CH532037A - Verfahren zur Herstellung von Pyrrolverbindungen - Google Patents
Verfahren zur Herstellung von PyrrolverbindungenInfo
- Publication number
- CH532037A CH532037A CH1355570A CH1355570A CH532037A CH 532037 A CH532037 A CH 532037A CH 1355570 A CH1355570 A CH 1355570A CH 1355570 A CH1355570 A CH 1355570A CH 532037 A CH532037 A CH 532037A
- Authority
- CH
- Switzerland
- Prior art keywords
- solvent
- formula
- reaction
- mixture
- amino
- Prior art date
Links
- -1 amino- Chemical class 0.000 title claims description 7
- 150000003233 pyrroles Chemical class 0.000 title abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 4
- 238000009833 condensation Methods 0.000 claims abstract 2
- 230000005494 condensation Effects 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SKNIWUSHIRPONJ-UHFFFAOYSA-N 2-amino-2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(C(N)C#N)C=C1 SKNIWUSHIRPONJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- PZWWXCPIPRJHNG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one Chemical compound COC1=CC=C(C=CC(=O)C(C)(C)C)C=C1 PZWWXCPIPRJHNG-UHFFFAOYSA-N 0.000 description 1
- ZIXVMEYRFPMOAV-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-methylpent-1-en-3-one Chemical compound COC1=CC=C(C=CC(=O)C(C)C)C=C1 ZIXVMEYRFPMOAV-UHFFFAOYSA-N 0.000 description 1
- HISPXTCMDDBNTK-UHFFFAOYSA-N 1-(4-methoxyphenyl)-5-methylhex-1-en-3-one Chemical compound COC1=CC=C(C=CC(=O)CC(C)C)C=C1 HISPXTCMDDBNTK-UHFFFAOYSA-N 0.000 description 1
- SLDQOBRACOQXGE-UHFFFAOYSA-N 1-(4-methoxyphenyl)pent-1-en-3-one Chemical compound CCC(=O)C=CC1=CC=C(OC)C=C1 SLDQOBRACOQXGE-UHFFFAOYSA-N 0.000 description 1
- WGVQZBURQZKDBN-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-1h-pyrrole Chemical group C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC=C1 WGVQZBURQZKDBN-UHFFFAOYSA-N 0.000 description 1
- JTIHSSVKTWPPHI-UHFFFAOYSA-N 2-amino-2-phenylacetonitrile Chemical class N#CC(N)C1=CC=CC=C1 JTIHSSVKTWPPHI-UHFFFAOYSA-N 0.000 description 1
- UUKRKWJGNHNTRG-UHFFFAOYSA-N 4-(4-chlorophenyl)but-3-en-2-one Chemical compound CC(=O)C=CC1=CC=C(Cl)C=C1 UUKRKWJGNHNTRG-UHFFFAOYSA-N 0.000 description 1
- WRRZKDVBPZBNJN-UHFFFAOYSA-N 4-(4-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(C=CC(C)=O)C=C1 WRRZKDVBPZBNJN-UHFFFAOYSA-N 0.000 description 1
- USXMUOFSQBSHGN-UHFFFAOYSA-N 4-(4-methylphenyl)but-3-en-2-one Chemical compound CC(=O)C=CC1=CC=C(C)C=C1 USXMUOFSQBSHGN-UHFFFAOYSA-N 0.000 description 1
- ZXFOZOLHXOFXMN-UHFFFAOYSA-N 4-[2-(4-methoxyphenyl)-5-methyl-1H-pyrrol-3-yl]-N,N-dimethylaniline Chemical compound CC1=CC(=C(N1)C1=CC=C(C=C1)OC)C1=CC=C(C=C1)N(C)C ZXFOZOLHXOFXMN-UHFFFAOYSA-N 0.000 description 1
- IAMOQOMGCKCSEJ-UHFFFAOYSA-N 4-[4-(dimethylamino)phenyl]but-3-en-2-one Chemical compound CN(C)C1=CC=C(C=CC(C)=O)C=C1 IAMOQOMGCKCSEJ-UHFFFAOYSA-N 0.000 description 1
- SGYZRXDPUYQURP-UHFFFAOYSA-N 5-ethyl-2,3-bis(4-methoxyphenyl)-1H-pyrrole Chemical compound C(C)C=1NC(=C(C1)C1=CC=C(C=C1)OC)C1=CC=C(C=C1)OC SGYZRXDPUYQURP-UHFFFAOYSA-N 0.000 description 1
- IJZPUNJYBSHEJK-UHFFFAOYSA-N 5-methyl-2,3-diphenyl-1h-pyrrole Chemical group N1C(C)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IJZPUNJYBSHEJK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- NYKIPMCSAKJNKN-UHFFFAOYSA-N benzyl(trimethyl)azanium;butan-1-olate Chemical compound CCCC[O-].C[N+](C)(C)CC1=CC=CC=C1 NYKIPMCSAKJNKN-UHFFFAOYSA-N 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44072253A JPS4838705B1 (enrdf_load_stackoverflow) | 1969-09-11 | 1969-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH532037A true CH532037A (de) | 1972-12-31 |
Family
ID=13483929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1355570A CH532037A (de) | 1969-09-11 | 1970-09-11 | Verfahren zur Herstellung von Pyrrolverbindungen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4838705B1 (enrdf_load_stackoverflow) |
| AT (1) | AT294816B (enrdf_load_stackoverflow) |
| CH (1) | CH532037A (enrdf_load_stackoverflow) |
| ES (1) | ES383433A1 (enrdf_load_stackoverflow) |
| NL (1) | NL7012853A (enrdf_load_stackoverflow) |
| OA (1) | OA03656A (enrdf_load_stackoverflow) |
| SE (1) | SE367190B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4335136A (en) * | 1980-04-18 | 1982-06-15 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 4,5-diaryl-α-(polyfluoroalkyl)-1H-pyrrole-2-methanamines |
| US4318917A (en) * | 1981-01-21 | 1982-03-09 | E. I. Du Pont De Nemours And Company | Antiinflammatory 2,3-diaryl-5-[2,2,2-trifluoro-1-(trifluoromethyl]ethyl-1H-pyrroles |
-
1969
- 1969-09-11 JP JP44072253A patent/JPS4838705B1/ja active Pending
-
1970
- 1970-08-31 NL NL7012853A patent/NL7012853A/xx unknown
- 1970-09-02 AT AT796670A patent/AT294816B/de not_active IP Right Cessation
- 1970-09-05 ES ES383433A patent/ES383433A1/es not_active Expired
- 1970-09-08 OA OA54026A patent/OA03656A/xx unknown
- 1970-09-11 CH CH1355570A patent/CH532037A/de not_active IP Right Cessation
- 1970-09-11 SE SE12355/70A patent/SE367190B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4838705B1 (enrdf_load_stackoverflow) | 1973-11-19 |
| NL7012853A (enrdf_load_stackoverflow) | 1971-03-15 |
| OA03656A (fr) | 1971-12-24 |
| ES383433A1 (es) | 1973-02-16 |
| AT294816B (de) | 1971-12-10 |
| SE367190B (enrdf_load_stackoverflow) | 1974-05-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2366625C2 (enrdf_load_stackoverflow) | ||
| DE2047658B2 (de) | 2-Styryl- und 2-Phenyläthinylbenzylaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE1545575C2 (de) | N, N'-Bis- eckige Klammer auf 3"(3', 4', 5'-trimethoxybenzoyloxy)-propyl eckige Klammer zu -homopiperazin | |
| DD272648A5 (de) | Chromon-derivate | |
| CH626058A5 (en) | Process for the preparation of basic oxime ethers | |
| EP0380712B1 (de) | Verfahren zur Herstellung von 2,6-Dichlordiphenylaminessigsäurederivaten | |
| DE2623226C2 (de) | N-Benzyl-2,2-dimethoxy-acetamide, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1618465B2 (de) | Phenylessigsäureester, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| CH532037A (de) | Verfahren zur Herstellung von Pyrrolverbindungen | |
| DE69818988T2 (de) | 9,10-diazatryclo[4.2.11 2,5]decan- und 9,10-diazatricyclo[3.3.1.1 2,6]decanderive mit analgetischer wirkung | |
| DE2000030B2 (de) | 3 Alkoxy und 3 Phenoxy 2 (diphenyl hydroxy)methyl propylamine und diese enthaltende Arzneimittel | |
| CH591415A5 (en) | 3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder | |
| DE2354931C2 (de) | trans-2-Phenylbicyclooctan-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen | |
| CH356121A (de) | Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren | |
| CH369759A (de) | Verfahren zur Herstellung von N-Alkylpiperidin-a-carbonsäureaniliden | |
| CH533619A (de) | Verfahren zur Herstellung von Pyrrolderivaten | |
| DE3873720T2 (de) | Nicotinoylpiperazin-derivate, verfahren zu ihrer herstellung und ihre verwendung in der therapie. | |
| AT258955B (de) | Verfahren zur Herstellung neuer Bis(hydroxymethyl)pyridindicarbamat-Derivate | |
| DE2020762A1 (de) | Azainden-3-niedrigaliphatische-Saeuren und Verfahren zu deren Herstellung | |
| EP0303179A1 (de) | Neue 1,2-Diamino-Verbindungen, Verfahren zu ihrer Herstellung sowie Arzneimittel, die diese Verbindungen enthalten | |
| DE2118929A1 (de) | Acy lvinylary lalkan-(und-alken)säuren | |
| AT250338B (de) | Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen | |
| AT336626B (de) | Verfahren zur herstellung von neuen n,n'-disubstituierten cyclischen diaminen und deren saureadditionssalzen | |
| AT200136B (de) | Verfahren zur Herstellung von neuen tertiären Aminen der Tetrahydrofuranreihe | |
| AT200145B (de) | Verfahren zur Herstellung von neuen N-2-Pyridyl-N-halogenbenzyl-N',N'-dialkyläthylendiaminen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |