CH626350A5 - - Google Patents

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Info

Publication number: CH626350A5
Authority: CH; Switzerland
Prior art keywords: nitro; methyl; pyrazolyl; acrylic acid; acid
Prior art date: 1975-12-23

Application number

CH1602076A

Other languages

German (de)

English (en)

Inventor

Herbert Dr Phil Berger

Rudi Dr Phil Gall

Kurt Dr Ing Stach

Max Dr Rer Nat Thiel

Wolfgang Dr Med Voemel

Original Assignee

Boehringer Mannheim Gmbh

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.)

1975-12-23

Filing date

1976-12-20

Publication date

1981-11-13

1976-12-20 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1981-11-13 Publication of CH626350A5 publication Critical patent/CH626350A5/de

Links

-1 cyano, carboxyl Chemical group 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
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 claims description 2
MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical class [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
239000000243 solution Substances 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
239000000203 mixture Substances 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 13
150000001732 carboxylic acid derivatives Chemical class 0.000 description 13
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
238000001035 drying Methods 0.000 description 12
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
239000000126 substance Substances 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
QJHQWVPVQZSFEY-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enoyl chloride Chemical compound CN1C=C(C=CC(Cl)=O)C([N+]([O-])=O)=N1 QJHQWVPVQZSFEY-UHFFFAOYSA-N 0.000 description 9
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
RRMNMXOVJGLXCJ-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CN1C=C(C=CC(N)=O)C([N+]([O-])=O)=N1 RRMNMXOVJGLXCJ-UHFFFAOYSA-N 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
239000000284 extract Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
UUOPSPAIZDMDTG-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enoic acid Chemical compound CN1C=C(C=CC(O)=O)C([N+]([O-])=O)=N1 UUOPSPAIZDMDTG-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000005187 foaming Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
238000005406 washing Methods 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
150000003857 carboxamides Chemical class 0.000 description 5
150000001733 carboxylic acid esters Chemical class 0.000 description 5
ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
KVHJPNRWUSXYNA-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enenitrile Chemical compound CN1C=C(C=CC#N)C([N+]([O-])=O)=N1 KVHJPNRWUSXYNA-UHFFFAOYSA-N 0.000 description 4
NVZUVJQBCXQIIE-UHFFFAOYSA-N 5-nitro-1h-pyrazole-4-carbaldehyde Chemical class [O-][N+](=O)C1=NNC=C1C=O NVZUVJQBCXQIIE-UHFFFAOYSA-N 0.000 description 4
KTIIXGKNWFWDGX-UHFFFAOYSA-N 5-nitro-1h-pyrazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NNC=1[N+]([O-])=O KTIIXGKNWFWDGX-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000007789 gas Substances 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
SMXDRRLYXOTORT-UHFFFAOYSA-N 1-methyl-3-nitropyrazole-4-carboxylic acid Chemical compound CN1C=C(C(O)=O)C([N+]([O-])=O)=N1 SMXDRRLYXOTORT-UHFFFAOYSA-N 0.000 description 3
NAQINTQBFGWYKY-UHFFFAOYSA-N 3-(1-ethyl-3-nitropyrazol-4-yl)prop-2-enoic acid Chemical compound CCN1C=C(C=CC(O)=O)C([N+]([O-])=O)=N1 NAQINTQBFGWYKY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
125000005115 alkyl carbamoyl group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 3
YNKDRTCJDFVUTJ-UHFFFAOYSA-N carbonyl diisocyanate Chemical compound O=C=NC(=O)N=C=O YNKDRTCJDFVUTJ-UHFFFAOYSA-N 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
125000000753 cycloalkyl group Chemical group 0.000 description 3
125000005117 dialkylcarbamoyl group Chemical group 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
