CA1040647A - Derives de amino-3 prop-1-enes - Google Patents

Derives de amino-3 prop-1-enes

Info

Publication number: CA1040647A
Authority: CA; Canada
Prior art keywords: group; formula; biphenylyl; reacting; represent
Prior art date: 1971-12-29
Legal status (The legal status 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 status listed.): Expired

Application number

CA258,457A

Other languages

English (en)

Inventor

Paul A. Barrett

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wellcome Foundation Ltd

Original Assignee

Wellcome Foundation Ltd

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.)

1971-12-29

Filing date

1976-08-05

Publication date

1978-10-17

1971-12-29 Priority claimed from GB1516973A external-priority patent/GB1434714A/en

1972-12-29 Priority claimed from CA160,202A external-priority patent/CA1009255A/en

1976-08-05 Application filed by Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd

1978-10-17 Application granted granted Critical

1978-10-17 Publication of CA1040647A publication Critical patent/CA1040647A/fr

Status Expired legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title abstract description 5
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 title abstract description 4
238000000034 method Methods 0.000 claims abstract description 53
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 38
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
125000002560 nitrile group Chemical group 0.000 claims abstract description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims abstract description 9
125000001246 bromo group Chemical group Br* 0.000 claims abstract description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
150000001875 compounds Chemical class 0.000 claims description 47
-1 biphenylyl Chemical group 0.000 claims description 39
239000000126 substance Substances 0.000 claims description 14
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
150000002576 ketones Chemical class 0.000 claims description 10
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 7
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
125000002524 organometallic group Chemical group 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
150000002825 nitriles Chemical class 0.000 claims description 5
GWCOIQVXNDGKAH-UHFFFAOYSA-N 3,3-bis(4-phenylphenyl)prop-2-en-1-amine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CCN)C(C=C1)=CC=C1C1=CC=CC=C1 GWCOIQVXNDGKAH-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
LRKPTMSTRKPDSJ-UHFFFAOYSA-N 3,3-bis(4-phenylphenyl)prop-2-enenitrile Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CC#N)C(C=C1)=CC=C1C1=CC=CC=C1 LRKPTMSTRKPDSJ-UHFFFAOYSA-N 0.000 claims description 3
FAZCGYMPLKBOHR-UHFFFAOYSA-N 3-(methylamino)-1,1-bis(4-phenylphenyl)propan-1-ol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(O)(CCNC)C(C=C1)=CC=C1C1=CC=CC=C1 FAZCGYMPLKBOHR-UHFFFAOYSA-N 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
QRQHCGWCUVLPSQ-UHFFFAOYSA-N bis(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QRQHCGWCUVLPSQ-UHFFFAOYSA-N 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
235000019253 formic acid Nutrition 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
UDGMOTUYRVNJLX-UHFFFAOYSA-N n-[3,3-bis(4-phenylphenyl)prop-2-enyl]acetamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CCNC(=O)C)C(C=C1)=CC=C1C1=CC=CC=C1 UDGMOTUYRVNJLX-UHFFFAOYSA-N 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
SHIZMRZYZKNFRJ-UHFFFAOYSA-N 1-phenyl-4-[1-(4-phenylphenyl)prop-1-enyl]benzene Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CC)C(C=C1)=CC=C1C1=CC=CC=C1 SHIZMRZYZKNFRJ-UHFFFAOYSA-N 0.000 claims description 2
JTCGOCKXVDDQAO-UHFFFAOYSA-N 2-bis(ethylperoxy)phosphorylacetonitrile Chemical compound CCOOP(=O)(CC#N)OOCC JTCGOCKXVDDQAO-UHFFFAOYSA-N 0.000 claims description 2
SPNSSEKVTXYNNH-UHFFFAOYSA-N 2-diethoxyphosphoryl-n,n-dimethylacetamide Chemical compound CCOP(=O)(OCC)CC(=O)N(C)C SPNSSEKVTXYNNH-UHFFFAOYSA-N 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
229910052744 lithium Chemical group 0.000 claims description 2
229910052987 metal hydride Inorganic materials 0.000 claims description 2
150000004681 metal hydrides Chemical class 0.000 claims description 2
ZPUQTLXTOCXEOM-UHFFFAOYSA-N 3-(dimethylamino)-1,1-bis(4-phenylphenyl)propan-1-ol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(O)(CCN(C)C)C(C=C1)=CC=C1C1=CC=CC=C1 ZPUQTLXTOCXEOM-UHFFFAOYSA-N 0.000 claims 2
NACCJOIEZISYCU-UHFFFAOYSA-M [Br-].C1=CC([Mg+])=CC=C1C1=CC=CC=C1 Chemical compound [Br-].C1=CC([Mg+])=CC=C1C1=CC=CC=C1 NACCJOIEZISYCU-UHFFFAOYSA-M 0.000 claims 2
DQXWERLLLZTRHC-UHFFFAOYSA-N 1-[3-bromo-1-(4-phenylphenyl)prop-1-enyl]-4-phenylbenzene Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CCBr)C(C=C1)=CC=C1C1=CC=CC=C1 DQXWERLLLZTRHC-UHFFFAOYSA-N 0.000 claims 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims 1
208000015181 infectious disease Diseases 0.000 abstract description 5
238000002360 preparation method Methods 0.000 abstract description 5
206010001935 American trypanosomiasis Diseases 0.000 abstract description 4
208000024699 Chagas disease Diseases 0.000 abstract description 3
230000000654 trypanocidal effect Effects 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
230000000875 corresponding effect Effects 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000012280 lithium aluminium hydride Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
241000223109 Trypanosoma cruzi Species 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
MCNHYLBWENGSSD-UHFFFAOYSA-N n,n-dimethyl-3,3-bis(4-phenylphenyl)prop-2-en-1-amine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CCN(C)C)C(C=C1)=CC=C1C1=CC=CC=C1 MCNHYLBWENGSSD-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
239000008213 purified water Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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 2
241000699670 Mus sp. Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
DVQMPWOLBFKUMM-UHFFFAOYSA-N 2-diethoxyphosphorylacetic acid Chemical compound CCOP(=O)(CC(O)=O)OCC DVQMPWOLBFKUMM-UHFFFAOYSA-N 0.000 description 1
HVLXNBUJUZAEPC-UHFFFAOYSA-N 3-(dimethylamino)-1,1-bis(4-phenylphenyl)propan-1-ol hydrobromide Chemical compound Br.C=1C=C(C=2C=CC=CC=2)C=CC=1C(O)(CCN(C)C)C(C=C1)=CC=C1C1=CC=CC=C1 HVLXNBUJUZAEPC-UHFFFAOYSA-N 0.000 description 1
VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenylpropanol Natural products OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
SLGOMQZXBQIFQX-UHFFFAOYSA-N 3-amino-1,1-bis(4-phenylphenyl)propan-1-ol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(O)(CCN)C(C=C1)=CC=C1C1=CC=CC=C1 SLGOMQZXBQIFQX-UHFFFAOYSA-N 0.000 description 1
MPIIANWUYKKPSQ-UHFFFAOYSA-N 3-amino-1-(4-chlorophenyl)-1-[4-(4-chlorophenyl)phenyl]propan-1-ol Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(O)(CCN)C1=CC=C(Cl)C=C1 MPIIANWUYKKPSQ-UHFFFAOYSA-N 0.000 description 1
ZVZUSFDNDBXDHU-UHFFFAOYSA-N 3-hydroxy-3,3-bis(4-phenylphenyl)propanenitrile Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(CC#N)(O)C(C=C1)=CC=C1C1=CC=CC=C1 ZVZUSFDNDBXDHU-UHFFFAOYSA-N 0.000 description 1
TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XZAGANKBCHPKGM-UHFFFAOYSA-N Cl.C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CCN)C(C=C1)=CC=C1C1=CC=CC=C1 Chemical compound Cl.C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CCN)C(C=C1)=CC=C1C1=CC=CC=C1 XZAGANKBCHPKGM-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
101100134929 Gallus gallus COR9 gene Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
235000000903 Ranunculus bulbosus Nutrition 0.000 description 1
240000005608 Ranunculus bulbosus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000006267 biphenyl group Chemical group 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
229910052799 carbon Inorganic materials 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
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
LZBIYPIDWSGLOV-UHFFFAOYSA-N dimethyl(prop-2-enyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC=C LZBIYPIDWSGLOV-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
239000007902 hard capsule Substances 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000011812 mixed powder Substances 0.000 description 1
NXBBFAKHXAMPOM-UHFFFAOYSA-N n,n-dimethylprop-1-en-1-amine Chemical compound CC=CN(C)C NXBBFAKHXAMPOM-UHFFFAOYSA-N 0.000 description 1
GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 description 1
BHDDRKFEUGWIGZ-UHFFFAOYSA-N n-methyl-3,3-bis(4-phenylphenyl)prop-2-en-1-amine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=CCNC)C(C=C1)=CC=C1C1=CC=CC=C1 BHDDRKFEUGWIGZ-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA258,457A 1971-12-29 1976-08-05 Derives de amino-3 prop-1-enes Expired CA1040647A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB1516973A GB1434714A (en)	1971-12-29	1971-12-29	3-amino-prop-1-enes methods for their preparation
GB4874872		1972-10-23
CA160,202A CA1009255A (en)	1971-12-29	1972-12-29	3-amino-prop-1-enes and the preparation thereof

