OA11491A - Voacamine as anti-malarial agent and anti-malarialagent containing voacamine. - Google Patents
Voacamine as anti-malarial agent and anti-malarialagent containing voacamine. Download PDFInfo
- Publication number
- OA11491A OA11491A OA1200000261A OA1200000261A OA11491A OA 11491 A OA11491 A OA 11491A OA 1200000261 A OA1200000261 A OA 1200000261A OA 1200000261 A OA1200000261 A OA 1200000261A OA 11491 A OA11491 A OA 11491A
- Authority
- OA
- OAPI
- Prior art keywords
- voacamine
- extract
- strains
- malarial
- agent according
- Prior art date
Links
- KQFGPIYUBNBTND-UHFFFAOYSA-N voacamine Natural products CCC1CC2CN3CCc4c([nH]c5c(cc(OC)cc45)C6CC7C(C(Cc8c6[nH]c9ccccc89)N(C)C/C/7=CC)C(=O)OC)C(C2)(C13)C(=O)OC KQFGPIYUBNBTND-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 229950009271 voacamine Drugs 0.000 title claims abstract description 31
- VCMIRXRRQJNZJT-KANKAIPDSA-N methyl (1S,15R,17S,18S)-17-ethyl-6-[(1S,12R,14R,15Z,18S)-15-ethylidene-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate Chemical compound CC[C@H]1C[C@H]2CN3CCC4=C(NC5=C4C=C(OC)C(=C5)[C@H]4C[C@@H]5[C@@H]([C@H](CC6=C4NC4=C6C=CC=C4)N(C)C\C5=C/C)C(=O)OC)[C@](C2)([C@H]13)C(=O)OC VCMIRXRRQJNZJT-KANKAIPDSA-N 0.000 title claims abstract description 29
- 239000003430 antimalarial agent Substances 0.000 title claims abstract description 21
- 239000000284 extract Substances 0.000 claims abstract description 26
- 241000223960 Plasmodium falciparum Species 0.000 claims abstract description 5
- 229930013930 alkaloid Natural products 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 11
- 241000224016 Plasmodium Species 0.000 claims description 9
- OYMQKBZMKFJPMH-VJMPXSKLSA-N voacristine Chemical compound N1([C@H]2[C@@H]([C@H](C)O)C[C@@H](C1)C[C@]21C(=O)OC)CCC2=C1NC1=CC=C(OC)C=C21 OYMQKBZMKFJPMH-VJMPXSKLSA-N 0.000 claims description 9
- NVVDQMVGALBDGE-PZXGUROGSA-N (-)-coronaridine Chemical compound C([C@@H]1C[C@@H]([C@H]2[C@]3(C1)C(=O)OC)CC)N2CCC1=C3NC2=CC=CC=C12 NVVDQMVGALBDGE-PZXGUROGSA-N 0.000 claims description 8
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000002955 isolation Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- OYMQKBZMKFJPMH-UHFFFAOYSA-N Voacangarin Natural products COC(=O)C12CC(C3)CC(C(C)O)C1N3CCC1=C2NC2=CC=C(OC)C=C12 OYMQKBZMKFJPMH-UHFFFAOYSA-N 0.000 claims description 5
- LBBNRFISSBZUDC-UHFFFAOYSA-N Conopharyngine Natural products CC(N)C1CCC2C3CC=C4CC(CCC4(C)C3CCC12C)OC5OC(CO)C(O)C(O)C5O LBBNRFISSBZUDC-UHFFFAOYSA-N 0.000 claims description 4
- NVVDQMVGALBDGE-UHFFFAOYSA-N Dihydrocatharanthin Natural products C1C2(C(=O)OC)C3C(CC)CC1CN3CCC1=C2NC2=CC=CC=C12 NVVDQMVGALBDGE-UHFFFAOYSA-N 0.000 claims description 4
- TYPMTMPLTVSOBU-UHFFFAOYSA-N Epi-Vobasin Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2C(=O)OC TYPMTMPLTVSOBU-UHFFFAOYSA-N 0.000 claims description 4
- GKWYINOZGDHWRA-UHFFFAOYSA-N catharanthine Natural products C1C(CC)(O)CC(CC2C(=O)OC)CN1CCC1=C2NC2=CC=CC=C12 GKWYINOZGDHWRA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- TYPMTMPLTVSOBU-XJHWFDBESA-N vobasine Chemical compound C1C(C2=CC=CC=C2N2)=C2C(=O)C[C@H]2\C(=C/C)CN(C)[C@@H]1[C@H]2C(=O)OC TYPMTMPLTVSOBU-XJHWFDBESA-N 0.000 claims description 4
