NO146427B - INTERMEDIATE IN THE PREPARATION OF 1-ISOPROPYLAMINE-3- (P- (2-METOXYETHYL) PHENOXY) -2-PROPANOL - Google Patents
INTERMEDIATE IN THE PREPARATION OF 1-ISOPROPYLAMINE-3- (P- (2-METOXYETHYL) PHENOXY) -2-PROPANOL Download PDFInfo
- Publication number
- NO146427B NO146427B NO810811A NO810811A NO146427B NO 146427 B NO146427 B NO 146427B NO 810811 A NO810811 A NO 810811A NO 810811 A NO810811 A NO 810811A NO 146427 B NO146427 B NO 146427B
- Authority
- NO
- Norway
- Prior art keywords
- phenoxy
- isopropylamine
- propanol
- preparation
- metoxyethyl
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title abstract description 4
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title 1
- 239000013067 intermediate product Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- -1 1-isopropylamine-3- [p- (2-methoxyethyl) phenoxy] -2-propanol Chemical compound 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- JJAKDWRVLCNKRN-UHFFFAOYSA-N 4-(1,1-diethoxy-2-methoxyethyl)phenol Chemical compound CCOC(COC)(OCC)C1=CC=C(O)C=C1 JJAKDWRVLCNKRN-UHFFFAOYSA-N 0.000 description 1
- SMIOEQSLJNNKQF-UHFFFAOYSA-N 4-acetoxy acetophenone Chemical compound CC(=O)OC1=CC=C(C(C)=O)C=C1 SMIOEQSLJNNKQF-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Mellomprodukt ved fremstilling av 1-isopropylamin-3-[p-(2-metoksyetyl)fenoksy]-2-propanol.Intermediate in the preparation of 1-isopropylamine-3- [p- (2-methoxyethyl) phenoxy] -2-propanol.
Description
Formålet med foreliggende oppfinnelse er et mellomprodukt med formelen The object of the present invention is an intermediate product with the formula
ved fremstilling av terapeutisk aktiv 1-(isopropylamin)-3-[p-(2-metoksyetyl)fenoksy]-2-propanol med formelen: in the preparation of therapeutically active 1-(isopropylamine)-3-[p-(2-methoxyethyl)phenoxy]-2-propanol with the formula:
Denne sistnevnte forbindelse er kjent for sine terapeutiske egenskaper og anvendes i terapi mot angina pec-toris og forstyrrelser av hjerterytmen. This latter compound is known for its therapeutic properties and is used in therapy against angina pectoris and disturbances of the heart rhythm.
Fremstillingen av nevnte forbindelse er tidligere beskrevet, blant annet i NO-PS 132.798. I denne fremgangsmåte kreves det i fremstillingen av utgangsstoffet flere trinn, og en del av disse trinn har dårlig utbytte. The production of said compound has previously been described, among other things in NO-PS 132,798. In this method, several steps are required in the production of the starting material, and some of these steps have a poor yield.
I den fremgangsmåte som nu er utarbeidet brukes, som utgangsstoff, p-(1,l-dietoksy-2-ketoksyetyl)fenol eller et annet ketalderivat. Angjeldende utgangsstoff kan lett fremstilles ifølge i litteraturen angitte fremgangsmåter fra 4-acetoksyacetofenon. In the method that has now been developed, p-(1,1-diethoxy-2-ketoxyethyl)phenol or another ketal derivative is used as starting material. The starting material in question can be easily prepared according to methods specified in the literature from 4-acetoxyacetophenone.
Man lar ketalderivatet: One allows the ketal derivative:
reagere med epiklorhydrin, hvorved det oppnås en forbindelse med formelen: react with epichlorohydrin, whereby a compound of the formula is obtained:
Forbindelsen III amineres i isopropylamin, hvoretter ketalet nedbrytes i sur vannoppløsning, hvorved det oppnås en forbindelse med følgende formel: The compound III is aminated in isopropylamine, after which the ketal is decomposed in acidic water solution, whereby a compound with the following formula is obtained:
Fra forbindelsen II kommer man frem til forbindelsen IV uten rensning av mellomproduktene, hvorved fremstillingen kan ut-føres som en kontinuerlig prosess. From compound II one arrives at compound IV without purification of the intermediate products, whereby the preparation can be carried out as a continuous process.
Fra forbindelsen IV kommer man til sluttproduktet I, ved hjelp av katalytisk hydrering med palladium på karbon i et oppløsning-smiddel bestående av lavere alkoholer ved en temperatur mellom romtemperatur og 80°C og ved et trykk mellom 1 og 5 atmosfærer. From compound IV, the final product I is obtained by means of catalytic hydrogenation with palladium on carbon in a solvent consisting of lower alcohols at a temperature between room temperature and 80°C and at a pressure between 1 and 5 atmospheres.
Følgende eksempler skal illustrere oppfinnelsen nærmere.. The following examples shall illustrate the invention in more detail.
Eksempel 1. Example 1.
1- isopropylamin- 3- Cp-( 2- metoksy- l- oksoetyl) fenoksy]- 2- propanol. 1-isopropylamine-3-Cp-(2-methoxyl-oxoethyl)phenoxy]-2-propanol.
Man fremstiller en natriummetanolatoppløsning med 4,4 g natrium og 270 ml etanol. Til den oppnådde oppløsning tilsettes ved romtemperatur 37,7 g p-(1,1-dietoksy-2-metoksyetyl)fenol. Man tilsetter 55 ml epiklorhydrin og blander ved romtemperatur i 1 døgn. Deretter dampes det hele inn. Resten opptas i kloroform og vaskes med vann. Deretter følger tørking med natrium-sulfat og inndamping. Inndampingsresten oppløses i 300 ml Tso-propylamin, og oppløsningen kokes under tilbakeløp i 1 døgn og deretter dampes det hele inn igjen. Inndampingsresten opp-løses i vann, og oppløsningens pH justeres til 1 ved hjelp av saltsyre. For fullstendig nedbryting av ketalet, blandes det 1 time ved romtemperatur. Deretter følger en vaskeekstrak-sjon med etylacetat. Vannfasen gjøres basisk med konsentrert ammoniakk, og produktet ekstraheres med etylacetat. Ekstrakt-ene behandles med aktivkull, tørkes og dampes inn. Produktet krystalliseres med hydroklorid ved oppløsning i HCl-isopropa-nol og utfelling med etylacetat. Det oppnådde hydroklorid har et smeltepunkt på 125-126°C. A sodium methanolate solution is prepared with 4.4 g of sodium and 270 ml of ethanol. To the solution obtained, 37.7 g of p-(1,1-diethoxy-2-methoxyethyl)phenol are added at room temperature. 55 ml of epichlorohydrin is added and mixed at room temperature for 1 day. The whole thing is then steamed in. The residue is taken up in chloroform and washed with water. This is followed by drying with sodium sulphate and evaporation. The evaporation residue is dissolved in 300 ml of Tso-propylamine, and the solution is boiled under reflux for 1 day and then the whole is evaporated again. The evaporation residue is dissolved in water, and the pH of the solution is adjusted to 1 using hydrochloric acid. For complete decomposition of the ketal, it is mixed for 1 hour at room temperature. This is followed by a washing extraction with ethyl acetate. The water phase is made basic with concentrated ammonia, and the product is extracted with ethyl acetate. The extracts are treated with activated carbon, dried and evaporated. The product is crystallized with hydrochloride by dissolution in HCl-isopropanol and precipitation with ethyl acetate. The resulting hydrochloride has a melting point of 125-126°C.
Eksempel 2. Example 2.
l- isopropylamin- 3-[ p-( 2- metoksyetyl) fenoksy] - 2- propanol l- isopropylamine- 3-[ p-(2- methoxyethyl) phenoxy] - 2- propanol
10 g l-isopropylamin-3-[p-(2-metoksy-l-oksyetyl)-fenoksy]-2-propanolhydroklorid oppløses i 150 ml eddiksyre. Deretter tilsettes 1,5 g 10%-ig palladiumkull, og man gjennomfører en hydrering ved 7 0°C og 5 atmosfærer inntil den teoretiske mengde hydrogen er forbrukt. Deretter filtreres katalysatoren av, og oppløsningsmidlet avdampes. Resten oppløses i vann, og oppløsningen gjøres alkalisk med lut. Produktet oppløses i kloroform. Kloroformen dampes av. Tartratet fremstilles av produktet i vinsurt aceton. Det oppnådde tartrat har et smeltepunkt på ca. 120°C. 10 g of 1-isopropylamine-3-[p-(2-methoxy-1-oxyethyl)-phenoxy]-2-propanol hydrochloride are dissolved in 150 ml of acetic acid. 1.5 g of 10% palladium charcoal is then added, and a hydration is carried out at 70°C and 5 atmospheres until the theoretical amount of hydrogen has been consumed. The catalyst is then filtered off, and the solvent is evaporated. The remainder is dissolved in water, and the solution is made alkaline with lye. The product is dissolved in chloroform. The chloroform is evaporated. The tartrate is prepared from the product in tartaric acetone. The obtained tartrate has a melting point of approx. 120°C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI762507A FI55649C (en) | 1976-09-01 | 1976-09-01 | NYTT FOERFARANDE FOER FRAMSTAELLNING AV 1-ISOPROPYLAMINE-3- (P- (2-METHOXYETHYL) PHENOXY) -2-PROPANOL |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO810811L NO810811L (en) | 1978-03-02 |
| NO146427B true NO146427B (en) | 1982-06-21 |
| NO146427C NO146427C (en) | 1982-09-29 |
Family
ID=8510232
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771897A NO144958C (en) | 1976-09-01 | 1977-05-31 | PROCEDURE FOR PREPARING 1-ISOPROPYLAMINE-3- (P- (2-METOXYETHYL) PHENOXY) -2-PROPANOL |
| NO810810A NO147301C (en) | 1976-09-01 | 1981-03-10 | INTERMEDIATE IN THE PREPARATION OF 1-ISOPROPYLAMINE-3- (P-2 (2-METOXYETHYL) PHENOXY) -2-PROPANOL |
| NO810811A NO146427C (en) | 1976-09-01 | 1981-03-10 | INTERMEDIATE IN THE PREPARATION OF 1-ISOPROPYLAMINE-3- (P- (2-METOXYETHYL) PHENOXY) -2-PROPANOL |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771897A NO144958C (en) | 1976-09-01 | 1977-05-31 | PROCEDURE FOR PREPARING 1-ISOPROPYLAMINE-3- (P- (2-METOXYETHYL) PHENOXY) -2-PROPANOL |
| NO810810A NO147301C (en) | 1976-09-01 | 1981-03-10 | INTERMEDIATE IN THE PREPARATION OF 1-ISOPROPYLAMINE-3- (P-2 (2-METOXYETHYL) PHENOXY) -2-PROPANOL |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS606350B2 (en) |
| DK (1) | DK213877A (en) |
| FI (1) | FI55649C (en) |
| NO (3) | NO144958C (en) |
| PL (1) | PL109138B1 (en) |
| SE (3) | SE443137B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL212286B1 (en) | 2010-06-20 | 2012-09-28 | Inst Immunologii I Terapii Doswiadczalnej Pan | Method for the preparation of bacteriophages |
-
1976
- 1976-09-01 FI FI762507A patent/FI55649C/en not_active IP Right Cessation
-
1977
- 1977-02-04 PL PL1977195815A patent/PL109138B1/en unknown
- 1977-05-03 SE SE7705120A patent/SE443137B/en not_active IP Right Cessation
- 1977-05-17 DK DK213877A patent/DK213877A/en not_active Application Discontinuation
- 1977-05-31 NO NO771897A patent/NO144958C/en unknown
- 1977-06-15 JP JP52071587A patent/JPS606350B2/en not_active Expired
-
1981
- 1981-03-10 NO NO810810A patent/NO147301C/en unknown
- 1981-03-10 NO NO810811A patent/NO146427C/en unknown
-
1985
- 1985-10-25 SE SE8505036A patent/SE462490B/en not_active IP Right Cessation
- 1985-10-25 SE SE8505035A patent/SE462489B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53105440A (en) | 1978-09-13 |
| SE8505036D0 (en) | 1985-10-25 |
| SE8505035L (en) | 1985-10-25 |
| SE462490B (en) | 1990-07-02 |
| SE443137B (en) | 1986-02-17 |
| SE8505035D0 (en) | 1985-10-25 |
| PL109138B1 (en) | 1980-05-31 |
| NO147301B (en) | 1982-12-06 |
| NO146427C (en) | 1982-09-29 |
| SE7705120L (en) | 1978-03-02 |
| SE8505036L (en) | 1985-10-25 |
| NO147301C (en) | 1983-03-16 |
| NO144958C (en) | 1981-12-16 |
| FI55649B (en) | 1979-05-31 |
| NO810810L (en) | 1978-03-02 |
| NO771897L (en) | 1978-03-02 |
| NO144958B (en) | 1981-09-07 |
| PL195815A1 (en) | 1978-03-13 |
| FI762507A (en) | 1978-03-02 |
| NO810811L (en) | 1978-03-02 |
| FI55649C (en) | 1979-09-10 |
| DK213877A (en) | 1978-03-02 |
| SE462489B (en) | 1990-07-02 |
| JPS606350B2 (en) | 1985-02-18 |
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