CH514595A - Verfahren zur Herstellung von Verbindungen mit beruhigender Wirkung - Google Patents

Verfahren zur Herstellung von Verbindungen mit beruhigender Wirkung

Info

Publication number: CH514595A
Authority: CH; Switzerland
Prior art keywords: formula; compounds; iii; hal; compound
Prior art date: 1966-10-26

Application number

CH1483167A

Other languages

German (de)

English (en)

Inventor

Gold-Aubert Philippe

Melkonian Diran

Original Assignee

Gold Aubert Philippe

Melkonian Diran

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.)

1966-10-26

Filing date

1967-10-24

Publication date

1971-10-31

1967-10-24 Application filed by Gold Aubert Philippe, Melkonian Diran filed Critical Gold Aubert Philippe

1971-10-31 Publication of CH514595A publication Critical patent/CH514595A/de

Links

239000000932 sedative agent Substances 0.000 title abstract description 6
229940125723 sedative agent Drugs 0.000 title description 4
229940125717 barbiturate Drugs 0.000 title description 2
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 title description 2
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
-1 carbamoyloxy group Chemical group 0.000 claims abstract description 13
229960002695 phenobarbital Drugs 0.000 claims abstract description 12
125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 51
238000000034 method Methods 0.000 claims description 9
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 16
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 abstract description 10
230000001410 anti-tremor Effects 0.000 abstract description 7
FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 abstract description 5
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 abstract description 5
229960004815 meprobamate Drugs 0.000 abstract description 5
230000000147 hypnotic effect Effects 0.000 abstract description 4
229960002319 barbital Drugs 0.000 abstract description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 2
239000000812 cholinergic antagonist Substances 0.000 abstract description 2
230000001624 sedative effect Effects 0.000 abstract description 2
125000003118 aryl group Chemical group 0.000 abstract 1
230000002048 spasmolytic effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
206010044565 Tremor Diseases 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
208000035475 disorder Diseases 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
QIUPXLAJTSVXAY-UHFFFAOYSA-N (1-butoxy-3-chloropropan-2-yl) carbamate Chemical compound CCCCOCC(CCl)OC(N)=O QIUPXLAJTSVXAY-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
230000001914 calming effect Effects 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000003340 mental effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229960001301 amobarbital Drugs 0.000 description 2
VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical compound CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 2
230000002921 anti-spasmodic effect Effects 0.000 description 2
230000002996 emotional effect Effects 0.000 description 2
230000001788 irregular Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
230000035939 shock Effects 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
230000002936 tranquilizing effect Effects 0.000 description 2
238000005406 washing Methods 0.000 description 2
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
206010012335 Dependence Diseases 0.000 description 1
208000027534 Emotional disease Diseases 0.000 description 1
206010028347 Muscle twitching Diseases 0.000 description 1
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
206010034719 Personality change Diseases 0.000 description 1
208000029808 Psychomotor disease Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
241001279009 Strychnos toxifera Species 0.000 description 1
206010043268 Tension Diseases 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
150000001557 benzodiazepines Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
206010016256 fatigue Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000035987 intoxication Effects 0.000 description 1
231100000566 intoxication Toxicity 0.000 description 1
238000011835 investigation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WRLGYAWRGXKSKG-UHFFFAOYSA-M phenobarbital sodium Chemical compound [Na+].C=1C=CC=CC=1C1(CC)C(=O)NC([O-])=NC1=O WRLGYAWRGXKSKG-UHFFFAOYSA-M 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
208000019899 phobic disease Diseases 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
XGUUCCVRACSUAD-UHFFFAOYSA-M sodium;5,5-bis(prop-2-enyl)pyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].C=CCC1(CC=C)C(=O)NC(=O)[N-]C1=O XGUUCCVRACSUAD-UHFFFAOYSA-M 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002557 soporific effect Effects 0.000 description 1
229960005453 strychnine Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001457 vasomotor Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1483167A 1966-10-26 1967-10-24 Verfahren zur Herstellung von Verbindungen mit beruhigender Wirkung CH514595A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB4812066A GB1193438A (en)	1966-10-26	1966-10-26	Barbituric Acid Derivatives, preparation thereof and Pharmaceutical Compositions containing them

Publications (1)

Publication Number	Publication Date
CH514595A true CH514595A (de)	1971-10-31

Family

ID=10447466

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1483167A CH514595A (de)	1966-10-26	1967-10-24	Verfahren zur Herstellung von Verbindungen mit beruhigender Wirkung

Country Status (8)

Country	Link
AT (1)	AT299238B (fr)
BE (1)	BE705672A (fr)
CH (1)	CH514595A (fr)
DE (1)	DE1695043C2 (fr)
ES (1)	ES346424A1 (fr)
FR (2)	FR1549453A (fr)
GB (1)	GB1193438A (fr)
NL (1)	NL6714587A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1581834A (en) *	1976-11-01	1980-12-31	Sapos Sa	Complexes of barbituric acid derivatives
GB8309813D0 (en) *	1983-04-12	1983-05-18	Sapos Sa	Pyrimidinetrione derivatives

1966
- 1966-10-26 GB GB4812066A patent/GB1193438A/en not_active Expired
1967
- 1967-10-20 FR FR1549453D patent/FR1549453A/fr not_active Expired
- 1967-10-24 CH CH1483167A patent/CH514595A/de not_active IP Right Cessation
- 1967-10-25 ES ES346424A patent/ES346424A1/es not_active Expired
- 1967-10-26 NL NL6714587A patent/NL6714587A/xx unknown
- 1967-10-26 BE BE705672D patent/BE705672A/xx not_active IP Right Cessation
- 1967-10-26 DE DE19671695043 patent/DE1695043C2/de not_active Expired
- 1967-10-27 AT AT973067A patent/AT299238B/de not_active IP Right Cessation
1968
- 1968-01-26 FR FR137521A patent/FR8022M/fr not_active Expired

Also Published As

Publication number	Publication date
GB1193438A (en)	1970-06-03
ES346424A1 (es)	1969-04-16
FR8022M (fr)	1970-08-03
BE705672A (fr)	1968-04-26
DE1695043C2 (de)	1983-02-17
DE1695043A1 (de)	1972-04-27
NL6714587A (fr)	1968-04-29
AT299238B (de)	1972-06-12
FR1549453A (fr)	1968-12-13

Legal Events

Date	Code	Title	Description
1987-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE3016752A1 (de)	1980-12-04	Verfahren zur herstellung von 2-isopropylaminopyrimidinhydroxy-derivaten
DE2726820A1 (de)	1977-12-22	Imidazothiazine
DE2458638C2 (de)	1984-05-10	4'-substituierte 2-Methyl-3-piperidinopropiophenonderivate, Verfahren zu deren Herstellung und pharmakologische Zubereitungen, welche diese enthalten
CH514595A (de)	1971-10-31	Verfahren zur Herstellung von Verbindungen mit beruhigender Wirkung
DE1958515C3 (fr)	1977-02-10
DE2738498C3 (de)	1980-02-21	H2-Chloräthyl)-l-nitroso-3-(2-acetamido-2desoxy- ß -D-glucopyranosyl)- harnstoffe, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE1545555C3 (fr)	1976-03-18
DE2711149C3 (de)	1980-12-11	N-Substituierte[4-Chlor-6-(23-xylidino)-2· pyrimidinyl- thio] essigsäureamide sowie Verfahren zu deren Herstellung
DE2609574C3 (de)	1978-06-22	1 -^-Fluor-S-trifluormethylthiophenyD-piperazin, dessen Salze, Verfahren zu dessen Herstellung und Arzneimittel
EP0240854A1 (fr)	1987-10-14	Dérivés de 1,3,5-triazine substitués avec des groupes bis-tertiobutyles, procédé pour leur préparation, médicaments contenant ces composés et leur application
DE2536170C3 (de)	1980-10-23	Flavonderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2748794C2 (de)	1993-10-21	Malonylharnstoffkomplexe, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
DE2614946C2 (de)	1987-04-23	Neue Nucleosidderivate
DE1912941B2 (de)	1979-10-18	1 -PhenyM-amino-e-methoxypridaziniumsalze
DE1518311B1 (de)	1972-05-31	N-(2-Diaethylaminoaethyl)-2-methoxy-3,4- bzw. 4,5-methylendioxybenzamid und deren pharmakologisch nicht giftige Saeureadditionssalze
DE2230003A1 (de)	1973-01-18	Neue nitrosoharnstoffderivate
DE2265139C3 (de)	1978-07-13	Substituierte l-Methyl-5-phenyl-13-Dihydro-2H-1,4-benzodiazepin-2-on-derivate
CH658653A5 (de)	1986-11-28	Verfahren zur herstellung von pyrimidintrionderivaten.
DD256695A5 (de)	1988-05-18	Verfahren zur herstellung von einem optisch aktiven 2-chlor-12-3/3-dimethylamine-2-methylpropyl/-12h-di-benzo(d,g)(1,3,6)dixazocin
DE2435222C2 (de)	1985-08-22	Verfahren zur Herstellung von N-(2-Diethylamino)-ethyl-2-methoxy-5-methylsulfonylbenzamid
DE948153C (de)	1956-08-30	Verfahren zur Herstellung des hoeherschmelzenden Isomeren des 2-AEthylcrotonylharnstoffes
DE1470415C (de)	1972-08-10	2-Thio-5 -phenyl-1,2-dihydro-3 H-1,4benzodiazepinderivate
DE1545555B2 (de)	1975-08-07	Verfahren zur Herstellung von 1,3-Dihydro-S-amino^H-M-benzodiazepin-2-onen
DE2422430C3 (de)	1979-05-31	Derivate der Secalonsäure D, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Bekämpfung von Tumoren
EP0060994A1 (fr)	1982-09-29	Dérivé de bis-hydroxyéthylmercapto-1,10-décane, un procédé pour sa préparation, ainsi que les compositions pharmaceutiques le contenant