AT396590B - Verfahren zur herstellung von - Google Patents
Verfahren zur herstellung von Download PDFInfo
- Publication number
- AT396590B AT396590B AT0252985A AT252985A AT396590B AT 396590 B AT396590 B AT 396590B AT 0252985 A AT0252985 A AT 0252985A AT 252985 A AT252985 A AT 252985A AT 396590 B AT396590 B AT 396590B
- Authority
- AT
- Austria
- Prior art keywords
- groups
- carbon atoms
- hydroxy
- furo
- group
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical class N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- AVZNLXBMQVKETP-UHFFFAOYSA-M [Br-].CN(C)CC([Mg+])=C Chemical compound [Br-].CN(C)CC([Mg+])=C AVZNLXBMQVKETP-UHFFFAOYSA-M 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 239000000047 product Substances 0.000 description 21
- 239000000155 melt Substances 0.000 description 19
- 239000007858 starting material Substances 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229960000317 yohimbine Drugs 0.000 description 11
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- KEKQEYBOTHGIGL-UHFFFAOYSA-N 7-hydroxyfuro[3,4-c]pyridine-6-carbaldehyde Chemical class C(=O)C1=C(C=2C(C=N1)=COC2)O KEKQEYBOTHGIGL-UHFFFAOYSA-N 0.000 description 3
- 208000009132 Catalepsy Diseases 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010047853 Waxy flexibility Diseases 0.000 description 3
- 229940090044 injection Drugs 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- KNDAEDDIIQYRHY-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazin-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCNCC1 KNDAEDDIIQYRHY-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- VOTLWZVQCVFRKZ-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound ClC1=C(C=CC=C1Cl)C1OCC2=C1C=NC(=C2O)C=O VOTLWZVQCVFRKZ-UHFFFAOYSA-N 0.000 description 1
- ZQBKYDIVYUVOKL-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-(hydroxymethyl)-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound ClC1=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)CO ZQBKYDIVYUVOKL-UHFFFAOYSA-N 0.000 description 1
- VVZFVTBHZIUIGP-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methyl-5-oxido-1,3-dihydrofuro[3,4-c]pyridin-5-ium-7-ol Chemical compound ClC1=CC=C(C=C1)C1OCC2=C1C=[N+](C(=C2O)C)[O-] VVZFVTBHZIUIGP-UHFFFAOYSA-N 0.000 description 1
- PJAFKGLPUVYSMP-UHFFFAOYSA-N 3-(4-chlorophenyl)-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound ClC1=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)C=O PJAFKGLPUVYSMP-UHFFFAOYSA-N 0.000 description 1
- BWRYFRVJZRDRFL-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-7-hydroxy-3-phenyl-1H-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(=CC=CC=C1)C1(OCC2=C1C=NC(=C2O)C=O)C2=CC=C(C=C2)OCC BWRYFRVJZRDRFL-UHFFFAOYSA-N 0.000 description 1
- XBKVOJFQPQOLBI-UHFFFAOYSA-N 3-cyclohexyl-7-hydroxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(CCCCC1)C1OCC2=C1C=NC(=C2O)C=O XBKVOJFQPQOLBI-UHFFFAOYSA-N 0.000 description 1
- UXHQLGLGLZKHTC-CUNXSJBXSA-N 4-[(3s,3ar)-3-cyclopentyl-7-(4-hydroxypiperidine-1-carbonyl)-3,3a,4,5-tetrahydropyrazolo[3,4-f]quinolin-2-yl]-2-chlorobenzonitrile Chemical compound C1CC(O)CCN1C(=O)C1=CC=C(C=2[C@@H]([C@H](C3CCCC3)N(N=2)C=2C=C(Cl)C(C#N)=CC=2)CC2)C2=N1 UXHQLGLGLZKHTC-CUNXSJBXSA-N 0.000 description 1
- IKWMZNFDXDHOOL-UHFFFAOYSA-N 7-hydroxy-3-(4-methoxyphenyl)-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound COC1=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)C=O IKWMZNFDXDHOOL-UHFFFAOYSA-N 0.000 description 1
