PL89285B1 - - Google Patents
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- Publication number
- PL89285B1 PL89285B1 PL1973161336A PL16133673A PL89285B1 PL 89285 B1 PL89285 B1 PL 89285B1 PL 1973161336 A PL1973161336 A PL 1973161336A PL 16133673 A PL16133673 A PL 16133673A PL 89285 B1 PL89285 B1 PL 89285B1
- Authority
- PL
- Poland
- Prior art keywords
- amino
- dichlorophenyl
- general formula
- tert
- formula
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- 150000002917 oxazolidines Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- -1 4-amino-3,5-dichlorophenyl Chemical group 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZTMVQAJEIJZAOS-UHFFFAOYSA-N 4-(3-tert-butyl-1,3-oxazolidin-5-yl)-2,6-dichloroaniline hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C1CN(CO1)C(C)(C)C)Cl ZTMVQAJEIJZAOS-UHFFFAOYSA-N 0.000 description 1
- FPZFVMRKDKEFOR-UHFFFAOYSA-N 4-(3-tert-butyl-2-propyl-1,3-oxazolidin-5-yl)-2,6-dichloroaniline Chemical compound NC1=C(C=C(C=C1Cl)C1CN(C(O1)CCC)C(C)(C)C)Cl FPZFVMRKDKEFOR-UHFFFAOYSA-N 0.000 description 1
- UCKAOVIIJJQUTL-UHFFFAOYSA-N 4-(3-tert-butyl-2h-1,3-oxazol-5-yl)-2,6-dichloroaniline Chemical compound CC(C)(C)N1COC(C=2C=C(Cl)C(N)=C(Cl)C=2)=C1 UCKAOVIIJJQUTL-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- AYRYKJJSHXPDGG-UHFFFAOYSA-N C(C)C1OC(CN1C(C)(C)C)C1=CC(=C(C(=C1)Cl)N)Cl Chemical compound C(C)C1OC(CN1C(C)(C)C)C1=CC(=C(C(=C1)Cl)N)Cl AYRYKJJSHXPDGG-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NRTBYORYFFFYAE-UHFFFAOYSA-N NC1=C(C=C(C=C1Cl)C1CN(C(O1)C1=C(C=CC=C1)Cl)C(C)(C)C)Cl Chemical compound NC1=C(C=C(C=C1Cl)C1CN(C(O1)C1=C(C=CC=C1)Cl)C(C)(C)C)Cl NRTBYORYFFFYAE-UHFFFAOYSA-N 0.000 description 1
- UGBZHLSTRRCAFE-UHFFFAOYSA-N NC1=C(C=C(C=C1Cl)C1CN(C(O1)C1=CC=CC=C1)C(C)(C)C)Cl Chemical compound NC1=C(C=C(C=C1Cl)C1CN(C(O1)C1=CC=CC=C1)C(C)(C)C)Cl UGBZHLSTRRCAFE-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GYLDXXLJMRTVSS-UHFFFAOYSA-N n-butylacetamide Chemical group CCCCNC(C)=O GYLDXXLJMRTVSS-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722213271 DE2213271C3 (de) | 1972-03-18 | 1972-03-18 | Neue oxazolidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL89285B1 true PL89285B1 (enEXAMPLES) | 1976-11-30 |
Family
ID=5839379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973161336A PL89285B1 (enEXAMPLES) | 1972-03-18 | 1973-03-17 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US3896141A (enEXAMPLES) |
| JP (1) | JPS5123504B2 (enEXAMPLES) |
| KR (1) | KR780000135B1 (enEXAMPLES) |
| AT (1) | AT321907B (enEXAMPLES) |
| AU (1) | AU470947B2 (enEXAMPLES) |
| BE (1) | BE796941A (enEXAMPLES) |
| BG (1) | BG22825A3 (enEXAMPLES) |
| CA (1) | CA996554A (enEXAMPLES) |
| CH (1) | CH577491A5 (enEXAMPLES) |
| CS (1) | CS179981B2 (enEXAMPLES) |
| DD (1) | DD108276A5 (enEXAMPLES) |
| DE (1) | DE2213271C3 (enEXAMPLES) |
| DK (1) | DK133431C (enEXAMPLES) |
| ES (1) | ES412734A1 (enEXAMPLES) |
| FI (1) | FI55655C (enEXAMPLES) |
| FR (1) | FR2181829B1 (enEXAMPLES) |
| GB (1) | GB1386751A (enEXAMPLES) |
| HU (1) | HU165157B (enEXAMPLES) |
| IE (1) | IE37419B1 (enEXAMPLES) |
| IL (1) | IL41795A (enEXAMPLES) |
| NL (1) | NL173640C (enEXAMPLES) |
| NO (1) | NO136977C (enEXAMPLES) |
| PH (1) | PH9990A (enEXAMPLES) |
| PL (1) | PL89285B1 (enEXAMPLES) |
| RO (1) | RO62878A (enEXAMPLES) |
| SE (1) | SE381660B (enEXAMPLES) |
| SU (1) | SU468424A3 (enEXAMPLES) |
| YU (1) | YU35008B (enEXAMPLES) |
| ZA (1) | ZA731832B (enEXAMPLES) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4754047A (en) * | 1979-08-16 | 1988-06-28 | American Cyanamid Company | Phenylethanolamine derivatives and acid addition salts thereof for enhancing the growth rate of meat-producing animals and/or improving the efficiency of feed utilization thereby |
| JPS57161479A (en) * | 1981-03-29 | 1982-10-05 | Kankiyou Souken Consultant Kk | Improvement in melting furnace with preheating column utilizing exhaust gas |
| US4603422A (en) * | 1984-09-26 | 1986-07-29 | The United States Of America As Represented By The Secretary Of The Navy | Long-lived laser dye |
| US5149821A (en) * | 1990-10-11 | 1992-09-22 | Pfizer Inc | Process and intermediates for optically active 3-formyltetrahydropyrans |
-
1972
- 1972-03-18 DE DE19722213271 patent/DE2213271C3/de not_active Expired
-
1973
- 1973-02-27 DD DD169086A patent/DD108276A5/xx unknown
- 1973-03-06 AT AT194673A patent/AT321907B/de not_active IP Right Cessation
- 1973-03-08 US US339389A patent/US3896141A/en not_active Expired - Lifetime
- 1973-03-09 PH PH14412*A patent/PH9990A/en unknown
- 1973-03-13 SU SU1893863A patent/SU468424A3/ru active
- 1973-03-14 CH CH373073A patent/CH577491A5/xx not_active IP Right Cessation
- 1973-03-14 CS CS7300001852A patent/CS179981B2/cs unknown
- 1973-03-15 SE SE7303640A patent/SE381660B/xx unknown
- 1973-03-15 JP JP48030473A patent/JPS5123504B2/ja not_active Expired
- 1973-03-15 YU YU693/73A patent/YU35008B/xx unknown
- 1973-03-16 NL NLAANVRAGE7303685,A patent/NL173640C/xx not_active IP Right Cessation
- 1973-03-16 NO NO1060/73A patent/NO136977C/no unknown
- 1973-03-16 DK DK144673A patent/DK133431C/da not_active IP Right Cessation
- 1973-03-16 CA CA166,241A patent/CA996554A/en not_active Expired
- 1973-03-16 ES ES412734A patent/ES412734A1/es not_active Expired
- 1973-03-16 HU HUTO901A patent/HU165157B/hu unknown
- 1973-03-16 BE BE128942A patent/BE796941A/xx not_active IP Right Cessation
- 1973-03-16 IE IE439/73A patent/IE37419B1/xx unknown
- 1973-03-16 FR FR7309578A patent/FR2181829B1/fr not_active Expired
- 1973-03-16 IL IL41795A patent/IL41795A/xx unknown
- 1973-03-16 BG BG023014A patent/BG22825A3/xx unknown
- 1973-03-16 AU AU53394/73A patent/AU470947B2/en not_active Expired
- 1973-03-16 FI FI823/73A patent/FI55655C/fi active
- 1973-03-16 GB GB1284173A patent/GB1386751A/en not_active Expired
- 1973-03-16 ZA ZA00731832A patent/ZA731832B/xx unknown
- 1973-03-17 PL PL1973161336A patent/PL89285B1/pl unknown
- 1973-03-17 KR KR7300430A patent/KR780000135B1/ko not_active Expired
- 1973-03-19 RO RO7300074211A patent/RO62878A/ro unknown
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