NO790116L - Mellomprodukter for bruk ved fremstilling av terapeutisk virksomme forbindelser - Google Patents

Mellomprodukter for bruk ved fremstilling av terapeutisk virksomme forbindelser

Info

Publication number: NO790116L
Authority: NO; Norway
Prior art keywords: compound; ethyl; formula; active compounds; manufacture
Prior art date: 1978-01-30

Application number

NO790116A

Other languages

English (en)

Norwegian (no)

Inventor

Peter Bamberg

Thore Oskar Vaerner Rydh

Jan Urban Stenhede

Original Assignee

Astra Pharma Prod

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.)

1978-01-30

Filing date

1979-01-15

Publication date

1979-07-31

1979-01-15 Application filed by Astra Pharma Prod filed Critical Astra Pharma Prod

1979-07-31 Publication of NO790116L publication Critical patent/NO790116L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 36
238000004519 manufacturing process Methods 0.000 title claims description 7
239000013067 intermediate product Substances 0.000 title description 3
230000001225 therapeutic effect Effects 0.000 title 1
238000000034 method Methods 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 claims description 2
150000001805 chlorine compounds Chemical group 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
229940008406 diethyl sulfate Drugs 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000037361 pathway Effects 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
KVQWXHKUOVJOHR-UHFFFAOYSA-N N-ethylpropan-1-amine hydrobromide Chemical compound [Br-].C(C)[NH2+]CCC KVQWXHKUOVJOHR-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 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
238000009835 boiling Methods 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
239000000383 hazardous chemical Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
-1 α-(N-ethyl-N-n-propylamino)-butyric acid ethyl ester Chemical compound 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO790116A 1978-01-30 1979-01-15 Mellomprodukter for bruk ved fremstilling av terapeutisk virksomme forbindelser NO790116L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE7801062A SE424442B (sv)	1978-01-30	1978-01-30	Estrar av alfa-(n-etyl-n-n-propylamin)-smorsyra till anvendning som mellanprodukter vid framstellning av terapeutiskt aktiva foreningar

Publications (1)

Publication Number	Publication Date
NO790116L true NO790116L (no)	1979-07-31

Family

ID=20333796

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO790116A NO790116L (no)	1978-01-30	1979-01-15	Mellomprodukter for bruk ved fremstilling av terapeutisk virksomme forbindelser

Country Status (9)

Country	Link
JP (1)	JPS54112821A (da)
AT (1)	AT367393B (da)
DK (1)	DK20879A (da)
ES (1)	ES477051A1 (da)
FI (1)	FI790229A7 (da)
IT (1)	IT1116533B (da)
NL (1)	NL7900643A (da)
NO (1)	NO790116L (da)
SE (1)	SE424442B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3401969A (en) *	1966-10-28	1968-09-17	Forest J. Neel	Safety chain locking device
US3544154A (en) *	1968-07-26	1970-12-01	Gailerd B Ford	Dump truck spreader chain mounting

1978
- 1978-01-30 SE SE7801062A patent/SE424442B/sv unknown
1979
- 1979-01-15 NO NO790116A patent/NO790116L/no unknown
- 1979-01-18 DK DK20879A patent/DK20879A/da not_active Application Discontinuation
- 1979-01-22 ES ES477051A patent/ES477051A1/es not_active Expired
- 1979-01-24 IT IT47765/79A patent/IT1116533B/it active
- 1979-01-24 FI FI790229A patent/FI790229A7/fi unknown
- 1979-01-26 AT AT0059279A patent/AT367393B/de not_active IP Right Cessation
- 1979-01-26 NL NL7900643A patent/NL7900643A/xx not_active Application Discontinuation
- 1979-01-30 JP JP881679A patent/JPS54112821A/ja active Pending

Also Published As

Publication number	Publication date
FI790229A7 (fi)	1979-07-31
SE424442B (sv)	1982-07-19
NL7900643A (nl)	1979-08-01
AT367393B (de)	1982-06-25
IT7947765A0 (it)	1979-01-24
IT1116533B (it)	1986-02-10
SE7801062L (sv)	1979-07-31
ATA59279A (de)	1981-11-15
DK20879A (da)	1979-07-31
ES477051A1 (es)	1979-06-16
JPS54112821A (en)	1979-09-04

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DE69010285T2 (de)	1994-10-13	Als Spasmolytica geeignete Dibenzothiazepin-Derivate.
JPH0393787A (ja)	1991-04-18	抗ウイルス活性を有する薬剤、燐脂質誘導体及びその製造方法
JPH0261950B2 (da)	1990-12-21
DK152752B (da)	1988-05-09	Fremgangsmaade til fremstilling af l-sulpirid
US3190918A (en)	1965-06-22	Process for the production of chlorosubstituted methyl isocyanide dichlorides
NO790116L (no)	1979-07-31	Mellomprodukter for bruk ved fremstilling av terapeutisk virksomme forbindelser
SE431643B (sv)	1984-02-20	Terapeutiskt aktiva halogensubstituerade prolinderivat innehallande svavel och forfarande for deras tillverkning
EP0396613A1 (en)	1990-11-14	Cyano-dienes, halopyridines, intermediates and a process for their preparation
US4292431A (en)	1981-09-29	Process for the production of hydroxymethylimidazoles
US3691198A (en)	1972-09-12	Synthesis of 1-substituted-3-halopyrrolidines
US5663365A (en)	1997-09-02	Process for the preparation of pyrazolones
EP0220025B1 (en)	1991-09-18	3-perfluoroalkyl-5-hydroxyisoxazoles
NO170542B (no)	1992-07-20	Fremgangsmaate for fremstilling av en basisk thioether og saltet derav
US2671798A (en)	1954-03-09	2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same
US4200757A (en)	1980-04-29	Process for the production of 3-aminoisoxazoles
US3072636A (en)	1963-01-08	Process for the manufacture of ethyleneimine derivatives
CA1052383A (en)	1979-04-10	Process for the production of 1,2,4-triazole derivatives
SU507227A3 (ru)	1976-03-15	Способ получени -(аминофенил-)-алифатических производных карбоновых кислот или их солей, или их -окисей
DK158038B (da)	1990-03-19	Fremgangsmaade til fremstilling af di-n-propylacetonitril
US2030373A (en)	1936-02-11	Derivatives of thiazole and process of preparing the same
DE68907032T2 (de)	1994-01-20	Verfahren zur Herstellung von 1,4-Überbrückten-Cyclohexancarbonsäure-Derivaten und ihre Verwendung.
HU193454B (en)	1987-10-28	Process for producing 3-phenyl-butyraldehyde derivatives
US3883593A (en)	1975-05-13	10-Nitro-5h-dibenzo(a,d)cyclohepten-5-ones and selected derivatives
SU943240A1 (ru)	1982-07-15	Способ получени производных 10-окси-10н-пиридо [2,3- @ ХРОМЕНОВ