- AYJGPXFEPLVVNT-UHFFFAOYSA-N vobasine Natural products COC(=O)C1C2CC3C4CCCCC4NC3C(=O)CC1C(=CC)CN2C AYJGPXFEPLVVNT-UHFFFAOYSA-N 0.000 claims description 4
- IWEYXWIPVZEVPT-HRJZALPKSA-N Voachalotine Natural products O=C(OC)[C@]1(CO)[C@@H]2/C(=C/C)/CN3[C@H]1Cc1c4c(n(C)c1[C@@H]3C2)cccc4 IWEYXWIPVZEVPT-HRJZALPKSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- DUFLXLVGASPEMV-BPYGGHBPSA-N conopharyngine Chemical compound C([C@H]1C[C@@H]([C@H]2[C@]3(C1)C(=O)OC)CC)N2CCC1=C3NC2=CC(OC)=C(OC)C=C12 DUFLXLVGASPEMV-BPYGGHBPSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000012074 organic phase Substances 0.000 claims description 3
- 239000000419 plant extract Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- -1 voacangerine Chemical compound 0.000 claims description 3
- IWEYXWIPVZEVPT-VQVRLUHXSA-N voachalotine Chemical compound CN1C2=CC=CC=C2C(C[C@H]2[C@]3(CO)C(=O)OC)=C1[C@H]1N2CC(=C/C)/[C@@H]3C1 IWEYXWIPVZEVPT-VQVRLUHXSA-N 0.000 claims description 3
- IWEYXWIPVZEVPT-UHFFFAOYSA-N vonchalotine Natural products CN1C2=CC=CC=C2C(CC2C3(CO)C(=O)OC)=C1C1N2CC(=CC)C3C1 IWEYXWIPVZEVPT-UHFFFAOYSA-N 0.000 claims description 3
- XVSWNFDALFLWFM-VAPIAZESSA-N N-Demethylvoacamin Natural products CCC1CC2CN3CCc4c([nH]c5cc(C6CC7C(C(Cc8c6[nH]c9ccccc89)NC/C/7=C/C)C(=O)OC)c(OC)cc45)C(C2)(C13)C(=O)OC XVSWNFDALFLWFM-VAPIAZESSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000006286 aqueous extract Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- 229960003677 chloroquine Drugs 0.000 description 8
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 8
- 201000004792 malaria Diseases 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 241000255925 Diptera Species 0.000 description 2
- PBQMJIQJGPNOKV-GNEMMXPASA-N Ervahanine A Chemical compound CC[C@H]1C[C@@H]2C[C@@]3([C@H]1N(C2)CCC4=C3NC5=C4C=CC(=C5)[C@H]6C[C@@H]\7[C@@H]([C@H](CC8=C6NC9=CC=CC=C89)N(C/C7=C\C)C)C(=O)OC)C(=O)OC PBQMJIQJGPNOKV-GNEMMXPASA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine 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-WZBLMQSHSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241001246889 Voacanga Species 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- PBQMJIQJGPNOKV-YTONNEOCSA-N ervahanine A Natural products O=C(OC)[C@H]1[C@H]2N(C)C/C(=C\C)/[C@@H]1C[C@H](c1cc3[nH]c4[C@@]5(C(=O)OC)[C@@H]6[C@H](CC)C[C@H](C5)CN6CCc4c3cc1)c1[nH]c3c(c1C2)cccc3 PBQMJIQJGPNOKV-YTONNEOCSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VCMIRXRRQJNZJT-ZONBIMMXSA-N methyl (1S,15R,17S,18S)-17-ethyl-6-[(1S,12S,14R,15E,18S)-15-ethylidene-18-methoxycarbonyl-17-methyl-10,17-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate Chemical compound C([C@H](C1=C(C2=CC=CC=C2N1)C1)C=2C=C3NC4=C(C3=CC=2OC)CCN2C[C@@H]3C[C@@H]([C@H]2[C@]4(C3)C(=O)OC)CC)[C@H]2C(=C\C)/CN(C)[C@@H]1[C@H]2C(=O)OC VCMIRXRRQJNZJT-ZONBIMMXSA-N 0.000 description 2
- NKTORRNHKYVXSU-XXMLWKDOSA-N perivine Chemical compound C1C(C2=CC=CC=C2N2)=C2C(=O)C[C@H]2\C(=C/C)CN[C@@H]1[C@H]2C(=O)OC NKTORRNHKYVXSU-XXMLWKDOSA-N 0.000 description 2
- NKTORRNHKYVXSU-OWQGQXMQSA-N perivine Natural products COC(=O)[C@@H]1[C@@H]2Cc3c([nH]c4ccccc34)C(=O)C[C@H]1C(=CC)CN2 NKTORRNHKYVXSU-OWQGQXMQSA-N 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- MTARGWPMLJBYNG-SESIEVFNSA-N tabernamine Chemical compound C([C@@H](C1=C(C2=CC=CC=C2N1)C1)C=2C=C3NC4=C(C3=CC=2)CCN2[C@@H]3[C@H]4C[C@@H](C2)C[C@@H]3CC)[C@H]2C(=C\C)/CN(C)[C@H]1C2C(=O)OC MTARGWPMLJBYNG-SESIEVFNSA-N 0.000 description 2
