WO1987004160A1 - N,n'-(bisfurfuryl)-2-furylmethanediamine, its production and use - Google Patents
N,n'-(bisfurfuryl)-2-furylmethanediamine, its production and use Download PDFInfo
- Publication number
- WO1987004160A1 WO1987004160A1 PCT/DE1986/000525 DE8600525W WO8704160A1 WO 1987004160 A1 WO1987004160 A1 WO 1987004160A1 DE 8600525 W DE8600525 W DE 8600525W WO 8704160 A1 WO8704160 A1 WO 8704160A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- bisfurfuryl
- hydrofuramide
- furfurylmethanediamine
- furfural
- acid
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- CYGDSXFTXXFMNI-OTYYAQKOSA-N hydrofuramide Chemical compound C=1C=COC=1/C=N/C(C=1OC=CC=1)\N=C\C1=CC=CO1 CYGDSXFTXXFMNI-OTYYAQKOSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000012071 phase Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 1
- 229910010277 boron hydride Inorganic materials 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 12
- 241000700159 Rattus Species 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010055297 Sterol Esterase Proteins 0.000 description 2
- 102000000019 Sterol Esterase Human genes 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001443715 Fusarium oxysporum f. sp. conglutinans Species 0.000 description 1
- 206010020961 Hypocholesterolaemia Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000000260 hypercholesteremic effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Definitions
- the pH is then adjusted to 10 using 30% sodium hydroxide solution and the anoraganic salts which have precipitated are suctioned off.
- the reaction mixture separates into two phases.
- the tetrahydrofuran phase is separated off and concentrated under a water jet pump vacuum.
- the residue is added to "70 ml Diisopopylether and crystallized.
- the crystals dersrrt obtained are filtered off with suction.
- the Filter ⁇ cake is taken up in 150 ml of acetone and boiled for 30 minutes under reflux.
- the solids are filtered hot with suction and the acetone was completely evaporated.
- the crystalline return The stand is taken up in 80 ml of diisopropyl ether and suction filtered, and the solid is washed with diisopopyl ether and dried at 40 ° C.
- mice Fourteen mice were fed a high cholesterol-cholic acid diet for 7 days.
- the hypercholesterolemic animals were divided into two groups of 7 animals (control group). On the 6th and 7th day after starting the diet, 0.2 mg test substance / animal was administered orally. After fasting at night, a reduction in blood cholesterol levels of over 15% was measured compared to the mice in the control group.
- mice 10 mice were fed with 0.2 g test substance. One hour after the test substance was administered, 5 mice were treated with oxazolone on the shaved abdomen.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853546319 DE3546319A1 (de) | 1985-12-30 | 1985-12-30 | N,n' (bisfurfuryl)-2-furfurylmethandiamin, seine herstellung und seine verwendung |
| DEP3546319.8 | 1985-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1987004160A1 true WO1987004160A1 (en) | 1987-07-16 |
Family
ID=6289678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/DE1986/000525 WO1987004160A1 (en) | 1985-12-30 | 1986-12-30 | N,n'-(bisfurfuryl)-2-furylmethanediamine, its production and use |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0258264A1 (enrdf_load_stackoverflow) |
| JP (1) | JPS63502504A (enrdf_load_stackoverflow) |
| DE (1) | DE3546319A1 (enrdf_load_stackoverflow) |
| WO (1) | WO1987004160A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292903A (en) * | 1991-08-22 | 1994-03-08 | The United States Department Of Agriculture As Represented By The Secretary Of Agriculture | One step method for the preparation of difurfuryl diamines |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1936259A1 (de) * | 1968-07-16 | 1970-02-26 | Proewig Dr Med Frederick W | Pharmazeutische Zubereitung |
| DE2700432A1 (de) * | 1977-01-07 | 1978-07-20 | Brauegg Arzneimittel Kg Bernd | Neuer wirkstoff zur verwendung als arzneimittel mit wertvollen therapeutischen effekten n,n'-difurfuryliden-2- furan-methandiamin |
-
1985
- 1985-12-30 DE DE19853546319 patent/DE3546319A1/de active Granted
-
1986
- 1986-12-30 WO PCT/DE1986/000525 patent/WO1987004160A1/de not_active Application Discontinuation
- 1986-12-30 JP JP62500546A patent/JPS63502504A/ja active Pending
