CS208115B2 - Method of making the imidazolylethoxyderivatives of the pyrazolo 3,4-b-pyridin-5-methanols - Google Patents

Method of making the imidazolylethoxyderivatives of the pyrazolo 3,4-b-pyridin-5-methanols Download PDF

Info

Publication number: CS208115B2
Authority: CS; Czechoslovakia
Prior art keywords: pyrazolo; ethyl; methyl; formula; pyridine
Prior art date: 1978-07-10

Application number

CS794480A

Other languages

Czech (cs)

English (en)

Inventor

Hans Hoehn

Original Assignee

Squibb & Sons Inc

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.)

1978-07-10

Filing date

1979-06-28

Publication date

1981-08-31

1979-06-28 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1981-08-31 Publication of CS208115B2 publication Critical patent/CS208115B2/cs

Links

238000004519 manufacturing process Methods 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 18
-1 Imidazolylethoxy derivatives of pyrazolo-[3,4-b]pyridine-5-methanols Chemical class 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims description 16
239000012458 free base Substances 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
229940121375 antifungal agent Drugs 0.000 abstract description 3
230000000843 anti-fungal effect Effects 0.000 abstract description 2
239000003429 antifungal agent Substances 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000002585 base Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
DFIHJRYVCTUJJP-UHFFFAOYSA-N 4-chloro-5-(chloromethyl)-1-ethylpyrazolo[3,4-b]pyridine Chemical compound ClCC1=CN=C2N(CC)N=CC2=C1Cl DFIHJRYVCTUJJP-UHFFFAOYSA-N 0.000 description 2
PQWBCUZPLFEUAY-UHFFFAOYSA-N 4-chloro-5-[[1-(2,4-dichlorophenyl)-2-imidazol-1-ylethoxy]methyl]-1-ethylpyrazolo[3,4-b]pyridine hydrochloride Chemical compound Cl.CCn1ncc2c(Cl)c(COC(Cn3ccnc3)c3ccc(Cl)cc3Cl)cnc12 PQWBCUZPLFEUAY-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
XKGYNDQSOFYSJR-UHFFFAOYSA-N (4-chloro-1-ethylpyrazolo[3,4-b]pyridin-5-yl)methanol Chemical compound OCC1=CN=C2N(CC)N=CC2=C1Cl XKGYNDQSOFYSJR-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
UKVLTPAGJIYSGN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)CN1C=CN=C1 UKVLTPAGJIYSGN-UHFFFAOYSA-N 0.000 description 1
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 1
NRLWKOLQCJJLJA-UHFFFAOYSA-N 4-chloro-5-[[1-(2,4-dichlorophenyl)-2-imidazol-1-ylethoxy]methyl]-1-ethyl-3-methylpyrazolo[3,4-b]pyridine hydrochloride Chemical compound Cl.CCn1nc(C)c2c(Cl)c(COC(Cn3ccnc3)c3ccc(Cl)cc3Cl)cnc12 NRLWKOLQCJJLJA-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000700198 Cavia Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
150000000994 L-ascorbates Chemical class 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
241000224527 Trichomonas vaginalis Species 0.000 description 1
241001045770 Trichophyton mentagrophytes Species 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000005352 clarification Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
230000003226 decolorizating effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
KEAYESYHFKHZAL-IGMARMGPSA-N sodium-23 atom Chemical compound [23Na] KEAYESYHFKHZAL-IGMARMGPSA-N 0.000 description 1
239000011343 solid material Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical class C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000001680 trimethoxyphenyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS794480A 1978-07-10 1979-06-28 Method of making the imidazolylethoxyderivatives of the pyrazolo 3,4-b-pyridin-5-methanols CS208115B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/923,418 US4159380A (en)	1978-07-10	1978-07-10	Imidazolylethoxy derivatives of pyrazolo[3,4-b]pyridine-5-methanols

Publications (1)

Publication Number	Publication Date
CS208115B2 true CS208115B2 (en)	1981-08-31

Family

ID=25448663

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794480A CS208115B2 (en)	1978-07-10	1979-06-28	Method of making the imidazolylethoxyderivatives of the pyrazolo 3,4-b-pyridin-5-methanols

Country Status (24)

