PL120977B1 - Process for preparing novel 1,4-benzodioxane derivative - Google Patents
Process for preparing novel 1,4-benzodioxane derivative Download PDFInfo
- Publication number
- PL120977B1 PL120977B1 PL1979218339A PL21833979A PL120977B1 PL 120977 B1 PL120977 B1 PL 120977B1 PL 1979218339 A PL1979218339 A PL 1979218339A PL 21833979 A PL21833979 A PL 21833979A PL 120977 B1 PL120977 B1 PL 120977B1
- Authority
- PL
- Poland
- Prior art keywords
- acetone
- temperature
- weight
- concentrated
- reduced pressure
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 46
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 241000196324 Embryophyta Species 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000284 extract Substances 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 240000007643 Phytolacca americana Species 0.000 claims description 4
- 235000009074 Phytolacca americana Nutrition 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- 235000011869 dried fruits Nutrition 0.000 claims description 4
- 150000004676 glycans Chemical class 0.000 claims description 4
- 229920002521 macromolecule Polymers 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 229920002307 Dextran Polymers 0.000 claims description 3
- OHQVJZXZOCBRIJ-UHFFFAOYSA-N Americanin Chemical compound C1=C(OC)C(OC)=CC=C1CC1C(CC=2C=C(OC)C(OC3C(C(OC(=O)C=CC=4C=C(O)C(O)=CC=4)C(O)C(CO)O3)O)=CC=2)C(=O)OC1 OHQVJZXZOCBRIJ-UHFFFAOYSA-N 0.000 description 14
- SDDXIQONGFZHJH-UHFFFAOYSA-N Isoamericanin A Natural products OCC1OC2=CC=C(C=CC=O)C=C2OC1C1=CC=C(O)C(O)=C1 SDDXIQONGFZHJH-UHFFFAOYSA-N 0.000 description 7
- 108010003672 americanin Proteins 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KPKZJLCSROULON-QKGLWVMZSA-N Phalloidin Chemical compound N1C(=O)[C@@H]([C@@H](O)C)NC(=O)[C@H](C)NC(=O)[C@H](C[C@@](C)(O)CO)NC(=O)[C@H](C2)NC(=O)[C@H](C)NC(=O)[C@@H]3C[C@H](O)CN3C(=O)[C@@H]1CSC1=C2C2=CC=CC=C2N1 KPKZJLCSROULON-QKGLWVMZSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 108010009711 Phalloidine Proteins 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 210000005229 liver cell Anatomy 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000219506 Phytolacca Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 208000019423 liver disease Diseases 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- CHZDTZAJKIIRMS-UHFFFAOYSA-N (2,4-dinitrophenyl)hydrazine;sulfuric acid Chemical compound OS(O)(=O)=O.NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CHZDTZAJKIIRMS-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000002337 glycosamines Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- -1 tetradorofuran Chemical compound 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Gastroenterology & Hepatology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782840467 DE2840467A1 (de) | 1978-09-16 | 1978-09-16 | 3,4-dihydroxizimtaldehydderivat, dessen herstellung und arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL218339A1 PL218339A1 (sv) | 1980-12-01 |
| PL120977B1 true PL120977B1 (en) | 1982-04-30 |
Family
ID=6049691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1979218339A PL120977B1 (en) | 1978-09-16 | 1979-09-15 | Process for preparing novel 1,4-benzodioxane derivative |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5559182A (sv) |
| AR (3) | AR221900A1 (sv) |
| AT (1) | AT367417B (sv) |
| BE (1) | BE878824A (sv) |
| CA (1) | CA1128532A (sv) |
