JP2005519028A5 - - Google Patents
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- Publication number
- JP2005519028A5 JP2005519028A5 JP2003543594A JP2003543594A JP2005519028A5 JP 2005519028 A5 JP2005519028 A5 JP 2005519028A5 JP 2003543594 A JP2003543594 A JP 2003543594A JP 2003543594 A JP2003543594 A JP 2003543594A JP 2005519028 A5 JP2005519028 A5 JP 2005519028A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- adamantylmethyl
- chloro
- propyl
- isonicotinamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 60
- -1 nitro, amino, hydroxyl Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 230000000414 obstructive effect Effects 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- RJLCIACWXJHILW-UHFFFAOYSA-N pyridine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.NC(=O)C1=CC=NC=C1 RJLCIACWXJHILW-UHFFFAOYSA-N 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- JHGWHCMSMNXEEJ-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-(3-aminopropyl)-5-chloropyridine-4-carboxamide;hydrochloride Chemical compound Cl.C1=NC(CCCN)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl JHGWHCMSMNXEEJ-UHFFFAOYSA-N 0.000 claims 1
- IPQLAOFEUDOUPE-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-[3-[bis(3-hydroxypropyl)amino]propylamino]-3-chloropyridine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.OCCCN(CCCO)CCCNC1=NC=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl IPQLAOFEUDOUPE-UHFFFAOYSA-N 0.000 claims 1
- ONEYPAADQQVFQT-UHFFFAOYSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-(3-hydroxypropylamino)propyl]pyridine-3-carboxamide Chemical compound OCCCNCCCC1=CN=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 ONEYPAADQQVFQT-UHFFFAOYSA-N 0.000 claims 1
- DCQWLQWQYYTWQU-MBAYWBQQSA-N n-(1-adamantylmethyl)-2-chloro-5-[3-[[(2r)-1-hydroxypropan-2-yl]amino]propyl]pyridine-3-carboxamide Chemical compound OC[C@@H](C)NCCCC1=CN=C(Cl)C(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1 DCQWLQWQYYTWQU-MBAYWBQQSA-N 0.000 claims 1
- XXKBRVBIJWCJPT-IIFATDLDSA-N n-(1-adamantylmethyl)-5-bromo-2-[(2s)-2-hydroxy-3-(methylamino)propoxy]pyridine-4-carboxamide Chemical compound C1=NC(OC[C@@H](O)CNC)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Br XXKBRVBIJWCJPT-IIFATDLDSA-N 0.000 claims 1
- ONILJCUURVXQEY-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-[2-(2-hydroxyethylamino)ethylamino]pyridine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1=NC(NCCNCCO)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl ONILJCUURVXQEY-UHFFFAOYSA-N 0.000 claims 1
- LMACPPZMORVSQL-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-[3-(3-hydroxypropylamino)propyl]pyridine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1=NC(CCCNCCCO)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl LMACPPZMORVSQL-UHFFFAOYSA-N 0.000 claims 1
- QIWSGQKNGVPGDB-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-[3-(ethylamino)propyl]pyridine-4-carboxamide;hydrochloride Chemical compound Cl.C1=NC(CCCNCC)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl QIWSGQKNGVPGDB-UHFFFAOYSA-N 0.000 claims 1
- ZCKLJWHUYAVEDF-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-[3-(methylamino)propyl]pyridine-4-carboxamide;hydrochloride Chemical compound Cl.C1=NC(CCCNC)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl ZCKLJWHUYAVEDF-UHFFFAOYSA-N 0.000 claims 1
- XXXFACQYNDFSPA-UHFFFAOYSA-N n-(1-adamantylmethyl)-5-chloro-2-[[3-(methylamino)propylamino]methyl]pyridine-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1=NC(CNCCCNC)=CC(C(=O)NCC23CC4CC(CC(C4)C2)C3)=C1Cl XXXFACQYNDFSPA-UHFFFAOYSA-N 0.000 claims 1
- UDHZYEWSTDYKCZ-UHFFFAOYSA-N pyridine-4-carboxamide;hydrochloride Chemical compound Cl.NC(=O)C1=CC=NC=C1 UDHZYEWSTDYKCZ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 6
- 0 *c1cnc(*)c(*)c1* Chemical compound *c1cnc(*)c(*)c1* 0.000 description 5
- 238000006268 reductive amination reaction Methods 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 1
- HJNHUFQGDJLQRS-UHFFFAOYSA-N 2-(3-bromopropoxy)oxane Chemical compound BrCCCOC1CCCCO1 HJNHUFQGDJLQRS-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012434 Dermatitis allergic Diseases 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000003435 Optic Neuritis Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 206010039705 Scleritis Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- ZBQUMMFUJLOTQC-UHFFFAOYSA-L dichloronickel;3-diphenylphosphanylpropyl(diphenyl)phosphane Chemical compound Cl[Ni]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 ZBQUMMFUJLOTQC-UHFFFAOYSA-L 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 201000010666 keratoconjunctivitis Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 210000003786 sclera Anatomy 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0103836A SE0103836D0 (sv) | 2001-11-16 | 2001-11-16 | Novel compounds |
| PCT/SE2002/002057 WO2003041707A1 (en) | 2001-11-16 | 2002-11-12 | N-adamantylmethyl derivates and intermediates as pharmaceutical compositions and processes for their preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005519028A JP2005519028A (ja) | 2005-06-30 |
| JP2005519028A5 true JP2005519028A5 (enExample) | 2009-12-24 |
| JP4559077B2 JP4559077B2 (ja) | 2010-10-06 |
Family
ID=20286020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003543594A Expired - Fee Related JP4559077B2 (ja) | 2001-11-16 | 2002-11-12 | 医薬組成物としてのｎ−アダマンチルメチル誘導体および中間体、ならびにそれらの製造方法 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US7129246B2 (enExample) |
| EP (1) | EP1448195B1 (enExample) |
| JP (1) | JP4559077B2 (enExample) |
| KR (1) | KR20040058290A (enExample) |
| CN (1) | CN1585640B (enExample) |
| AR (1) | AR037534A1 (enExample) |
| AT (1) | ATE344034T1 (enExample) |
| AU (1) | AU2002347741B2 (enExample) |
| BR (1) | BR0214142A (enExample) |
| CA (1) | CA2464863A1 (enExample) |
| CO (1) | CO5580747A2 (enExample) |
| DE (1) | DE60215851T2 (enExample) |
| DK (1) | DK1448195T3 (enExample) |
| ES (1) | ES2274110T3 (enExample) |
| HU (1) | HUP0402560A3 (enExample) |
| IL (1) | IL161693A0 (enExample) |
| IS (1) | IS7261A (enExample) |
| MX (1) | MXPA04004498A (enExample) |
| MY (1) | MY136430A (enExample) |
| NO (1) | NO20042155L (enExample) |
| NZ (1) | NZ532755A (enExample) |
| PL (1) | PL370855A1 (enExample) |
| PT (1) | PT1448195E (enExample) |
| RU (1) | RU2300525C2 (enExample) |
| SE (1) | SE0103836D0 (enExample) |
| TW (1) | TW200407297A (enExample) |
| UA (1) | UA77978C2 (enExample) |
| WO (1) | WO2003041707A1 (enExample) |
| ZA (1) | ZA200403682B (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI258462B (en) * | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
