NO133449B - - Google Patents
Download PDFInfo
- Publication number
- NO133449B NO133449B NO3184/71A NO318471A NO133449B NO 133449 B NO133449 B NO 133449B NO 3184/71 A NO3184/71 A NO 3184/71A NO 318471 A NO318471 A NO 318471A NO 133449 B NO133449 B NO 133449B
- Authority
- NO
- Norway
- Prior art keywords
- piperazinyl
- group
- phenthiazine
- propyl
- acid addition
- Prior art date
Links
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 11
- -1 cyano, methylthio, methanesulfonyl Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000004885 piperazines Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000005587 carbonate group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 26
- 239000000155 melt Substances 0.000 description 15
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000000703 anti-shock Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 150000004820 halides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000003152 motion sickness Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 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
- 230000001766 physiological effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3082871A GB1356379A (en) | 1970-08-27 | 1970-08-27 | Tetrazole derivatives |
| GB3082871 | 1971-07-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133449B true NO133449B (enrdf_load_stackoverflow) | 1976-01-26 |
| NO133449C NO133449C (enrdf_load_stackoverflow) | 1976-05-05 |
Family
ID=26260624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3184/71A NO133449C (enrdf_load_stackoverflow) | 1970-08-27 | 1971-08-26 |
Country Status (19)
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1489749A (fr) * | 1965-03-25 | 1967-07-28 | Fisons Pharmaceuticals Ltd | Procédé de préparation de composés bis-chromonylés et leurs dérivés |
| CA960223A (en) * | 1970-02-05 | 1974-12-31 | Mervyn E. Peel | Tetrazolyl chromones |
-
1970
- 1970-08-27 GB GB3082871A patent/GB1356379A/en not_active Expired
-
1971
- 1971-08-24 OA OA54344A patent/OA03910A/xx unknown
- 1971-08-25 HU HUFI492A patent/HU164233B/hu unknown
- 1971-08-25 CH CH733073A patent/CH544085A/fr not_active IP Right Cessation
- 1971-08-25 CH CH1247871A patent/CH544108A/fr not_active IP Right Cessation
- 1971-08-25 CH CH732773A patent/CH567016A5/xx unknown
- 1971-08-25 BG BG019891A patent/BG19182A3/xx unknown
- 1971-08-25 CH CH732673A patent/CH567015A5/xx not_active IP Right Cessation
- 1971-08-25 CH CH732973A patent/CH567017A5/xx not_active IP Right Cessation
- 1971-08-25 DE DE19712142556 patent/DE2142556A1/de active Pending
- 1971-08-26 DD DD157355A patent/DD95008A5/xx unknown
- 1971-08-26 IL IL37591A patent/IL37591A/xx unknown
- 1971-08-26 AT AT746471A patent/AT319943B/de not_active IP Right Cessation
- 1971-08-26 AU AU32805/71A patent/AU3280571A/en not_active Expired
- 1971-08-26 AR AR237589A patent/AR193042A1/es active
- 1971-08-26 LU LU63792D patent/LU63792A1/xx unknown
- 1971-08-26 FR FR7130935A patent/FR2103553B1/fr not_active Expired
- 1971-08-26 ES ES394550A patent/ES394550A1/es not_active Expired
- 1971-08-26 CU CU33570A patent/CU33570A/es unknown
- 1971-08-26 IE IE1073/71A patent/IE35567B1/xx unknown
- 1971-08-26 BE BE771818A patent/BE771818A/xx unknown
- 1971-08-26 NL NL7111790A patent/NL7111790A/xx unknown
- 1971-08-26 NO NO3184/71A patent/NO133449C/no unknown