Country	Link
US (1)	US4159380A (fr)
JP (1)	JPS5513298A (fr)
AU (1)	AU519835B2 (fr)
BE (1)	BE877600A (fr)
CS (1)	CS208115B2 (fr)
DD (1)	DD144774A5 (fr)
DE (1)	DE2927867A1 (fr)
DK (1)	DK288079A (fr)
ES (1)	ES482280A1 (fr)
FR (1)	FR2430946A1 (fr)
GB (1)	GB2024815A (fr)
GR (1)	GR73111B (fr)
IE (1)	IE48442B1 (fr)
IT (1)	IT1122056B (fr)
LU (1)	LU81477A1 (fr)
NL (1)	NL7905242A (fr)
NO (1)	NO792275L (fr)
NZ (1)	NZ190698A (fr)
PH (1)	PH14437A (fr)
PL (1)	PL216944A1 (fr)
SE (1)	SE7905987L (fr)
SU (1)	SU873884A3 (fr)
YU (1)	YU163779A (fr)
ZA (1)	ZA792908B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1097314B (it) *	1978-07-26	1985-08-31	Recordati Chem Pharm	Derivati dell'imidazolo ad attivita' anticonvulsivante
US4234589A (en) *	1979-09-24	1980-11-18	E. R. Squibb & Sons, Inc.	Imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines
US4282230A (en) *	1979-11-15	1981-08-04	E. R. Squibb & Sons, Inc.	Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them
US4248881A (en) *	1979-12-20	1981-02-03	E. R. Squibb & Sons, Inc.	Imidazolylethoxymethyl derivatives of pyrazole
US4260614A (en) *	1980-02-08	1981-04-07	E. R. Squibb & Sons, Inc.	4-(2-(1H-Imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxypyrazolo(3,4-b)pyridines
US4260616A (en) *	1980-02-14	1981-04-07	E. R. Squibb & Sons, Inc.	Antimicrobial imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU557755A3 (ru) *	1968-08-19	1977-05-05	Янссен Фармасьютика Н.В. (Фирма)	Способ получени производных имидазола
US3658813A (en) *	1970-01-13	1972-04-25	Janssen Pharmaceutica Nv	1-(beta-aryl-beta-(r-oxy)-ethyl)-imidazoles
US3928368A (en) *	1973-12-12	1975-12-23	Squibb & Sons Inc	Alcohol derivatives of pyrazolo{8 3,4-b{9 pyridines
US3983128A (en) *	1973-12-12	1976-09-28	E. R. Squibb & Sons, Inc.	Alcohol derivatives of pyrazolo[3,4-b]pyridines
US3991201A (en) *	1974-06-27	1976-11-09	Janssen Pharmaceutica N.V.	1-(β-Aryl-β-R-ethyl)imidazoles as antimicrobial agents

1978
- 1978-07-10 US US05/923,418 patent/US4159380A/en not_active Expired - Lifetime
1979
- 1979-06-11 NZ NZ190698A patent/NZ190698A/xx unknown
- 1979-06-12 ZA ZA792908A patent/ZA792908B/xx unknown
- 1979-06-12 AU AU48001/79A patent/AU519835B2/en not_active Withdrawn - After Issue
- 1979-06-13 GB GB7920516A patent/GB2024815A/en active Pending
- 1979-06-15 GR GR59358A patent/GR73111B/el unknown
- 1979-06-20 FR FR7915802A patent/FR2430946A1/fr not_active Withdrawn
- 1979-06-28 CS CS794480A patent/CS208115B2/cs unknown
- 1979-07-05 NL NL7905242A patent/NL7905242A/nl not_active Application Discontinuation
- 1979-07-05 YU YU01637/79A patent/YU163779A/xx unknown
- 1979-07-06 IT IT24171/79A patent/IT1122056B/it active
- 1979-07-06 DD DD79214181A patent/DD144774A5/de unknown
- 1979-07-06 ES ES482280A patent/ES482280A1/es not_active Expired
- 1979-07-07 PL PL21694479A patent/PL216944A1/xx unknown
- 1979-07-09 SE SE7905987A patent/SE7905987L/xx not_active Application Discontinuation
- 1979-07-09 LU LU81477A patent/LU81477A1/fr unknown
- 1979-07-09 SU SU792782862A patent/SU873884A3/ru active
- 1979-07-09 NO NO792275A patent/NO792275L/no unknown
- 1979-07-09 DK DK288079A patent/DK288079A/da unknown
- 1979-07-10 DE DE19792927867 patent/DE2927867A1/de not_active Withdrawn
- 1979-07-10 PH PH22764A patent/PH14437A/en unknown
- 1979-07-10 JP JP8800379A patent/JPS5513298A/ja active Pending
- 1979-07-10 BE BE0/196221A patent/BE877600A/fr unknown
- 1979-08-08 IE IE1277/79A patent/IE48442B1/en unknown

