DE3123295C2 - - Google Patents
Info
- Publication number
- DE3123295C2 DE3123295C2 DE3123295A DE3123295A DE3123295C2 DE 3123295 C2 DE3123295 C2 DE 3123295C2 DE 3123295 A DE3123295 A DE 3123295A DE 3123295 A DE3123295 A DE 3123295A DE 3123295 C2 DE3123295 C2 DE 3123295C2
- Authority
- DE
- Germany
- Prior art keywords
- acid
- compounds
- solution
- animals
- difluoromethyl
- Prior art date
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 49
- 241001465754 Metazoa Species 0.000 claims description 32
- -1 fluorine-methylpentanoic acid Chemical compound 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 8
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 8
- 208000010362 Protozoan Infections Diseases 0.000 claims description 8
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- 208000015181 infectious disease Diseases 0.000 description 22
- 241000287828 Gallus gallus Species 0.000 description 21
- 235000013330 chicken meat Nutrition 0.000 description 20
- VLCYCQAOQCDTCN-UHFFFAOYSA-N eflornithine Chemical compound NCCCC(N)(C(F)F)C(O)=O VLCYCQAOQCDTCN-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 244000144977 poultry Species 0.000 description 17
- 235000013594 poultry meat Nutrition 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 230000012010 growth Effects 0.000 description 16
- 241000223932 Eimeria tenella Species 0.000 description 15
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 15
- 229920000768 polyamine Polymers 0.000 description 14
- 208000003495 Coccidiosis Diseases 0.000 description 13
- 206010023076 Isosporiasis Diseases 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000003651 drinking water Substances 0.000 description 11
- 235000020188 drinking water Nutrition 0.000 description 11
- 210000004534 cecum Anatomy 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 230000002401 inhibitory effect Effects 0.000 description 8
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 8
- ATHGHQPFGPMSJY-UHFFFAOYSA-N spermidine Chemical compound NCCCCNCCCN ATHGHQPFGPMSJY-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000005700 Putrescine Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 241000894007 species Species 0.000 description 6
- PFNFFQXMRSDOHW-UHFFFAOYSA-N spermine Chemical compound NCCCNCCCCNCCCN PFNFFQXMRSDOHW-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 210000003250 oocyst Anatomy 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000224483 Coccidia Species 0.000 description 4
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 4
- 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 4
- 241000699670 Mus sp. Species 0.000 description 4
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 4
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 4
- 102000052812 Ornithine decarboxylases Human genes 0.000 description 4
- 108700005126 Ornithine decarboxylases Proteins 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 150000003951 lactams Chemical class 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229960003104 ornithine Drugs 0.000 description 4
- 244000045947 parasite Species 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 229940063673 spermidine Drugs 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- JWWZUFCRQMJENK-UHFFFAOYSA-N 2,5-diamino-2-ethynylpentanoic acid Chemical compound NCCCC(N)(C#C)C(O)=O JWWZUFCRQMJENK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 208000000230 African Trypanosomiasis Diseases 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 241001375804 Mastigophora Species 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000223104 Trypanosoma Species 0.000 description 3
- 241000223105 Trypanosoma brucei Species 0.000 description 3
- 241000224557 Trypanosoma brucei brucei Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001371 alpha-amino acids Chemical class 0.000 description 3
- 235000008206 alpha-amino acids Nutrition 0.000 description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000032823 cell division Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940099112 cornstarch Drugs 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- QIADQCOYEFCREQ-UHFFFAOYSA-N hept-6-yne-2,5-diamine Chemical compound CC(N)CCC(N)C#C QIADQCOYEFCREQ-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical class NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 229940063675 spermine Drugs 0.000 description 3
- NCXVVWPPTWFPHG-UHFFFAOYSA-N 1-fluorohexane-2,5-diamine;dihydrochloride Chemical compound Cl.Cl.CC(N)CCC(N)CF NCXVVWPPTWFPHG-UHFFFAOYSA-N 0.000 description 2
- ZTXMFONOQDOQIF-UHFFFAOYSA-N 2-(5-fluoro-4-hydroxypentyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC(CF)O)C(=O)C2=C1 ZTXMFONOQDOQIF-UHFFFAOYSA-N 0.000 description 2
- DNLPDGCZFXNNQO-UHFFFAOYSA-N 2-(5-fluoro-4-oxopentyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCC(=O)CF)C(=O)C2=C1 DNLPDGCZFXNNQO-UHFFFAOYSA-N 0.000 description 2
- KTZQXOLUWRTUAY-UHFFFAOYSA-N 2-(6-fluoro-5-oxohexan-2-yl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C(CCC(=O)CF)C)C(=O)C2=C1 KTZQXOLUWRTUAY-UHFFFAOYSA-N 0.000 description 2
- CIVSTPRPVGWVII-UHFFFAOYSA-N 4-[4-(1,3-dioxoisoindol-4-yl)-5-fluoropentyl]isoindole-1,3-dione Chemical compound C=1C=CC=2C(=O)NC(=O)C=2C=1CCCC(CF)C1=CC=CC2=C1C(=O)NC2=O CIVSTPRPVGWVII-UHFFFAOYSA-N 0.000 description 2
- FEZKBTUXSHFTNL-UHFFFAOYSA-N 5,5-difluoro-4-methylpentane-1,4-diamine Chemical compound FC(F)C(N)(C)CCCN FEZKBTUXSHFTNL-UHFFFAOYSA-N 0.000 description 2
- PKOKVLWYGQNQDJ-UHFFFAOYSA-N 5-fluoropentane-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.NCCCC(N)CF PKOKVLWYGQNQDJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- 241000389783 Bulbonaricus brucei Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 206010059866 Drug resistance Diseases 0.000 description 2
- 241000223924 Eimeria Species 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 241000606766 Haemophilus parainfluenzae Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 229960003683 amprolium Drugs 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 239000003224 coccidiostatic agent Substances 0.000 description 2
- 239000003954 decarboxylase inhibitor Substances 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 231100000676 disease causative agent Toxicity 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000008241 heterogeneous mixture Substances 0.000 description 2
- PJBQYZZKGNOKNJ-UHFFFAOYSA-M hydron;5-[(2-methylpyridin-1-ium-1-yl)methyl]-2-propylpyrimidin-4-amine;dichloride Chemical compound Cl.[Cl-].NC1=NC(CCC)=NC=C1C[N+]1=CC=CC=C1C PJBQYZZKGNOKNJ-UHFFFAOYSA-M 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 210000003936 merozoite Anatomy 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- 235000006109 methionine Nutrition 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- AFDMODCXODAXLC-UHFFFAOYSA-N phenylmethanimine Chemical compound N=CC1=CC=CC=C1 AFDMODCXODAXLC-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- DAJKXFBCODIPEX-UHFFFAOYSA-N 1,1,1-trifluorohexane-2,5-diamine Chemical compound CC(N)CCC(N)C(F)(F)F DAJKXFBCODIPEX-UHFFFAOYSA-N 0.000 description 1
- YSUINMDKTTYCFN-UHFFFAOYSA-N 1-fluorohexane-2,5-diamine Chemical compound CC(N)CCC(N)CF YSUINMDKTTYCFN-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- VOLJNJRRHNKYBB-UHFFFAOYSA-N 2,5-diamino-2-(difluoromethyl)hexanoic acid Chemical compound CC(N)CCC(N)(C(F)F)C(O)=O VOLJNJRRHNKYBB-UHFFFAOYSA-N 0.000 description 1
- RSHAFLMQMASOCX-UHFFFAOYSA-N 2,5-diamino-2-(fluoromethyl)hexanoic acid Chemical compound CC(N)CCC(N)(CF)C(O)=O RSHAFLMQMASOCX-UHFFFAOYSA-N 0.000 description 1
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- 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
- A23K20/105—Aliphatic or alicyclic compounds
-
- 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
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Epidemiology (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Animal Husbandry (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15997380A | 1980-06-16 | 1980-06-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3123295A1 DE3123295A1 (de) | 1982-04-29 |
| DE3123295C2 true DE3123295C2 (enrdf_load_stackoverflow) | 1990-07-12 |
Family
ID=22574910
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3153623A Expired - Lifetime DE3153623C2 (enrdf_load_stackoverflow) | 1980-06-16 | 1981-06-12 | |
| DE19813123295 Granted DE3123295A1 (de) | 1980-06-16 | 1981-06-12 | "verwendung einer (alpha)-substituierten aminosaeure oder eines (alpha)-substituierten amins zur bekaempfung von protozoen-infektionen bei tieren" |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3153623A Expired - Lifetime DE3153623C2 (enrdf_load_stackoverflow) | 1980-06-16 | 1981-06-12 |
Country Status (17)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58123555U (ja) * | 1982-02-17 | 1983-08-23 | 三菱電機株式会社 | インライン型電子銃の組立装置 |
| NL8400927A (nl) * | 1984-03-23 | 1985-10-16 | Philips Nv | Inrichting en werkwijze voor het monteren van een geintegreerd elektronenkanonsysteem. |
| DE3421384A1 (de) * | 1984-06-08 | 1985-12-12 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Vorrichtung zum zusammenbau von elektronenstrahlerzeugern |
| JPS62148462A (ja) * | 1985-12-19 | 1987-07-02 | メレルダウフア−マス−テイカルズ インコ−ポレ−テツド | 原生動物の生長を抑制する新規な方法 |
| ATE77367T1 (de) * | 1988-02-05 | 1992-07-15 | Merrell Dow Pharma | 5-substituierte ornithin-derivate. |
| US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR64495B (en) * | 1977-06-01 | 1980-03-31 | Merck & Co Inc | Novel fluorinated amino acids |
| US4139563A (en) * | 1977-07-01 | 1979-02-13 | Merrell Toraude Et Compagnie | α-ACETYLENIC DERIVATIVES OF AMINES |
| US4088667A (en) * | 1977-07-01 | 1978-05-09 | Merrell Toraude Et Compagnie | Lower alkyl 2-tri-(lower)alkylsilylacetylene-N-carbethoxyglycinates and process for using same |
| CA1121375A (en) * | 1977-07-01 | 1982-04-06 | Brian W. Metcalf | Derivatives of amines and amino acids |
| US4182891A (en) * | 1977-07-01 | 1980-01-08 | Merrell Toraude Et Compagnie | α-Acetylenic derivatives of α-amino acids |
| CA1091661A (en) * | 1977-07-11 | 1980-12-16 | Philippe Bey | .alpha.-HALOMETHYL DERIVATIVES OF .alpha.-AMINO ACIDS |
| US4134918A (en) * | 1977-09-06 | 1979-01-16 | Merrell Toraude Et Compagnie | Alpha-halomethyl derivatives of amines |
-
1981
- 1981-06-11 NZ NZ197394A patent/NZ197394A/en unknown
- 1981-06-11 AU AU71654/81A patent/AU544990B2/en not_active Expired
- 1981-06-11 SE SE8103678A patent/SE460517B/sv not_active IP Right Cessation
- 1981-06-11 CA CA000379588A patent/CA1174603A/en not_active Expired
- 1981-06-11 ZA ZA813953A patent/ZA813953B/xx unknown
- 1981-06-11 PH PH25759A patent/PH16634A/en unknown
- 1981-06-12 IE IE1308/81A patent/IE51300B1/en not_active IP Right Cessation
- 1981-06-12 DE DE3153623A patent/DE3153623C2/de not_active Expired - Lifetime
- 1981-06-12 IL IL63087A patent/IL63087A/xx not_active IP Right Cessation
- 1981-06-12 DE DE19813123295 patent/DE3123295A1/de active Granted
- 1981-06-15 CH CH3939/81A patent/CH651206A5/de not_active IP Right Cessation
- 1981-06-15 IT IT48684/81A patent/IT1171380B/it active
- 1981-06-15 NL NL8102863A patent/NL194153C/nl not_active IP Right Cessation
- 1981-06-15 AT AT0266581A patent/AT377180B/de not_active IP Right Cessation
- 1981-06-15 FR FR8111733A patent/FR2484255A1/fr active Granted
- 1981-06-15 GB GB8118326A patent/GB2078735B/en not_active Expired
- 1981-06-15 JP JP9208181A patent/JPS5731613A/ja active Granted
- 1981-06-15 BE BE0/205104A patent/BE889230A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE811308L (en) | 1981-12-16 |
| FR2484255A1 (fr) | 1981-12-18 |
| PH16634A (en) | 1983-12-05 |
| ATA266581A (de) | 1984-07-15 |
| NL8102863A (nl) | 1982-01-18 |
| DE3153623C2 (enrdf_load_stackoverflow) | 1991-06-27 |
| FR2484255B1 (enrdf_load_stackoverflow) | 1984-12-14 |
| DE3123295A1 (de) | 1982-04-29 |
| JPH0432052B2 (enrdf_load_stackoverflow) | 1992-05-28 |
| NZ197394A (en) | 1984-09-28 |
| IT1171380B (it) | 1987-06-10 |
| IL63087A (en) | 1984-10-31 |
| AU7165481A (en) | 1981-12-24 |
| AU544990B2 (en) | 1985-06-27 |
| AT377180B (de) | 1985-02-25 |
| GB2078735B (en) | 1985-05-15 |
| NL194153B (nl) | 2001-04-02 |
| ZA813953B (en) | 1982-06-30 |
| CA1174603A (en) | 1984-09-18 |
| BE889230A (fr) | 1981-12-15 |
| JPS5731613A (en) | 1982-02-20 |
| CH651206A5 (de) | 1985-09-13 |
| NL194153C (nl) | 2001-08-03 |
| SE8103678L (sv) | 1981-12-17 |
| GB2078735A (en) | 1982-01-13 |
| SE460517B (sv) | 1989-10-23 |
| IT8148684A0 (it) | 1981-06-15 |
| IE51300B1 (en) | 1986-11-26 |
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