CS203006B2 - Způsob výroby nových derivátů alkylendiaminu - Google Patents
Způsob výroby nových derivátů alkylendiaminu Download PDFInfo
- Publication number
- CS203006B2 CS203006B2 CS797081A CS708179A CS203006B2 CS 203006 B2 CS203006 B2 CS 203006B2 CS 797081 A CS797081 A CS 797081A CS 708179 A CS708179 A CS 708179A CS 203006 B2 CS203006 B2 CS 203006B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- compound
- carbon atoms
- acid
- starting material
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 bromo, hydroxy Chemical group 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 239000007858 starting material Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 9
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 2
- 229940125782 compound 2 Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 5
- 229940039009 isoproterenol Drugs 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- VATQPUHLFQHDBD-UHFFFAOYSA-N 6-chloro-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(Cl)=CC(=O)N(C)C1=O VATQPUHLFQHDBD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 4
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000126 substance Substances 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- JQQXAMIFWQJQEA-UHFFFAOYSA-N 1-(2-aminoethylamino)-3-phenoxypropan-2-ol Chemical compound NCCNCC(O)COC1=CC=CC=C1 JQQXAMIFWQJQEA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
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- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 210000001105 femoral artery Anatomy 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
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- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
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- 230000001629 suppression Effects 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 description 1
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Claims (14)
1. Způsob výroby nových derivátů alkylendiaminu vzorce I
O
CH2-NH-(CH2)n- NH (I) v němž
R, a Rg znamenají nezávisle na sobě vodík, fluor, chlor, brom, hydroxyskupinu, trifluormethylovou skupinu, nitroskupinu, fenylovou skupinu, alkylovou skupinu s 1 až 8 atomy uhlíku, alkenylovou skupinu s až 6 atomy uhlíku, alkinylovou skupinu s až 6 atomy uhlíku, cykloalkylovou skupinu s 5 až 8 atomy uhlíku v kruhu, cykloalkenylovou skupinu s 5 až 8 atomy uhlíku v kruhu, alkoxyskupinu s 1 až 8 atomy uhlíku, cykloalkoxyskupinu s 5 eí 8 atomy uhlíku v kruhu, alkenyloxyskupinu s až 6 atomy uhlíku, alkinyloxysKupinu s až 6 atomy uhlíku, fenethyloxyskupinu, benzyloxyskupinu, alkanoylovou skupinu s 1 až 6 atomy uhlíku, alkoxyalkoxyskupinu s celkem až
15 203006
8 atomy uhlíku, alkoxyalkylovou skupinu se 2 až 6 atomy uhlíku, hydroxyaikoxyskupinu se 2 až 6 atomy uhlíku, zbytek -NH-CO-Rg, přičemž
Rg znamená morfolinoskupinu, piperidinoskupinu nebo 1-pyrrolidinylovou skupinu, acylaminoskupinu s až 11 atomy uhlíku v acylovém zbytku, ureidoskupinu, ureidoskupinu, která je v poloze 3 monosubstituována cykloalkylovou skupinou s 5 nebo 6 atomy uhlíku, ureidoskupinu, která je v poloze 3 mono- nebo disubstituována alkylovou skupinou s 1 až 6 atomy uhlíku nebo/a alkenylovou skupinou se 3 až 6 atomy uhlíku,
Rj znamená vodík nebo alkylovou skupinu s 1 až 4 atomy uhlíku a n znamená číslo 2 nebo 3, a jejioh adičních solí s kyselinami, vyznačující se tím, že se na sloučeninu obecného vzorce VI
N-R, (VI)
Hal v němž
Rj má shora uvedený význam a Hal znamená halogen, působí sloučeninou obecného vzorce IX
O—CH2—CH—CH2—NH—(CH2)n—NH2 R2 OH v němž
R,, Rg a n mají shora uvedené významy, a takto získaná sloučenina se popřípadě převede na ediční sůl s kyselinou působením kyseliny.
2. Způsob podle bodu 1 k výrobě sloučenin obecného vzorce I, v němž
R1 nebo Rg znamenají vodík, fluor, chlor, brom, triřluormethylovou skupinu, nitroskupinu, fenylovou skupinu, alkylovou skupinu s 1 až 8 atomy uhlíku, alkenylovou skupinu s až 6 atomy uhlíku, alkinylovou skupinu s až 6 atomy uhlíku, cykloalkylovou skupinu, s 5 až 8 atomy uhlíku v kruhu, cykloalkenylovou skupinu s 5 až 8 atomy uhlíku v kruhu, alkoxyskupinu s 1 až 8 atomy uhlíku, cykloalkoxyskupinu s 5 až 8 atomy uhlíku v kruhu, alkenyloxyskupinu s až 6 atomy uhlíku, alkinyloxyskupinu s až 6 atomy uhlíku, fenethyloxyskupinu, benzyloxyskupinu, alkanoylovou skupinu s 1 až 6 atoqy uhlíku, alkoxyalkoxyskupinu s celkem až 8 atomy uhlíku, alkoxyalkylovou skupinu se 2 až 6 atomy uhlíku, hydroxyalkoxyskupinu se 2 až 6 atomy uhlíku, acylaminoskupinu s až 11 atomy uhlíku v acylovém zbytku, ureidoskupinu, ureidoskupinu, která je v poloze 3 monosubstituována cykloalkylovou skupinou s 5 nebo 6 atomy uhlíku, ureidoskupinu, která je v poloze 3 mono- nebo disubstituována alkylovou skupinou s 1 až 6 atomy uhlíku nebo/a alkenylovou skupinou se 3 až 6 atomy uhlíku, β Rj a n mají význam uvedený v bodě 1 a jejich adiční solí s kyselinami, vyznačující se tím, že se na sloučeninu obecného vzorce VI
O n-r3 (VI)
Hal 0 r3 v němž
Rj má shora uvedený význam a
Hal znamená halogen, působí sloučeninou obecného vzorce IX (IX)
O-CH2-CH-CH2—NH—(CH2|n- nh2 fí, OH v němž
Rj i Rg a n mají shora uvedené významy, a takto získaná sloučenina se popřípadě převede na ediční sůl s kyselinou působením kyseliny.
