JP2013503862A5 - - Google Patents
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- JP2013503862A5 JP2013503862A5 JP2012527871A JP2012527871A JP2013503862A5 JP 2013503862 A5 JP2013503862 A5 JP 2013503862A5 JP 2012527871 A JP2012527871 A JP 2012527871A JP 2012527871 A JP2012527871 A JP 2012527871A JP 2013503862 A5 JP2013503862 A5 JP 2013503862A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- aryl
- alkyl
- hydrogen
- ketone
- 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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- 125000003118 aryl group Chemical group 0.000 claims 37
- 125000003107 substituted aryl group Chemical group 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 36
- 239000001257 hydrogen Substances 0.000 claims 36
- 125000000217 alkyl group Chemical group 0.000 claims 33
- 125000000547 substituted alkyl group Chemical group 0.000 claims 31
- 150000001875 compounds Chemical class 0.000 claims 30
- 125000003710 aryl alkyl group Chemical group 0.000 claims 26
- 150000002431 hydrogen Chemical class 0.000 claims 26
- 125000002252 acyl group Chemical group 0.000 claims 22
- 229940002612 prodrug Drugs 0.000 claims 21
- 239000000651 prodrug Substances 0.000 claims 21
- 150000002576 ketones Chemical class 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 14
- 238000000034 method Methods 0.000 claims 11
- 239000002753 trypsin inhibitor Substances 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 229940122618 Trypsin inhibitor Drugs 0.000 claims 10
- 101710162629 Trypsin inhibitor Proteins 0.000 claims 10
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- 239000004475 Arginine Substances 0.000 claims 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 8
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 229960003121 arginine Drugs 0.000 claims 8
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 8
- 235000009697 arginine Nutrition 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 8
- 235000018977 lysine Nutrition 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 7
- 239000004472 Lysine Substances 0.000 claims 7
- 102000004142 Trypsin Human genes 0.000 claims 7
- 108090000631 Trypsin Proteins 0.000 claims 7
- 150000001721 carbon Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 229960003646 lysine Drugs 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012588 trypsin Substances 0.000 claims 7
- 102000004190 Enzymes Human genes 0.000 claims 5
- 108090000790 Enzymes Proteins 0.000 claims 5
- 239000012453 solvate Substances 0.000 claims 5
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 4
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 4
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 4
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 4
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 4
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 4
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 4
- 239000004473 Threonine Substances 0.000 claims 4
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 4
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 4
- 229960003767 alanine Drugs 0.000 claims 4
- 235000004279 alanine Nutrition 0.000 claims 4
- 229940024606 amino acid Drugs 0.000 claims 4
- 235000001014 amino acid Nutrition 0.000 claims 4
- 150000001413 amino acids Chemical class 0.000 claims 4
- 229960001230 asparagine Drugs 0.000 claims 4
- 235000009582 asparagine Nutrition 0.000 claims 4
- 229960005261 aspartic acid Drugs 0.000 claims 4
- 235000003704 aspartic acid Nutrition 0.000 claims 4
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 4
- 229960002433 cysteine Drugs 0.000 claims 4
- 235000018417 cysteine Nutrition 0.000 claims 4
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 4
- 125000002587 enol group Chemical group 0.000 claims 4
- 229960002989 glutamic acid Drugs 0.000 claims 4
- 235000013922 glutamic acid Nutrition 0.000 claims 4
- 239000004220 glutamic acid Substances 0.000 claims 4
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 4
- 229960002743 glutamine Drugs 0.000 claims 4
- 229960002449 glycine Drugs 0.000 claims 4
- 229960002885 histidine Drugs 0.000 claims 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229960000310 isoleucine Drugs 0.000 claims 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 4
- 229960003136 leucine Drugs 0.000 claims 4
- 229930182817 methionine Natural products 0.000 claims 4
- 229960004452 methionine Drugs 0.000 claims 4
- 229960005190 phenylalanine Drugs 0.000 claims 4
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 4
- 229960002429 proline Drugs 0.000 claims 4
- 229960001153 serine Drugs 0.000 claims 4
- 229960002898 threonine Drugs 0.000 claims 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 4
- 229960004441 tyrosine Drugs 0.000 claims 4
- 239000004474 valine Substances 0.000 claims 4
- 229960004295 valine Drugs 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 3
- 238000013270 controlled release Methods 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 150000008575 L-amino acids Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000037406 food intake Effects 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- 239000002207 metabolite Substances 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 229960004799 tryptophan Drugs 0.000 claims 2
- NMDDZEVVQDPECF-LURJTMIESA-N (2s)-2,7-diaminoheptanoic acid Chemical compound NCCCCC[C@H](N)C(O)=O NMDDZEVVQDPECF-LURJTMIESA-N 0.000 claims 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- QUOGESRFPZDMMT-UHFFFAOYSA-N L-Homoarginine Natural products OC(=O)C(N)CCCCNC(N)=N QUOGESRFPZDMMT-UHFFFAOYSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims 1
- QUOGESRFPZDMMT-YFKPBYRVSA-N L-homoarginine Chemical compound OC(=O)[C@@H](N)CCCCNC(N)=N QUOGESRFPZDMMT-YFKPBYRVSA-N 0.000 claims 1
- 150000001483 arginine derivatives Chemical class 0.000 claims 1
- 229960004203 carnitine Drugs 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000002532 enzyme inhibitor Substances 0.000 claims 1
- 229940125532 enzyme inhibitor Drugs 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 150000002669 lysines Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24061109P | 2009-09-08 | 2009-09-08 | |
| US61/240,611 | 2009-09-08 | ||
| US28814809P | 2009-12-18 | 2009-12-18 | |
| US61/288,148 | 2009-12-18 | ||
| PCT/US2010/031956 WO2011031350A1 (en) | 2009-09-08 | 2010-04-21 | Compositions comprising enzyme-cleavable ketone-modified opioid prodrugs and optional inhibitors thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015190867A Division JP2016041698A (ja) | 2009-09-08 | 2015-09-29 | 酵素切断可能なケトン修飾オピオイドプロドラッグとその任意選択のインヒビターとを含んでなる組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013503862A JP2013503862A (ja) | 2013-02-04 |
| JP2013503862A5 true JP2013503862A5 (enExample) | 2013-06-06 |
Family
ID=43732738
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012527871A Pending JP2013503862A (ja) | 2009-09-08 | 2010-04-21 | 酵素切断可能なケトン修飾オピオイドプロドラッグとその任意選択のインヒビターとを含んでなる組成物 |
| JP2015190867A Pending JP2016041698A (ja) | 2009-09-08 | 2015-09-29 | 酵素切断可能なケトン修飾オピオイドプロドラッグとその任意選択のインヒビターとを含んでなる組成物 |
| JP2018100108A Active JP6778234B2 (ja) | 2009-09-08 | 2018-05-25 | 酵素切断可能なケトン修飾オピオイドプロドラッグとその任意選択のインヒビターとを含んでなる組成物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015190867A Pending JP2016041698A (ja) | 2009-09-08 | 2015-09-29 | 酵素切断可能なケトン修飾オピオイドプロドラッグとその任意選択のインヒビターとを含んでなる組成物 |
| JP2018100108A Active JP6778234B2 (ja) | 2009-09-08 | 2018-05-25 | 酵素切断可能なケトン修飾オピオイドプロドラッグとその任意選択のインヒビターとを含んでなる組成物 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US9493477B2 (enExample) |
| EP (1) | EP2475429B1 (enExample) |
| JP (3) | JP2013503862A (enExample) |
| CN (1) | CN102695545B (enExample) |
| AU (1) | AU2010293028B2 (enExample) |
| BR (1) | BR112012005124B1 (enExample) |
| CA (1) | CA2773340C (enExample) |
| IL (1) | IL218498A (enExample) |
| MX (1) | MX348262B (enExample) |
| PH (1) | PH12012500485A1 (enExample) |
| RU (1) | RU2600736C2 (enExample) |
| SG (1) | SG179026A1 (enExample) |
| WO (1) | WO2011031350A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9493477B2 (en) * | 2009-09-08 | 2016-11-15 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable ketone-modified opioid prodrugs and optional inhibitors thereof |
| US20110262355A1 (en) | 2010-04-21 | 2011-10-27 | Jenkins Thomas E | Compositions comprising enzyme-cleavable opioid prodrugs and inhibitors thereof |
| EP2560489A4 (en) * | 2010-04-21 | 2014-01-22 | Signature Therapeutics Inc | COMPOSITIONS WITH ENZYMSPALTBAR OPIOID PRODRUGS AND HEMMER FOR THIS |
| US20130059914A1 (en) | 2010-04-21 | 2013-03-07 | Signature Therapeutics, Inc. | Compositions Comprising Enzyme-Cleavable Amphetamine Prodrugs and Inhibitors Thereof |
| CA2798884C (en) | 2010-05-10 | 2016-09-13 | Euro-Celtique S.A. | Manufacturing of active-free granules and tablets comprising the same |
| MX347105B (es) | 2010-05-10 | 2017-04-12 | Euro Celtique Sa | Composiciones farmaceuticas que comprenden hidromorfona y naloxona. |
| CA2798885C (en) | 2010-05-10 | 2014-11-18 | Euro-Celtique S.A. | Combination of active loaded granules with additional actives |
| BR112013017296B1 (pt) | 2011-01-11 | 2021-02-17 | Signature Therapeutics, Inc. | composto e composição compreendendo oxicodona, método para reduzir o abuso potencial da referida composição, unidade de dose e método para a sua preparação, e método para identificar um composto e um inibidor de tripsina |
| US8685916B2 (en) | 2011-03-09 | 2014-04-01 | Signature Therapeutics, 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 |
| EP2760844B1 (fr) * | 2011-09-29 | 2018-11-21 | Ecole Normale Superieure De Lyon | Substrat de peptidase fluorogene |
| KR101589846B1 (ko) | 2011-10-26 | 2016-01-28 | 켐팜 인코포레이티드 | 히드로모르폰의 벤조산, 벤조산 유도체 및 헤테로아릴 카르복실산 컨쥬게이트, 전구약물, 이의 제조 방법 및 용도 |
| EP3068397A1 (en) | 2013-11-13 | 2016-09-21 | Euro-Celtique S.A. | Hydromorphone and naloxone for treatment of pain and opioid bowel dysfunction syndrome |
| EP3077008B1 (en) | 2013-12-06 | 2023-10-04 | Jie Han | Bioreversable promoieties for nitrogen-containing and hydroxyl-containing drugs |
| BR112017011764A2 (pt) | 2014-12-02 | 2018-07-10 | Kempharm, Inc. | ácido benzóico, derivados de ácido benzóico e conjugados de ácido heteroaril carboxílico de oximorfona, pro-fármacos, métodos e preparação e uso dos mesmos |
| PT3713939T (pt) * | 2017-11-24 | 2021-09-16 | Byondis Bv | Processo melhorado para a síntese de fármaco ligante vcseco- duba |
| US10807995B2 (en) | 2018-07-13 | 2020-10-20 | Alkermes Pharma Ireland Limited | Thienothiophene compounds for long-acting injectable compositions and related methods |
| US10799496B2 (en) | 2018-07-13 | 2020-10-13 | Alkermes Pharma Ireland Limited | Naphthylenyl compounds for long-acting injectable compositions and related methods |
| US10717712B2 (en) * | 2018-07-27 | 2020-07-21 | Concentric Analgesics, Inc. | Pegylated prodrugs of phenolic TRPV1 agonists |
| US10975099B2 (en) | 2018-11-05 | 2021-04-13 | Alkermes Pharma Ireland Limited | Thiophene compounds for long-acting injectable compositions and related methods |
| CN113624665A (zh) * | 2021-07-30 | 2021-11-09 | 中国药科大学 | 一种抗肿瘤候选化合物在治疗结直肠癌药物中的应用及测定方法 |
| CA3230025A1 (en) | 2021-09-29 | 2023-04-06 | Lynn Kirkpatrick | Enzyme-cleavable methadone prodrugs and methods of use thereof |
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