- 1971-08-26 AT AT857573*1A patent/AT322553B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7111790A (enrdf_load_stackoverflow) | 1972-02-29 |
| BE771818A (fr) | 1972-02-28 |
| IE35567B1 (en) | 1976-03-18 |
| CU33570A (enrdf_load_stackoverflow) | 1974-02-13 |
| HU164233B (enrdf_load_stackoverflow) | 1974-01-28 |
| CH567015A5 (enrdf_load_stackoverflow) | 1975-09-30 |
| NO133449C (enrdf_load_stackoverflow) | 1976-05-05 |
| AR193042A1 (es) | 1973-03-30 |
| FR2103553B1 (enrdf_load_stackoverflow) | 1975-10-10 |
| IL37591A0 (en) | 1971-11-29 |
| ES394550A1 (es) | 1975-03-16 |
| CH567016A5 (enrdf_load_stackoverflow) | 1975-09-30 |
| BG19182A3 (bg) | 1975-04-30 |
| CH567017A5 (enrdf_load_stackoverflow) | 1975-09-30 |
| AT322553B (de) | 1975-05-26 |
| GB1356379A (en) | 1974-06-12 |
| IE35567L (en) | 1972-02-27 |
| IL37591A (en) | 1974-12-31 |
| AU3280571A (en) | 1973-03-01 |
| LU63792A1 (enrdf_load_stackoverflow) | 1972-04-04 |
| DD95008A5 (enrdf_load_stackoverflow) | 1973-01-12 |
| OA03910A (fr) | 1975-08-14 |
| CH544108A (fr) | 1973-11-15 |
| AT319943B (de) | 1975-01-10 |
| FR2103553A1 (enrdf_load_stackoverflow) | 1972-04-14 |
| DE2142556A1 (de) | 1972-03-02 |
| CH544085A (fr) | 1973-12-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60129210T2 (de) | Zyklische amid-derivate | |
| US5001130A (en) | Psychotropic heterobicycloalkylpiperazine derivatives | |
| DE69701298T2 (de) | Hydroxypyridin-Derivate, ihre Herstellung und ihre pharmazeutische Verwendung | |
| NO162965B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive alfa-(2-okso-2,4,5,6,7,7a-heksahydrotieno-(3,2-c)-5-pyridyl)-fenyl-eddiksyre-derivater. | |
| NO122814B (enrdf_load_stackoverflow) | ||
| DE69430752T2 (de) | Tetracyclische verbindungen | |
| BR112019024376A2 (pt) | composto de fórmula geral (i), ou sais farmaceuticamente aceitáveis destes, composição farmacêutica e uso dos compostos ou sais farmaceuticamente aceitáveis destes | |
| DE69123315T2 (de) | 6,7-Dihydro-3-Phenyl-1,2-benzisoxazol-4(5H)-one und -ole, ein Verfahren für ihre Herstellung und ihre Verwendung als Arzneimittel | |
| DE69011645T2 (de) | Cycloheptenopyridinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Antiulkusmitteln. | |
| US3960863A (en) | Pyrido[1,2-a]pyrimidinone derivatives | |
| NO138072B (no) | Bredb}ndsspiralantenne. | |
| DE69012653T2 (de) | Heterocyclische Triazin- oder Triazolo-Verbindungen mit Serotonin 2-Rezeptor-Antagonisten-Wirkung. | |
| US2979502A (en) | Phenthiazine derivatives | |
| EP0273176A2 (en) | Fused heterocyclic tetrahydroaminoquinolinols and related compounds, a process for their preparation and their use as medicaments | |
| US3822269A (en) | 6-aminoalkylamino-hexahydrophenanthridines useful as antiarrhythmic agents | |
| US3636041A (en) | 4 5-dihydro-7h-thieno(2 3-c)thiopyrans | |
| NO133449B (enrdf_load_stackoverflow) | ||
| NO130329B (enrdf_load_stackoverflow) | ||
| US3325497A (en) | Cycloheptatrienylpiperazines | |
| SE438857B (sv) | Sett att framstella kromonderivat | |
| US3536715A (en) | 2-lower alkyl-5-(omega-(4-phenyl-1-piperazinyl) lower alkyl)-2h-tetrazoles | |
| DE68907845T2 (de) | Verbrückte bicyclische 4-(4-(3-Benzisothiazolyl)-1-piperazinyl)-butylimide mit antipsychotischer Wirkung. | |
| US3822267A (en) | 1 substituted 4 piperazino cycloalkylthiazoles | |
| US3130194A (en) | Phenthiazine derivatives | |
| CS226901B1 (en) | Thiazoloisoquinoline derivatives |