HTBVGZAVHBZXMS-UHFFFAOYSA-N lithium;tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Li].[Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] HTBVGZAVHBZXMS-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
ONQRPGFVJZFJFZ-UHFFFAOYSA-N (5-nitro-1h-pyrazol-4-yl)methanol Chemical class OCC1=CNN=C1[N+]([O-])=O ONQRPGFVJZFJFZ-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
GWSDVULKLBQFGB-UHFFFAOYSA-N 3-(1,5-dimethyl-3-nitropyrazol-4-yl)prop-2-enoic acid Chemical compound CC1=C(C=CC(O)=O)C([N+]([O-])=O)=NN1C GWSDVULKLBQFGB-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
230000009435 amidation Effects 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
OWAZUFKLSUYZFV-UHFFFAOYSA-N aminothiourea 3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enoic acid Chemical compound NNC(=S)N.CN1N=C(C(=C1)C=CC(=O)O)[N+](=O)[O-] OWAZUFKLSUYZFV-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
125000005265 dialkylamine group Chemical group 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
229960004285 fomepizole Drugs 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical compound NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 2
ZRJGPZKADDUALZ-UHFFFAOYSA-N n-(4-hydroxyphenyl)-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound [O-][N+](=O)C1=NN(C)C=C1C=CC(=O)NC1=CC=C(O)C=C1 ZRJGPZKADDUALZ-UHFFFAOYSA-N 0.000 description 2
RSMWKSIQPIDNGW-UHFFFAOYSA-N n-hydroxy-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CN1C=C(C=CC(=O)NO)C([N+]([O-])=O)=N1 RSMWKSIQPIDNGW-UHFFFAOYSA-N 0.000 description 2
OMFJIMIGMSLGRN-UHFFFAOYSA-N n-methyl-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CNC(=O)C=CC1=CN(C)N=C1[N+]([O-])=O OMFJIMIGMSLGRN-UHFFFAOYSA-N 0.000 description 2
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical group [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
235000019345 sodium thiosulphate Nutrition 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
238000007056 transamidation reaction Methods 0.000 description 2
238000005809 transesterification reaction Methods 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
PCDSBHWKDOKENY-UHFFFAOYSA-N 1,4-dimethyl-3-nitropyrazole Chemical compound CC1=CN(C)N=C1[N+]([O-])=O PCDSBHWKDOKENY-UHFFFAOYSA-N 0.000 description 1
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
DJBRVBRUYSSMJT-UHFFFAOYSA-N 1,5-dimethyl-3-nitropyrazole-4-carbaldehyde Chemical compound CC1=C(C=O)C([N+]([O-])=O)=NN1C DJBRVBRUYSSMJT-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
VYMKTOBQNYJWHY-UHFFFAOYSA-N 3-(1,5-dimethyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CC1=C(C=CC(N)=O)C([N+]([O-])=O)=NN1C VYMKTOBQNYJWHY-UHFFFAOYSA-N 0.000 description 1
DULRAGKKCKCFTP-UHFFFAOYSA-N 3-(1-ethyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CCN1C=C(C=CC(N)=O)C([N+]([O-])=O)=N1 DULRAGKKCKCFTP-UHFFFAOYSA-N 0.000 description 1
JLXKEGPFFJUANL-UHFFFAOYSA-N 3-(1-ethyl-3-nitropyrazol-4-yl)prop-2-enoyl chloride Chemical compound CCN1C=C(C=CC(Cl)=O)C([N+]([O-])=O)=N1 JLXKEGPFFJUANL-UHFFFAOYSA-N 0.000 description 1
QFNMKPSDYSGUQZ-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)-1-piperidin-1-ylprop-2-en-1-one Chemical compound [O-][N+](=O)C1=NN(C)C=C1C=CC(=O)N1CCCCC1 QFNMKPSDYSGUQZ-UHFFFAOYSA-N 0.000 description 1
AFSYOTIOUXYOMF-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)-n-(6-methylpyridin-2-yl)prop-2-enamide Chemical compound CC1=CC=CC(NC(=O)C=CC=2C(=NN(C)C=2)[N+]([O-])=O)=N1 AFSYOTIOUXYOMF-UHFFFAOYSA-N 0.000 description 1
VBNYAWMKPIQGHV-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)-n-(pyrrolidin-1-ylmethyl)prop-2-enamide Chemical compound [O-][N+](=O)C1=NN(C)C=C1C=CC(=O)NCN1CCCC1 VBNYAWMKPIQGHV-UHFFFAOYSA-N 0.000 description 1
GDGBXGCXHCCTPE-UHFFFAOYSA-N 3-(1-methyl-3-nitropyrazol-4-yl)-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=CC1=CN(C)N=C1[N+]([O-])=O GDGBXGCXHCCTPE-UHFFFAOYSA-N 0.000 description 1
PBVZQAXFSQKDKK-UHFFFAOYSA-N 3-Methoxy-3-oxopropanoic acid Chemical compound COC(=O)CC(O)=O PBVZQAXFSQKDKK-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
JRMKJOOJKCAEJK-UHFFFAOYSA-N 4-Hydroxymethylpyrazole Chemical compound OCC=1C=NNC=1 JRMKJOOJKCAEJK-UHFFFAOYSA-N 0.000 description 1
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
BHWGVDFLAUBWLA-UHFFFAOYSA-N 5-nitro-1h-pyrazole-4-carbonitrile Chemical compound [O-][N+](=O)C=1NN=CC=1C#N BHWGVDFLAUBWLA-UHFFFAOYSA-N 0.000 description 1
QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
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241000206672 Gelidium Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
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235000010419 agar Nutrition 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
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150000003973 alkyl amines Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
BGPRIWQDTSPOMF-UHFFFAOYSA-N aminourea;3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enoic acid Chemical compound NNC(N)=O.CN1C=C(C=CC(O)=O)C([N+]([O-])=O)=N1 BGPRIWQDTSPOMF-UHFFFAOYSA-N 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940117975 chromium trioxide Drugs 0.000 description 1
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
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239000008139 complexing agent Substances 0.000 description 1
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235000014113 dietary fatty acids Nutrition 0.000 description 1
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239000003937 drug carrier Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
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235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XPYYDGMVSUHSGV-UHFFFAOYSA-N methyl 3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enoate Chemical compound COC(=O)C=CC1=CN(C)N=C1[N+]([O-])=O XPYYDGMVSUHSGV-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 1
IUKLOZSFWBLOOE-UHFFFAOYSA-N n-(2-acetamidoethyl)-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CC(=O)NCCNC(=O)C=CC1=CN(C)N=C1[N+]([O-])=O IUKLOZSFWBLOOE-UHFFFAOYSA-N 0.000 description 1
VWRIYGBRDFWKJS-UHFFFAOYSA-N n-(2-aminoethyl)-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CN1C=C(C=CC(=O)NCCN)C([N+]([O-])=O)=N1 VWRIYGBRDFWKJS-UHFFFAOYSA-N 0.000 description 1
AZOHGHCKWRFQFG-UHFFFAOYSA-N n-(2-aminoethyl)-n-methyl-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound NCCN(C)C(=O)C=CC1=CN(C)N=C1[N+]([O-])=O AZOHGHCKWRFQFG-UHFFFAOYSA-N 0.000 description 1
GKWORFWYHKGBRY-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CN1C=C(C=CC(=O)NCCO)C([N+]([O-])=O)=N1 GKWORFWYHKGBRY-UHFFFAOYSA-N 0.000 description 1
UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
FTEODAOCMZUYJB-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)prop-2-enamide Chemical compound CC1=CC=CC(NC(=O)C=C)=N1 FTEODAOCMZUYJB-UHFFFAOYSA-N 0.000 description 1
ZGGUOTQGFCYEEX-UHFFFAOYSA-N n-(aminomethyl)formamide Chemical class NCNC=O ZGGUOTQGFCYEEX-UHFFFAOYSA-N 0.000 description 1
BEBUJFZTICHXNL-UHFFFAOYSA-N n-(cyanomethyl)-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CN1C=C(C=CC(=O)NCC#N)C([N+]([O-])=O)=N1 BEBUJFZTICHXNL-UHFFFAOYSA-N 0.000 description 1
RNIBKRCCMCVMQN-UHFFFAOYSA-N n-(methylcarbamoyl)-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CNC(=O)NC(=O)C=CC1=CN(C)N=C1[N+]([O-])=O RNIBKRCCMCVMQN-UHFFFAOYSA-N 0.000 description 1
WSWNRAXDTBQNGQ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound CCN(CC)CCNC(=O)C=CC1=CN(C)N=C1[N+]([O-])=O WSWNRAXDTBQNGQ-UHFFFAOYSA-N 0.000 description 1
JOWMUPQBELRFRZ-UHFFFAOYSA-N n-carbamoylformamide Chemical compound NC(=O)NC=O JOWMUPQBELRFRZ-UHFFFAOYSA-N 0.000 description 1
WKINMYUMJFMKFE-UHFFFAOYSA-N n-cyclopropyl-3-(1-methyl-3-nitropyrazol-4-yl)prop-2-enamide Chemical compound [O-][N+](=O)C1=NN(C)C=C1C=CC(=O)NC1CC1 WKINMYUMJFMKFE-UHFFFAOYSA-N 0.000 description 1
LCXIFAOALNZGDO-UHFFFAOYSA-N n-cyclopropylprop-2-enamide Chemical compound C=CC(=O)NC1CC1 LCXIFAOALNZGDO-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
150000003140 primary amides Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1602076A 1975-12-23 1976-12-20 CH626350A5 (it)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19752558117 DE2558117A1 (de)	1975-12-23	1975-12-23	3-nitropyrazol-derivate

Publications (1)

Publication Number	Publication Date
CH626350A5 true CH626350A5 (it)	1981-11-13

Family

ID=5965346

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1602076A CH626350A5 (it)	1975-12-23	1976-12-20

Country Status (15)

Country	Link
US (1)	US4105772A (it)
JP (1)	JPS5283370A (it)
AR (1)	AR213107A1 (it)
AT (1)	AT353259B (it)
AU (1)	AU502076B2 (it)
BE (1)	BE849614A (it)
CA (1)	CA1069515A (it)
CH (1)	CH626350A5 (it)
DD (1)	DD127652A5 (it)
DE (1)	DE2558117A1 (it)
ES (1)	ES454299A1 (it)
FR (1)	FR2336128A1 (it)
GB (1)	GB1512763A (it)
HU (1)	HU173563B (it)
NL (1)	NL7614011A (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2747531A1 (de)	1977-10-22	1979-04-26	Basf Ag	Substituierte 3-aminopyrazole
BR0112373A (pt)	2000-07-04	2003-09-09	Ube Industries	Compostos de benzoxazol, processo para a produção dos mesmos e herbicidas

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1373212A (en) *	1970-12-07	1974-11-06	Wyeth John & Brother Ltd	Pyrazole compounds
US4025530A (en) *	1974-05-02	1977-05-24	Abbott Laboratories	4-Nitropyrazoles

1975
- 1975-12-23 DE DE19752558117 patent/DE2558117A1/de not_active Withdrawn
1976
- 1976-11-22 US US05/744,215 patent/US4105772A/en not_active Expired - Lifetime
- 1976-12-13 CA CA267,708A patent/CA1069515A/en not_active Expired
- 1976-12-16 AR AR265884A patent/AR213107A1/es active
- 1976-12-16 ES ES454299A patent/ES454299A1/es not_active Expired
- 1976-12-16 DD DD196403A patent/DD127652A5/xx unknown
- 1976-12-17 NL NL7614011A patent/NL7614011A/xx not_active Application Discontinuation
- 1976-12-17 HU HU76BO1646A patent/HU173563B/hu unknown
- 1976-12-20 BE BE173435A patent/BE849614A/xx unknown
- 1976-12-20 CH CH1602076A patent/CH626350A5/de not_active IP Right Cessation
- 1976-12-20 GB GB53028/76A patent/GB1512763A/en not_active Expired
- 1976-12-21 AT AT950376A patent/AT353259B/de not_active IP Right Cessation
- 1976-12-21 AU AU20794/76A patent/AU502076B2/en not_active Expired
- 1976-12-22 FR FR7638654A patent/FR2336128A1/fr active Granted
- 1976-12-23 JP JP15562576A patent/JPS5283370A/ja active Pending

