KR20200062078A - 신규 조성물, 조합 및 그의 방법을 갖는 표적 약물 구제 - Google Patents
신규 조성물, 조합 및 그의 방법을 갖는 표적 약물 구제 Download PDFInfo
- Publication number
- KR20200062078A KR20200062078A KR1020197035796A KR20197035796A KR20200062078A KR 20200062078 A KR20200062078 A KR 20200062078A KR 1020197035796 A KR1020197035796 A KR 1020197035796A KR 20197035796 A KR20197035796 A KR 20197035796A KR 20200062078 A KR20200062078 A KR 20200062078A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- phenoxy
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 143
- 238000000034 method Methods 0.000 title claims abstract description 86
- 239000003814 drug Substances 0.000 title claims description 79
- 229940079593 drug Drugs 0.000 title claims description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 363
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 239000002253 acid Substances 0.000 claims abstract description 51
- 229940002612 prodrug Drugs 0.000 claims abstract description 50
- 239000000651 prodrug Substances 0.000 claims abstract description 50
- 239000002207 metabolite Substances 0.000 claims abstract description 44
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- 239000003446 ligand Substances 0.000 claims abstract description 3
- 108010001237 Cytochrome P-450 CYP2D6 Proteins 0.000 claims abstract 2
- 102100021704 Cytochrome P450 2D6 Human genes 0.000 claims abstract 2
- -1 acyl radical Chemical class 0.000 claims description 218
- 229960001985 dextromethorphan Drugs 0.000 claims description 177
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- 230000000694 effects Effects 0.000 claims description 81
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 239000002469 receptor inverse agonist Substances 0.000 claims description 56
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- 230000001965 increasing effect Effects 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 43
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- 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 21
- 208000007220 Cytochrome P-450 CYP2D6 Inhibitors Diseases 0.000 claims description 20
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- 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
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 17
- 230000009471 action Effects 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 15
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- 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
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- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 13
- 229940068372 acetyl salicylate Drugs 0.000 claims description 13
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 12
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 12
- QIVBCDIJIAJPQS-UHFFFAOYSA-M tryptophanate Chemical compound C1=CC=C2C(CC(N)C([O-])=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-M 0.000 claims description 12
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 11
- 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 11
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 11
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 claims description 11
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 claims description 11
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 11
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- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229960001534 risperidone Drugs 0.000 claims description 11
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 11
- OUYCCCASQSFEME-UHFFFAOYSA-L tyrosinate(2-) Chemical compound [O-]C(=O)C(N)CC1=CC=C([O-])C=C1 OUYCCCASQSFEME-UHFFFAOYSA-L 0.000 claims description 11
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- 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 10
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 10
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- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims description 10
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- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 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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- UENFKOUHHDMVRW-UHFFFAOYSA-N 3-[(3-benzyl-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)oxy]-n,n-dimethylpropan-1-amine Chemical compound C1C(C2(C)C)CCC2(C)C1(OCCCN(C)C)CC1=CC=CC=C1 UENFKOUHHDMVRW-UHFFFAOYSA-N 0.000 claims description 9
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- FBUKVWPVBMHYJY-UHFFFAOYSA-M nonanoate Chemical compound CCCCCCCCC([O-])=O FBUKVWPVBMHYJY-UHFFFAOYSA-M 0.000 claims description 9
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- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 9
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 9
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- 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 8
- QOBGWWQAMAPULA-UHFFFAOYSA-N n,n-dimethyl-2-[(4,7,7-trimethyl-3-phenyl-3-bicyclo[2.2.1]heptanyl)oxy]ethanamine Chemical compound C1C(C2(C)C)CCC2(C)C1(OCCN(C)C)C1=CC=CC=C1 QOBGWWQAMAPULA-UHFFFAOYSA-N 0.000 claims description 8
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- CMIPGOJGVDUUHQ-UHFFFAOYSA-N 3-nitrooxybutanoic acid Chemical compound OC(=O)CC(C)O[N+]([O-])=O CMIPGOJGVDUUHQ-UHFFFAOYSA-N 0.000 claims description 7
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- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 claims description 7
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- OQLWDKJAYSYWTR-UHFFFAOYSA-N n,n-diethyl-3-[(4,7,7-trimethyl-3-phenyl-3-bicyclo[2.2.1]heptanyl)oxy]propan-1-amine Chemical compound C1C(C2(C)C)CCC2(C)C1(OCCCN(CC)CC)C1=CC=CC=C1 OQLWDKJAYSYWTR-UHFFFAOYSA-N 0.000 claims description 6
- FAPWMGQQKQTEIG-UHFFFAOYSA-N n,n-dimethyl-3-[(4,7,7-trimethyl-3-phenyl-3-bicyclo[2.2.1]heptanyl)oxy]propan-1-amine Chemical compound C1C(C2(C)C)CCC2(C)C1(OCCCN(C)C)C1=CC=CC=C1 FAPWMGQQKQTEIG-UHFFFAOYSA-N 0.000 claims description 6
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- VRBKIVRKKCLPHA-UHFFFAOYSA-N nefazodone Chemical compound O=C1N(CCOC=2C=CC=CC=2)C(CC)=NN1CCCN(CC1)CCN1C1=CC=CC(Cl)=C1 VRBKIVRKKCLPHA-UHFFFAOYSA-N 0.000 claims description 6
- WIQRCHMSJFFONW-UHFFFAOYSA-N norfluoxetine Chemical compound C=1C=CC=CC=1C(CCN)OC1=CC=C(C(F)(F)F)C=C1 WIQRCHMSJFFONW-UHFFFAOYSA-N 0.000 claims description 6
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- 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
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
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| TW202102219A (zh) * | 2019-03-18 | 2021-01-16 | 美商艾賓爾製藥公司 | 使用氘化右旋美沙芬(dextromethorphan)及奎尼丁(quinidine)治療精神分裂症之負面徵候之方法 |
| WO2020246143A1 (ja) * | 2019-06-06 | 2020-12-10 | Jsr株式会社 | 感放射線性樹脂組成物、レジストパターン形成方法及び化合物 |
| AU2021276656A1 (en) | 2020-05-19 | 2022-11-24 | Cybin Irl Limited | Deuterated tryptamine derivatives and methods of use |
| CN116473077B (zh) * | 2023-05-08 | 2025-04-11 | 广东方中高新材料有限公司 | 一种n,n配位的镓配合物抗菌剂的合成和应用 |
| CN116473073A (zh) * | 2023-05-08 | 2023-07-25 | 广东方中高新材料有限公司 | 一种含镓配合物的吡唑醚菌酯增效悬浮制剂及其制备方法 |
| CN119432479B (zh) * | 2023-08-04 | 2025-10-03 | 中国石油天然气股份有限公司 | 柴油机润滑油组合物及其制备方法 |
| CN120987847A (zh) * | 2024-11-29 | 2025-11-21 | 江苏恩华药业股份有限公司 | 一种氢溴酸右美沙芬的制备方法 |
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| US4241065A (en) * | 1979-07-02 | 1980-12-23 | E. I. Du Pont De Nemours And Company | Fluoro analogs of hydrocodone and oxycodone useful as analgesics, narcotic antagonists or both |
| US4950658A (en) * | 1988-12-06 | 1990-08-21 | Board Of Trustees Of Southern Illinois Univ. | Method of medical treatment of Alzheimer's disease |
| US5891885A (en) * | 1996-10-09 | 1999-04-06 | Algos Pharmaceutical Corporation | Method for treating migraine |
| US6207674B1 (en) * | 1999-12-22 | 2001-03-27 | Richard A. Smith | Dextromethorphan and oxidase inhibitor for weaning patients from narcotics and anti-depressants |
| US6335371B1 (en) * | 2000-11-28 | 2002-01-01 | Orion Corporation | Method for inducing cognition enhancement |
| TWI326214B (en) * | 2002-07-17 | 2010-06-21 | Avanir Pharmaceuticals Inc | Pharmaceutical compositions comprising dextromethorphan and quinidine for the treatment of neurological disorders |
| US20070099947A1 (en) * | 2005-11-03 | 2007-05-03 | Alkermes, Inc. | Methods and compositions for the treatment of brain reward system disorders by combination therapy |
| MX2008009947A (es) | 2006-02-03 | 2008-10-20 | Avanir Pharmaceuticals | Composiciones farmaceuticas que comprenden dextrometorfano y quinidina para el tratamiento de depresion, ansiedad y trastornos neurodegenerativos. |
| EP2522667B1 (en) * | 2007-05-01 | 2014-08-20 | Concert Pharmaceuticals Inc. | Morphinan compounds |
| AU2008254585B2 (en) * | 2007-05-21 | 2013-09-26 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using quinolinone based atypical antipsychotic agents |
| US8017623B2 (en) * | 2008-07-03 | 2011-09-13 | Trinity Laboratories, Inc. | Dextromethorphan hydrochloride |
| US9737531B2 (en) * | 2012-07-12 | 2017-08-22 | Glytech, Llc | Composition and method for treatment of depression and psychosis in humans |
| EP2964022B1 (en) * | 2013-03-07 | 2019-11-06 | Mindlab LLC | Pain medicine combination and uses thereof |
| CA2907357A1 (en) * | 2013-03-15 | 2014-09-18 | Kinemed, Inc. | Biomarkers |
| SG11201701645WA (en) * | 2014-09-14 | 2017-04-27 | Avanir Pharmaceuticals Inc | Pharmaceutical compositions comprising a dextromethorphan compound and quinidine for the treatment of agitation in dementia |
| JP7096813B2 (ja) * | 2016-08-26 | 2022-07-06 | エクシーバ ゲーエムベーハー | 組成物及びその方法 |
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| KR20210130827A (ko) | 2021-11-01 |
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| CA3062452C (en) | 2023-10-24 |
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| TWI787260B (zh) | 2022-12-21 |
| RU2760558C9 (ru) | 2022-02-22 |
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| WO2018204713A1 (en) | 2018-11-08 |
| IL270326A (enExample) | 2018-05-03 |
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| CN110831584A (zh) | 2020-02-21 |
| TW201842902A (zh) | 2018-12-16 |
| EP3618819A1 (en) | 2020-03-11 |
| MA49464A (fr) | 2020-04-29 |
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