- ULWXXAZYIAWHTF-UHFFFAOYSA-N 7-hydroxy-3-(4-methylphenyl)-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1(=CC=C(C=C1)C1OCC2=C1C=NC(=C2O)C=O)C ULWXXAZYIAWHTF-UHFFFAOYSA-N 0.000 description 1
- FQMJBWZGARBBPM-UHFFFAOYSA-N 7-hydroxy-3-methyl-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1=NC(C=O)=C(O)C2=C1C(C)OC2 FQMJBWZGARBBPM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- GJVNMIQVQXYJCP-UHFFFAOYSA-N furo[3,4-c]pyridine Chemical class C1=NC=CC2=[C]OC=C21 GJVNMIQVQXYJCP-UHFFFAOYSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 229940047551 haloperidol injection Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 description 1
- 229960004090 maprotiline Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 125000002734 organomagnesium group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848422029A GB8422029D0 (en) | 1984-08-31 | 1984-08-31 | 6-substituted-furo-(3 4-c)-pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA252985A ATA252985A (de) | 1993-02-15 |
| AT396590B true AT396590B (de) | 1993-10-25 |
Family
ID=10566078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0252985A AT396590B (de) | 1984-08-31 | 1985-08-29 | Verfahren zur herstellung von |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS6160688A (en, 2012) |
| AR (1) | AR241455A1 (en, 2012) |
| AT (1) | AT396590B (en, 2012) |
| BE (1) | BE903122A (en, 2012) |
| CA (1) | CA1300149C (en, 2012) |
| CH (1) | CH666688A5 (en, 2012) |
| DE (1) | DE3531004A1 (en, 2012) |
| DK (1) | DK157871C (en, 2012) |
| ES (1) | ES8604967A1 (en, 2012) |
| FI (1) | FI82468C (en, 2012) |
| FR (1) | FR2569698B1 (en, 2012) |
| GB (2) | GB8422029D0 (en, 2012) |
| HK (1) | HK6189A (en, 2012) |
| IE (1) | IE58522B1 (en, 2012) |
| IT (1) | IT1201459B (en, 2012) |
| LU (1) | LU86052A1 (en, 2012) |
| NL (1) | NL8502324A (en, 2012) |
| NO (1) | NO162071C (en, 2012) |
| OA (1) | OA08088A (en, 2012) |
| PT (1) | PT81054B (en, 2012) |
| SE (1) | SE462218B (en, 2012) |
| ZA (1) | ZA856088B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | Pyridine derivatives |
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| DE10323602A1 (de) * | 2003-05-19 | 2004-12-16 | Südzucker AG Mannheim/Ochsenfurt | Hartkaramellen mit geträgerten Farbstoffen |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT366687B (de) * | 1977-11-25 | 1982-04-26 | Scras | Verfahren zur herstellung des neuen 1,3 dihydro - 3 - (3',4',5'-trimethoxystyryl) -6methyl - 7 -hydroxy - furo - (3,4,c)-pyridins |
| AT383806B (de) * | 1983-04-05 | 1987-08-25 | Scras | Verfahren zur herstellung neuer verbindungen von furo-(3,4-c)-pyridinderivaten und von deren salzen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2153824B (en) * | 1984-02-02 | 1987-04-01 | Scras | Furo-(3,4-c)-pyridine derivatives |
-
1984
- 1984-08-31 GB GB848422029A patent/GB8422029D0/en active Pending
-
1985
- 1985-08-12 GB GB08520169A patent/GB2163744B/en not_active Expired
- 1985-08-12 ZA ZA856088A patent/ZA856088B/xx unknown
- 1985-08-19 SE SE8503869A patent/SE462218B/sv not_active IP Right Cessation
- 1985-08-20 AR AR85301339A patent/AR241455A1/es active
- 1985-08-22 LU LU86052A patent/LU86052A1/fr unknown
- 1985-08-22 CA CA000489219A patent/CA1300149C/en not_active Expired - Lifetime
- 1985-08-23 CH CH3653/85A patent/CH666688A5/fr not_active IP Right Cessation
- 1985-08-23 NL NL8502324A patent/NL8502324A/nl not_active Application Discontinuation
- 1985-08-26 BE BE0/215502A patent/BE903122A/fr not_active IP Right Cessation
- 1985-08-28 FI FI853287A patent/FI82468C/fi not_active IP Right Cessation
- 1985-08-29 AT AT0252985A patent/AT396590B/de not_active IP Right Cessation
