ZA200203685B - Diaryl piperidyl pyrrole derivatives as antiprotozoal agents. - Google Patents

Diaryl piperidyl pyrrole derivatives as antiprotozoal agents. Download PDF

Info

Publication number: ZA200203685B
Authority: ZA; South Africa
Prior art keywords: optionally substituted; compound; groups selected; methyl; heteroaryl
Prior art date: 1999-11-12

Application number

ZA200203685A

Other languages

English (en)

Inventor

Tesfaye Biftu

Danqing D Feng

Gui-Bai Laing

Mitree M Ponpipom

Xiaoxia Qian

Michael H Fisher

Matthew J Wyvratt

Original Assignee

Merck & Co Inc

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.)

1999-11-12

Filing date

2002-05-09

Publication date

2003-06-05

2002-05-09 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

2003-06-05 Publication of ZA200203685B publication Critical patent/ZA200203685B/en

Links

-1 Diaryl piperidyl pyrrole derivatives Chemical class 0.000 title claims description 83
239000003904 antiprotozoal agent Substances 0.000 title description 6
244000144977 poultry Species 0.000 claims abstract description 9
208000003495 Coccidiosis Diseases 0.000 claims abstract description 6
206010023076 Isosporiasis Diseases 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
101000995674 Homo sapiens Nutritionally-regulated adipose and cardiac enriched protein homolog Proteins 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
102100034570 Nutritionally-regulated adipose and cardiac enriched protein homolog Human genes 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
229940124536 anticoccidial agent Drugs 0.000 claims description 3
239000003224 coccidiostatic agent Substances 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
125000005916 2-methylpentyl group Chemical group 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
CYIPXMZQMSLCHF-UHFFFAOYSA-N 4-[5-(1-benzylpiperidin-4-yl)-2-(4-fluorophenyl)-1h-pyrrol-3-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)C=C(C2CCN(CC=3C=CC=CC=3)CC2)N1 CYIPXMZQMSLCHF-UHFFFAOYSA-N 0.000 claims description 2
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 claims description 2
125000000173 4-trifluoromethoxy benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC(F)(F)F)C([H])([H])* 0.000 claims description 2
125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
ZDPIZLCVJAAHHR-UHFFFAOYSA-N Clopidol Chemical compound CC1=NC(C)=C(Cl)C(O)=C1Cl ZDPIZLCVJAAHHR-UHFFFAOYSA-N 0.000 claims 2
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
OVMYOJKXLDMDJE-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)-5-(1-phenylpiperidin-4-yl)-1h-pyrrol-3-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)C=C(C2CCN(CC2)C=2C=CC=CC=2)N1 OVMYOJKXLDMDJE-UHFFFAOYSA-N 0.000 claims 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
GOVWOKSKFSBNGD-UHFFFAOYSA-N Ethopabate Chemical compound CCOC1=CC(NC(C)=O)=CC=C1C(=O)OC GOVWOKSKFSBNGD-UHFFFAOYSA-N 0.000 claims 1
229960003683 amprolium Drugs 0.000 claims 1
229960000731 clopidol Drugs 0.000 claims 1
JHAYEQICABJSTP-UHFFFAOYSA-N decoquinate Chemical compound N1C=C(C(=O)OCC)C(=O)C2=C1C=C(OCC)C(OCCCCCCCCCC)=C2 JHAYEQICABJSTP-UHFFFAOYSA-N 0.000 claims 1
229960001878 decoquinate Drugs 0.000 claims 1
229940093501 ethopabate Drugs 0.000 claims 1
PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical group Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 claims 1
150000003233 pyrroles Chemical class 0.000 abstract 1
238000000034 method Methods 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
241000223109 Trypanosoma cruzi Species 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
206010001935 American trypanosomiasis Diseases 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
208000000230 African Trypanosomiasis Diseases 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
208000024699 Chagas disease Diseases 0.000 description 3
241000223924 Eimeria Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
241000282414 Homo sapiens Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
241000295636 Cryptosporidium sp. Species 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
241000223931 Eimeria acervulina Species 0.000 description 2
241000499566 Eimeria brunetti Species 0.000 description 2
241000223934 Eimeria maxima Species 0.000 description 2
241000499563 Eimeria necatrix Species 0.000 description 2
241000223932 Eimeria tenella Species 0.000 description 2
208000004554 Leishmaniasis Diseases 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
150000001204 N-oxides Chemical class 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
241000233872 Pneumocystis carinii Species 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241000223997 Toxoplasma gondii Species 0.000 description 2
206010046914 Vaginal infection Diseases 0.000 description 2
201000008100 Vaginitis Diseases 0.000 description 2
DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical group [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
230000000842 anti-protozoal effect Effects 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
201000004792 malaria Diseases 0.000 description 2
201000000626 mucocutaneous leishmaniasis Diseases 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
201000002311 trypanosomiasis Diseases 0.000 description 2
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
229940013085 2-diethylaminoethanol Drugs 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
SOADNXUWSUZTGY-UHFFFAOYSA-N 4-(1h-pyrrol-3-yl)pyridine Chemical compound N1C=CC(C=2C=CN=CC=2)=C1 SOADNXUWSUZTGY-UHFFFAOYSA-N 0.000 description 1
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
208000004881 Amebiasis Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010001980 Amoebiasis Diseases 0.000 description 1
241000099175 Anaplasma sp. Species 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241001490776 Babesia sp. Species 0.000 description 1
