NO122299B - - Google Patents
Download PDFInfo
- Publication number
- NO122299B NO122299B NO327868A NO327868A NO122299B NO 122299 B NO122299 B NO 122299B NO 327868 A NO327868 A NO 327868A NO 327868 A NO327868 A NO 327868A NO 122299 B NO122299 B NO 122299B
- Authority
- NO
- Norway
- Prior art keywords
- phenthiazine
- carboxylate
- formula
- methyl
- activity
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000006114 decarboxylation reaction Methods 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000001414 amino alcohols Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 20
- 239000000047 product Substances 0.000 description 13
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000739 antihistaminic agent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- 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 5
- 230000009471 action Effects 0.000 description 5
- 230000001387 anti-histamine Effects 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229940125715 antihistaminic agent Drugs 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- FZASHPCRPMSFEG-UHFFFAOYSA-N 3-(dimethylamino)-2-methylpropan-1-ol Chemical compound OCC(C)CN(C)C FZASHPCRPMSFEG-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000003193 general anesthetic agent Substances 0.000 description 2
- 239000003326 hypnotic agent Substances 0.000 description 2
- 230000000147 hypnotic effect Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- -1 3-dimethylamino-2-methyl-1-propyl- Chemical group 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229940124326 anaesthetic agent Drugs 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 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
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42F—SHEETS TEMPORARILY ATTACHED TOGETHER; FILING APPLIANCES; FILE CARDS; INDEXING
- B42F21/00—Indexing means; Indexing tabs or protectors therefor
- B42F21/06—Tabs detachably mounted on sheets, papers, cards, or suspension files
- B42F21/08—Tabs detachably mounted on sheets, papers, cards, or suspension files in one of a number of predetermined positions
Landscapes
- Sheet Holders (AREA)
- Clamps And Clips (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671536625 DE1536625C3 (de) | 1967-08-25 | 1967-08-25 | Hängebehältnis für Schriftgut |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122299B true NO122299B (enrdf_load_stackoverflow) | 1971-06-14 |
Family
ID=5675848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO327868A NO122299B (enrdf_load_stackoverflow) | 1967-08-25 | 1968-08-21 |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT291191B (enrdf_load_stackoverflow) |
| BE (1) | BE719840A (enrdf_load_stackoverflow) |
| FR (1) | FR1577104A (enrdf_load_stackoverflow) |
| GB (1) | GB1228255A (enrdf_load_stackoverflow) |
| NO (1) | NO122299B (enrdf_load_stackoverflow) |
| SE (1) | SE341817B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2808482C2 (de) * | 1978-02-28 | 1986-06-12 | Elba-Ordner-Fabrik Kraut & Meienborn GmbH & Co., 5600 Wuppertal | Kennzeichnungsreiter |
-
1968
- 1968-04-23 FR FR1577104D patent/FR1577104A/fr not_active Expired
- 1968-07-23 AT AT07091/68A patent/AT291191B/de not_active IP Right Cessation
- 1968-08-09 SE SE1076068A patent/SE341817B/xx unknown
- 1968-08-14 GB GB1228255D patent/GB1228255A/en not_active Expired
- 1968-08-21 NO NO327868A patent/NO122299B/no unknown
- 1968-08-23 BE BE719840D patent/BE719840A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR1577104A (enrdf_load_stackoverflow) | 1969-08-01 |
| SE341817B (enrdf_load_stackoverflow) | 1972-01-17 |
| AT291191B (de) | 1971-06-15 |
| BE719840A (enrdf_load_stackoverflow) | 1969-02-03 |
| GB1228255A (enrdf_load_stackoverflow) | 1971-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69130120T2 (de) | Derivate von zyklischen Amiden | |
| DE68927875T2 (de) | N-substituierte azaheterocyclische Carbonsäuren | |
| NO177590B (no) | Analogifremgangsmåte for fremstilling av terapeutisk aktive cykliske aminforbindelser | |
| JP2005015486A (ja) | 塩酸ドネペジルの多形結晶およびその製造法 | |
| DE2300491A1 (de) | Neue pyrrolo eckige klammer auf 3,4-b eckige klammer zu pyrazinderivate, ihre herstellung und die medizinischen zusammensetzungen, die sie enthalten | |
| NO321267B1 (no) | Polymorfe av donepezilhydroklorid, fremgangsmater for fremstilling derav, anvendelse derav samt terapeutisk preparat inneholdende den samme. | |
| JPH03188077A (ja) | 新規なベンズイソキサゾール誘導体及び該誘導体を含有する製剤組成物 | |
| JPH0153671B2 (enrdf_load_stackoverflow) | ||
| JPS6360968A (ja) | キノリン誘導体 | |
| EP3110808B1 (en) | Plant growth regulating compounds | |
| RU2099328C1 (ru) | Производные метанантрацена, способы их получения и фармацевтическая композиция, обладающая антидопаминергической активностью | |
| EP3173409B1 (en) | Plant growth regulating compounds | |
| DE4115215A1 (de) | Indolderivate | |
| US4808595A (en) | Furopyridine sulfonamides and their opthalmological compositions | |
| DD209446A5 (de) | Verfahren zur herstellung von neuen aromatischen verbindungen | |
| US3428652A (en) | Anguidine derivatives | |
| US4025630A (en) | Anesthesia methods using benzopyrans and esters thereof as pre-anesthesia medication | |
| JPS6348267A (ja) | ４−ベンジルピペラジン誘導体類、それらの製造およびそれらを含有している薬学的組成物類 | |
| EP0091512B1 (en) | 6-fluoro-3-(3-(1-heterocyclo)propyl)-1,2-benzisoxazoles, a process for their preparation, pharmaceutical compositions thereof and their use as medicaments | |
| NO122299B (enrdf_load_stackoverflow) | ||
| JPH085863B2 (ja) | １４−アニソイルアコニンおよびそれを有効成分とする新規な鎮痛・抗炎症剤 | |
| US4442106A (en) | Quinoline derivatives, pharmaceutical compositions containing such compounds, and methods of treating cardiovascular conditions with them | |
| US3471505A (en) | 1-(alkoxyphenyl)-1-(3-pyridyl)-carbinols | |
| ES2642805T3 (es) | Sal de un derivado del ácido pirrolidín-3-ilacético y cristales de esta | |
| NO164498B (no) | Spenneanordning. |