CA1048499A - Derives halogenes du pyrazole, methode de production desdits derives et des medicaments qui les contiennent - Google Patents

Derives halogenes du pyrazole, methode de production desdits derives et des medicaments qui les contiennent

Info

Publication number: CA1048499A
Authority: CA; Canada
Prior art keywords: phenyl; pyrazole; chloro; chlorophenyl; acetic acid
Prior art date: 1973-08-16
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

Application number

CA74207072A

Other languages

English (en)

Other versions

CA207072S (en

Inventor

Georg Rainer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda GmbH

Original Assignee

Byk Gulden Lomberg Chemische Fabrik 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.)

1973-08-16

Filing date

1974-08-15

Publication date

1979-02-13

1974-08-15 Application filed by Byk Gulden Lomberg Chemische Fabrik GmbH filed Critical Byk Gulden Lomberg Chemische Fabrik GmbH

1979-02-13 Application granted granted Critical

1979-02-13 Publication of CA1048499A publication Critical patent/CA1048499A/fr

Status Expired legal-status Critical Current

Links

-1 Halogen pyrazoles derivatives Chemical class 0.000 title claims abstract description 64
239000003814 drug Substances 0.000 title abstract description 25
229910052736 halogen Inorganic materials 0.000 title abstract description 20
238000004519 manufacturing process Methods 0.000 title abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 34
229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
239000000460 chlorine Substances 0.000 claims abstract description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
239000011737 fluorine Substances 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 52
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 claims description 44
150000001875 compounds Chemical class 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
230000008569 process Effects 0.000 claims description 32
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
PXWJTOHJADWQQO-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)acetic acid Chemical class OC(=O)CC=1C=NNC=1 PXWJTOHJADWQQO-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 9
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 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
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 claims description 5
159000000000 sodium salts Chemical class 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
150000002780 morpholines Chemical class 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
YZZPERWLJOWEAN-UHFFFAOYSA-N 2-(5-chloro-1,3-diphenylpyrazol-4-yl)acetonitrile Chemical compound ClC1=C(CC#N)C(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 YZZPERWLJOWEAN-UHFFFAOYSA-N 0.000 claims 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 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
125000005277 alkyl imino group Chemical group 0.000 claims description 3
125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
WTLNBJZSVMLAKP-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)acetamide Chemical compound NC(=O)CC=1C=NNC=1 WTLNBJZSVMLAKP-UHFFFAOYSA-N 0.000 claims 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 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims 13
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 11
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
125000005059 halophenyl group Chemical group 0.000 claims 2
HWEJDOAPQGNKAE-UHFFFAOYSA-N 2-(1h-pyrazol-4-yl)acetonitrile Chemical compound N#CCC=1C=NNC=1 HWEJDOAPQGNKAE-UHFFFAOYSA-N 0.000 claims 1
KVCSOWNJRXZHGH-UHFFFAOYSA-N 2-[5-bromo-3-(4-methoxyphenyl)-1-phenylpyrazol-4-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=NN(C=2C=CC=CC=2)C(Br)=C1CC#N KVCSOWNJRXZHGH-UHFFFAOYSA-N 0.000 claims 1
SGSBELJZAGJRNU-UHFFFAOYSA-N 2-[5-chloro-3-[4-(2-methylpropyl)phenyl]-1-phenylpyrazol-4-yl]acetic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=NN(C=2C=CC=CC=2)C(Cl)=C1CC(O)=O SGSBELJZAGJRNU-UHFFFAOYSA-N 0.000 claims 1
JKTRFQIKHPHVSJ-UHFFFAOYSA-N 2-[5-chloro-3-[4-(2-methylpropyl)phenyl]-1-phenylpyrazol-4-yl]acetonitrile Chemical compound C1=CC(CC(C)C)=CC=C1C1=NN(C=2C=CC=CC=2)C(Cl)=C1CC#N JKTRFQIKHPHVSJ-UHFFFAOYSA-N 0.000 claims 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
150000002367 halogens Chemical class 0.000 abstract description 12
239000013543 active substance Substances 0.000 abstract description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000000243 solution Substances 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
230000007062 hydrolysis Effects 0.000 description 18
238000006460 hydrolysis reaction Methods 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 14
230000000875 corresponding effect Effects 0.000 description 14
239000000203 mixture Substances 0.000 description 14
238000009835 boiling Methods 0.000 description 12
229940079593 drug Drugs 0.000 description 10
229910052740 iodine Inorganic materials 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
150000002825 nitriles Chemical class 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000000470 constituent Substances 0.000 description 9
229960004756 ethanol Drugs 0.000 description 9
238000003756 stirring Methods 0.000 description 9
150000002148 esters Chemical class 0.000 description 8
150000004820 halides Chemical class 0.000 description 8
239000000047 product Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
150000001408 amides Chemical class 0.000 description 7
229940076134 benzene Drugs 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
239000011574 phosphorus Substances 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
229940083608 sodium hydroxide Drugs 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
239000002775 capsule Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000008187 granular material Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
206010061218 Inflammation Diseases 0.000 description 5
208000002193 Pain Diseases 0.000 description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
230000004054 inflammatory process Effects 0.000 description 5
150000007529 inorganic bases Chemical class 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
239000000463 material Substances 0.000 description 5
230000036407 pain Effects 0.000 description 5
230000009467 reduction Effects 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
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 4
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 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-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
241000124008 Mammalia Species 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000005907 alkyl ester group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
150000001409 amidines Chemical class 0.000 description 4
230000001754 anti-pyretic effect Effects 0.000 description 4
239000002585 base Substances 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003610 charcoal Substances 0.000 description 4
229940106265 charcoal Drugs 0.000 description 4
239000000796 flavoring agent Substances 0.000 description 4
235000013355 food flavoring agent Nutrition 0.000 description 4
239000008101 lactose Substances 0.000 description 4
229960001375 lactose Drugs 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
229960005205 prednisolone Drugs 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229940032330 sulfuric acid Drugs 0.000 description 4
230000001225 therapeutic effect Effects 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
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
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VTMRUCPYIZOTGK-UHFFFAOYSA-N 5-chloro-3-(4-chlorophenyl)-1-phenylpyrazole-4-carbaldehyde Chemical compound ClC1=C(C=O)C(C=2C=CC(Cl)=CC=2)=NN1C1=CC=CC=C1 VTMRUCPYIZOTGK-UHFFFAOYSA-N 0.000 description 3
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 3
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 3
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150000003556 thioamides Chemical class 0.000 description 3
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239000000080 wetting agent Substances 0.000 description 3
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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
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235000013343 vitamin Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 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)

