JP2014502972A5 - - Google Patents
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- Publication number
- JP2014502972A5 JP2014502972A5 JP2013548605A JP2013548605A JP2014502972A5 JP 2014502972 A5 JP2014502972 A5 JP 2014502972A5 JP 2013548605 A JP2013548605 A JP 2013548605A JP 2013548605 A JP2013548605 A JP 2013548605A JP 2014502972 A5 JP2014502972 A5 JP 2014502972A5
- Authority
- JP
- Japan
- Prior art keywords
- prodrug
- trypsin
- oxycodone
- compound
- trypsin inhibitor
- 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
- 229940002612 prodrug Drugs 0.000 claims 37
- 239000000651 prodrug Substances 0.000 claims 37
- 239000002753 trypsin inhibitor Substances 0.000 claims 31
- 229940122618 Trypsin inhibitor Drugs 0.000 claims 29
- 101710162629 Trypsin inhibitor Proteins 0.000 claims 29
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims 26
- 229960002085 oxycodone Drugs 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 22
- 239000000203 mixture Substances 0.000 claims 22
- 102000004142 Trypsin Human genes 0.000 claims 18
- 108090000631 Trypsin Proteins 0.000 claims 18
- 239000012588 trypsin Substances 0.000 claims 18
- 238000000034 method Methods 0.000 claims 10
- 238000006243 chemical reaction Methods 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 150000002085 enols Chemical class 0.000 claims 5
- 230000037406 food intake Effects 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 230000003278 mimic effect Effects 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- -1 amino, substituted amino, hydroxyl Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000009472 formulation Methods 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 239000004475 Arginine Substances 0.000 claims 2
- 102000004190 Enzymes Human genes 0.000 claims 2
- 108090000790 Enzymes Proteins 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Chemical group CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Chemical group 0.000 claims 2
- 235000013877 carbamide Nutrition 0.000 claims 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 2
- 238000003776 cleavage reaction Methods 0.000 claims 2
- 238000013270 controlled release Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Chemical group CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical group 0.000 claims 2
- 238000013160 medical therapy Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 230000007017 scission Effects 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- SXNCILYLEKIXPV-IZZNHLLZSA-N (4s)-4-[[(2r)-2-(benzylsulfonylamino)-4-phenylbutanoyl]amino]-5-[(4-carbamimidoylphenyl)methylamino]-5-oxopentanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](NS(=O)(=O)CC=1C=CC=CC=1)CCC1=CC=CC=C1 SXNCILYLEKIXPV-IZZNHLLZSA-N 0.000 claims 1
- WPANETAWYGDRLL-UHFFFAOYSA-N 4-aminobenzenecarboximidamide Chemical compound NC(=N)C1=CC=C(N)C=C1 WPANETAWYGDRLL-UHFFFAOYSA-N 0.000 claims 1
- LPRSIBLBCFRSKX-QFIPXVFZSA-N 6-[4-[(2s)-5-(diaminomethylideneamino)-2-(naphthalen-2-ylsulfonylamino)pentanoyl]piperazin-1-yl]-6-oxohexanoic acid Chemical compound O=C([C@@H](NS(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CCCNC(=N)N)N1CCN(C(=O)CCCCC(O)=O)CC1 LPRSIBLBCFRSKX-QFIPXVFZSA-N 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- ZXBYWYQEQQBMBT-UHFFFAOYSA-N amido phenyl pyruvic acid Chemical compound NC(=N)C1=CC=C(CC(=O)C(O)=O)C=C1 ZXBYWYQEQQBMBT-UHFFFAOYSA-N 0.000 claims 1
