IE34268L - Hydrazines and hydrazones of pyrazolopyridine carboxylic¹acids and esters. - Google Patents
Hydrazines and hydrazones of pyrazolopyridine carboxylic¹acids and esters.Info
- Publication number
- IE34268L IE34268L IE73470A IE73470A IE34268L IE 34268 L IE34268 L IE 34268L IE 73470 A IE73470 A IE 73470A IE 73470 A IE73470 A IE 73470A IE 34268 L IE34268 L IE 34268L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- phenyl
- formula
- compound
- alkoxy
- Prior art date
Links
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 150000002429 hydrazines Chemical class 0.000 title 1
- 150000007857 hydrazones Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 21
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- -1 R 5 is H Chemical group 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- 239000003599 detergent Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000005229 pyrazolopyridines Chemical class 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1317797 Pyrazolo-pyridines E R SQUIBB & SONS Inc 10 June 1970 [16 June 1969] 28164/70 Heading C2C Novel compounds of Formulµ I and II: (in which R 1 is H, alkyl or phenyl-C 1-7 alkyl, R 2 is C 1-7 alkyl, phenyl, phenyl-C 1-7 alkyl, R 6 and/or R 7 -substituted phenyl-C 1-7 alkyl or cycloalkyl-C 1-7 alkyl, R 3 is H, C 1-7 alkyl, phenyl or R 6 and/or R 7 -substituted phenyl, R 4 is H, C 1-7 alkyl, C 1-7 alkanoyl or phenyl, R 5 is H, alkyl or C 1-7 alkanoyl, each of R 6 and R 7 is halogen, C 1-7 alkyl or C 1-7 alkoxy, X is H, C 1-7 alkyl, C 1-7 hydroxyalkyl, phenyl, R 6 - and/or R 7 - substituted phenyl, phenyl-C 1-7 alkyl or R 6 and/or R 7 -substituted phenyl-C 1-7 alkyl, Y is C 1-7 alkyl, C 1-7 hydroxyalkyl, phenyl, R 6 and/or R 7 -substituted phenyl, phenyl-C 1-7 alkyl or R 6 and/or R 7 -substituted phenyl-C 1-7 alkyl or X and Y together with the adjacent carbon atom represent cycloalkylidene or 5-nitro-2- furylidene) and acid addition salts thereof, are prepared by reacting a compound of Formula III: (in which R<SP>1</SP> is Cl, OH, C 1-7 alkoxy or phenyl- C 1-7 alkoxy) with a hydrazine of formula H 2 N.NR 4 R 5 , or a salt thereof, to form a product of Formula I, and, if desired, when R 4 and R 5 in the product are both H, reacting the product with a carbonyl compound of formula XYC = O to form a product of Formula II, and optionally converting either of said products to an acid addition salt thereof. Compounds I in which R 4 is H and R 5 is C 2-7 alkyl may also be prepared by reduction of appropriately substituted compounds II. Compounds of Formula III are prepared by reacting a compound of Formula IV: with a compound of Formula V: (in which R 1 is C 1-7 alkyl or phenyl-C 1-7 alkyl) to give a compound of Formula VI: cyclizing this to give a compound III in which R<SP>1</SP> is OH and R 1 is C 1-7 alkyl or phenyl-C 1-7 alkyl, and, if desired, hydrolysing the ester group to the free acid group and/or converting the OH group to a chlorine atom or an alkoxy group. Pharmaceutical and disinfectant compositions comprise one of the above novel compounds together with a carrier. The pharmaceutical compositions may be used as antibacterial agents, as tranquillizers and in the relief of asthma, and may be in a form suitable for oral, topical or parenteral administration. The compositions may be in the form of a soap or detergent.
[GB1317797A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83367269A | 1969-06-16 | 1969-06-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34268L true IE34268L (en) | 1970-12-16 |
| IE34268B1 IE34268B1 (en) | 1975-03-19 |
Family
ID=25264992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE73470A IE34268B1 (en) | 1969-06-16 | 1970-06-08 | Hydrazines and hydrazones of pyrazolopyridine carboxylic acids and esters |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS518957B1 (en) |
| CA (1) | CA924721A (en) |
| CH (1) | CH525227A (en) |
| DE (1) | DE2028869A1 (en) |
| DK (1) | DK137241B (en) |
| GB (1) | GB1317797A (en) |
| HU (1) | HU162876B (en) |
| IE (1) | IE34268B1 (en) |
| NL (1) | NL165461C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669950A (en) * | 1970-12-01 | 1972-06-13 | Squibb & Sons Inc | DIPYRAZOLO{8 3,4-b:3,4d{9 -PYRIDIN-3-ONES |
| PL200923B1 (en) | 1999-08-21 | 2009-02-27 | Nycomed Gmbh | SYNERGISTIC COMBINATION OF PDE INHIBITORS AND ß₂ ADRENOCEPTOR AGONIST |
-
1970
- 1970-06-05 CA CA084791A patent/CA924721A/en not_active Expired
- 1970-06-08 IE IE73470A patent/IE34268B1/en unknown
- 1970-06-10 GB GB2816470A patent/GB1317797A/en not_active Expired
- 1970-06-11 DE DE19702028869 patent/DE2028869A1/de not_active Withdrawn
- 1970-06-15 DK DK307770A patent/DK137241B/en unknown
- 1970-06-15 HU HUSU000544 patent/HU162876B/hu unknown
- 1970-06-16 JP JP5228970A patent/JPS518957B1/ja active Pending
- 1970-06-16 CH CH913470A patent/CH525227A/en not_active IP Right Cessation
- 1970-06-16 NL NL7008768A patent/NL165461C/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK137241B (en) | 1978-02-06 |
| DE2028869A1 (en) | 1970-12-23 |
| NL7008768A (en) | 1970-12-18 |
| NL165461C (en) | 1981-04-15 |
| IE34268B1 (en) | 1975-03-19 |
| GB1317797A (en) | 1973-05-23 |
| NL165461B (en) | 1980-11-17 |
| HU162876B (en) | 1973-04-28 |
| JPS518957B1 (en) | 1976-03-22 |
| CA924721A (en) | 1973-04-17 |
| CH525227A (en) | 1972-07-15 |
| DK137241C (en) | 1978-07-10 |
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