (1) | MX2009011215A (hr) |
PL (1) | PL2146991T3 (hr) |
PT (1) | PT2146991E (hr) |
RS (1) | RS51462B (hr) |
RU (1) | RU2009142430A (hr) |
SI (1) | SI2146991T1 (hr) |
TW (1) | TW200906401A (hr) |
UY (1) | UY31036A1 (hr) |
WO (1) | WO2008145842A2 (hr) |
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CA2743861A1 (en) * | 2008-11-14 | 2010-05-20 | The Scripps Research Institute | Methods and compositions related to targeting monoacylglycerol lipase |
AU2009330821B2 (en) * | 2008-12-24 | 2015-06-11 | Bial - Portela & Ca, S.A. | Pharmaceutical compounds |
TW201105655A (en) | 2009-04-22 | 2011-02-16 | Janssen Pharmaceutica Nv | Azetidinyl diamides as monoacylglycerol lipase inhibitors |
US8450350B2 (en) * | 2010-05-05 | 2013-05-28 | Infinity Pharmaceuticals, Inc. | Triazoles as inhibitors of fatty acid synthase |
RU2013114771A (ru) | 2010-09-03 | 2014-10-10 | Янссен Фармацевтика Нв | Диамиды азетидинила как ингибиторы моноацилглицерол липазы |
JP2013537920A (ja) | 2010-09-27 | 2013-10-07 | ヤンセン ファーマシューティカ エヌ.ベー. | モノアシルグリセロールリパーゼ阻害剤としてのオキソピペラジン−アゼチジンアミド及びオキソジアゼピン−アゼチジンアミド |
US8575363B2 (en) | 2010-10-22 | 2013-11-05 | Janssen Pharmaceutica N.V. | Amino-pyrrolidine-azetidine diamides as monoacylglycerol lipase inhibitors |
US8513423B2 (en) | 2010-10-22 | 2013-08-20 | Janssen Pharmaceutica, Nv | Piperidin-4-yl-azetidine diamides as monoacylglycerol lipase inhibitors |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
MA53220A (fr) * | 2018-08-13 | 2021-11-17 | Hoffmann La Roche | Nouveaux composés hétérocycliques utilisés en tant qu'inhibiteurs de monoacylglycérol lipase |
RU2769507C1 (ru) * | 2018-08-13 | 2022-04-01 | Ф. Хоффманн-Ля Рош Аг | Новые гетероциклические соединения как ингибиторы моноацилглицеринлипазы |
TW202035409A (zh) | 2018-09-28 | 2020-10-01 | 比利時商健生藥品公司 | 單醯基甘油脂肪酶調節劑 |
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GB0100624D0 (en) * | 2001-01-10 | 2001-02-21 | Vernalis Res Ltd | Chemical compounds VII |
DE10247680B4 (de) * | 2002-10-12 | 2005-09-01 | Aventis Pharma Deutschland Gmbh | Neue bicyclische Inhibitoren der Hormon Sensitiven Lipase |
DE102004005172A1 (de) * | 2004-02-02 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Indazolderivate als Inhibitoren der Hormon Sensitiven Lipase |
US7632837B2 (en) * | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
DE102005049954A1 (de) * | 2005-10-19 | 2007-05-31 | Sanofi-Aventis Deutschland Gmbh | Triazolopyridin-derivate als Inhibitoren von Lipasen und Phospholipasen |
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2007
- 2007-04-18 FR FR0702807A patent/FR2915197B1/fr not_active Expired - Fee Related
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2008
- 2008-04-16 RU RU2009142430/04A patent/RU2009142430A/ru not_active Application Discontinuation
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- 2008-04-16 CA CA002683933A patent/CA2683933A1/fr not_active Abandoned
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- 2008-04-16 WO PCT/FR2008/000535 patent/WO2008145842A2/fr active Application Filing
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Also Published As
Publication number | Publication date |
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US20100035893A1 (en) | 2010-02-11 |
US20110071161A1 (en) | 2011-03-24 |
TW200906401A (en) | 2009-02-16 |
CY1111601T1 (el) | 2015-10-07 |
WO2008145842A3 (fr) | 2009-01-22 |
KR20090130060A (ko) | 2009-12-17 |
UY31036A1 (es) | 2008-11-28 |
PL2146991T3 (pl) | 2011-01-31 |
RU2009142430A (ru) | 2011-05-27 |
SI2146991T1 (sl) | 2010-11-30 |
US7868007B2 (en) | 2011-01-11 |
BRPI0810430A2 (pt) | 2014-10-14 |
MX2009011215A (es) | 2009-11-02 |
DE602008001981D1 (de) | 2010-09-09 |
ES2348969T3 (es) | 2010-12-17 |
RS51462B (en) | 2011-04-30 |
CN101657451A (zh) | 2010-02-24 |
EP2146991A2 (fr) | 2010-01-27 |
DK2146991T3 (da) | 2010-11-22 |
AR066103A1 (es) | 2009-07-22 |
JP2010524907A (ja) | 2010-07-22 |
PT2146991E (pt) | 2010-10-04 |
WO2008145842A2 (fr) | 2008-12-04 |
FR2915197A1 (fr) | 2008-10-24 |
AU2008257323A1 (en) | 2008-12-04 |
EP2146991B1 (fr) | 2010-07-28 |
CA2683933A1 (fr) | 2008-12-04 |
IL201416A0 (en) | 2010-05-31 |
FR2915197B1 (fr) | 2009-06-12 |
ATE475661T1 (de) | 2010-08-15 |
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