CA2855994A1 - Phosphate esters of noribogaine - Google Patents
Phosphate esters of noribogaine Download PDFInfo
- Publication number
- CA2855994A1 CA2855994A1 CA2855994A CA2855994A CA2855994A1 CA 2855994 A1 CA2855994 A1 CA 2855994A1 CA 2855994 A CA2855994 A CA 2855994A CA 2855994 A CA2855994 A CA 2855994A CA 2855994 A1 CA2855994 A1 CA 2855994A1
- Authority
- CA
- Canada
- Prior art keywords
- hydrogen
- noribogaine
- compound
- monophosphate
- formula
- 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
- 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 abstract description 53
- RAUCDOKTMDOIPF-UHFFFAOYSA-N hydroxyibogamine Natural products CCC1CC(C2)CC3C1N2CCC1=C3NC2=CC=C(O)C=C12 RAUCDOKTMDOIPF-UHFFFAOYSA-N 0.000 title abstract description 52
- 150000003014 phosphoric acid esters Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 35
- 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 14
- 206010012335 Dependence Diseases 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 30
- 150000004712 monophosphates Chemical class 0.000 claims description 22
- 239000001177 diphosphate Substances 0.000 claims description 20
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 20
- 235000011180 diphosphates Nutrition 0.000 claims description 20
- 239000001226 triphosphate Substances 0.000 claims description 20
- 235000011178 triphosphate Nutrition 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 16
- 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 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 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 150000002148 esters Chemical class 0.000 abstract description 14
- -1 phosphate ester Chemical class 0.000 description 22
- 229910019142 PO4 Inorganic materials 0.000 description 18
- 239000010452 phosphate Substances 0.000 description 18
- 235000021317 phosphate Nutrition 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000006239 protecting group Chemical group 0.000 description 15
- 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 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 208000028173 post-traumatic stress disease Diseases 0.000 description 10
- 208000024891 symptom Diseases 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 8
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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
- 201000010099 disease Diseases 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 5
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 5
- 208000014674 injury Diseases 0.000 description 5
- 230000015654 memory Effects 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000008733 trauma Effects 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 206010019233 Headaches Diseases 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 206010013663 drug dependence Diseases 0.000 description 4
- 230000002996 emotional effect Effects 0.000 description 4
- 231100000869 headache Toxicity 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 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
- 238000001727 in vivo Methods 0.000 description 4
- 238000001690 micro-dialysis Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 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
- 230000035882 stress Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010022998 Irritability Diseases 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 206010028813 Nausea Diseases 0.000 description 3
- 208000001294 Nociceptive Pain Diseases 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-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
- 230000000903 blocking effect Effects 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 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
- 235000019359 magnesium stearate Nutrition 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
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-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
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- 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
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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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- DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 description 2
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- C07F9/02—Phosphorus compounds
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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
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Anesthesiology (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 |
|---|---|---|---|
| US201161569150P | 2011-12-09 | 2011-12-09 | |
| US61/569,150 | 2011-12-09 | ||
| PCT/US2012/067799 WO2013085922A1 (en) | 2011-12-09 | 2012-12-04 | Phosphate esters of noribogaine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2855994A1 true CA2855994A1 (en) | 2013-06-13 |
