OA11491A - Voacamine as anti-malarial agent and anti-malarialagent containing voacamine. - Google Patents

Voacamine as anti-malarial agent and anti-malarialagent containing voacamine. Download PDF

Info

Publication number: OA11491A
Authority: OA; OAPI
Prior art keywords: voacamine; extract; strains; malarial; agent according
Prior art date: 1998-03-26

Application number

OA1200000261A

Other languages

English (en)

Inventor

Silvio Rossi

Guiseppe Bertelli Motta

Original Assignee

Millenia Hope Inc

Priority date (The priority date 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 date listed.)

1998-03-26

Filing date

2000-09-22

Publication date

2004-05-07

2000-09-22 Application filed by Millenia Hope Inc filed Critical Millenia Hope Inc

2004-05-07 Publication of OA11491A publication Critical patent/OA11491A/en

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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Extraction Or Liquid Replacement (AREA)
Compounds Of Unknown Constitution (AREA)

OA1200000261A 1998-03-26 2000-09-22 Voacamine as anti-malarial agent and anti-malarialagent containing voacamine. OA11491A (en)

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)

* Cited by examiner, † Cited by third party
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
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
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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
ZA200006020B (en)	2001-06-25
JP2002507570A (ja)	2002-03-12
WO1999048501A9 (fr)	2000-03-16
EP1067938A1 (fr)	2001-01-17
WO1999048501A1 (fr)	1999-09-30
AU2742799A (en)	1999-10-18
ITTO980264A1 (it)	1999-09-26
BR9909153A (pt)	2000-11-14
AP2000001926A0 (en)	2000-09-30
CA2325879A1 (fr)	1999-09-30

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