NO773531L - Fremgangsmaate for fremstilling av aristolochinsyre fra holurtarer - Google Patents
Fremgangsmaate for fremstilling av aristolochinsyre fra holurtarerInfo
- Publication number
- NO773531L NO773531L NO773531A NO773531A NO773531L NO 773531 L NO773531 L NO 773531L NO 773531 A NO773531 A NO 773531A NO 773531 A NO773531 A NO 773531A NO 773531 L NO773531 L NO 773531L
- Authority
- NO
- Norway
- Prior art keywords
- precipitate
- acid
- extract
- procedure
- stated
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 238000000605 extraction Methods 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 18
- 239000002244 precipitate Substances 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000007513 acids Chemical class 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 17
- BBFQZRXNYIEMAW-UHFFFAOYSA-N aristolochic acid I Chemical compound C1=C([N+]([O-])=O)C2=C(C(O)=O)C=C3OCOC3=C2C2=C1C(OC)=CC=C2 BBFQZRXNYIEMAW-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 241000726094 Aristolochia Species 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 235000010755 mineral Nutrition 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- BBFQZRXNYIEMAW-UHFFFAOYSA-M Aristolochate I Natural products C1=C([N+]([O-])=O)C2=C(C([O-])=O)C=C3OCOC3=C2C2=C1C(OC)=CC=C2 BBFQZRXNYIEMAW-UHFFFAOYSA-M 0.000 description 3
- 241000046585 Aristolochia clematitis Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 241000046617 Aristolochia debilis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 235000003332 Ilex aquifolium Nutrition 0.000 description 2
- 235000002296 Ilex sandwicensis Nutrition 0.000 description 2
- 235000002294 Ilex volkensiana Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- VMRYFYIDRLZSES-UHFFFAOYSA-N 2-nitrophenanthrene-1-carboxylic acid Chemical class C1=CC2=CC=CC=C2C2=C1C(C(=O)O)=C([N+]([O-])=O)C=C2 VMRYFYIDRLZSES-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000046581 Aristolochia argentina Species 0.000 description 1
- 241000093833 Aristolochia contorta Species 0.000 description 1
- 241001263026 Aristolochia griffithii Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000218158 Clematis Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- MEEXETVZNQYRSP-UHFFFAOYSA-N aristolochic acid B Chemical group C12=C3C=CC=CC3=CC([N+]([O-])=O)=C2C(C(=O)O)=CC2=C1OCO2 MEEXETVZNQYRSP-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001656 butanoic acid esters Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/26—Aristolochiaceae (Birthwort family), e.g. heartleaf
- A61K36/264—Aristolochia (Dutchman's pipe)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Botany (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2646545A DE2646545C3 (de) | 1976-10-15 | 1976-10-15 | Verfahren zur Gewinnung von Aristolochiasäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO773531L true NO773531L (no) | 1978-04-18 |
Family
ID=5990511
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO773531A NO773531L (no) | 1976-10-15 | 1977-10-14 | Fremgangsmaate for fremstilling av aristolochinsyre fra holurtarer |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4162255A (pl) |
| JP (1) | JPS5352610A (pl) |
| AR (1) | AR213325A1 (pl) |
| AT (1) | AT358722B (pl) |
| AU (1) | AU519522B2 (pl) |
| BE (1) | BE859766A (pl) |
| DE (1) | DE2646545C3 (pl) |
| FI (1) | FI772662A7 (pl) |
| FR (1) | FR2367760A1 (pl) |
| GB (1) | GB1589671A (pl) |
| GR (1) | GR63656B (pl) |
| LU (1) | LU78315A1 (pl) |
| MX (1) | MX4531E (pl) |
| NL (1) | NL7709874A (pl) |
| NO (1) | NO773531L (pl) |
| PH (1) | PH15815A (pl) |
| PL (1) | PL107584B1 (pl) |
| PT (1) | PT67043B (pl) |
| SE (1) | SE7711349L (pl) |
| SU (1) | SU670222A3 (pl) |
| ZA (1) | ZA775843B (pl) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19704484A1 (de) * | 1997-02-06 | 1998-09-03 | Dragoco Gerberding Co Ag | Cyclische Cedren-Acetale, ihre Herstellung und ihre Verwendung |
| JP2002112767A (ja) * | 2000-10-03 | 2002-04-16 | Sangaku Renkei Kiko Kyushu:Kk | 抗アリストロキア酸モノクローナル抗体 |
| CN1847841B (zh) * | 2005-04-12 | 2010-04-28 | 天津天士力制药股份有限公司 | 中药水提取液中微量马兜铃酸a的含量测定方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE450914A (pl) * | 1942-06-02 | |||
| DE1186980B (de) * | 1963-06-22 | 1965-02-11 | Hoechst Ag | Verfahren zur Gewinnung von Aristolochiasaeure |
| FR3670M (fr) * | 1964-03-25 | 1965-11-08 | Madaus & Co Dr | Nouveau médicament applicable par voie orale pour le traitement d'ulcérations chroniques des tissus. |
-
1976
- 1976-10-15 DE DE2646545A patent/DE2646545C3/de not_active Expired
-
1977
- 1977-08-26 AT AT619377A patent/AT358722B/de not_active IP Right Cessation
- 1977-08-31 AR AR269040A patent/AR213325A1/es active
- 1977-09-01 AU AU28482/77A patent/AU519522B2/en not_active Expired
- 1977-09-08 FI FI772662A patent/FI772662A7/fi not_active Application Discontinuation
- 1977-09-08 NL NL7709874A patent/NL7709874A/xx not_active Application Discontinuation
- 1977-09-16 PT PT67043A patent/PT67043B/pt unknown
- 1977-09-30 ZA ZA00775843A patent/ZA775843B/xx unknown
- 1977-10-04 PH PH20295A patent/PH15815A/en unknown
- 1977-10-10 SE SE7711349A patent/SE7711349L/xx not_active Application Discontinuation
- 1977-10-11 GR GR54550A patent/GR63656B/el unknown
- 1977-10-11 GB GB42284/77A patent/GB1589671A/en not_active Expired
- 1977-10-13 LU LU78315A patent/LU78315A1/xx unknown
- 1977-10-14 PL PL1977201522A patent/PL107584B1/pl unknown
- 1977-10-14 FR FR7730995A patent/FR2367760A1/fr active Granted
- 1977-10-14 BE BE181779A patent/BE859766A/xx unknown
- 1977-10-14 SU SU772534500A patent/SU670222A3/ru active
- 1977-10-14 MX MX776485U patent/MX4531E/es unknown
- 1977-10-14 NO NO773531A patent/NO773531L/no unknown
- 1977-10-15 JP JP12399577A patent/JPS5352610A/ja active Pending
- 1977-10-17 US US05/843,004 patent/US4162255A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AT358722B (de) | 1980-09-25 |
| PL201522A1 (pl) | 1978-09-25 |
| PT67043B (en) | 1979-02-16 |
| FI772662A7 (fi) | 1978-04-16 |
| ZA775843B (en) | 1978-09-27 |
| GR63656B (en) | 1979-11-28 |
| DE2646545A1 (de) | 1978-04-20 |
| AU519522B2 (en) | 1981-12-10 |
| SU670222A3 (ru) | 1979-06-25 |
| AU2848277A (en) | 1979-03-08 |
| ATA619377A (de) | 1980-02-15 |
| PL107584B1 (pl) | 1980-02-29 |
| NL7709874A (nl) | 1978-04-18 |
| LU78315A1 (pl) | 1978-01-24 |
| DE2646545B2 (de) | 1979-07-26 |
| GB1589671A (en) | 1981-05-20 |
| DE2646545C3 (de) | 1980-03-20 |
| BE859766A (fr) | 1978-04-14 |
| SE7711349L (sv) | 1978-04-16 |
| PT67043A (en) | 1977-10-01 |
| US4162255A (en) | 1979-07-24 |
| FR2367760B1 (pl) | 1982-06-18 |
| PH15815A (en) | 1983-03-28 |
| FR2367760A1 (fr) | 1978-05-12 |
| MX4531E (es) | 1982-06-03 |
| AR213325A1 (es) | 1979-01-15 |
| JPS5352610A (en) | 1978-05-13 |
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