ZA200104443B - Organo-phosphorus compounds and their utilization. - Google Patents

Info

Publication number

ZA200104443B

ZA200104443B ZA200104443A ZA200104443A ZA200104443B ZA 200104443 B ZA200104443 B ZA 200104443B ZA 200104443 A ZA200104443 A ZA 200104443A ZA 200104443 A ZA200104443 A ZA 200104443A ZA 200104443 B ZA200104443 B ZA 200104443B

Authority

ZA

South Africa

Prior art keywords

substituted

group

unsubstituted

alkyl

groups

Prior art date

1998-12-22

Links

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• 150000002903 organophosphorus compounds Chemical class 0.000 title claims description 16
• -1 hydroxy, amino Chemical group 0.000 claims description 84
• 241000894006 Bacteria Species 0.000 claims description 37
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 150000001875 compounds Chemical class 0.000 claims description 31
• 239000013543 active substance Substances 0.000 claims description 29
• 229910052736 halogen Inorganic materials 0.000 claims description 26
• 150000002367 halogens Chemical group 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 241000700605 Viruses Species 0.000 claims description 21
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 239000002253 acid Substances 0.000 claims description 18
• 125000004043 oxo group Chemical group O=* 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 150000002148 esters Chemical class 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 244000045947 parasite Species 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
• 125000002252 acyl group Chemical group 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 10
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 10
• NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 241000233866 Fungi Species 0.000 claims description 8
• 150000003863 ammonium salts Chemical class 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 230000000844 anti-bacterial effect Effects 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 150000001413 amino acids Chemical class 0.000 claims description 6
• 201000004792 malaria Diseases 0.000 claims description 6
• 125000004437 phosphorous atom Chemical group 0.000 claims description 6
• 229910052698 phosphorus Inorganic materials 0.000 claims description 6
• 208000000230 African Trypanosomiasis Diseases 0.000 claims description 5
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 230000000855 fungicidal effect Effects 0.000 claims description 5
• 208000029080 human African trypanosomiasis Diseases 0.000 claims description 5
• 238000000034 method Methods 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 238000011321 prophylaxis Methods 0.000 claims description 5
• 201000002612 sleeping sickness Diseases 0.000 claims description 5
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
• 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 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
• 150000003868 ammonium compounds Chemical class 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000004185 ester group Chemical group 0.000 claims description 4
• 230000002363 herbicidal effect Effects 0.000 claims description 4
• 229910052751 metal Inorganic materials 0.000 claims description 4
• 239000002184 metal Substances 0.000 claims description 4
• 230000000737 periodic effect Effects 0.000 claims description 4
• 239000011591 potassium Substances 0.000 claims description 4
• 229910052700 potassium Inorganic materials 0.000 claims description 4
• 229910052708 sodium Inorganic materials 0.000 claims description 4
• 239000011734 sodium Substances 0.000 claims description 4
• 230000001225 therapeutic effect Effects 0.000 claims description 4
• 206010001935 American trypanosomiasis Diseases 0.000 claims description 3
• 206010001986 Amoebic dysentery Diseases 0.000 claims description 3
• 208000024699 Chagas disease Diseases 0.000 claims description 3
• 208000003495 Coccidiosis Diseases 0.000 claims description 3
• 208000008953 Cryptosporidiosis Diseases 0.000 claims description 3
• 206010011502 Cryptosporidiosis infection Diseases 0.000 claims description 3
• 206010023076 Isosporiasis Diseases 0.000 claims description 3
• 208000004554 Leishmaniasis Diseases 0.000 claims description 3
• 208000005384 Pneumocystis Pneumonia Diseases 0.000 claims description 3
• 206010073755 Pneumocystis jirovecii pneumonia Diseases 0.000 claims description 3
• 201000005485 Toxoplasmosis Diseases 0.000 claims description 3
• 208000005448 Trichomonas Infections Diseases 0.000 claims description 3
• 206010044620 Trichomoniasis Diseases 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 239000003899 bactericide agent Substances 0.000 claims description 3
• 208000007456 balantidiasis Diseases 0.000 claims description 3
• 239000000417 fungicide Substances 0.000 claims description 3
• 201000006592 giardiasis Diseases 0.000 claims description 3
• 239000004009 herbicide Substances 0.000 claims description 3
• 150000007529 inorganic bases Chemical class 0.000 claims description 3
• 150000007530 organic bases Chemical class 0.000 claims description 3
• 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 3
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 3
• 201000000317 pneumocystosis Diseases 0.000 claims description 3
• 125000004434 sulfur atom Chemical group 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 2
• 150000001768 cations Chemical class 0.000 claims description 2
