CH579073A5 - 3-(cycloalkane amidopyridyl(or hydro-pyridyl)-alkyl-) - indoles - as anti inflammatory,hypotensive and antihistaminic agents - Google Patents
3-(cycloalkane amidopyridyl(or hydro-pyridyl)-alkyl-) - indoles - as anti inflammatory,hypotensive and antihistaminic agentsInfo
- Publication number
- CH579073A5 CH579073A5 CH1585771A CH1585771A CH579073A5 CH 579073 A5 CH579073 A5 CH 579073A5 CH 1585771 A CH1585771 A CH 1585771A CH 1585771 A CH1585771 A CH 1585771A CH 579073 A5 CH579073 A5 CH 579073A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- hydrogen
- group
- alkyl
- compound
- Prior art date
Links
- 239000000739 antihistaminic agent Substances 0.000 title description 11
- 230000003110 anti-inflammatory effect Effects 0.000 title description 2
- 208000001953 Hypotension Diseases 0.000 title 1
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 229940125715 antihistaminic agent Drugs 0.000 title 1
- 239000002220 antihypertensive agent Substances 0.000 title 1
- 208000021822 hypotensive Diseases 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims 1
- NTLAICDKHHQUGC-UHFFFAOYSA-N 3-(2-bromoethyl)-1h-indole Chemical compound C1=CC=C2C(CCBr)=CNC2=C1 NTLAICDKHHQUGC-UHFFFAOYSA-N 0.000 abstract description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract description 2
- AUJTUJNVNBZXGF-UHFFFAOYSA-N n-piperidin-4-ylcyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NC1CCNCC1 AUJTUJNVNBZXGF-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 15
- -1 methoxy, ethoxy, hydroxy, methyl Chemical group 0.000 description 14
- 229960001340 histamine Drugs 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 9
- 230000001387 anti-histamine Effects 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MLEGMEBCXGDFQT-UHFFFAOYSA-N 1-benzylpiperidin-2-one Chemical compound O=C1CCCCN1CC1=CC=CC=C1 MLEGMEBCXGDFQT-UHFFFAOYSA-N 0.000 description 1
- XLZYMUNRALGNSP-UHFFFAOYSA-N 2-oxo-2-(5-phenylmethoxy-1h-indol-3-yl)acetyl chloride Chemical compound C1=C2C(C(=O)C(=O)Cl)=CNC2=CC=C1OCC1=CC=CC=C1 XLZYMUNRALGNSP-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- GKDOBWORFYLTIL-UHFFFAOYSA-N 3-(2-bromoethyl)-2-methyl-1h-indole Chemical compound C1=CC=C2C(CCBr)=C(C)NC2=C1 GKDOBWORFYLTIL-UHFFFAOYSA-N 0.000 description 1
- MGJBBCJUPAVIGU-UHFFFAOYSA-N 3-(2-bromoethyl)-5-methoxy-2-methyl-1H-indole Chemical compound BrCCC1=C(NC2=CC=C(C=C12)OC)C MGJBBCJUPAVIGU-UHFFFAOYSA-N 0.000 description 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PCDIVXQWFZRWJT-UHFFFAOYSA-N CC(CN(CCC1=C(C)NC2=CC=CC=C12)CC1)C1NC(C1CCCCC1)=O Chemical compound CC(CN(CCC1=C(C)NC2=CC=CC=C12)CC1)C1NC(C1CCCCC1)=O PCDIVXQWFZRWJT-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VAQRORJIKDCOBZ-UHFFFAOYSA-N N-[1-[2-(2-methyl-1H-indol-3-yl)ethyl]piperidin-4-yl]cyclohexanecarboxamide Chemical compound C1(CCCCC1)C(=O)NC1CCN(CC1)CCC1=C(NC2=CC=CC=C12)C VAQRORJIKDCOBZ-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 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 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- BYABRKKQSVQWPG-UHFFFAOYSA-N n-[1-[2-(1h-indol-3-yl)ethyl]piperidin-4-yl]cyclohexanecarboxamide Chemical compound C1CN(CCC=2C3=CC=CC=C3NC=2)CCC1NC(=O)C1CCCCC1 BYABRKKQSVQWPG-UHFFFAOYSA-N 0.000 description 1
- SMLSJWDRRZCQLU-UHFFFAOYSA-N n-piperidin-4-ylcyclohexanecarboxamide;hydrochloride Chemical compound Cl.C1CCCCC1C(=O)NC1CCNCC1 SMLSJWDRRZCQLU-UHFFFAOYSA-N 0.000 description 1
- PNWVOLKZHJEWQU-UHFFFAOYSA-N n-pyridin-4-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=NC=C1 PNWVOLKZHJEWQU-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1585771A CH579073A5 (en) | 1971-10-29 | 1971-10-29 | 3-(cycloalkane amidopyridyl(or hydro-pyridyl)-alkyl-) - indoles - as anti inflammatory,hypotensive and antihistaminic agents |
| CH508976A CH602706A5 (OSRAM) | 1971-10-29 | 1976-04-22 | |
| CH508876A CH602705A5 (OSRAM) | 1971-10-29 | 1976-04-22 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1585771A CH579073A5 (en) | 1971-10-29 | 1971-10-29 | 3-(cycloalkane amidopyridyl(or hydro-pyridyl)-alkyl-) - indoles - as anti inflammatory,hypotensive and antihistaminic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH579073A5 true CH579073A5 (en) | 1976-08-31 |
Family
ID=4412549
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1585771A CH579073A5 (en) | 1971-10-29 | 1971-10-29 | 3-(cycloalkane amidopyridyl(or hydro-pyridyl)-alkyl-) - indoles - as anti inflammatory,hypotensive and antihistaminic agents |
| CH508976A CH602706A5 (OSRAM) | 1971-10-29 | 1976-04-22 | |
| CH508876A CH602705A5 (OSRAM) | 1971-10-29 | 1976-04-22 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH508976A CH602706A5 (OSRAM) | 1971-10-29 | 1976-04-22 | |
| CH508876A CH602705A5 (OSRAM) | 1971-10-29 | 1976-04-22 |
Country Status (1)
| Country | Link |
|---|---|
| CH (3) | CH579073A5 (OSRAM) |
-
1971
- 1971-10-29 CH CH1585771A patent/CH579073A5/de not_active IP Right Cessation
-
1976
- 1976-04-22 CH CH508976A patent/CH602706A5/xx not_active IP Right Cessation
- 1976-04-22 CH CH508876A patent/CH602705A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH602706A5 (OSRAM) | 1978-07-31 |
| CH602705A5 (OSRAM) | 1978-07-31 |
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