DE2222931C3 - Piperidinoalkylphenthiazine, Verfahren zur Herstellung derselben sowie diese enthaltende pharmazeutische Mittel - Google Patents
Piperidinoalkylphenthiazine, Verfahren zur Herstellung derselben sowie diese enthaltende pharmazeutische MittelInfo
- Publication number
- DE2222931C3 DE2222931C3 DE2222931A DE2222931A DE2222931C3 DE 2222931 C3 DE2222931 C3 DE 2222931C3 DE 2222931 A DE2222931 A DE 2222931A DE 2222931 A DE2222931 A DE 2222931A DE 2222931 C3 DE2222931 C3 DE 2222931C3
- Authority
- DE
- Germany
- Prior art keywords
- phenthiazine
- trifluoromethyl
- propyl
- piperidino
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 13
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 208000022821 personality disease Diseases 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 150000002990 phenothiazines Chemical group 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000012345 traction test Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or 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 to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or 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 to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hetero atoms or 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 to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
-
- 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)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7117510A FR2137150B1 (enExample) | 1971-05-14 | 1971-05-14 | |
| FR717117509A FR2137149B1 (enExample) | 1971-05-14 | 1971-05-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2222931A1 DE2222931A1 (de) | 1972-11-30 |
| DE2222931B2 DE2222931B2 (de) | 1977-11-10 |
| DE2222931C3 true DE2222931C3 (de) | 1978-07-06 |
Family
ID=26216390
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2222931A Expired DE2222931C3 (de) | 1971-05-14 | 1972-05-10 | Piperidinoalkylphenthiazine, Verfahren zur Herstellung derselben sowie diese enthaltende pharmazeutische Mittel |
| DE2264903A Expired DE2264903C3 (de) | 1971-05-14 | 1972-05-10 | Piperidinderivate und ihre Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2264903A Expired DE2264903C3 (de) | 1971-05-14 | 1972-05-10 | Piperidinderivate und ihre Herstellung |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS5118958B1 (enExample) |
| AU (1) | AU461649B2 (enExample) |
| BE (1) | BE783411A (enExample) |
| CH (1) | CH553215A (enExample) |
| DE (2) | DE2222931C3 (enExample) |
| DK (1) | DK142318B (enExample) |
| FI (1) | FI55657C (enExample) |
| FR (2) | FR2137150B1 (enExample) |
| GB (2) | GB1383774A (enExample) |
| IL (1) | IL39296A (enExample) |
| NL (1) | NL175824C (enExample) |
| NO (1) | NO135365C (enExample) |
| SE (2) | SE405973B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0621267A1 (en) * | 1993-04-07 | 1994-10-26 | Shell Internationale Researchmaatschappij B.V. | Spiropiperidine derivatives and their use as fungicides |
| EP1345917A1 (en) * | 2000-12-19 | 2003-09-24 | Ucb, S.A. | 2-(2-(4-((2r)-2-methyl-3-(10h-phenothiazin-10-yl)propyl)-1-piperazinyl)-ethoxy)ethanol, process for the preparation thereof, pharmaceutical compositions containing said compound and therapeutic uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1344593A (fr) * | 1961-11-25 | 1963-11-29 | Boehringer & Soehne Gmbh | Procédé pour la préparation de nouveaux dérivés de l'alcoxy-pipéridine et de leurs sels |
-
1971
- 1971-05-14 FR FR7117510A patent/FR2137150B1/fr not_active Expired
- 1971-05-14 FR FR717117509A patent/FR2137149B1/fr not_active Expired
-
1972
- 1972-04-25 IL IL39296A patent/IL39296A/en unknown
- 1972-04-27 CH CH629072A patent/CH553215A/fr not_active IP Right Cessation
- 1972-05-09 FI FI1305/72A patent/FI55657C/fi active
- 1972-05-09 SE SE7206146A patent/SE405973B/xx unknown
- 1972-05-10 DE DE2222931A patent/DE2222931C3/de not_active Expired
- 1972-05-10 DE DE2264903A patent/DE2264903C3/de not_active Expired
- 1972-05-12 BE BE783411A patent/BE783411A/xx not_active IP Right Cessation
- 1972-05-12 NO NO1690/72A patent/NO135365C/no unknown
- 1972-05-12 AU AU42226/72A patent/AU461649B2/en not_active Expired
- 1972-05-13 JP JP47046917A patent/JPS5118958B1/ja active Pending
- 1972-05-15 NL NLAANVRAGE7206504,A patent/NL175824C/xx not_active IP Right Cessation
- 1972-05-15 DK DK240672AA patent/DK142318B/da not_active IP Right Cessation
- 1972-05-15 GB GB3172274A patent/GB1383774A/en not_active Expired
- 1972-05-15 GB GB2277272A patent/GB1383773A/en not_active Expired
-
1975
- 1975-05-06 SE SE7505250A patent/SE418964B/xx unknown
- 1975-11-25 JP JP50140299A patent/JPS5248988B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL39296A0 (en) | 1972-06-28 |
| NL7206504A (enExample) | 1972-11-16 |
| DK142318B (da) | 1980-10-13 |
| SE405973B (sv) | 1979-01-15 |
| AU461649B2 (en) | 1975-06-05 |
| FI55657B (fi) | 1979-05-31 |
| DE2222931A1 (de) | 1972-11-30 |
| JPS5248988B2 (enExample) | 1977-12-14 |
| NL175824B (nl) | 1984-08-01 |
| NL175824C (nl) | 1985-01-02 |
| FR2137149A1 (enExample) | 1972-12-29 |
| BE783411A (fr) | 1972-11-13 |
| SE418964B (sv) | 1981-07-06 |
| JPS5191267A (enExample) | 1976-08-10 |
| FR2137150B1 (enExample) | 1975-01-17 |
| FR2137149B1 (enExample) | 1973-05-11 |
| DK142318C (enExample) | 1981-03-02 |
| DE2264903A1 (de) | 1975-08-28 |
| FI55657C (fi) | 1979-09-10 |
| IL39296A (en) | 1976-03-31 |
| DE2264903C3 (de) | 1981-12-17 |
| CH553215A (fr) | 1974-08-30 |
| GB1383774A (en) | 1974-02-12 |
| SE7505250L (enExample) | 1975-05-06 |
| AU4222672A (en) | 1973-12-06 |
| DE2264903B2 (de) | 1981-02-19 |
| JPS5118958B1 (enExample) | 1976-06-14 |
| GB1383773A (en) | 1974-02-12 |
| DE2222931B2 (de) | 1977-11-10 |
| NO135365B (enExample) | 1976-12-20 |
| NO135365C (no) | 1977-03-30 |
| FR2137150A1 (enExample) | 1972-12-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |