CA1040640A - Indazole-3-carboxylic acid hydrazides and a process for the preparation thereof - Google Patents
Indazole-3-carboxylic acid hydrazides and a process for the preparation thereofInfo
- Publication number
- CA1040640A CA1040640A CA207,093A CA207093A CA1040640A CA 1040640 A CA1040640 A CA 1040640A CA 207093 A CA207093 A CA 207093A CA 1040640 A CA1040640 A CA 1040640A
- Authority
- CA
- Canada
- Prior art keywords
- carboxylic acid
- compound
- group
- dimethoxyindazole
- general formula
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 45
- 230000008569 process Effects 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 4
- JOUPSJAGJHYWLM-UHFFFAOYSA-N 1h-indazole-3-carbohydrazide Chemical class C1=CC=C2C(C(=O)NN)=NNC2=C1 JOUPSJAGJHYWLM-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 15
- -1 hydroxy, benzyloxy, nitro, amino Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000005936 piperidyl group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 3
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002541 furyl group Chemical class 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 6
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 25
- STUCOFMCGRLQJY-UHFFFAOYSA-N 5,6-dimethoxy-1h-indazole-3-carbohydrazide Chemical compound C1=C(OC)C(OC)=CC2=C1C(C(=O)NN)=NN2 STUCOFMCGRLQJY-UHFFFAOYSA-N 0.000 claims description 14
- 230000009467 reduction Effects 0.000 claims description 12
- IWUGDDTXRWFNJY-UHFFFAOYSA-N 5,6-dimethoxy-1h-indazole-3-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC2=C1C(C(O)=O)=NN2 IWUGDDTXRWFNJY-UHFFFAOYSA-N 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000012279 sodium borohydride Substances 0.000 claims description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- BFRNWIBUXCUWAZ-UHFFFAOYSA-N 5,6-dimethoxy-n-(propan-2-ylideneamino)-1h-indazole-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC2=C1C(C(=O)NN=C(C)C)=NN2 BFRNWIBUXCUWAZ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- KCUFGKJXOXLSJY-UHFFFAOYSA-N n-benzyl-5,6-dimethoxy-1h-indazole-3-carbohydrazide Chemical compound C1=2C=C(OC)C(OC)=CC=2NN=C1C(=O)N(N)CC1=CC=CC=C1 KCUFGKJXOXLSJY-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 claims 2
- VSEBFQURCLBIPK-UHFFFAOYSA-N N-cycloheptyl-5,6-dimethoxy-1H-indazole-3-carbohydrazide Chemical compound C1(CCCCCC1)N(N)C(=O)C1=NNC2=CC(=C(C=C12)OC)OC VSEBFQURCLBIPK-UHFFFAOYSA-N 0.000 claims 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 claims 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 9
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- 206010029216 Nervousness Diseases 0.000 abstract description 2
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- 150000002367 halogens Chemical group 0.000 abstract 1
- 238000009738 saturating Methods 0.000 abstract 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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- 241000699670 Mus sp. Species 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 5
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- 238000001816 cooling Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
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- 231100000397 ulcer Toxicity 0.000 description 4
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
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- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
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- BHXVYTQDWMQVBI-UHFFFAOYSA-N 1h-indazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC2=C1 BHXVYTQDWMQVBI-UHFFFAOYSA-N 0.000 description 1
- JGOAIQNSOGZNBX-UHFFFAOYSA-N 2,2-diphenylacetic acid 2-(diethylamino)ethyl ester Chemical compound C=1C=CC=CC=1C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 JGOAIQNSOGZNBX-UHFFFAOYSA-N 0.000 description 1
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- 239000006260 foam Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000002911 mydriatic effect Effects 0.000 description 1
- HLIYQKBWEPAFBC-UHFFFAOYSA-N n-(cyclohexylideneamino)-5,6-dimethoxy-1h-indazole-3-carboxamide Chemical compound C1=2C=C(OC)C(OC)=CC=2NN=C1C(=O)NN=C1CCCCC1 HLIYQKBWEPAFBC-UHFFFAOYSA-N 0.000 description 1
