DE2427614A1 - Neue pyrrolderivate und verfahren zu ihrer herstellung - Google Patents
Neue pyrrolderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2427614A1 DE2427614A1 DE19742427614 DE2427614A DE2427614A1 DE 2427614 A1 DE2427614 A1 DE 2427614A1 DE 19742427614 DE19742427614 DE 19742427614 DE 2427614 A DE2427614 A DE 2427614A DE 2427614 A1 DE2427614 A1 DE 2427614A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compound
- pyrrole
- halogen atom
- pharmaceutical preparations
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 21
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- -1 1 -chlorophenoxy Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 210000002966 serum Anatomy 0.000 claims description 7
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003233 pyrroles Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- NNTMDTSGHWLWKT-UHFFFAOYSA-N (5-acetyloxyoxolan-2-yl) acetate Chemical compound CC(=O)OC1CCC(OC(C)=O)O1 NNTMDTSGHWLWKT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 2
- 239000003524 antilipemic agent Substances 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
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- 238000002844 melting Methods 0.000 description 10
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- 239000012362 glacial acetic acid Substances 0.000 description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 description 4
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- GZYGYLSHLHOMAO-UHFFFAOYSA-N 2,5-dimethoxy-2-methyloxolane Chemical compound COC1CCC(C)(OC)O1 GZYGYLSHLHOMAO-UHFFFAOYSA-N 0.000 description 2
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- SMWBBLSINLFYAB-UHFFFAOYSA-N 4-(4-fluorophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(F)C=C1 SMWBBLSINLFYAB-UHFFFAOYSA-N 0.000 description 2
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000008063 acylals Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- 238000005899 aromatization reaction Methods 0.000 description 2
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- 230000008025 crystallization Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 239000008187 granular material Substances 0.000 description 2
- MWVFCEVNXHTDNF-UHFFFAOYSA-N hexane-2,3-dione Chemical compound CCCC(=O)C(C)=O MWVFCEVNXHTDNF-UHFFFAOYSA-N 0.000 description 2
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- OSWWFLDIIGGSJV-UHFFFAOYSA-N 1,4-diphenylbutane-1,4-dione Chemical compound C=1C=CC=CC=1C(=O)CCC(=O)C1=CC=CC=C1 OSWWFLDIIGGSJV-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- RZPAUHPZAQVFNZ-UHFFFAOYSA-N 2,5-dibromooxolane Chemical compound BrC1CCC(Br)O1 RZPAUHPZAQVFNZ-UHFFFAOYSA-N 0.000 description 1
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- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-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)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742427614 DE2427614A1 (de) | 1974-06-07 | 1974-06-07 | Neue pyrrolderivate und verfahren zu ihrer herstellung |
| ZA00753093A ZA753093B (en) | 1974-06-07 | 1975-05-13 | New pyrrol derivatives and process for the manufacture |
| AU81230/75A AU8123075A (en) | 1974-06-07 | 1975-05-16 | New pyrrol derivatives and process for the manufacture of these compounds |
| ES437972A ES437972A1 (es) | 1974-06-07 | 1975-05-27 | Procedimiento para la obtencion de nuevos derivados del pi- rrol. |
| SE7506295A SE7506295L (sv) | 1974-06-07 | 1975-06-02 | Sett att framstella nya pyrrolderivat |
| DK248575A DK248575A (da) | 1974-06-07 | 1975-06-03 | Fremgangsmade til fremstilling af pyrrolderivater |
| GB23913/75A GB1501196A (en) | 1974-06-07 | 1975-06-03 | Pyrrole derivatives and process for the manufacture of these compounds |
| JP50067110A JPS5113764A (cg-RX-API-DMAC7.html) | 1974-06-07 | 1975-06-05 | |
| NL7506753A NL7506753A (nl) | 1974-06-07 | 1975-06-06 | Werkwijze voor het bereiden van nieuwe pyrrool- derivaten. |
| NO752014A NO752014L (cg-RX-API-DMAC7.html) | 1974-06-07 | 1975-06-06 | |
| FR7517760A FR2273534A1 (fr) | 1974-06-07 | 1975-06-06 | Nouveaux derives du pyrrole, leur obtention, et composition pharmaceutique qui les contient |
| BE157107A BE829963A (fr) | 1974-06-07 | 1975-06-06 | Procede de preparation de nouveaux derives du pyrrole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742427614 DE2427614A1 (de) | 1974-06-07 | 1974-06-07 | Neue pyrrolderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2427614A1 true DE2427614A1 (de) | 1976-01-02 |
Family
ID=5917589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742427614 Pending DE2427614A1 (de) | 1974-06-07 | 1974-06-07 | Neue pyrrolderivate und verfahren zu ihrer herstellung |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5113764A (cg-RX-API-DMAC7.html) |
| AU (1) | AU8123075A (cg-RX-API-DMAC7.html) |
| BE (1) | BE829963A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2427614A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK248575A (cg-RX-API-DMAC7.html) |
| ES (1) | ES437972A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2273534A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1501196A (cg-RX-API-DMAC7.html) |
| NL (1) | NL7506753A (cg-RX-API-DMAC7.html) |
| NO (1) | NO752014L (cg-RX-API-DMAC7.html) |
| SE (1) | SE7506295L (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA753093B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2705778A1 (de) * | 1976-02-12 | 1977-08-18 | Chinoin Gyogyszer Es Vegyeszet | Kondensierte pyrimidinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014199164A1 (en) * | 2013-06-12 | 2014-12-18 | Ampla Pharmaceuticals, Inc. | Diaryl substituted heteroaromatic compounds |
-
1974
- 1974-06-07 DE DE19742427614 patent/DE2427614A1/de active Pending
-
1975
- 1975-05-13 ZA ZA00753093A patent/ZA753093B/xx unknown
- 1975-05-16 AU AU81230/75A patent/AU8123075A/en not_active Expired
- 1975-05-27 ES ES437972A patent/ES437972A1/es not_active Expired
- 1975-06-02 SE SE7506295A patent/SE7506295L/xx unknown
- 1975-06-03 DK DK248575A patent/DK248575A/da unknown
- 1975-06-03 GB GB23913/75A patent/GB1501196A/en not_active Expired
- 1975-06-05 JP JP50067110A patent/JPS5113764A/ja active Pending
- 1975-06-06 NO NO752014A patent/NO752014L/no unknown
- 1975-06-06 BE BE157107A patent/BE829963A/xx unknown
- 1975-06-06 NL NL7506753A patent/NL7506753A/xx unknown
- 1975-06-06 FR FR7517760A patent/FR2273534A1/fr not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2705778A1 (de) * | 1976-02-12 | 1977-08-18 | Chinoin Gyogyszer Es Vegyeszet | Kondensierte pyrimidinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| BE829963A (fr) | 1975-12-08 |
| ES437972A1 (es) | 1977-01-16 |
| ZA753093B (en) | 1976-04-28 |
| JPS5113764A (cg-RX-API-DMAC7.html) | 1976-02-03 |
| SE7506295L (sv) | 1975-12-08 |
| GB1501196A (en) | 1978-02-15 |
| NL7506753A (nl) | 1975-12-09 |
| AU8123075A (en) | 1976-11-18 |
| DK248575A (da) | 1975-12-08 |
| NO752014L (cg-RX-API-DMAC7.html) | 1975-12-09 |
| FR2273534A1 (fr) | 1976-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |