DD202709A5 - Verfahren zur herstellung von beta-cyclo-substituierten ethylaminen - Google Patents

Verfahren zur herstellung von beta-cyclo-substituierten ethylaminen Download PDF

Info

Publication number: DD202709A5
Authority: DD; German Democratic Republic
Prior art keywords: ppm; formula; item; derivative; compound
Prior art date: 1981-06-30

Application number

DD82241197A

Other languages

German (de)

English (en)

Inventor

Isaac Chekroun

Alain Heymes

Original Assignee

Sanofi Sa

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.)

1981-06-30

Filing date

1982-06-29

Publication date

1983-09-28

1982-06-29 Application filed by Sanofi Sa filed Critical Sanofi Sa

1983-09-28 Publication of DD202709A5 publication Critical patent/DD202709A5/de

Links

238000000034 method Methods 0.000 title claims description 35
238000004519 manufacturing process Methods 0.000 title abstract description 4
150000003947 ethylamines Chemical class 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 22
-1 furfuryl Chemical group 0.000 claims abstract description 17
239000002253 acid Substances 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
239000003638 chemical reducing agent Substances 0.000 claims abstract description 3
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000001544 thienyl group Chemical group 0.000 claims abstract description 3
150000001728 carbonyl compounds Chemical class 0.000 claims abstract 2
125000004438 haloalkoxy group Chemical group 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
239000012279 sodium borohydride Substances 0.000 claims description 9
229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
239000002585 base Substances 0.000 claims description 8
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 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
239000011734 sodium Substances 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
150000004292 cyclic ethers Chemical class 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
239000008096 xylene Substances 0.000 claims description 3
239000003513 alkali Substances 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims 2
150000001342 alkaline earth metals Chemical class 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract 1
125000001624 naphthyl group Chemical group 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
239000003921 oil Substances 0.000 description 22
235000019198 oils Nutrition 0.000 description 22
239000000047 product Substances 0.000 description 22
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
229910000041 hydrogen chloride Inorganic materials 0.000 description 21
239000000243 solution Substances 0.000 description 21
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000012071 phase Substances 0.000 description 12
239000013078 crystal Substances 0.000 description 11
PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 11
150000002466 imines Chemical class 0.000 description 10
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
UIBCDEFKKLRXHR-UHFFFAOYSA-N diethoxyphosphorylmethanamine Chemical compound CCOP(=O)(CN)OCC UIBCDEFKKLRXHR-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
PCWVTWTWXYEUBO-UHFFFAOYSA-N ethenoxyphosphonamidic acid Chemical compound NP(O)(=O)OC=C PCWVTWTWXYEUBO-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 3
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical compound Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
239000011707 mineral Substances 0.000 description 3
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
235000019502 Orange oil Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
239000010502 orange oil Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
150000002903 organophosphorus compounds Chemical class 0.000 description 2
ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
QHFPHCIRIQQPDI-UHFFFAOYSA-N (ethenylamino)phosphonic acid Chemical compound OP(O)(=O)NC=C QHFPHCIRIQQPDI-UHFFFAOYSA-N 0.000 description 1
SWFKPUQRJHGZGE-UHFFFAOYSA-N 1-(4-ethoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.CCOC1=CC=C(C(C)N)C=C1 SWFKPUQRJHGZGE-UHFFFAOYSA-N 0.000 description 1
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-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
IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
235000008694 Humulus lupulus Nutrition 0.000 description 1
244000025221 Humulus lupulus Species 0.000 description 1
UANNSXMPNZFKGN-UHFFFAOYSA-N O=CC1=CC=C[S+]1Br Chemical compound O=CC1=CC=C[S+]1Br UANNSXMPNZFKGN-UHFFFAOYSA-N 0.000 description 1
NVHKBSKYGPFWOE-YADHBBJMSA-N PS-PS Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCC(O)=O NVHKBSKYGPFWOE-YADHBBJMSA-N 0.000 description 1
102100030624 Proton myo-inositol cotransporter Human genes 0.000 description 1
108091006309 SLC2A13 Proteins 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
FJKFUXNMDLMIRM-UHFFFAOYSA-N aminooxy(methyl)phosphinic acid Chemical compound CP(O)(=O)ON FJKFUXNMDLMIRM-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000010908 decantation Methods 0.000 description 1
YTAOPBOXQQWKJD-UHFFFAOYSA-N di(propan-2-yloxy)phosphorylmethanamine Chemical compound CC(C)OP(=O)(CN)OC(C)C YTAOPBOXQQWKJD-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
QZJYHWXRWTVKSH-UHFFFAOYSA-N ethylaminomethylphosphonic acid Chemical compound CCNCP(O)(O)=O QZJYHWXRWTVKSH-UHFFFAOYSA-N 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000010354 integration Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
OTIDWUALRXXVIM-UHFFFAOYSA-N n-ethylpyridin-4-amine Chemical compound CCNC1=CC=NC=C1 OTIDWUALRXXVIM-UHFFFAOYSA-N 0.000 description 1
BYGZVEKTHREAGM-UHFFFAOYSA-N n-ethylthiophen-2-amine Chemical compound CCNC1=CC=CS1 BYGZVEKTHREAGM-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000005541 phosphonamide group Chemical group 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
CGRKYEALWSRNJS-UHFFFAOYSA-N sodium;2-methylbutan-2-olate Chemical compound [Na+].CCC(C)(C)[O-] CGRKYEALWSRNJS-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2462—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of unsaturated acyclic amines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2475—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aralkylamines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)

