CS241020B2 - Method of aminosubstituted 4,5,6,7-tetrahydro-1h(or 2h)-indazoles' derivatives preparation - Google Patents

Method of aminosubstituted 4,5,6,7-tetrahydro-1h(or 2h)-indazoles' derivatives preparation Download PDF

Info

Publication number: CS241020B2
Authority: CS; Czechoslovakia
Prior art keywords: tetrahydro; indazole; amino; propyl; compounds
Prior art date: 1979-01-22

Application number

CS794476A

Other languages

Czech (cs)

English (en)

Other versions

CS447679A2 (en

Inventor

Nicholas J Bach

Edmund C Kornfeld

Original Assignee

Lilly Co Eli

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.)

1979-01-22

Filing date

1979-06-28

Publication date

1986-03-13

1979-06-28 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1985-06-13 Publication of CS447679A2 publication Critical patent/CS447679A2/cs

1986-03-13 Publication of CS241020B2 publication Critical patent/CS241020B2/cs

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 6
125000003277 amino group Chemical group 0.000 title claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 31
150000003839 salts Chemical class 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
150000001299 aldehydes Chemical class 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
238000007912 intraperitoneal administration Methods 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
XTWQGFNPJUNTFD-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-indazol-5-amine Chemical compound C1C(N)CCC2=C1C=NN2 XTWQGFNPJUNTFD-UHFFFAOYSA-N 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
241000699670 Mus sp. Species 0.000 claims 1
230000037396 body weight Effects 0.000 claims 1
239000007903 gelatin capsule Substances 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
229910052987 metal hydride Inorganic materials 0.000 claims 1
150000004681 metal hydrides Chemical class 0.000 claims 1
231100001160 nonlethal Toxicity 0.000 claims 1
108010057464 Prolactin Proteins 0.000 abstract description 12
102000003946 Prolactin Human genes 0.000 abstract description 12
229940097325 prolactin Drugs 0.000 abstract description 12
230000005764 inhibitory process Effects 0.000 abstract description 6
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 abstract description 5
206010034010 Parkinsonism Diseases 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 abstract description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
208000027089 Parkinsonian disease Diseases 0.000 abstract 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
WZEMYWNHKFIVKE-UHFFFAOYSA-N n-(4-oxocyclohexyl)acetamide Chemical compound CC(=O)NC1CCC(=O)CC1 WZEMYWNHKFIVKE-UHFFFAOYSA-N 0.000 abstract 1
241000700159 Rattus Species 0.000 description 8
239000000203 mixture Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
239000003136 dopamine receptor stimulating agent Substances 0.000 description 5
-1 hydrochloric acid Chemical class 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
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
101000687509 Rattus norvegicus Prolactin Proteins 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000005534 decanoate group Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000005187 foaming Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000005286 illumination Methods 0.000 description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
230000006651 lactation Effects 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
150000002690 malonic acid derivatives Chemical class 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
229960003147 reserpine Drugs 0.000 description 2
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
230000028327 secretion Effects 0.000 description 2
239000002904 solvent Substances 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
HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-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
WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical class CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
ZRCJPZHBTJQPDS-UHFFFAOYSA-N 3-propyl-4,5,6,7-tetrahydroindazol-2-amine Chemical compound C(CC)C=1N(N=C2CCCCC=12)N ZRCJPZHBTJQPDS-UHFFFAOYSA-N 0.000 description 1
IHDUZMHOIVQJGL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-indazol-5-amine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCC2=C1C=NN2 IHDUZMHOIVQJGL-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
CTBBFWMOALTJED-UHFFFAOYSA-N Cl.C(CC)C1=NN(C=2CCCCC12)N Chemical compound Cl.C(CC)C1=NN(C=2CCCCC12)N CTBBFWMOALTJED-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical class COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
IGVPBCZDHMIOJH-UHFFFAOYSA-N Phenyl butyrate Chemical class CCCC(=O)OC1=CC=CC=C1 IGVPBCZDHMIOJH-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940052760 dopamine agonists Drugs 0.000 description 1
239000000284 extract Substances 0.000 description 1
150000004673 fluoride salts Chemical class 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000011521 glass Substances 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical class CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
150000004728 pyruvic acid derivatives Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
238000005303 weighing Methods 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CS794476A 1979-01-22 1979-06-28 Method of aminosubstituted 4,5,6,7-tetrahydro-1h(or 2h)-indazoles' derivatives preparation CS241020B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US506479A	1979-01-22	1979-01-22

Publications (2)

Publication Number	Publication Date
CS447679A2 CS447679A2 (en)	1985-06-13
CS241020B2 true CS241020B2 (en)	1986-03-13

Family

ID=21713977

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794476A CS241020B2 (en)	1979-01-22	1979-06-28	Method of aminosubstituted 4,5,6,7-tetrahydro-1h(or 2h)-indazoles' derivatives preparation

Country Status (6)

Country	Link
JP (1)	JPS55100367A (ja)
KR (2)	KR830000754B1 (ja)
CS (1)	CS241020B2 (ja)
HU (1)	HU184624B (ja)
PL (2)	PL118568B1 (ja)
SU (3)	SU1311620A3 (ja)