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000010228 ex vivo assay Methods 0.000 claims 1
- 238000005462 in vivo assay Methods 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- YVTDJCBGKCQSPF-DFIMAEIUSA-N CC(C)(CNC([C@H](CCCNC(N)=N)NC(CNC(CC(O)=O)=O)=O)=O)CN(C)C(OC([C@@H]([C@]12CCN(C)[C@@H]3C4)Oc5c1c4ccc5OC)=CC[C@]23O)=O Chemical compound CC(C)(CNC([C@H](CCCNC(N)=N)NC(CNC(CC(O)=O)=O)=O)=O)CN(C)C(OC([C@@H]([C@]12CCN(C)[C@@H]3C4)Oc5c1c4ccc5OC)=CC[C@]23O)=O YVTDJCBGKCQSPF-DFIMAEIUSA-N 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161431781P | 2011-01-11 | 2011-01-11 | |
| US61/431,781 | 2011-01-11 | ||
| PCT/US2012/020649 WO2012096887A2 (en) | 2011-01-11 | 2012-01-09 | Compositions comprising enzyme-cleavable oxycodone prodrug |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014502972A JP2014502972A (ja) | 2014-02-06 |
| JP2014502972A5 true JP2014502972A5 (enExample) | 2015-06-18 |
| JP6016810B2 JP6016810B2 (ja) | 2016-10-26 |
Family
ID=46455749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013548605A Active JP6016810B2 (ja) | 2011-01-11 | 2012-01-09 | 酵素切断可能なオキシコドンプロドラッグを含んでなる組成物 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US8569228B2 (enExample) |
| EP (1) | EP2663187B1 (enExample) |
| JP (1) | JP6016810B2 (enExample) |
| CN (1) | CN103384472B (enExample) |
| AU (1) | AU2012205733B2 (enExample) |
| BR (1) | BR112013017296B1 (enExample) |
| CA (1) | CA2814763C (enExample) |
| DK (1) | DK2663187T3 (enExample) |
| ES (1) | ES2584634T3 (enExample) |
| IL (1) | IL225904B (enExample) |
| RU (1) | RU2609412C2 (enExample) |
| TW (1) | TWI526209B (enExample) |
| WO (1) | WO2012096887A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
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| SI1765292T1 (en) | 2004-06-12 | 2018-04-30 | Collegium Pharmaceutical, Inc. | Formulations of medicines to discourage abuse |
| UA102916C2 (uk) | 2009-07-02 | 2013-08-27 | Кемфарм, Інк. | Композиція на основі кон'югату гідрокодону з бензойною кислотою, похідними бензойної кислоти або гетероарилкарбоновою кислотою, проліки, спосіб лікування від зловживань |
| SG179026A1 (en) | 2009-09-08 | 2012-04-27 | Signature Therapeutics Inc | Compositions comprising enzyme-cleavable ketone-modified opioid prodrugs and optional inhibitors thereof |
| US10668060B2 (en) | 2009-12-10 | 2020-06-02 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| US20110262359A1 (en) * | 2010-04-21 | 2011-10-27 | Jenkins Thomas E | Compositions comprising enzyme-cleavable prodrugs of active agents and inhibitors thereof |
| EP2560486B1 (en) | 2010-04-21 | 2018-11-21 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable amphetamine prodrugs and inhibitors thereof |
| US20110262355A1 (en) | 2010-04-21 | 2011-10-27 | Jenkins Thomas E | Compositions comprising enzyme-cleavable opioid prodrugs and inhibitors thereof |
| CA2814763C (en) * | 2011-01-11 | 2019-05-28 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable oxycodone prodrug |
| WO2012122420A2 (en) | 2011-03-09 | 2012-09-13 | Pharmacofore, Inc. | Opioid prodrugs with heterocyclic linkers |
| JP6148182B2 (ja) | 2011-03-09 | 2017-06-14 | シグネーチャー セラピューティクス, インク.Signature Therapeutics, Inc. | 複素環式リンカーを有する活性薬剤プロドラッグ |
