DD245874A5 - Verfahren zur herstellung fluorierter benzyltriazolverbindungen - Google Patents

Verfahren zur herstellung fluorierter benzyltriazolverbindungen Download PDF

Info

Publication number: DD245874A5
Authority: DD; German Democratic Republic
Prior art keywords: triazole; item; carbamyl; formula; produces
Prior art date: 1985-04-18

Application number

DD86289243A

Other languages

German (de)

English (en)

Inventor

Rene Meier

Original Assignee

��`��@��k��

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.)

1985-04-18

Filing date

1986-04-16

Publication date

1987-05-20

1986-04-16 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1987-05-20 Publication of DD245874A5 publication Critical patent/DD245874A5/de

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KUFNEMCYFOJAGR-UHFFFAOYSA-N 4-benzyl-2h-triazole Chemical class C=1C=CC=CC=1CC1=CNN=N1 KUFNEMCYFOJAGR-UHFFFAOYSA-N 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 65
238000000034 method Methods 0.000 claims abstract description 51
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 48
239000001257 hydrogen Substances 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 19
229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
239000011737 fluorine Substances 0.000 claims abstract description 14
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 10
229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
125000001589 carboacyl group Chemical group 0.000 claims abstract description 8
125000001118 alkylidene group Chemical group 0.000 claims abstract description 7
150000003973 alkyl amines Chemical class 0.000 claims abstract description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
-1 2,6-difluorophenyl Chemical group 0.000 claims description 54
239000000203 mixture Substances 0.000 claims description 21
150000002431 hydrogen Chemical class 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
DJBPPAUNFOJQJT-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=C(C(=O)N)N=NN1CC1=C(F)C=CC=C1F DJBPPAUNFOJQJT-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
REQQDJGYRQVUEY-UHFFFAOYSA-N 1-[(2,5-difluorophenyl)methyl]triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=C(C(=O)N)N=NN1CC1=CC(F)=CC=C1F REQQDJGYRQVUEY-UHFFFAOYSA-N 0.000 claims description 3
UUGJJIXRRVZNNX-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-5-methyltriazole-4-carboxamide Chemical compound CC1=C(C(N)=O)N=NN1CC1=C(F)C=CC=C1F UUGJJIXRRVZNNX-UHFFFAOYSA-N 0.000 claims description 3
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
POGQSBRIGCQNEG-UHFFFAOYSA-N rufinamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1F POGQSBRIGCQNEG-UHFFFAOYSA-N 0.000 claims description 3
ZUZAISZPNMFDNK-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)methyl]triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=C(C(=O)N)N=NN1CC1=CC=CC(F)=C1F ZUZAISZPNMFDNK-UHFFFAOYSA-N 0.000 claims description 2
OVOGQGWKYZSKHB-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)methyl]triazole-4-carboxamide Chemical compound N1=NC(C(=O)N)=CN1CC1=CC=CC(F)=C1F OVOGQGWKYZSKHB-UHFFFAOYSA-N 0.000 claims description 2
VTODDLDPFCXAJU-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=C(C(=O)N)N=NN1CC1=CC=C(F)C=C1F VTODDLDPFCXAJU-UHFFFAOYSA-N 0.000 claims description 2
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
WHUKCZBXOMMJIU-UHFFFAOYSA-N 1-[1-(2,6-difluorophenyl)ethyl]triazole-4-carboxamide Chemical compound C1=C(C(N)=O)N=NN1C(C)C1=C(F)C=CC=C1F WHUKCZBXOMMJIU-UHFFFAOYSA-N 0.000 claims 2
RYIYZDSRGWJEGQ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=C(C(=O)N)N=NN1CC1=C(F)C=CC=C1Cl RYIYZDSRGWJEGQ-UHFFFAOYSA-N 0.000 claims 1
YGJSCFVQYUIZMC-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]triazole-4-carboxamide Chemical compound N1=NC(C(=O)N)=CN1CC1=C(F)C=CC=C1Cl YGJSCFVQYUIZMC-UHFFFAOYSA-N 0.000 claims 1
