ZA200006915B - Febrifugine and isofebrifugine and processes for the preparation of both. - Google Patents
Febrifugine and isofebrifugine and processes for the preparation of both. Download PDFInfo
- Publication number
- ZA200006915B ZA200006915B ZA200006915A ZA200006915A ZA200006915B ZA 200006915 B ZA200006915 B ZA 200006915B ZA 200006915 A ZA200006915 A ZA 200006915A ZA 200006915 A ZA200006915 A ZA 200006915A ZA 200006915 B ZA200006915 B ZA 200006915B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- febrifugine
- isofebrifugine
- represented
- Prior art date
Links
- YLYLCQRQSRDSQR-NNKZFNQJSA-N 3-[[(3as,7ar)-2-hydroxy-3a,4,5,6,7,7a-hexahydro-3h-furo[3,2-b]pyridin-2-yl]methyl]quinazolin-4-one Chemical compound N([C@H]1C2)CCC[C@H]1OC2(O)CN1C(=O)C2=CC=CC=C2N=C1 YLYLCQRQSRDSQR-NNKZFNQJSA-N 0.000 title claims description 25
- FWVHWDSCPKXMDB-LSDHHAIUSA-N Febrifugine Chemical compound O[C@@H]1CCCN[C@H]1CC(=O)CN1C(=O)C2=CC=CC=C2N=C1 FWVHWDSCPKXMDB-LSDHHAIUSA-N 0.000 title claims description 25
- YLYLCQRQSRDSQR-UHFFFAOYSA-N (+)-Isofebrifugin Natural products C1C2NCCCC2OC1(O)CN1C(=O)C2=CC=CC=C2N=C1 YLYLCQRQSRDSQR-UHFFFAOYSA-N 0.000 title claims description 24
- UIHLDYLKWIWXAH-UHFFFAOYSA-N Febrifugine Natural products OC1CCNCC1CC(=O)CN2C=Nc3ccccc3C2=O UIHLDYLKWIWXAH-UHFFFAOYSA-N 0.000 title claims description 24
- YLYLCQRQSRDSQR-LZWOXQAQSA-N Isofebrifugine Natural products O=C1N(C[C@@]2(O)O[C@H]3[C@@H](NCCC3)C2)C=Nc2c1cccc2 YLYLCQRQSRDSQR-LZWOXQAQSA-N 0.000 title claims description 24
- FWVHWDSCPKXMDB-UHFFFAOYSA-N febrifugine dihydrochloride Natural products OC1CCCNC1CC(=O)CN1C(=O)C2=CC=CC=C2N=C1 FWVHWDSCPKXMDB-UHFFFAOYSA-N 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 piperidine compound Chemical class 0.000 claims description 16
- 150000002430 hydrocarbons Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 10
- 238000006683 Mannich reaction Methods 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 4
- 150000002910 rare earth metals Chemical class 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 3
- PISXFRKMFSRNDM-UHFFFAOYSA-N 2-silyloxypropanal Chemical compound [SiH3]OC(C=O)C PISXFRKMFSRNDM-UHFFFAOYSA-N 0.000 claims description 2
- 238000007259 addition reaction Methods 0.000 claims description 2
- 238000005882 aldol condensation reaction Methods 0.000 claims description 2
- 230000000078 anti-malarial effect Effects 0.000 claims description 2
- 239000003430 antimalarial agent Substances 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000011968 lewis acid catalyst Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 201000004792 malaria Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 241001092080 Hydrangea Species 0.000 description 1
- 235000014486 Hydrangea macrophylla Nutrition 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000006668 aldol addition reaction Methods 0.000 description 1
- 238000005575 aldol reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940126678 chinese medicines Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP05263199A JP3459189B2 (ja) | 1999-03-01 | 1999-03-01 | フェブリフジンおよびイソフェブリフジンとその製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200006915B true ZA200006915B (en) | 2001-12-05 |
Family
ID=12920182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200006915A ZA200006915B (en) | 1999-03-01 | 2000-11-24 | Febrifugine and isofebrifugine and processes for the preparation of both. |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6420372B1 (zh) |
| EP (1) | EP1076057B1 (zh) |
| JP (1) | JP3459189B2 (zh) |
| KR (1) | KR100416182B1 (zh) |
| CN (1) | CN1197859C (zh) |
| AU (1) | AU769510B2 (zh) |