Family
ID=48574807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2855994A Abandoned CA2855994A1 (en) | 2011-12-09 | 2012-12-04 | Phosphate esters of noribogaine |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9051343B2 (enExample) |
| EP (1) | EP2788003A4 (enExample) |
| JP (2) | JP2015500833A (enExample) |
| CA (1) | CA2855994A1 (enExample) |
| WO (1) | WO2013085922A1 (enExample) |
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| US9394294B2 (en) | 2010-05-11 | 2016-07-19 | Demerx, Inc. | Methods and compositions for preparing and purifying noribogaine |
| US8802832B2 (en) | 2010-06-22 | 2014-08-12 | Demerx, Inc. | Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier |
| US9586954B2 (en) | 2010-06-22 | 2017-03-07 | Demerx, Inc. | N-substituted noribogaine prodrugs |
| EP2595632A1 (en) | 2010-07-23 | 2013-05-29 | DemeRx, Inc. | Noribogaine compositions |
| EP2481740B1 (en) | 2011-01-26 | 2015-11-04 | DemeRx, Inc. | Methods and compositions for preparing noribogaine from voacangine |
| US9617274B1 (en) | 2011-08-26 | 2017-04-11 | Demerx, Inc. | Synthetic noribogaine |
| JP2015500833A (ja) * | 2011-12-09 | 2015-01-08 | デメレックス， インコーポレイテッド | ノルイボガインのリン酸エステル |
| CA2858820C (en) | 2012-01-25 | 2021-08-17 | Demerx, Inc. | Synthetic voacangine |
| JP2016508979A (ja) | 2012-12-20 | 2016-03-24 | デメレックス， インコーポレイテッド | 置換ノルイボガイン |
| US9045481B2 (en) | 2012-12-20 | 2015-06-02 | Demerx, Inc. | Substituted noribogaine |
| US8940728B2 (en) | 2012-12-20 | 2015-01-27 | Demerx, Inc. | Substituted noribogaine |
| WO2014143201A1 (en) * | 2013-03-15 | 2014-09-18 | Demerx, Inc. | Method for noribogaine treatment of addiction in patients on methadone |
| 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 |
| CA2983727A1 (en) * | 2014-04-21 | 2015-10-29 | Demerx, Inc. | N-substituted noribogaine prodrugs |
| US9549935B2 (en) | 2014-07-14 | 2017-01-24 | Demerx, Inc. | Methods and compositions for treating migraines using noribogaine |
| ES2955490T3 (es) | 2014-11-26 | 2023-12-01 | Demerx Inc | Métodos y composiciones para potenciar la acción de los analgésicos opioides mediante el uso de alcaloides de la iboga |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| 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 |
| CN120555529A (zh) | 2018-03-08 | 2025-08-29 | 指南针探路者有限公司 | 生产色胺的方法 |
| WO2020212951A1 (en) | 2019-04-17 | 2020-10-22 | Compass Pathfinder Limited | Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| EP3747992A1 (en) | 2019-06-04 | 2020-12-09 | Medizinische Hochschule Hannover | Compositions and process for integrating cells into epithelium |
| WO2024145462A1 (en) * | 2022-12-29 | 2024-07-04 | Atai Therapeutics, Inc. | Ibogaine and noribogaine analogs and methods of use |
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| US8741891B1 (en) * | 2010-06-22 | 2014-06-03 | Demerx, Inc. | N-substituted noribogaine prodrugs |
| US8637648B1 (en) | 2010-06-22 | 2014-01-28 | Demerx, Inc. | Compositions comprising noribogaine and an excipient to facilitate transport across the blood brain barrier |
| EP2595632A1 (en) | 2010-07-23 | 2013-05-29 | DemeRx, Inc. | Noribogaine compositions |
| EP2481740B1 (en) | 2011-01-26 | 2015-11-04 | DemeRx, Inc. | Methods and compositions for preparing noribogaine from voacangine |
| BR112014005064A2 (pt) | 2011-09-15 | 2017-04-04 | Demerx Inc | não solvatos de sal de norigobaína |
| JP2015500833A (ja) * | 2011-12-09 | 2015-01-08 | デメレックス， インコーポレイテッド | ノルイボガインのリン酸エステル |
| US9045481B2 (en) | 2012-12-20 | 2015-06-02 | Demerx, Inc. | Substituted noribogaine |
| JP2016508979A (ja) * | 2012-12-20 | 2016-03-24 | デメレックス， インコーポレイテッド | 置換ノルイボガイン |
| US8940728B2 (en) | 2012-12-20 | 2015-01-27 | Demerx, Inc. | Substituted noribogaine |
| US20150258104A1 (en) * | 2014-03-13 | 2015-09-17 | Demerx, Inc. | Use of noribogaine for the treatment of pain |
-
2012
- 2012-12-04 JP JP2014545985A patent/JP2015500833A/ja active Pending
- 2012-12-04 WO PCT/US2012/067799 patent/WO2013085922A1/en not_active Ceased
- 2012-12-04 CA CA2855994A patent/CA2855994A1/en not_active Abandoned
- 2012-12-04 EP EP12854847.6A patent/EP2788003A4/en not_active Withdrawn
- 2012-12-07 US US13/708,837 patent/US9051343B2/en active Active
-
2015
- 2015-05-29 US US14/726,399 patent/US20160115185A1/en not_active Abandoned
-
2017
- 2017-08-24 JP JP2017161035A patent/JP2017203047A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2017203047A (ja) | 2017-11-16 |
| JP2015500833A (ja) | 2015-01-08 |
| US20130165414A1 (en) | 2013-06-27 |
| WO2013085922A1 (en) | 2013-06-13 |
| EP2788003A4 (en) | 2015-05-27 |
| US20160115185A1 (en) | 2016-04-28 |
| US9051343B2 (en) | 2015-06-09 |
| EP2788003A1 (en) | 2014-10-15 |
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