CH367831A - Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten - Google Patents

Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten

Info

Publication number: CH367831A
Authority: CH; Switzerland
Prior art keywords: formula; methyl; parts; acid; piperidyl
Prior art date: 1958-07-23

Application number

CH6210558A

Other languages

German (de)

English (en)

Inventor

Louis Dr Mueslin

Walter Dr Schindler

Franz Dr Haefliger

Original Assignee

Geigy Ag J R

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.)

1958-07-23

Filing date

1958-07-23

Publication date

1963-03-15

1958-07-23 Application filed by Geigy Ag J R filed Critical Geigy Ag J R

1958-07-23 Priority to CH6210558A priority Critical patent/CH367831A/de

1959-07-22 Priority to ES0250986A priority patent/ES250986A1/es

1959-07-22 Priority to ES0250985A priority patent/ES250985A1/es

1963-03-15 Publication of CH367831A publication Critical patent/CH367831A/de

Links

238000000034 method Methods 0.000 title claims description 7
150000001538 azepines Chemical class 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title description 2
239000002253 acid Substances 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical class C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 description 4
ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical class C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NISITZDNUGPQFO-UHFFFAOYSA-N 3-chloro-1-methylpiperidine Chemical compound CN1CCCC(Cl)C1 NISITZDNUGPQFO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
-1 N-substituted azepine Chemical class 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000006286 aqueous extract Substances 0.000 description 2
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229960003750 ethyl chloride Drugs 0.000 description 2
229940050176 methyl chloride Drugs 0.000 description 2
229940078552 o-xylene Drugs 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
XMVGLLJLAIYTFJ-UHFFFAOYSA-N 2-ethyl-6-(2-phenylethenyl)cyclohexa-2,4-dien-1-imine Chemical compound C(C)C=1C(C(C=CC1)C=CC1=CC=CC=C1)=N XMVGLLJLAIYTFJ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000002005 ganglioplegic effect Effects 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 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
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000203 mixture Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

CH6210558A 1958-07-23 1958-07-23 Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten CH367831A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH6210558A CH367831A (de)	1958-07-23	1958-07-23	Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten
ES0250986A ES250986A1 (es)	1958-07-23	1959-07-22	Procedimiento para la preparaciën de nuevos deribados de la azepina, basicamente sustituidos
ES0250985A ES250985A1 (es)	1958-07-23	1959-07-22	Procedimiento para la preparaciën de nuevos derivados de la azepina, basicamente sustituidos

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH6210558A CH367831A (de)	1958-07-23	1958-07-23	Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten

Publications (1)

Publication Number	Publication Date
CH367831A true CH367831A (de)	1963-03-15

Family

ID=4524088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6210558A CH367831A (de)	1958-07-23	1958-07-23	Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten

Country Status (2)

Country	Link
CH (1)	CH367831A (es)
ES (2)	ES250986A1 (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2052991A1 (en) *	1969-06-20	1971-04-16	Sogeras	N-(dibenzo (bf) azepines quinuclidines

1958
- 1958-07-23 CH CH6210558A patent/CH367831A/de unknown
1959
- 1959-07-22 ES ES0250986A patent/ES250986A1/es not_active Expired
- 1959-07-22 ES ES0250985A patent/ES250985A1/es not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2052991A1 (en) *	1969-06-20	1971-04-16	Sogeras	N-(dibenzo (bf) azepines quinuclidines

Also Published As

Publication number	Publication date
ES250986A1 (es)	1960-01-16
ES250985A1 (es)	1960-01-16

Publication	Publication Date	Title
DE2803651C2 (es)	1988-10-20
DE2851028A1 (de)	1979-05-31	Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung
DE949105C (de)	1956-09-13	Verfahren zur Herstellung von neuen, fungiciden und protozoociden aromatischen Aminoketonen und deren Salzen
DE934651C (de)	1955-11-03	Verfahren zur Herstellung von tetrasubstituierten Diaminoalkanen
CH367831A (de)	1963-03-15	Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten
CH438352A (de)	1967-06-30	Verfahren zur Herstellung von Diphenylalkylaminen
DE68912887T2 (de)	1994-05-26	Thiophen-2-carboxamid-Derivate und ihre Verwendung als pharmazeutische Mittel.
DE1620128A1 (de)	1970-03-12	Verfahren zur Herstellung von neuen organischen Amiden
AT236389B (de)	1964-10-26	Verfahren zur Herstellung von neuen N-substituierten heterocyclischen Verbindungen
AT217045B (de)	1961-09-11	Verfahren zur Herstellung von neuen monoalkylierten bzw. monohalogenierten N-Derivaten von 10,11-Dihydro-5H-dibenzo[b,f]azepinen und 5H-Dibenzo[b,f]azepinen
AT220623B (de)	1962-04-10	Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen
AT212326B (de)	1960-12-12	Verfahren zur Herstellung von neuen, basisch substituierten Azepinderivaten
AT222130B (de)	1962-07-10	Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen
AT204041B (de)	1959-06-25	Verfahren zur Herstellung von neuen Phenthiazinderivaten
AT233579B (de)	1964-05-11	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT233581B (de)	1964-05-11	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT233019B (de)	1964-04-25	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT228218B (de)	1963-07-10	Verfahren zur Herstellung von neuen Thioxanthen-Verbindungen
AT201603B (de)	1959-01-10	Verfahren zur Herstellung der neuer Piperazo[c]pyridazin-Verbindungen
AT219613B (de)	1962-02-12	Verfahren zur Herstellung von neuen N-heterocyclischen Verbindungen und deren Salzen
AT360991B (de)	1981-02-10	Verfahren zur herstellung neuer 1-alkyl-4- phenylpiperidinderivate und von deren salzen und optisch aktiven verbindungen
AT219036B (de)	1962-01-10	Verfahren zur Herstellung von neuen 3-substituierten 1-Benzylindanen und deren Salzen
AT225712B (de)	1963-02-11	Verfahren zur Herstellung einer neuen N-heterocyclischen Verbindung
AT233014B (de)	1964-04-25	Verfahren zur Herstellung von neuen Iminodibenzylderivaten
AT208869B (de)	1960-05-10	Verfahren zur Herstellung von neuen N-substituierten Azepinen

CH367831A - Verfahren zur Herstellung von neuen basisch substituierten Azepinderivaten - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (3)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4524088

Family Applications (1)

Country Status (2)

Cited By (1)

Cited By (1)

Also Published As

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