CA3104099A1 - Acetate salt of buprenorphine and methods for preparing buprenorphine - Google Patents
Acetate salt of buprenorphine and methods for preparing buprenorphineInfo
- Publication number
- CA3104099A1 CA3104099A1 CA3104099A CA3104099A CA3104099A1 CA 3104099 A1 CA3104099 A1 CA 3104099A1 CA 3104099 A CA3104099 A CA 3104099A CA 3104099 A CA3104099 A CA 3104099A CA 3104099 A1 CA3104099 A1 CA 3104099A1
- Authority
- CA
- Canada
- Prior art keywords
- buprenorphine
- product
- admixture
- free base
- acetate salt
- 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
- 238000000034 method Methods 0.000 title claims abstract description 238
- 229960001736 buprenorphine Drugs 0.000 title claims abstract description 233
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 title claims abstract description 206
- 159000000021 acetate salts Chemical class 0.000 title claims abstract description 102
- 239000012458 free base Substances 0.000 claims abstract description 98
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 33
- 239000012535 impurity Substances 0.000 claims abstract description 12
- 239000000047 product Substances 0.000 claims description 135
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 77
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 239000000243 solution Substances 0.000 claims description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 36
- 238000001914 filtration Methods 0.000 claims description 35
- -1 buprenorphine acetate salt Chemical class 0.000 claims description 32
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 32
- 239000012296 anti-solvent Substances 0.000 claims description 30
- 208000002193 Pain Diseases 0.000 claims description 28
- 241001465754 Metazoa Species 0.000 claims description 26
- 239000007864 aqueous solution Substances 0.000 claims description 25
- 239000013078 crystal Substances 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 230000005855 radiation Effects 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 12
- 238000004090 dissolution Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 230000007704 transition Effects 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000002244 precipitate Substances 0.000 claims description 10
- 239000006184 cosolvent Substances 0.000 claims description 8
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- 239000003814 drug Substances 0.000 claims description 7
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 6
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- 150000004685 tetrahydrates Chemical class 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
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- 239000010452 phosphate Substances 0.000 claims description 4
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- 150000004678 hydrides Chemical class 0.000 claims description 2
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- 239000012453 solvate Substances 0.000 abstract description 11
- 150000004677 hydrates Chemical class 0.000 abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
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- DJTZIDSZSYWGKR-UHFFFAOYSA-N acetic acid tetrahydrate Chemical compound O.O.O.O.CC(O)=O DJTZIDSZSYWGKR-UHFFFAOYSA-N 0.000 description 8
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- 239000007848 Bronsted acid Substances 0.000 description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000004686 pentahydrates Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 description 1
- 229930003945 thebaine Natural products 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 238000001845 vibrational spectrum Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
- C07D489/09—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems
- C07D489/10—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14
- C07D489/12—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: containing 4aH-8, 9 c-Iminoethano- phenanthro [4, 5-b, c, d] furan ring systems condensed with carbocyclic rings or ring systems with a bridge between positions 6 and 14 the bridge containing only two carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/485—Morphinan derivatives, e.g. morphine, codeine
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562131114P | 2015-03-10 | 2015-03-10 | |
| US62/131,114 | 2015-03-10 | ||
| CA2977732A CA2977732C (en) | 2015-03-10 | 2016-03-09 | Acetate salt of buprenorphine and methods for preparing buprenorphine |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2977732A Division CA2977732C (en) | 2015-03-10 | 2016-03-09 | Acetate salt of buprenorphine and methods for preparing buprenorphine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3104099A1 true CA3104099A1 (en) | 2016-09-15 |
Family
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| CA3104099A Abandoned CA3104099A1 (en) | 2015-03-10 | 2016-03-09 | Acetate salt of buprenorphine and methods for preparing buprenorphine |
| CA2977732A Expired - Fee Related CA2977732C (en) | 2015-03-10 | 2016-03-09 | Acetate salt of buprenorphine and methods for preparing buprenorphine |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2977732A Expired - Fee Related CA2977732C (en) | 2015-03-10 | 2016-03-09 | Acetate salt of buprenorphine and methods for preparing buprenorphine |
Country Status (19)
| Country | Link |
|---|---|
| US (6) | US10406152B2 (enExample) |
| EP (1) | EP3283490A1 (enExample) |