- MTARGWPMLJBYNG-UHFFFAOYSA-N tabernamine Natural products CCC1CC(C2)CC3C1N2CCC(C1=CC=2)=C3NC1=CC=2C(C1=C(C2=CC=CC=C2N1)C1)CC2C(=CC)CN(C)C1C2C(=O)OC MTARGWPMLJBYNG-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- CKWXDLJHOHJWOX-UHFFFAOYSA-N voacangine hydroxyindolenine Natural products CCC1CC2N3CCC4(O)C(=Nc5ccc(OC)cc45)C2(CC1C3)C(=O)OC CKWXDLJHOHJWOX-UHFFFAOYSA-N 0.000 description 2
- MMAYTCMMKJYIAM-RUGRQLENSA-N (-)-voacangine Chemical compound C([C@H]1C[C@@H]([C@H]2[C@]3(C1)C(=O)OC)CC)N2CCC1=C3NC2=CC=C(OC)C=C12 MMAYTCMMKJYIAM-RUGRQLENSA-N 0.000 description 1
- PXFBZOLANLWPMH-UHFFFAOYSA-N 16-Epiaffinine Natural products C1C(C2=CC=CC=C2N2)=C2C(=O)CC2C(=CC)CN(C)C1C2CO PXFBZOLANLWPMH-UHFFFAOYSA-N 0.000 description 1
- RCZOPNYUVDGBLR-RDPNLSTCSA-N 16-decarbomethoxyvoacamine Natural products CC[C@H]1C[C@H]2CN3CCc4c([nH]c5cc([C@@H]6C[C@H]7C(=CC)CN(C)[C@@H](Cc8c6[nH]c9ccccc89)[C@@]7(CO)C(=O)OC)c(OC)cc45)[C@](C2)([C@H]13)C(=O)OC RCZOPNYUVDGBLR-RDPNLSTCSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- QHHSFVRCIMKFIZ-UHFFFAOYSA-N Dihydroaffinin Natural products CCC1CN(C)C2Cc3c([nH]c4ccccc34)C(=O)CC1C2CO QHHSFVRCIMKFIZ-UHFFFAOYSA-N 0.000 description 1
- VGDQBNXQAOYMPS-UHFFFAOYSA-N Epiheyneanin Natural products COC(=O)C12CC(C3)CC(C(C)O)C1N3CCC1=C2NC2=CC=CC=C12 VGDQBNXQAOYMPS-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241000223821 Plasmodium malariae Species 0.000 description 1
- 241001505293 Plasmodium ovale Species 0.000 description 1
- 241000223810 Plasmodium vivax Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000511964 Tabernaemontana Species 0.000 description 1
- PSTDKFQDHNZGAL-JAHAZDFLSA-N Voacamidine Natural products CCC1CC2CN3CCc4c([nH]c5ccc(OC)c(C6CC7C(C(Cc8c6[nH]c9ccccc89)N(C)C/C/7=C/C)C(=O)OC)c45)C(C2)(C13)C(=O)OC PSTDKFQDHNZGAL-JAHAZDFLSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- UVWQYWHKTZABSO-FXECBMLZSA-N affinisine Natural products CC=C1CN2[C@H]3Cc4c([C@@H]2C[C@@H]1[C@H]3CO)n(C)c5ccccc45 UVWQYWHKTZABSO-FXECBMLZSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 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 description 1
- 239000002642 cobra venom Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- UVWQYWHKTZABSO-ILADVTTDSA-N de voachalotinol Chemical compound CN1C2=CC=CC=C2C(C[C@H]2[C@@H]3CO)=C1[C@H]1N2C/C(=C/C)[C@@H]3C1 UVWQYWHKTZABSO-ILADVTTDSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940118768 plasmodium malariae Drugs 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compounds Of Unknown Constitution (AREA)
- Extraction Or Liquid Replacement (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98TO000264A ITTO980264A1 (it) | 1998-03-26 | 1998-03-26 | Applicazione di un estratto basico non quaternario della peschiera fuchsiaefolia ad attivita' antimalarica |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11491A true OA11491A (en) | 2004-05-07 |
Family
