IL39296A - 10-(4-(hydroxyalkoxy)piperidinoalkyl)-phenothiazine derivatives and process for preparing them - Google Patents
10-(4-(hydroxyalkoxy)piperidinoalkyl)-phenothiazine derivatives and process for preparing themInfo
- Publication number
- IL39296A IL39296A IL39296A IL3929672A IL39296A IL 39296 A IL39296 A IL 39296A IL 39296 A IL39296 A IL 39296A IL 3929672 A IL3929672 A IL 3929672A IL 39296 A IL39296 A IL 39296A
- Authority
- IL
- Israel
- Prior art keywords
- mineral
- addition salts
- organic acids
- formula
- alkyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000007524 organic acids Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 14
- 239000011707 mineral Substances 0.000 claims 14
- 150000007522 mineralic acids Chemical class 0.000 claims 14
- 235000005985 organic acids Nutrition 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 229950000688 phenothiazine Drugs 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229910052801 chlorine Chemical group 0.000 claims 2
- -1 piperidino alkyl phenothiazines Chemical class 0.000 claims 2
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical group [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000002990 phenothiazines Chemical class 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (3)
1. 1 represents a polymethoxy phenyl radical or an alkyl, alkenyl or alkoxy- alkyl radical, containing at most 18 carbon atoms or A represents a radical -COORg in which R^ represents a straight alkyl radical containing at most 15 carbon atoms.
2. 10-£3- (¾- -pheno thiazine and its addition salts with mineral or organic acids*
3. a-Chloro.lO- 3-t?.-(2-hydroJ[yethoxy).piperidinoJ.p™pyl-}. phenothiazine and its addition salts with mineral or organic acids* -2-trifluoromethyl-phenothiazlne and its addition salts with mineral or organic acids* 1 ) 10- ^(2»hydroxy-ethoxy)-. -methyl-piperidinoj -propyij -2-trifluoromethyl-phenothiazlne and its addition salts with mineral or organic acids* 15) 10-£3- j^- (2-he tanoyloxy-ethoxy)-4-methyl-piperidino^j-propylj -2-trifluoromethyl-phenothiazine and its addition salts with mineral or organic acids* 16 ) 10-(3- ethyl- -(2-hydroxy-ethoxy)-piperidino]-propyl} -2-trifluoromethyl-phenothiazine and its addition salts with mineral or organic acids* -propyl) -2-trlfluoromethyl-phenothiazine and its addition salts with mineral or organic acids* 18 ) 10- j¾-heptyl- - (2-hydroxy*ethoxy)-plperidinoJ-propyl)-2-trifiuoromethyl-phenothlazlne and its addition salts with mineral or organic acids* 19 ) (2-propioaylexy-ethoxy)-piperidino3-propyl)-2-trif,luoromethyl-phenothiazine and its addition salts with¾|.η 3ΕΚ¾1 or organic acids* 20) P ocess for preparing the piperidino alkyl phenothiazines according to Claim 1, as well as their addition salts with mineral or organic acids, characterized in that one reacts a halo eno alkyl-£0 phenothlazine of formula Ζχ in which X, B and p_ have the aforesaid meaning, and Y represents a chlorine or bromine atom, with a piperidine derivative of formula 3 in which A," Ζ·, R and n have the aforesaid meaning, and that, either 'one isolates the product of formula (1) obtained, and, if desired, reacts a mineral or organic acid with the said product so as to form its salt, or, when A in formula 1 of the product obtained represents a hydrogen atom, one reacts the said product either with an acid chloride of formula Cl-CO-R^, in which R^ has the aforesaid meaning, and then isolates the product of formula (1), in which A represents a radical -COR- thus obtained, and, if desired, reacts a mineral or organic acid with the said product so as to form its salt, or with an alkyl chloroforraate of formula C1-C0GR2, in which R2 has the aforesaid meaning, and then isolates the product of formula (1), in which A represents a radical -COOR thus obtained, and, if desired, reacts a mineral or organic acid with the said "product so as to form its salt. 1 ) The pharmaceutical compositions containing as the active principle at least one of the piperldino alkyl phenothiazines according to any of Claims 1 to 19 and of their addition salts with pharmaceutically acceptable mineral or organic acids.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7117510A FR2137150B1 (en) | 1971-05-14 | 1971-05-14 | |
| FR717117509A FR2137149B1 (en) | 1971-05-14 | 1971-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL39296A0 IL39296A0 (en) | 1972-06-28 |
| IL39296A true IL39296A (en) | 1976-03-31 |
Family
ID=26216390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL39296A IL39296A (en) | 1971-05-14 | 1972-04-25 | 10-(4-(hydroxyalkoxy)piperidinoalkyl)-phenothiazine derivatives and process for preparing them |
Country Status (13)
| Country | Link |
|---|---|
| JP (2) | JPS5118958B1 (en) |
| AU (1) | AU461649B2 (en) |
| BE (1) | BE783411A (en) |
| CH (1) | CH553215A (en) |
| DE (2) | DE2222931C3 (en) |
| DK (1) | DK142318B (en) |
| FI (1) | FI55657C (en) |
| FR (2) | FR2137150B1 (en) |
| GB (2) | GB1383774A (en) |
| IL (1) | IL39296A (en) |
| NL (1) | NL175824C (en) |
| NO (1) | NO135365C (en) |
| SE (2) | SE405973B (en) |
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 |
| US20040072825A1 (en) * | 2000-12-19 | 2004-04-15 | Yves Lamberty | 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 (en) * | 1961-11-25 | 1963-11-29 | Boehringer & Soehne Gmbh | Process for the preparation of novel alkoxy-piperidine derivatives and their salts |
-
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/en not_active IP Right Cessation
- 1972-05-09 FI FI1305/72A patent/FI55657C/en active
- 1972-05-09 SE SE7206146A patent/SE405973B/en unknown
- 1972-05-10 DE DE2222931A patent/DE2222931C3/en not_active Expired
- 1972-05-10 DE DE2264903A patent/DE2264903C3/en not_active Expired
- 1972-05-12 NO NO1690/72A patent/NO135365C/en unknown
- 1972-05-12 BE BE783411A patent/BE783411A/en not_active IP Right Cessation
- 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/en 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
- 1972-05-15 DK DK240672AA patent/DK142318B/en not_active IP Right Cessation
-
1975
- 1975-05-06 SE SE7505250A patent/SE418964B/en unknown
- 1975-11-25 JP JP50140299A patent/JPS5248988B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5118958B1 (en) | 1976-06-14 |
| DE2222931A1 (en) | 1972-11-30 |
| FI55657B (en) | 1979-05-31 |
| JPS5191267A (en) | 1976-08-10 |
| CH553215A (en) | 1974-08-30 |
| AU4222672A (en) | 1973-12-06 |
| DK142318B (en) | 1980-10-13 |
| NO135365B (en) | 1976-12-20 |
| JPS5248988B2 (en) | 1977-12-14 |
| DE2264903A1 (en) | 1975-08-28 |
| FI55657C (en) | 1979-09-10 |
| GB1383774A (en) | 1974-02-12 |
| SE418964B (en) | 1981-07-06 |
| DE2264903B2 (en) | 1981-02-19 |
| AU461649B2 (en) | 1975-06-05 |
| DE2264903C3 (en) | 1981-12-17 |
| SE7505250L (en) | 1975-05-06 |
| DE2222931C3 (en) | 1978-07-06 |
| DK142318C (en) | 1981-03-02 |
| NL175824B (en) | 1984-08-01 |
| GB1383773A (en) | 1974-02-12 |
| SE405973B (en) | 1979-01-15 |
| IL39296A0 (en) | 1972-06-28 |
| FR2137149B1 (en) | 1973-05-11 |
| BE783411A (en) | 1972-11-13 |
| DE2222931B2 (en) | 1977-11-10 |
| NO135365C (en) | 1977-03-30 |
| FR2137150B1 (en) | 1975-01-17 |
| FR2137150A1 (en) | 1972-12-29 |
| FR2137149A1 (en) | 1972-12-29 |
| NL175824C (en) | 1985-01-02 |
| NL7206504A (en) | 1972-11-16 |
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