Publications (1)

Publication Number	Publication Date
CA1040647A true CA1040647A (fr)	1978-10-17

Family

ID=27162513

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA258,457A Expired CA1040647A (fr)	1971-12-29	1976-08-05	Derives de amino-3 prop-1-enes

Country Status (1)

Country	Link
CA (1)	CA1040647A (fr)

1976
- 1976-08-05 CA CA258,457A patent/CA1040647A/fr not_active Expired

Publication	Publication Date	Title
EP1497274B1 (fr)	2006-09-13	Derives de terphenyle, leur preparation, les compositions pharmaceutiques en contenant
US5464872A (en)	1995-11-07	Arylalkyl (thio) amides
US6849649B2 (en)	2005-02-01	N-phenpropylcyclopentyl-substituted glutaramide derivatives as inhibitors of neutral endopeptidase
US4423044A (en)	1983-12-27	3,4-Dihydro-5H-2,3-benzodiazepine derivatives and pharmaceutical use thereof
NZ527012A (en)	2005-03-24	N-phenpropylcyclopentyl-substituted glutaramide derivatives as NEP inhibitors for FSAD
FR2838438A1 (fr)	2003-10-17	Derives de diphenylpyridine,leur preparation, les compositions pharmaceutiques en contenant
JPS63190857A (ja)	1988-08-08	８−置換２−アミノテトラリン類
CS258149B2 (en)	1988-07-15	Method of arylcyclobutylalkylamines production
US3957850A (en)	1976-05-18	Phenylacetic acid derivatives
JPH0527634B2 (fr)	1993-04-21
CA1040647A (fr)	1978-10-17	Derives de amino-3 prop-1-enes
EP0230020B1 (fr)	1990-09-19	1,2,3,4,4a,9b-Hexahydro-4a-aminoalkyldibenzofurannes, procédé pour leur préparation et leur utilisation comme médicaments
US3562276A (en)	1971-02-09	Diarylcyclopropane piperazides possessing enhanced antihistaminic,antiserotoninic and antiexudative activity
US3213138A (en)	1965-10-19	N, n-disubstituted-n'-phenylalkyl hydrazines
IE66161B1 (en)	1995-12-13	New imidazole compounds process for the preparation thereof and pharmaceutical compositions containing them
US3997608A (en)	1976-12-14	N-substituted-dihydroxyphenethylamines
US3932663A (en)	1976-01-13	Certain 3-amino-prop-1-enes for treating Trypanosoma cruzi infections
FR2887548A1 (fr)	2006-12-29	Derives de 4,5-diarylpyrrole, leur preparation et leur application en therapeutique
US4511566A (en)	1985-04-16	2-N-Cycloalkylmethyl 3-oxo 5,6-diaryl-as-triazines
US4101579A (en)	1978-07-18	Phenethanolamine ethers
GB2051796A (en)	1981-01-21	(3 - alkylamino - 2 - hydroxypropoxy)-furan - 2 - carboxylic acid anilides and physiologically tolerated acid addition salts thereof processes for their preparation and medicaments containing them
US4079081A (en)	1978-03-14	1,1-Diaryl-3-amino-prop-1-enes
US2740795A (en)	1956-04-03	Isoindolineicompounds
JPS6026387B2 (ja)	1985-06-24	シンナミルモラノリン誘導体
US3860652A (en)	1975-01-14	8-Aminoalkyl substituted dibenzobicyclo {8 3.2.1{9 {0 octadienes