CH496716A - Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten - Google Patents

Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten

Info

Publication number: CH496716A
Authority: CH; Switzerland
Prior art keywords: dibenzo; formula; cycloheptene; lower alkyl; acid
Prior art date: 1966-04-22

Application number

CH589866A

Other languages

German (de)

English (en)

Inventor

Hamish Dr Russel Jeff

Original Assignee

Wander Ag Dr A

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.)

1966-04-22

Filing date

1966-04-22

Publication date

1970-09-30

1966-04-22 Application filed by Wander Ag Dr A filed Critical Wander Ag Dr A

1966-04-22 Priority to CH589866A priority Critical patent/CH496716A/de

1967-04-13 Priority to GB1697067A priority patent/GB1146109A/en

1967-04-13 Priority to DE19671720016 priority patent/DE1720016A1/de

1967-04-13 Priority to IL2778567A priority patent/IL27785A/en

1967-04-17 Priority to FR102958A priority patent/FR6143M/fr

1967-04-18 Priority to ES339452A priority patent/ES339452A1/es

1967-04-19 Priority to DK212167A priority patent/DK115116B/da

1967-04-20 Priority to SE559267A priority patent/SE326962B/xx

1967-04-20 Priority to NL6705570A priority patent/NL6705570A/xx

1967-04-21 Priority to AT1035368A priority patent/AT275540B/de

1967-04-21 Priority to AT379967A priority patent/AT275538B/de

1967-04-21 Priority to BE697369D priority patent/BE697369A/xx

1967-04-22 Priority to GR670136289A priority patent/GR36289B/el

1970-09-30 Publication of CH496716A publication Critical patent/CH496716A/de

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
238000000034 method Methods 0.000 claims description 5
239000002841 Lewis acid Substances 0.000 claims description 4
150000007517 lewis acids Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
GSCKMHFCKGEORH-UHFFFAOYSA-N tetracyclo[7.6.1.02,7.010,15]hexadeca-2,4,6,10,12,14-hexaen-8-imine Chemical class C1C2C3=C(C(C1C1=C2C=CC=C1)=N)C=CC=C3 GSCKMHFCKGEORH-UHFFFAOYSA-N 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
-1 amino acetaldehyde diethylacetal oxalate Chemical compound 0.000 abstract description 8
150000001875 compounds Chemical class 0.000 abstract description 5
238000001816 cooling Methods 0.000 abstract description 3
239000003158 myorelaxant agent Substances 0.000 abstract description 3
239000011541 reaction mixture Substances 0.000 abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
230000001773 anti-convulsant effect Effects 0.000 abstract description 2
229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
239000001961 anticonvulsive agent Substances 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract 1
229940035363 muscle relaxants Drugs 0.000 abstract 1
150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
239000001117 sulphuric acid Substances 0.000 abstract 1
235000011149 sulphuric acid Nutrition 0.000 abstract 1
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
GYKZIZUAMKGNCC-UHFFFAOYSA-N N-methyltetracyclo[9.5.0.02,13.05,10]hexadeca-1(16),2(13),5,7,9,14-hexaen-4-imine Chemical compound CN=C1CC2=C3C(C4=C1C=CC=C4)CC2=CC=C3 GYKZIZUAMKGNCC-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
206010058667 Oral toxicity Diseases 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 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
150000001412 amines Chemical class 0.000 description 1
239000002585 base Substances 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
125000004432 carbon atom Chemical group C* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
RZJLDZMIOKCPJA-UHFFFAOYSA-N cycloheptene;hydrochloride Chemical compound Cl.C1CCC=CCC1 RZJLDZMIOKCPJA-UHFFFAOYSA-N 0.000 description 1
150000001933 cycloheptenes Chemical class 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 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
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
231100000418 oral toxicity Toxicity 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH589866A 1966-04-22 1966-04-22 Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten CH496716A (de)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CH589866A CH496716A (de)	1966-04-22	1966-04-22	Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten
GB1697067A GB1146109A (en)	1966-04-22	1967-04-13	5h-dibenzo[a,d]cycloheptene derivatives
DE19671720016 DE1720016A1 (de)	1966-04-22	1967-04-13	5H-Dibenzo[a,d] cyclohepten-Derivate
IL2778567A IL27785A (en)	1966-04-22	1967-04-13	5,11-methylenimino-10,11-dihydro-5h-dibenzo(a,d) cycloheptene derivatives
FR102958A FR6143M (cs)	1966-04-22	1967-04-17
ES339452A ES339452A1 (es)	1966-04-22	1967-04-18	Procedimiento para la preparacion de derivados de 5h-diben-zo (a,d) ciclohepteno.
DK212167A DK115116B (da)	1966-04-22	1967-04-19	Fremgangsmåde til fremstilling af 5H-dibenzo [a,d] cyclohepten-derivater.
SE559267A SE326962B (cs)	1966-04-22	1967-04-20
NL6705570A NL6705570A (cs)	1966-04-22	1967-04-20
AT1035368A AT275540B (de)	1966-04-22	1967-04-21	Verfahren zur Herstellung von neuen 5,11-Methylenimino-10,11-dihydro-5H-dibenzo[a,d]cycloheptenen und ihren Salzen
AT379967A AT275538B (de)	1966-04-22	1967-04-21	Verfahren zur Herstellung von neuen 5,11-Methylenimino-10,11-dihydro-5H-dibenzo[a,d]cycloheptenen und ihren Salzen
BE697369D BE697369A (cs)	1966-04-22	1967-04-21
GR670136289A GR36289B (el)	1966-04-22	1967-04-22	Μεθοδος δια την παρασκευην παραγωγων του 5η-διβενζο (α, d) κυκλοεπτενιου.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH589866A CH496716A (de)	1966-04-22	1966-04-22	Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten

Publications (1)

Publication Number	Publication Date
CH496716A true CH496716A (de)	1970-09-30

Family

ID=4301185

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH589866A CH496716A (de)	1966-04-22	1966-04-22	Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten

Country Status (12)

Country	Link
AT (2)	AT275540B (cs)
BE (1)	BE697369A (cs)
CH (1)	CH496716A (cs)
DE (1)	DE1720016A1 (cs)
DK (1)	DK115116B (cs)
ES (1)	ES339452A1 (cs)
FR (1)	FR6143M (cs)
GB (1)	GB1146109A (cs)
GR (1)	GR36289B (cs)
IL (1)	IL27785A (cs)
NL (1)	NL6705570A (cs)
SE (1)	SE326962B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4950030A (en) *	1986-05-30	1990-08-21	Motor Wheel Corporation	Wheel for a track laying vehicle
US5011834A (en) *	1989-04-14	1991-04-30	State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon	PCP receptor ligands and the use thereof
US6017910A (en) *	1989-04-14	2000-01-25	State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon	PCP receptor ligands and the use thereof

1966
- 1966-04-22 CH CH589866A patent/CH496716A/de not_active IP Right Cessation
1967
- 1967-04-13 DE DE19671720016 patent/DE1720016A1/de active Pending
- 1967-04-13 GB GB1697067A patent/GB1146109A/en not_active Expired
- 1967-04-13 IL IL2778567A patent/IL27785A/en unknown
- 1967-04-17 FR FR102958A patent/FR6143M/fr not_active Expired
- 1967-04-18 ES ES339452A patent/ES339452A1/es not_active Expired
- 1967-04-19 DK DK212167A patent/DK115116B/da unknown
- 1967-04-20 NL NL6705570A patent/NL6705570A/xx unknown
- 1967-04-20 SE SE559267A patent/SE326962B/xx unknown
- 1967-04-21 AT AT1035368A patent/AT275540B/de active
- 1967-04-21 BE BE697369D patent/BE697369A/xx unknown
- 1967-04-21 AT AT379967A patent/AT275538B/de active
- 1967-04-22 GR GR670136289A patent/GR36289B/el unknown

Also Published As

Publication number	Publication date
ES339452A1 (es)	1968-05-16
SE326962B (cs)	1970-08-10
GR36289B (el)	1969-01-20
BE697369A (cs)	1967-10-23
IL27785A (en)	1971-03-24
DE1720016A1 (de)	1971-05-19
AT275538B (de)	1969-10-27
DK115116B (da)	1969-09-08
GB1146109A (en)	1969-03-19
FR6143M (cs)	1968-06-24
AT275540B (de)	1969-10-27
NL6705570A (cs)	1967-10-23

Legal Events

Date	Code	Title	Description
1971-12-31	PL	Patent ceased

Publication	Publication Date	Title
DE2828039A1 (de)	1980-01-10	2-(2-alkoxyethyl)-2'-hydroxy-6,7-benzomorphane deren saeureadditionssalze diese enthaltende arzneimittel und verfahren zu deren herstellung
CH615678A5 (cs)	1980-02-15
DE1795832C3 (de)	1981-07-02	O-Aminoarylketimine und Verfahren zu ihrer Herstellung
DE2237592C2 (de)	1985-08-14	6-(o-Chlorphenyl)-8-chlor-4H-imidazo-[1,2-a] [1,4]-benzodiazepine und Verfahren zu ihrer Herstellung
CH618685A5 (cs)	1980-08-15
CH496716A (de)	1970-09-30	Verfahren zur Herstellung von 5H-Dibenzo(a,d)cyclohepten-Derivaten
AT391866B (de)	1990-12-10	Verfahren zur herstellung neuer s-triazolo (1,5-a) pyrimidine
DE2107356C3 (de)	1978-05-03	Thieno [23-e] - [1,4] diazepin-2-one, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
CH530401A (de)	1972-11-15	Verfahren zur Herstellung von Phenanthridinderivaten
DE2542791C2 (de)	1984-11-08	N,N'-Disubstituierte Naphthylacetamidine
DE1543388B1 (de)	1970-10-01	Basisch substituierte,tricyclische heterocyclische Verbindungen und deren pharmakologisch nicht giftige Salze sowie Verfahren zu ihrer Herstellung
DE3630539A1 (de)	1988-03-10	Derivate von 2,3,4,5,6,7-hexahydro-2,7-methano-1,5-benzoxazonin (bzw. -1,4-benzoxazonin), verfahren zu ihrer herstellung und arzneimittel, die diese verbindung enthalten
DE2311881A1 (de)	1973-09-20	Morphinanderivate
CH513807A (de)	1971-10-15	Verfahren zur Herstellung von tricyclischen Verbindungen
AT131117B (de)	1933-01-10	Verfahren zur Darstellung von Derivaten des 1-Benzyl-6.7-dimethoxy- bzw. -methylendioxyisochinolins.
DE2356830A1 (de)	1974-06-06	1,4,7,10-tetrahydro-4,7-dioxo-12hcyclopentadichinolin-2,9-dicarbonsaeurederivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten
DE2057115A1 (de)	1971-05-27	Verfahren zur Herstellung von in 3 Stellung substituierten 1,2,3,4,5,6 Hexahydro 2,6 methano 3 benzazocin 8 ölen
DE1543388C (de)	1971-05-13	Basisch substituierte tricychsche heterocyclische Verbindungen und deren pharmakologisch nicht giftige Salze sowie Verfahren zu ihrer Herstellung
DE2340122A1 (de)	1974-02-21	Spiranverbindungen mit kondensierten heterozyklen und verfahren zu deren herstellung
CH485654A (de)	1970-02-15	Verfahren zur Herstellung von 10,11-Dihydro-5H-dibenzo(a,d)-cyclohepten-Derivaten
AT313889B (de)	1974-03-11	Verfahren zur Herstellung von neuen 2-(Furyl-methyl)-6,7-benzomorphanderivaten und deren Säureadditionssalzen
AT313890B (de)	1974-03-11	Verfahren zur Herstellung von neuen N-(Furyl-methyl)-morphinanderivaten und deren Säureadditionssalzen
CH631714A5 (en)	1982-08-31	Process for preparing novel quaternary derivatives of sandwicin
AT378191B (de)	1985-06-25	Verfahren zur herstellung neuer pyrogallolaether-derivate
AT273973B (de)	1969-09-10	Verfahren zur Herstellung von neuen Oxazepinen und Thiazepinen und ihrer nichttoxischen Säureadditionssalze