- PRTGMNWCZPAEHE-UHFFFAOYSA-N n-(ethylideneamino)-5,6-dimethoxy-1h-indazole-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC2=C1C(C(=O)NN=CC)=NN2 PRTGMNWCZPAEHE-UHFFFAOYSA-N 0.000 description 1
- FESVRRGCKBDHGA-UHFFFAOYSA-N n-cyclohexyl-5,6-dimethoxy-1h-indazole-3-carbohydrazide Chemical compound C1=2C=C(OC)C(OC)=CC=2NN=C1C(=O)N(N)C1CCCCC1 FESVRRGCKBDHGA-UHFFFAOYSA-N 0.000 description 1
- OTJTXGDLUPZENN-UHFFFAOYSA-N n-ethyl-5,6-dimethoxy-1h-indazole-3-carbohydrazide Chemical compound COC1=C(OC)C=C2C(C(=O)N(N)CC)=NNC2=C1 OTJTXGDLUPZENN-UHFFFAOYSA-N 0.000 description 1
- 230000001379 nervous effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- DGMKFQYCZXERLX-UHFFFAOYSA-N proglumide Chemical compound CCCN(CCC)C(=O)C(CCC(O)=O)NC(=O)C1=CC=CC=C1 DGMKFQYCZXERLX-UHFFFAOYSA-N 0.000 description 1
- 229960003857 proglumide Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 101150085636 resD gene Proteins 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUEY002169 | 1973-08-16 | ||
| HUEE002169 HU168027B (en:Method) | 1973-08-16 | 1973-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1040640A true CA1040640A (en) | 1978-10-17 |
Family
ID=26318449
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA207,093A Expired CA1040640A (en) | 1973-08-16 | 1974-08-15 | Indazole-3-carboxylic acid hydrazides and a process for the preparation thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3956312A (en:Method) |
| JP (1) | JPS5527909B2 (en:Method) |
| AT (1) | AT334895B (en:Method) |
| BE (1) | BE818848A (en:Method) |
| CA (1) | CA1040640A (en:Method) |
| CH (1) | CH612674A5 (en:Method) |
| DE (1) | DE2438397A1 (en:Method) |
| FR (1) | FR2240731B1 (en:Method) |
| GB (1) | GB1443609A (en:Method) |
| NL (1) | NL7410826A (en:Method) |
| SE (1) | SE419859B (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4824884A (en) * | 1987-08-12 | 1989-04-25 | Pennwalt Corporation | Cyclic anhydride derivatives of hydrazide functionalized hindered amine light stabilizers |
| US4861777A (en) * | 1987-09-11 | 1989-08-29 | Mitsubishi Kasei Corporation | Pyrazole derivative and insecticidal and miticidal composition containing the derivative as active ingredient |
| JP2861104B2 (ja) * | 1988-10-14 | 1999-02-24 | 三菱化学株式会社 | ピラゾールアミド類およびこれを有効成分とする殺虫、殺ダニ剤 |
| US6001865A (en) * | 1999-05-04 | 1999-12-14 | Angelini Pharmaceuticals Inc. | 3-substituted 1-benzyl-1H-indazole derivatives as antifertility agents |
| CN115715776B (zh) * | 2021-02-10 | 2024-10-22 | 北京大学第一医院 | 一种吲唑酰肼类化合物及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3007938A (en) * | 1959-04-17 | 1961-11-07 | Sterling Drug Inc | 1-(3-indazolecarbonyl)-hydrazines and their preparation |
| US3705175A (en) * | 1969-04-01 | 1972-12-05 | Egyt Gyogyszervegyeszeti Gyar | Indazole-3-carboxylic amides |
-
1974
- 1974-08-07 CH CH1080774A patent/CH612674A5/xx not_active IP Right Cessation
- 1974-08-09 SE SE7410244A patent/SE419859B/xx unknown
- 1974-08-09 DE DE2438397A patent/DE2438397A1/de not_active Withdrawn
- 1974-08-12 GB GB35382/74A patent/GB1443609A/en not_active Expired
- 1974-08-13 FR FR7428017A patent/FR2240731B1/fr not_active Expired
- 1974-08-13 NL NL7410826A patent/NL7410826A/xx not_active Application Discontinuation
- 1974-08-14 AT AT665374A patent/AT334895B/de not_active IP Right Cessation
- 1974-08-14 BE BE147603A patent/BE818848A/xx unknown
- 1974-08-15 CA CA207,093A patent/CA1040640A/en not_active Expired
- 1974-08-15 US US05/497,676 patent/US3956312A/en not_active Expired - Lifetime
- 1974-08-16 JP JP9412774A patent/JPS5527909B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5070365A (en:Method) | 1975-06-11 |
| FR2240731A1 (en:Method) | 1975-03-14 |
| AT334895B (de) | 1977-02-10 |
| DE2438397A1 (de) | 1975-02-27 |
| US3956312A (en) | 1976-05-11 |
| SE419859B (sv) | 1981-08-31 |
| JPS5527909B2 (en:Method) | 1980-07-24 |
| CH612674A5 (en:Method) | 1979-08-15 |
| GB1443609A (en) | 1976-07-21 |
| BE818848A (fr) | 1974-12-02 |
| SE7410244L (en:Method) | 1975-02-17 |
| NL7410826A (nl) | 1975-02-18 |
| ATA665374A (de) | 1976-06-15 |
| FR2240731B1 (en:Method) | 1978-07-28 |
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