1979
- 1979-06-26 HU HU79EI862A patent/HU184624B/hu not_active IP Right Cessation
- 1979-06-28 CS CS794476A patent/CS241020B2/cs unknown
- 1979-06-28 SU SU792786155A patent/SU1311620A3/ru active
- 1979-06-28 JP JP8340779A patent/JPS55100367A/ja active Pending
- 1979-06-29 PL PL1979226403A patent/PL118568B1/pl unknown
- 1979-06-29 KR KR1019790002150A patent/KR830000754B1/ko not_active Expired
- 1979-06-29 KR KR1019790002148A patent/KR830000708B1/ko not_active Expired
- 1979-06-29 PL PL1979226402A patent/PL118459B1/pl unknown
1981
- 1981-01-20 SU SU813230702A patent/SU976848A3/ru active
- 1981-01-21 SU SU813233699A patent/SU1015823A3/ru active

Also Published As

Publication number	Publication date
SU976848A3 (ru)	1982-11-23
CS447679A2 (en)	1985-06-13
HU184624B (en)	1984-09-28
PL118568B1 (en)	1981-10-31
KR830000754B1 (ko)	1983-04-09
KR830000708B1 (ko)	1983-04-06
JPS55100367A (en)	1980-07-31
SU1311620A3 (ru)	1987-05-15
SU1015823A3 (ru)	1983-04-30
PL118459B1 (en)	1981-10-31

Publication	Publication Date	Title
HU190028B (en)	1986-08-28	Process for preparing pyridazine derivatives
HU189608B (en)	1986-07-28	Process for producing pyridazine derivatives
CH662563A5 (fr)	1987-10-15	Derives de coumarine, leurs procedes de preparation et compositions pharmaceutiques les contenant.
HUE028159T2 (en)	2016-12-28	Acid addition salts of risperidone and pharmaceutical compositions containing them
CS241020B2 (en)	1986-03-13	Method of aminosubstituted 4,5,6,7-tetrahydro-1h(or 2h)-indazoles' derivatives preparation
CS199610B2 (en)	1980-07-31	Process for preparing 8-8-disubstituted 6-methylergolines and derivatives thereof
CN101970438A (zh)	2011-02-09	新的1，4-二氮杂-二环[3.2.2]壬基嘧啶衍生物及它们的医药应用
HU205920B (en)	1992-07-28	Process for producing 2-phenoxy-methyl/-3-/alkanoyl-, carboxy-, carbalkoxy- or carboxamido- -acetyl/-1,3-thiazolidine derivatives and pharmaceutical compositions containing them
JPH01275585A (ja)	1989-11-06	４，５，６，７―テトラハイドロイソチアゾロ〔４，５―ｃ〕ピリジン誘導体及び異性体
US4016280A (en)	1977-04-05	4,4-Diarylpiperidine compositions and use
FI75153B (fi)	1988-01-29	Foerfarande foer framstaellning av nya farmakologiskt aktiva (4r,5as)-4,5,5a,6-tetrahydro-dibens/cd,f/indolderivat.
PT85656B (pt)	1990-05-31	Processos para a preparacao de 2,3,4,5,6,7-hexaidro-2,7-metano-1,5- benzoxazoninas e- 1,4- benzoxazoninas e de preparacoes farmaceuticas que as contem
US4607040A (en)	1986-08-19	Quinoline derivatives which are 5-hydroxytryptamine antagonists
IE62011B1 (en)	1994-12-14	Piperazine derivatives
KR930006777B1 (ko)	1993-07-23	피리도[1,2-a]인돌 화합물 및 그 제조방법
CS237331B2 (en)	1985-07-16	Processing of octahydropyrazole/3,4-g/chinoline
DK149199B (da)	1986-03-10	Analogifremgangsmaade til fremstilling af hexahydro-1,4-oxazepiner eller salte deraf dannet med fysiologisk acceptable syrer
US3487469A (en)	1969-12-30	1,2-diaryl-3-(aminomethyl)-3-buten-2-ols and their acyl derivatives
CZ289526B6 (cs)	2002-02-13	(S) nebo (R) Enantiomer piperazinylové sloučeniny a způsob jeho přípravy
CS235078B2 (en)	1985-04-16	Method of tetrahydro-2h-benzo-(lc)ppyrrole preparation
US4133888A (en)	1979-01-09	Analgesic and morphine antagonistic 2'-hydroxy-2-(5-isoxazolyl-methyl)-6,7-benzomorphans and salts thereof
JPH07501817A (ja)	1995-02-23	新規置換オキサジノイソキノリン誘導体，該誘導体を含有する医薬組成物および該誘導体の製法
DK149848B (da)	1986-10-13	Analogifremgangsmaade til fremstilling af tautomere aminosubstituerede 4,5,6,7-tetrahydro-1h-(eller 2h)-indazoler eller salte deraf
NL8204197A (nl)	1983-06-01	4-(2,1,3-benzoxadiazool-4-yl) -1,4-dihydropyridazinederivaten, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten.
JPH11504616A (ja)	1999-04-27	ジベンズ［ｃｄ，ｆ］インドール誘導体