| CA2932477C (en) | 2013-12-06 | 2023-10-10 | Baikang (Suzhou) Co., Ltd | Bioreversable promoieties for nitrogen-containing and hydroxyl-containing drugs |
| BR112017011069A2 (pt) | 2014-11-25 | 2018-07-10 | Kempharm Inc | ácido benzóico, derivados e ácido benzóico e conjugados de ácido heteroaril carboxílico de oxicodona |
| US11634384B2 (en) | 2014-11-25 | 2023-04-25 | Concentric Analgesics, Inc. | Prodrugs of phenolic TRPV1 agonists |
| US10335406B2 (en) | 2015-10-01 | 2019-07-02 | Elysium Therapeutics, Inc. | Opioid compositions resistant to overdose and abuse |
| GB2556817B (en) | 2015-10-01 | 2019-11-06 | Elysium Therapeutics Inc | Polysubunit opioid prodrugs resistant to overdose and abuse |
| EP3210630A1 (en) | 2016-02-29 | 2017-08-30 | G.L. Pharma GmbH | Abuse-deterrent pharmaceutical compositions |
| EP3463576A4 (en) | 2016-05-25 | 2020-01-15 | Concentric Analgesics, Inc. | MEDICINAL PRODUCTS BASED ON PHENOLIC TRPV1 AGONISTS IN ASSOCIATION WITH LOCAL ANESTHETICS AND VASOCONSTRUCTS TO IMPROVE LOCAL ANESTHESIA |
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| WO2018170465A1 (en) * | 2017-03-17 | 2018-09-20 | Elysium Therapeutics, Inc. | Polysubunit opioid prodrugs resistant to overdose and abuse |
| US11666888B2 (en) | 2018-02-05 | 2023-06-06 | Bio-Rad Laboratories, Inc. | Chromatography resin having an anionic exchange-hydrophobic mixed mode ligand |
| AU2019310118A1 (en) | 2018-07-27 | 2021-03-11 | Concentric Analgesics, Inc. | Pegylated prodrugs of phenolic TRPV1 agonists |
| US12384744B2 (en) | 2021-09-29 | 2025-08-12 | Ensysce Biosciences Inc. | Enzyme-cleavable methadone prodrugs and methods of use thereof |
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| US8497237B2 (en) | 2011-01-11 | 2013-07-30 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable oxycodone prodrug |
| CA2814763C (en) | 2011-01-11 | 2019-05-28 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable oxycodone prodrug |
| JP6148182B2 (ja) | 2011-03-09 | 2017-06-14 | シグネーチャー セラピューティクス, インク.Signature Therapeutics, Inc. | 複素環式リンカーを有する活性薬剤プロドラッグ |
| WO2012122420A2 (en) | 2011-03-09 | 2012-09-13 | Pharmacofore, Inc. | Opioid prodrugs with heterocyclic linkers |
-
2012
- 2012-01-09 CA CA2814763A patent/CA2814763C/en active Active
- 2012-01-09 DK DK12734573.4T patent/DK2663187T3/en active
- 2012-01-09 BR BR112013017296-7A patent/BR112013017296B1/pt active IP Right Grant
- 2012-01-09 US US13/346,062 patent/US8569228B2/en active Active
- 2012-01-09 ES ES12734573.4T patent/ES2584634T3/es active Active
- 2012-01-09 RU RU2013137452A patent/RU2609412C2/ru active
- 2012-01-09 CN CN201280003814.XA patent/CN103384472B/zh active Active
- 2012-01-09 WO PCT/US2012/020649 patent/WO2012096887A2/en not_active Ceased
- 2012-01-09 EP EP12734573.4A patent/EP2663187B1/en active Active
- 2012-01-09 AU AU2012205733A patent/AU2012205733B2/en active Active
- 2012-01-09 JP JP2013548605A patent/JP6016810B2/ja active Active
- 2012-01-10 TW TW101100923A patent/TWI526209B/zh active
-
2013
- 2013-04-23 IL IL225904A patent/IL225904B/en active IP Right Grant
- 2013-09-24 US US14/035,871 patent/US8962547B2/en active Active
-
2015
- 2015-01-09 US US14/593,855 patent/US9499581B2/en active Active
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