| SE0200920D0 (sv) * | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
| SE0300480D0 (sv) * | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| EP1644042A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
| EP1644041A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| JP2007501270A (ja) * | 2003-05-29 | 2007-01-25 | アストラゼネカ・アクチエボラーグ | Ｐ２Ｘ７受容体アンタゴニストおよび腫瘍壊死因子αを含む医薬組成物 |
| GB0312609D0 (en) * | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| KR100554155B1 (ko) * | 2003-06-09 | 2006-02-22 | 학교법인 포항공과대학교 | 금속/반도체 나노막대 이종구조를 이용한 전극 구조물 및그 제조 방법 |
| SE0302139D0 (sv) * | 2003-07-28 | 2003-07-28 | Astrazeneca Ab | Novel compounds |
| SE0302192D0 (sv) * | 2003-08-08 | 2003-08-08 | Astrazeneca Ab | Novel compounds |
| SE0302488D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
| SA05260265A (ar) * | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
| SE0402925D0 (sv) * | 2004-11-30 | 2004-11-30 | Astrazeneca Ab | Novel Compounds |
| KR20090094336A (ko) | 2006-11-27 | 2009-09-04 | 하. 룬트벡 아크티에 셀스카브 | 헤테로아릴 아미드 유도체 |
| PE20091225A1 (es) * | 2007-03-22 | 2009-09-16 | Astrazeneca Ab | Derivados de quinolina como antagonistas del receptor p2x7 |
| CA2682925A1 (en) | 2007-04-10 | 2008-10-16 | David C. Ihle | Heteroaryl amide analogues |
| PE20091036A1 (es) | 2007-11-30 | 2009-08-15 | Astrazeneca Ab | Derivado de quinolina como antagonista del receptor p2x7 |
| EP2105164B1 (en) | 2008-03-25 | 2011-01-12 | Affectis Pharmaceuticals AG | Novel P2X7R antagonists and their use |
| ATE541832T1 (de) | 2009-04-14 | 2012-02-15 | Affectis Pharmaceuticals Ag | Neuartige p2x7r-antagonisten und ihre verwendung |
| EP2386541A1 (en) | 2010-05-14 | 2011-11-16 | Affectis Pharmaceuticals AG | Novel methods for the preparation of P2X7R antagonists |
| WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
| MX2014000894A (es) | 2011-07-22 | 2014-02-27 | Actelion Pharmaceuticals Ltd | Derivados de amidas heterociclicas como antagonistas de receptores p2x7. |
| BR112014017735B1 (pt) | 2012-01-20 | 2022-06-28 | Idorsia Pharmaceuticals Ltd | Compostos derivados de amida heterocíclicos como antagonistas do receptor de p2x7, composição farmacêutica, e, uso de um composto |
| KR101576235B1 (ko) * | 2012-11-30 | 2015-12-11 | 한국생명공학연구원 | 신규한 이치환 아다만틸 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 암 전이 억제용 약학적 조성물 |
| EP2931717B1 (en) | 2012-12-12 | 2016-12-07 | Actelion Pharmaceuticals Ltd. | Indole carboxamide derivatives as p2x7 receptor antagonists |
| CA2891499C (en) | 2012-12-18 | 2021-07-06 | Actelion Pharmaceuticals Ltd | Indole carboxamide derivatives as p2x7 receptor antagonists |
| CN104918617B (zh) | 2013-01-22 | 2017-05-10 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
| JP6282017B2 (ja) | 2013-01-22 | 2018-02-21 | イドーシア ファーマシューティカルズ リミテッドＩｄｏｒｓｉａ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｐ２ｘ７受容体アンタゴニストとしての複素環アミド誘導体 |
| CN104163795B (zh) * | 2014-08-19 | 2016-02-03 | 四川大学 | 盐酸烟酰美金刚胺溶剂合物、其制备方法和用途 |
| CN104628617B (zh) * | 2015-02-12 | 2016-04-06 | 佛山市赛维斯医药科技有限公司 | N-金刚烷酰胺类葡萄糖激酶活化剂、制备方法及其用途 |
| CN104628615B (zh) * | 2015-02-12 | 2016-04-06 | 佛山市赛维斯医药科技有限公司 | 含卤代苯的n-金刚烷酰胺类化合物、其制备方法及其用途 |
| CN104693084B (zh) * | 2015-02-12 | 2016-03-16 | 佛山市赛维斯医药科技有限公司 | 含腈基苯基的n-金刚烷酰胺类化合物、其制备方法及用途 |
| CN104628616B (zh) * | 2015-02-12 | 2016-06-01 | 佛山市赛维斯医药科技有限公司 | 含对硝基苯基的n-金刚烷酰胺类化合物、其制备方法及用途 |
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| US3352912A (en) | 1963-07-24 | 1967-11-14 | Du Pont | Adamantanes and tricyclo[4. 3. 1. 1 3.8] undecanes |
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| US3464998A (en) * | 1968-03-04 | 1969-09-02 | Searle & Co | Adamantyl esters and amides of pyridinecarboxylic acids |
| GB1274652A (en) | 1968-08-27 | 1972-05-17 | Lilly Industries Ltd | Adamantanyl-alkylamine derivatives and their preparation |
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| US4751292A (en) * | 1985-07-02 | 1988-06-14 | The Plant Cell Research Institute, Inc. | Adamantyl purines |
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| SE9704545D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| SE9704544D0 (sv) * | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
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| GB0013737D0 (en) | 2000-06-07 | 2000-07-26 | Astrazeneca Ab | Novel compounds |
| SE0200920D0 (sv) | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
-
2001
- 2001-11-16 SE SE0103836A patent/SE0103836D0/xx unknown
-
2002
- 2002-11-07 TW TW091132764A patent/TW200407297A/zh unknown
- 2002-11-12 WO PCT/SE2002/002057 patent/WO2003041707A1/en not_active Ceased
- 2002-11-12 CA CA002464863A patent/CA2464863A1/en not_active Abandoned
- 2002-11-12 KR KR10-2004-7007397A patent/KR20040058290A/ko not_active Ceased
- 2002-11-12 PT PT02783941T patent/PT1448195E/pt unknown
- 2002-11-12 AU AU2002347741A patent/AU2002347741B2/en not_active Ceased
- 2002-11-12 EP EP02783941A patent/EP1448195B1/en not_active Expired - Lifetime
- 2002-11-12 AT AT02783941T patent/ATE344034T1/de not_active IP Right Cessation
- 2002-11-12 JP JP2003543594A patent/JP4559077B2/ja not_active Expired - Fee Related
- 2002-11-12 BR BR0214142-6A patent/BR0214142A/pt not_active IP Right Cessation
- 2002-11-12 CN CN028225171A patent/CN1585640B/zh not_active Expired - Fee Related
- 2002-11-12 PL PL02370855A patent/PL370855A1/xx not_active Application Discontinuation
- 2002-11-12 DE DE60215851T patent/DE60215851T2/de not_active Expired - Lifetime
- 2002-11-12 DK DK02783941T patent/DK1448195T3/da active
- 2002-11-12 MX MXPA04004498A patent/MXPA04004498A/es active IP Right Grant
- 2002-11-12 ES ES02783941T patent/ES2274110T3/es not_active Expired - Lifetime
- 2002-11-12 RU RU2004112780/04A patent/RU2300525C2/ru not_active IP Right Cessation
- 2002-11-12 NZ NZ532755A patent/NZ532755A/en unknown
- 2002-11-12 IL IL16169302A patent/IL161693A0/xx unknown
- 2002-11-12 US US10/495,711 patent/US7129246B2/en not_active Expired - Fee Related
- 2002-11-12 HU HU0402560A patent/HUP0402560A3/hu unknown
- 2002-11-14 MY MYPI20024270A patent/MY136430A/en unknown
- 2002-11-15 AR ARP020104406A patent/AR037534A1/es unknown
- 2002-12-11 UA UA20040503316A patent/UA77978C2/uk unknown
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2004
- 2004-05-11 CO CO04043373A patent/CO5580747A2/es not_active Application Discontinuation
- 2004-05-13 IS IS7261A patent/IS7261A/is unknown
- 2004-05-13 ZA ZA200403682A patent/ZA200403682B/xx unknown
- 2004-05-25 NO NO20042155A patent/NO20042155L/no not_active Application Discontinuation
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