NO126453B - - Google Patents
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- Publication number
- NO126453B NO126453B NO4220/70*[A NO422070A NO126453B NO 126453 B NO126453 B NO 126453B NO 422070 A NO422070 A NO 422070A NO 126453 B NO126453 B NO 126453B
- Authority
- NO
- Norway
- Prior art keywords
- piperidone
- alkyl
- general formula
- methyl
- residue
- Prior art date
Links
- -1 heterocyclic carboxylic acids Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 230000001549 tubercolostatic effect Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- GXXCAAXPGAHUCY-UHFFFAOYSA-N n-[(1-methylpiperidin-4-ylidene)amino]pyridine-4-carboxamide Chemical compound C1CN(C)CCC1=NNC(=O)C1=CC=NC=C1 GXXCAAXPGAHUCY-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229940072185 drug for treatment of tuberculosis Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- FFSYVIDGSCVZTP-UHFFFAOYSA-N n-[(1-ethylpiperidin-4-ylidene)amino]pyridine-4-carboxamide Chemical compound C1CN(CC)CCC1=NNC(=O)C1=CC=NC=C1 FFSYVIDGSCVZTP-UHFFFAOYSA-N 0.000 description 2
- AHBKAFFZDZKOJS-UHFFFAOYSA-N n-[(1-propan-2-ylpiperidin-4-ylidene)amino]pyridine-4-carboxamide Chemical compound C1CN(C(C)C)CCC1=NNC(=O)C1=CC=NC=C1 AHBKAFFZDZKOJS-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 201000008827 tuberculosis Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MJQSJKCAAAPORW-UHFFFAOYSA-N (1-methylpiperidin-4-ylidene)hydrazine Chemical compound CN1CCC(=NN)CC1 MJQSJKCAAAPORW-UHFFFAOYSA-N 0.000 description 1
- BDVKAMAALQXGLM-UHFFFAOYSA-N 1-ethylpiperidin-4-one Chemical compound CCN1CCC(=O)CC1 BDVKAMAALQXGLM-UHFFFAOYSA-N 0.000 description 1
- CCDBCHAQIXKJCG-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-one Chemical compound CC(C)N1CCC(=O)CC1 CCDBCHAQIXKJCG-UHFFFAOYSA-N 0.000 description 1
- YEXDIMRBZSWMPX-UHFFFAOYSA-N 2-hydroxy-n-[(1-methylpiperidin-4-ylidene)amino]benzamide Chemical compound C1CN(C)CCC1=NNC(=O)C1=CC=CC=C1O YEXDIMRBZSWMPX-UHFFFAOYSA-N 0.000 description 1
- XSXYESVZDBAKKT-UHFFFAOYSA-N 2-hydroxybenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1O XSXYESVZDBAKKT-UHFFFAOYSA-N 0.000 description 1
- UGWULZWUXSCWPX-UHFFFAOYSA-N 2-sulfanylideneimidazolidin-4-one Chemical compound O=C1CNC(=S)N1 UGWULZWUXSCWPX-UHFFFAOYSA-N 0.000 description 1
- WPBZMCGPFHZRHJ-UHFFFAOYSA-N 4-aminobenzohydrazide Chemical compound NNC(=O)C1=CC=C(N)C=C1 WPBZMCGPFHZRHJ-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 description 1
- FKZXYJYTUSGIQE-UHFFFAOYSA-N 4-nitrobenzohydrazide Chemical compound NNC(=O)C1=CC=C([N+]([O-])=O)C=C1 FKZXYJYTUSGIQE-UHFFFAOYSA-N 0.000 description 1
- KVDNEAVAJYMPBY-UHFFFAOYSA-N 5-sulfanylidene-1,2-dihydrotriazin-6-one Chemical class SC1=CN=NNC1=O KVDNEAVAJYMPBY-UHFFFAOYSA-N 0.000 description 1
- 241000304886 Bacilli Species 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010028347 Muscle twitching Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S13/00—Systems using the reflection or reradiation of radio waves, e.g. radar systems; Analogous systems using reflection or reradiation of waves whose nature or wavelength is irrelevant or unspecified
- G01S13/02—Systems using reflection of radio waves, e.g. primary radar systems; Analogous systems
- G01S13/06—Systems determining position data of a target
- G01S13/08—Systems for measuring distance only
- G01S13/10—Systems for measuring distance only using transmission of interrupted, pulse modulated waves
- G01S13/18—Systems for measuring distance only using transmission of interrupted, pulse modulated waves wherein range gates are used
