AU2009249071A1 - Hepatoprotectant acetaminophen mutual prodrugs - Google Patents
Hepatoprotectant acetaminophen mutual prodrugs Download PDFInfo
- Publication number
- AU2009249071A1 AU2009249071A1 AU2009249071A AU2009249071A AU2009249071A1 AU 2009249071 A1 AU2009249071 A1 AU 2009249071A1 AU 2009249071 A AU2009249071 A AU 2009249071A AU 2009249071 A AU2009249071 A AU 2009249071A AU 2009249071 A1 AU2009249071 A1 AU 2009249071A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- acetaminophen
- substituted
- moiety
- hepatoprotectant
- 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.)
- Abandoned
Links
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title claims description 795
- 229960005489 paracetamol Drugs 0.000 title claims description 388
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 title claims description 204
- 239000000651 prodrug Substances 0.000 title description 190
- 229940002612 prodrug Drugs 0.000 title description 190
- 150000001875 compounds Chemical class 0.000 claims description 304
- 239000000203 mixture Substances 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 90
- 238000009472 formulation Methods 0.000 claims description 82
- 150000001413 amino acids Chemical group 0.000 claims description 81
- 150000003839 salts Chemical class 0.000 claims description 63
- 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 60
- 208000002193 Pain Diseases 0.000 claims description 59
- 201000010099 disease Diseases 0.000 claims description 59
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
- -1 5-thiazolidinonyl Chemical group 0.000 claims description 54
- 231100000304 hepatotoxicity Toxicity 0.000 claims description 54
- 230000036407 pain Effects 0.000 claims description 54
- 206010019851 Hepatotoxicity Diseases 0.000 claims description 52
- 230000007686 hepatotoxicity Effects 0.000 claims description 51
- 239000012453 solvate Substances 0.000 claims description 42
- 206010037660 Pyrexia Diseases 0.000 claims description 39
- 238000011282 treatment Methods 0.000 claims description 35
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical group CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 33
- 102100020870 La-related protein 6 Human genes 0.000 claims description 33
- 108050008265 La-related protein 6 Proteins 0.000 claims description 33
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical group SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 32
- 229960003180 glutathione Drugs 0.000 claims description 30
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Chemical group SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 27
- 235000018417 cysteine Nutrition 0.000 claims description 27
- 229930182817 methionine Chemical group 0.000 claims description 27
- 108010024636 Glutathione Proteins 0.000 claims description 23
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- 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
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 20
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- 230000004054 inflammatory process Effects 0.000 claims description 19
- 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 18
- 208000027418 Wounds and injury Diseases 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 17
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- 238000003786 synthesis reaction Methods 0.000 claims description 16
- 239000003937 drug carrier Substances 0.000 claims description 12
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 230000003247 decreasing effect Effects 0.000 claims description 10
- WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000004471 Glycine Substances 0.000 claims description 8
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims description 8
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- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 6
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
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- 229940049706 benzodiazepine Drugs 0.000 claims description 5
- 229960004193 dextropropoxyphene Drugs 0.000 claims description 5
- 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 5
- 231100000234 hepatic damage Toxicity 0.000 claims description 5
- 230000008818 liver damage Effects 0.000 claims description 5
- 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 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
