JP2011523645A5 - - Google Patents
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- Publication number
- JP2011523645A5 JP2011523645A5 JP2011510694A JP2011510694A JP2011523645A5 JP 2011523645 A5 JP2011523645 A5 JP 2011523645A5 JP 2011510694 A JP2011510694 A JP 2011510694A JP 2011510694 A JP2011510694 A JP 2011510694A JP 2011523645 A5 JP2011523645 A5 JP 2011523645A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutically acceptable
- solvate
- foregoing
- acceptable salt
- compound
- 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 187
- 150000003839 salts Chemical class 0.000 claims description 105
- 239000012453 solvate Substances 0.000 claims description 104
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 43
- 150000001413 amino acids Chemical group 0.000 claims description 38
- 229960005489 paracetamol Drugs 0.000 claims description 23
- URNSECGXFRDEDC-UHFFFAOYSA-N N-acetyl-1,4-benzoquinone imine Chemical compound CC(=O)N=C1C=CC(=O)C=C1 URNSECGXFRDEDC-UHFFFAOYSA-N 0.000 claims description 20
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 18
- 238000009472 formulation Methods 0.000 claims description 16
- 206010061218 Inflammation Diseases 0.000 claims description 15
- 208000002193 Pain Diseases 0.000 claims description 15
- 206010037660 Pyrexia Diseases 0.000 claims description 15
- 230000004054 inflammatory process Effects 0.000 claims description 15
- 208000037906 ischaemic injury Diseases 0.000 claims description 15
- 208000028389 Nerve injury Diseases 0.000 claims description 14
- 230000008764 nerve damage Effects 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 9
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical group SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 8
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical group CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 8
- 235000018417 cysteine Nutrition 0.000 claims description 8
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Chemical group SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 8
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 8
- 235000006109 methionine Nutrition 0.000 claims description 8
- 229930182817 methionine Chemical group 0.000 claims description 8
- 230000006378 damage Effects 0.000 claims description 7
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 6
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical group CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001944 cysteine derivatives Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 235000013922 glutamic acid Nutrition 0.000 claims description 6
- 239000004220 glutamic acid Substances 0.000 claims description 6
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims description 6
- 231100000304 hepatotoxicity Toxicity 0.000 claims description 6
- -1 5-thiazolidinonyl Chemical group 0.000 claims description 5
- 206010019851 Hepatotoxicity Diseases 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 230000007686 hepatotoxicity Effects 0.000 claims description 5
- 108010024636 Glutathione Proteins 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 4
- 229960004193 dextropropoxyphene Drugs 0.000 claims description 4
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims description 4
- 229960003180 glutathione Drugs 0.000 claims description 4
- 150000002332 glycine derivatives Chemical group 0.000 claims description 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 4
- 230000000415 inactivating effect Effects 0.000 claims description 4
- 210000003734 kidney Anatomy 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 4
- 125000003835 nucleoside group Chemical group 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 claims description 2
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 2
- ATOTUUBRFJHZQG-UHFFFAOYSA-N 2-amino-2-methylpropan-1-ol;8-bromo-1,3-dimethyl-7h-purine-2,6-dione Chemical compound CC(C)(N)CO.O=C1N(C)C(=O)N(C)C2=C1NC(Br)=N2 ATOTUUBRFJHZQG-UHFFFAOYSA-N 0.000 claims description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims description 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical group CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- JAQUASYNZVUNQP-USXIJHARSA-N Levorphanol Chemical compound C1C2=CC=C(O)C=C2[C@]23CCN(C)[C@H]1[C@@H]2CCCC3 JAQUASYNZVUNQP-USXIJHARSA-N 0.000 claims description 2
- 206010067125 Liver injury Diseases 0.000 claims description 2
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 2
- 229940125717 barbiturate Drugs 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 229960001948 caffeine Drugs 0.000 claims description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims description 2
- OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 claims description 2
- 229960004587 carisoprodol Drugs 0.000 claims description 2
- 229960004126 codeine Drugs 0.000 claims description 2
- 229960003529 diazepam Drugs 0.000 claims description 2
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 2
- 229960001259 diclofenac Drugs 0.000 claims description 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 2
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 2
- HCFDWZZGGLSKEP-UHFFFAOYSA-N doxylamine Chemical compound C=1C=CC=NC=1C(C)(OCCN(C)C)C1=CC=CC=C1 HCFDWZZGGLSKEP-UHFFFAOYSA-N 0.000 claims description 2
- 229960005178 doxylamine Drugs 0.000 claims description 2
- 229960005293 etodolac Drugs 0.000 claims description 2
- XFBVBWWRPKNWHW-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=N[C]3C(CC)=CC=CC3=C21 XFBVBWWRPKNWHW-UHFFFAOYSA-N 0.000 claims description 2
- 229960002390 flurbiprofen Drugs 0.000 claims description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 2
- 231100000234 hepatic damage Toxicity 0.000 claims description 2
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims description 2
- 229960000240 hydrocodone Drugs 0.000 claims description 2
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims description 2
- 229960001410 hydromorphone Drugs 0.000 claims description 2
- 229960001680 ibuprofen Drugs 0.000 claims description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 2
- 229960000991 ketoprofen Drugs 0.000 claims description 2
- 229960004752 ketorolac Drugs 0.000 claims description 2
- OZWKMVRBQXNZKK-UHFFFAOYSA-N ketorolac Chemical compound OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 OZWKMVRBQXNZKK-UHFFFAOYSA-N 0.000 claims description 2
- 229960003406 levorphanol Drugs 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 230000008818 liver damage Effects 0.000 claims description 2
- 229960004391 lorazepam Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229960001929 meloxicam Drugs 0.000 claims description 2
- DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 claims description 2
- 229960003793 midazolam Drugs 0.000 claims description 2
- 229960005181 morphine Drugs 0.000 claims description 2
- VTCDEJZIEHTNBC-UHFFFAOYSA-N n-(2,5-dioxocyclohex-3-en-1-ylidene)acetamide Chemical class CC(=O)N=C1CC(=O)C=CC1=O VTCDEJZIEHTNBC-UHFFFAOYSA-N 0.000 claims description 2
- 229960002009 naproxen Drugs 0.000 claims description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 2
- 229960003357 pamabrom Drugs 0.000 claims description 2
- 229960002702 piroxicam Drugs 0.000 claims description 2
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 2
- 229960004380 tramadol Drugs 0.000 claims description 2
- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 2
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 1
- UZVHFVZFNXBMQJ-UHFFFAOYSA-N butalbital Chemical compound CC(C)CC1(CC=C)C(=O)NC(=O)NC1=O UZVHFVZFNXBMQJ-UHFFFAOYSA-N 0.000 claims 1
- 229960002546 butalbital Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- OJLOPKGSLYJEMD-URPKTTJQSA-N methyl 7-[(1r,2r,3r)-3-hydroxy-2-[(1e)-4-hydroxy-4-methyloct-1-en-1-yl]-5-oxocyclopentyl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(=O)OC OJLOPKGSLYJEMD-URPKTTJQSA-N 0.000 claims 1
- 229960005249 misoprostol Drugs 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 238000007614 solvation Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 231100000816 toxic dose Toxicity 0.000 claims 1
- 238000000034 method Methods 0.000 description 17
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- OCWJVIUDOHXKHI-PWNUKQCCSA-N methyl 7-[(1r,2s)-2-[(e)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopent-3-en-1-yl]heptanoate Chemical compound CCCCC(C)(O)C\C=C\[C@H]1C=CC(=O)[C@@H]1CCCCCCC(=O)OC OCWJVIUDOHXKHI-PWNUKQCCSA-N 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5477708P | 2008-05-20 | 2008-05-20 | |
| US61/054,777 | 2008-05-20 | ||
| PCT/US2009/044749 WO2009143299A1 (en) | 2008-05-20 | 2009-05-20 | Hepatoprotectant acetaminophen mutual prodrugs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014018474A Division JP2014111632A (ja) | 2008-05-20 | 2014-02-03 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011523645A JP2011523645A (ja) | 2011-08-18 |
| JP2011523645A5 true JP2011523645A5 (https=) | 2012-07-05 |
| JP5701750B2 JP5701750B2 (ja) | 2015-04-15 |
Family
ID=41340540
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011510694A Expired - Fee Related JP5701750B2 (ja) | 2008-05-20 | 2009-05-20 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2014018474A Withdrawn JP2014111632A (ja) | 2008-05-20 | 2014-02-03 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2015180278A Withdrawn JP2015227384A (ja) | 2008-05-20 | 2015-09-14 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2017140812A Withdrawn JP2017186380A (ja) | 2008-05-20 | 2017-07-20 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2019034258A Withdrawn JP2019081793A (ja) | 2008-05-20 | 2019-02-27 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2020201931A Withdrawn JP2021036001A (ja) | 2008-05-20 | 2020-12-04 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014018474A Withdrawn JP2014111632A (ja) | 2008-05-20 | 2014-02-03 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2015180278A Withdrawn JP2015227384A (ja) | 2008-05-20 | 2015-09-14 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2017140812A Withdrawn JP2017186380A (ja) | 2008-05-20 | 2017-07-20 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2019034258A Withdrawn JP2019081793A (ja) | 2008-05-20 | 2019-02-27 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
| JP2020201931A Withdrawn JP2021036001A (ja) | 2008-05-20 | 2020-12-04 | 肝保護剤アセトアミノフェンミューチュアルプロドラッグ |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US20110263545A1 (https=) |
| EP (1) | EP2285419A4 (https=) |
| JP (6) | JP5701750B2 (https=) |
| KR (1) | KR101717145B1 (https=) |
| CN (1) | CN102149412A (https=) |
| AU (1) | AU2009249071A1 (https=) |
| BR (1) | BRPI0912820A2 (https=) |
| CA (2) | CA2724788C (https=) |
| IL (1) | IL209384A0 (https=) |
| MX (1) | MX2010012647A (https=) |
| RU (1) | RU2010151951A (https=) |
| WO (1) | WO2009143299A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101717145B1 (ko) | 2008-05-20 | 2017-03-16 | 노이로제스엑스, 인코포레이티드 | 간보호제 아세트아미노펜 공통 프로드러그 |
| RU2010151953A (ru) | 2008-05-20 | 2012-06-27 | Ньюроджесэкс, Инк. (Us) | Карбонатные продукты и способы их применения |
| KR101698028B1 (ko) | 2008-05-20 | 2017-01-26 | 노이로제스엑스, 인코포레이티드 | 수용성 아세트아미노펜 유사체 |
| AU2012312136B2 (en) | 2011-09-22 | 2017-06-29 | Acorda Therapeutics, Inc. | Acetaminophen conjugates, compositions and methods of use thereof |
| US20140179615A1 (en) * | 2012-07-12 | 2014-06-26 | Hainan Weikang Pharmaceutical (Qianshan) Co., Ltd. | Glutathione and Acetaminophen Composition and Preparation Method Thereof |
| CA3042642A1 (en) | 2013-08-12 | 2015-02-19 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded immediate release abuse deterrent pill |
| US10172797B2 (en) | 2013-12-17 | 2019-01-08 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded extended release abuse deterrent pill |
| US9492444B2 (en) | 2013-12-17 | 2016-11-15 | Pharmaceutical Manufacturing Research Services, Inc. | Extruded extended release abuse deterrent pill |
| CA2955229C (en) | 2014-07-17 | 2020-03-10 | Pharmaceutical Manufacturing Research Services, Inc. | Immediate release abuse deterrent liquid fill dosage form |
| US20170246194A1 (en) * | 2014-08-15 | 2017-08-31 | Purdue Pharma L.P. | Acetaminophen-Containing Analgesic Formulations With Reduced Hepatotoxicity |
| WO2016064873A1 (en) | 2014-10-20 | 2016-04-28 | Pharmaceutical Manufacturing Research Services, Inc. | Extended release abuse deterrent liquid fill dosage form |
| US11389409B2 (en) * | 2019-08-30 | 2022-07-19 | Remedy Diagnostics LLC | Transdermal device comprising acetaminophen prodrug |
Family Cites Families (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4035507A (en) * | 1975-04-17 | 1977-07-12 | Interx Research Corporation | Novel, transient pro-drug forms of L-DOPA to treat Parkinson's disease |
| GB1583602A (en) | 1977-05-26 | 1981-01-28 | Sterwin Ag | N-acetyl-para-aminophenyl-n'-acetyl-amino-thioalkanoic acid ester derivatives |
| US4562024A (en) | 1982-07-06 | 1985-12-31 | Sterling Drug Inc. | Process for preparing granulate containing poorly compressible medicinally active matter |
| CH654302A5 (de) * | 1983-05-04 | 1986-02-14 | Sandoz Ag | Acylaminophenolderivate, ihre herstellung und arzneimittel, welche sie enthalten. |
| US5001115A (en) * | 1989-05-17 | 1991-03-19 | University Of Florida | Prodrugs of biologically active hydroxyaromatic compounds |
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-
2009
- 2009-05-20 KR KR1020107028511A patent/KR101717145B1/ko not_active Expired - Fee Related
- 2009-05-20 WO PCT/US2009/044749 patent/WO2009143299A1/en not_active Ceased
- 2009-05-20 AU AU2009249071A patent/AU2009249071A1/en not_active Abandoned
- 2009-05-20 JP JP2011510694A patent/JP5701750B2/ja not_active Expired - Fee Related
- 2009-05-20 CA CA2724788A patent/CA2724788C/en not_active Expired - Fee Related
- 2009-05-20 MX MX2010012647A patent/MX2010012647A/es active IP Right Grant
- 2009-05-20 CA CA2946445A patent/CA2946445C/en not_active Expired - Fee Related
- 2009-05-20 BR BRPI0912820A patent/BRPI0912820A2/pt not_active IP Right Cessation
- 2009-05-20 EP EP09751527A patent/EP2285419A4/en not_active Withdrawn
- 2009-05-20 US US12/993,091 patent/US20110263545A1/en not_active Abandoned
- 2009-05-20 CN CN2009801282430A patent/CN102149412A/zh active Pending
- 2009-05-20 RU RU2010151951/15A patent/RU2010151951A/ru not_active Application Discontinuation
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2010
- 2010-11-17 IL IL209384A patent/IL209384A0/en unknown
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2014
- 2014-02-03 JP JP2014018474A patent/JP2014111632A/ja not_active Withdrawn
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2015
- 2015-09-14 JP JP2015180278A patent/JP2015227384A/ja not_active Withdrawn
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2016
- 2016-05-09 US US15/150,099 patent/US9951001B2/en active Active
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2017
- 2017-07-20 JP JP2017140812A patent/JP2017186380A/ja not_active Withdrawn
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2018
- 2018-03-15 US US15/922,273 patent/US20190062273A1/en not_active Abandoned
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2019
- 2019-02-27 JP JP2019034258A patent/JP2019081793A/ja not_active Withdrawn
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2020
- 2020-12-04 JP JP2020201931A patent/JP2021036001A/ja not_active Withdrawn
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