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01S—RADIO DIRECTION-FINDING; RADIO NAVIGATION; DETERMINING DISTANCE OR VELOCITY BY USE OF RADIO WAVES; LOCATING OR PRESENCE-DETECTING BY USE OF THE REFLECTION OR RERADIATION OF RADIO WAVES; ANALOGOUS ARRANGEMENTS USING OTHER WAVES
- G01S7/00—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00
- G01S7/02—Details of systems according to groups G01S13/00, G01S15/00, G01S17/00 of systems according to group G01S13/00
- G01S7/28—Details of pulse systems
- G01S7/285—Receivers
- G01S7/34—Gain of receiver varied automatically during pulse-recurrence period, e.g. anti-clutter gain control
Landscapes
- Engineering & Computer Science (AREA)
- Radar, Positioning & Navigation (AREA)
- Remote Sensing (AREA)
- Computer Networks & Wireless Communication (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Radar Systems Or Details Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Optical Radar Systems And Details Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE15233/69A SE336816B (pl) | 1969-11-06 | 1969-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126453B true NO126453B (pl) | 1973-02-05 |
Family
ID=20300348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4220/70*[A NO126453B (pl) | 1969-11-06 | 1970-11-05 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3725925A (pl) |
| CH (1) | CH517946A (pl) |
| DK (1) | DK130558B (pl) |
| FR (1) | FR2073332B1 (pl) |
| GB (1) | GB1276830A (pl) |
| NL (1) | NL7016290A (pl) |
| NO (1) | NO126453B (pl) |
| SE (1) | SE336816B (pl) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3975729A (en) * | 1957-05-31 | 1976-08-17 | Aeronutronic Ford Corporation | Target detecting system |
| DE2456162C2 (de) * | 1974-11-28 | 1982-12-23 | Diehl GmbH & Co, 8500 Nürnberg | Geschoßzünder mit einer optoelektronischen Meßeinrichtung |
| US20070085727A1 (en) * | 2005-10-19 | 2007-04-19 | Honeywell International Inc. | Methods and systems for leakage cancellation in radar equipped munitions |
| JP4188361B2 (ja) * | 2005-11-22 | 2008-11-26 | 三菱電機株式会社 | 車載用パルスレーダ装置 |
| JPWO2007122873A1 (ja) * | 2006-04-20 | 2009-09-03 | アンリツ株式会社 | 短パルスレーダ及びその制御方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2474875A (en) * | 1943-01-22 | 1949-07-05 | Sperry Corp | Pulse echo volume compensating system |
| US2782412A (en) * | 1952-05-13 | 1957-02-19 | Sperry Rand Corp | Gated video integrator radar system |
| US2927319A (en) * | 1957-01-16 | 1960-03-01 | Philco Corp | Short range radar system |
| US3174148A (en) * | 1961-07-25 | 1965-03-16 | Parsons Co Ralph M | Proximity measuring system |
| US3353179A (en) * | 1966-02-16 | 1967-11-14 | Babcock Electronics Corp | Distance indicating radio apparatus |
-
1969
- 1969-11-06 SE SE15233/69A patent/SE336816B/xx unknown
-
1970
- 1970-11-04 CH CH1633770A patent/CH517946A/de not_active IP Right Cessation
- 1970-11-04 US US00086800A patent/US3725925A/en not_active Expired - Lifetime
- 1970-11-05 DK DK563270AA patent/DK130558B/da not_active IP Right Cessation
- 1970-11-05 GB GB52764/70A patent/GB1276830A/en not_active Expired
- 1970-11-05 NO NO4220/70*[A patent/NO126453B/no unknown
- 1970-11-06 NL NL7016290A patent/NL7016290A/xx unknown
- 1970-11-06 FR FR7039992A patent/FR2073332B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7016290A (pl) | 1971-05-10 |
| US3725925A (en) | 1973-04-03 |
| DK130558C (pl) | 1975-08-04 |
| SE336816B (pl) | 1971-07-19 |
| FR2073332A1 (pl) | 1971-10-01 |
| CH517946A (de) | 1972-01-15 |
| DK130558B (da) | 1975-03-03 |
| GB1276830A (en) | 1972-06-07 |
| DE2055250B2 (de) | 1976-01-22 |
| DE2055250A1 (de) | 1972-05-04 |
| FR2073332B1 (pl) | 1975-01-10 |
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