JPH0427236B2 - - Google Patents

Info

Publication number: JPH0427236B2
Authority: JP; Japan
Prior art keywords: indazole; substituted; present; formula; compound
Prior art date: 1982-03-17
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 - Lifetime

Application number

JP57040682A

Other languages

English (en)

Japanese (ja)

Other versions

JPS58159467A (ja

Inventor

Tadayuki Ibuki

Tasuke Sugihara

Hiroshi Kawakubo

Takanori Sone

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Asahi Chemical Industry Co Ltd

Original Assignee

Asahi Chemical Industry Co Ltd

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.)

1982-03-17

Filing date

1982-03-17

Publication date

1992-05-11

1982-03-17 Application filed by Asahi Chemical Industry Co Ltd filed Critical Asahi Chemical Industry Co Ltd

1982-03-17 Priority to JP4068282A priority Critical patent/JPS58159467A/ja

1983-09-21 Publication of JPS58159467A publication Critical patent/JPS58159467A/ja

1992-05-11 Publication of JPH0427236B2 publication Critical patent/JPH0427236B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 30
239000002253 acid Substances 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
-1 3-substituted indazole Chemical class 0.000 description 29
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 14
YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
238000000034 method Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
230000002378 acidificating effect Effects 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000003814 drug Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
208000007107 Stomach Ulcer Diseases 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
239000002260 anti-inflammatory agent Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
OXLDOVOICYKYSW-UHFFFAOYSA-N 1-[3-(1h-indazol-3-ylamino)propyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CCCNC1=NNC2=CC=CC=C12 OXLDOVOICYKYSW-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229940121363 anti-inflammatory agent Drugs 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
QVOSSCIRWMZKRA-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-1h-indazol-3-amine Chemical compound N=1NC2=CC=CC=C2C=1NCCN1CCOCC1 QVOSSCIRWMZKRA-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
230000003637 steroidlike Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
230000001562 ulcerogenic effect Effects 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
229940124599 anti-inflammatory drug Drugs 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000012433 hydrogen halide Substances 0.000 description 3
229910000039 hydrogen halide Inorganic materials 0.000 description 3
230000004054 inflammatory process Effects 0.000 description 3
239000002798 polar solvent Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
HNNIWKQLJSNAEQ-UHFFFAOYSA-N Benzydamine hydrochloride Chemical compound Cl.C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 HNNIWKQLJSNAEQ-UHFFFAOYSA-N 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
239000003125 aqueous solvent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229960000905 indomethacin Drugs 0.000 description 2
230000004968 inflammatory condition Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
NIYFKJYEUPPINB-UHFFFAOYSA-N n-(3-morpholin-4-ylpropyl)-1h-indazol-3-amine Chemical compound N=1NC2=CC=CC=C2C=1NCCCN1CCOCC1 NIYFKJYEUPPINB-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical compound CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-M 4-aminosalicylate(1-) Chemical compound NC1=CC=C(C([O-])=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
229960001689 benzydamine hydrochloride Drugs 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
208000010643 digestive system disease Diseases 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
208000018685 gastrointestinal system disease Diseases 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
150000008282 halocarbons Chemical class 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
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
229940089151 indomethacin 20 mg Drugs 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000010446 mirabilite Substances 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
WGOFCCGLYQIQSC-UHFFFAOYSA-N n-[3-(2,6-dimethylpiperidin-1-yl)propyl]-1h-indazol-3-amine Chemical compound CC1CCCC(C)N1CCCNC1=NNC2=CC=CC=C12 WGOFCCGLYQIQSC-UHFFFAOYSA-N 0.000 description 1
AJIMRBGUCLACKE-UHFFFAOYSA-N n-[3-(4-chloropiperidin-1-yl)propyl]-1h-indazol-3-amine Chemical compound C1CC(Cl)CCN1CCCNC1=NNC2=CC=CC=C12 AJIMRBGUCLACKE-UHFFFAOYSA-N 0.000 description 1
XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
ONJSZLXSECQROL-UHFFFAOYSA-N salicyluric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1O ONJSZLXSECQROL-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical class [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Landscapes

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

JP4068282A 1982-03-17 1982-03-17 新規な３位置換インダゾ−ル誘導体およびその製造法 Granted JPS58159467A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP4068282A JPS58159467A (ja)	1982-03-17	1982-03-17	新規な３位置換インダゾ−ル誘導体およびその製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4068282A JPS58159467A (ja)	1982-03-17	1982-03-17	新規な３位置換インダゾ−ル誘導体およびその製造法

Publications (2)

Publication Number	Publication Date
JPS58159467A JPS58159467A (ja)	1983-09-21
JPH0427236B2 true JPH0427236B2 (fr)	1992-05-11

Family

ID=12587301

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4068282A Granted JPS58159467A (ja)	1982-03-17	1982-03-17	新規な３位置換インダゾ−ル誘導体およびその製造法

Country Status (1)

Country	Link
JP (1)	JPS58159467A (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5754175A (ja) *	1980-09-19	1982-03-31	Asahi Chem Ind Co Ltd	Shinkina33aminoindazoorujudotai

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS649989A (en) *	1987-06-30	1989-01-13	Taiho Pharmaceutical Co Ltd	Isoxazole compound

1982
- 1982-03-17 JP JP4068282A patent/JPS58159467A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5754175A (ja) *	1980-09-19	1982-03-31	Asahi Chem Ind Co Ltd	Shinkina33aminoindazoorujudotai

Also Published As

Publication number	Publication date
JPS58159467A (ja)	1983-09-21

Publication	Publication Date	Title
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JPH021141B2 (fr)	1990-01-10
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