NO329134B1 - Aminoalkoholderivater eller fosfonsyrederivater og farmasoytiske preparater som inneholder disse og som kan anvendes ved profylakse eller behandling av autoimmunsykdommer - Google Patents
Aminoalkoholderivater eller fosfonsyrederivater og farmasoytiske preparater som inneholder disse og som kan anvendes ved profylakse eller behandling av autoimmunsykdommer Download PDFInfo
- Publication number
- NO329134B1 NO329134B1 NO20043319A NO20043319A NO329134B1 NO 329134 B1 NO329134 B1 NO 329134B1 NO 20043319 A NO20043319 A NO 20043319A NO 20043319 A NO20043319 A NO 20043319A NO 329134 B1 NO329134 B1 NO 329134B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- amino
- formula
- group
- pyrrol
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims description 39
- 208000023275 Autoimmune disease Diseases 0.000 title claims description 23
- 238000011321 prophylaxis Methods 0.000 title claims description 5
- 150000001414 amino alcohols Chemical class 0.000 title description 6
- 229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 title description 6
- 150000003007 phosphonic acid derivatives Chemical class 0.000 title description 6
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 798
- 150000003839 salts Chemical class 0.000 claims description 104
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 69
- 150000002148 esters Chemical class 0.000 claims description 63
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 10
- CKVICYBZYGZLLP-UHFFFAOYSA-N pentylphosphonic acid Chemical compound CCCCCP(O)(O)=O CKVICYBZYGZLLP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 9
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 6
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 201000008937 atopic dermatitis Diseases 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 210000000056 organ Anatomy 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 238000002054 transplantation Methods 0.000 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
- XSUONWDGNBHCSF-UHFFFAOYSA-N 2-amino-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-2-methylbutan-1-ol Chemical compound O1C(CCC(N)(CO)C)=CC=C1C#CCCOC1CCCCC1 XSUONWDGNBHCSF-UHFFFAOYSA-N 0.000 claims description 5
- HFNSJBPYALQTRC-UHFFFAOYSA-N 2-amino-4-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]-2-methylbutan-1-ol Chemical compound O1C(CCC(N)(CO)C)=CC=C1C#CCCCC1CCCCC1 HFNSJBPYALQTRC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 5
- KRSANPACYLQJBN-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)furan-2-yl]-5-cyclohexylpentan-1-one Chemical compound O1C(CCC(N)(CO)C)=CC=C1C(=O)CCCCC1CCCCC1 KRSANPACYLQJBN-UHFFFAOYSA-N 0.000 claims description 4
- YINUDBJUICEECU-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(5-phenylpent-1-ynyl)furan-2-yl]butan-1-ol Chemical compound O1C(CCC(N)(CO)C)=CC=C1C#CCCCC1=CC=CC=C1 YINUDBJUICEECU-UHFFFAOYSA-N 0.000 claims description 4
- RFMUDEZQQGSWKQ-UHFFFAOYSA-N C1=C(C)C(C)=CC=C1OCC#CC1=CC=C(CCC(C)(N)COP(O)(O)=O)O1 Chemical compound C1=C(C)C(C)=CC=C1OCC#CC1=CC=C(CCC(C)(N)COP(O)(O)=O)O1 RFMUDEZQQGSWKQ-UHFFFAOYSA-N 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
- CTKQLZCZMPGEON-UHFFFAOYSA-N O1C(CCC(N)(C)COP(O)(O)=O)=CC=C1C#CCCCC1=CC=CC=C1 Chemical compound O1C(CCC(N)(C)COP(O)(O)=O)=CC=C1C#CCCCC1=CC=CC=C1 CTKQLZCZMPGEON-UHFFFAOYSA-N 0.000 claims description 4
- SPYPEROZFJYQEJ-UHFFFAOYSA-N O1C(CCC(N)(C)COP(O)(O)=O)=CC=C1C#CCCCC1CCCCC1 Chemical compound O1C(CCC(N)(C)COP(O)(O)=O)=CC=C1C#CCCCC1CCCCC1 SPYPEROZFJYQEJ-UHFFFAOYSA-N 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- BWXNEIZLWYJCLY-UHFFFAOYSA-N [2-amino-4-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound O1C(CCC(N)(C)COP(O)(O)=O)=CC=C1C#CCCOC1CCCCC1 BWXNEIZLWYJCLY-UHFFFAOYSA-N 0.000 claims description 4
- WZPAAQWEEASXHJ-UHFFFAOYSA-N [3-amino-3-methyl-5-[5-(5-phenylpent-1-ynyl)furan-2-yl]pentyl]phosphonic acid Chemical compound O1C(CCC(N)(C)CCP(O)(O)=O)=CC=C1C#CCCCC1=CC=CC=C1 WZPAAQWEEASXHJ-UHFFFAOYSA-N 0.000 claims description 4
- XJMFESYVDHRIQM-UHFFFAOYSA-N [3-amino-5-[5-(4-cyclohexyloxybut-1-ynyl)furan-2-yl]-3-methylpentyl]phosphonic acid Chemical compound O1C(CCC(N)(C)CCP(O)(O)=O)=CC=C1C#CCCOC1CCCCC1 XJMFESYVDHRIQM-UHFFFAOYSA-N 0.000 claims description 4
- AYYDYHRQKOTABD-UHFFFAOYSA-N [3-amino-5-[5-(5-cyclohexylpent-1-ynyl)furan-2-yl]-3-methylpentyl]phosphonic acid Chemical compound O1C(CCC(N)(C)CCP(O)(O)=O)=CC=C1C#CCCCC1CCCCC1 AYYDYHRQKOTABD-UHFFFAOYSA-N 0.000 claims description 4
- BIYRCJYVMUOGOY-UHFFFAOYSA-N [3-amino-5-[5-(5-cyclohexylpentanoyl)furan-2-yl]-3-methylpentyl]phosphonic acid Chemical compound O1C(CCC(N)(C)CCP(O)(O)=O)=CC=C1C(=O)CCCCC1CCCCC1 BIYRCJYVMUOGOY-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims description 4
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 3
- IQYLJXJRPZPFGD-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-ethylpyrrol-2-yl]-4-cyclohexylbutan-1-one Chemical compound CCN1C(CCC(C)(N)CO)=CC=C1C(=O)CCCC1CCCCC1 IQYLJXJRPZPFGD-UHFFFAOYSA-N 0.000 claims description 3
- NOMZOSRBMJOROA-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-methylpyrrol-2-yl]-4-cyclohexylbutan-1-one Chemical compound CN1C(CCC(C)(N)CO)=CC=C1C(=O)CCCC1CCCCC1 NOMZOSRBMJOROA-UHFFFAOYSA-N 0.000 claims description 3
- YSWQIILRANCRAZ-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-methylpyrrol-2-yl]-4-phenylbutan-1-one Chemical compound CN1C(CCC(C)(N)CO)=CC=C1C(=O)CCCC1=CC=CC=C1 YSWQIILRANCRAZ-UHFFFAOYSA-N 0.000 claims description 3
- SCIWGLZQALHDNR-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-methylpyrrol-2-yl]-5-cyclohexylpentan-1-one Chemical compound CN1C(CCC(C)(N)CO)=CC=C1C(=O)CCCCC1CCCCC1 SCIWGLZQALHDNR-UHFFFAOYSA-N 0.000 claims description 3
- RGPCTDIAUSOBKO-UHFFFAOYSA-N 2-amino-4-[5-[3-(3,4-dimethylphenoxy)prop-1-ynyl]furan-2-yl]-2-methylbutan-1-ol Chemical compound C1=C(C)C(C)=CC=C1OCC#CC1=CC=C(CCC(C)(N)CO)O1 RGPCTDIAUSOBKO-UHFFFAOYSA-N 0.000 claims description 3
