CH400108A - Verfahren zur Herstellung von 5-Oxydibenzocycloheptanderivaten - Google Patents

Verfahren zur Herstellung von 5-Oxydibenzocycloheptanderivaten

Info

Publication number: CH400108A
Authority: CH; Switzerland
Prior art keywords: derivatives; melting point; preparation; oxydibenzocycloheptane; dibenzo
Prior art date: 1959-04-01

Application number

CH351160A

Other languages

German (de)

English (en)

Inventor

Franciscus Dr Harms August

Original Assignee

Koninklijke Pharma Fab Nv

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.)

1959-04-01

Filing date

1960-03-29

Publication date

1965-10-15

1960-03-29 Application filed by Koninklijke Pharma Fab Nv filed Critical Koninklijke Pharma Fab Nv

1965-10-15 Publication of CH400108A publication Critical patent/CH400108A/de

Links

238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 6
238000006798 ring closing metathesis reaction Methods 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229920000137 polyphosphoric acid Polymers 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 5
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
238000009835 boiling Methods 0.000 description 2
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910001023 sodium amalgam Inorganic materials 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
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
150000005481 1,2-diphenylethanes Chemical class 0.000 description 1
BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical class C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 1
HMFNAOVIFKUVFI-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)ethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=C(Cl)C=C1 HMFNAOVIFKUVFI-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
101150036449 SIRPA gene Proteins 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
230000001004 anti-acetylcholinic effect Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/33—Polycyclic acids
- C07C63/331—Polycyclic acids with all carboxyl groups bound to non-condensed rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH351160A 1959-04-01 1960-03-29 Verfahren zur Herstellung von 5-Oxydibenzocycloheptanderivaten CH400108A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL237663		1959-04-01
US277013A US3209007A (en)	1959-04-01	1963-04-30	(dibenzo (a, d) 1, 4-cycloheptene-5-yloxy) amines

Publications (1)

Publication Number	Publication Date
CH400108A true CH400108A (de)	1965-10-15

Family

ID=31497751

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH351160A CH400108A (de)	1959-04-01	1960-03-29	Verfahren zur Herstellung von 5-Oxydibenzocycloheptanderivaten
CH78965A CH410931A (de)	1959-04-01	1960-03-29	Verfahren zur Herstellung von 5-Oxy-dibenzocycloheptenderivaten

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH78965A CH410931A (de)	1959-04-01	1960-03-29	Verfahren zur Herstellung von 5-Oxy-dibenzocycloheptenderivaten

Country Status (6)

Country	Link
US (1)	US3209007A (da)
CH (2)	CH400108A (da)
DE (1)	DE1470127A1 (da)
DK (1)	DK106732C (da)
FR (1)	FR3745M (da)
GB (1)	GB943604A (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1091910A (en) *	1964-08-18	1967-11-22	Koninklijke Pharma Fab Nv	New dibenzocycloheptenylamines
US4569944A (en) *	1984-06-21	1986-02-11	Warner-Lambert Company	Dibenzosuberone as a non-steroidal anti-inflammatory compound and compositions thereof

1960
- 1960-03-29 CH CH351160A patent/CH400108A/de unknown
- 1960-03-29 CH CH78965A patent/CH410931A/de unknown
- 1960-04-01 GB GB11550/60A patent/GB943604A/en not_active Expired
1963
- 1963-04-30 US US277013A patent/US3209007A/en not_active Expired - Lifetime
- 1963-10-09 DK DK474263AA patent/DK106732C/da active
- 1963-10-18 DE DE19631470127 patent/DE1470127A1/de active Pending
- 1963-11-12 FR FR953340A patent/FR3745M/fr active Active

Also Published As

Publication number	Publication date
DE1470127A1 (de)	1969-05-08
GB943604A (en)	1963-12-04
FR3745M (fr)	1965-12-13
US3209007A (en)	1965-09-28
CH410931A (de)	1966-04-15
DK106732C (da)	1967-03-13

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DE2624557A1 (de)	1976-12-23	Verfahren zur aroylierung von 1-alkylpyrrol-2-essigsaeure-derivaten in abwesenheit von katalysatoren
DE1933985A1 (de)	1970-01-15	Neue Cycloalkancarbonsaeurederivate und Verfahren zu ihrer Herstellung
DE2023000A1 (de)	1971-08-05	Neue cyclische Carbonsaeurederivate und Verfahren zu ihrer Herstellung
AT222637B (de)	1962-08-10	Verfahren zur Herstellung von neuen Dibenzocycloheptanderivaten
CH410931A (de)	1966-04-15	Verfahren zur Herstellung von 5-Oxy-dibenzocycloheptenderivaten
CH532005A (de)	1972-12-31	Verfahren zur Herstellung von Phenoxy-alkan-carbonsäuren
DE913178C (de)	1954-06-10	Verfahren zur Herstellung therapeutisch wirksamer basischer Ester
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AT256844B (de)	1967-09-11	Verfahren zur Herstellung von neuen 6,11-Dihydrodibenzo-[b,e]-thiepinen
AT228217B (de)	1963-07-10	Verfahren zur Herstellung von neuen Homothioxanthen-Derivaten
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AT228804B (de)	1963-08-12	Verfahren zur Herstellung von Thionothiolphosphorsäureestern
AT244327B (de)	1965-12-27	Verfahren zur Herstellung von Diphenylalkylaminen und ihren physiologisch verträglichen Salzen
AT247847B (de)	1966-06-27	Verfahren zur Herstellung von neuen 5-(3'-Aminopropyliden)-5H-dibenzo [a, d] cycloheptenen bzw. den 10, 11-Dihydroderivaten derselben
AT263026B (de)	1968-07-10	Verfahren zur Herstellung von neuen Phenthiazinderivaten
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DE1620536C (de)	1972-01-05	Verfahren zur Herstellung von alpha Pyrrolidinoketonen und ihren Salzen
CH456578A (de)	1968-07-31	Verfahren zur Herstellung von 5H-Dibenzo(a,d)cycloheptenen
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