Also Published As

Publication number	Publication date
GB2024815A (en)	1980-01-16
LU81477A1 (fr)	1979-10-31
JPS5513298A (en)	1980-01-30
AU519835B2 (en)	1981-12-24
DK288079A (da)	1980-01-11
SE7905987L (sv)	1980-01-11
PH14437A (en)	1981-07-16
IE48442B1 (en)	1985-01-23
ZA792908B (en)	1980-06-25
AU4800179A (en)	1980-02-07
IT1122056B (it)	1986-04-23
NO792275L (no)	1980-01-11
SU873884A3 (ru)	1981-10-15
YU163779A (en)	1983-06-30
IT7924171A0 (it)	1979-07-06
US4159380A (en)	1979-06-26
FR2430946A1 (fr)	1980-02-08
NL7905242A (nl)	1980-01-14
IE791277L (en)	1980-01-10
BE877600A (fr)	1980-01-10
GR73111B (fr)	1984-02-02
DD144774A5 (de)	1980-11-05
NZ190698A (en)	1981-10-19
ES482280A1 (es)	1980-04-01
DE2927867A1 (de)	1980-01-31
PL216944A1 (fr)	1980-08-11

Publication	Publication Date	Title
US4020072A (en)	1977-04-26	5-Aminomethyl-1H-pyrazolo[3,4-b]pyridines
IE52788B1 (en)	1988-03-02	Phenoxyalkyl-1,2,4-triazol-3-one antidepressants
US4414225A (en)	1983-11-08	Azepine derivatives and their anti-thrombotic compositions and methods
DK152756B (da)	1988-05-09	Imidazokinolinderivat til anvendelse som antireproduktionsmiddel
NL193541C (nl)	2000-01-04	8 Alfa-acylaminoergolinen, werkwijzen voor de bereiding daarvan en preparaten die ze bevatten.
CS208115B2 (en)	1981-08-31	Method of making the imidazolylethoxyderivatives of the pyrazolo 3,4-b-pyridin-5-methanols
EP0151477B1 (fr)	1990-09-12	Dérivés de 1H-imidazole, un procédé pour leur préparation et compositions pharmaceutiques les contenant
US4831151A (en)	1989-05-16	Antimicrobial imidazolium derivatives
US4282230A (en)	1981-08-04	Imidazolylethoxy derivatives of quinoline-2- or 4-methanols, antimicrobial compositions containing them and method for treating bacterial or fungal infections with them
US4273776A (en)	1981-06-16	Antibacterial and antifungal derivatives of 3-(1H-imidazol-1-yl)-2-propen-1-ones
CA1142923A (fr)	1983-03-15	Acides 2-amino-8-cyclopropyl-5-oxo-5,8-dihydro-pyrido [2,3-d]-pyrimidine-6-carboxyliques, leur preparation et leur utilisation en medecine
US4234589A (en)	1980-11-18	Imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines
US4169205A (en)	1979-09-25	Imidazole derivatives of 6,11-dihydrodibenz[b,e]oxepines and 6,11-dihydrodibenz[b,e]thiepines
US4707484A (en)	1987-11-17	Substituted piperidinomethylindolone and cyclopent(b)indolone derivatives
DK158944B (da)	1990-08-06	Analogifremgangsmaade til fremstilling af substituerede methylimidazolforbindelser
US4228177A (en)	1980-10-14	2,3-Dihydro-3-(1H-imidazol-1-ylmethylene)-4H-1-benzothiopyran-4-ones
US4202985A (en)	1980-05-13	Imidazolylethoxy derivatives of quinoline-3-methanols
GB2081261A (en)	1982-02-17	Condensed as-triazine derivatives and process for preparing the same
US3919229A (en)	1975-11-11	Pyrimidine derivatives and process for preparing the same
US4191831A (en)	1980-03-04	Imidazolylethoxy derivatives of pyridin-5-methanols
NO161102B (no)	1989-03-28	Lokkemat for gnagere omfattende foede og en gift.
US4308270A (en)	1981-12-29	1,2,4-Oxadiazine derivatives, process for their preparation and pharmaceutical compositions containing them
US4260616A (en)	1981-04-07	Antimicrobial imidazolylethoxymethyl derivatives of 1,3-dioxolo quinolines
US4248878A (en)	1981-02-03	Imidazole derivatives of 1,5,6,11-tetrahydrobenzo[5,6]cyclohepta[1,2-b]pyrazolo[4,3-e]pyridines
US5064826A (en)	1991-11-12	Novel triazolo-pyrimidine derivatives