NL8100998A - Piperazinederivaat. - Google Patents

Piperazinederivaat. Download PDF

Info

Publication number: NL8100998A
Authority: NL; Netherlands
Prior art keywords: toxic salt; action; compound; compound according; amount selected
Prior art date: 1980-04-09

Application number

NL8100998A

Other languages

English (en)

Dutch (nl)

Original Assignee

Acraf

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.)

1980-04-09

Filing date

1981-03-02

Publication date

1981-11-02

1981-03-02 Application filed by Acraf filed Critical Acraf

1981-11-02 Publication of NL8100998A publication Critical patent/NL8100998A/nl

Links

GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical class C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 17
238000000034 method Methods 0.000 claims description 12
230000002082 anti-convulsion Effects 0.000 claims description 10
231100000252 nontoxic Toxicity 0.000 claims description 10
230000003000 nontoxic effect Effects 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 8
206010010904 Convulsion Diseases 0.000 claims description 7
230000000202 analgesic effect Effects 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
230000036461 convulsion Effects 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 5
150000004885 piperazines Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
230000000506 psychotropic effect Effects 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 1
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
230000004044 response Effects 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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 6
-1 3-chloro-1-fluorophenyl Chemical group 0.000 description 5
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 5
230000001143 conditioned effect Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
230000001914 calming effect Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 3
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
241001465754 Metazoa Species 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
241001279009 Strychnos toxifera Species 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
229960005152 pentetrazol Drugs 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229960005453 strychnine Drugs 0.000 description 3
239000003204 tranquilizing agent Substances 0.000 description 3
230000002936 tranquilizing effect Effects 0.000 description 3
208000019901 Anxiety 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
208000007101 Muscle Cramp Diseases 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000001800 adrenalinergic effect Effects 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
238000009835 boiling Methods 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000001965 increasing effect Effects 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
150000007530 organic bases Chemical class 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000001242 postsynaptic effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000001624 sedative effect Effects 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000001256 steam distillation Methods 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
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
MEPVQSRZSYTCPB-UHFFFAOYSA-N C1C(=CC=CC1(N)F)Cl Chemical compound C1C(=CC=CC1(N)F)Cl MEPVQSRZSYTCPB-UHFFFAOYSA-N 0.000 description 1
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
208000020401 Depressive disease Diseases 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
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
150000007513 acids Chemical class 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
230000001430 anti-depressive effect Effects 0.000 description 1
230000001090 anti-dopaminergic effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
239000000935 antidepressant agent Substances 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
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 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
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 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
239000008120 corn starch Substances 0.000 description 1
229940080861 demerol Drugs 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
230000004771 dopaminergic neurodegeneration Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000007877 drug screening Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
206010016256 fatigue Diseases 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229960003878 haloperidol Drugs 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000007774 longterm Effects 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
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
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
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
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000003518 presynaptic effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
208000018299 prostration Diseases 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
210000001747 pupil Anatomy 0.000 description 1
238000001953 recrystallisation Methods 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
230000035939 shock Effects 0.000 description 1
239000000021 stimulant 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
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 description 1
150000003512 tertiary amines Chemical class 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)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NL8100998A 1980-04-09 1981-03-02 Piperazinederivaat. NL8100998A (nl)

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 (1)

Publication Number	Publication Date
NL8100998A true NL8100998A (nl)	1981-11-02

Family

ID=11178966

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8100998A NL8100998A (nl)	1980-04-09	1981-03-02	Piperazinederivaat.

Country Status (21)

Country	Link
US (1)	US4402956A (fr)
JP (1)	JPS56158784A (fr)
KR (1)	KR840002292B1 (fr)
AR (1)	AR225076A1 (fr)
AT (1)	AT377262B (fr)
AU (1)	AU529605B2 (fr)
BE (1)	BE887547A (fr)
CA (1)	CA1176253A (fr)
CH (1)	CH652397A5 (fr)
DE (1)	DE3112984A1 (fr)
ES (1)	ES8202817A1 (fr)
FI (1)	FI69306C (fr)
FR (1)	FR2480285A1 (fr)
GB (1)	GB2073747B (fr)
GR (1)	GR73620B (fr)
IL (1)	IL62101A (fr)
IT (1)	IT1147349B (fr)
NL (1)	NL8100998A (fr)
PT (1)	PT72813B (fr)
SE (1)	SE442201B (fr)
YU (1)	YU83181A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001504465A (ja)	1996-11-12	2001-04-03	セプラコール，インク．	２ｒ，４ｓ，ｓ，ｓ―および２ｓ，４ｒ，ｓ，ｓ―ヒドロキシイトラコナゾール
CA2269617A1 (fr) *	1996-11-12	1998-05-22	Chris H. Senanayake	Derives de 2r,4s,r,s et 2s,4r,r,s-hydroxyitraconazole et hydroxysaperconazole
US6147077A (en) *	1999-04-29	2000-11-14	Sepracor Inc.	2R,4S-hydroxyitraconazole isomers
EP2303897A4 (fr) *	2008-06-05	2012-02-22	Harvard College	Complexes de fluorure de palladium de valence élevée et leurs utilisations
WO2010059943A2 (fr)	2008-11-20	2010-05-27	President And Fellows Of Harvard College	Fluoration de composés organiques
EP2385944A4 (fr) *	2009-01-09	2013-06-19	Harvard College	Composés fluorés et leurs procédés d'utilisation
CN103596931B (zh)	2011-04-12	2016-10-12	哈佛大学校长及研究员协会	有机化合物的氟化
US9273083B2 (en)	2012-09-26	2016-03-01	President And Fellows Of Harvard College	Nickel fluorinating complexes and uses thereof
WO2015058047A2 (fr)	2013-10-18	2015-04-23	President And Fellows Of Harvard College	Fluoration de composés organiques

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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 (fr) *	1968-12-31	1970-08-10
US4218458A (en) *	1978-06-23	1980-08-19	Janssen Pharmaceutica, N.V.	Heterocyclic derivatives of (4-aryloxy-methyl-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 YU YU00831/81A patent/YU83181A/xx unknown
- 1981-03-30 CA CA000374133A patent/CA1176253A/fr not_active Expired
- 1981-04-01 FI FI811000A patent/FI69306C/fi not_active IP Right Cessation
- 1981-04-01 DE DE19813112984 patent/DE3112984A1/de not_active Withdrawn
- 1981-04-01 SE SE8102093A patent/SE442201B/sv not_active IP Right Cessation
- 1981-04-02 AU AU69043/81A patent/AU529605B2/en not_active Ceased
- 1981-04-07 KR KR1019810001166A patent/KR840002292B1/ko not_active Expired
- 1981-04-07 AR AR284885A patent/AR225076A1/es active
- 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
- 1981-04-08 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
AR225076A1 (es)	1982-02-15
FI811000L (fi)	1981-10-10
ATA165081A (de)	1984-07-15
ES501188A0 (es)	1982-02-01
FI69306B (fi)	1985-09-30
GB2073747A (en)	1981-10-21
KR840002292B1 (ko)	1984-12-15
FR2480285B1 (fr)	1984-02-24
SE442201B (sv)	1985-12-09
YU83181A (en)	1983-12-31
FI69306C (fi)	1986-01-10
BE887547A (fr)	1981-06-15
PT72813B (en)	1982-04-02
US4402956A (en)	1983-09-06
IT1147349B (it)	1986-11-19
GR73620B (fr)	1984-03-26
IL62101A0 (en)	1981-03-31
GB2073747B (en)	1983-09-07
IT8021246A0 (it)	1980-04-09
PT72813A (en)	1981-05-01
ES8202817A1 (es)	1982-02-01
CA1176253A (fr)	1984-10-16
JPS56158784A (en)	1981-12-07
DE3112984A1 (de)	1981-12-24
IL62101A (en)	1984-01-31
KR830005218A (ko)	1983-08-03
FR2480285A1 (fr)	1981-10-16
AU529605B2 (en)	1983-06-16
AT377262B (de)	1985-02-25
SE8102093L (sv)	1981-10-10
AU6904381A (en)	1981-10-15
CH652397A5 (it)	1985-11-15

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-11-02	BV	The patent application has lapsed

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