ID=11416637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200000261A OA11491A (en) | 1998-03-26 | 2000-09-22 | Voacamine as anti-malarial agent and anti-malarialagent containing voacamine. |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP1067938A1 (it) |
| JP (1) | JP2002507570A (it) |
| AP (1) | AP2000001926A0 (it) |
| AU (1) | AU2742799A (it) |
| BR (1) | BR9909153A (it) |
| CA (1) | CA2325879A1 (it) |
| IT (1) | ITTO980264A1 (it) |
| OA (1) | OA11491A (it) |
| WO (1) | WO1999048501A1 (it) |
| ZA (1) | ZA200006020B (it) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2812199A1 (fr) * | 2000-07-31 | 2002-02-01 | Maximun Frederic Yanze | Nouvelles compositions pharmaceutiques effervescentes contenant la chloroquine |
| EP1491197A1 (fr) * | 2003-06-26 | 2004-12-29 | Bertelli Motta, Guiseppe | Composition pharmaceutique à base de voacamine pour la stimulation et modulation du système immunitaire humain |
| US20070232588A1 (en) * | 2004-09-15 | 2007-10-04 | Leonard Stella | Anti-parasitic and/or anti-viral and/or anti-microbial compositions |
| US20070032460A1 (en) * | 2005-08-04 | 2007-02-08 | Leonard Stella | Use of voacamine and related compounds in the treatment of malaria |
| WO2007039915A1 (en) | 2005-10-04 | 2007-04-12 | The Director General, Defence Research And Development Organisation | Anti-malarial compound isolated from gomphostema niveum |
| EP1958638A1 (en) | 2007-02-14 | 2008-08-20 | Polichem S.A. | Use of chitosans to increase nail growth rate |
| US20140303148A1 (en) | 2011-11-28 | 2014-10-09 | Industry-Academic Cooperation Foundation, Yonsei University | Pharmaceutical compositions for inhibiting angiogenesis comprising plant-derived natural compound |
| CA2896133A1 (en) | 2012-12-20 | 2014-06-26 | Demerx, Inc. | Substituted noribogaine |
| 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 |
| US12377112B2 (en) | 2019-04-17 | 2025-08-05 | Compass Pathfinder Limited | Methods of treating neurocognitive disorders, chronic pain and reducing inflammation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2823204A (en) * | 1956-03-30 | 1958-02-11 | Gobey Lab | Alkaloids of voacanga |
-
1998
- 1998-03-26 IT IT98TO000264A patent/ITTO980264A1/it unknown
-
1999
- 1999-03-25 EP EP99907808A patent/EP1067938A1/fr not_active Withdrawn
- 1999-03-25 AU AU27427/99A patent/AU2742799A/en not_active Abandoned
- 1999-03-25 WO PCT/IB1999/000524 patent/WO1999048501A1/fr not_active Ceased
- 1999-03-25 BR BR9909153-4A patent/BR9909153A/pt not_active Application Discontinuation
- 1999-03-25 CA CA002325879A patent/CA2325879A1/fr not_active Abandoned
- 1999-03-25 JP JP2000537549A patent/JP2002507570A/ja active Pending
- 1999-03-25 AP APAP/P/2000/001926A patent/AP2000001926A0/en unknown
-
2000
- 2000-09-22 OA OA1200000261A patent/OA11491A/en unknown
- 2000-10-26 ZA ZA200006020A patent/ZA200006020B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ITTO980264A1 (it) | 1999-09-26 |
| AP2000001926A0 (en) | 2000-09-30 |
| JP2002507570A (ja) | 2002-03-12 |
| CA2325879A1 (fr) | 1999-09-30 |
| WO1999048501A9 (fr) | 2000-03-16 |
| BR9909153A (pt) | 2000-11-14 |
| WO1999048501A1 (fr) | 1999-09-30 |
| EP1067938A1 (fr) | 2001-01-17 |
| AU2742799A (en) | 1999-10-18 |
| ZA200006020B (en) | 2001-06-25 |
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