DE2232038A1 - 3-amino-1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine, ihre herstellung und verwendung - Google Patents
3-amino-1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine, ihre herstellung und verwendungInfo
- Publication number
- DE2232038A1 DE2232038A1 DE2232038A DE2232038A DE2232038A1 DE 2232038 A1 DE2232038 A1 DE 2232038A1 DE 2232038 A DE2232038 A DE 2232038A DE 2232038 A DE2232038 A DE 2232038A DE 2232038 A1 DE2232038 A1 DE 2232038A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- weight
- parts
- amino
- hal
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title description 2
- -1 hydroxylamino Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 18
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 125000000101 thioether group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000005457 ice water Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 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 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- LSPMHHJCDSFAAY-UHFFFAOYSA-N 2,6-dichloro-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(Cl)=C1C#N LSPMHHJCDSFAAY-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical class CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- UFOWSKDSKOEEON-UHFFFAOYSA-N 2,6-dibromopyridine-3-carbonitrile Chemical class BrC1=CC=C(C#N)C(Br)=N1 UFOWSKDSKOEEON-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- OMQUELHMHMORKS-UHFFFAOYSA-N 2-chloro-n-ethylaniline Chemical compound CCNC1=CC=CC=C1Cl OMQUELHMHMORKS-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- BFHKYHMCIAMQIN-UHFFFAOYSA-N 2-hydroxy-6-oxo-1h-pyridine-3-carbonitrile Chemical class OC=1NC(=O)C=CC=1C#N BFHKYHMCIAMQIN-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical class N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- XGYKKVTZDQDYJQ-UHFFFAOYSA-N 4-aminobutanenitrile Chemical compound NCCCC#N XGYKKVTZDQDYJQ-UHFFFAOYSA-N 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 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
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical group CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- NSBIQPJIWUJBBX-UHFFFAOYSA-N n-methoxyaniline Chemical compound CONC1=CC=CC=C1 NSBIQPJIWUJBBX-UHFFFAOYSA-N 0.000 description 1
- WCTNVGNEUDTSOZ-UHFFFAOYSA-N n-methyl-1-(3-methylphenyl)methanamine Chemical compound CNCC1=CC=CC(C)=C1 WCTNVGNEUDTSOZ-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 1
- IYPZRUYMFDWKSS-UHFFFAOYSA-N piperazin-1-amine Chemical compound NN1CCNCC1 IYPZRUYMFDWKSS-UHFFFAOYSA-N 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 150000005230 pyrazolo[3,4-b]pyridines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N pyrrolidin-1-amine Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
- C09B44/14—1,2-Diazoles or hydrogenated 1,2-diazoles ; Pyrazolium; Indazolium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232038A DE2232038A1 (de) | 1972-06-30 | 1972-06-30 | 3-amino-1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine, ihre herstellung und verwendung |
| NL7308793A NL7308793A (xx) | 1972-06-30 | 1973-06-25 | |
| US373766A US3872133A (en) | 1972-06-30 | 1973-06-26 | 3-amino-1h-pyrazolo(3,4-b)pyridines |
| CH937573A CH590279A5 (xx) | 1972-06-30 | 1973-06-27 | |
| AT568373A AT333758B (de) | 1972-06-30 | 1973-06-28 | Verfahren zur herstellung von neuen 3-amino-1h-pyrazolo (3,4-b) pyridinen |
| JP48072993A JPS4949991A (xx) | 1972-06-30 | 1973-06-29 | |
| GB3120773A GB1391244A (en) | 1972-06-30 | 1973-06-29 | 3-amino-1h-pyrazolo-3,4-b-pyridines and a process for their preparation |