- KWTGFDRRDWABRW-UHFFFAOYSA-N CN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C#CCCOC1CCCCC1 Chemical compound CN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C#CCCOC1CCCCC1 KWTGFDRRDWABRW-UHFFFAOYSA-N 0.000 claims description 3
- OMWADJIYTIYPDT-UHFFFAOYSA-N [2-amino-4-[1-ethyl-5-(4-phenylbutanoyl)pyrrol-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound CCN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCC1=CC=CC=C1 OMWADJIYTIYPDT-UHFFFAOYSA-N 0.000 claims description 3
- NZQOBIHVISVMIY-UHFFFAOYSA-N [2-amino-4-[5-(4-cyclohexylbutanoyl)-1-ethylpyrrol-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound CCN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCC1CCCCC1 NZQOBIHVISVMIY-UHFFFAOYSA-N 0.000 claims description 3
- JXUSTBUFEILAEL-UHFFFAOYSA-N [2-amino-4-[5-(4-cyclohexylbutanoyl)-1-methylpyrrol-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound CN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCC1CCCCC1 JXUSTBUFEILAEL-UHFFFAOYSA-N 0.000 claims description 3
- LOHBJKBSWMYCNP-UHFFFAOYSA-N [2-amino-4-[5-(5-cyclohexylpentanoyl)-1-ethylpyrrol-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound CCN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCCC1CCCCC1 LOHBJKBSWMYCNP-UHFFFAOYSA-N 0.000 claims description 3
- LJXJMDMROBSFMA-UHFFFAOYSA-N [2-amino-4-[5-(5-cyclohexylpentanoyl)furan-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound O1C(CCC(N)(C)COP(O)(O)=O)=CC=C1C(=O)CCCCC1CCCCC1 LJXJMDMROBSFMA-UHFFFAOYSA-N 0.000 claims description 3
- PSWWEYXIXBJHSG-UHFFFAOYSA-N [3-amino-3-methyl-5-[1-methyl-5-(4-phenylbutanoyl)pyrrol-2-yl]pentyl]phosphonic acid Chemical compound CN1C(CCC(C)(N)CCP(O)(O)=O)=CC=C1C(=O)CCCC1=CC=CC=C1 PSWWEYXIXBJHSG-UHFFFAOYSA-N 0.000 claims description 3
- QLJBZKAQHJDGCF-UHFFFAOYSA-N [3-amino-5-[5-(4-cyclohexylbutanoyl)-1-methylpyrrol-2-yl]-3-methylpentyl]phosphonic acid Chemical compound CN1C(CCC(C)(N)CCP(O)(O)=O)=CC=C1C(=O)CCCC1CCCCC1 QLJBZKAQHJDGCF-UHFFFAOYSA-N 0.000 claims description 3
- QVEUUYUKOGPAMF-UHFFFAOYSA-N [3-amino-5-[5-(4-cyclohexyloxybut-1-ynyl)-1-methylpyrrol-2-yl]-3-methylpentyl]phosphonic acid Chemical compound CN1C(CCC(C)(N)CCP(O)(O)=O)=CC=C1C#CCCOC1CCCCC1 QVEUUYUKOGPAMF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- UZXBDQKFCRAXIG-UHFFFAOYSA-N 2-amino-2-methyl-4-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]butan-1-ol Chemical compound CN1C(CCC(C)(N)CO)=CC=C1C#CCCCC1=CC=CC=C1 UZXBDQKFCRAXIG-UHFFFAOYSA-N 0.000 claims description 2
- AJPNYPKIEGHRPI-UHFFFAOYSA-N 2-amino-2-methyl-4-[5-(5-phenylpentyl)furan-2-yl]butan-1-ol Chemical compound O1C(CCC(N)(CO)C)=CC=C1CCCCCC1=CC=CC=C1 AJPNYPKIEGHRPI-UHFFFAOYSA-N 0.000 claims description 2
- NKPONDKLRKIRRH-UHFFFAOYSA-N CN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCC1=CC=CC=C1 Chemical compound CN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCC1=CC=CC=C1 NKPONDKLRKIRRH-UHFFFAOYSA-N 0.000 claims description 2
