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 |
|---|---|---|---|---|
| DK1765292T3 (en) | 2004-06-12 | 2018-01-02 | Collegium Pharmaceutical Inc | ABUSE PREVENTIONAL PHARMACEUTICAL FORMULATIONS |
| 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 |
| BR112012005124B1 (pt) | 2009-09-08 | 2021-11-09 | Signature Therapeutics, Inc. | Pro-fármaco de opioide modificado por cetona, seu método de preparação, sua composição farmacêutica, sua unidade de dose, métodos e usos |
| US10668060B2 (en) | 2009-12-10 | 2020-06-02 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| US20110262355A1 (en) | 2010-04-21 | 2011-10-27 | Jenkins Thomas E | Compositions comprising enzyme-cleavable opioid prodrugs and inhibitors thereof |
| WO2011133348A1 (en) | 2010-04-21 | 2011-10-27 | Pharmacofore, Inc. | Compositions comprising enzyme-cleavable amphetamine prodrugs and inhibitors thereof |
| US20110262359A1 (en) * | 2010-04-21 | 2011-10-27 | Jenkins Thomas E | Compositions comprising enzyme-cleavable prodrugs of active agents and inhibitors thereof |
| CN103384472B (zh) * | 2011-01-11 | 2016-01-20 | 特色疗法股份有限公司 | 包含酶可裂解的羟考酮药物前体的组合物 |
| WO2012122420A2 (en) | 2011-03-09 | 2012-09-13 | Pharmacofore, Inc. | Opioid prodrugs with heterocyclic linkers |
| BR112013022946A2 (pt) | 2011-03-09 | 2017-07-18 | Signature Therapeutics Inc | pró-fármacos de agentes ativos com ligantes heterocíclocos |
| WO2015081891A1 (en) | 2013-12-06 | 2015-06-11 | Baikang (Suzhou) Co., Ltd | Bioreversable promoieties for nitrogen-containing and hydroxyl-containing drugs |
| US9850252B2 (en) * | 2014-11-25 | 2017-12-26 | Kempharm, Inc. | Benzoic acid, benzoic acid derivatives and heteroaryl carboxylic acid conjugates of oxycodone, prodrugs, methods of making and use thereof |
| US11634384B2 (en) | 2014-11-25 | 2023-04-25 | Concentric Analgesics, Inc. | Prodrugs of phenolic TRPV1 agonists |
| CA2998708C (en) * | 2015-10-01 | 2019-09-03 | Elysium Therapeutics, Inc. | Polysubunit opioid prodrugs resistant to overdose and abuse |
| US10335406B2 (en) | 2015-10-01 | 2019-07-02 | Elysium Therapeutics, Inc. | Opioid compositions 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. | PRODRUGS BY PHENOLIC TRPV1 AGONISTS IN COMBINATION WITH LOCAL ANESTHETIC AND VASOCONSTRICTORS FOR IMPROVED LOCAL ANESTHESIA |
| US9737530B1 (en) | 2016-06-23 | 2017-08-22 | Collegium Pharmaceutical, Inc. | Process of making stable abuse-deterrent oral formulations |
| EP3555280A4 (en) | 2016-12-19 | 2020-09-09 | The Regents of The University of California | PEPTIDES SENSITIVE TO TWO ENZYMES |
| EP3554548A4 (en) | 2016-12-19 | 2020-08-19 | The Regents of The University of California | NON-CRUSHABLE PILL FORMULATIONS |
| JP7234130B2 (ja) * | 2017-03-17 | 2023-03-07 | エリージウム セラピューティクス， インコーポレイテッド | 過剰摂取および乱用に対して抵抗性のポリサブユニットオピオイドプロドラッグ |
| CN111683976B (zh) | 2018-02-05 | 2022-11-18 | 生物辐射实验室股份有限公司 | 具有阴离子交换-疏水混合模式配体的色谱树脂 |
| CA3107433A1 (en) | 2018-07-27 | 2020-01-30 | 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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| CN103384472B (zh) | 2011-01-11 | 2016-01-20 | 特色疗法股份有限公司 | 包含酶可裂解的羟考酮药物前体的组合物 |
| US8497237B2 (en) | 2011-01-11 | 2013-07-30 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable oxycodone prodrug |
| WO2012122420A2 (en) | 2011-03-09 | 2012-09-13 | Pharmacofore, Inc. | Opioid prodrugs with heterocyclic linkers |
| BR112013022946A2 (pt) | 2011-03-09 | 2017-07-18 | Signature Therapeutics Inc | pró-fármacos de agentes ativos com ligantes heterocíclocos |
-
2012
- 2012-01-09 CN CN201280003814.XA patent/CN103384472B/zh active Active
- 2012-01-09 JP JP2013548605A patent/JP6016810B2/ja active Active
- 2012-01-09 BR BR112013017296-7A patent/BR112013017296B1/pt active IP Right Grant
- 2012-01-09 DK DK12734573.4T patent/DK2663187T3/en active
- 2012-01-09 WO PCT/US2012/020649 patent/WO2012096887A2/en not_active Ceased
- 2012-01-09 AU AU2012205733A patent/AU2012205733B2/en active Active
- 2012-01-09 EP EP12734573.4A patent/EP2663187B1/en active Active
- 2012-01-09 CA CA2814763A patent/CA2814763C/en active Active
- 2012-01-09 ES ES12734573.4T patent/ES2584634T3/es active Active
- 2012-01-09 US US13/346,062 patent/US8569228B2/en active Active
- 2012-01-09 RU RU2013137452A patent/RU2609412C2/ru 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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