CH544768A - Verfahren zur Herstellung neuer Dibenzoxazepine - Google Patents

Verfahren zur Herstellung neuer Dibenzoxazepine

Info

Publication number: CH544768A
Authority: CH; Switzerland
Prior art keywords: formula; compounds; trifluoromethylsulfonyl; oxazepine; dibenz
Prior art date: 1970-08-06

Application number

CH1541672A

Other languages

German (de)

English (en)

Inventor

Schmutz Jean

Hunziker Fritz

Martin Kuenzle Franz

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.)

1970-08-06

Filing date

1970-08-06

Publication date

1973-11-30

1970-08-06 Application filed by Wander Ag Dr A filed Critical Wander Ag Dr A

1970-08-06 Priority to CH1541672A priority Critical patent/CH544768A/de

1973-01-23 Priority to US326121A priority patent/US3891647A/en

1973-11-30 Publication of CH544768A publication Critical patent/CH544768A/de

Links

239000003176 neuroleptic agent Substances 0.000 title description 2
230000000701 neuroleptic effect Effects 0.000 title description 2
239000002111 antiemetic agent Substances 0.000 title 1
229940125683 antiemetic agent Drugs 0.000 title 1
150000000221 oxazepines Chemical class 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 10
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 2
WXLCDTBTIVJDCE-UHFFFAOYSA-N 1,4-oxazepine Chemical compound O1C=CC=NC=C1 WXLCDTBTIVJDCE-UHFFFAOYSA-N 0.000 abstract description 7
YERNAAQLMAFCGK-UHFFFAOYSA-N 1-benzo[d][1]benzoxepin-1-ylpiperazine Chemical compound N1(CCNCC1)C1=CC=CC2=C1C1=C(C=CO2)C=CC=C1 YERNAAQLMAFCGK-UHFFFAOYSA-N 0.000 abstract 1
125000004185 ester group Chemical group 0.000 abstract 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000155 melt Substances 0.000 description 11
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
238000009835 boiling Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
-1 methyl mercapto group Chemical group 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 2
GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 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
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 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
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000003474 anti-emetic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004659 aryl alkyl thio group Chemical group 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
NPUACKRELIJTFM-UHFFFAOYSA-N cr gas Chemical compound C1=NC2=CC=CC=C2OC2=CC=CC=C21 NPUACKRELIJTFM-UHFFFAOYSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
235000003441 saturated fatty acids Nutrition 0.000 description 1
150000004671 saturated fatty acids Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
239000008030 superplasticizer Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003571 thiolactams Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
- C07C265/12—Derivatives of isocyanic acid having isocyanate groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/20—[b, f]-condensed

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CH1541672A 1970-08-06 1970-08-06 Verfahren zur Herstellung neuer Dibenzoxazepine CH544768A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH1541672A CH544768A (de)	1970-08-06	1970-08-06	Verfahren zur Herstellung neuer Dibenzoxazepine
US326121A US3891647A (en)	1970-08-06	1973-01-23	2-trifluoromethyl-sulphonyl-11-substituted-piperazinyl-dibenz {8 b,f{9 {8 1,4{9 {0 oxazepine

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1192270A CH549593A (de)	1970-08-06	1970-08-06	Verfahren zur herstellung neuer dibenzoxazepine.
CH1541672A CH544768A (de)	1970-08-06	1970-08-06	Verfahren zur Herstellung neuer Dibenzoxazepine

Publications (1)

Publication Number	Publication Date
CH544768A true CH544768A (de)	1973-11-30

Family

ID=4378194

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH1541672A CH544768A (de)	1970-08-06	1970-08-06	Verfahren zur Herstellung neuer Dibenzoxazepine
CH1192270A CH549593A (de)	1970-08-06	1970-08-06	Verfahren zur herstellung neuer dibenzoxazepine.
CH1541572A CH544767A (de)	1970-08-06	1970-08-06	Verfahren zur Herstellung neuer Dibenzoxazepine

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1192270A CH549593A (de)	1970-08-06	1970-08-06	Verfahren zur herstellung neuer dibenzoxazepine.
CH1541572A CH544767A (de)	1970-08-06	1970-08-06	Verfahren zur Herstellung neuer Dibenzoxazepine

Country Status (5)

Country	Link
AT (1)	AT325619B (pl)
CH (3)	CH544768A (pl)
PL (1)	PL82244B1 (pl)
SU (3)	SU450411A3 (pl)
ZA (1)	ZA715245B (pl)

1970
- 1970-08-06 CH CH1541672A patent/CH544768A/de not_active IP Right Cessation
- 1970-08-06 CH CH1192270A patent/CH549593A/de not_active IP Right Cessation
- 1970-08-06 CH CH1541572A patent/CH544767A/de not_active IP Right Cessation
1971
- 1971-08-04 SU SU1850487A patent/SU450411A3/ru active
- 1971-08-04 PL PL1971149831A patent/PL82244B1/pl unknown
- 1971-08-04 SU SU1690481A patent/SU461501A3/ru active
- 1971-08-04 SU SU1850485A patent/SU451246A3/ru active
- 1971-08-05 AT AT687071A patent/AT325619B/de not_active IP Right Cessation
- 1971-08-06 ZA ZA715245A patent/ZA715245B/xx unknown

Also Published As

Publication number	Publication date
CH549593A (de)	1974-05-31
SU450411A3 (ru)	1974-11-15
ATA687071A (de)	1975-01-15
SU451246A3 (ru)	1974-11-25
SU461501A3 (ru)	1975-02-25
PL82244B1 (en)	1975-10-31
CH544767A (de)	1974-01-15
ZA715245B (en)	1973-03-28
AT325619B (de)	1975-10-27

Legal Events

Date	Code	Title	Description
1977-03-15	PL	Patent ceased

Publication	Publication Date	Title
CH544768A (de)	1973-11-30	Verfahren zur Herstellung neuer Dibenzoxazepine
DE2929414A1 (de)	1981-02-05	Pyrimido- eckige klammer auf 5',4' zu 5,6 eckige klammer zu -pyrido- eckige klammer auf 1,2-a eckige klammer zu -benzimidazole, verfahren zu ihrer herstellung und deren verwendung
AT202152B (de)	1959-02-10	Verfahren zur Herstellung von neuen Dimethylaminopropylidenthiaxanthenen.
DE1695941A1 (de)	1971-05-13	Verfahren zur Herstellung von 5-gliedrigen N-Heterocyclen,die im Ring ungesaettigt sind
AT338798B (de)	1977-09-12	Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen, deren optischen isomeren und deren salzen
DE2139016A1 (de)	1972-02-10	Neue organische Verbindungen und Verfahren zu deren Herstellung
DE1804328A1 (de)	1969-05-22	3-substituierte Chinoxalinone und Verfahren zur Herstellung von 3-substituierten Chinoxalin-2-Onen
CH644602A5 (de)	1984-08-15	Benzothiazocin- und benzothiazoninderivate, ihre herstellung und diese derivate enthaltende pharmazeutische praeparate.
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