JP2009538359A5 - - Google Patents
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- JP2009538359A5 JP2009538359A5 JP2009513381A JP2009513381A JP2009538359A5 JP 2009538359 A5 JP2009538359 A5 JP 2009538359A5 JP 2009513381 A JP2009513381 A JP 2009513381A JP 2009513381 A JP2009513381 A JP 2009513381A JP 2009538359 A5 JP2009538359 A5 JP 2009538359A5
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- JP
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- Prior art keywords
- pain
- enantiomer
- compound
- group
- mixture
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 40
- 239000000203 mixture Substances 0.000 claims 31
- 239000008194 pharmaceutical composition Substances 0.000 claims 20
- 208000002193 Pain Diseases 0.000 claims 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 18
- 208000024891 symptom Diseases 0.000 claims 13
- 208000008035 Back Pain Diseases 0.000 claims 12
- 208000008930 Low Back Pain Diseases 0.000 claims 12
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims 12
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims 12
- 230000001154 acute effect Effects 0.000 claims 12
- 208000035475 disorder Diseases 0.000 claims 12
- 210000003205 muscle Anatomy 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 10
- 229910052805 deuterium Inorganic materials 0.000 claims 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 9
- 229940002612 prodrug Drugs 0.000 claims 9
- 239000000651 prodrug Substances 0.000 claims 9
- 241000124008 Mammalia Species 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 208000024827 Alzheimer disease Diseases 0.000 claims 6
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 6
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 6
- 206010006811 Bursitis Diseases 0.000 claims 6
- 208000034656 Contusions Diseases 0.000 claims 6
- 201000003883 Cystic fibrosis Diseases 0.000 claims 6
- 102000018832 Cytochromes Human genes 0.000 claims 6
- 108010052832 Cytochromes Proteins 0.000 claims 6
- 206010012289 Dementia Diseases 0.000 claims 6
- 208000005171 Dysmenorrhea Diseases 0.000 claims 6
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 6
- 206010019233 Headaches Diseases 0.000 claims 6
- 206010024453 Ligament sprain Diseases 0.000 claims 6
- 208000019695 Migraine disease Diseases 0.000 claims 6
- 208000000112 Myalgia Diseases 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 206010068319 Oropharyngeal pain Diseases 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 6
- 102000001708 Protein Isoforms Human genes 0.000 claims 6
- 108010029485 Protein Isoforms Proteins 0.000 claims 6
- 208000008765 Sciatica Diseases 0.000 claims 6
- 208000026137 Soft tissue injury Diseases 0.000 claims 6
- 208000010040 Sprains and Strains Diseases 0.000 claims 6
- 208000000491 Tendinopathy Diseases 0.000 claims 6
- 206010043255 Tendonitis Diseases 0.000 claims 6
- 208000002240 Tennis Elbow Diseases 0.000 claims 6
- 230000000202 analgesic effect Effects 0.000 claims 6
- 230000001754 anti-pyretic effect Effects 0.000 claims 6
- 239000002221 antipyretic Substances 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 230000009519 contusion Effects 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 231100000869 headache Toxicity 0.000 claims 6
- 208000014674 injury Diseases 0.000 claims 6
- 206010027599 migraine Diseases 0.000 claims 6
- 208000013465 muscle pain Diseases 0.000 claims 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 6
- 230000031990 negative regulation of inflammatory response Effects 0.000 claims 6
- 201000008482 osteoarthritis Diseases 0.000 claims 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 201000004415 tendinitis Diseases 0.000 claims 6
- 208000023409 throat pain Diseases 0.000 claims 6
- 208000004371 toothache Diseases 0.000 claims 6
- 230000008733 trauma Effects 0.000 claims 6
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 claims 4
- 108010026925 Cytochrome P-450 CYP2C19 Proteins 0.000 claims 4
- 108010000561 Cytochrome P-450 CYP2C8 Proteins 0.000 claims 4
- 108010000543 Cytochrome P-450 CYP2C9 Proteins 0.000 claims 4
- 108010001237 Cytochrome P-450 CYP2D6 Proteins 0.000 claims 4
- 108010081668 Cytochrome P-450 CYP3A Proteins 0.000 claims 4
- 102100029363 Cytochrome P450 2C19 Human genes 0.000 claims 4
- 102100029359 Cytochrome P450 2C8 Human genes 0.000 claims 4
- 102100029358 Cytochrome P450 2C9 Human genes 0.000 claims 4
- 102100021704 Cytochrome P450 2D6 Human genes 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- 102100033075 Prostacyclin synthase Human genes 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 108010064377 prostacyclin synthetase Proteins 0.000 claims 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims 2
- FAMJUFMHYAFYNU-UHFFFAOYSA-N 1-methyl-4-(propan-2-yl)cyclohex-1-ene Chemical compound CC(C)C1CCC(C)=CC1 FAMJUFMHYAFYNU-UHFFFAOYSA-N 0.000 claims 2
- 108010073030 25-Hydroxyvitamin D3 1-alpha-Hydroxylase Proteins 0.000 claims 2
- 102100036285 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial Human genes 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- 102100032645 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase Human genes 0.000 claims 2
- -1 CYP39 Proteins 0.000 claims 2
- 108010074918 Cytochrome P-450 CYP1A1 Proteins 0.000 claims 2
- 108010074922 Cytochrome P-450 CYP1A2 Proteins 0.000 claims 2
- 108010020070 Cytochrome P-450 CYP2B6 Proteins 0.000 claims 2
- 108010001202 Cytochrome P-450 CYP2E1 Proteins 0.000 claims 2
- 102100031476 Cytochrome P450 1A1 Human genes 0.000 claims 2
- 102100026533 Cytochrome P450 1A2 Human genes 0.000 claims 2
- 102100027417 Cytochrome P450 1B1 Human genes 0.000 claims 2
- 102100038742 Cytochrome P450 2A13 Human genes 0.000 claims 2
- 102100036194 Cytochrome P450 2A6 Human genes 0.000 claims 2
- 102100038739 Cytochrome P450 2B6 Human genes 0.000 claims 2
- 102100029368 Cytochrome P450 2C18 Human genes 0.000 claims 2
- 102100024889 Cytochrome P450 2E1 Human genes 0.000 claims 2
- 102100031461 Cytochrome P450 2J2 Human genes 0.000 claims 2
- 102100026515 Cytochrome P450 2S1 Human genes 0.000 claims 2
- 102100039205 Cytochrome P450 3A4 Human genes 0.000 claims 2
- 102100039208 Cytochrome P450 3A5 Human genes 0.000 claims 2
- 102100039203 Cytochrome P450 3A7 Human genes 0.000 claims 2
- 102100027567 Cytochrome P450 4A11 Human genes 0.000 claims 2
- 102100027419 Cytochrome P450 4B1 Human genes 0.000 claims 2
- 102100024916 Cytochrome P450 4F11 Human genes 0.000 claims 2
- 102100024918 Cytochrome P450 4F12 Human genes 0.000 claims 2
- 102100024902 Cytochrome P450 4F2 Human genes 0.000 claims 2
- 102100024901 Cytochrome P450 4F3 Human genes 0.000 claims 2
- 102100024899 Cytochrome P450 4F8 Human genes 0.000 claims 2
- 102100022027 Cytochrome P450 4X1 Human genes 0.000 claims 2
- 102100022034 Cytochrome P450 4Z1 Human genes 0.000 claims 2
- 102100038637 Cytochrome P450 7A1 Human genes 0.000 claims 2
- 102100038698 Cytochrome P450 7B1 Human genes 0.000 claims 2
- 102000023526 Cytochrome P450 Family 46 Human genes 0.000 claims 2
- 108010036233 Cytochrome P450 Family 46 Proteins 0.000 claims 2
- 101000725164 Homo sapiens Cytochrome P450 1B1 Proteins 0.000 claims 2
- 101000957389 Homo sapiens Cytochrome P450 2A13 Proteins 0.000 claims 2
- 101000875170 Homo sapiens Cytochrome P450 2A6 Proteins 0.000 claims 2
- 101000919360 Homo sapiens Cytochrome P450 2C18 Proteins 0.000 claims 2
- 101000941723 Homo sapiens Cytochrome P450 2J2 Proteins 0.000 claims 2
- 101000855328 Homo sapiens Cytochrome P450 2S1 Proteins 0.000 claims 2
- 101000745715 Homo sapiens Cytochrome P450 3A7 Proteins 0.000 claims 2
- 101000725111 Homo sapiens Cytochrome P450 4A11 Proteins 0.000 claims 2
- 101000909111 Homo sapiens Cytochrome P450 4F11 Proteins 0.000 claims 2
- 101000909108 Homo sapiens Cytochrome P450 4F12 Proteins 0.000 claims 2
- 101000909122 Homo sapiens Cytochrome P450 4F2 Proteins 0.000 claims 2
- 101000909121 Homo sapiens Cytochrome P450 4F3 Proteins 0.000 claims 2
- 101000909112 Homo sapiens Cytochrome P450 4F8 Proteins 0.000 claims 2
- 101000896935 Homo sapiens Cytochrome P450 4Z1 Proteins 0.000 claims 2
- 101000957672 Homo sapiens Cytochrome P450 7A1 Proteins 0.000 claims 2
- 101000957674 Homo sapiens Cytochrome P450 7B1 Proteins 0.000 claims 2
- 101000875401 Homo sapiens Sterol 26-hydroxylase, mitochondrial Proteins 0.000 claims 2
- 101000653005 Homo sapiens Thromboxane-A synthase Proteins 0.000 claims 2
- 101000855326 Homo sapiens Vitamin D 25-hydroxylase Proteins 0.000 claims 2
- 102100021695 Lanosterol 14-alpha demethylase Human genes 0.000 claims 2
- 101710146773 Lanosterol 14-alpha demethylase Proteins 0.000 claims 2
- 101150053185 P450 gene Proteins 0.000 claims 2
- 102100026372 Putative inactive cytochrome P450 2G1 Human genes 0.000 claims 2
- 239000004280 Sodium formate Substances 0.000 claims 2
- 108010058254 Steroid 12-alpha-Hydroxylase Proteins 0.000 claims 2
- 102100036325 Sterol 26-hydroxylase, mitochondrial Human genes 0.000 claims 2
- 102100030973 Thromboxane-A synthase Human genes 0.000 claims 2
- 102100026523 Vitamin D 25-hydroxylase Human genes 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 230000007012 clinical effect Effects 0.000 claims 2
- 229940125904 compound 1 Drugs 0.000 claims 2
- 108010026647 cytochrome P-450 4X1 Proteins 0.000 claims 2
- 108010062869 cytochrome P-450 CYP2G1 Proteins 0.000 claims 2
- 108010018719 cytochrome P-450 CYP4B1 Proteins 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 2
- 230000036470 plasma concentration Effects 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 239000010453 quartz Substances 0.000 claims 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims 2
- 235000019254 sodium formate Nutrition 0.000 claims 2
- 229910052723 transition metal Inorganic materials 0.000 claims 2
- 150000003624 transition metals Chemical class 0.000 claims 2
- OGLDWXZKYODSOB-UHFFFAOYSA-N α-phellandrene Chemical compound CC(C)C1CC=C(C)C=C1 OGLDWXZKYODSOB-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 108010084976 Cholesterol Side-Chain Cleavage Enzyme Proteins 0.000 claims 1
- 102100027516 Cholesterol side-chain cleavage enzyme, mitochondrial Human genes 0.000 claims 1
- 101100497944 Rhizopus delemar (strain RA 99-880 / ATCC MYA-4621 / FGSC 9543 / NRRL 43880) cyp11 gene Proteins 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- OGLDWXZKYODSOB-SNVBAGLBSA-N alpha-phellandrene Natural products CC(C)[C@H]1CC=C(C)C=C1 OGLDWXZKYODSOB-SNVBAGLBSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001975 deuterium Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000003203 everyday effect Effects 0.000 claims 1
- 229930182480 glucuronide Natural products 0.000 claims 1
- 150000008134 glucuronides Chemical class 0.000 claims 1
- 230000035876 healing Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 238000001802 infusion Methods 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229940087305 limonene Drugs 0.000 claims 1