241001235572 Balantioides coli Species 0.000 description 1
241000359271 Besnoitia Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
241000191796 Calyptosphaeria tropica Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
208000008953 Cryptosporidiosis Diseases 0.000 description 1
206010011502 Cryptosporidiosis infection Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241000157305 Dientamoeba Species 0.000 description 1
241000223933 Eimeria bovis Species 0.000 description 1
241000179199 Eimeria mitis Species 0.000 description 1
241000224432 Entamoeba histolytica Species 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000224467 Giardia intestinalis Species 0.000 description 1
241000948219 Histomonas Species 0.000 description 1
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 1
206010061598 Immunodeficiency Diseases 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
241000955225 Isospora sp. Species 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
241000222722 Leishmania <genus> Species 0.000 description 1
241000222740 Leishmania braziliensis Species 0.000 description 1
241000222727 Leishmania donovani Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000243190 Microsporidia Species 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
244000020186 Nymphaea lutea Species 0.000 description 1
208000001388 Opportunistic Infections Diseases 0.000 description 1
240000009188 Phyllostachys vivax Species 0.000 description 1
241000224016 Plasmodium Species 0.000 description 1
241000223960 Plasmodium falciparum Species 0.000 description 1
241000223821 Plasmodium malariae Species 0.000 description 1
206010035501 Plasmodium malariae infection Diseases 0.000 description 1
241001505293 Plasmodium ovale Species 0.000 description 1
206010035502 Plasmodium ovale infection Diseases 0.000 description 1
241000610417 Sarcocystis sp. Species 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
102100028651 Tenascin-N Human genes 0.000 description 1
101710087911 Tenascin-N Proteins 0.000 description 1
241000223777 Theileria Species 0.000 description 1
241000278713 Theora Species 0.000 description 1
201000005485 Toxoplasmosis Diseases 0.000 description 1
241000224526 Trichomonas Species 0.000 description 1
241000893962 Trichophyton equinum Species 0.000 description 1
241001058196 Tritrichomonas foetus Species 0.000 description 1
241000223104 Trypanosoma Species 0.000 description 1
241000223105 Trypanosoma brucei Species 0.000 description 1
241001442399 Trypanosoma brucei gambiense Species 0.000 description 1
241001442397 Trypanosoma brucei rhodesiense Species 0.000 description 1
241000223107 Trypanosoma congolense Species 0.000 description 1
241000223089 Trypanosoma equiperdum Species 0.000 description 1
241000223095 Trypanosoma evansi Species 0.000 description 1
241000223099 Trypanosoma vivax Species 0.000 description 1
206010047505 Visceral leishmaniasis Diseases 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229960003121 arginine Drugs 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
201000008680 babesiosis Diseases 0.000 description 1
208000007456 balantidiasis Diseases 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
229960003237 betaine Drugs 0.000 description 1
230000015572 biosynthetic process Effects 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
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
238000013329 compounding Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
208000001848 dysentery Diseases 0.000 description 1
150000002085 enols Chemical group 0.000 description 1
229940007078 entamoeba histolytica Drugs 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical group C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
229940085435 giardia lamblia Drugs 0.000 description 1
201000006592 giardiasis Diseases 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000036541 health Effects 0.000 description 1
125000004475 heteroaralkyl group Chemical group 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
208000029080 human African trypanosomiasis Diseases 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000006289 hydroxybenzyl group Chemical group 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000005468 isobutylenyl group Chemical group 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 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
150000007522 mineralic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
244000052769 pathogen Species 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000008569 process Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
208000028172 protozoa infectious disease Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003212 purines Chemical class 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
201000002612 sleeping sickness Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical group C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
239000002175 thienopyridine Chemical group 0.000 description 1
229940125670 thienopyridine Drugs 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Veterinary Medicine (AREA)
Animal Husbandry (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Birds (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Tropical Medicine & Parasitology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

ZA200203685A 1999-11-12 2002-05-09 Diaryl piperidyl pyrrole derivatives as antiprotozoal agents. ZA200203685B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US16514299P	1999-11-12	1999-11-12

Publications (1)

Publication Number	Publication Date
ZA200203685B true ZA200203685B (en)	2003-06-05

Family

ID=22597609

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200203685A ZA200203685B (en)	1999-11-12	2002-05-09	Diaryl piperidyl pyrrole derivatives as antiprotozoal agents.

Country Status (11)

Country	Link
US (2)	US6291480B1 (fr)
EP (1)	EP1278520B1 (fr)
JP (1)	JP4722360B2 (fr)
AT (1)	ATE318600T1 (fr)
AU (1)	AU781552B2 (fr)
CA (1)	CA2390100C (fr)
DE (1)	DE60026350T2 (fr)
ES (1)	ES2257336T3 (fr)
NZ (1)	NZ518718A (fr)
WO (1)	WO2001034149A1 (fr)
ZA (1)	ZA200203685B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6432980B1 (en) *	1999-11-12	2002-08-13	Merck & Co., Inc.	Aliphatic amine substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents
EP1414948B1 (fr) *	2001-07-10	2009-09-16	Biogen Idec Inc.	Inhibition de l'apoptose et amelioration de la performance cellulaire
ES2309207T3 (es) *	2001-09-05	2008-12-16	Smithkline Beecham Plc	Derivados furanicos sustituidos con piridina como inhibidores de quinasa raf.
KR20060017865A (ko) *	2003-06-11	2006-02-27	상꾜 가부시키가이샤	환상 3급 아민 화합물
CN101355876B (zh)	2005-11-09	2012-09-05	康宾纳特克斯公司	一种适用于眼部给药的组合物
KR20150119007A (ko) *	2013-02-08	2015-10-23	루오다 파마 피티와이 리미티드	국소 미생물 감염의 치료방법
RU2659205C1 (ru) *	2017-06-01	2018-06-28	Федеральное государственное бюджетное научное учреждение "Прикаспийский зональный научно-исследовательский ветеринарный институт"	Способ профилактики кокцидиоза цыплят-бройлеров при выращивании их на мясо
BE1028700B1 (nl) *	2020-10-13	2022-05-16	Poulpharm Bvba	Werkwijze voor het testen van de efficiëntie van anti-parasitaire (coccidiose) middelen bij pluimvee en konijnen

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4153703A (en) *	1977-06-30	1979-05-08	Uniroyal, Inc.	Method of controlling insects and acarids with certain aryl-substituted thiazoles
WO1996017841A1 (fr) *	1994-12-06	1996-06-13	Nippon Soda Co., Ltd.	Composes de pyridylpyrrole, processus de production et bactericide agro-horticole
EP0863757B1 (fr) *	1995-08-10	2003-03-26	Merck & Co., Inc.	Pyrroles d'aryle substitues en position 2, compositions contenant de tels composes et leurs modes d'utilisation
US5792778A (en) *	1995-08-10	1998-08-11	Merck & Co., Inc.	2-substituted aryl pyrroles, compositions containing such compounds and methods of use
AU7529096A (en) *	1995-10-31	1997-05-22	Merck & Co., Inc.	Substituted aryl pyrroles, compositions containing such compounds and methods of use
JPH09194477A (ja) *	1996-01-18	1997-07-29	Nippon Soda Co Ltd	新規なピリジルピロール化合物、製法および農園芸用殺菌剤
WO1997048725A1 (fr) *	1996-06-21	1997-12-24	Peptech Limited	Nouveaux peptides pour la prevention et le traitement d'infections
JP2000080094A (ja) *	1998-07-02	2000-03-21	Sankyo Co Ltd	５員ヘテロアリ―ル化合物
AU4395399A (en) *	1998-07-02	2000-01-24	Sankyo Company Limited	Five-membered heteroaryl compounds
WO2000066124A1 (fr) *	1999-04-28	2000-11-09	Sankyo Company, Limited	Agents preventifs ou inhibiteurs destines a une hepatopathie
JP2001010957A (ja) *	1999-04-28	2001-01-16	Sankyo Co Ltd	肝障害の予防または抑制剤

2000
- 2000-11-09 ES ES00978439T patent/ES2257336T3/es not_active Expired - Lifetime
- 2000-11-09 JP JP2001536147A patent/JP4722360B2/ja not_active Expired - Lifetime
- 2000-11-09 EP EP00978439A patent/EP1278520B1/fr not_active Expired - Lifetime
- 2000-11-09 WO PCT/US2000/030747 patent/WO2001034149A1/fr active IP Right Grant
- 2000-11-09 NZ NZ518718A patent/NZ518718A/en not_active IP Right Cessation
- 2000-11-09 AT AT00978439T patent/ATE318600T1/de not_active IP Right Cessation
- 2000-11-09 AU AU15904/01A patent/AU781552B2/en not_active Ceased
- 2000-11-09 CA CA002390100A patent/CA2390100C/fr not_active Expired - Lifetime
- 2000-11-09 DE DE60026350T patent/DE60026350T2/de not_active Expired - Lifetime
- 2000-11-10 US US09/710,147 patent/US6291480B1/en not_active Expired - Lifetime
- 2000-11-10 US US09/709,959 patent/US6384052B1/en not_active Expired - Lifetime
2002
- 2002-05-09 ZA ZA200203685A patent/ZA200203685B/en unknown

Also Published As

Publication number	Publication date
ATE318600T1 (de)	2006-03-15
EP1278520A4 (fr)	2003-05-02
JP2003527336A (ja)	2003-09-16
DE60026350D1 (de)	2006-04-27
CA2390100C (fr)	2010-01-05
NZ518718A (en)	2004-03-26
EP1278520B1 (fr)	2006-03-01
WO2001034149A1 (fr)	2001-05-17
ES2257336T3 (es)	2006-08-01
DE60026350T2 (de)	2006-11-09
CA2390100A1 (fr)	2001-05-17
US6384052B1 (en)	2002-05-07
AU781552B2 (en)	2005-05-26
AU1590401A (en)	2001-06-06
JP4722360B2 (ja)	2011-07-13
EP1278520A1 (fr)	2003-01-29
US6291480B1 (en)	2001-09-18

Publication	Publication Date	Title
US8252800B2 (en)	2012-08-28	Protein tyrosine kinase inhibitors
ZA200203685B (en)	2003-06-05	Diaryl piperidyl pyrrole derivatives as antiprotozoal agents.
US20120172325A1 (en)	2012-07-05	Methods and Compositions for the Treatment of Gastrointestinal Disorders
DE102011008352A1 (de)	2012-07-12	5-([1,2,3]Triazol-4-yl)-7H-pyrrolo-[2,3-d]pyrimidinderivate
US10844074B2 (en)	2020-11-24	Heterocycle compounds and uses thereof
US6432980B1 (en)	2002-08-13	Aliphatic amine substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents
US7504501B2 (en)	2009-03-17	Antiprotozoal imidazopyridine compounds
US7429590B2 (en)	2008-09-30	Antiprotozoal imidazopyridine compounds
CA2786715C (fr)	2019-05-21	Aminopyridines fusionnees pour le traitement de tumeurs cerebrales
JPS62129273A (ja)	1987-06-11	１−シクロプロピル−６−フルオロ−１，４−ジヒドロ−４−オキソ−７−（１−ピペラジニル）−３−キノリンカルボン酸類
US11518761B2 (en)	2022-12-06	CDPK1 inhibitors, compositions, and methods related thereto
US6528531B1 (en)	2003-03-04	Aliphatic hydroxy substituted piperidyl diaryl pyrrole derivatives as antiprotozoal agents
CN108619141B (zh)	2021-09-10	一种抗菌组合物及其用途
WO2022014654A1 (fr)	2022-01-20	Agent thérapeutique et/ou prophylactique contre la peste porcine africaine (ppa)
AU2004260832A1 (en)	2005-02-10	Alkaline salts of proton pump inhibitors
CZ363598A3 (cs)	1999-04-14	Anti-"heliobacter pylori" prostředky obsahující 1-methylkarbapenemové deriváty jako aktivní sloučeniny
TW202140039A (zh)	2021-11-01	地西他濱及西屈嘧啶(cedazuridine)組合之固體口服劑型
CN116217621B (zh)	2023-08-11	一种核苷类双前药、合成方法及应用
US11655225B2 (en)	2023-05-23	Antimycobacterial heterocyclic amides
JP5505679B2 (ja)	2014-05-28	原虫感染症の治療又は予防薬
WO2023052468A1 (fr)	2023-04-06	Analogues de nucléosides pour le traitement d'infections parasitaires
Kühler	1998	The Quest for New Chemical Entities to Treat the Gastric Pathogen Helicobacter pylori
CN112898362A (zh)	2021-06-04	一种gpr103蛋白受体抑制剂及其制备和应用
AU2007338377A1 (en)	2008-07-03	Use of polypetides against diseases caused by protozoans