| CA (1) | CA2330798C (zh) |
| DE (1) | DE60029697T2 (zh) |
| TW (1) | TWI267512B (zh) |
| WO (1) | WO2000052005A1 (zh) |
| ZA (1) | ZA200006915B (zh) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040053950A1 (en) * | 2002-06-20 | 2004-03-18 | Suping Jiang | Antimalarial activities and therapeutic properties of febrifugine analogues |
| FR2842423B1 (fr) * | 2002-07-18 | 2005-07-08 | Centre Nat Rech Scient | Composes a activite anti-parasitaire et medicaments les renfermant |
| US8188303B2 (en) | 2005-10-04 | 2012-05-29 | The Director General, Defence Research And Development Organisation | Anti-malarial compound isolated from Gomphostema niveum |
| JP4829152B2 (ja) * | 2007-03-08 | 2011-12-07 | 独立行政法人科学技術振興機構 | フェブリフジン及びイソフェブリフジンの新規製造方法 |
| WO2009023267A2 (en) * | 2007-08-15 | 2009-02-19 | President And Fellows Of Harvard College | Methods for modulating development and expansion of il-17 expressing cells |
| CN101648942B (zh) * | 2009-09-21 | 2011-04-06 | 王孝麒 | 一种常山酮衍生物的制备方法 |
| CN102603615B (zh) * | 2012-02-22 | 2013-11-13 | 中国海洋大学 | 2-丙酮基-3-甲氧基哌啶的中间体及其制备方法 |
| DE112013007543B4 (de) | 2013-10-30 | 2024-10-17 | Latvian Institute Of Organic Synthesis | Neu substituierte 2-Aminoquinazolin-4(3H)-one Derivate als Malaria Aspartat protease Inhibitoren |
| CN103980251B (zh) * | 2014-04-24 | 2017-01-18 | 广东工业大学 | 常山碱衍生物及其在制备抗耐药菌药物中的应用 |
| CN104472872A (zh) * | 2014-11-15 | 2015-04-01 | 中国农业科学院兰州畜牧与兽药研究所 | 常山碱的新用途 |
| WO2019109055A1 (en) * | 2017-12-02 | 2019-06-06 | Allied-Bristol Life Sciences, Llc | Febrifugine derivatives |
| CN112662382A (zh) * | 2019-10-16 | 2021-04-16 | 中国石油化工股份有限公司 | 一种数据中心导热工质 |
| CN111100079B (zh) * | 2019-12-30 | 2021-03-19 | 重庆市畜牧科学院 | 一类常山碱衍生物及其制备方法和应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4762838A (en) * | 1985-08-30 | 1988-08-09 | Pfizer Inc. | Quinazolin-4(3H)-one derivatives as anticoccidial agents |
-
1999
- 1999-03-01 JP JP05263199A patent/JP3459189B2/ja not_active Expired - Fee Related
-
2000
- 2000-03-01 DE DE60029697T patent/DE60029697T2/de not_active Expired - Fee Related
- 2000-03-01 KR KR10-2000-7012061A patent/KR100416182B1/ko not_active IP Right Cessation
- 2000-03-01 TW TW089103539A patent/TWI267512B/zh not_active IP Right Cessation
- 2000-03-01 CA CA002330798A patent/CA2330798C/en not_active Expired - Fee Related
- 2000-03-01 EP EP00906594A patent/EP1076057B1/en not_active Expired - Lifetime
- 2000-03-01 AU AU28245/00A patent/AU769510B2/en not_active Ceased
- 2000-03-01 WO PCT/JP2000/001192 patent/WO2000052005A1/ja active IP Right Grant
- 2000-03-01 US US09/674,362 patent/US6420372B1/en not_active Expired - Lifetime
- 2000-03-01 CN CNB008002525A patent/CN1197859C/zh not_active Expired - Fee Related
- 2000-11-24 ZA ZA200006915A patent/ZA200006915B/en unknown
-
2002
- 2002-07-03 US US10/187,895 patent/US6844350B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1076057A4 (en) | 2003-02-12 |
| US6420372B1 (en) | 2002-07-16 |
| TWI267512B (en) | 2006-12-01 |
| CA2330798A1 (en) | 2000-09-08 |
| US20020193387A1 (en) | 2002-12-19 |
| KR100416182B1 (ko) | 2004-01-24 |
| AU2824500A (en) | 2000-09-21 |
| WO2000052005A1 (fr) | 2000-09-08 |
| EP1076057A1 (en) | 2001-02-14 |
| JP2000247971A (ja) | 2000-09-12 |
| CN1296483A (zh) | 2001-05-23 |
| EP1076057B1 (en) | 2006-08-02 |
| AU769510B2 (en) | 2004-01-29 |
| JP3459189B2 (ja) | 2003-10-20 |
| DE60029697D1 (de) | 2006-09-14 |
| CA2330798C (en) | 2008-06-17 |
| KR20010024981A (ko) | 2001-03-26 |
| US6844350B2 (en) | 2005-01-18 |
| CN1197859C (zh) | 2005-04-20 |
| DE60029697T2 (de) | 2007-08-09 |
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