NO115019B - - Google Patents
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- NO115019B NO115019B NO145316A NO14531662A NO115019B NO 115019 B NO115019 B NO 115019B NO 145316 A NO145316 A NO 145316A NO 14531662 A NO14531662 A NO 14531662A NO 115019 B NO115019 B NO 115019B
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- Norway
- Prior art keywords
- phenthiazine
- carbon atoms
- chloro
- general formula
- atom
- Prior art date
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- 238000000034 method Methods 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 4
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241001122767 Theaceae Species 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SWGZHHCRMZDRSN-BTJKTKAUSA-N (Z)-but-2-enedioic acid 1-phenoxypropan-2-ylhydrazine Chemical compound OC(=O)\C=C/C(O)=O.NNC(C)COC1=CC=CC=C1 SWGZHHCRMZDRSN-BTJKTKAUSA-N 0.000 description 1
- YSBNLURGLOLRFL-UHFFFAOYSA-N 2-(1-chloropropan-2-yloxy)oxane Chemical compound ClCC(C)OC1OCCCC1 YSBNLURGLOLRFL-UHFFFAOYSA-N 0.000 description 1
- QFXXARKSLAKVRL-UHFFFAOYSA-N 2-(3-chloropropoxy)oxane Chemical compound ClCCCOC1CCCCO1 QFXXARKSLAKVRL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- IKWQWOFXRCUIFT-UHFFFAOYSA-N benzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C(=O)NN IKWQWOFXRCUIFT-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- -1 thionyl- Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D07—ROPES; CABLES OTHER THAN ELECTRIC
- D07B—ROPES OR CABLES IN GENERAL
- D07B7/00—Details of, or auxiliary devices incorporated in, rope- or cable-making machines; Auxiliary apparatus associated with such machines
- D07B7/02—Machine details; Auxiliary devices
- D07B7/14—Machine details; Auxiliary devices for coating or wrapping ropes, cables, or component strands thereof
Landscapes
- Ropes Or Cables (AREA)
- Storage Of Web-Like Or Filamentary Materials (AREA)
- Mechanical Means For Catching Fish (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Fremgangsmåte for fremstilling av fentiazinderivater. Process for the preparation of phenthiazine derivatives.
Nærværende oppfinnelse vedrører fremstilling av N-aminoalkyl fentiaziner som er verdifulle mellomprodukter ved syntesen av fentiazinderivater med terapeutisk verdi. The present invention relates to the production of N-aminoalkyl phenthiazines which are valuable intermediates in the synthesis of phenthiazine derivatives with therapeutic value.
Det er hensikten med nærværende oppfinnelse å fremskaffe en klasse av fentiazinderivater med den generelle formel: It is the purpose of the present invention to provide a class of phenthiazine derivatives with the general formula:
i hvilken X betyr et vannstoffatom, et ha-logen (f. eks. klor)-atom eller et alkyl eller alkoksyradikal inneholdende opp til 4 kullstoffatomer, f. eks. metyl eller metoksy, i 1- eller 3-stilling, og A betyr en toverdig rett eller forgrenet alifatisk kjede inneholdende 2 eller 3 kullstoffatomer, f. eks. in which X means a hydrogen atom, a halogen (e.g. chlorine) atom or an alkyl or alkoxy radical containing up to 4 carbon atoms, e.g. methyl or methoxy, in the 1- or 3-position, and A means a divalent straight or branched aliphatic chain containing 2 or 3 carbon atoms, e.g.
Oppfinnelsen omfatter videre The invention further includes
salter av nevnte aminobaser. salts of said amino bases.
Forannevnte forbindelser kan omdan-nes til forbindelser av terapeutisk verdi, f. eks. ved alkylering av aminogruppen, f. eks. di-metylering av nevnte gruppe. The aforementioned compounds can be converted into compounds of therapeutic value, e.g. by alkylating the amino group, e.g. dimethylation of said group.
Overensstemmende med nærværende oppfinnelse fremstilles forannevnte forbindelser eller deres salter ved å behandle et tilsvarende 10-halogenalkylfentiazin med formelen In accordance with the present invention, the aforementioned compounds or their salts are prepared by treating a corresponding 10-haloalkylphenthiazine with the formula
hvor Y er et halogenatom, f. eks. klor eller brom, med kaliumftalimid fulgt av spalting av bindingene mellom kvelstoffatomet i sidekjeden og karbonylkullstof f atomene av ftalimidderivatet enten ved sur eller alkalisk hydrolyse eller ved innvirkning av et hydrazin og derpå, hvis ønsket, omdanning av den oppnådde N-aminoalkyl fentiazin-forbindelse til et salt av denne. Egnede sy-rer for forannevnte sure hydrolyse er saltsyre og bromvannstoffsyre. Alkalisk hydrolyse kan oppnås med f. eks. kaustisk soda. where Y is a halogen atom, e.g. chlorine or bromine, with potassium phthalimide followed by cleavage of the bonds between the nitrogen atom in the side chain and the carbonyl carbon f atoms of the phthalimide derivative either by acid or alkaline hydrolysis or by the action of a hydrazine and then, if desired, conversion of the obtained N-aminoalkyl phenthiazine compound into a salt of this. Suitable acids for the aforementioned acidic hydrolysis are hydrochloric acid and hydrobromic acid. Alkaline hydrolysis can be achieved with e.g. caustic soda.
De følgende eksempler tjener til å illu-strere oppfinnelsen. De angitte smelte-punkter bestemtes ved Kofler-metoden. The following examples serve to illustrate the invention. The indicated melting points were determined by the Kofler method.
Eksempel 1: Example 1:
50 cm<3> dimetylformamid oppvarmes under tilbakeløp i 15 timer med 18,5 g kaliumftalimid og 26,1 g 10-(2'-kloretyl)-fentiazin (fremstilt i overensstemmelse med den generelle metode beskrevet av Gilman og Shirley, J. Amer. Chem. Soc. 66, 890 (1944)). Den avkjølte blanding helles i 300 cm<3> vann. Etter filtrering, vasking med vann og tørring ved 110° C oppnås 37 g 10-(2'-ftalimid-etyl)fentiazin, som smelter ved 173—174° C etter omkrystallisering fra 15 deler aceton. 50 cm<3> of dimethylformamide is heated under reflux for 15 hours with 18.5 g of potassium phthalimide and 26.1 g of 10-(2'-chloroethyl)-phenthiazine (prepared in accordance with the general method described by Gilman and Shirley, J. Amer . Chem. Soc. 66, 890 (1944)). The cooled mixture is poured into 300 cm<3> of water. After filtration, washing with water and drying at 110° C, 37 g of 10-(2'-phthalimidoethyl)phenthiazine are obtained, which melts at 173-174° C after recrystallization from 15 parts of acetone.
100 cm<3> absolutt alkohol, 11,6 g 10-(2'- 100 cm<3> absolute alcohol, 11.6 g 10-(2'-
ftalimid-etyl)fentiazin og 1,65 g hydrazin- phthalimide-ethyl)phenthiazine and 1.65 g of hydrazine-
hydrat (100 pst.) oppvarmes i 1 time under tilbakeløp i overensstemmelse med Ing og Manske's metode, J. Chem. Soc. 1926, 2348. hydrate (100 per cent) is heated for 1 hour under reflux in accordance with Ing and Manske's method, J. Chem. Soc. 1926, 2348.
10 cm<*> saltsyre (d = 1,19) tilsettes der- 10 cm<*> hydrochloric acid (d = 1.19) is added there-
på, og blandingen opphetes ytterligere 1 on, and the mixture is heated a further 1
time under tilbakeløp. Den kjøles derpå til 20° C, ftalylhydrazidet filtreres fra, og den alkoholiske oppløsning konsentreres i va- hour during reflux. It is then cooled to 20° C, the phthalylhydrazide is filtered off, and the alcoholic solution is concentrated in water
kuum. Resten tas opp i 100 cm<3> kokende vann, avfarges med trekull og filtreres. kuum. The residue is taken up in 100 cm<3> of boiling water, decolorized with charcoal and filtered.
Eter kjøling oppnås 7,5 g av hydroklor- Ether cooling yields 7.5 g of hydrochloride
idte av 10-(2'-aminoetyl)-fentiazin (smel- ide of 10-(2'-aminoethyl)-phenthiazine (mel-
tepunkt 270—271° C). tea point 270—271° C).
Det sure maleat av 10-(2'-aminoetyl)- The acidic maleate of 10-(2'-aminoethyl)-
fentiazin smelter ved 181° C. phenthiazine melts at 181°C.
Eksempel 2: Example 2:
50 cm<3> dimetylformamid oppvarmes i 50 cm<3> of dimethylformamide is heated in
5 timer under tilbakeløp med 11,3 g kalium- 5 hours under reflux with 11.3 g of potassium
ftalimid og 19 g 3-klor-10-(3'-kloropropyl)- phthalimide and 19 g of 3-chloro-10-(3'-chloropropyl)-
fentiazin fremstilt i overensstemmelse med Gilman og Shirley's metode henvist til i phenthiazine prepared in accordance with Gilman and Shirley's method referred to in
eksempel 1. Den kolde reaksjonsblanding helles i 400 cm3 destillert vann og blandin- example 1. The cold reaction mixture is poured into 400 cm3 of distilled water and mixed
gen omrøres i en halv time. Det frafiltrerte faste stoff oppløses i 360 cm<3> varm etyl- and stir for half an hour. The filtered off solid is dissolved in 360 cm<3> of hot ethyl
alkohol og behandles med trekull. Etter kjøling oppnås 3-klor-10-(3'-ftalimidpro-pyl)fentiazin som smelter ved 115° C. Spalt- alcohol and treated with charcoal. After cooling, 3-chloro-10-(3'-phthalimidopropyl)phenthiazine is obtained which melts at 115° C. Split-
ing av ftalimidderivatet utføres med hy- ing of the phthalimide derivative is carried out with hy-
drazin som i eksempel 1. 3-klor-10-(3'-ami-nopropyl)fentiazin oppnås, fra hvilket ma- drazine as in example 1. 3-chloro-10-(3'-aminopropyl)phenthiazine is obtained, from which ma-
leatet fremstilles, smeltepunkt 191—192° C. leat is produced, melting point 191-192° C.
Eksempel 3: Example 3:
En oppløsning av 20 g 10-(2'-klorpro- A solution of 20 g of 10-(2'-chloropro-
pyl) fentiazin og 13,4 g kaliumftalimid i 60 pyl) phenthiazine and 13.4 g potassium phthalimide in 60
cm<3> dimetylformamid oppvarmes under til- cm<3> dimethylformamide is heated under
bakeløp i 4 timer. Etter avkjøling helles produktet i vann, filtreres og omkrystallise- back race for 4 hours. After cooling, the product is poured into water, filtered and recrystallized
res fra etylalkohol. På denne måte oppnås 6,3 g 10-(2'-ftalimid-propyl)fentiazin (smel- res from ethyl alcohol. In this way, 6.3 g of 10-(2'-phthalimid-propyl)phenthiazine (melt-
tepunkt 172—174° C). tea point 172-174° C).
En oppløsning av 6 g 10-(2'-ftalimid-propyl) fentiazin og 0,85 g hydrazin hydrat (95 pst.) i 250 cm<3> etylalkohol oppvarmes i 4 timer under tilbakeløp. Produktet kjøles, A solution of 6 g of 10-(2'-phthalimido-propyl) phenthiazine and 0.85 g of hydrazine hydrate (95 per cent) in 250 cm<3> of ethyl alcohol is heated for 4 hours under reflux. The product is cooled,
og 4,5 cm<3> saltsyre (d = 1,19) tilsettes. Blandingen opphetes derpå i ytterligere 1 y2 time. under tilbakeløp. Etter avkjøling fil- and 4.5 cm<3> hydrochloric acid (d = 1.19) is added. The mixture is then heated for a further 1-2 hours. during reflux. After cooling file-
treres blandingen, og det dannede bunnfall vaskes méd alkohol. De alkoholiske filtra- the mixture is filtered, and the precipitate formed is washed with alcohol. The alcoholic filters
ter samles opp, og alkoholen fordampes over vannbad. Produktet gjøres alkalisk ved tilsetning av 15 cm<3> 10N kaustisk soda og ekstraheres med 500 cm<3> eter. Eterekstrak- ter is collected, and the alcohol is evaporated over a water bath. The product is made alkaline by adding 15 cm<3> of 10N caustic soda and extracted with 500 cm<3> of ether. ether extract-
tet tørres over natriumsulfat, og eteren for- dried over sodium sulfate, and the ether
dampes over vannbad. 4 g 10-(2'-amino- steam over a water bath. 4 g of 10-(2'-amino-
propyl) fentiazin oppnås på denne måte, og dette produkt renses ved å omdanne det til propyl) phenthiazine is obtained in this way, and this product is purified by converting it to
hydrokloridet, som etter omkrystallisasjon fra en blanding av etylalkohol og cyklo- the hydrochloride, which after recrystallization from a mixture of ethyl alcohol and cyclo-
heksan smelter ved 244—245° C. 10-(2'-amino-propyl)fentiazin-basen smelter ved 132—133° C. hexane melts at 244-245° C. The 10-(2'-amino-propyl)phenthiazine base melts at 132-133° C.
10- (2'-klorpropyl) f entiazinet (smelte- 10-(2'-Chloropropyl)fenthiazine (melt-
punkt 120—122° C) brukt som utgangsma- point 120—122° C) used as starting material
teriale oppnås ved innvirkning av tionyl- terial is obtained by the action of thionyl-
klorid på 10-(2'-hydroksy-propyl)fentiazin (kokepunkt 0,35 = 190—195° C), som på sin side fremstilles ved saltsyresur hydrolyse av 10-(2'-tetrahydropyranyloksypropyl) fenti- chloride of 10-(2'-hydroxypropyl)phenthiazine (boiling point 0.35 = 190-195° C), which in turn is produced by hydrochloric acid hydrolysis of 10-(2'-tetrahydropyranyloxypropyl)pheni-
azin fremstilt ved innvirkning av 2-tetra-hydropyranyloksy-l-klorpropan på fentia- azine prepared by the action of 2-tetra-hydropyranyloxy-1-chloropropane on fenthia-
zin i xylen i nærvær av natriumamid. zin in xylene in the presence of sodium amide.
Eksempel 4: Example 4:
Ved å gå frem som i eksempel III, men By proceeding as in example III, but
ved å gå ut fra l-klor-10-(3'-klorpropyl)- starting from 1-chloro-10-(3'-chloropropyl)-
fentiazin, l-klor-10-3'-aminopropyl) fenti- phenthiazine, l-chloro-10-3'-aminopropyl) pheny-
azin oppnås l-klor-10-(3'-aminopropyl) azine is obtained 1-chloro-10-(3'-aminopropyl)
fentiazin hvis maleat smelter ved 169° C. phenthiazine whose maleate melts at 169°C.
1 -klor-10- (3'-klorpropyl) fentiazin frem- 1 -Chloro-10-(3'-chloropropyl) phenthiazine pre-
stilles på samme måte som 10-^'-klorpropyl) fentiazin i eksempel III fra 1-klor- is prepared in the same way as 10-^'-chloropropyl) phenthiazine in example III from 1-chloro-
fentiazin og 3-tetrahydropyranyloksy-l-klorpropan ved mellomproduktet l-klor-10-(3'-hydroksy-propyl) fentiazin (kokepunkt 0,35 = 225—223° C). phenthiazine and 3-tetrahydropyranyloxy-1-chloropropane by the intermediate product 1-chloro-10-(3'-hydroxy-propyl) phenthiazine (boiling point 0.35 = 225-223° C).
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV21200A DE1255001B (en) | 1961-08-19 | 1961-08-19 | Device for spinning a rope core made of synthetic threads |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115019B true NO115019B (en) | 1968-07-01 |
Family
ID=7579016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO145316A NO115019B (en) | 1961-08-19 | 1962-08-03 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3141285A (en) |
| BE (1) | BE619990A (en) |
| CH (1) | CH394875A (en) |
| DE (1) | DE1255001B (en) |
| NL (1) | NL281338A (en) |
| NO (1) | NO115019B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7005105A (en) * | 1969-07-04 | 1971-01-06 | ||
| FR2531464A1 (en) * | 1982-08-03 | 1984-02-10 | Giraudon Ets M | Automatic machine intended for the continuous production of twisted cords used especially for making curtain loops. |
| GB2127869B (en) * | 1982-09-22 | 1986-04-30 | Standard Telephones Cables Ltd | Optical fibre cable manufacture |
| DE3240230C2 (en) * | 1982-10-29 | 1987-02-05 | Siemens AG, 1000 Berlin und 8000 München | Rotating yarn spinner |
| US20230404193A1 (en) * | 2022-06-21 | 2023-12-21 | Lakshmanan Varadan | System and method for forming a garland |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1704888A (en) * | 1929-03-12 | Assianob tq the wire | ||
| DE444006C (en) * | 1927-05-13 | Mueller Fritz | Device for plating trimmings threads | |
| DE37770C (en) * | firma hannoversche Caoutchouc-, Guttapercha- und telegraphen-werke in Linden—Hannover | Machine for the simultaneous application of two systems of thread-like bodies on rubber hoses | ||
| US303943A (en) * | 1884-08-19 | morton | ||
| DE186435C (en) * | ||||
| US946162A (en) * | 1907-03-21 | 1910-01-11 | Fairfield Smith | Cord-twisting machine. |
| AT54549B (en) * | 1911-11-13 | 1912-07-25 | Fried Krupp Actiengesellschaft | Rope laying machine. |
| US1210001A (en) * | 1916-02-10 | 1916-12-26 | Ivan L C Gooding | Wire-covering machine. |
| US1747769A (en) * | 1928-06-04 | 1930-02-18 | Nat Metal Molding Company | Apparatus for the manufacture of electrical conductors |
| DE643817C (en) * | 1930-12-24 | 1937-04-17 | Siemens & Halske Akt Ges | Device for producing telecommunication cables |
| US1907744A (en) * | 1931-09-16 | 1933-05-09 | Roeblings John A Sons Co | Rope making machine |
| US2098922A (en) * | 1934-01-08 | 1937-11-09 | Gen Cable Corp | Apparatus for making cable |
| US2249781A (en) * | 1940-07-20 | 1941-07-22 | Nat Electric Prod Corp | Serving head |
| US2423289A (en) * | 1945-07-17 | 1947-07-01 | Charles M Bellg | Wire wrapping machine |
| US2672722A (en) * | 1949-10-18 | 1954-03-23 | Wardwell Braiding Machine Comp | Serving machine |
| US2780906A (en) * | 1954-04-02 | 1957-02-12 | Northern Electric Co | Apparatus for forming multi-element cable |
| DE1038226B (en) * | 1955-09-07 | 1958-09-04 | Felten & Guilleaume Carlswerk | Device for spinning wires, strands, ropes or the like. |
| FR1191528A (en) * | 1958-02-14 | 1959-10-20 | Automatic guipeuse | |
| US3058867A (en) * | 1959-11-02 | 1962-10-16 | Walter A Plummer | Cabling machine and method of producing jacketed cable |
-
0
- NL NL281338D patent/NL281338A/xx unknown
-
1961
- 1961-08-19 DE DEV21200A patent/DE1255001B/en active Pending
-
1962
- 1962-07-10 BE BE619990A patent/BE619990A/en unknown
- 1962-07-14 CH CH850462A patent/CH394875A/en unknown
- 1962-08-03 NO NO145316A patent/NO115019B/no unknown
- 1962-08-14 US US216890A patent/US3141285A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1255001B (en) | 1967-11-23 |
| CH394875A (en) | 1965-06-30 |
| US3141285A (en) | 1964-07-21 |
| BE619990A (en) | 1962-11-05 |
| NL281338A (en) |
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