- 235000001510 limonene Nutrition 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- 239000002207 metabolite Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 0 CC(C1OC1)c1ccc(CC(C)(C)*)cc1 Chemical compound CC(C1OC1)c1ccc(CC(C)(C)*)cc1 0.000 description 229
- CYWFCPPBTWOZSF-UHFFFAOYSA-N CC(C)Cc1ccc(CC(O)=O)cc1 Chemical compound CC(C)Cc1ccc(CC(O)=O)cc1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 2
- IYSPYQQBEYOGFI-UHFFFAOYSA-N CC(C)(C(O)=O)c1ccc(cc(cc2)OC)c2c1 Chemical compound CC(C)(C(O)=O)c1ccc(cc(cc2)OC)c2c1 IYSPYQQBEYOGFI-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80910706P | 2006-05-26 | 2006-05-26 | |
| US84136706P | 2006-08-30 | 2006-08-30 | |
| PCT/US2007/069480 WO2007140189A2 (en) | 2006-05-26 | 2007-05-22 | Preparation and utility of substituted carboxylic acid compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009538359A JP2009538359A (ja) | 2009-11-05 |
| JP2009538359A5 true JP2009538359A5 (enExample) | 2010-07-08 |
Family
ID=38779326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009513381A Pending JP2009538359A (ja) | 2006-05-26 | 2007-05-22 | 置換カルボン酸化合物の製造および利用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20070276042A1 (enExample) |
| EP (1) | EP2020849A2 (enExample) |
| JP (1) | JP2009538359A (enExample) |
| AU (1) | AU2007267612A1 (enExample) |
| BR (1) | BRPI0711228A2 (enExample) |
| CA (1) | CA2653262A1 (enExample) |
| WO (1) | WO2007140189A2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20110713A1 (it) | 2011-04-29 | 2012-10-30 | Bracco Imaging Spa | Processo per la preparazione di un derivato solfatato di3,5-diiodo-o-[3-iodofenil]-l-tirosina |
| ITMI20022394A1 (it) | 2002-11-13 | 2004-05-14 | Bracco Spa | Uso di triiodotironina 3-solfato come farmaco ad attivita' tireomimetica e relative formulazioni farmaceutiche. |
| TWI523652B (zh) | 2008-07-15 | 2016-03-01 | 泰瑞克公司 | 氘化苄基苯衍生物及使用方法 |
| CN102020521A (zh) * | 2009-09-10 | 2011-04-20 | 陈松源 | 氘代中药单体的制备方法和应用 |
| CN102020522A (zh) * | 2009-09-21 | 2011-04-20 | 陈松源 | 氘代药物的制备方法和应用 |
| JP6191325B2 (ja) * | 2012-08-10 | 2017-09-06 | 和光純薬工業株式会社 | 芳香族化合物の重水素化方法 |
| CN102795991B (zh) * | 2012-08-25 | 2014-07-23 | 神威药业集团有限公司 | 2-戊酰基-1,5-环己二烯-1-羧酸及其合成方法和应用 |
| FR2997856B1 (fr) * | 2012-11-14 | 2015-04-24 | Pf Medicament | Pastille medicamenteuse a base d'ibuprofene sodique dihydrate |
| TWI689490B (zh) * | 2013-03-15 | 2020-04-01 | 英商邊緣生物科技有限公司 | 用於治療纖維化之經取代之芳族化合物及相關方法 |
| WO2017070448A1 (en) * | 2015-10-22 | 2017-04-27 | The Trustees Of The University Of Pennsylvania | 2-beta-naphthyl-acetic acid analogs as akr1c3 inhibitors and methods of using same |
| WO2020210125A1 (en) | 2019-04-10 | 2020-10-15 | University Of Notre Dame Du Lac | Deuterated antimicrobial compounds |
| CN114933516B (zh) * | 2022-06-17 | 2024-01-30 | 句容宁武新材料股份有限公司 | 一种在离子液体介质中合成氘代化合物的方法 |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4567183A (en) * | 1983-03-11 | 1986-01-28 | Analgesic Associates | Analgesic and anti-inflammatory compositions comprising xanthines and methods of using same |
| US5093086A (en) * | 1988-12-23 | 1992-03-03 | Gte Products Corporation | Packed bed reactor for photochemical 196 Hg isotope separation |
| IE66933B1 (en) * | 1990-01-15 | 1996-02-07 | Elan Corp Plc | Controlled absorption naproxen formulation for once-daily administration |
| US6334997B1 (en) * | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| US6221335B1 (en) * | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| AU707748B2 (en) * | 1994-03-25 | 1999-07-22 | Isotechnika Inc. | Enhancement of the efficacy of drugs by deuteration |
| JP3985874B2 (ja) * | 1994-11-11 | 2007-10-03 | クラシエ製薬株式会社 | 感冒治療薬 |
| US6348216B1 (en) * | 1996-06-10 | 2002-02-19 | Knoll Pharmaceutical Company | Ibuprofen and narcotic analgesic compositions |
| US6361794B1 (en) * | 1996-06-12 | 2002-03-26 | Basf Corporation | Method of making ibuprofen and narcotic analgesic composition |
| US5872145A (en) * | 1996-08-16 | 1999-02-16 | Pozen, Inc. | Formulation of 5-HT agonist and NSAID for treatment of migraine |
| US6586458B1 (en) * | 1996-08-16 | 2003-07-01 | Pozen Inc. | Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs |
| US6884429B2 (en) * | 1997-09-05 | 2005-04-26 | Isotechnika International Inc. | Medical devices incorporating deuterated rapamycin for controlled delivery thereof |
| US6440710B1 (en) * | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| DE60001623T2 (de) * | 1999-12-03 | 2003-12-18 | Pfizer Products Inc., Groton | Sulfamoylheteroarylpyrazolverbindungen zur Verwendung als analgetisches/entzündungshemmendes Mittel |
| EP1134290A3 (en) * | 2000-03-14 | 2004-01-02 | Pfizer Products Inc. | Pharmacophore models for the identification of the CYP2D6 inhibitory potency of selective serotonin reuptake inhibitors |
| US6342530B1 (en) * | 2000-11-14 | 2002-01-29 | Farmacon-Il, Llc | Composition and method for parenteral administration of ibuprofen d,l- or l-lysine salt |
| US6344479B1 (en) * | 2001-03-20 | 2002-02-05 | Farmacon-Il, Llc | Method of preventing retinopathy of prematurity in a neonate |
| US6727286B2 (en) * | 2001-11-02 | 2004-04-27 | Cumberland Pharmaceuticals Inc. | Pharmaceutical composition of 2-(4-isobutylphenyl) propionic acid |
| DE10162120A1 (de) * | 2001-12-12 | 2003-06-18 | Berolina Drug Dev Ab Svedala | Deuterierte substituierte Dihydrofuranone sowie diese Verbindungen enthaltende Arzneimittel |
| DE10224888A1 (de) * | 2002-06-05 | 2003-12-24 | Merck Patent Gmbh | Pyridazinderivate |
| JP4239972B2 (ja) * | 2002-06-06 | 2009-03-18 | 和光純薬工業株式会社 | 不活性メチレンの重水素化方法 |
| WO2004000854A1 (en) * | 2002-06-20 | 2003-12-31 | Ic Vec Limited | Sulfur-containing phospholipid derivatives |
| TW200413273A (en) * | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| ATE546134T1 (de) * | 2002-12-26 | 2012-03-15 | Pozen Inc | Mehrschichtige dosierformen enthaltend naproxen und triptane |
| US20080033011A1 (en) * | 2005-07-29 | 2008-02-07 | Concert Pharmaceuticals Inc. | Novel benzo[d][1,3]-dioxol derivatives |
| CA2624179A1 (en) * | 2005-10-06 | 2007-04-12 | Auspex Pharmaceuticals, Inc. | Deuterated inhibitors of gastric h+, k+-atpase with enhanced therapeutic properties |
| US7750168B2 (en) * | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| US20090062364A1 (en) * | 2007-08-29 | 2009-03-05 | Protia, Llc | Deuterium-enriched celecoxib |
| US20090076150A1 (en) * | 2007-09-15 | 2009-03-19 | Protia, Llc | Deuterium-enriched bromfenac |
| US20090076087A1 (en) * | 2007-09-17 | 2009-03-19 | Protia, Llc | Deuterium-enriched etoricoxib |
| US20090082452A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched lumiracoxib |
| US20090082450A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched diclofenac |
-
2007
- 2007-05-22 BR BRPI0711228-9A patent/BRPI0711228A2/pt not_active IP Right Cessation
- 2007-05-22 CA CA002653262A patent/CA2653262A1/en not_active Abandoned
- 2007-05-22 US US11/752,238 patent/US20070276042A1/en not_active Abandoned
- 2007-05-22 AU AU2007267612A patent/AU2007267612A1/en not_active Abandoned
- 2007-05-22 JP JP2009513381A patent/JP2009538359A/ja active Pending
- 2007-05-22 EP EP07784044A patent/EP2020849A2/en not_active Withdrawn
- 2007-05-22 WO PCT/US2007/069480 patent/WO2007140189A2/en not_active Ceased
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