3. Způsob podle bodu čeniny obecného vzorce IX, dě 1 .
4. Způsob podle bodu 2, vyznačující se čeniny obecného vzorce IX, v němž n znamená dě 2.
1, vyznačující se tím, že se jako výchozí látky používá slouv němž n znamená číslo 2 a R, a Rg mají významy uvedené v botím, že se jako výchozí látky používá sloučíslo 2 a Rj a Rg mají významy uvedené v bo
5. Způsob podle bodu 1, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce IX, v němž jeden ze substituentů R, nebo Rg má jiný význam než vodík a je v p-poloze fenylového jádře a n má význam uvedený v bodě 1.
6. Způsob podle bodu 2, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce IX, v němž jeden ze substituentů R, a Rg má jiný význam než vodík a je v p-poloze fenylového jádra a n má význam uvedený v bodě 2.
•
7. Způsob podle bodu 1, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce VI, v němž Rj znamená methylovou skupinu a Hal má význam uvedený v bodě 1.
8. Způsob podle bodů 1 a 2, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce IX, v němž R, nebo Rg znamená alkoxyalkoxyskupinu s celkem až 8 atomy uhlíku a n má význam uvedený v bodě I.
9. Způsob podle bodů 1 a 2, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce IX, v němž R, nebo Rg znamená alkoxyalkylovou skupinu se
2 až 6 atomy uhlíku a n má význam uvedený v bodě 1.
10. Způsob podle bodů 1 a 2, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce IX, v němž R^ nebo Rg znamená hydroxyalkoxyskupinu se 2 až 6
Π atomy uhlíku a n má význam uvedený v bodě 1.
.
11. Způsob podle bodů 1 nebo 2, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce IX, v němž R, nebo Rg znamená alkoxyskupinu s 1 až 8 atomy uhlíku a n má význam uvedený v bodě 1.
12. Způsob podle bodu 1, vyznačující se tím, že se jako výchozí látky používá sloučeniny obecného vzorce IX, v němž R, nebo Rg znamená hydroxylovou skupinu a n má význam uvedený v bodě 1.
13. Způsob podle bodu 1, vyznačující se tím, že se jako výchozích látek používá sloučenin obecných vzorců VI a IX, v nichž R-j znamená methylovou skupinu, n znamená číslo 2, R, znamená vodík a Rg znamená skupinu H0-, CH^O-, CgH^CHgO-, CgH^CHgCHgO-, CgH^CHgCHgCHgO-, CgH^CHg-O-CHg-CHg-O-, HO-CHgCHg-Ο-, CgHjCHgO- nebo GgHjO-CHg- v para-poloze fenylového jádra a Hal a n mají významy uvedené v bodě 1.
14. Způsob podle bodu 2, vyznačující se tim, že se jako výchozích látek používásloučenin obecných vzorců VI a IX, v nichž R^ znamená methylovou skupinu, n znamená číslo 2, R, znamená vodík a Rg znamená skupinu CH^O-, CgH^CHgO-, CgH^CHgCHg-O-, CgH^HgCHgCHgO-, CgHjCHg-O-CHgCHgO-, HO-CHgCHg-O-, CgH^HgO- nebo CgHjO-CHg- v para-poloze fenylového jádra a Hal a n mají významy uvedené v bodě 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS797081A CS203006B2 (cs) | 1977-05-16 | 1979-10-18 | Způsob výroby nových derivátů alkylendiaminu |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU77339A LU77339A1 (cs) | 1977-05-16 | 1977-05-16 | |
| CS783148A CS203005B2 (en) | 1977-05-16 | 1978-05-16 | Process for preparing new derivatives of alkylendiamine |
| CS797081A CS203006B2 (cs) | 1977-05-16 | 1979-10-18 | Způsob výroby nových derivátů alkylendiaminu |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203006B2 true CS203006B2 (cs) | 1981-02-27 |
Family
ID=25745759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS797081A CS203006B2 (cs) | 1977-05-16 | 1979-10-18 | Způsob výroby nových derivátů alkylendiaminu |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS203006B2 (cs) |
-
1979
- 1979-10-18 CS CS797081A patent/CS203006B2/cs unknown
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