AT276398B - Verfahren zur Herstellung neuer 11-aminoalkylierter Dibenz[b,f]1,4-oxazepine und Dibenzo[b,f]1,4-thiazepine sowie von Säure-Additionssalzen davon - Google Patents
Verfahren zur Herstellung neuer 11-aminoalkylierter Dibenz[b,f]1,4-oxazepine und Dibenzo[b,f]1,4-thiazepine sowie von Säure-Additionssalzen davonInfo
- Publication number
- AT276398B AT276398B AT1188866A AT1188866A AT276398B AT 276398 B AT276398 B AT 276398B AT 1188866 A AT1188866 A AT 1188866A AT 1188866 A AT1188866 A AT 1188866A AT 276398 B AT276398 B AT 276398B
- Authority
- AT
- Austria
- Prior art keywords
- dibenz
- acid addition
- addition salts
- dibenzo
- oxazepines
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 10
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims 3
- 150000000225 1,4-oxazepines Chemical class 0.000 title claims 2
- 150000004915 1,4-thiazepines Chemical class 0.000 title claims 2
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 5
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- DGBISJKLNVVJGD-UHFFFAOYSA-N 2-phenylsulfanylaniline Chemical compound NC1=CC=CC=C1SC1=CC=CC=C1 DGBISJKLNVVJGD-UHFFFAOYSA-N 0.000 description 1
- VXTWGQJBNZIMFQ-UHFFFAOYSA-N 7-propylbenzo[b][1,4]benzothiazepine Chemical compound C(CC)C1=CC=CC2=C1C=NC1=C(S2)C=CC=C1 VXTWGQJBNZIMFQ-UHFFFAOYSA-N 0.000 description 1
- MHANMQJBLDJXPE-UHFFFAOYSA-N CN(C)CC1=NC2=C(OC3=C1C=CC=C3)C=CC=C2 Chemical compound CN(C)CC1=NC2=C(OC3=C1C=CC=C3)C=CC=C2 MHANMQJBLDJXPE-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- -1 dimethylene group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000003438 effect on compound Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/12—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
- C07D281/16—[b, f]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1817465A CH473141A (de) | 1965-12-30 | 1965-12-30 | Verfahren zur Herstellung 11-aminoalkylierter Dibenz(b,f)-1,4-oxazepine und Dibenzo(b,f)-1,4-thiazepine |
| CH446466 | 1966-03-28 | ||
| CH1103366 | 1966-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT276398B true AT276398B (de) | 1969-11-25 |
Family
ID=27174855
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT1188866A AT276398B (de) | 1965-12-30 | 1966-12-27 | Verfahren zur Herstellung neuer 11-aminoalkylierter Dibenz[b,f]1,4-oxazepine und Dibenzo[b,f]1,4-thiazepine sowie von Säure-Additionssalzen davon |
| AT02082/68A AT278817B (de) | 1965-12-30 | 1966-12-27 | Verfahren zur herstellung neuer 11-aminoalkylierter dibenz <b,f>-1,4-oxazepine und dibenzo <b,f>-1,4-thiazepine sowie von saeure-additionssalzen davon |
| AT02080/68A AT278815B (de) | 1965-12-30 | 1966-12-27 | Verfahren zur herstellung neuer 11-aminoalkylierter dibenz <b,f>-1,4-oxazepine und dibenzo <b,f>-1,4-thiazepine sowi |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT02082/68A AT278817B (de) | 1965-12-30 | 1966-12-27 | Verfahren zur herstellung neuer 11-aminoalkylierter dibenz <b,f>-1,4-oxazepine und dibenzo <b,f>-1,4-thiazepine sowie von saeure-additionssalzen davon |
| AT02080/68A AT278815B (de) | 1965-12-30 | 1966-12-27 | Verfahren zur herstellung neuer 11-aminoalkylierter dibenz <b,f>-1,4-oxazepine und dibenzo <b,f>-1,4-thiazepine sowi |
Country Status (2)
| Country | Link |
|---|---|
| AT (3) | AT276398B (h) |
| SE (1) | SE356053B (h) |
-
1966
- 1966-12-27 AT AT1188866A patent/AT276398B/de active
- 1966-12-27 AT AT02082/68A patent/AT278817B/de not_active IP Right Cessation
- 1966-12-27 AT AT02080/68A patent/AT278815B/de not_active IP Right Cessation
- 1966-12-28 SE SE17812/66A patent/SE356053B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT278815B (de) | 1970-02-10 |
| AT278817B (de) | 1970-02-10 |
| SE356053B (h) | 1973-05-14 |
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