CA74207072A 1973-08-16 1974-08-15 Derives halogenes du pyrazole, methode de production desdits derives et des medicaments qui les contiennent Expired CA1048499A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU68238A LU68238A1 (fr)	1973-08-16	1973-08-16

Publications (1)

Publication Number	Publication Date
CA1048499A true CA1048499A (fr)	1979-02-13

Family

ID=19727442

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA74207072A Expired CA1048499A (fr)	1973-08-16	1974-08-15	Derives halogenes du pyrazole, methode de production desdits derives et des medicaments qui les contiennent

Country Status (18)

Country	Link
JP (1)	JPS5230515B2 (fr)
AT (1)	AT339892B (fr)
BE (1)	BE818912A (fr)
CA (1)	CA1048499A (fr)
CH (1)	CH601250A5 (fr)
DE (2)	DE2462459C3 (fr)
DK (1)	DK136953B (fr)
ES (1)	ES429247A1 (fr)
FI (1)	FI57584C (fr)
FR (1)	FR2240732B1 (fr)
GB (1)	GB1475806A (fr)
IE (1)	IE39999B1 (fr)
LU (1)	LU68238A1 (fr)
NL (1)	NL169070C (fr)
NO (1)	NO140733C (fr)
SE (1)	SE409454B (fr)
YU (1)	YU222474A (fr)
ZA (1)	ZA745252B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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 FR FR7428162A patent/FR2240732B1/fr not_active Expired
- 1974-08-14 GB GB3574074A patent/GB1475806A/en not_active Expired
- 1974-08-14 ES ES429247A patent/ES429247A1/es not_active Expired
- 1974-08-14 YU YU02224/74A patent/YU222474A/xx unknown
- 1974-08-14 CH CH1111874A patent/CH601250A5/xx not_active IP Right Cessation
- 1974-08-15 FI FI2422/74A patent/FI57584C/fi active
- 1974-08-15 CA CA74207072A patent/CA1048499A/fr not_active Expired
- 1974-08-15 IE IE1705/74A patent/IE39999B1/xx unknown
- 1974-08-15 JP JP49093786A patent/JPS5230515B2/ja not_active Expired
- 1974-08-15 DK DK438174AA patent/DK136953B/da unknown
- 1974-08-15 NL NLAANVRAGE7410921,A patent/NL169070C/xx not_active IP Right Cessation
- 1974-08-15 ZA ZA00745252A patent/ZA745252B/xx unknown
- 1974-08-15 SE SE7410419A patent/SE409454B/xx unknown
- 1974-08-15 NO NO742941A patent/NO140733C/no unknown
- 1974-08-16 BE BE147661A patent/BE818912A/fr unknown
- 1974-08-16 AT AT671174A patent/AT339892B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
LU68238A1 (fr)	1975-05-21
NO140733B (no)	1979-07-23
DE2438779A1 (de)	1975-02-27
NL169070B (nl)	1982-01-04
DE2462459C3 (de)	1979-10-04
FI242274A7 (fr)	1975-02-17
FR2240732A1 (fr)	1975-03-14
SE409454B (sv)	1979-08-20
ZA745252B (en)	1976-03-31
DK438174A (fr)	1975-04-28
NL169070C (nl)	1982-06-01
JPS5230515B2 (fr)	1977-08-09
IE39999L (en)	1975-02-16
DE2462459B2 (de)	1979-02-08
IE39999B1 (en)	1979-02-14
YU222474A (en)	1983-04-27
ES429247A1 (es)	1976-08-16
JPS5049278A (fr)	1975-05-01
CH601250A5 (fr)	1978-06-30
BE818912A (fr)	1975-02-17
GB1475806A (en)	1977-06-10
DK136953B (da)	1977-12-19
ATA671174A (de)	1977-03-15
FI57584C (fi)	1980-09-10
FI57584B (fi)	1980-05-30
DK136953C (fr)	1978-05-29
SE7410419L (fr)	1975-02-17
NO742941L (fr)	1975-03-17
NO140733C (no)	1979-10-31
DE2438779B2 (de)	1979-01-25
FR2240732B1 (fr)	1978-07-21
DE2438779C3 (de)	1979-09-20
DE2462459A1 (de)	1977-04-07
AT339892B (de)	1977-11-10
NL7410921A (nl)	1975-02-18

Publication	Publication Date	Title
EP0731794B1 (fr)	1997-08-06	Composes du 1,4,5-triphenyle pyrazolyle destines au traitement des inflammations et des troubles lies aux inflammations
JPH07324076A (ja)	1995-12-12	新規なピラゾール−３−カルボキサミド誘導体、これらを製造するための方法及びこれらが存在する薬学的組成物
JPS58164557A (ja)	1983-09-29	新規ピリジル化合物
JPH0238591B2 (fr)	1990-08-31
US4528298A (en)	1985-07-09	Antiinflammatory imidazole derivatives
US4239901A (en)	1980-12-16	Pyrazol-1-ylphenylacetic acids
EP0000200A1 (fr)	1979-01-10	N-Amidino-3,5-diamino-6-substitué-2-pyrazinecarboxamides et procédé pour leur préparation
US4272507A (en)	1981-06-09	Phenylaminothiophenacetic acids, their synthesis, compositions and use
US3860636A (en)	1975-01-14	Substituted indenyl phosphonic acids having anti-inflammatory activity
CA1048499A (fr)	1979-02-13	Derives halogenes du pyrazole, methode de production desdits derives et des medicaments qui les contiennent
US4042702A (en)	1977-08-16	Halogen pyrazole derivatives, a method for producing these halogen pyrazole derivatives, medicaments containing and methods of using them
JPH05246980A (ja)	1993-09-24	β−オキソ−β−ベンゼンプロパンチオアミド誘導体
CA1180335A (fr)	1985-01-02	3-amino-1-aryl-2-pyrazolines
US3974176A (en)	1976-08-10	Halogen pyrazoles derivatives, a method for producing these halogen pyrazole derivatives and medicaments containing them
JPH0378854B2 (fr)	1991-12-17
JPS59512B2 (ja)	1984-01-07	ピラゾ−ル −５− オンカゴウブツノセイゾウホウホウ
JPH0372061B2 (fr)	1991-11-15
US4301167A (en)	1981-11-17	2-Amino thiazoline derivatives
NO812208L (no)	1981-12-28	Pyrimidin-derivater.
CS216205B2 (en)	1982-10-29	Method of making the derivatives of the 1,4-diphenylpyrazole
US4046896A (en)	1977-09-06	1-Methyl-2-(pyridyl-oxymethyl)-5-nitro-imidazoles
JPS58188876A (ja)	1983-11-04	抗炎症剤及び抗喘息剤
EP0011854B1 (fr)	1982-04-07	Dérivés de l'acide 4-(2'-pyridylamino)phényl-acétique, procédé pour leur préparation, compositions pharmaceutiques contenant ces composés et leur utilisation
CZ278281B6 (en)	1993-11-17	ENOL ETHER OF 1,1-DIOXIDE OF 6-CHLORO-4-HYDROXY-2-METHYL-N- (2-PYRIDYL-2H-THIENO(2,3-c)-1,2-THIAZINECARBOXYLIC ACID AMIDE, PROCESS OF ITS PREPARATION AND ITS USE
DE69509510T2 (de)	1999-09-02	2-(aminoalkoxy) phenylalkylamine mit entzündungskennenden eigenschaften