- WZXVNFNGSUTDFW-UHFFFAOYSA-N CN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCCC1CCCCC1 Chemical compound CN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCCC1CCCCC1 WZXVNFNGSUTDFW-UHFFFAOYSA-N 0.000 claims description 2
- DFPKSWWHZNTSNG-UHFFFAOYSA-N [2-amino-4-[1-ethyl-5-(5-phenylpentanoyl)pyrrol-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound CCN1C(CCC(C)(N)COP(O)(O)=O)=CC=C1C(=O)CCCCC1=CC=CC=C1 DFPKSWWHZNTSNG-UHFFFAOYSA-N 0.000 claims description 2
- CZAAAFGSSWLWQV-UHFFFAOYSA-N [3-amino-3-methyl-5-[1-methyl-5-(5-phenylpent-1-ynyl)pyrrol-2-yl]pentyl]phosphonic acid Chemical compound CN1C(CCC(C)(N)CCP(O)(O)=O)=CC=C1C#CCCCC1=CC=CC=C1 CZAAAFGSSWLWQV-UHFFFAOYSA-N 0.000 claims description 2
- FRWXAMAKSRSHFF-UHFFFAOYSA-N [3-amino-3-methyl-5-[5-(5-phenylpentyl)furan-2-yl]pentyl]phosphonic acid Chemical compound O1C(CCC(N)(C)CCP(O)(O)=O)=CC=C1CCCCCC1=CC=CC=C1 FRWXAMAKSRSHFF-UHFFFAOYSA-N 0.000 claims description 2
- XQQFXAUAUCPKCA-UHFFFAOYSA-N [3-amino-5-[5-(4-cyclohexylbutanoyl)-1-ethylpyrrol-2-yl]-3-methylpentyl]phosphonic acid Chemical compound CCN1C(CCC(C)(N)CCP(O)(O)=O)=CC=C1C(=O)CCCC1CCCCC1 XQQFXAUAUCPKCA-UHFFFAOYSA-N 0.000 claims description 2
- GQVHPZGEZKXDNK-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-methylpyrrol-2-yl]-4-(3,4-dimethylphenyl)butan-1-one Chemical compound C1=C(C)C(C)=CC=C1CCCC(=O)C1=CC=C(CCC(C)(N)CO)N1C GQVHPZGEZKXDNK-UHFFFAOYSA-N 0.000 claims 1
- YHDBGRYRVKXGDB-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-methylpyrrol-2-yl]-4-(4-methoxyphenyl)butan-1-one Chemical compound C1=CC(OC)=CC=C1CCCC(=O)C1=CC=C(CCC(C)(N)CO)N1C YHDBGRYRVKXGDB-UHFFFAOYSA-N 0.000 claims 1
- YXEQXPNSBUIRDZ-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-methylpyrrol-2-yl]-4-(4-methylphenyl)butan-1-one Chemical compound C1=CC(C)=CC=C1CCCC(=O)C1=CC=C(CCC(C)(N)CO)N1C YXEQXPNSBUIRDZ-UHFFFAOYSA-N 0.000 claims 1
- IDDHUBKPRBPGDD-UHFFFAOYSA-N 1-[5-(3-amino-4-hydroxy-3-methylbutyl)-1-methylpyrrol-2-yl]-4-[4-(trifluoromethyl)phenyl]butan-1-one Chemical compound CN1C(CCC(C)(N)CO)=CC=C1C(=O)CCCC1=CC=C(C(F)(F)F)C=C1 IDDHUBKPRBPGDD-UHFFFAOYSA-N 0.000 claims 1
- WDAKXHNSFCHGEA-UHFFFAOYSA-N 2-amino-2-methyl-4-[1-methyl-5-[4-(3-methylphenyl)butyl]pyrrol-2-yl]butan-1-ol Chemical compound CC1=CC=CC(CCCCC=2N(C(CCC(C)(N)CO)=CC=2)C)=C1 WDAKXHNSFCHGEA-UHFFFAOYSA-N 0.000 claims 1
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- UMOJIOKNXKVYOQ-UHFFFAOYSA-N [2-amino-4-[5-[4-(3,4-dimethylphenyl)butanoyl]-1-methylpyrrol-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound C1=C(C)C(C)=CC=C1CCCC(=O)C1=CC=C(CCC(C)(N)COP(O)(O)=O)N1C UMOJIOKNXKVYOQ-UHFFFAOYSA-N 0.000 claims 1
- AFJONWJMTLDJQI-UHFFFAOYSA-N [2-amino-4-[5-[4-(3,5-dimethylphenyl)butanoyl]-1-methylpyrrol-2-yl]-2-methylbutyl] dihydrogen phosphate Chemical compound CC1=CC(C)=CC(CCCC(=O)C=2N(C(CCC(C)(N)COP(O)(O)=O)=CC=2)C)=C1 AFJONWJMTLDJQI-UHFFFAOYSA-N 0.000 claims 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical class OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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PCT/JP2003/000136 WO2003059880A1 (fr) | 2002-01-11 | 2003-01-09 | Derive d'amino-alcool ou derive d'acide phosphonique et composition medicamenteuse les contenant |
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ATE435202T1 (de) * | 2002-01-11 | 2009-07-15 | Daiichi Sankyo Co Ltd | Aminoalkoholderivat oder phosphonsäurederivat und diese enthaltende medizinische zusammensetzung |
JP4771511B2 (ja) * | 2003-07-08 | 2011-09-14 | 第一三共株式会社 | アミノアルコ−ル誘導体又はホスホン酸誘導体を含有する医薬組成物 |
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TW200510300A (en) * | 2003-07-11 | 2005-03-16 | Sankyo Co | Amino alcohol compounds |
US20070037894A1 (en) * | 2003-09-19 | 2007-02-15 | Hahnfeld Jerry L | Multifunctional menomers and polyarylene compsotions therefrom |
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- 2003-01-09 DK DK03701048T patent/DK1471054T3/da active
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- 2003-01-09 RU RU2004121143/04A patent/RU2330839C2/ru not_active IP Right Cessation
- 2003-01-09 ES ES03701048T patent/ES2327825T3/es not_active Expired - Lifetime
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- 2003-01-09 PT PT03701048T patent/PT1471054E/pt unknown
- 2003-01-09 PL PL370790A patent/PL211954B1/pl unknown
- 2003-01-09 KR KR1020047010719A patent/KR100836547B1/ko not_active IP Right Cessation
- 2003-01-09 KR KR1020087006865A patent/KR20080035702A/ko not_active Application Discontinuation
- 2003-01-09 NZ NZ533994A patent/NZ533994A/xx not_active IP Right Cessation
- 2003-01-09 MX MXPA04006709A patent/MXPA04006709A/es active IP Right Grant
- 2003-01-09 BR BR0306811-0A patent/BR0306811A/pt active Pending
- 2003-01-09 CN CNB038059258A patent/CN100406437C/zh not_active Expired - Fee Related
- 2003-01-09 EP EP03701048A patent/EP1471054B1/en not_active Expired - Lifetime
- 2003-01-10 TW TW092100460A patent/TWI283574B/zh not_active IP Right Cessation
- 2003-01-10 JP JP2003004599A patent/JP4270541B2/ja not_active Expired - Fee Related
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2004
- 2004-07-12 CO CO04065919A patent/CO5640126A2/es active IP Right Grant
- 2004-07-12 US US10/889,657 patent/US7199150B2/en not_active Expired - Fee Related
- 2004-08-10 NO NO20043319A patent/NO329134B1/no not_active IP Right Cessation
- 2004-08-10 ZA ZA2004/06333A patent/ZA200406333B/en unknown
- 2004-11-30 HK HK04109418.1A patent/HK1066532A1/xx not_active IP Right Cessation
-
2006
- 2006-12-11 US US11/636,776 patent/US20070105933A1/en not_active Abandoned
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2007
- 2007-01-09 US US11/651,205 patent/US7638551B2/en not_active Expired - Fee Related
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2009
- 2009-07-24 US US12/460,884 patent/US8067396B2/en not_active Expired - Fee Related
- 2009-08-12 US US12/583,001 patent/US8101650B2/en not_active Expired - Fee Related
- 2009-09-30 CY CY20091101015T patent/CY1109457T1/el unknown
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