• 125000003367 polycyclic group Chemical group 0.000 claims description 2
• 102100030760 Apolipoprotein F Human genes 0.000 claims 1
• IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims 1
• 101000793431 Homo sapiens Apolipoprotein F Proteins 0.000 claims 1
• 125000004450 alkenylene group Chemical group 0.000 claims 1
• 230000002458 infectious effect Effects 0.000 claims 1
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 230000002265 prevention Effects 0.000 claims 1
• 239000000203 mixture Substances 0.000 description 76
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
• 239000000243 solution Substances 0.000 description 55
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
• 239000003921 oil Substances 0.000 description 35
• 235000019198 oils Nutrition 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 241001465754 Metazoa Species 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
• 238000001816 cooling Methods 0.000 description 23
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• 241000282412 Homo Species 0.000 description 20
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
• 235000002639 sodium chloride Nutrition 0.000 description 19
• 239000002904 solvent Substances 0.000 description 19
• 239000000126 substance Substances 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 15
• 235000019441 ethanol Nutrition 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
• 239000008346 aqueous phase Substances 0.000 description 13
• 239000012043 crude product Substances 0.000 description 13
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• 239000012074 organic phase Substances 0.000 description 12
• 229910052786 argon Inorganic materials 0.000 description 11
• IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 11
• 230000008029 eradication Effects 0.000 description 11
• 239000003826 tablet Substances 0.000 description 11
• 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 description 10
• 239000000741 silica gel Substances 0.000 description 10
• 229910002027 silica gel Inorganic materials 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
• 238000001704 evaporation Methods 0.000 description 8
• 230000008020 evaporation Effects 0.000 description 8
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
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• 239000005457 ice water Substances 0.000 description 7
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• 159000000000 sodium salts Chemical class 0.000 description 7
• AKFBTNQCYMSUQF-UHFFFAOYSA-N 1-(2-dimethoxyphosphorylethyl)-7-methyl-3h-purine-2,6-dione Chemical compound O=C1N(CCP(=O)(OC)OC)C(=O)NC2=C1N(C)C=N2 AKFBTNQCYMSUQF-UHFFFAOYSA-N 0.000 description 6
• VMMFXTABTYOCGF-UHFFFAOYSA-N 2-(1-hydroxy-2-oxopyridin-3-yl)ethylphosphonic acid Chemical compound ON1C=CC=C(CCP(O)(O)=O)C1=O VMMFXTABTYOCGF-UHFFFAOYSA-N 0.000 description 6
• BVMUOARBOUMJBI-UHFFFAOYSA-N 5-(2-dimethoxyphosphorylethyl)pyrrolidin-2-one Chemical compound COP(=O)(OC)CCC1CCC(=O)N1 BVMUOARBOUMJBI-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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• 238000001035 drying Methods 0.000 description 6
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• 241000196324 Embryophyta Species 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• 150000001335 aliphatic alkanes Chemical group 0.000 description 5
• 125000001931 aliphatic group Chemical group 0.000 description 5
• 239000002775 capsule Substances 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 239000000460 chlorine Substances 0.000 description 5
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• 239000011521 glass Substances 0.000 description 5
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• 229960002317 succinimide Drugs 0.000 description 5
• FRLDLZDJVBQJDA-UHFFFAOYSA-N (4-amino-1-hydroxy-5-oxopyrrolidin-3-yl)methylphosphonic acid Chemical compound NC1C(CP(O)(O)=O)CN(O)C1=O FRLDLZDJVBQJDA-UHFFFAOYSA-N 0.000 description 4
• ZOVDWTXRLXEPEV-UHFFFAOYSA-N 1-(2-dimethoxyphosphorylethyl)-3-hydroxy-7-methylpurine-2,6-dione Chemical compound O=C1N(CCP(=O)(OC)OC)C(=O)N(O)C2=C1N(C)C=N2 ZOVDWTXRLXEPEV-UHFFFAOYSA-N 0.000 description 4
• CJVHLUSZUITNOF-UHFFFAOYSA-N 2-(1-hydroxy-5-oxopyrrolidin-2-yl)ethylphosphonic acid Chemical compound ON1C(CCP(O)(O)=O)CCC1=O CJVHLUSZUITNOF-UHFFFAOYSA-N 0.000 description 4
• WHXCYZDDCFQVNR-UHFFFAOYSA-N 2-(2-dimethoxyphosphorylethyl)pyrrolidine Chemical compound COP(=O)(OC)CCC1CCCN1 WHXCYZDDCFQVNR-UHFFFAOYSA-N 0.000 description 4
• DSJFRPMFQOMWDN-UHFFFAOYSA-N 2-(3-hydroxy-7-methyl-2,6-dioxopurin-1-yl)ethylphosphonic acid Chemical compound ON1C(=O)N(CCP(O)(O)=O)C(=O)C2=C1N=CN2C DSJFRPMFQOMWDN-UHFFFAOYSA-N 0.000 description 4
• PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
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• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 4
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• AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 4
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
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• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
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• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• 230000000699 topical effect Effects 0.000 description 4
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