| JP (2) | JP6660399B2 (enExample) |
| KR (2) | KR20200045010A (enExample) |
| CN (1) | CN107660207B (enExample) |
| AR (1) | AR103902A1 (enExample) |
| AU (2) | AU2016230750B2 (enExample) |
| BR (1) | BR112017019357A2 (enExample) |
| CA (2) | CA3104099A1 (enExample) |
| CO (1) | CO2017009130A2 (enExample) |
| EA (1) | EA201792014A1 (enExample) |
| IL (1) | IL254384A0 (enExample) |
| MA (1) | MA45902A (enExample) |
| MX (1) | MX2017011606A (enExample) |
| NZ (1) | NZ735736A (enExample) |
| PH (1) | PH12017501641A1 (enExample) |
| SG (1) | SG11201707350TA (enExample) |
| TW (2) | TW202037597A (enExample) |
| WO (1) | WO2016142877A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9534241B2 (en) | 2013-03-15 | 2017-01-03 | The Board Of Trustees Of The Leland Stanford Junior University | Benzylisoquinoline alkaloids (BIA) producing microbes, and methods of making and using the same |
| US11124814B2 (en) | 2013-11-04 | 2021-09-21 | The Board Of Trustees Of The Leland Stanford Junior University | Benzylisoquinoline alkaloid (BIA) precursor producing microbes, and methods of making and using the same |
| SG11201707350TA (en) * | 2015-03-10 | 2017-10-30 | Rhodes Tech | Acetate salt of buprenorphine and methods for preparing buprenorphine |
| CN107614688B (zh) | 2015-05-04 | 2023-02-28 | 小利兰·斯坦福大学托管委员会 | 产生苄基异喹啉生物碱(bia)前体的微生物及其制备和使用方法 |
| WO2016183023A1 (en) | 2015-05-08 | 2016-11-17 | The Board Of Trustees Of The Leland Stanford Junior University | Methods of producing epimerases and benzylisoquinoline alkaloids |
| EP3529355A4 (en) | 2016-10-18 | 2020-07-08 | Antheia, Inc. | PROCESSES FOR THE PRODUCTION OF NOR-OPIOID AND NAL-OPIOID BENZYLISOQUINOLINE ALKALOIDS |
| BR112020002050A2 (pt) | 2017-08-03 | 2020-09-08 | Antheia, Inc. | epimerases engenheiradas alcaloides benzilisoquinolina e métodos de produção de alcaloides benzilisoquinolina |
| CA3089256C (en) * | 2018-05-11 | 2023-10-10 | Alar Pharmaceuticals Inc. | Long-acting injectable formulations and crystalline forms of buprenorphine derivatives |
| CN113784758B (zh) | 2019-03-08 | 2025-03-07 | 小利兰·斯坦福大学托管委员会 | 产生莨菪烷生物碱(ta)的非植物宿主细胞及其制备和使用方法 |
| JP2025520773A (ja) * | 2022-06-24 | 2025-07-03 | ▲ユ▼展新藥生技股分有限公司 | ブプレノルフィンの安定した医薬組成物並びにその調製方法及び使用 |
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| US3355486A (en) | 1965-01-08 | 1967-11-28 | Fmc Corp | Continuous process of synthesizing amino-iminomethane-sulfinic acid |
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| CA2002299A1 (en) * | 1988-11-10 | 1990-05-10 | Eugene G. Drust | Compositions for the transdermal delivery of buprenorphine salts |
| IT1229203B (it) | 1989-03-22 | 1991-07-25 | Bioresearch Spa | Impiego di acido 5 metiltetraidrofolico, di acido 5 formiltetraidrofolico e dei loro sali farmaceuticamente accettabili per la preparazione di composizioni farmaceutiche in forma a rilascio controllato attive nella terapia dei disturbi mentali organici e composizioni farmaceutiche relative. |
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| CA2896919C (en) * | 2012-12-31 | 2019-01-29 | Rhodes Technologies | Process for preparing 7.beta.-substituted 6.alpha.,14.alpha.-ethenomorphinans and 7.beta.-substituted 6.alpha.,14.alpha.-ethanomorphinans |
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-
2016
- 2016-03-09 SG SG11201707350TA patent/SG11201707350TA/en unknown
- 2016-03-09 CA CA3104099A patent/CA3104099A1/en not_active Abandoned
- 2016-03-09 EA EA201792014A patent/EA201792014A1/ru unknown
- 2016-03-09 CN CN201680027202.2A patent/CN107660207B/zh not_active Expired - Fee Related
- 2016-03-09 NZ NZ735736A patent/NZ735736A/en not_active IP Right Cessation
- 2016-03-09 KR KR1020207011729A patent/KR20200045010A/ko not_active Ceased
- 2016-03-09 MX MX2017011606A patent/MX2017011606A/es unknown
- 2016-03-09 MA MA045902A patent/MA45902A/fr unknown
- 2016-03-09 US US15/507,453 patent/US10406152B2/en active Active
- 2016-03-09 KR KR1020177028535A patent/KR20170137738A/ko not_active Ceased
- 2016-03-09 WO PCT/IB2016/051332 patent/WO2016142877A1/en not_active Ceased
- 2016-03-09 CA CA2977732A patent/CA2977732C/en not_active Expired - Fee Related
- 2016-03-09 EP EP16709607.2A patent/EP3283490A1/en not_active Withdrawn
- 2016-03-09 BR BR112017019357A patent/BR112017019357A2/pt not_active IP Right Cessation
- 2016-03-09 JP JP2017547399A patent/JP6660399B2/ja not_active Expired - Fee Related
- 2016-03-09 AU AU2016230750A patent/AU2016230750B2/en not_active Ceased
- 2016-03-10 AR ARP160100641A patent/AR103902A1/es unknown
- 2016-03-10 TW TW109106564A patent/TW202037597A/zh unknown
- 2016-03-10 TW TW105107434A patent/TWI699367B/zh not_active IP Right Cessation
-
2017
- 2017-03-01 US US15/446,197 patent/US9926329B2/en active Active
- 2017-09-07 IL IL254384A patent/IL254384A0/en unknown
- 2017-09-07 CO CONC2017/0009130A patent/CO2017009130A2/es unknown
- 2017-09-08 PH PH12017501641A patent/PH12017501641A1/en unknown
-
2018
- 2018-02-12 US US15/894,520 patent/US10278967B2/en active Active
-
2019
- 2019-05-10 AU AU2019203308A patent/AU2019203308A1/en not_active Abandoned
- 2019-06-19 US US16/446,397 patent/US10874662B2/en active Active
- 2019-06-19 US US16/446,373 patent/US10835528B2/en active Active
- 2019-10-10 JP JP2019186901A patent/JP2020033359A/ja active Pending
-
2020
- 2020-10-29 US US17/084,588 patent/US20210046066A1/en not_active Abandoned
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