DE1246746B - Verfahren zur Herstellung von in der 1-Stellung substituierten 3-Dialkylaminoalkoxy-indazolen - Google Patents
Verfahren zur Herstellung von in der 1-Stellung substituierten 3-Dialkylaminoalkoxy-indazolenInfo
- Publication number
- DE1246746B DE1246746B DEA45118A DEA0045118A DE1246746B DE 1246746 B DE1246746 B DE 1246746B DE A45118 A DEA45118 A DE A45118A DE A0045118 A DEA0045118 A DE A0045118A DE 1246746 B DE1246746 B DE 1246746B
- Authority
- DE
- Germany
- Prior art keywords
- indazole
- hydrochloride
- chloro
- benzyl
- lower alkyl
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 alkyl radical Chemical class 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- SWEICGMKXPNXNU-UHFFFAOYSA-N 1,2-dihydroindazol-3-one Chemical compound C1=CC=C2C(O)=NNC2=C1 SWEICGMKXPNXNU-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XFZJGFIKQCCLGK-UHFFFAOYSA-M 1,1-dimethyl-4-phenylpiperazinium iodide Chemical compound [I-].C1C[N+](C)(C)CCN1C1=CC=CC=C1 XFZJGFIKQCCLGK-UHFFFAOYSA-M 0.000 description 2
- CJBXLBPSBLXDJO-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-2h-indazol-3-one Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC=C2C(=O)N1 CJBXLBPSBLXDJO-UHFFFAOYSA-N 0.000 description 2
- ONNIFDMRZCMQQM-UHFFFAOYSA-N 1-methyl-2h-indazol-3-one Chemical compound C1=CC=C2N(C)NC(=O)C2=C1 ONNIFDMRZCMQQM-UHFFFAOYSA-N 0.000 description 2
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- WVMBPWMAQDVZCM-UHFFFAOYSA-N N-methylanthranilic acid Chemical compound CNC1=CC=CC=C1C(O)=O WVMBPWMAQDVZCM-UHFFFAOYSA-N 0.000 description 2
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 241001279009 Strychnos toxifera Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241000906446 Theraps Species 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 229940045511 barium chloride Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 150000002473 indoazoles Chemical class 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- YPSSCICDVDOEAI-UHFFFAOYSA-N methyl 2-amino-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1N YPSSCICDVDOEAI-UHFFFAOYSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 150000002832 nitroso derivatives Chemical class 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229960005453 strychnine Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- BTDZXNLCJNUASB-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2H-indazol-3-one Chemical compound COC1=CC=C(C=C1)N1NC(C2=CC=CC=C12)=O BTDZXNLCJNUASB-UHFFFAOYSA-N 0.000 description 1
- SOLDYCGMHQNPBO-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-2h-indazol-3-one Chemical compound ClC1=CC=CC=C1CN1C2=CC=CC=C2C(=O)N1 SOLDYCGMHQNPBO-UHFFFAOYSA-N 0.000 description 1
- ZRZSYDHZWHSHMQ-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-2h-indazol-3-one Chemical compound ClC1=CC=CC(CN2C3=CC=CC=C3C(=O)N2)=C1 ZRZSYDHZWHSHMQ-UHFFFAOYSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- BMKYHARYHCUVDW-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-2h-indazol-3-one Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=CC=C2C(=O)N1 BMKYHARYHCUVDW-UHFFFAOYSA-N 0.000 description 1
- VDACPJZGZTZWNX-UHFFFAOYSA-N 1-benzyl-5-chloro-2h-indazol-3-one Chemical compound C12=CC=C(Cl)C=C2C(O)=NN1CC1=CC=CC=C1 VDACPJZGZTZWNX-UHFFFAOYSA-N 0.000 description 1
- GDKTYERFWWLIAA-UHFFFAOYSA-N 1-butyl-5-chloro-2h-indazol-3-one Chemical compound ClC1=CC=C2N(CCCC)NC(=O)C2=C1 GDKTYERFWWLIAA-UHFFFAOYSA-N 0.000 description 1
- JUISOKJPZJVRGU-UHFFFAOYSA-N 1-butyl-6-chloro-2h-indazol-3-one Chemical compound C1=C(Cl)C=C2N(CCCC)NC(=O)C2=C1 JUISOKJPZJVRGU-UHFFFAOYSA-N 0.000 description 1
- JHRXFPUUMCFNLQ-UHFFFAOYSA-N 2-(benzylamino)-4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NCC1=CC=CC=C1 JHRXFPUUMCFNLQ-UHFFFAOYSA-N 0.000 description 1
- VXZOBNZOEBYBFR-UHFFFAOYSA-N 2-[benzyl(nitroso)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1N(N=O)CC1=CC=CC=C1 VXZOBNZOEBYBFR-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- SSNZGVLSPNDFPH-UHFFFAOYSA-N 5-chloro-1-[(4-methoxyphenyl)methyl]-2h-indazol-3-one Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=C(Cl)C=C2C(=O)N1 SSNZGVLSPNDFPH-UHFFFAOYSA-N 0.000 description 1
- DPCGVKRVIVMNTA-UHFFFAOYSA-N 6-chloro-1-[(4-chlorophenyl)methyl]-2h-indazol-3-one Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC(Cl)=CC=C2C(=O)N1 DPCGVKRVIVMNTA-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- KTANDGWGJSLJPB-UHFFFAOYSA-N methyl 2-(benzylamino)-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1NCC1=CC=CC=C1 KTANDGWGJSLJPB-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Devices That Are Associated With Refrigeration Equipment (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3804563 | 1963-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1246746B true DE1246746B (de) | 1967-08-10 |
Family
ID=11245984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA45118A Pending DE1246746B (de) | 1963-08-09 | 1964-01-30 | Verfahren zur Herstellung von in der 1-Stellung substituierten 3-Dialkylaminoalkoxy-indazolen |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT247320B (enExample) |
| DE (1) | DE1246746B (enExample) |
| ES (1) | ES302872A1 (enExample) |
| LU (1) | LU46555A1 (enExample) |
| NL (2) | NL6407088A (enExample) |
| NO (1) | NO115779B (enExample) |
| SE (1) | SE301149B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725431A (en) * | 1970-09-23 | 1973-04-03 | Ciba Geigy Corp | 1-aralkyl-3-aminoindazoles |
-
0
- NL NL130990D patent/NL130990C/xx active
-
1964
- 1964-01-30 DE DEA45118A patent/DE1246746B/de active Pending
- 1964-06-12 SE SE718164A patent/SE301149B/xx unknown
- 1964-06-22 NL NL6407088A patent/NL6407088A/xx unknown
- 1964-07-17 LU LU46555D patent/LU46555A1/xx unknown
- 1964-08-06 AT AT676764A patent/AT247320B/de active
- 1964-08-06 ES ES0302872A patent/ES302872A1/es not_active Expired
- 1964-08-06 NO NO15429464A patent/NO115779B/no unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725431A (en) * | 1970-09-23 | 1973-04-03 | Ciba Geigy Corp | 1-aralkyl-3-aminoindazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| NO115779B (enExample) | 1968-12-02 |
| NL130990C (enExample) | |
| ES302872A1 (es) | 1965-03-01 |
| AT247320B (de) | 1966-06-10 |
| LU46555A1 (enExample) | 1964-09-17 |
| NL6407088A (enExample) | 1965-02-10 |
| SE301149B (enExample) | 1968-05-27 |
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