| FR7323937A FR2190824B1 (xx) | 1972-06-30 | 1973-06-29 | |
| BE133019A BE801795A (fr) | 1972-06-30 | 1973-07-02 | 3-amino-1h-pyrazolo (3,4-b)pyridines, leur preparation et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232038A DE2232038A1 (de) | 1972-06-30 | 1972-06-30 | 3-amino-1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine, ihre herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2232038A1 true DE2232038A1 (de) | 1974-01-10 |
Family
ID=5849251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2232038A Pending DE2232038A1 (de) | 1972-06-30 | 1972-06-30 | 3-amino-1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine, ihre herstellung und verwendung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3872133A (xx) |
| JP (1) | JPS4949991A (xx) |
| AT (1) | AT333758B (xx) |
| BE (1) | BE801795A (xx) |
| CH (1) | CH590279A5 (xx) |
| DE (1) | DE2232038A1 (xx) |
| FR (1) | FR2190824B1 (xx) |
| GB (1) | GB1391244A (xx) |
| NL (1) | NL7308793A (xx) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2366290A1 (fr) * | 1976-09-29 | 1978-04-28 | Thomae Gmbh Dr K | Nouvelles 1h-pyrazolo (3,4-b) pyridines, leur preparation et medicaments les renfermant |
| US4264603A (en) * | 1980-03-17 | 1981-04-28 | Sterling Drug Inc. | 5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridine-3-amines, their use as cardiotonics and their preparation |
| FR2478098A1 (fr) * | 1980-03-17 | 1981-09-18 | Sterling Drug Inc | Pyrazolopyridinones et pyridinylnicotinates, leur preparation et leur utilisation comme agents cardiotoniques |
| US8846673B2 (en) | 2009-08-11 | 2014-09-30 | Bristol-Myers Squibb Company | Azaindazoles as kinase inhibitors and use thereof |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5163193A (ja) * | 1974-11-26 | 1976-06-01 | Yoshitomi Pharmaceutical | Tetorahidoropirazoropirijinkagobutsuno seizoho |
| US4020072A (en) * | 1976-05-04 | 1977-04-26 | E. R. Squibb & Sons, Inc. | 5-Aminomethyl-1H-pyrazolo[3,4-b]pyridines |
| US4361568A (en) * | 1981-04-28 | 1982-11-30 | Sterling Drug Inc. | 5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridin-3-amines and their cardiotonic use |
| JP2009506006A (ja) * | 2005-08-25 | 2009-02-12 | エフ．ホフマン−ラ ロシュ アーゲー | ｐ３８ＭＡＰキナーゼ阻害剤およびその使用方法 |
| US8742106B2 (en) | 2009-12-21 | 2014-06-03 | Novartis Ag | Disubstituted heteroaryl-fused pyridines |
| BR112020022442A2 (pt) * | 2018-05-02 | 2021-02-09 | Jw Pharmaceutical Corporation | novo derivado heterocíclico |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3733328A (en) * | 1971-11-04 | 1973-05-15 | Squibb & Sons Inc | Pyrazolo(3,4-b)pyridine-5-carboxamides |
-
1972
- 1972-06-30 DE DE2232038A patent/DE2232038A1/de active Pending
-
1973
- 1973-06-25 NL NL7308793A patent/NL7308793A/xx unknown
- 1973-06-26 US US373766A patent/US3872133A/en not_active Expired - Lifetime
- 1973-06-27 CH CH937573A patent/CH590279A5/xx not_active IP Right Cessation
- 1973-06-28 AT AT568373A patent/AT333758B/de not_active IP Right Cessation
- 1973-06-29 JP JP48072993A patent/JPS4949991A/ja active Pending
- 1973-06-29 GB GB3120773A patent/GB1391244A/en not_active Expired
- 1973-06-29 FR FR7323937A patent/FR2190824B1/fr not_active Expired
- 1973-07-02 BE BE133019A patent/BE801795A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2366290A1 (fr) * | 1976-09-29 | 1978-04-28 | Thomae Gmbh Dr K | Nouvelles 1h-pyrazolo (3,4-b) pyridines, leur preparation et medicaments les renfermant |