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- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-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
- 150000001944 cysteine derivatives Chemical group 0.000 claims description 4
- 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 4
- 229960003529 diazepam Drugs 0.000 claims description 4
- 150000002332 glycine derivatives Chemical group 0.000 claims description 4
- 229960001680 ibuprofen Drugs 0.000 claims description 4
- 229960004391 lorazepam Drugs 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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 4
- 229960003793 midazolam Drugs 0.000 claims description 4
- 229960002009 naproxen Drugs 0.000 claims description 4
- 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 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 4
- 125000003835 nucleoside group Chemical group 0.000 claims description 4
- 230000004936 stimulating effect Effects 0.000 claims description 4
- 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 3
- 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 3
- 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 3
- 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 3
- 229940125717 barbiturate Drugs 0.000 claims description 3
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- 229960002546 butalbital Drugs 0.000 claims description 3
- OFZCIYFFPZCNJE-UHFFFAOYSA-N carisoprodol Chemical compound NC(=O)OCC(C)(CCC)COC(=O)NC(C)C OFZCIYFFPZCNJE-UHFFFAOYSA-N 0.000 claims description 3
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- 229960001259 diclofenac Drugs 0.000 claims description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 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
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- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
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- 239000003053 toxin Substances 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 229940072651 tylenol Drugs 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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- 239000004474 valine Substances 0.000 description 1
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- 229940087652 vioxx Drugs 0.000 description 1
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Physiology (AREA)
- Vascular Medicine (AREA)
- Toxicology (AREA)
- Urology & Nephrology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2009249071A1 true AU2009249071A1 (en) | 2009-11-26 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009249071A Abandoned AU2009249071A1 (en) | 2008-05-20 | 2009-05-20 | Hepatoprotectant acetaminophen mutual prodrugs |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US20110263545A1 (enExample) |
| EP (1) | EP2285419A4 (enExample) |
| JP (6) | JP5701750B2 (enExample) |
| KR (1) | KR101717145B1 (enExample) |
| CN (1) | CN102149412A (enExample) |
| AU (1) | AU2009249071A1 (enExample) |
| BR (1) | BRPI0912820A2 (enExample) |
| CA (2) | CA2724788C (enExample) |
| IL (1) | IL209384A0 (enExample) |
| MX (1) | MX2010012647A (enExample) |
| RU (1) | RU2010151951A (enExample) |
| WO (1) | WO2009143299A1 (enExample) |
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| WO2009143299A1 (en) | 2008-05-20 | 2009-11-26 | Neurogesx, Inc. | Hepatoprotectant acetaminophen mutual prodrugs |
| CN105254662A (zh) | 2008-05-20 | 2016-01-20 | 阿索尔达治疗公司 | 水溶性对乙酰氨基酚类似物 |
| CA2724881C (en) | 2008-05-20 | 2016-09-27 | Neurogesx, Inc. | Carbonate prodrugs and methods of using the same |
| US9024055B2 (en) | 2011-09-22 | 2015-05-05 | 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 |
| JP6539274B2 (ja) | 2013-08-12 | 2019-07-03 | ファーマシューティカル マニュファクチュアリング リサーチ サービシズ，インコーポレーテッド | 押出成形された即放性乱用抑止性丸剤 |
| 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 |
| EP3169315B1 (en) | 2014-07-17 | 2020-06-24 | 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 |
| US20160106737A1 (en) | 2014-10-20 | 2016-04-21 | 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 |
| US5474757A (en) * | 1992-10-16 | 1995-12-12 | Rutgers University | Prevention of acetaminophen overdose toxicity with organosulfur compounds |
| DE4327462A1 (de) * | 1993-08-16 | 1995-02-23 | Carl Heinrich Dr Weischer | Neue N-Acetyl-p-Aminophenol-Derivate zur Bekämpfung von Schmerzzuständen |
| US5916910A (en) | 1997-06-04 | 1999-06-29 | Medinox, Inc. | Conjugates of dithiocarbamates with pharmacologically active agents and uses therefore |
