AU2018261654A1 - Targeted drug rescue with novel compositions, combinations, and methods thereof - Google Patents
Targeted drug rescue with novel compositions, combinations, and methods thereof Download PDFInfo
- Publication number
- AU2018261654A1 AU2018261654A1 AU2018261654A AU2018261654A AU2018261654A1 AU 2018261654 A1 AU2018261654 A1 AU 2018261654A1 AU 2018261654 A AU2018261654 A AU 2018261654A AU 2018261654 A AU2018261654 A AU 2018261654A AU 2018261654 A1 AU2018261654 A1 AU 2018261654A1
- Authority
- AU
- Australia
- Prior art keywords
- phenoxy
- methyl
- oxy
- propan
- dimethylamino
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 143
- 238000000034 method Methods 0.000 title claims abstract description 91
- 239000003814 drug Substances 0.000 title description 51
- 229940079593 drug Drugs 0.000 title description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 370
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 239000002253 acid Substances 0.000 claims abstract description 48
- 229940002612 prodrug Drugs 0.000 claims abstract description 47
- 239000000651 prodrug Substances 0.000 claims abstract description 47
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 33
- 239000002207 metabolite Substances 0.000 claims abstract description 26
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 3
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 claims abstract 2
- 108010001237 Cytochrome P-450 CYP2D6 Proteins 0.000 claims abstract 2
- 102100021704 Cytochrome P450 2D6 Human genes 0.000 claims abstract 2
- 101150013372 Htr2c gene Proteins 0.000 claims abstract 2
- 229960001985 dextromethorphan Drugs 0.000 claims description 184
- -1 (1-(dimethylamino) -3-(2-(3-methoxyphenethyl) phenoxy) propan-2-yl) oxy Chemical group 0.000 claims description 169
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 152
- 230000000694 effects Effects 0.000 claims description 63
- QOBGWWQAMAPULA-RLLQIKCJSA-N n,n-dimethyl-2-[[(1r,3s,4r)-4,7,7-trimethyl-3-phenyl-3-bicyclo[2.2.1]heptanyl]oxy]ethanamine Chemical compound C1([C@@]2([C@]3(C)CC[C@@H](C3(C)C)C2)OCCN(C)C)=CC=CC=C1 QOBGWWQAMAPULA-RLLQIKCJSA-N 0.000 claims description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 56
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 claims description 54
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- 239000002469 receptor inverse agonist Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
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- 239000002400 serotonin 2A antagonist Substances 0.000 claims description 41
- 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 claims description 37
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 claims description 34
- 229940125425 inverse agonist Drugs 0.000 claims description 32
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
- 230000036470 plasma concentration Effects 0.000 claims description 31
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 30
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- 125000003118 aryl group Chemical group 0.000 claims description 23
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 21
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 21
- 208000007220 Cytochrome P-450 CYP2D6 Inhibitors Diseases 0.000 claims description 20
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- 101150104779 HTR2A gene Proteins 0.000 claims description 18
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 18
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 18
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 18
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 18
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 17
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
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- QIVBCDIJIAJPQS-UHFFFAOYSA-M tryptophanate Chemical compound C1=CC=C2C(CC(N)C([O-])=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-M 0.000 claims description 15
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 14
- 229960000836 amitriptyline Drugs 0.000 claims description 14
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 claims description 14
- 229960004801 imipramine Drugs 0.000 claims description 14
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 claims description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 13
- 229940068372 acetyl salicylate Drugs 0.000 claims description 13
- 229930195712 glutamate Natural products 0.000 claims description 13
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 13
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 13
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims description 13
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims description 12
- RGHNJXZEOKUKBD-MGCNEYSASA-N D-galactonic acid Chemical compound OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-MGCNEYSASA-N 0.000 claims description 12
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- RGHNJXZEOKUKBD-MBMOQRBOSA-N D-mannonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-MBMOQRBOSA-N 0.000 claims description 12
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- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 claims description 12
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
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- 125000000217 alkyl group Chemical group 0.000 claims description 10
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- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 claims description 10
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Landscapes
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| EP3708168A3 (en) * | 2014-09-14 | 2020-12-09 | Avanir Pharmaceuticals, Inc. | Combinations of deuterated dextromethorphan and quinidine for the treatment of agitation in dementia |
| RU2764716C2 (ru) * | 2016-08-26 | 2022-01-19 | Экссива Уг (Хафтунгзбешрэнкт) | Композиции и связанные с ними способы |
| WO2018204713A1 (en) * | 2017-05-04 | 2018-11-08 | Exciva Ug (Haftungsbeschränkt) | Targeted drug rescue with novel compositions, combinations, and methods thereof |
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| JP7514078B2 (ja) | 2024-07-10 |
| IL270326B (en) | 2022-10-01 |
| ZA201908006B (en) | 2021-04-28 |
| EP3618819A1 (en) | 2020-03-11 |
| CA3062452C (en) | 2023-10-24 |
| CA3138116A1 (en) | 2018-11-08 |
| JP2020518617A (ja) | 2020-06-25 |
| IL270326A (enrdf_load_stackoverflow) | 2018-05-03 |
| KR20200062078A (ko) | 2020-06-03 |
| CN110831584B (zh) | 2023-03-10 |
| CA3062452A1 (en) | 2018-11-08 |
| RU2019137004A3 (enrdf_load_stackoverflow) | 2021-06-04 |
| RU2019137004A (ru) | 2021-06-04 |
| RU2760558C2 (ru) | 2021-11-29 |
| IL270326B2 (en) | 2023-02-01 |
| RU2760558C9 (ru) | 2022-02-22 |
| AU2021215274B2 (en) | 2022-11-03 |
| JP2023143940A (ja) | 2023-10-06 |
| MA49464A (fr) | 2020-04-29 |
| BR112019022902A2 (pt) | 2020-05-19 |
| TW201842902A (zh) | 2018-12-16 |
| CN110831584A (zh) | 2020-02-21 |
| KR20210130827A (ko) | 2021-11-01 |
| WO2018204713A1 (en) | 2018-11-08 |
| EP3618819A4 (en) | 2021-01-20 |
| TWI787260B (zh) | 2022-12-21 |
| AU2021215274A1 (en) | 2021-09-02 |
| KR102444803B1 (ko) | 2022-09-19 |
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