| US4264603A (en) * | 1980-03-17 | 1981-04-28 | Sterling Drug Inc. | 5-(Pyridinyl)-1H-pyrazolo[3,4-b]pyridine-3-amines, their use as cardiotonics and their preparation |
| FR2478098A1 (fr) * | 1980-03-17 | 1981-09-18 | Sterling Drug Inc | Pyrazolopyridinones et pyridinylnicotinates, leur preparation et leur utilisation comme agents cardiotoniques |
| FR2478100A1 (fr) * | 1980-03-17 | 1981-09-18 | Sterling Drug Inc | Derives de pyrazolopyridine, leur preparation et leur utilisation comme agents cardiotoniques |
| US8846673B2 (en) | 2009-08-11 | 2014-09-30 | Bristol-Myers Squibb Company | Azaindazoles as kinase inhibitors and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AT333758B (de) | 1976-12-10 |
| FR2190824A1 (xx) | 1974-02-01 |
| JPS4949991A (xx) | 1974-05-15 |
| GB1391244A (en) | 1975-04-16 |
| NL7308793A (xx) | 1974-01-02 |
| BE801795A (fr) | 1974-01-02 |
| CH590279A5 (xx) | 1977-07-29 |
| FR2190824B1 (xx) | 1976-11-12 |
| US3872133A (en) | 1975-03-18 |
| ATA568373A (de) | 1976-04-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0136730A1 (de) | 2-Aminonitropyridinderivate und Verfahren zu ihrer Herstellung | |
| DE2232038A1 (de) | 3-amino-1h-pyrazolo eckige klammer auf 3,4-b eckige klammer zu pyridine, ihre herstellung und verwendung | |
| DE2518587C2 (de) | Verfahren zur Herstellung basischer Oxazinfarbstoffe | |
| CH534687A (de) | Verfahren zur Herstellung von Derivaten des 2-Oxo-1,2-dihydro-chinolins | |
| DE1251765B (de) | Verfahren zur Herstellung von neuen 5H - Dihydrothiopyrano [4 3 d] pynmidinen | |
| DE2258239A1 (de) | Zimtsaeure- und dihydrozimtsaeurederivate und verfahren zu ihrer herstellung | |
| CH638203A5 (en) | Process for preparing substituted aminoquinazoline derivatives | |
| EP0044423B1 (de) | Triazolidin-3,5-dion-Salze und ihre Verwendung zum Modifizieren oder Flammfestausrüsten von Polymeren | |
| DE2335332A1 (de) | 1-hydroxy-2-(substituierte-anilino) chinoliziniumbromide | |
| DE2701677A1 (de) | Verfahren zur herstellung von organischen verbindungen | |
| EP0065717B1 (de) | Verfahren zur Herstellung kationischer Hydrazonfarbstoffe | |
| DE2912343A1 (de) | Verfahren zur herstellung von 3-aminoacrylnitrilen aus metallsalzen von 3-hydroxyacrylnitrilen | |
| DE2038182A1 (de) | Diamino- und Dinitro-s-triazine | |
| EP0014899A1 (de) | Verfahren zur Herstellung kationischer Anthrachinon-Farbstoffe | |
| DE2135584A1 (en) | 1, 3-diaminopropanes for pharmaceutical side chains - from vinylogous amidinium salts and sodium borohydrides | |
| DE2436032A1 (de) | Neue aromatische o-hydroxyaldehyde, verfahren zu ihrer herstellung und ihre verwendung | |
| DE937606C (de) | Verfahren zur Herstellung von Trimethincyanin-Farbstoffen | |
| DE1670542C (de) | Substituierte 2 Anihno4 morpholino 6 piperazino s triazine | |
| DE1470173C (de) | 1 geschweifte Klammer auf 3 ge schweifte Klammer auf eckige Klammer auf 5,6,7,8 Tetrahydro 4 (arylazo) 1 naphthyl eckige Klammer zu amino geschweifte Klammer zu propyl geschweifte Klammer zu piperi dinverbindungen, deren Saureadditionssalze sowie Verfahren zu ihrer Herstellung | |
| DE899194C (de) | Verfahren zur Herstellung von Dihydrofuran- bzw. Dihydrothiophenchinolinverbindungen | |
| AT223301B (de) | Verfahren zur Herstellung basischer Hydrazonfarbstoffe | |
| AT250338B (de) | Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen | |
| AT235279B (de) | Verfahren zur Herstellung neuer 5-Nitrofurfuryliden-hydrazine | |
| DE1670542B1 (de) | Substituierte 2-Anilino-4-morpholino-6-piperazino-s-triazine | |
| AT274819B (de) | Verfahren zur Herstellung von neuen Pteridinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |