LU83039A1 - Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol - Google Patents

Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol Download PDF

Info

Publication number: LU83039A1
Authority: LU; Luxembourg
Prior art keywords: isopropylthiophenyl; synthesis; octyl; salts; octylaminopropanol
Prior art date: 1980-12-24

Application number

LU83039A

Other languages

English (en)

French (fr)

Inventor

G Lambelin

C Gillet

J Hermans

Original Assignee

Continental Pharma

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.)

1980-12-24

Filing date

1980-12-24

Publication date

1982-07-07

1980-12-24 Application filed by Continental Pharma filed Critical Continental Pharma

1980-12-24 Priority to LU83039A priority Critical patent/LU83039A1/fr

1981-12-21 Priority to AT0549881A priority patent/AT380872B/de

1981-12-23 Priority to PT74203A priority patent/PT74203B/pt

1981-12-23 Priority to CH8259/81A priority patent/CH653325A5/fr

1981-12-23 Priority to ES508313A priority patent/ES508313A0/es

1981-12-23 Priority to AR287941A priority patent/AR229799A1/es

1981-12-23 Priority to IL64631A priority patent/IL64631A0/xx

1981-12-23 Priority to CH443/85A priority patent/CH654296A5/fr

1981-12-24 Priority to AU79025/81A priority patent/AU548084B2/en

1981-12-24 Priority to JP56208270A priority patent/JPS5912665B2/ja

1981-12-24 Priority to IT25853/81A priority patent/IT1140399B/it

1981-12-24 Priority to KR1019810005129A priority patent/KR860000340B1/ko

1982-07-07 Publication of LU83039A1 publication Critical patent/LU83039A1/fr

1982-12-06 Priority to JP57212827A priority patent/JPS5915906B2/ja

1982-12-06 Priority to JP57212825A priority patent/JPS5938224B2/ja

1982-12-06 Priority to JP57212826A priority patent/JPS5915905B2/ja

1983-05-16 Priority to ES522440A priority patent/ES8407018A1/es

1983-05-16 Priority to ES522441A priority patent/ES522441A0/es

1983-05-16 Priority to ES522442A priority patent/ES522442A0/es

1983-11-28 Priority to AT416183A priority patent/AT380873B/de

1984-08-08 Priority to AT257384A priority patent/AT380874B/de

1985-02-10 Priority to IL74290A priority patent/IL74290A0/xx

Links

238000000034 method Methods 0.000 title claims description 25
230000015572 biosynthetic process Effects 0.000 title claims description 9
238000003786 synthesis reaction Methods 0.000 title claims description 9
BFCDFTHTSVTWOG-UHFFFAOYSA-N 2-(octylamino)-1-[4-(propan-2-ylthio)phenyl]-1-propanol Chemical compound CCCCCCCCNC(C)C(O)C1=CC=C(SC(C)C)C=C1 BFCDFTHTSVTWOG-UHFFFAOYSA-N 0.000 title 1
150000003839 salts Chemical class 0.000 claims description 16
ZJNGCHWVIQXKRC-UHFFFAOYSA-N 1-(octylamino)propan-1-ol Chemical compound CCCCCCCCNC(O)CC ZJNGCHWVIQXKRC-UHFFFAOYSA-N 0.000 claims description 15
-1 4-thiophenyl Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 12
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 claims description 8
239000012954 diazonium Substances 0.000 claims description 7
150000001989 diazonium salts Chemical class 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
150000001414 amino alcohols Chemical class 0.000 claims description 4
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims description 3
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 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims 2
XPIXKROOMCBEDW-UHFFFAOYSA-N 2-(octylamino)-1-thiophen-3-ylpropan-1-ol Chemical compound S1C=CC(=C1)C(C(C)NCCCCCCCC)O XPIXKROOMCBEDW-UHFFFAOYSA-N 0.000 claims 1
MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 claims 1
229940100198 alkylating agent Drugs 0.000 claims 1
239000002168 alkylating agent Substances 0.000 claims 1
230000029936 alkylation Effects 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000047 product Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
235000011007 phosphoric acid Nutrition 0.000 description 3
229960004838 phosphoric acid Drugs 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
BFCDFTHTSVTWOG-YLJYHZDGSA-N (1S,2R)-2-(octylamino)-1-[4-(propan-2-ylthio)phenyl]-1-propanol Chemical compound CCCCCCCCN[C@H](C)[C@@H](O)C1=CC=C(SC(C)C)C=C1 BFCDFTHTSVTWOG-YLJYHZDGSA-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 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
229940045803 cuprous chloride Drugs 0.000 description 2
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000011707 mineral Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum 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
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
229960003967 suloctidil Drugs 0.000 description 2
KJIJMJUDCUJVGE-UHFFFAOYSA-N 1-phenyl-2-(4-propan-2-ylthiophen-2-yl)propan-1-one Chemical compound C(C)(C)C=1C=C(SC=1)C(C(=O)C1=CC=CC=C1)C KJIJMJUDCUJVGE-UHFFFAOYSA-N 0.000 description 1
125000000134 2-(methylsulfanyl)ethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])[*] 0.000 description 1
NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
238000004566 IR spectroscopy Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 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
230000005587 bubbling Effects 0.000 description 1
NWEKXBVHVALDOL-UHFFFAOYSA-N butylazanium;hydroxide Chemical compound [OH-].CCCC[NH3+] NWEKXBVHVALDOL-UHFFFAOYSA-N 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 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
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method 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
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
SDQCGKJCBWXRMK-UHFFFAOYSA-N propan-2-yl 4-methylbenzenesulfonate Chemical compound CC(C)OS(=O)(=O)C1=CC=C(C)C=C1 SDQCGKJCBWXRMK-UHFFFAOYSA-N 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
150000003335 secondary amines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000003760 tallow Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters

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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)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

LU83039A 1980-12-24 1980-12-24 Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol LU83039A1 (fr)

Priority Applications (21)

Application Number	Priority Date	Filing Date	Title
LU83039A LU83039A1 (fr)	1980-12-24	1980-12-24	Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol
AT0549881A AT380872B (de)	1980-12-24	1981-12-21	Verfahren zur herstellung von 1-(4-isopropylthiophenyl)-2-n.octyl-amino-propa ol
PT74203A PT74203B (fr)	1980-12-24	1981-12-23	Procedes de synthese du 1-(4-isopropylthiophenyl)-2 n octylami-nopropanol
CH8259/81A CH653325A5 (en)	1980-12-24	1981-12-23	Process for synthesis of 1-(4-isopropylthiophenyl)-2-(n-octylamino)propanol, of its esters and of its salts
ES508313A ES508313A0 (es)	1980-12-24	1981-12-23	"procedimiento para la sintesis de 1-(4-isopropiltiofenil)-2-n.-octilaminopropanol".
AR287941A AR229799A1 (es)	1980-12-24	1981-12-23	Procedimientos para la sintesis del 1-(4-isopropiltiofenil)-2-n-octilaminopropanol
IL64631A IL64631A0 (en)	1980-12-24	1981-12-23	Process for the production of 1-(4-isopropylthiophenyl)-2-n-octylaminopropanol
CH443/85A CH654296A5 (en)	1980-12-24	1981-12-23	Process for the synthesis of 1-(4-isopropylthiophenyl)-2-(n-octylamino)propanol, of its esters and of its salts
KR1019810005129A KR860000340B1 (ko)	1980-12-24	1981-12-24	1-(4-이소프로필티오 페닐)-2-n. 옥틸아미노프로판올의 제조방법.
AU79025/81A AU548084B2 (en)	1980-12-24	1981-12-24	Preparation of 1-(4-isopropylthiophenyl)-2-n-octylamino- propanol
JP56208270A JPS5912665B2 (ja)	1980-12-24	1981-12-24	１−（４−イソプロピルチオフェニル）−２−ｎ−オクチルアミノプロパノ−ル，そのエステル及び塩の合成方法
IT25853/81A IT1140399B (it)	1980-12-24	1981-12-24	Procedimenti di sintesi del 1-(4-isopropiltiofenil)-2-n.ottilamminopropanolo
JP57212827A JPS5915906B2 (ja)	1980-12-24	1982-12-06	１−（４−イソプロピルチオフェニル）２−ｎ−オクチルアミノプロパノ−ル、そのエステル及び塩の製法
JP57212825A JPS5938224B2 (ja)	1980-12-24	1982-12-06	１−（４−イソプロピルチオフェニル）−２−ｎ−オクチルアミノプロパノ−ル、そのエステル及び塩の製法
JP57212826A JPS5915905B2 (ja)	1980-12-24	1982-12-06	１−（４−イソプロピルチオフエニル）−２−ｎ−オクチルアミノプロパノ−ル、そのエステル及び塩の製法
ES522440A ES8407018A1 (es)	1980-12-24	1983-05-16	Procedimiento para la sintesis de 1-4-isopropiltiofenil)-2-n.octilaminopropanol.
ES522442A ES522442A0 (es)	1980-12-24	1983-05-16	Procedimiento para la sintesis de 1-4-isopropiltiofenil-2n.octilaminopropanol.
ES522441A ES522441A0 (es)	1980-12-24	1983-05-16	Procedimiento para la sintesis de 1-4-isopropiltiofenil-2n.octilaminopropanol.
AT416183A AT380873B (de)	1980-12-24	1983-11-28	Verfahren zur herstellung von 1-(4-isopropylthiophenyl)-2-n.octyl-amino -propanol, dessen saeureadditionssalzen und estern
AT257384A AT380874B (de)	1980-12-24	1984-08-08	Verfahren zur herstellung von 1-(4-isopropylthiophenyl)-2-n.octyl-amino-propanol, dessen saeureadditionssalzen und estern
IL74290A IL74290A0 (en)	1980-12-24	1985-02-10	Process for the production of 1-(4-isopropylthiophenyl)2-n-octyl-aminopropanol

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU83039A LU83039A1 (fr)	1980-12-24	1980-12-24	Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol
LU83039		1980-12-24

Publications (1)

Publication Number	Publication Date
LU83039A1 true LU83039A1 (fr)	1982-07-07

Family

ID=19729552

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU83039A LU83039A1 (fr)	1980-12-24	1980-12-24	Procedes de synthese du 1-(4 isopropylthiophenyl)-2-n octylaminopropanol

Country Status (11)

Country	Link
JP (4)	JPS5912665B2 (es)
KR (1)	KR860000340B1 (es)
AR (1)	AR229799A1 (es)
AT (1)	AT380872B (es)
AU (1)	AU548084B2 (es)
CH (2)	CH653325A5 (es)
ES (4)	ES508313A0 (es)
IL (1)	IL64631A0 (es)
IT (1)	IT1140399B (es)
LU (1)	LU83039A1 (es)
PT (1)	PT74203B (es)

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1321701A (en) *	1969-10-01	1973-06-27	Continental Pharma	Amino-alcohols their salts and process for prepairing the same
GB1390748A (en) *	1973-04-09	1975-04-16	Continental Pharma	Alkyl and cycloalkylthiophenylalkylaminoalkanols their salts and the preparation thereof
LU77237A1 (es) *	1977-05-03	1979-01-18
IT1082122B (it) *	1977-07-11	1985-05-21	Medea Res Srl	Processo per la preparazione dell'1-(4-isopropilmercapto-fenil)-2-n.ottilammino-propanolo
LU79970A1 (fr) *	1978-07-13	1980-02-14	Continental Pharma	Procede de preparation de derives de 1-phenyl-1-propanol

1980
- 1980-12-24 LU LU83039A patent/LU83039A1/fr unknown
1981
- 1981-12-21 AT AT0549881A patent/AT380872B/de not_active IP Right Cessation
- 1981-12-23 CH CH8259/81A patent/CH653325A5/fr not_active IP Right Cessation
- 1981-12-23 PT PT74203A patent/PT74203B/pt unknown
- 1981-12-23 AR AR287941A patent/AR229799A1/es active
- 1981-12-23 CH CH443/85A patent/CH654296A5/fr not_active IP Right Cessation
- 1981-12-23 ES ES508313A patent/ES508313A0/es active Granted
- 1981-12-23 IL IL64631A patent/IL64631A0/xx unknown
- 1981-12-24 KR KR1019810005129A patent/KR860000340B1/ko not_active Expired
- 1981-12-24 IT IT25853/81A patent/IT1140399B/it active
- 1981-12-24 JP JP56208270A patent/JPS5912665B2/ja not_active Expired
- 1981-12-24 AU AU79025/81A patent/AU548084B2/en not_active Ceased
1982
- 1982-12-06 JP JP57212825A patent/JPS5938224B2/ja not_active Expired
- 1982-12-06 JP JP57212826A patent/JPS5915905B2/ja not_active Expired
- 1982-12-06 JP JP57212827A patent/JPS5915906B2/ja not_active Expired
1983
- 1983-05-16 ES ES522441A patent/ES522441A0/es active Granted
- 1983-05-16 ES ES522440A patent/ES8407018A1/es not_active Expired
- 1983-05-16 ES ES522442A patent/ES522442A0/es active Granted

