NO125390B - - Google Patents
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- Publication number
- NO125390B NO125390B NO4660/68A NO466068A NO125390B NO 125390 B NO125390 B NO 125390B NO 4660/68 A NO4660/68 A NO 4660/68A NO 466068 A NO466068 A NO 466068A NO 125390 B NO125390 B NO 125390B
- Authority
- NO
- Norway
- Prior art keywords
- phenthiazine
- denotes
- general formula
- carbon atoms
- propyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 7
- 230000008673 vomiting Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- 206010047700 Vomiting Diseases 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- SATRZZYUXUGZIE-UHFFFAOYSA-N heptyl carbonochloridate Chemical compound CCCCCCCOC(Cl)=O SATRZZYUXUGZIE-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 230000003474 anti-emetic effect Effects 0.000 description 2
- 239000002111 antiemetic agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- AZZCHVHSWUYCQA-UHFFFAOYSA-N decyl carbonochloridate Chemical compound CCCCCCCCCCOC(Cl)=O AZZCHVHSWUYCQA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- HOQUWXSARQBQCW-UHFFFAOYSA-N hexadecyl carbonochloridate Chemical compound CCCCCCCCCCCCCCCCOC(Cl)=O HOQUWXSARQBQCW-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
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-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
- 150000001298 alcohols 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
- 150000001450 anions Chemical class 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000053 physical method Methods 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
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR129636 | 1967-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125390B true NO125390B (xx) | 1972-09-04 |
Family
ID=8642251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4660/68A NO125390B (xx) | 1967-11-24 | 1968-11-22 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3627759A (xx) |
| AT (1) | AT281050B (xx) |
| BE (1) | BE724365A (xx) |
| BR (1) | BR6804139D0 (xx) |
| CH (1) | CH484189A (xx) |
| DE (1) | DE1810422A1 (xx) |
| DK (1) | DK124551B (xx) |
| ES (1) | ES360630A1 (xx) |
| FI (1) | FI49421C (xx) |
| FR (1) | FR1578731A (xx) |
| GB (1) | GB1203380A (xx) |
| IE (1) | IE32500B1 (xx) |
| IL (1) | IL31143A (xx) |
| NL (1) | NL6816326A (xx) |
| NO (1) | NO125390B (xx) |
| SE (1) | SE356982B (xx) |
| YU (1) | YU32392B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2175565A1 (en) * | 1972-03-14 | 1973-10-26 | Roussel Uclaf | 10-(4-alkoxy-4-alkylpiperidinoalkyl)phenothiazines - - with neuroleptic,antihistaminic,analgesic and spasmolytic activity |
| US3956493A (en) * | 1974-10-21 | 1976-05-11 | E. R. Squibb & Sons, Inc. | Long acting tranquilizing agent |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3282934A (en) * | 1964-05-15 | 1966-11-01 | Schering Corp | Nitrogenous esters of hydroxylalkylamino phenothiazines |
-
1967
- 1967-11-24 FR FR129636A patent/FR1578731A/fr not_active Expired
-
1968
- 1968-10-25 FI FI683040A patent/FI49421C/fi active
- 1968-11-15 NL NL6816326A patent/NL6816326A/xx unknown
- 1968-11-19 BR BR204139/68A patent/BR6804139D0/pt unknown
- 1968-11-21 IE IE1410/68A patent/IE32500B1/xx unknown
- 1968-11-21 US US777862A patent/US3627759A/en not_active Expired - Lifetime
- 1968-11-22 YU YU2740/68A patent/YU32392B/xx unknown
- 1968-11-22 IL IL31143A patent/IL31143A/xx unknown
- 1968-11-22 DK DK571168AA patent/DK124551B/da unknown
- 1968-11-22 DE DE19681810422 patent/DE1810422A1/de active Pending
- 1968-11-22 CH CH1744768A patent/CH484189A/fr not_active IP Right Cessation
- 1968-11-22 SE SE15976/68A patent/SE356982B/xx unknown
- 1968-11-22 AT AT1135768A patent/AT281050B/de not_active IP Right Cessation
- 1968-11-22 NO NO4660/68A patent/NO125390B/no unknown
- 1968-11-22 GB GB55497/68A patent/GB1203380A/en not_active Expired
- 1968-11-22 BE BE724365D patent/BE724365A/xx unknown
- 1968-11-23 ES ES360630A patent/ES360630A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH484189A (fr) | 1970-01-15 |
| BR6804139D0 (pt) | 1973-01-11 |
| US3627759A (en) | 1971-12-14 |
| IE32500L (en) | 1969-05-24 |
| YU274068A (en) | 1974-04-30 |
| AT281050B (de) | 1970-05-11 |
| NL6816326A (xx) | 1969-05-28 |
| IE32500B1 (en) | 1973-08-22 |
| ES360630A1 (es) | 1970-07-16 |
| DK124551B (da) | 1972-10-30 |
| DE1810422A1 (de) | 1969-07-10 |
| BE724365A (xx) | 1969-05-22 |
| FR1578731A (xx) | 1969-08-22 |
| IL31143A (en) | 1973-06-29 |
| YU32392B (en) | 1974-10-31 |
| GB1203380A (en) | 1970-08-26 |
| FI49421C (fi) | 1975-06-10 |
| IL31143A0 (en) | 1969-01-29 |
| SE356982B (xx) | 1973-06-12 |
| FI49421B (xx) | 1975-02-28 |
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