| US6710086B1 (en) | 2000-02-25 | 2004-03-23 | Medinox, Inc. | Protected forms of pharmacologically active agents and uses therefor |
| MXPA02008797A (es) | 2000-03-14 | 2005-09-08 | Actelion Pharmaceuticals Ltd | Derivados de 1,2,3,4-tetrahidroisoquinolina. |
| WO2001068069A2 (en) | 2000-03-15 | 2001-09-20 | King's College London | Pharmaceutical composition comprising paracetamol |
| IT1319202B1 (it) | 2000-10-12 | 2003-09-26 | Nicox Sa | Farmaci per le malattie a base infiammatoria. |
| US20030073618A1 (en) * | 2001-02-08 | 2003-04-17 | Kozhemyakin Leonid A. | Compounds comprising disulfide-containing peptides and nitrogenous bases, and medical uses thereof |
| KR20030033007A (ko) | 2001-05-31 | 2003-04-26 | 코울터 파머수티컬, 인코포레이티드 | 세포독소, 약물전구체, 링커 및 이에 유용한 안정화제 |
| ATE506064T1 (de) | 2001-06-05 | 2011-05-15 | Control Delivery Systems | Analgetika mit verzögerter wirkstoffabgabe |
| AU2002350207A1 (en) | 2001-11-19 | 2003-06-10 | Control Delivery Systems, Inc. | Topical delivery of codrugs |
| JP2005513050A (ja) | 2001-12-10 | 2005-05-12 | コントロール・デリバリー・システムズ・インコーポレイテッド | 尿生殖路疾患の治療 |
| US20050164994A1 (en) | 2001-12-10 | 2005-07-28 | Control Deliver Systems, Inc. | Treatment of genitourinary tract disorders |
| JP5105697B2 (ja) | 2002-01-18 | 2012-12-26 | シヴィダ・インコーポレイテッド | コドラッグのコントロールデリバリ用ポリマー性ゲルシステム |
| US20040058946A1 (en) | 2002-07-05 | 2004-03-25 | Buchwald Stephen L. | Abuse-resistant prodrugs of oxycodone and other pharmaceuticals |
| US7381721B2 (en) | 2003-03-17 | 2008-06-03 | Adolor Corporation | Substituted piperidine compounds |
| AU2004278414B2 (en) | 2003-10-01 | 2012-05-24 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| WO2005047231A1 (en) | 2003-11-12 | 2005-05-26 | Applied Nanosystems B.V. | Non-symmetrical gelling agent |
| US20050113294A1 (en) | 2003-11-21 | 2005-05-26 | Adolor Corporation. | Carboxamide and amino derivatives and methods of their use |
| TW200616604A (en) | 2004-08-26 | 2006-06-01 | Nicholas Piramal India Ltd | Nitric oxide releasing prodrugs containing bio-cleavable linker |
| US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| JP2009502931A (ja) | 2005-07-27 | 2009-01-29 | オレキシジェン・セラピューティクス・インコーポレーテッド | 体重減少を促すための組成物 |
| WO2007112000A2 (en) | 2006-03-24 | 2007-10-04 | Wyeth | Treatment of pain |
| WO2008070149A2 (en) | 2006-12-05 | 2008-06-12 | Neurogesx, Inc. | Prodrugs and methods of making and using the same |
| CA2724881C (en) | 2008-05-20 | 2016-09-27 | Neurogesx, Inc. | Carbonate prodrugs and methods of using the same |
| CN105254662A (zh) | 2008-05-20 | 2016-01-20 | 阿索尔达治疗公司 | 水溶性对乙酰氨基酚类似物 |
| WO2009143299A1 (en) | 2008-05-20 | 2009-11-26 | Neurogesx, Inc. | Hepatoprotectant acetaminophen mutual prodrugs |
-
2009
- 2009-05-20 WO PCT/US2009/044749 patent/WO2009143299A1/en not_active Ceased
- 2009-05-20 KR KR1020107028511A patent/KR101717145B1/ko not_active Expired - Fee Related
- 2009-05-20 CA CA2724788A patent/CA2724788C/en not_active Expired - Fee Related
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- 2009-05-20 CA CA2946445A patent/CA2946445C/en not_active Expired - Fee Related
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- 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
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2015
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2016
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2017
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2018
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2019
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2020
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2724788C (en) | 2016-12-06 |
| JP2014111632A (ja) | 2014-06-19 |
| MX2010012647A (es) | 2010-12-14 |
| JP2017186380A (ja) | 2017-10-12 |
| CN102149412A (zh) | 2011-08-10 |
| JP2019081793A (ja) | 2019-05-30 |
| RU2010151951A (ru) | 2012-06-27 |
| CA2724788A1 (en) | 2009-11-26 |
| CA2946445A1 (en) | 2009-11-26 |
| JP2015227384A (ja) | 2015-12-17 |
| IL209384A0 (en) | 2011-01-31 |
| CA2946445C (en) | 2019-01-08 |
| JP2021036001A (ja) | 2021-03-04 |
| EP2285419A1 (en) | 2011-02-23 |
| JP2011523645A (ja) | 2011-08-18 |
| US20110263545A1 (en) | 2011-10-27 |
| JP5701750B2 (ja) | 2015-04-15 |
| US9951001B2 (en) | 2018-04-24 |
| EP2285419A4 (en) | 2012-05-02 |
| WO2009143299A1 (en) | 2009-11-26 |
| US20160326107A1 (en) | 2016-11-10 |
| KR20110011694A (ko) | 2011-02-08 |
| BRPI0912820A2 (pt) | 2015-10-13 |
| US20190062273A1 (en) | 2019-02-28 |
| KR101717145B1 (ko) | 2017-03-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |