FI69306C - Foerfarande foer framstaellning av antikonvulsiv 2-(3-(4-(3-klor-4-fluorfenyl)-1-piperazinyl)propyl)-1,2,4-triazolo(4,3-a)pyridin-3(2h)-on - Google Patents
Foerfarande foer framstaellning av antikonvulsiv 2-(3-(4-(3-klor-4-fluorfenyl)-1-piperazinyl)propyl)-1,2,4-triazolo(4,3-a)pyridin-3(2h)-on Download PDFInfo
- Publication number
- FI69306C FI69306C FI811000A FI811000A FI69306C FI 69306 C FI69306 C FI 69306C FI 811000 A FI811000 A FI 811000A FI 811000 A FI811000 A FI 811000A FI 69306 C FI69306 C FI 69306C
- Authority
- FI
- Finland
- Prior art keywords
- compounds
- chloro
- triazolo
- propyl
- pyridin
- Prior art date
Links
- -1 3-CHLORO-4-FLUOROPHENYL Chemical class 0.000 title description 4
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical class [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims description 10
- 230000002082 anti-convulsion Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- XZFRYYHZODSXRL-UHFFFAOYSA-N 2-[3-[bis(2-chloroethyl)amino]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=CC=CN2C(=O)N(CCCN(CCCl)CCCl)N=C21 XZFRYYHZODSXRL-UHFFFAOYSA-N 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 29
- 230000000694 effects Effects 0.000 description 12
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 11
- 229960003991 trazodone Drugs 0.000 description 11
- YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 206010010904 Convulsion Diseases 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 239000001961 anticonvulsive agent Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000001773 anti-convulsant effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 230000001143 conditioned effect Effects 0.000 description 5
- 230000002936 tranquilizing effect Effects 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 229960003965 antiepileptics Drugs 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002775 capsule Substances 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
- 238000011156 evaluation Methods 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 229960005152 pentetrazol Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- BKQVYAICJGAANI-UHFFFAOYSA-N 2-[3-[4-(3-chloro-4-fluorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one Chemical compound C1=C(Cl)C(F)=CC=C1N1CCN(CCCN2C(N3C=CC=CC3=N2)=O)CC1 BKQVYAICJGAANI-UHFFFAOYSA-N 0.000 description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 2
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 241001279009 Strychnos toxifera Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001800 adrenalinergic effect Effects 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 229940125681 anticonvulsant agent Drugs 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 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
- 238000004519 manufacturing process Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000001242 postsynaptic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229960005453 strychnine Drugs 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- 101710178035 Chorismate synthase 2 Proteins 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 102100036988 Cyclin-dependent kinase 2-interacting protein Human genes 0.000 description 1
- 101710152694 Cysteine synthase 2 Proteins 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
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- 101000737869 Homo sapiens Cyclin-dependent kinase 2-interacting protein Proteins 0.000 description 1
- 238000012773 Laboratory assay Methods 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 206010027646 Miosis Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010034759 Petit mal epilepsy Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000001090 anti-dopaminergic effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940080861 demerol Drugs 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 230000004771 dopaminergic neurodegeneration Effects 0.000 description 1
- 238000007877 drug screening Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000314 lubricant 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
- 239000002609 medium Substances 0.000 description 1
- 229950002475 mesilate Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000003547 miosis Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 229960000482 pethidine Drugs 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001256 tonic effect Effects 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21246/80A IT1147349B (it) | 1980-04-09 | 1980-04-09 | 2-parentesi quadra aperta 3-parentesi quadra aperta 4-(3-cloro-4-fluorofenil)-1-piperfrazinil parentesi quadra propil parentesi quadra chiusa-1,2,4-triazolo parentesi quadra aperta 4,3 parentesi quadra chiusa piridin-3(2h)-one |
| IT2124680 | 1980-04-09 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI811000L FI811000L (fi) | 1981-10-10 |
| FI69306B FI69306B (fi) | 1985-09-30 |
| FI69306C true FI69306C (fi) | 1986-01-10 |
Family
ID=11178966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI811000A FI69306C (fi) | 1980-04-09 | 1981-04-01 | Foerfarande foer framstaellning av antikonvulsiv 2-(3-(4-(3-klor-4-fluorfenyl)-1-piperazinyl)propyl)-1,2,4-triazolo(4,3-a)pyridin-3(2h)-on |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4402956A (de) |
| JP (1) | JPS56158784A (de) |
| KR (1) | KR840002292B1 (de) |
| AR (1) | AR225076A1 (de) |
| AT (1) | AT377262B (de) |
| AU (1) | AU529605B2 (de) |
| BE (1) | BE887547A (de) |
| CA (1) | CA1176253A (de) |
| CH (1) | CH652397A5 (de) |
| DE (1) | DE3112984A1 (de) |
| ES (1) | ES8202817A1 (de) |
| FI (1) | FI69306C (de) |
| FR (1) | FR2480285A1 (de) |
| GB (1) | GB2073747B (de) |
| GR (1) | GR73620B (de) |
| IL (1) | IL62101A (de) |
| IT (1) | IT1147349B (de) |
| NL (1) | NL8100998A (de) |
| PT (1) | PT72813B (de) |
| SE (1) | SE442201B (de) |
| YU (1) | YU83181A (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001504121A (ja) * | 1996-11-12 | 2001-03-27 | セプラコール，インク． | ２ｒ，４ｓ，ｒ，ｓ―および２ｓ，４ｒ，ｒ，ｓ―ヒドロキシイトラコナゾール―およびヒドロキシサパーコナゾール誘導体 |
| WO1998021204A1 (en) | 1996-11-12 | 1998-05-22 | Sepracor, Inc. | 2r,4s,s,s- and 2s,4r,s,s-hydroxyitraconazole |
| US6147077A (en) * | 1999-04-29 | 2000-11-14 | Sepracor Inc. | 2R,4S-hydroxyitraconazole isomers |
| WO2009149347A1 (en) * | 2008-06-05 | 2009-12-10 | President And Fellows Of Harvard College | High-valent palladium fluoride complexes and uses thereof |
| WO2010059943A2 (en) | 2008-11-20 | 2010-05-27 | President And Fellows Of Harvard College | Fluorination of organic compounds |
| JP2012514655A (ja) * | 2009-01-09 | 2012-06-28 | プレジデント アンド フェローズ オブ ハーバード カレッジ | フッ素含有化合物およびその使用法 |
| EP2697204B1 (de) | 2011-04-12 | 2017-03-08 | President and Fellows of Harvard College | Fluorierung organischer verbindungen |
| WO2014052622A1 (en) | 2012-09-26 | 2014-04-03 | President And Fellows Of Harvard College | Nickel fluorinating complexes and uses thereof |
| US10759764B2 (en) | 2013-10-18 | 2020-09-01 | President And Fellows Of Harvard College | Fluorination of organic compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1066857B (it) * | 1965-12-15 | 1985-03-12 | Acraf | Derivati della s ipiazolo 4.3 a piridina e processi per la loro preparazione |
| FR8135M (de) * | 1968-12-31 | 1970-08-10 | ||
| US4267179A (en) * | 1978-06-23 | 1981-05-12 | Janssen Pharmaceutica, N.V. | Heterocyclic derivatives of (4-phenylpiperazin-1-yl-aryloxymethyl-1,3-dioxolan-2-yl)methyl-1H-imidazoles and 1H-1,2,4-triazoles |
| UST100505I4 (en) | 1980-03-17 | 1981-04-07 | Triazolo[4,3-a]pyridin-3(2H)-ones |
-
1980
- 1980-04-09 IT IT21246/80A patent/IT1147349B/it active
-
1981
- 1981-02-10 IL IL62101A patent/IL62101A/xx unknown
- 1981-02-12 US US06/234,065 patent/US4402956A/en not_active Expired - Fee Related
- 1981-02-17 BE BE0/203815A patent/BE887547A/fr not_active IP Right Cessation
- 1981-02-25 CH CH1240/81A patent/CH652397A5/it not_active IP Right Cessation
- 1981-03-02 NL NL8100998A patent/NL8100998A/nl not_active Application Discontinuation
- 1981-03-16 GB GB8108158A patent/GB2073747B/en not_active Expired
- 1981-03-30 CA CA000374133A patent/CA1176253A/en not_active Expired
- 1981-03-30 YU YU00831/81A patent/YU83181A/xx unknown
- 1981-04-01 DE DE19813112984 patent/DE3112984A1/de not_active Withdrawn
- 1981-04-01 SE SE8102093A patent/SE442201B/sv not_active IP Right Cessation
- 1981-04-01 FI FI811000A patent/FI69306C/fi not_active IP Right Cessation
- 1981-04-02 AU AU69043/81A patent/AU529605B2/en not_active Ceased
- 1981-04-07 GR GR64614A patent/GR73620B/el unknown
- 1981-04-07 PT PT72813A patent/PT72813B/pt unknown
- 1981-04-07 FR FR8106952A patent/FR2480285A1/fr active Granted
- 1981-04-07 AR AR284885A patent/AR225076A1/es active
- 1981-04-07 KR KR1019810001166A patent/KR840002292B1/ko not_active Expired
- 1981-04-08 ES ES501188A patent/ES8202817A1/es not_active Expired
- 1981-04-09 AT AT0165081A patent/AT377262B/de not_active IP Right Cessation
- 1981-04-09 JP JP5420581A patent/JPS56158784A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI811000L (fi) | 1981-10-10 |
| CA1176253A (en) | 1984-10-16 |
| BE887547A (fr) | 1981-06-15 |
| SE442201B (sv) | 1985-12-09 |
| GB2073747B (en) | 1983-09-07 |
| PT72813B (en) | 1982-04-02 |
| SE8102093L (sv) | 1981-10-10 |
| YU83181A (en) | 1983-12-31 |
| IL62101A (en) | 1984-01-31 |
| ATA165081A (de) | 1984-07-15 |
| AT377262B (de) | 1985-02-25 |
| US4402956A (en) | 1983-09-06 |
| AU529605B2 (en) | 1983-06-16 |
| AR225076A1 (es) | 1982-02-15 |
| ES501188A0 (es) | 1982-02-01 |
| CH652397A5 (it) | 1985-11-15 |
| AU6904381A (en) | 1981-10-15 |
| PT72813A (en) | 1981-05-01 |
| GB2073747A (en) | 1981-10-21 |
| KR840002292B1 (ko) | 1984-12-15 |
| IT1147349B (it) | 1986-11-19 |
| JPS56158784A (en) | 1981-12-07 |
| NL8100998A (nl) | 1981-11-02 |
| FR2480285A1 (fr) | 1981-10-16 |
| IL62101A0 (en) | 1981-03-31 |
| DE3112984A1 (de) | 1981-12-24 |
| ES8202817A1 (es) | 1982-02-01 |
| FI69306B (fi) | 1985-09-30 |
| GR73620B (de) | 1984-03-26 |
| KR830005218A (ko) | 1983-08-03 |
| FR2480285B1 (de) | 1984-02-24 |
| IT8021246A0 (it) | 1980-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AZIENDE CHIMICHE RIUNITE ANGELINI |