CH404688A - Verfahren zur Herstellung von 2-Acylhydrazino-5-nitrosotroponen - Google Patents

Verfahren zur Herstellung von 2-Acylhydrazino-5-nitrosotroponen

Info

Publication number: CH404688A
Authority: CH; Switzerland
Prior art keywords: nitrosotropon; acid hydrazide; log; analysis; calculated
Prior art date: 1960-12-17

Application number

CH1453661A

Other languages

German (de)

English (en)

Inventor

Sunagawa Genshun

Arakawa Masao

Sato Yasunobu

Minakami Haruhiko

Original Assignee

Sankyo 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.)

1960-12-17

Filing date

1961-12-15

Publication date

1965-12-31

1961-12-15 Application filed by Sankyo Co filed Critical Sankyo Co

1965-12-31 Publication of CH404688A publication Critical patent/CH404688A/de

Links

238000000034 method Methods 0.000 title claims description 23
238000002360 preparation method Methods 0.000 title claims description 7
FYTNKOSUJSUKML-UHFFFAOYSA-N 2-hydroxy-5-nitrosocyclohepta-2,4,6-trien-1-one Chemical compound OC1=CC=C(N=O)C=CC1=O FYTNKOSUJSUKML-UHFFFAOYSA-N 0.000 claims description 11
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 5
XPAWKCACXZIYSZ-UHFFFAOYSA-N N-amino-N-hydroxypyridine-4-carboxamide Chemical compound NN(O)C(=O)c1ccncc1 XPAWKCACXZIYSZ-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004442 acylamino group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
238000002211 ultraviolet spectrum Methods 0.000 description 16
239000000047 product Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 12
239000013078 crystal Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
239000013081 microcrystal Substances 0.000 description 8
XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 7
-1 p-dimethylaminophenyl Chemical group 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 4
XSONSBDQIFBIOY-UHFFFAOYSA-N 2-phenoxyacetohydrazide Chemical compound NNC(=O)COC1=CC=CC=C1 XSONSBDQIFBIOY-UHFFFAOYSA-N 0.000 description 3
REKQLYUAUXYJSZ-UHFFFAOYSA-N 4-methoxybenzohydrazide Chemical compound COC1=CC=C(C(=O)NN)C=C1 REKQLYUAUXYJSZ-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
DZLFRQHFFVRYEE-UHFFFAOYSA-N 1h-indole-2-carbohydrazide Chemical compound C1=CC=C2NC(C(=O)NN)=CC2=C1 DZLFRQHFFVRYEE-UHFFFAOYSA-N 0.000 description 2
JFONGQRKKZPXLX-UHFFFAOYSA-N 2-(4-nitrophenyl)acetohydrazide Chemical compound NNC(=O)CC1=CC=C([N+]([O-])=O)C=C1 JFONGQRKKZPXLX-UHFFFAOYSA-N 0.000 description 2
QCICYPQPGJJZGW-UHFFFAOYSA-N 2-hydroxypropanehydrazide Chemical compound CC(O)C(=O)NN QCICYPQPGJJZGW-UHFFFAOYSA-N 0.000 description 2
OQNKZWDYYSHLPO-UHFFFAOYSA-N 3-methylbutanehydrazide Chemical compound CC(C)CC(=O)NN OQNKZWDYYSHLPO-UHFFFAOYSA-N 0.000 description 2
HRYYAHKXNSUDFH-UHFFFAOYSA-N 5-nitrofuran-2-carbohydrazide Chemical compound NNC(=O)C1=CC=C([N+]([O-])=O)O1 HRYYAHKXNSUDFH-UHFFFAOYSA-N 0.000 description 2
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
FCCCRBDJBTVFSJ-UHFFFAOYSA-N butanehydrazide Chemical compound CCCC(=O)NN FCCCRBDJBTVFSJ-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
HMYRUXBSDBAVNN-UHFFFAOYSA-N nonanehydrazide Chemical compound CCCCCCCCC(=O)NN HMYRUXBSDBAVNN-UHFFFAOYSA-N 0.000 description 2
VMUZVGRNTPFTKE-UHFFFAOYSA-N octanehydrazide Chemical compound CCCCCCCC(=O)NN VMUZVGRNTPFTKE-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
OHFIJHDYYOCZME-UHFFFAOYSA-N pyrazine-2-carbohydrazide Chemical compound NNC(=O)C1=CN=CC=N1 OHFIJHDYYOCZME-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
BAQLNPIEFOYKNB-UHFFFAOYSA-N pyridine-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CC=N1 BAQLNPIEFOYKNB-UHFFFAOYSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
HITIGLAGJBMISF-UHFFFAOYSA-N 4-(dimethylamino)benzohydrazide Chemical compound CN(C)C1=CC=C(C(=O)NN)C=C1 HITIGLAGJBMISF-UHFFFAOYSA-N 0.000 description 1
MFFVZXOPRXMVET-UHFFFAOYSA-N 4-methylbenzohydrazide Chemical compound CC1=CC=C(C(=O)NN)C=C1 MFFVZXOPRXMVET-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
239000005711 Benzoic acid Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
201000009030 Carcinoma Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000192041 Micrococcus Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
230000001399 anti-metabolic effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
239000011356 non-aqueous organic solvent Substances 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH1453661A 1960-12-17 1961-12-15 Verfahren zur Herstellung von 2-Acylhydrazino-5-nitrosotroponen CH404688A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4969560		1960-12-17

Publications (1)

Publication Number	Publication Date
CH404688A true CH404688A (de)	1965-12-31

Family

ID=12838302

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1453661A CH404688A (de)	1960-12-17	1961-12-15	Verfahren zur Herstellung von 2-Acylhydrazino-5-nitrosotroponen

Country Status (5)

Country	Link
BE (1)	BE611566A (da)
CH (1)	CH404688A (da)
DK (1)	DK104729C (da)
FR (1)	FR1502603A (da)
GB (1)	GB953143A (da)

1961
- 1961-12-11 GB GB4418061A patent/GB953143A/en not_active Expired
- 1961-12-15 CH CH1453661A patent/CH404688A/de unknown
- 1961-12-15 BE BE611566A patent/BE611566A/fr unknown
- 1961-12-16 DK DK505761A patent/DK104729C/da active
1966
- 1966-12-16 FR FR882219A patent/FR1502603A/fr not_active Expired

Also Published As

Publication number	Publication date
BE611566A (fr)	1962-03-30
FR1502603A (fr)	1967-11-24
GB953143A (en)	1964-03-25
DK104729C (da)	1966-06-27

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