CS251791B2 - Method of pyrrole's new condensed derivatives production - Google Patents
Method of pyrrole's new condensed derivatives production Download PDFInfo
- Publication number
- CS251791B2 CS251791B2 CS855249A CS524985A CS251791B2 CS 251791 B2 CS251791 B2 CS 251791B2 CS 855249 A CS855249 A CS 855249A CS 524985 A CS524985 A CS 524985A CS 251791 B2 CS251791 B2 CS 251791B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- nebo nebo
- pyrrolo
- dihydro
- het
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- CYXQJHOJIQTXLE-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolizine Chemical compound C1=CN2CCCC2=C1 CYXQJHOJIQTXLE-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- QYASHELNMUPRKF-UHFFFAOYSA-N 5,6,7,8-tetrahydroindolizine Chemical group C1CCCN2C=CC=C21 QYASHELNMUPRKF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- TZQCKFFLFFLNTB-UHFFFAOYSA-N 1,3-dihydropyrrolo[1,2-c][1,3]oxazole Chemical compound C1=CC=C2COCN21 TZQCKFFLFFLNTB-UHFFFAOYSA-N 0.000 claims description 2
- JGQIVJMIHAAARZ-UHFFFAOYSA-N 3,4-dihydro-1h-pyrrolo[1,2-c][1,3]oxazine Chemical compound C1OCCC2=CC=CN21 JGQIVJMIHAAARZ-UHFFFAOYSA-N 0.000 claims description 2
- ZIOSTPPOTIQPII-UHFFFAOYSA-N 3,4-dihydro-1h-pyrrolo[1,2-c][1,3]thiazine Chemical compound C1SCCC2=CC=CN21 ZIOSTPPOTIQPII-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- AAUBAPMXIKRIIH-UHFFFAOYSA-N 1,3-dihydropyrrolo[1,2-c][1,3]thiazole Chemical compound C1=CC=C2CSCN21 AAUBAPMXIKRIIH-UHFFFAOYSA-N 0.000 claims 2
- QJDNWKOTFOHJDB-UHFFFAOYSA-N 2,3-dihydropyrrolo[2,1-b][1,3]oxazole Chemical compound C1=CC=C2OCCN21 QJDNWKOTFOHJDB-UHFFFAOYSA-N 0.000 claims 2
- ZSXJQVNQZXSAOV-UHFFFAOYSA-N 2,3-dihydropyrrolo[2,1-b][1,3]thiazole Chemical compound C1=CC=C2SCCN21 ZSXJQVNQZXSAOV-UHFFFAOYSA-N 0.000 claims 1
- JXDSQFQCABPXRH-UHFFFAOYSA-N OC1CN2C(S1)=CC=C2 Chemical group OC1CN2C(S1)=CC=C2 JXDSQFQCABPXRH-UHFFFAOYSA-N 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000000047 product Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- -1 heterocyclic radical Chemical class 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 description 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YPELFRMCRYSPKZ-UHFFFAOYSA-N 4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzamide Chemical group CCOC1=CC(N)=C(Cl)C=C1C(=O)NCC1OCCN(CC=2C=CC(F)=CC=2)C1 YPELFRMCRYSPKZ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000734147 Anema Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000755093 Gaidropsarus vulgaris Species 0.000 description 1
- 229920006063 Lamide® Polymers 0.000 description 1
- 241001611408 Nebo Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 210000003254 palate Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- NDUWNWVXAYLZSO-UHFFFAOYSA-N pyrrolidin-2-ol Chemical compound OC1CCCN1 NDUWNWVXAYLZSO-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- IJOUCDYZGQFHNL-UHFFFAOYSA-N thiazinane-4-carboxylic acid Chemical compound OC(=O)C1CCSNC1 IJOUCDYZGQFHNL-UHFFFAOYSA-N 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8320474A FR2557111B1 (fr) | 1983-12-21 | 1983-12-21 | Nouveaux derives ortho-condenses du pyrrole, leur preparation et les medicaments qui les contiennent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS524985A2 CS524985A2 (en) | 1986-12-18 |
| CS251791B2 true CS251791B2 (en) | 1987-08-13 |
Family
ID=9295399
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS855249A CS251791B2 (en) | 1983-12-21 | 1984-12-21 | Method of pyrrole's new condensed derivatives production |
| CS855248A CS251790B2 (en) | 1983-12-21 | 1984-12-21 | Method of pyrrole's new condensed derivatives production |
| CS8410201A CS251782B2 (en) | 1983-12-21 | 1984-12-21 | Method of pyrrole's new condensed derivatives productio( |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS855248A CS251790B2 (en) | 1983-12-21 | 1984-12-21 | Method of pyrrole's new condensed derivatives production |
| CS8410201A CS251782B2 (en) | 1983-12-21 | 1984-12-21 | Method of pyrrole's new condensed derivatives productio( |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4684658A (fi) |
| EP (1) | EP0147317A3 (fi) |
| JP (1) | JPS60172977A (fi) |
| KR (1) | KR850004768A (fi) |
| AU (1) | AU573666B2 (fi) |
| CA (1) | CA1250286A (fi) |
| CS (3) | CS251791B2 (fi) |
| DK (1) | DK616584A (fi) |
| FI (1) | FI76809C (fi) |
| FR (1) | FR2557111B1 (fi) |
| HU (2) | HU194238B (fi) |
| IL (1) | IL73888A (fi) |
| NZ (1) | NZ210671A (fi) |
| SU (2) | SU1436883A3 (fi) |
| ZA (1) | ZA849958B (fi) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3915450A1 (de) * | 1989-05-11 | 1990-11-15 | Gerd Prof Dr Dannhardt | Substituierte pyrrolverbindungen und deren anwendung in der pharmazie |
| US5260451A (en) * | 1989-05-11 | 1993-11-09 | Merckle Gmbh | Substituted pyrrole compounds and use thereof in pharmaceutical compositions |
| JPH05501103A (ja) * | 1989-06-26 | 1993-03-04 | ザ・リサーチ・ファウンデーション・オヴ・ステイト・ユニヴァーシティ・オヴ・ニューヨーク | ビス―アシルオキシメチル誘導体 |
| US5395846A (en) * | 1993-06-25 | 1995-03-07 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Amino Bi- and tri-carbocyclic aklane bis-aryl squalene synthase inhibitors |
| DE4419246A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteroarylsubstituierte Pyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| DE4419247A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie |
| DE4419315A1 (de) * | 1994-06-01 | 1995-12-07 | Merckle Gmbh | Heteropyrrolizinverbindungen und deren Anwendung in der Pharmazie |
| FR2735476B1 (fr) * | 1995-06-14 | 1997-07-18 | Rhone Poulenc Rorer Sa | Nouvelle application de derives du pyrrole |
| FR2757166B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Derives du pyrrole, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2757059B1 (fr) * | 1996-12-12 | 1999-01-29 | Rhone Poulenc Rorer Sa | Nouvelle application therapeutique des derives du pyrrole |
| US6191925B1 (en) | 1999-06-18 | 2001-02-20 | Storage Technology Corporation | Dual element read with shaped elements |
| HUP0204336A3 (en) | 1999-11-23 | 2006-01-30 | Merckle Gmbh | Anti-inflammatory oxo derivatives and hydroxy derivatives of pyrrolizines, and their pharmaceutical use and pharmaceutical compositions containing them their |
| DE10004157A1 (de) | 2000-02-01 | 2001-08-02 | Merckle Gmbh Chem Pharm Fabrik | 4-Pyridyl-und 2,4-Pyrimidinyl-substituierte Pyrrolderivate und ihre Anwendung in der Pharmazie |
| CN1930124A (zh) * | 2004-03-08 | 2007-03-14 | 贝林格尔·英格海姆药物公司 | 制备交叉偶联吲哚的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3429885A (en) * | 1965-10-22 | 1969-02-25 | American Home Prod | Pyridylethyl and piperidylethyl pyrroles |
| GB1174124A (en) * | 1967-06-30 | 1969-12-10 | Beecham Group Ltd | Pharmacologically Active Indolizine Compounds |
| FR2539417A1 (fr) * | 1983-01-13 | 1984-07-20 | Rhone Poulenc Sante | Nouveaux pyrrolo-1, 2 heterocycles, leur preparation et les medicaments qui les contiennent |
| FR2541280B1 (fr) * | 1983-01-13 | 1985-06-21 | Rhone Poulenc Sante | Nouveaux derives du 1h, 3h-pyrrolo (1,2c) thiazolecarboxamide-7, leur preparation et les medicaments qui les contiennent |
| GR81681B (fi) * | 1983-01-13 | 1984-12-12 | Rhone Poulenc Sante |
-
1983
- 1983-12-21 FR FR8320474A patent/FR2557111B1/fr not_active Expired
-
1984
- 1984-12-20 NZ NZ210671A patent/NZ210671A/xx unknown
- 1984-12-20 HU HU844758A patent/HU194238B/hu not_active IP Right Cessation
- 1984-12-20 HU HU844960A patent/HU196801B/hu not_active IP Right Cessation
- 1984-12-20 KR KR1019840008153A patent/KR850004768A/ko not_active Withdrawn
- 1984-12-20 FI FI845064A patent/FI76809C/fi not_active IP Right Cessation
- 1984-12-20 SU SU843826152A patent/SU1436883A3/ru active
- 1984-12-20 JP JP59267581A patent/JPS60172977A/ja active Pending
- 1984-12-20 US US06/684,061 patent/US4684658A/en not_active Expired - Fee Related
- 1984-12-20 EP EP84402675A patent/EP0147317A3/fr not_active Withdrawn
- 1984-12-20 AU AU36960/84A patent/AU573666B2/en not_active Ceased
- 1984-12-20 DK DK616584A patent/DK616584A/da not_active Application Discontinuation
- 1984-12-20 IL IL73888A patent/IL73888A/xx unknown
- 1984-12-20 ZA ZA849958A patent/ZA849958B/xx unknown
- 1984-12-20 CA CA000470656A patent/CA1250286A/fr not_active Expired
- 1984-12-21 CS CS855249A patent/CS251791B2/cs unknown
- 1984-12-21 CS CS855248A patent/CS251790B2/cs unknown
- 1984-12-21 CS CS8410201A patent/CS251782B2/cs unknown
-
1985
- 1985-09-23 SU SU853954499A patent/SU1440349A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| FI845064A0 (fi) | 1984-12-20 |
| IL73888A (en) | 1987-11-30 |
| ZA849958B (en) | 1985-08-28 |
| JPS60172977A (ja) | 1985-09-06 |
| HU196801B (en) | 1989-01-30 |
| FR2557111A1 (fr) | 1985-06-28 |
| FI76809C (fi) | 1988-12-12 |
| FI76809B (fi) | 1988-08-31 |
| CS524985A2 (en) | 1986-12-18 |
| EP0147317A3 (fr) | 1986-06-25 |
| FI845064L (fi) | 1985-06-22 |
| CA1250286A (fr) | 1989-02-21 |
| DK616584D0 (da) | 1984-12-20 |
| AU573666B2 (en) | 1988-06-16 |
| CS251790B2 (en) | 1987-08-13 |
| SU1440349A3 (ru) | 1988-11-23 |
| IL73888A0 (en) | 1985-03-31 |
| DK616584A (da) | 1985-06-22 |
| CS524885A2 (en) | 1986-12-18 |
| SU1436883A3 (ru) | 1988-11-07 |
| CS251782B2 (en) | 1987-08-13 |
| US4684658A (en) | 1987-08-04 |
| EP0147317A2 (fr) | 1985-07-03 |
| AU3696084A (en) | 1985-07-04 |
| HUT40435A (en) | 1986-12-28 |
| HU194238B (en) | 1988-01-28 |
| KR850004768A (ko) | 1985-07-27 |
| NZ210671A (en) | 1989-08-29 |
| FR2557111B1 (fr) | 1986-04-11 |
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