PL83580B1 - - Google Patents
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- Publication number
- PL83580B1 PL83580B1 PL1972157841A PL15784172A PL83580B1 PL 83580 B1 PL83580 B1 PL 83580B1 PL 1972157841 A PL1972157841 A PL 1972157841A PL 15784172 A PL15784172 A PL 15784172A PL 83580 B1 PL83580 B1 PL 83580B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- ethyl
- acid
- pyrrolidylmethyl
- methoxy
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 claims description 2
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- -1 1-ethyl Chemical group 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000010992 reflux Methods 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/08—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 no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH881372A CH562790A5 (zh) | 1972-06-13 | 1972-06-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83580B1 true PL83580B1 (zh) | 1975-12-31 |
Family
ID=4345021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1972157841A PL83580B1 (zh) | 1972-06-13 | 1972-09-20 |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS565733B2 (zh) |
| AR (1) | AR193288A1 (zh) |
| AT (1) | AT316536B (zh) |
| AU (1) | AU464143B2 (zh) |
| BE (1) | BE787180A (zh) |
| BG (1) | BG20575A3 (zh) |
| CA (1) | CA976554A (zh) |
| CH (1) | CH562790A5 (zh) |
| CS (1) | CS181712B2 (zh) |
| DD (1) | DD100249A5 (zh) |
| DE (1) | DE2246799A1 (zh) |
| EG (1) | EG10796A (zh) |
| ES (1) | ES407141A1 (zh) |
| FI (1) | FI59243C (zh) |
| FR (1) | FR2187782B1 (zh) |
| GB (1) | GB1345494A (zh) |
| HU (1) | HU165916B (zh) |
| IE (1) | IE36719B1 (zh) |
| IL (1) | IL40503A (zh) |
| IT (1) | IT1034031B (zh) |
| LU (1) | LU65860A1 (zh) |
| MC (1) | MC938A1 (zh) |
| NL (1) | NL7213128A (zh) |
| NO (1) | NO140347C (zh) |
| OA (1) | OA04167A (zh) |
| PL (1) | PL83580B1 (zh) |
| RO (1) | RO60562A (zh) |
| SE (1) | SE385695B (zh) |
| YU (1) | YU35119B (zh) |
| ZA (1) | ZA726084B (zh) |
| ZM (1) | ZM15172A1 (zh) |
-
0
- BE BE787180D patent/BE787180A/xx not_active IP Right Cessation
-
1971
- 1971-08-24 AR AR243725A patent/AR193288A1/es active
-
1972
- 1972-06-13 CH CH881372A patent/CH562790A5/xx not_active IP Right Cessation
- 1972-08-07 LU LU65860A patent/LU65860A1/xx unknown
- 1972-08-22 MC MC1007A patent/MC938A1/xx unknown
- 1972-08-30 IT IT28620/72A patent/IT1034031B/it active
- 1972-08-31 FR FR7230990A patent/FR2187782B1/fr not_active Expired
- 1972-09-02 OA OA54681A patent/OA04167A/xx unknown
- 1972-09-04 GB GB4087072A patent/GB1345494A/en not_active Expired
- 1972-09-06 ZA ZA726084A patent/ZA726084B/xx unknown
- 1972-09-07 AU AU46416/72A patent/AU464143B2/en not_active Expired
- 1972-09-12 NO NO3232/72A patent/NO140347C/no unknown
- 1972-09-12 SE SE7211723A patent/SE385695B/xx unknown
- 1972-09-14 CA CA151,723A patent/CA976554A/en not_active Expired
- 1972-09-15 FI FI2549/72A patent/FI59243C/fi active
- 1972-09-15 CS CS7200006345A patent/CS181712B2/cs unknown
- 1972-09-18 HU HUEA921A patent/HU165916B/hu unknown
- 1972-09-19 IE IE1280/72A patent/IE36719B1/xx unknown
- 1972-09-19 ZM ZM151/72*UA patent/ZM15172A1/xx unknown
- 1972-09-20 PL PL1972157841A patent/PL83580B1/pl unknown
- 1972-09-21 AT AT812672A patent/AT316536B/de not_active IP Right Cessation
- 1972-09-23 DE DE19722246799 patent/DE2246799A1/de active Pending
- 1972-09-25 YU YU2421/72A patent/YU35119B/xx unknown
- 1972-09-28 NL NL7213128A patent/NL7213128A/xx unknown
- 1972-09-29 ES ES407141A patent/ES407141A1/es not_active Expired
- 1972-09-29 DD DD165950A patent/DD100249A5/xx unknown
- 1972-09-30 RO RO72382A patent/RO60562A/ro unknown
- 1972-10-04 IL IL40503A patent/IL40503A/xx unknown
- 1972-10-12 BG BG021603A patent/BG20575A3/xx unknown
- 1972-12-28 EG EG547/72A patent/EG10796A/xx active
-
1973
- 1973-02-01 JP JP1332573A patent/JPS565733B2/ja not_active Expired
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