Also Published As

Publication number	Publication date
AT353259B (de)	1979-11-12
GB1512763A (en)	1978-06-01
JPS5283370A (en)	1977-07-12
DD127652A5 (it)	1977-10-05
ATA950376A (de)	1979-04-15
CA1069515A (en)	1980-01-08
DE2558117A1 (de)	1977-07-07
BE849614A (fr)	1977-06-20
ES454299A1 (es)	1978-02-01
US4105772A (en)	1978-08-08
AU502076B2 (en)	1979-07-12
AU2079476A (en)	1978-06-29
AR213107A1 (es)	1978-12-15
NL7614011A (nl)	1977-06-27
FR2336128A1 (fr)	1977-07-22
FR2336128B1 (it)	1979-01-19
HU173563B (hu)	1979-06-28

Publication	Publication Date	Title
DE2419970C3 (de)	1980-06-12	3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung
DE1493536B1 (de)	1971-10-14	Neue gamma-Amino-beta-phenyl-buttersaeuren
DE1793745A1 (de)	1973-05-30	Arylsubstituierte biguanide
US2851494A (en)	1958-09-09	New alpha-amino-beta-hydroxycarboxylic acid amides and a process of preparing them
CH626350A5 (it)	1981-11-13
CH653996A5 (de)	1986-01-31	Tryptaminderivate und verfahren zu deren herstellung.
WENNER et al.	1946	DERIVATIVES OF 2-PYRIDONE
US4172136A (en)	1979-10-23	3-Nitropyrazole compounds and anti-microbial compositions
AT244333B (de)	1965-12-27	Verfahren zur Herstellung von neuen Pyrrolderivaten
DE1543295C3 (de)	1978-05-18	N-substituierte Anthranilsäuren, deren Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Arzneimittel
DE1493536C (de)	1972-05-18	Neue gamma-Amino-beta-phenyl-buttersäuren
DE1801312C (de)	1972-09-14	2 (4 Biphenylyloxy)-heptansaure, ihre Alkali und Erdalkahsalze und diese Verbin düngen enthaltene Arzneimittel
AT238170B (de)	1965-01-25	Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen
DE1493854C (de)	1971-12-30	Benzanilide und Verfahren zu ihrer Herstellung
AT376417B (de)	1984-11-26	Verfahren zur herstellung von phenylaethanolaminen und ihren salzen
AT236958B (de)	1964-11-25	Verfahren zur Herstellung von neuen 5-Phenyl-2-hydroxy-6-amino-pyrimidinderivaten
CH498830A (de)	1970-11-15	Verfahren zur Herstellung von Hydrazinosäuren
DE1770420C3 (de)	1976-02-19	Verfahren zur Herstellung von 1,3-Dihydro-2H-1,4-benzodiazepin-2-onderivaten
AT278787B (de)	1970-02-10	Verfahren zur herstellung von neuen carbonsaeuren und von deren salzen
AT211296B (de)	1960-09-26	Verfahren zur Herstellung von neuen Sulfamylanthranilsäuren
DE1187236B (de)	1965-02-18	Verfahren zur Herstellung von 17beta-Aminosteroiden
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DE880444C (de)	1953-06-22	Verfahren zur Herstellung von Chinolinabkoemmlingen
AT211816B (de)	1960-11-10	Verfahren zur Herstellung von neuen polyjodierten Benzoylverbindungen
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