- 1985-08-30 PT PT81054A patent/PT81054B/pt not_active IP Right Cessation
- 1985-08-30 IE IE214385A patent/IE58522B1/en not_active IP Right Cessation
- 1985-08-30 FR FR8512917A patent/FR2569698B1/fr not_active Expired
- 1985-08-30 JP JP60190033A patent/JPS6160688A/ja active Granted
- 1985-08-30 DK DK396085A patent/DK157871C/da not_active IP Right Cessation
- 1985-08-30 OA OA58669A patent/OA08088A/xx unknown
- 1985-08-30 NO NO853418A patent/NO162071C/no unknown
- 1985-08-30 ES ES546590A patent/ES8604967A1/es not_active Expired
- 1985-08-30 DE DE19853531004 patent/DE3531004A1/de active Granted
- 1985-08-30 IT IT22035/85A patent/IT1201459B/it active
-
1989
- 1989-01-19 HK HK61/89A patent/HK6189A/xx not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT366687B (de) * | 1977-11-25 | 1982-04-26 | Scras | Verfahren zur herstellung des neuen 1,3 dihydro - 3 - (3',4',5'-trimethoxystyryl) -6methyl - 7 -hydroxy - furo - (3,4,c)-pyridins |
| AT383806B (de) * | 1983-04-05 | 1987-08-25 | Scras | Verfahren zur herstellung neuer verbindungen von furo-(3,4-c)-pyridinderivaten und von deren salzen |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT391700B (de) | Verfahren zur herstellung neuer 6-substituierter furo-(3,4-c)-pyridinderivate | |
| DE2614406C2 (en, 2012) | ||
| AT391867B (de) | Verfahren zur herstellung neuer 6-vinyl-furo(3,4-c)-pyridinderivate | |
| DE2149249B2 (de) | 4-Amino-6-arylpyrimidine | |
| DE2444322A1 (de) | Triazolopyridazine und verfahren zu deren herstellung | |
| CH626344A5 (en, 2012) | ||
| DE2604748A1 (de) | Aminoderivate von imidazo(4,5-b) pyridinen | |
| DE1518764B2 (de) | In der 7-SteUung substituierte S-Phenyl^-oxo^-dihydro-lH-M-benzodiazepin-3-carbonsäuresalze und -alkylester | |
| AT396590B (de) | Verfahren zur herstellung von | |
| DE2647041A1 (de) | 3-aminomethylen-6,7-dimethoxy-2- methyl-4-oxo-1,2,3,4-tetrahydro-1- chinolincarbonsaeureester und zwischenprodukte zur herstellung derselben | |
| AT391699B (de) | Verfahren zur herstellung neuer 4-chloro substituierter furo-(3,4-c)-pyridinderivate | |
| AT394558B (de) | Verfahren zur herstellung neuer 6-phenaethylaminoalkyl-7-hydroxy-furo-(3,4-c)pyridinderivate | |
| DE2746550C2 (en, 2012) | ||
| DE1695812B2 (de) | Dibenzo [cfl -1,2-thiazepin-derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitung | |
| DE2423060A1 (de) | Aminoderivate von pyrazolopyridinketonen | |
| DE2346466A1 (de) | Neue pyrazolopyridobenzodiazepinone mit ihren salzen | |
| DE1470002A1 (de) | 5,6-Dihydromorphanthridinderivate | |
| DE2034588C3 (de) | 6,7-Dimethoxy-4-benzylisochinoline, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE2359359A1 (de) | Fluor-substituierte thioxanthene und verfahren zu deren herstellung sowie diese enthaltende pharmazeutische mittel | |
| AT394557B (de) | Verfahren zur herstellung neuer 6-aminomethyl-furo-(3,4-c)-pyridinderivate | |
| DE2550163A1 (de) | Neue derivate des eckige klammer auf 1,4 eckige klammer zu oxathiino eckige klammer auf 2,3-c eckige klammer zu pyrrols, deren herstellung und diese enthaltende zusammensetzungen | |
| DD142053A5 (de) | Verfahren zur herstellung von neuen thieno eckige klammer auf 3,2-c eckige klammer zu-und thieno eckige klammer auf 2,3-c eckige klammer zu pyridinen | |
| DE2410982C3 (de) | Arzneimitel mit Sedativ- und Tranquilizer-Wirkung | |
| DE1090215B (de) | Verfahren zur Herstellung von Phenthiazinderivaten | |
| DE2013023A1 (de) | 2,3,4,4a-Tetrahydro-10 H-I,2-oxazino (3,2-b)(1,3)benzoxazin-10-one |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |