CH488691A - Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden - Google Patents

Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden

Info

Publication number: CH488691A
Authority: CH; Switzerland
Prior art keywords: butoxy; sep; dimethyl; ring; methyl
Prior art date: 1967-10-20

Application number

CH101570A

Other languages

German (de)

English (en)

Inventor

Suter Dr Doerflingen Hans

Hans Dipl Chem Zutter

Original Assignee

Eprova Ag

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.)

1967-10-20

Filing date

1967-10-20

Publication date

1970-04-15

1967-10-20 Application filed by Eprova Ag filed Critical Eprova Ag

1967-10-20 Priority to CH101570A priority Critical patent/CH488691A/de

1970-04-15 Publication of CH488691A publication Critical patent/CH488691A/de

Links

238000000034 method Methods 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title description 3
FXNZTUWKJTTZOQ-UHFFFAOYSA-N 4-butoxy-2,3-dimethylbenzamide Chemical class C(CCC)OC1=C(C(=C(C(=O)N)C=C1)C)C FXNZTUWKJTTZOQ-UHFFFAOYSA-N 0.000 title description 2
239000000126 substance Substances 0.000 claims description 14
238000005984 hydrogenation reaction Methods 0.000 claims description 10
-1 4-butoxy-2,6-dimethyl-benzoic acid amides Chemical class 0.000 claims description 9
238000007069 methylation reaction Methods 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
FIZUEJGPZMWHHS-UHFFFAOYSA-N 4-butoxy-2,6-dimethylbenzoic acid Chemical compound CCCCOC1=CC(C)=C(C(O)=O)C(C)=C1 FIZUEJGPZMWHHS-UHFFFAOYSA-N 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
206010002091 Anaesthesia Diseases 0.000 description 9
230000037005 anaesthesia Effects 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000008595 infiltration Effects 0.000 description 4
238000001764 infiltration Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003589 local anesthetic agent Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000011987 methylation Effects 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 2
FDPFLMASHCPTTM-UHFFFAOYSA-N 4-butoxy-2,6-dimethylbenzoyl chloride Chemical compound CCCCOC1=CC(C)=C(C(Cl)=O)C(C)=C1 FDPFLMASHCPTTM-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
210000004087 cornea Anatomy 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229960005015 local anesthetics Drugs 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
210000005036 nerve Anatomy 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
229940035674 anesthetics Drugs 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002690 local anesthesia Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000002276 neurotropic effect Effects 0.000 description 1
239000003960 organic solvent Substances 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
230000002829 reductive effect Effects 0.000 description 1
238000005245 sintering Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
- 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
- C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/02—Preparation by ring-closure or hydrogenation
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/125—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)

CH101570A 1967-10-20 1967-10-20 Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden CH488691A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH101570A CH488691A (de)	1967-10-20	1967-10-20	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1472667A CH487145A (de)	1967-10-20	1967-10-20	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden
CH101570A CH488691A (de)	1967-10-20	1967-10-20	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden

Publications (1)

Publication Number	Publication Date
CH488691A true CH488691A (de)	1970-04-15

Family

ID=4403338

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH101570A CH488691A (de)	1967-10-20	1967-10-20	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden
CH1472667A CH487145A (de)	1967-10-20	1967-10-20	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1472667A CH487145A (de)	1967-10-20	1967-10-20	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden

Country Status (9)

Country	Link
US (1)	US3532704A (fr)
BE (1)	BE722579A (fr)
BR (1)	BR6803205D0 (fr)
CH (2)	CH488691A (fr)
DE (1)	DE1803569A1 (fr)
ES (1)	ES359321A0 (fr)
FR (2)	FR7864M (fr)
GB (1)	GB1218793A (fr)
SE (1)	SE332637B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL7416176A (nl) *	1973-12-26	1975-06-30	Upjohn Co	Werkwijze voor het bevorderen van de productie van endogene prostaglandinen door zoogdieren, alsmede werkwijze ter bereiding van daarbij te gebruiken preparaten.
US4035373A (en) *	1976-02-23	1977-07-12	The University Of Toledo	Preparation of piperidinyl-alkyl-benzamides
US5254569A (en) *	1991-01-14	1993-10-19	The Du Pont Merck Pharmaceutical Company	(Amidomethyl)nitrogen heterocyclic analgesics

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI33631A (fi) *	1959-02-07	1963-11-11	Laeaeketehdas Orion Oy	Aromaattisten orto-disubstituoitujen happoamidien valmistusmenetelmä

1967
- 1967-10-20 CH CH101570A patent/CH488691A/de not_active IP Right Cessation
- 1967-10-20 CH CH1472667A patent/CH487145A/de not_active IP Right Cessation
1968
- 1968-09-12 US US759505A patent/US3532704A/en not_active Expired - Lifetime
- 1968-09-20 SE SE12696/68A patent/SE332637B/xx unknown
- 1968-09-25 GB GB45490/68A patent/GB1218793A/en not_active Expired
- 1968-10-16 FR FR170048A patent/FR7864M/fr not_active Expired
- 1968-10-16 FR FR1603755D patent/FR1603755A/fr not_active Expired
- 1968-10-17 DE DE19681803569 patent/DE1803569A1/de active Pending
- 1968-10-17 BR BR203205/68A patent/BR6803205D0/pt unknown
- 1968-10-18 ES ES359321A patent/ES359321A0/es active Granted
- 1968-10-18 BE BE722579D patent/BE722579A/xx unknown

Also Published As

Publication number	Publication date
BR6803205D0 (pt)	1973-03-08
CH487145A (de)	1970-03-15
ES359321A1 (es)	1970-06-01
FR1603755A (fr)	1971-05-24
GB1218793A (en)	1971-01-13
DE1803569A1 (de)	1969-06-19
US3532704A (en)	1970-10-06
ES359321A0 (es)	1970-06-01
FR7864M (fr)	1970-04-27
BE722579A (fr)	1969-04-18
SE332637B (fr)	1971-02-15

Legal Events

Date	Code	Title	Description
1974-05-31	PL	Patent ceased

Publication	Publication Date	Title
DE2527993A1 (de)	1976-01-15	Quaternaere ammoniumsalze und deren verwendung
DE1420015B1 (de)	1971-08-26	2'-Hydroxy-5,9-dimethyl-6,7-benzomorphane
DE3118162C2 (de)	1984-07-26	1-(4-Chlorbenzhydryl)-4-(2,3-bis-hydroxypropyl)-piperazin, dessen Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltendes Arzneimittel
DE1220425B (de)	1966-07-07	Verfahren zur Herstellung des lokalanaesthetisch wirksamen N-[1'-Benzyl-piperidyl-(4')]-naphthalin-1, 8-dicarbonsaeureimids
CH488691A (de)	1970-04-15	Verfahren zur Herstellung von neuen Butoxy-dimethylbenzamiden
DE2528194C2 (de)	1982-10-14	Benzhydryloxyäthylamin-Derivate, deren Salze, Verfahren zur Herstellung derselben und solche enthaltende Arzneimittel
DE1135921B (de)	1962-09-06	Verfahren zur Herstellung von heterocyclisch substituierten Morphinanen und deren Salzen
DE1695554C3 (de)	1974-02-21	Verfahren zur Herstellung kondensierter Piperazinonderivate
CH513806A (de)	1971-10-15	Verfahren zur Herstellung von tricyclischen Verbindungen
CH369759A (de)	1963-06-15	Verfahren zur Herstellung von N-Alkylpiperidin-a-carbonsäureaniliden
DE69005233T2 (de)	1994-04-28	N-Acyl- und O-Acyl-Derivate von N,N-bis(2,2-Dimethyl-3-Hydroxypropyl)amin, ihre Herstellung und Verwendung.
AT333252B (de)	1976-11-10	Verfahren zur herstellung von neuen racemischen und optisch aktiven aminophenylathanolaminen
DE1443604C3 (de)	1978-11-02	1 -Aminomethyl-1,2-dihydro-benzocyclobuten und einige seiner Derivate, Salze dieser Verbindungen, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende pharmazeutische Präparate
AT288413B (de)	1971-03-10	Verfahren zur Herstellung neuer basischer Xanthonderivate und ihrer Salze
DE1249851B (de)	1967-09-14	Morel Ariesheim (Schweiz) j Verfahren zur Herstellung neuer Phenoxyessigsäure amide
AT334882B (de)	1977-02-10	Verfahren zur herstellung von neuen optisch aktiven aminophenyl-athanolaminen
DE2360407A1 (de)	1974-06-12	Herstellung von omega-amino-betaalkoxycarbonsauren estern
DE1921340C3 (de)	1974-10-31	In 4-Stellung substituierte 2-Phenyl-5-haIogen-pyrimidine
AT333258B (de)	1976-11-10	Verfahren zur herstellung von neuen aminophenyl-athanolaminen
AT231446B (de)	1964-01-27	Verfahren zur Herstellung von neuen Pyridyl-(2)-alkylaminoverbindungen
DE871897C (de)	1953-03-26	Verfahren zur Herstellung von heterocyclischen Aminoverbindungen
AT265530B (de)	1968-10-10	Verfahren zur Herstellung von neuen Isochinolinderivaten
AT375643B (de)	1984-08-27	Verfahren zur herstellung von neuen 4,5,6,7tetrahydroisoindolderivat und von deren salzen
AT215998B (de)	1961-07-10	Verfahren zur Herstellung von neuen Hydrazinderivaten
DE2019570C2 (de)	1984-05-30	Wasserlösliches Khellinderivat: 1H,3H-2-Aza-4-methylen-5,8-dimethoxy-furo(2'',3'',6,7)xanthon-2-spiro-1'-piperidiniumchlorid und Verfahren zu seiner Herstellung