| CS (3) | CS221523B2 (sv) |
| DE (1) | DE2840467A1 (sv) |
| ES (3) | ES8101578A1 (sv) |
| FR (1) | FR2436145A1 (sv) |
| GB (1) | GB2035300B (sv) |
| IT (1) | IT7925651A0 (sv) |
| LU (1) | LU81679A1 (sv) |
| NL (1) | NL7906881A (sv) |
| PL (1) | PL120977B1 (sv) |
| PT (1) | PT70177A (sv) |
| SE (1) | SE7907656L (sv) |
| SU (1) | SU925246A3 (sv) |
| ZA (1) | ZA794815B (sv) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2851919A1 (fr) * | 2003-03-03 | 2004-09-10 | Lmd | Lignanes utilisables comme inhibiteurs de cathepsines et leurs applications |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2428680C2 (de) * | 1974-06-14 | 1983-02-17 | Dr. Madaus & Co, 5000 Köln | 1-(2',4',6'-Trihydroxyphenyl)-propandion-(1,2)-Verbindungen, Verfahren zu deren Herstellung und Arzneimittel, die diese Verbindungen enthalten |
-
1978
- 1978-09-16 DE DE19782840467 patent/DE2840467A1/de not_active Withdrawn
-
1979
- 1979-09-11 ZA ZA00794815A patent/ZA794815B/xx unknown
- 1979-09-12 LU LU81679A patent/LU81679A1/de unknown
- 1979-09-12 IT IT7925651A patent/IT7925651A0/it unknown
- 1979-09-14 NL NL7906881A patent/NL7906881A/nl not_active Application Discontinuation
- 1979-09-14 PT PT70177A patent/PT70177A/pt unknown
- 1979-09-14 CA CA335,661A patent/CA1128532A/en not_active Expired
- 1979-09-14 CS CS814301A patent/CS221523B2/cs unknown
- 1979-09-14 CS CS796224A patent/CS221521B2/cs unknown
- 1979-09-14 AT AT0607979A patent/AT367417B/de not_active IP Right Cessation
- 1979-09-14 CS CS814300A patent/CS221522B2/cs unknown
- 1979-09-14 FR FR7923013A patent/FR2436145A1/fr active Pending
- 1979-09-14 SU SU792811705A patent/SU925246A3/ru active
- 1979-09-14 SE SE7907656A patent/SE7907656L/sv not_active Application Discontinuation
- 1979-09-15 PL PL1979218339A patent/PL120977B1/pl unknown
- 1979-09-15 ES ES484202A patent/ES8101578A1/es not_active Expired
- 1979-09-17 GB GB7932131A patent/GB2035300B/en not_active Expired
- 1979-09-17 AR AR278071A patent/AR221900A1/es active
- 1979-09-17 JP JP11800679A patent/JPS5559182A/ja active Pending
- 1979-09-17 BE BE0/197176A patent/BE878824A/fr unknown
-
1980
- 1980-01-31 ES ES488141A patent/ES488141A0/es active Granted
- 1980-01-31 ES ES488140A patent/ES8101579A1/es not_active Expired
-
1981
- 1981-02-25 AR AR284433A patent/AR226094A1/es active
- 1981-02-25 AR AR284432A patent/AR225070A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| CS221523B2 (en) | 1983-04-29 |
| AT367417B (de) | 1982-07-12 |
| ES484202A0 (es) | 1980-12-16 |
| CS221522B2 (en) | 1983-04-29 |
| LU81679A1 (de) | 1980-01-24 |
| DE2840467A1 (de) | 1980-03-20 |
| SE7907656L (sv) | 1980-03-17 |
| BE878824A (fr) | 1980-03-17 |
| PL218339A1 (sv) | 1980-12-01 |
| ES8101578A1 (es) | 1980-12-16 |
| GB2035300A (en) | 1980-06-18 |
| AR221900A1 (es) | 1981-03-31 |
| ES8101580A1 (es) | 1980-12-16 |
| JPS5559182A (en) | 1980-05-02 |
| ES488140A0 (es) | 1980-12-16 |
| NL7906881A (nl) | 1980-03-18 |
| ZA794815B (en) | 1980-10-29 |
| GB2035300B (en) | 1983-03-23 |
| ES8101579A1 (es) | 1980-12-16 |
| ES488141A0 (es) | 1980-12-16 |
| PT70177A (de) | 1979-10-01 |
| AR225070A1 (es) | 1982-02-15 |
| IT7925651A0 (it) | 1979-09-12 |
| AR226094A1 (es) | 1982-05-31 |
| SU925246A3 (ru) | 1982-04-30 |
| CA1128532A (en) | 1982-07-27 |
| CS221521B2 (en) | 1983-04-29 |
| FR2436145A1 (fr) | 1980-04-11 |
| ATA607979A (de) | 1981-11-15 |
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