- 1986-12-30 EP EP19870900067 patent/EP0258264A1/de not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1936259A1 (de) * | 1968-07-16 | 1970-02-26 | Proewig Dr Med Frederick W | Pharmazeutische Zubereitung |
| DE2700432A1 (de) * | 1977-01-07 | 1978-07-20 | Brauegg Arzneimittel Kg Bernd | Neuer wirkstoff zur verwendung als arzneimittel mit wertvollen therapeutischen effekten n,n'-difurfuryliden-2- furan-methandiamin |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5292903A (en) * | 1991-08-22 | 1994-03-08 | The United States Department Of Agriculture As Represented By The Secretary Of Agriculture | One step method for the preparation of difurfuryl diamines |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0258264A1 (de) | 1988-03-09 |
| DE3546319A1 (de) | 1987-09-17 |
| JPS63502504A (ja) | 1988-09-22 |
| DE3546319C2 (enrdf_load_stackoverflow) | 1988-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2345064C3 (de) | 4-Amino-2-<l,2r3,4-tetrahydroisochinolin-2 yl)-chinazolinderivate und diese enthaltende Arzneimittel | |
| EP0222191A1 (de) | 4-Benzyl-1-(2H)-phthalazinon-Derivate | |
| EP0028765B1 (de) | Alkylharnstoffderivate zur Behandlung von Erkrankungen des Fettstoffwechsels; Verfahren zu deren Herstellung, deren Verwendung in Arzneimitteln zur Behandlung von Fettstoffwechselstörungen, diese enthaltende Arzneimittel, Verfahren zur Herstellung der Arzneimittel sowie einige Alkylharnstoffverbindungen | |
| DE2234651A1 (de) | Eckige klammer auf 1-(p-chlorbenzoyl)5-methoxy-2-methyl-3-indol eckige klammer zu acetoxyessigsaeure, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln | |
| DE2154245C3 (de) | 3-Hydrazino-6-(2-hydroxypropylamino)-pyridazinderivate, Verfahren zu ihrer Herstellung und sie enthaltendes pharmazeutisches Präparat | |
| DE3103372A1 (de) | Neue indanyl-derivate, ihre herstellung und verwendung | |
| EP1713768A2 (de) | Neue kristalline formen von entacapone und deren herstellung | |
| EP0100516B1 (de) | 3-Beta-(3'-(Carboxypropionyloxy))-ursa-9(11),12-dien-28-carbonsäure sowie ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0027268A2 (de) | Chinazolin-Derivate, Verfahren und Zwischenprodukte zu deren Herstellung, Arzneimittel enthaltend solche Chinazolin-Derivate und deren pharmazeutische Verwendung | |
| WO1987004160A1 (en) | N,n'-(bisfurfuryl)-2-furylmethanediamine, its production and use | |
| DE3438244C2 (enrdf_load_stackoverflow) | ||
| DE3132025A1 (de) | Verfahren zur gewinnung von 1,2-dimethyl-5-nitroimidazol von hoher reinheit | |
| DE2137538C3 (de) | oxyamin und seine Salze sowie ein Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel | |
| DE2412388A1 (de) | Dibenzothiophenderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel | |
| DE2022694B2 (de) | alpha-(3,4-Dihydro-4-oxo-1 H-2,3benzothiazin-S-dioxyd-3-yl)-N,N-dimethylacetamid und Verfahren zur Herstellung desselben | |
| DE2629756C2 (enrdf_load_stackoverflow) | ||
| DE1493524A1 (de) | Aminosaeuren | |
| DE3107594A1 (de) | Neue piperazin-verbindungen, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2229931A1 (de) | Verfahren zur herstellung von neuen o-substituierten phenylaethylguanidinen | |
| DE2609574A1 (de) | Monosubstituiertes piperazinderivat, verfahren zu seiner herstellung und es enthaltende arzneimittel | |
| DE2607570A1 (de) | Triazolobenzocycloalkylthiadiazin- derivate, verfahren zu ihrer herstellung und dieselben enthaltende pharmazeutische praeparate | |
| AT344174B (de) | Verfahren zur herstellung neuer pyridinderivate und ihrer salze | |
| AT380232B (de) | Verfahren zur herstellung von neuen s(-)-3-(3-acetyl-4-(3-tert. butylamino-2hydroxypropoxy)-phenyl)-1,1-diaethylharnstoff und dessen pharmazeutisch vertraeglichen saeureadditionssalzen | |
| AT371440B (de) | Verfahren zur herstellung von neuen n-substituierten moranolinderivaten und ihrer saeureadditionssalze | |
| EP0035723B1 (de) | 2,4-Diamino-5-sulfamoylbenzolsulfosäuren und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): JP US |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH DE FR GB IT LU NL SE |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 1987900067 Country of ref document: EP |
|
| WWP | Wipo information: published in national office |
Ref document number: 1987900067 Country of ref document: EP |
|
| WWW | Wipo information: withdrawn in national office |
Ref document number: 1987900067 Country of ref document: EP |