NO130345B - - Google Patents
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- Publication number
- NO130345B NO130345B NO01710/70A NO171070A NO130345B NO 130345 B NO130345 B NO 130345B NO 01710/70 A NO01710/70 A NO 01710/70A NO 171070 A NO171070 A NO 171070A NO 130345 B NO130345 B NO 130345B
- Authority
- NO
- Norway
- Prior art keywords
- alkyne
- ether
- phenyl
- distilled
- solution
- Prior art date
Links
- 150000001345 alkine derivatives Chemical class 0.000 claims description 7
- 150000002736 metal compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 230000011514 reflex Effects 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229960004815 meprobamate Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SFDZETWZUCDYMD-UHFFFAOYSA-N monosodium acetylide Chemical compound [Na+].[C-]#C SFDZETWZUCDYMD-UHFFFAOYSA-N 0.000 description 2
- HTYIXCKSEQQCJO-UHFFFAOYSA-N phenaglycodol Chemical compound CC(C)(O)C(C)(O)C1=CC=C(Cl)C=C1 HTYIXCKSEQQCJO-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- UITOSQGEGYAGQL-UHFFFAOYSA-N 1,5-dimethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound CCCC(C)C1(C)C(=O)NC(=O)N(C)C1=O UITOSQGEGYAGQL-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 208000004209 confusion Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 229950005116 phenaglycodol Drugs 0.000 description 1
- 230000001144 postural effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
-
- 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)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mycology (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Alternative & Traditional Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compounds Of Unknown Constitution (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1923082A DE1923082C3 (de) | 1969-05-06 | 1969-05-06 | Verfahren zur Gewinnung von Polyhydroxyphenylchromanonen (Silymarin I-IV) und Arzneimittel enthaltend das Polyhydroxyphenylchromanon (Silymarin I-IV = Silymarin I-IV-Gruppe)Gemisch |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130345B true NO130345B (es) | 1974-08-19 |
Family
ID=5733385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01710/70A NO130345B (es) | 1969-05-06 | 1970-05-05 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT290723B (es) |
| CH (1) | CH541554A (es) |
| CS (1) | CS162722B2 (es) |
| DE (1) | DE1923082C3 (es) |
| ES (1) | ES367906A1 (es) |
| FI (1) | FI50932C (es) |
| IE (1) | IE34110B1 (es) |
| IL (1) | IL34381A (es) |
| NO (1) | NO130345B (es) |
| PL (1) | PL80560B1 (es) |
| YU (1) | YU37065B (es) |
Families Citing this family (5)
| 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 |
| DE3537656A1 (de) * | 1984-11-22 | 1986-05-22 | Dr. Madaus GmbH & Co, 5000 Köln | Verfahren zur herstellung von isosilybinfreiem silibinin und arzneimittel, enthaltend silibinin |
| FR2594691B1 (fr) * | 1986-02-24 | 1990-08-03 | Bonne Claude | Nouvelles preparations cosmetiques contenant un extrait des fruits de silybum marianum |
| DE4401902C2 (de) * | 1994-01-24 | 2000-02-03 | Madaus Ag | Verwendung von Flavolignanen als Adjuvans in der Tumortherapie |
| EP2959910A1 (de) | 2014-06-26 | 2015-12-30 | Bionorica Se | Mariendistelextrakt aus Mariendistelfrüchteschalen, Verfahren zur Herstellung und Verwendung |
-
1969
- 1969-05-06 DE DE1923082A patent/DE1923082C3/de not_active Expired
- 1969-05-30 AT AT517269A patent/AT290723B/de not_active IP Right Cessation
- 1969-05-30 CH CH825169A patent/CH541554A/de not_active IP Right Cessation
- 1969-05-31 ES ES367906A patent/ES367906A1/es not_active Expired
-
1970
- 1970-04-21 IE IE510/70A patent/IE34110B1/xx unknown
- 1970-04-24 IL IL34381A patent/IL34381A/en unknown
- 1970-05-04 YU YU1129/70A patent/YU37065B/xx unknown
- 1970-05-05 NO NO01710/70A patent/NO130345B/no unknown
- 1970-05-05 CS CS3099A patent/CS162722B2/cs unknown
- 1970-05-05 FI FI701253A patent/FI50932C/fi active
- 1970-05-05 PL PL1970140431A patent/PL80560B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL34381A0 (en) | 1970-06-17 |
| FI50932C (fi) | 1976-09-10 |
| AT290723B (de) | 1971-06-11 |
| CH541554A (de) | 1973-09-15 |
| DE1923082A1 (de) | 1970-11-19 |
| IL34381A (en) | 1973-06-29 |
| PL80560B1 (es) | 1975-08-30 |
| FI50932B (es) | 1976-05-31 |
| ES367906A1 (es) | 1971-04-16 |
| IE34110B1 (en) | 1975-02-05 |
| DE1923082B2 (de) | 1974-09-19 |
| CS162722B2 (es) | 1975-07-15 |
| YU37065B (en) | 1984-08-31 |
| YU112970A (en) | 1983-04-27 |
| DE1923082C3 (de) | 1985-08-22 |
| IE34110L (en) | 1970-11-06 |
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