MRJJQAVHEGLQJJ-UHFFFAOYSA-N n-formylacetamide Chemical compound CC(=O)NC=O MRJJQAVHEGLQJJ-UHFFFAOYSA-N 0.000 claims 1
230000001773 anti-convulsant effect Effects 0.000 abstract description 7
239000003814 drug Substances 0.000 abstract description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 44
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
239000000243 solution Substances 0.000 description 16
239000007858 starting material Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
241000699666 Mus <mouse, genus> Species 0.000 description 10
239000002253 acid Substances 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000001961 anticonvulsive agent Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
125000004093 cyano group Chemical group *C#N 0.000 description 6
JSZUBPHMRHROHZ-UHFFFAOYSA-N 2-(azidomethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CN=[N+]=[N-] JSZUBPHMRHROHZ-UHFFFAOYSA-N 0.000 description 5
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 5
239000004480 active ingredient Substances 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
229960003965 antiepileptics Drugs 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000008101 lactose Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000454 talc Substances 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
235000012222 talc Nutrition 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
150000008064 anhydrides Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000000926 separation method Methods 0.000 description 4
BFUIERXAICVUAH-UHFFFAOYSA-N 2-(2-azidopropan-2-yl)-1,3-difluorobenzene Chemical compound [N-]=[N+]=NC(C)(C)C1=C(F)C=CC=C1F BFUIERXAICVUAH-UHFFFAOYSA-N 0.000 description 3
FFCSQJRDCQEBGZ-UHFFFAOYSA-N 2-(azidomethyl)-1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1CN=[N+]=[N-] FFCSQJRDCQEBGZ-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
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 3
229920002472 Starch Polymers 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
238000007098 aminolysis reaction Methods 0.000 description 3
238000005915 ammonolysis reaction Methods 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
239000008116 calcium stearate Substances 0.000 description 3
235000013539 calcium stearate Nutrition 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
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235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
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RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
SIYWDKQSSDBLOA-UHFFFAOYSA-N 1-(2,6-difluorophenyl)ethanol Chemical compound CC(O)C1=C(F)C=CC=C1F SIYWDKQSSDBLOA-UHFFFAOYSA-N 0.000 description 2
BSKYMXVRPQKKNE-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-5-methyltriazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)N=NN1CC1=C(F)C=CC=C1F BSKYMXVRPQKKNE-UHFFFAOYSA-N 0.000 description 2
VYWRVJMXJSWKDJ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]triazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1CC1=C(F)C=CC=C1Cl VYWRVJMXJSWKDJ-UHFFFAOYSA-N 0.000 description 2
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MJGOLNNLNQQIHR-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1CCl MJGOLNNLNQQIHR-UHFFFAOYSA-N 0.000 description 2
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125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
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125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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229910052500 inorganic mineral Inorganic materials 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
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125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD86289243A 1985-04-18 1986-04-16 Verfahren zur herstellung fluorierter benzyltriazolverbindungen DD245874A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH166385		1985-04-18

Publications (1)

Publication Number	Publication Date
DD245874A5 true DD245874A5 (de)	1987-05-20

Family

ID=4215715

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86289243A DD245874A5 (de)	1985-04-18	1986-04-16	Verfahren zur herstellung fluorierter benzyltriazolverbindungen

Country Status (22)

Country	Link
EP (1)	EP0199262B1 (fr)
JP (1)	JPS61243068A (fr)
KR (1)	KR900008810B1 (fr)
AU (1)	AU599024B2 (fr)
CA (1)	CA1272201A (fr)
CY (1)	CY1751A (fr)
DD (1)	DD245874A5 (fr)
DE (1)	DE3677626D1 (fr)
DK (1)	DK169720B1 (fr)
ES (2)	ES8800176A1 (fr)
FI (1)	FI93544C (fr)
GR (1)	GR861004B (fr)
HK (1)	HK1494A (fr)
HU (1)	HU203327B (fr)
IE (1)	IE58472B1 (fr)
IL (1)	IL78510A (fr)
MX (1)	MX9203628A (fr)
NO (1)	NO164295C (fr)
NZ (1)	NZ215871A (fr)
PH (1)	PH22568A (fr)
PT (1)	PT82400B (fr)
ZA (1)	ZA862873B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3578499D1 (de) *	1984-02-02	1990-08-09	Merck & Co Inc	5-(amino oder substituiertes amino)-1,2,3-triazole.
AU2633897A (en) *	1996-04-19	1997-11-12	Novo Nordisk A/S	Solid phase and combinatorial synthesis of substituted 1,2,3-triazoles and of arrays of substituted 1,2,3-triazoles
SK283990B6 (sk) *	1996-07-11	2004-07-07	Novartis Ag	Spôsob prípravy 1-substituovaných 4-kyano-1,2,3-triazolov, 4-kyano-1-(2,6-difluórbenzyl)-1H-1,2,3-triazol
TW526195B (en)	1997-06-10	2003-04-01	Novartis Ag	Crystal modifications of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide and their use
TW513301B (en) *	1999-03-01	2002-12-11	Novartis Ag	Pharmaceutical composition for treatment of neuropathic pain and affective and attention disorders
WO2004106329A2 (fr) *	2003-06-03	2004-12-09	Dr. Reddy's Laboratories Ltd.	Nouveaux composes anti-infectieux et compositions pharmaceutiques les contenant
IT1393368B1 (it) *	2009-03-23	2012-04-20	Dipharma Francis Srl	Metodo per la preparazione di rufinamide
IT1395736B1 (it)	2009-08-04	2012-10-19	Dipharma Francis Srl	Forme cristalline di rufinamide
US8884026B2 (en) *	2010-04-30	2014-11-11	Laboratorios Lesvi, S.L.	Process for preparing rufinamide intermediate
ITMI20110718A1 (it)	2011-04-29	2012-10-30	Dipharma Francis Srl	Procedimento per la purificazione di rufinamide
WO2014120994A1 (fr) *	2013-01-31	2014-08-07	The Johns Hopkins University	Rufinamide et dérivés et leur utilisation pour moduler le processus de dépendance des canaux sodiques voltage-dépendants humains
US9771335B2 (en) *	2015-07-31	2017-09-26	The Johns Hopkins University	Derivatives of rufinamide and their use in inhibtion of the activation of human voltage-gated sodium channels
JP7016169B2 (ja)	2015-12-11	2022-02-04	オーフスウニベルシテット	筋強直症の治療における使用のためのルフィナミド
WO2021099481A1 (fr)	2019-11-20	2021-05-27	Medichem, S.A.	Composition solide contenant du rufinamide
CN116874438A (zh) *	2023-06-02	2023-10-13	大连理工大学	一锅法制备多取代1,2,3-三唑类化合物
CN116854644B (zh) *	2023-07-06	2025-10-21	浙江大学	5-氨基-1-烷基-1h-1,2,3-三氮唑-4-甲酰胺类化合物及其制备和应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1511195A (en) *	1976-10-18	1978-05-17	Ici America Inc	Triazole derivatives
FI834666A7 (fi) *	1982-12-23	1984-06-24	Ciba Geigy Ag	Foerfarande foer framstaellning av nya aralkyltriazolfoereningar.

1986
- 1986-04-14 PH PH33651A patent/PH22568A/en unknown
- 1986-04-14 FI FI861573A patent/FI93544C/fi not_active IP Right Cessation
- 1986-04-15 DE DE8686105188T patent/DE3677626D1/de not_active Expired - Lifetime
- 1986-04-15 IL IL78510A patent/IL78510A/xx not_active IP Right Cessation
- 1986-04-15 EP EP86105188A patent/EP0199262B1/fr not_active Expired - Lifetime
- 1986-04-16 GR GR861004A patent/GR861004B/el unknown
- 1986-04-16 DD DD86289243A patent/DD245874A5/de not_active IP Right Cessation
- 1986-04-16 CA CA000506774A patent/CA1272201A/fr not_active Expired - Lifetime
- 1986-04-16 NO NO861486A patent/NO164295C/no unknown
- 1986-04-16 PT PT82400A patent/PT82400B/pt unknown
- 1986-04-16 ES ES554024A patent/ES8800176A1/es not_active Expired
- 1986-04-17 DK DK175686A patent/DK169720B1/da not_active IP Right Cessation
- 1986-04-17 AU AU56319/86A patent/AU599024B2/en not_active Expired
- 1986-04-17 ZA ZA862873A patent/ZA862873B/xx unknown
- 1986-04-17 HU HU861615A patent/HU203327B/hu unknown
- 1986-04-17 KR KR1019860002954A patent/KR900008810B1/ko not_active Expired
- 1986-04-17 IE IE101586A patent/IE58472B1/en not_active IP Right Cessation
- 1986-04-17 NZ NZ215871A patent/NZ215871A/xx unknown
- 1986-04-18 JP JP61088384A patent/JPS61243068A/ja active Granted
1987
- 1987-07-31 ES ES557641A patent/ES8802501A1/es not_active Expired
1992
- 1992-06-26 MX MX9203628A patent/MX9203628A/es unknown
1994
- 1994-01-06 HK HK14/94A patent/HK1494A/xx not_active IP Right Cessation
- 1994-06-03 CY CY175194A patent/CY1751A/xx unknown

