CH389614A - Verfahren zur Herstellung von basischen 1,3-disubstituierten Phenothiazinderivaten - Google Patents

Verfahren zur Herstellung von basischen 1,3-disubstituierten Phenothiazinderivaten

Info

Publication number: CH389614A
Authority: CH; Switzerland
Prior art keywords: basic; disubstituted; carbon atoms; phenothiazine; preparation
Prior art date: 1958-09-03

Application number

CH7757259A

Other languages

German (de)

English (en)

Inventor

Jaromir Dr Hebky

Jiri D N Dr Kejha

Original Assignee

Spofa Vereinigte Pharma Werke

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.)

1958-09-03

Filing date

1959-08-31

Publication date

1965-03-31

1959-08-31 Application filed by Spofa Vereinigte Pharma Werke filed Critical Spofa Vereinigte Pharma Werke

1965-03-31 Publication of CH389614A publication Critical patent/CH389614A/de

Links

-1 1,3-disubstituted phenothiazine Chemical class 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 5
229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 title claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 6
238000006114 decarboxylation reaction Methods 0.000 claims description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
125000006267 biphenyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 3
238000001816 cooling Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000007858 starting material Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
YCODCVPEBGVEAV-UHFFFAOYSA-N 1,3-dichloro-10H-phenothiazine Chemical compound ClC1=CC(=CC=2SC3=CC=CC=C3NC1=2)Cl YCODCVPEBGVEAV-UHFFFAOYSA-N 0.000 description 1
PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-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
239000002253 acid Substances 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
MJRIZSDRKPPHTK-UHFFFAOYSA-N phenothiazine-10-carbonyl chloride Chemical compound C1=CC=C2N(C(=O)Cl)C3=CC=CC=C3SC2=C1 MJRIZSDRKPPHTK-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Landscapes

Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

CH7757259A 1958-09-03 1959-08-31 Verfahren zur Herstellung von basischen 1,3-disubstituierten Phenothiazinderivaten CH389614A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CS450858		1958-09-03

Publications (1)

Publication Number	Publication Date
CH389614A true CH389614A (de)	1965-03-31

Family

ID=5387972

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7757259A CH389614A (de)	1958-09-03	1959-08-31	Verfahren zur Herstellung von basischen 1,3-disubstituierten Phenothiazinderivaten

Country Status (2)

Country	Link
BE (1)	BE582133A (fr)
CH (1)	CH389614A (fr)

1959
- 1959-08-28 BE BE582133A patent/BE582133A/fr unknown
- 1959-08-31 CH CH7757259A patent/CH389614A/de unknown

Also Published As

Publication number	Publication date
BE582133A (fr)	1960-12-16

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