BE843281A - Nouvelles 10-(omega-(benzoylpiperidino)alkyl) phensothiazines, utiles notamment comme agents tranquillisants, et leur procede de preparation - Google Patents

Nouvelles 10-(omega-(benzoylpiperidino)alkyl) phensothiazines, utiles notamment comme agents tranquillisants, et leur procede de preparation

Info

Publication number: BE843281A
Authority: BE; Belgium
Prior art keywords: emi; general formula; forms; active ingredient; administration
Prior art date: 1975-06-27

Application number

BE168200A

Other languages

English (en)

French (fr)

Priority date (The priority date 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 date listed.)

1975-06-27

Filing date

1976-06-23

Publication date

1976-10-18

1976-06-23 Application filed filed Critical

1976-10-18 Publication of BE843281A publication Critical patent/BE843281A/fr

Links

238000002360 preparation method Methods 0.000 title claims description 8
-1 BENZOYLPIPERIDINO Chemical class 0.000 title description 2
239000003204 tranquilizing agent Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
239000002775 capsule Substances 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229950000688 phenothiazine Drugs 0.000 claims description 4
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229940050411 fumarate Drugs 0.000 claims 1
229910052740 iodine Chemical group 0.000 claims 1
239000002547 new drug Substances 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000002936 tranquilizing effect Effects 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
235000011087 fumaric acid Nutrition 0.000 description 3
239000008188 pellet Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
229960000632 dexamfetamine Drugs 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
230000001665 lethal effect Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JWGBOHJGWOPYCL-UHFFFAOYSA-N 1-(10H-phenothiazin-2-yl)ethanone Chemical compound C1=CC=C2NC3=CC(C(=O)C)=CC=C3SC2=C1 JWGBOHJGWOPYCL-UHFFFAOYSA-N 0.000 description 1
KFZGLJSYQXZIGP-UHFFFAOYSA-N 2-chloro-10h-phenothiazine Chemical compound C1=CC=C2NC3=CC(Cl)=CC=C3SC2=C1 KFZGLJSYQXZIGP-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
QCPLFZQQQQDDEW-UHFFFAOYSA-N [1-(3-chloropropyl)piperidin-4-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCCCl)CC1 QCPLFZQQQQDDEW-UHFFFAOYSA-N 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000000049 anti-anxiety effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 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
238000001819 mass spectrum Methods 0.000 description 1
RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000000047 product Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

BE168200A 1975-06-27 1976-06-23 Nouvelles 10-(omega-(benzoylpiperidino)alkyl) phensothiazines, utiles notamment comme agents tranquillisants, et leur procede de preparation BE843281A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US59121675A	1975-06-27	1975-06-27

Publications (1)

Publication Number	Publication Date
BE843281A true BE843281A (fr)	1976-10-18

Family

ID=24365576

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE168200A BE843281A (fr)	1975-06-27	1976-06-23	Nouvelles 10-(omega-(benzoylpiperidino)alkyl) phensothiazines, utiles notamment comme agents tranquillisants, et leur procede de preparation

Country Status (7)

Country	Link
AU (1)	AU503576B2 (da)
BE (1)	BE843281A (da)
BR (1)	BR7604100A (da)
DK (1)	DK146258C (da)
IE (1)	IE44487B1 (da)
NZ (1)	NZ181291A (da)
ZA (1)	ZA763813B (da)

1976
- 1976-06-15 AU AU14890/76A patent/AU503576B2/en not_active Expired
- 1976-06-18 DK DK274076A patent/DK146258C/da not_active IP Right Cessation
- 1976-06-22 IE IE1357/76A patent/IE44487B1/en not_active IP Right Cessation
- 1976-06-23 BE BE168200A patent/BE843281A/fr not_active IP Right Cessation
- 1976-06-24 BR BR7604100A patent/BR7604100A/pt unknown
- 1976-06-25 ZA ZA763813A patent/ZA763813B/xx unknown
- 1976-06-25 NZ NZ181291A patent/NZ181291A/xx unknown

Also Published As

Publication number	Publication date
DK146258B (da)	1983-08-15
AU503576B2 (en)	1979-09-13
BR7604100A (pt)	1977-07-26
ZA763813B (en)	1977-05-25
DK146258C (da)	1984-01-23
IE44487B1 (en)	1981-12-16
IE44487L (en)	1976-12-27
AU1489076A (en)	1977-12-22
DK274076A (da)	1976-12-28
NZ181291A (en)	1978-06-20

Legal Events

Date

Code

Title

Description

1992-12-31

RE

Patent lapsed

Owner name: A.H. ROBINS CY INC.

Effective date: 19920630

Publication	Publication Date	Title
CH619932A5 (da)	1980-10-31
EP0377528B1 (fr)	1993-12-08	Pipéridines, procédés de préparation et médicaments les contenant
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FR2491467A1 (fr)	1982-04-09	Nouveaux n-alkyl inferieur)-3-phenoxy-1-azetidinecarboxamides possedant notamment une activite sur le systeme nerveux central, et leur procede de preparation
EP0022118A1 (fr)	1981-01-07	Nouveaux dérivés de sulfonyl-aniline, leur procédé de préparation et leur application en thérapeutique
CH631162A5 (fr)	1982-07-30	Derives de la pyrrolidine, leur procede de preparation et leur application en therapeutique.
EP0068998B1 (fr)	1985-08-28	Aryl-1 aminométhyl-2 cyclopropanes carboxylates (Z), leur préparation et leur application en tant que médicaments utiles dans le traitement d'algies diverses
CA1338494C (fr)	1996-07-30	Derives de l'oxime du 1,2,5,6-tetrahydropyridine, leur procede de preparation, leur application comme medicaments et les compositions les renfermant
EP0239461A1 (fr)	1987-09-30	Dérivés de N-¬¬(hydroxy-2 phényl) (phényl) méthylène amino-2 éthyl acétamide, leur préparation et leur application en thérapeutique
CH648827A5 (fr)	1985-04-15	Phenoxyamines heterocycliques substituees, leur preparation et medicaments consistant de ou comprenant ces composes.
FR2461699A1 (fr)	1981-02-06	Nouveaux derives de type methylene-3 azetidine utiles comme medicaments et compositions therapeutiques les contenant
EP0037344B1 (fr)	1984-07-11	Amino-alcoxy pyrazoles, procédé pour leur préparation, et médicaments les contenant
EP0015214A1 (fr)	1980-09-03	Nouveaux dérivés de benzoyl-2 glycylanilides substitués, leur préparation et leur application en tant que médicaments anxiolytiques
CH643243A5 (fr)	1984-05-30	Cis- et trans-3-aryloxy-4-hydroxypyrrolidines et leurs derives, utiles notamment en medecine veterinaire comme antidepresseurs.
EP0308283A1 (fr)	1989-03-22	Dérivés de l'oxime du 1,2,5,6-tétrahydropyridin-3-carboxaldéhyde, leur procédé de préparation, leur application comme médicaments et les compositions les renfermant
EP0301936A1 (fr)	1989-02-01	Dérivés de pipéridine, leur préparation et leur application en thérapeutique
EP0001947B1 (fr)	1981-10-14	Dérivés de l'amino-2 thiazoline, procédé de préparation et compositions pharmaceutiques les contenant
EP0005091B1 (fr)	1981-11-25	Nouvelles pipérazines monosubstituées, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
FR2492821A1 (fr)	1982-04-30	Derives de la pyrimidine, leur procede de preparation et les compositions pharmaceutiques les contenant
EP0078765B1 (fr)	1986-02-26	Dérivés de p-acylaminophénol à effet thérapeutique, procédé pour leur préparation, et composition à effet thérapeutique contenant lesdits dérivés à titre d'ingrédients pharmacologiquement actifs
BE843281A (fr)	1976-10-18	Nouvelles 10-(omega-(benzoylpiperidino)alkyl) phensothiazines, utiles notamment comme agents tranquillisants, et leur procede de preparation
EP0061406B1 (fr)	1984-06-13	Dérivés d'acide benzamido-alkyl-hydroxamique, procédé de préparation et composition thérapeutique
FR2491470A1 (fr)	1982-04-09	Nouvelles cyclopropylmethyl piperazines, leur procede de preparation et leur application en therapeutique
MC2105A1 (fr)	1991-03-11	Derives de tetrahydronaphtalene
CH658786A5 (fr)	1986-12-15	Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters.