CA2855990A1 - Sulfate esters of noribogaine - Google Patents
Sulfate esters of noribogaine Download PDFInfo
- Publication number
- CA2855990A1 CA2855990A1 CA2855990A CA2855990A CA2855990A1 CA 2855990 A1 CA2855990 A1 CA 2855990A1 CA 2855990 A CA2855990 A CA 2855990A CA 2855990 A CA2855990 A CA 2855990A CA 2855990 A1 CA2855990 A1 CA 2855990A1
- Authority
- CA
- Canada
- Prior art keywords
- noribogaine
- compound
- hydrogen
- patient
- pain
- 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
- 150000003467 sulfuric acid derivatives Chemical class 0.000 title abstract description 5
- RAUCDOKTMDOIPF-UHFFFAOYSA-N hydroxyibogamine Natural products CCC1CC(C2)CC3C1N2CCC1=C3NC2=CC=C(O)C=C12 RAUCDOKTMDOIPF-UHFFFAOYSA-N 0.000 title description 40
- RAUCDOKTMDOIPF-RYRUWHOVSA-N noribogaine Chemical compound N1([C@@H]2[C@H]3C[C@H](C1)C[C@@H]2CC)CCC1=C3NC2=CC=C(O)C=C12 RAUCDOKTMDOIPF-RYRUWHOVSA-N 0.000 title description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 208000002193 Pain Diseases 0.000 claims abstract description 16
- 230000036407 pain Effects 0.000 claims abstract description 15
- 206010012335 Dependence Diseases 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- -1 noribogaine sulfate ester Chemical class 0.000 description 21
- 125000006239 protecting group Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229940079593 drug Drugs 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 10
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- 208000024891 symptom Diseases 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
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- 125000000524 functional group Chemical group 0.000 description 6
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- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
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- HSIBGVUMFOSJPD-CFDPKNGZSA-N ibogaine Chemical class N1([C@@H]2[C@H]3C[C@H](C1)C[C@@H]2CC)CCC1=C3NC2=CC=C(OC)C=C12 HSIBGVUMFOSJPD-CFDPKNGZSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000001690 micro-dialysis Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 230000019635 sulfation Effects 0.000 description 4
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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 description 3
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- VOXIUXZAOFEFBL-UHFFFAOYSA-N Voacangin Natural products CCC1CC2CN3CC1C(C2)(OC(=O)C)c4[nH]c5ccc(OC)cc5c4C3 VOXIUXZAOFEFBL-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- OLOCMRXSJQJJPL-UHFFFAOYSA-N ibogaine Natural products CCC1CC2CC3C1N(C2)C=Cc4c3[nH]c5ccc(OC)cc45 OLOCMRXSJQJJPL-UHFFFAOYSA-N 0.000 description 3
- AREITJMUSRHSBK-UHFFFAOYSA-N ibogamine Natural products CCC1CC2C3CC1CN2CCc4c3[nH]c5ccccc45 AREITJMUSRHSBK-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229960001797 methadone Drugs 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000008693 nausea Effects 0.000 description 3
- 229960003753 nitric oxide Drugs 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 2
- 206010008479 Chest Pain Diseases 0.000 description 2
- 208000002881 Colic Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010016275 Fear Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- 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
-
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161569144P | 2011-12-09 | 2011-12-09 | |
| US61/569,144 | 2011-12-09 | ||
| PCT/US2012/067627 WO2013085849A2 (en) | 2011-12-09 | 2012-12-03 | Sulfate esters of noribogaine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2855990A1 true CA2855990A1 (en) | 2013-06-13 |
Family
ID=48575046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2855990A Abandoned CA2855990A1 (en) | 2011-12-09 | 2012-12-03 | Sulfate esters of noribogaine |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8853201B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2788356A4 (cg-RX-API-DMAC7.html) |
| JP (2) | JP2015509075A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2855990A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2013085849A2 (cg-RX-API-DMAC7.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9045481B2 (en) * | 2012-12-20 | 2015-06-02 | Demerx, Inc. | Substituted noribogaine |
| US9783535B2 (en) | 2012-12-20 | 2017-10-10 | Demerx, Inc. | Substituted noribogaine |
| CA3256416A1 (en) * | 2013-03-15 | 2025-06-21 | Demerx, Inc. | METHOD FOR THE TREATMENT OF ADDICTION IN PATIENTS UNDER METHADONE WITH NORIBOGAINE |
| JP6462663B2 (ja) | 2013-04-12 | 2019-01-30 | アイカーン スクール オブ メディシン アット マウント シナイ | 心的外傷後ストレス障害を処置するための方法 |
| US9561232B2 (en) | 2014-02-18 | 2017-02-07 | Demerx, Inc. | Low dose noribogaine for treating nicotine addiction and preventing relapse of nicotine use |
| US9591978B2 (en) | 2014-03-13 | 2017-03-14 | Demerx, Inc. | Methods and compositions for pre-screening patients for treatment with noribogaine |
| US9549935B2 (en) | 2014-07-14 | 2017-01-24 | Demerx, Inc. | Methods and compositions for treating migraines using noribogaine |
| EP3845275A1 (en) | 2014-11-26 | 2021-07-07 | DemeRx, Inc. | Methods and compositions for potentiating the action of opioid analgesics using iboga alkaloids |
| WO2016134019A1 (en) * | 2015-02-19 | 2016-08-25 | Demerx, Inc. | Methods for treating disorders associated with undesired activity of neuronal nicotinic acetylcholine receptors |
| GB2571696B (en) | 2017-10-09 | 2020-05-27 | Compass Pathways Ltd | Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| KR20220009954A (ko) | 2019-04-17 | 2022-01-25 | 컴퍼스 패쓰파인더 리미티드 | 신경인지 장애, 만성 통증을 치료하고 염증을 감소시키는 방법 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2813873A (en) * | 1957-11-19 | Derivatives of the ibogaine alkaloids | ||
| US4626539A (en) | 1984-08-10 | 1986-12-02 | E. I. Dupont De Nemours And Company | Trandermal delivery of opioids |
| US4806341A (en) | 1985-02-25 | 1989-02-21 | Rutgers, The State University Of New Jersey | Transdermal absorption dosage unit for narcotic analgesics and antagonists and process for administration |
| JPH0615546B2 (ja) * | 1986-02-24 | 1994-03-02 | 株式会社ヤクルト本社 | 新規なカンプトテシン誘導体 |
| US5149538A (en) | 1991-06-14 | 1992-09-22 | Warner-Lambert Company | Misuse-resistive transdermal opioid dosage form |
| ES2264562T3 (es) * | 1994-07-25 | 2007-01-01 | Nda International, Inc. | Uso de derivados de noribogaina para tratar la dependencia quimica en mamiferos. |
| WO1997005869A1 (en) * | 1995-08-08 | 1997-02-20 | Albany Medical College | Ibogamine congeners |
| US5616575A (en) * | 1995-12-04 | 1997-04-01 | Regents Of The University Of Minnesota | Bioactive tricyclic ibogaine analogs |
| US7220737B1 (en) | 1997-09-04 | 2007-05-22 | Novoneuron, Inc | Noribogaine in the treatment of pain and drug addiction |
| EP2338494B1 (en) * | 1997-09-04 | 2013-07-10 | DemeRx, Inc. | Noribogaine in the treatment of pain and drug addiction |
| AR073701A1 (es) * | 2008-09-29 | 2010-11-24 | Abbott Lab | Derivados de indol y de indolicina, metodos para su preparacion, una composicion farmaceutica que los comprende y su uso en el tratamiento de enfermedades neurodegenerativas. |
-
2012
- 2012-12-03 WO PCT/US2012/067627 patent/WO2013085849A2/en not_active Ceased
- 2012-12-03 CA CA2855990A patent/CA2855990A1/en not_active Abandoned
- 2012-12-03 EP EP12855158.7A patent/EP2788356A4/en not_active Withdrawn
- 2012-12-03 JP JP2014545968A patent/JP2015509075A/ja active Pending
- 2012-12-07 US US13/708,844 patent/US8853201B2/en active Active
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2017
- 2017-08-24 JP JP2017161033A patent/JP2017203046A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP2788356A2 (en) | 2014-10-15 |
| JP2017203046A (ja) | 2017-11-16 |
| EP2788356A4 (en) | 2015-10-21 |
| JP2015509075A (ja) | 2015-03-26 |
| US8853201B2 (en) | 2014-10-07 |
| US20130165425A1 (en) | 2013-06-27 |
| WO2013085849A3 (en) | 2014-12-18 |
| WO2013085849A2 (en) | 2013-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20171205 |