DD82241197A 1981-06-30 1982-06-29 Verfahren zur herstellung von beta-cyclo-substituierten ethylaminen DD202709A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8113065A FR2508442A1 (fr)	1981-06-30	1981-06-30	Procede de preparation d'ethylamines b-cyclo-substituees et produits ainsi obtenus

Publications (1)

Publication Number	Publication Date
DD202709A5 true DD202709A5 (de)	1983-09-28

Family

ID=9260132

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD82241197A DD202709A5 (de)	1981-06-30	1982-06-29	Verfahren zur herstellung von beta-cyclo-substituierten ethylaminen

Country Status (25)

Country	Link
US (1)	US4493931A (cs)
EP (1)	EP0069622B1 (cs)
JP (1)	JPS5813547A (cs)
KR (1)	KR840000524A (cs)
AR (1)	AR231433A1 (cs)
AT (1)	ATE15650T1 (cs)
AU (1)	AU567282B2 (cs)
CA (1)	CA1184918A (cs)
CS (1)	CS238628B2 (cs)
DD (1)	DD202709A5 (cs)
DE (1)	DE3266363D1 (cs)
DK (1)	DK294682A (cs)
ES (1)	ES8305303A1 (cs)
FI (1)	FI71550C (cs)
FR (1)	FR2508442A1 (cs)
GR (1)	GR77204B (cs)
HU (1)	HU189597B (cs)
IE (1)	IE53257B1 (cs)
IL (1)	IL65983A (cs)
NO (1)	NO153133C (cs)
NZ (1)	NZ200855A (cs)
PT (1)	PT75155B (cs)
SU (1)	SU1147249A3 (cs)
YU (1)	YU143182A (cs)
ZA (1)	ZA824617B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3839049B2 (ja) *	1994-06-03	2006-11-01	テムドトラスト	メタ位置換のアリルアルキルアミン類ならびに治療および診断のためのその使用
WO2000006176A1 (en) *	1998-07-31	2000-02-10	Eli Lilly And Company	Amidophosphate derivatives
SG169238A1 (en) *	2004-08-11	2011-03-30	Williamsburg Holdings Llc	Noncardiotoxic pharmaceutical compounds

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2983729A (en) *	1958-04-30	1961-05-09	Monsanto Chemicals	Preparation of 5-halothienyl amines
FR2345150A2 (fr) *	1975-08-06	1977-10-21	Centre Etd Ind Pharma	Nouveaux derives de la thienopyridine, et leur application
FR2215948B1 (cs) *	1973-02-01	1976-05-14	Centre Etd Ind Pharma

1981
- 1981-06-30 FR FR8113065A patent/FR2508442A1/fr active Granted
1982
- 1982-06-01 IE IE1313/82A patent/IE53257B1/en unknown
- 1982-06-04 NZ NZ200855A patent/NZ200855A/en unknown
- 1982-06-06 IL IL65983A patent/IL65983A/xx unknown
- 1982-06-08 AR AR289629A patent/AR231433A1/es active
- 1982-06-09 ES ES514101A patent/ES8305303A1/es not_active Expired
- 1982-06-09 GR GR68377A patent/GR77204B/el unknown
- 1982-06-10 AU AU84751/82A patent/AU567282B2/en not_active Ceased
- 1982-06-18 EP EP82401118A patent/EP0069622B1/fr not_active Expired
- 1982-06-18 AT AT82401118T patent/ATE15650T1/de not_active IP Right Cessation
- 1982-06-18 DE DE8282401118T patent/DE3266363D1/de not_active Expired
- 1982-06-25 SU SU823457190A patent/SU1147249A3/ru active
- 1982-06-29 FI FI822314A patent/FI71550C/fi not_active IP Right Cessation
- 1982-06-29 DD DD82241197A patent/DD202709A5/de unknown
- 1982-06-29 CA CA000406278A patent/CA1184918A/en not_active Expired
- 1982-06-29 ZA ZA824617A patent/ZA824617B/xx unknown
- 1982-06-29 CS CS824900A patent/CS238628B2/cs unknown
- 1982-06-29 HU HU822111A patent/HU189597B/hu unknown
- 1982-06-29 US US06/393,383 patent/US4493931A/en not_active Expired - Fee Related
- 1982-06-29 NO NO822227A patent/NO153133C/no unknown
- 1982-06-29 PT PT75155A patent/PT75155B/pt not_active IP Right Cessation
- 1982-06-30 JP JP57113841A patent/JPS5813547A/ja active Pending
- 1982-06-30 KR KR1019820002915A patent/KR840000524A/ko unknown
- 1982-06-30 YU YU01431/82A patent/YU143182A/xx unknown
- 1982-06-30 DK DK294682A patent/DK294682A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO153133B (no)	1985-10-14
FI822314A0 (fi)	1982-06-29
IE53257B1 (en)	1988-09-28
PT75155A (fr)	1982-07-01
NO153133C (no)	1986-01-22
YU143182A (en)	1985-03-20
ES514101A0 (es)	1983-04-01
FI822314L (fi)	1982-12-31
CS238628B2 (en)	1985-12-16
ES8305303A1 (es)	1983-04-01
DE3266363D1 (en)	1985-10-24
AR231433A1 (es)	1984-11-30
FR2508442B1 (cs)	1984-03-09
EP0069622B1 (fr)	1985-09-18
JPS5813547A (ja)	1983-01-26
SU1147249A3 (ru)	1985-03-23
NZ200855A (en)	1985-08-30
FI71550C (fi)	1987-01-19
AU8475182A (en)	1983-01-06
KR840000524A (ko)	1984-02-25
IL65983A (en)	1985-06-30
ZA824617B (en)	1983-04-27
EP0069622A1 (fr)	1983-01-12
ATE15650T1 (de)	1985-10-15
IE821313L (en)	1982-12-30
AU567282B2 (en)	1987-11-19
FR2508442A1 (fr)	1982-12-31
FI71550B (fi)	1986-10-10
CA1184918A (en)	1985-04-02
GR77204B (cs)	1984-09-11
DK294682A (da)	1982-12-31
NO822227L (no)	1983-01-03
US4493931A (en)	1985-01-15
HU189597B (en)	1986-07-28
PT75155B (fr)	1984-05-29
IL65983A0 (en)	1982-09-30

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IL275584B2 (en)	2023-08-01	A process for separating a serial mixture of nicotine
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DE112011104615B4 (de)	2022-04-28	Organoborverbindung und Verfahren zum Herstellen derselben
DD156369A5 (de)	1982-08-18	Herstellung von rechtsdrehenden 5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3b]-indolen
DE3147977A1 (de)	1982-08-05	Neue organische verbindungen, verfahren zu ihrer herstellung und ihre verwendung
DD202709A5 (de)	1983-09-28	Verfahren zur herstellung von beta-cyclo-substituierten ethylaminen
SU1148563A3 (ru)	1985-03-30	Способ получени производных 2-(тиенил-2)- или 2-(тиенил-3) этиламина
CH417574A (de)	1966-07-31	Verfahren zur Herstellung therapeutisch wirksamer Dibenzocycloheptanderivate
EP0222163B1 (de)	1989-07-19	Verfahren zur Herstellung von gamma-Butyrolactamen
DD202712A5 (de)	1983-09-28	Verfahren zur herstellung von (thienyl-2)-und (thienyl-3)-2-aethylaminderivaten
DD143768A5 (de)	1980-09-10	Verfahren zur herstellung von pyrrolidon-verbindungen
DD243491A5 (de)	1987-03-04	Verfahren zur herstellung neuer 3-phenyl-2-propanamin-derivate
EP0391850B1 (de)	1994-09-28	Ungesättigte Aminodicarbonsäurederivate
DD202710A5 (de)	1983-09-28	Verfahren zur herstellung von (thienyl-2)- und (thienyl-3)-2-aethylamin-derivaten
DE3779525T2 (de)	1993-02-11	5-aminomethyl-2-oxazolidinon-derivate, ihre herstellung und ihre anwendung in der heilkunde.
DE3301198A1 (de)	1984-07-19	N-arylalkylamin-3-propoxypyridin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische praeparate und deren verwendung
AT395852B (de)	1993-03-25	Imidazolyl-methyl-tetrahydrothiophenderivate
EP0420806A1 (de)	1991-04-03	Phosphonsäure, Verfahren zur Herstellung und Verwendung als Arzneimittelwirkstoff
EP0005186B1 (de)	1981-12-30	3-Alkyl-5-(2-hydroxy-styryl)-isoxazole und Verfahren zu ihrer Herstellung
AT371445B (de)	1983-06-27	Verfahren zur herstellung von neuen cis-4a-phenyl-isochinolinderivaten und ihren saeureadditionssalzen
WO1995000522A1 (de)	1995-01-05	Phosphonobernsteinsäurederivate und ihre verwendung als arzneimittel
AT242145B (de)	1965-08-25	Verfahren zur Herstellung neuer Phenthiazinverbindungen