Also Published As

Publication number	Publication date
JPS5912665B2 (ja)	1984-03-24
ES8407020A1 (es)	1984-08-16
JPS57134459A (en)	1982-08-19
ATA549881A (de)	1985-12-15
JPS5938224B2 (ja)	1984-09-14
JPS5915906B2 (ja)	1984-04-12
AU548084B2 (en)	1985-11-21
ES522442A0 (es)	1984-08-16
KR830007541A (ko)	1983-10-21
ES8407019A1 (es)	1984-08-16
ES8308844A1 (es)	1983-10-01
IT1140399B (it)	1986-09-24
IL64631A0 (en)	1982-03-31
ES508313A0 (es)	1983-10-01
JPS58113170A (ja)	1983-07-05
JPS58113169A (ja)	1983-07-05
JPS5915905B2 (ja)	1984-04-12
CH654296A5 (en)	1986-02-14
AT380872B (de)	1986-07-25
AR229799A1 (es)	1983-11-30
JPS58113171A (ja)	1983-07-05
PT74203B (fr)	1983-05-20
KR860000340B1 (ko)	1986-04-12
AU7902581A (en)	1982-07-01
PT74203A (fr)	1982-01-01
CH653325A5 (en)	1985-12-31
ES522440A0 (es)	1984-08-16
ES522441A0 (es)	1984-08-16
ES8407018A1 (es)	1984-08-16
IT8125853A0 (it)	1981-12-24

Publication	Publication Date	Title
EP0086678B1 (fr)	1985-07-03	Procédé pour la préparation d'acyl-2 hexahydro-1,3,4,6,7,11b-2H-pyrazino (2,1-a)isoquinoléinones-4 et intermédiaires
JPS6046104B2 (ja)	1985-10-14	ブテン誘導体の製造方法
CH594650A5 (en)	1978-01-13	Antiinflammatory (1,2)-benzothiazine derivs. prepn.
JPS6031824B2 (ja)	1985-07-24	ヒドロキシフェニルピペリジニルメタノ−ル誘導体の製法
BE1000112A5 (fr)	1988-03-29	Procede de preparation d'encainide.
BE569836A (es)
EP0008962B1 (fr)	1983-02-09	Nouveaux dérivés de la ((quinolyl-4)-3 propyl-1)-4 pipéridine et médicaments les contenant
CH654296A5 (en)	1986-02-14	Process for the synthesis of 1-(4-isopropylthiophenyl)-2-(n-octylamino)propanol, of its esters and of its salts
FR2473512A1 (fr)	1981-07-17	Nouveaux 2-aminomethyl-6-halogeno-phenols, leur preparation et leur application comme medicaments
FR2466450A1 (fr)	1981-04-10	Procede industriel de purification et d'obtention d'itanoxone de qualite pharmaceutique
FR2494696A1 (fr)	1982-05-28	Nouveau procede de preparation de steroides 3-amines et leurs sels
JPS59110658A (ja)	1984-06-26	フエニルエタノ−ルアミン類の製法
EP0837843B1 (fr)	2001-09-12	Procede de preparation des formes enantiomeres de l'acide amino alkylaminophenyl propanoique
JPS62223157A (ja)	1987-10-01	ニトロン類の製造方法
EP1409457A1 (fr)	2004-04-21	Procede pour la preparation de la 4-methylamino-4-phenylpiperidine
BE562169A (es)
BE525505A (es)
BE561617A (es)
BE580872A (es)
CH465619A (fr)	1968-11-30	Procédé pour la préparation d'un sel d'acide d'un dérivé de l'acide barbiturique
BE515645A (es)
BE474887A (es)
BE569079A (es)
CH321872A (fr)	1957-05-31	Procédé de préparation d'halogéno-2-amino-2'-diphénylsulfures
BE568492A (es)