FI57584C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 5-klor- eller 5-brom-1,3-difenylpyrazol-4-aettiksyraderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 5-klor- eller 5-brom-1,3-difenylpyrazol-4-aettiksyraderivat Download PDFInfo
- Publication number
- FI57584C FI57584C FI2422/74A FI242274A FI57584C FI 57584 C FI57584 C FI 57584C FI 2422/74 A FI2422/74 A FI 2422/74A FI 242274 A FI242274 A FI 242274A FI 57584 C FI57584 C FI 57584C
- Authority
- FI
- Finland
- Prior art keywords
- chloro
- phenyl
- pyrazole
- acetic acid
- chlorophenyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 18
- 230000001225 therapeutic effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- -1 hydrocarbon radical Chemical class 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 230000007062 hydrolysis Effects 0.000 description 16
- 238000006460 hydrolysis reaction Methods 0.000 description 16
- NNCQIRVJCHUDSZ-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]acetic acid Chemical compound OC(=O)CC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 NNCQIRVJCHUDSZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 230000003110 anti-inflammatory effect Effects 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002825 nitriles Chemical class 0.000 description 7
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- PXWJTOHJADWQQO-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)acetic acid Chemical class OC(=O)CC=1C=NNC=1 PXWJTOHJADWQQO-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- BOJGVXKYCFCQDO-UHFFFAOYSA-N 2-(5-chloro-1,3-diphenylpyrazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 BOJGVXKYCFCQDO-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001409 amidines Chemical class 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 3
- CUXRLIKLLXNSAU-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]acetamide Chemical compound NC(=O)CC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 CUXRLIKLLXNSAU-UHFFFAOYSA-N 0.000 description 3
- BDUMMIGEKFWOKT-UHFFFAOYSA-N 2-[5-chloro-3-(4-methoxyphenyl)-1-phenylpyrazol-4-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C(Cl)=C1CC(O)=O BDUMMIGEKFWOKT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- KIGVUJXRSNBFES-UHFFFAOYSA-N ethyl 2-[5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]acetate Chemical compound CCOC(=O)CC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 KIGVUJXRSNBFES-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002463 imidates Chemical class 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 231100000636 lethal dose Toxicity 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003556 thioamides Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- MZKALFCNIJHTJG-UHFFFAOYSA-N 2,5-diphenyl-4h-pyrazol-3-one Chemical compound O=C1CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 MZKALFCNIJHTJG-UHFFFAOYSA-N 0.000 description 2
- SPGRKILKCPEFRF-UHFFFAOYSA-N 2-(5-bromo-1,3-diphenylpyrazol-4-yl)acetic acid Chemical compound OC(=O)CC1=C(Br)N(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 SPGRKILKCPEFRF-UHFFFAOYSA-N 0.000 description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 2
- GOYZGCTUVLVZKT-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]-n-phenylacetamide Chemical compound C=1C=C(Cl)C=CC=1C1=NN(C=2C=CC=CC=2)C(Cl)=C1CC(=O)NC1=CC=CC=C1 GOYZGCTUVLVZKT-UHFFFAOYSA-N 0.000 description 2
- DTMGVTGDNVFIDX-UHFFFAOYSA-N 2-[5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]acetonitrile Chemical compound ClC1=C(CC#N)C(C=2C=CC(Cl)=CC=2)=NN1C1=CC=CC=C1 DTMGVTGDNVFIDX-UHFFFAOYSA-N 0.000 description 2
- UDEHQFCYBZEUMZ-UHFFFAOYSA-N 2-[5-chloro-3-(4-methoxyphenyl)-1-phenylpyrazol-4-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C(Cl)=C1CC#N UDEHQFCYBZEUMZ-UHFFFAOYSA-N 0.000 description 2
- QBWPDGFMRLCTJG-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-phenyl-4h-pyrazol-3-one Chemical compound C1=CC(Cl)=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)C1 QBWPDGFMRLCTJG-UHFFFAOYSA-N 0.000 description 2
- JSJKAIQJGDEDOI-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2-phenyl-4h-pyrazol-3-one Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C(=O)C1 JSJKAIQJGDEDOI-UHFFFAOYSA-N 0.000 description 2
- LCFJVWSEZNBVPA-UHFFFAOYSA-N 5-chloro-4-(chloromethyl)-3-(4-chlorophenyl)-1-phenylpyrazole Chemical compound ClCC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 LCFJVWSEZNBVPA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- AVNSPVMYCDHHAU-UHFFFAOYSA-N [5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]methanol Chemical compound OCC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 AVNSPVMYCDHHAU-UHFFFAOYSA-N 0.000 description 2
- MDXDLWCTQWPZLI-UHFFFAOYSA-N acetic acid;1h-pyrazole Chemical class CC(O)=O.C=1C=NNC=1 MDXDLWCTQWPZLI-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000005277 alkyl imino group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- 150000002780 morpholines Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003217 pyrazoles Chemical class 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 230000009772 tissue formation Effects 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- YVHCYHBEOGCEPI-UHFFFAOYSA-N (5-bromo-1,3-diphenylpyrazol-4-yl)methanol Chemical compound OCC1=C(Br)N(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 YVHCYHBEOGCEPI-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- WTLNBJZSVMLAKP-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)acetamide Chemical class NC(=O)CC=1C=NNC=1 WTLNBJZSVMLAKP-UHFFFAOYSA-N 0.000 description 1
- GLSXYRHOWPAOFB-UHFFFAOYSA-N 2-(5-phenyl-1h-pyrazol-4-yl)acetic acid Chemical compound C1=NNC(C=2C=CC=CC=2)=C1CC(=O)O GLSXYRHOWPAOFB-UHFFFAOYSA-N 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
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- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- BGYVKTMQEQJXLN-UHFFFAOYSA-N methyl 2-[5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]acetate Chemical compound COC(=O)CC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 BGYVKTMQEQJXLN-UHFFFAOYSA-N 0.000 description 1
- UNBDDZDKBWPHAX-UHFFFAOYSA-N n,n-di(propan-2-yl)formamide Chemical compound CC(C)N(C=O)C(C)C UNBDDZDKBWPHAX-UHFFFAOYSA-N 0.000 description 1
- CVHCNGJGIBMDBU-UHFFFAOYSA-N n-butyl-2-[5-chloro-3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]acetamide Chemical compound CCCCNC(=O)CC1=C(Cl)N(C=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1 CVHCNGJGIBMDBU-UHFFFAOYSA-N 0.000 description 1
- SHJRJBMVHJTGJM-UHFFFAOYSA-N n-ethyl-n-(2-methylphenyl)formamide Chemical compound CCN(C=O)C1=CC=CC=C1C SHJRJBMVHJTGJM-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- MXXWOMGUGJBKIW-YPCIICBESA-N piperine Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCCC1 MXXWOMGUGJBKIW-YPCIICBESA-N 0.000 description 1
- 229940075559 piperine Drugs 0.000 description 1
- WVWHRXVVAYXKDE-UHFFFAOYSA-N piperine Natural products O=C(C=CC=Cc1ccc2OCOc2c1)C3CCCCN3 WVWHRXVVAYXKDE-UHFFFAOYSA-N 0.000 description 1
- 235000019100 piperine Nutrition 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
-
- 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
-
- 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU68238A LU68238A1 (de) | 1973-08-16 | 1973-08-16 | |
| LU68238 | 1973-08-16 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI242274A7 FI242274A7 (de) | 1975-02-17 |
| FI57584B FI57584B (fi) | 1980-05-30 |
| FI57584C true FI57584C (fi) | 1980-09-10 |
Family
ID=19727442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2422/74A FI57584C (fi) | 1973-08-16 | 1974-08-15 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 5-klor- eller 5-brom-1,3-difenylpyrazol-4-aettiksyraderivat |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5230515B2 (de) |
| AT (1) | AT339892B (de) |
| BE (1) | BE818912A (de) |
| CA (1) | CA1048499A (de) |
| CH (1) | CH601250A5 (de) |
| DE (2) | DE2462459C3 (de) |
| DK (1) | DK136953B (de) |
| ES (1) | ES429247A1 (de) |
| FI (1) | FI57584C (de) |
| FR (1) | FR2240732B1 (de) |
| GB (1) | GB1475806A (de) |
| IE (1) | IE39999B1 (de) |
| LU (1) | LU68238A1 (de) |
| NL (1) | NL169070C (de) |
| NO (1) | NO140733C (de) |
| SE (1) | SE409454B (de) |
| YU (1) | YU222474A (de) |
| ZA (1) | ZA745252B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5297383A (en) * | 1976-02-13 | 1977-08-16 | Ngk Spark Plug Co | Ceramic honeycomb structures for exhaust gas purification |
| HUP0304101A3 (en) * | 2003-12-22 | 2008-10-28 | Sanofi Aventis | Pyrazole derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates |
-
1973
- 1973-08-16 LU LU68238A patent/LU68238A1/xx unknown
-
1974
- 1974-08-13 DE DE2462459A patent/DE2462459C3/de not_active Expired
- 1974-08-13 DE DE2438779A patent/DE2438779C3/de not_active Expired
- 1974-08-14 YU YU02224/74A patent/YU222474A/xx unknown
- 1974-08-14 FR FR7428162A patent/FR2240732B1/fr not_active Expired
- 1974-08-14 CH CH1111874A patent/CH601250A5/xx not_active IP Right Cessation
- 1974-08-14 ES ES429247A patent/ES429247A1/es not_active Expired
- 1974-08-14 GB GB3574074A patent/GB1475806A/en not_active Expired
- 1974-08-15 ZA ZA00745252A patent/ZA745252B/xx unknown
- 1974-08-15 FI FI2422/74A patent/FI57584C/fi active
- 1974-08-15 CA CA74207072A patent/CA1048499A/en not_active Expired
- 1974-08-15 JP JP49093786A patent/JPS5230515B2/ja not_active Expired
- 1974-08-15 NL NLAANVRAGE7410921,A patent/NL169070C/xx not_active IP Right Cessation
- 1974-08-15 SE SE7410419A patent/SE409454B/xx unknown
- 1974-08-15 IE IE1705/74A patent/IE39999B1/xx unknown
- 1974-08-15 NO NO742941A patent/NO140733C/no unknown
- 1974-08-15 DK DK438174AA patent/DK136953B/da unknown
- 1974-08-16 BE BE147661A patent/BE818912A/xx unknown
- 1974-08-16 AT AT671174A patent/AT339892B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH601250A5 (de) | 1978-06-30 |
| NL169070B (nl) | 1982-01-04 |
| DE2438779C3 (de) | 1979-09-20 |
| NL7410921A (nl) | 1975-02-18 |
| JPS5049278A (de) | 1975-05-01 |
| DE2462459C3 (de) | 1979-10-04 |
| FR2240732B1 (de) | 1978-07-21 |
| GB1475806A (en) | 1977-06-10 |
| NL169070C (nl) | 1982-06-01 |
| BE818912A (fr) | 1975-02-17 |
| ES429247A1 (es) | 1976-08-16 |
| JPS5230515B2 (de) | 1977-08-09 |
| DE2438779B2 (de) | 1979-01-25 |
| DE2462459A1 (de) | 1977-04-07 |
| AT339892B (de) | 1977-11-10 |
| FI57584B (fi) | 1980-05-30 |
| YU222474A (en) | 1983-04-27 |
| SE7410419L (de) | 1975-02-17 |
| NO742941L (de) | 1975-03-17 |
| DE2438779A1 (de) | 1975-02-27 |
| CA1048499A (en) | 1979-02-13 |
| DE2462459B2 (de) | 1979-02-08 |
| ATA671174A (de) | 1977-03-15 |
| DK438174A (de) | 1975-04-28 |
| FR2240732A1 (de) | 1975-03-14 |
| FI242274A7 (de) | 1975-02-17 |
| NO140733C (no) | 1979-10-31 |
| NO140733B (no) | 1979-07-23 |
| SE409454B (sv) | 1979-08-20 |
| DK136953C (de) | 1978-05-29 |
| ZA745252B (en) | 1976-03-31 |
| LU68238A1 (de) | 1975-05-21 |
| IE39999L (en) | 1975-02-16 |
| IE39999B1 (en) | 1979-02-14 |
| DK136953B (da) | 1977-12-19 |
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