Also Published As

Publication number	Publication date
ES8802501A1 (es)	1988-07-01
EP0199262B1 (fr)	1991-02-27
AU5631986A (en)	1986-10-23
DK169720B1 (da)	1995-01-23
KR860008152A (ko)	1986-11-12
HK1494A (en)	1994-01-14
NO861486L (no)	1986-10-20
HU203327B (en)	1991-07-29
GR861004B (en)	1986-08-12
MX9203628A (es)	1992-09-01
IE58472B1 (en)	1993-09-22
DE3677626D1 (de)	1991-04-04
IE861015L (en)	1986-10-18
CY1751A (en)	1994-06-03
PT82400A (en)	1986-05-01
FI861573A0 (fi)	1986-04-14
EP0199262A2 (fr)	1986-10-29
CA1272201A (fr)	1990-07-31
NZ215871A (en)	1989-01-27
AU599024B2 (en)	1990-07-12
ES557641A0 (es)	1988-07-01
PT82400B (pt)	1988-08-17
ZA862873B (en)	1986-12-30
FI93544C (fi)	1995-04-25
DK175686A (da)	1986-10-19
IL78510A (en)	1992-05-25
KR900008810B1 (ko)	1990-11-30
NO164295B (no)	1990-06-11
DK175686D0 (da)	1986-04-17
JPS61243068A (ja)	1986-10-29
FI93544B (fi)	1995-01-13
FI861573A7 (fi)	1986-10-19
HUT40792A (en)	1987-02-27
ES554024A0 (es)	1987-10-16
ES8800176A1 (es)	1987-10-16
NO164295C (no)	1990-09-19
IL78510A0 (en)	1986-08-31
PH22568A (en)	1988-10-17
JPH0564949B2 (fr)	1993-09-16
EP0199262A3 (en)	1987-08-26

Legal Events

Date	Code	Title	Description
1996-03-28	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3781845T2 (de)	1993-02-18	Benzimidazol-derivate.
EP0004920B1 (fr)	1981-08-05	Dérivés de la carbazolyl-4-oxypropanolamine, procédés pour leur préparation et médicaments les contenant
DE69021502T2 (de)	1996-01-11	Benzimidazolderivate, Verfahren zu deren Herstellung und Anwendung.
EP0199262B1 (fr)	1991-02-27	Composés benzyltriazole fluorés
DE3241102A1 (de)	1984-05-10	Imidazolylalkylthienyl-tetrahydropyridazine und verfahren zu ihrer herstellung
DE2933649A1 (de)	1980-03-13	Imidazolderivate, sie enthaltende pharmazeutische zusammensetzungen
DE2855836C2 (fr)	1989-09-28
EP0414019B1 (fr)	1996-05-29	N-(Quinoléine-2-yl-méthoxy)benzylsulfonylurées substituées
DE3830060A1 (de)	1990-03-15	2-phenylbenzimidazole - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel
DE69719511T2 (de)	2003-10-02	Antivirale 2,4-pyrimidindion-derivate und verfahren zu ihrer herstellung
WO1988001268A1 (fr)	1988-02-25	Derives d'imidazole
DE19945594A1 (de)	2001-03-29	Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel
DE4316117A1 (de)	1993-11-25	Cycloheptimidazol-Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende, therapeutische Mittel
DE68903263T2 (de)	1993-05-19	Substituierte aromatische verbindungen mit zentraler nervensystem-wirkung.
DD216456A5 (de)	1984-12-12	Verfahren zur herstellung neuer aralkyltriazolverbindungen
DE2819873C2 (fr)	1989-05-03
EP0248414B1 (fr)	1992-09-23	Dérivés d'aralkylimidazole
EP0267147B1 (fr)	1991-08-07	Dérivés d'aralkyl-4H-1,2,4-triazole
DE4220983A1 (de)	1994-01-05	Imidazolyl-substituierte Phenylpropion- und -zimtsäurederivate
CH643821A5 (de)	1984-06-29	Substituierte phenylacetylguanidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate.
DE1908496A1 (de)	1969-09-18	Neue Thiophenderivate und Verfahren zu ihrer Herstellung
DD234005A5 (de)	1986-03-19	Verfahren zur herstellung neuer 1,2,4-triazacycloalkadienderivate
DD210266A5 (de)	1984-06-06	Verfahren zur herstellung von 3-(ureidocyclohexylamino)-propan-1,2-diolderivaten
DD260928A5 (de)	1988-10-12	Verfahren zur herstellung neuer aralkylimidizolderivate
DE60130684T2 (de)	2008-08-14	Substituierte pyrrolidine als ccr-3-rezeptorantagonisten