IL22306A - 4-substituted-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo(3,4-d)pyrimidines - Google Patents

4-substituted-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo(3,4-d)pyrimidines

Info

Publication number: IL22306A
Authority: IL; Israel
Prior art keywords: compound; furyl; nitro; amino; group
Prior art date: 1963-10-24

Application number

IL22306A

Other languages

English (en)

Original Assignee

Norwich Pharma Co

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.)

1963-10-24

Filing date

1964-10-21

Publication date

1968-11-27

1964-08-17 Priority claimed from US390207A external-priority patent/US3335141A/en

1964-10-21 Application filed by Norwich Pharma Co filed Critical Norwich Pharma Co

1968-11-27 Publication of IL22306A publication Critical patent/IL22306A/en

Links

150000003230 pyrimidines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 25
-1 methoxyethyl Chemical group 0.000 claims description 11
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
150000002828 nitro derivatives Chemical class 0.000 claims description 3
230000002140 halogenating effect Effects 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
230000000802 nitrating effect Effects 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
239000000243 solution Substances 0.000 description 27
238000002844 melting Methods 0.000 description 26
230000008018 melting Effects 0.000 description 26
238000001953 recrystallisation Methods 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000012043 crude product Substances 0.000 description 18
239000002904 solvent Substances 0.000 description 18
239000000203 mixture Substances 0.000 description 17
238000003756 stirring Methods 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
239000005457 ice water Substances 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
YXDXXGXWFJCXEB-UHFFFAOYSA-N 2-furonitrile Chemical compound N#CC1=CC=CO1 YXDXXGXWFJCXEB-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000002440 hydroxy compounds Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
OEICGMPRFOJHKO-UHFFFAOYSA-N 2-(ethoxymethylidene)propanedinitrile Chemical compound CCOC=C(C#N)C#N OEICGMPRFOJHKO-UHFFFAOYSA-N 0.000 description 2
IBELBRDFPCFICX-UHFFFAOYSA-N 2-methoxyethylhydrazine Chemical compound COCCNN IBELBRDFPCFICX-UHFFFAOYSA-N 0.000 description 2
UXCCGIWVLMDSPZ-UHFFFAOYSA-N 5-amino-1-ethylpyrazole-4-carbonitrile Chemical compound CCN1N=CC(C#N)=C1N UXCCGIWVLMDSPZ-UHFFFAOYSA-N 0.000 description 2
MZFBWODPTSTYAI-UHFFFAOYSA-N 5-amino-1-methylpyrazole-4-carbonitrile Chemical compound CN1N=CC(C#N)=C1N MZFBWODPTSTYAI-UHFFFAOYSA-N 0.000 description 2
TZYQTWHRLVDYPL-UHFFFAOYSA-N 5h-pyrimidin-4-one Chemical compound O=C1CC=NC=N1 TZYQTWHRLVDYPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
150000002240 furans Chemical class 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000004312 hexamethylene tetramine Substances 0.000 description 2
235000010299 hexamethylene tetramine Nutrition 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 1
RAGJERVRBJTUDD-UHFFFAOYSA-N 5-amino-1-(2-methoxyethyl)pyrazole-4-carbonitrile Chemical compound COCCN1N=CC(C#N)=C1N RAGJERVRBJTUDD-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
241000186810 Erysipelothrix rhusiopathiae Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
241000607142 Salmonella Species 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
241000193985 Streptococcus agalactiae Species 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Inspection Of Paper Currency And Valuable Securities (AREA)

IL22306A 1963-10-24 1964-10-21 4-substituted-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo(3,4-d)pyrimidines IL22306A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US31850263A	1963-10-24	1963-10-24
US390207A US3335141A (en)	1964-08-17	1964-08-17	4-substituted-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo[3, 4-d]pyrimidines

Publications (1)

Publication Number	Publication Date
IL22306A true IL22306A (en)	1968-11-27

Family

ID=26981516

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL22306A IL22306A (en)	1963-10-24	1964-10-21	4-substituted-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo(3,4-d)pyrimidines

Country Status (13)

Country	Link
AT (1)	AT254195B (fr)
BE (1)	BE654663A (fr)
BR (1)	BR6463641D0 (fr)
CH (1)	CH460035A (fr)
DE (1)	DE1470138A1 (fr)
DK (1)	DK104743C (fr)
ES (1)	ES305118A1 (fr)
FR (2)	FR4032M (fr)
GB (1)	GB1089615A (fr)
IL (1)	IL22306A (fr)
NL (1)	NL6412365A (fr)
NO (1)	NO115392B (fr)
SE (1)	SE312341B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2004713A1 (de) *	1970-02-03	1971-08-12	Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof	Nitrofuryl triazolo pyrimidine und Verfahren zu ihrer Herstellung

1964
- 1964-10-20 ES ES0305118A patent/ES305118A1/es not_active Expired
- 1964-10-20 CH CH1357864A patent/CH460035A/de unknown
- 1964-10-20 AT AT891664A patent/AT254195B/de active
- 1964-10-21 BE BE654663A patent/BE654663A/xx unknown
- 1964-10-21 DE DE19641470138 patent/DE1470138A1/de active Pending
- 1964-10-21 IL IL22306A patent/IL22306A/en unknown
- 1964-10-22 GB GB43207/64A patent/GB1089615A/en not_active Expired
- 1964-10-22 BR BR163641/64A patent/BR6463641D0/pt unknown
- 1964-10-23 NL NL6412365A patent/NL6412365A/xx unknown
- 1964-10-23 NO NO155272A patent/NO115392B/no unknown
- 1964-10-23 FR FR992452A patent/FR4032M/fr not_active Expired
- 1964-10-23 DK DK524564AA patent/DK104743C/da active
- 1964-10-23 FR FR992451A patent/FR1453243A/fr not_active Expired
- 1964-10-23 SE SE12771/64A patent/SE312341B/xx unknown

Also Published As

Publication number	Publication date
AT254195B (de)	1967-05-10
DK104743C (da)	1966-06-27
ES305118A1 (es)	1965-02-01
CH460035A (de)	1968-07-31
BR6463641D0 (pt)	1973-07-17
SE312341B (fr)	1969-07-14
NL6412365A (fr)	1965-04-26
DE1470138A1 (de)	1969-06-04
NO115392B (fr)	1968-09-30
GB1089615A (en)	1967-11-01
BE654663A (fr)	1965-02-15
FR1453243A (fr)	1966-06-03
FR4032M (fr)	1966-03-28

Publication	Publication Date	Title
AU683224B2 (en)	1997-11-06	Insecticidal N'-substituted-N,N'-diacylhydrazines
US3896131A (en)	1975-07-22	Substituted benzo(ij)quinolizine-2-carboxylic acids and derivatives thereof
EP0520240A1 (fr)	1992-12-30	Dérivés carboxyliques de 7-isoindolinyl-chinolone et naphthylridone
Avan et al.	2013	Synthesis and antimicrobial investigation of some 5H-pyridazino [4, 5-b] indoles
US3350397A (en)	1967-10-31	4-amino-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo [3, 4-d] pyrimidines
SU475768A3 (ru)	1975-06-30	Способ получени (5-нитрофурил-2) -пиридинов
US3335141A (en)	1967-08-08	4-substituted-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo[3, 4-d]pyrimidines
IL22306A (en)	1968-11-27	4-substituted-1-alkyl-6-(5-nitro-2-furyl)-1h-pyrazolo(3,4-d)pyrimidines
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RU2109014C1 (ru)	1998-04-20	Производные фторхинолин-3-карбоновой кислоты и способ их получения
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