IE52014B1 - Piperidine derivatives - Google Patents
Piperidine derivativesInfo
- Publication number
- IE52014B1 IE52014B1 IE392/81A IE39281A IE52014B1 IE 52014 B1 IE52014 B1 IE 52014B1 IE 392/81 A IE392/81 A IE 392/81A IE 39281 A IE39281 A IE 39281A IE 52014 B1 IE52014 B1 IE 52014B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compound
- piperid
- urea
- benzoyl
- Prior art date
Links
- 150000003053 piperidines Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 230000008569 process Effects 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- 239000004089 psychotropic agent Substances 0.000 claims abstract 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 51
- 239000004202 carbamide Substances 0.000 claims description 51
- -1 bsnzothiophsnyl Chemical group 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 239000002552 dosage form Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 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 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 230000000506 psychotropic effect Effects 0.000 claims description 3
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- WUKATCKYIFJWRX-UHFFFAOYSA-N n-[[1-[(4-ethylphenyl)methyl]piperidin-4-yl]carbamoyl]benzamide Chemical compound C1=CC(CC)=CC=C1CN1CCC(NC(=O)NC(=O)C=2C=CC=CC=2)CC1 WUKATCKYIFJWRX-UHFFFAOYSA-N 0.000 claims description 2
- AEVZCGHNJITRHX-UHFFFAOYSA-N n-[[1-[(4-propan-2-ylphenyl)methyl]piperidin-4-yl]carbamoyl]benzamide Chemical compound C1=CC(C(C)C)=CC=C1CN1CCC(NC(=O)NC(=O)C=2C=CC=CC=2)CC1 AEVZCGHNJITRHX-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005390 cinnolyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- BCSARMUYAOFBOR-UHFFFAOYSA-N n-[[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-yl]carbamoyl]benzamide Chemical compound C1CN(CC=2C=C3OCCOC3=CC=2)CCC1NC(=O)NC(=O)C1=CC=CC=C1 BCSARMUYAOFBOR-UHFFFAOYSA-N 0.000 claims 1
- KGXRMSOIUYKSMU-UHFFFAOYSA-N n-[[1-(2,3-dihydro-1h-inden-5-ylmethyl)piperidin-4-yl]carbamoyl]benzamide Chemical compound C1CN(CC=2C=C3CCCC3=CC=2)CCC1NC(=O)NC(=O)C1=CC=CC=C1 KGXRMSOIUYKSMU-UHFFFAOYSA-N 0.000 claims 1
- OZVRGIJZSGHRRK-UHFFFAOYSA-N n-[[1-(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)piperidin-4-yl]carbamoyl]benzamide Chemical compound C1CN(CC=2C=C3CCCCC3=CC=2)CCC1NC(=O)NC(=O)C1=CC=CC=C1 OZVRGIJZSGHRRK-UHFFFAOYSA-N 0.000 claims 1
- JVUPKNFVESNYAF-UHFFFAOYSA-N n-[[1-[(3,4-dimethylphenyl)methyl]piperidin-4-yl]carbamoyl]benzamide Chemical compound C1=C(C)C(C)=CC=C1CN1CCC(NC(=O)NC(=O)C=2C=CC=CC=2)CC1 JVUPKNFVESNYAF-UHFFFAOYSA-N 0.000 claims 1
- TVZPFULZXQANLQ-UHFFFAOYSA-N n-[[1-[(6-methoxynaphthalen-2-yl)methyl]piperidin-4-yl]carbamoyl]benzamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1CN(CC1)CCC1NC(=O)NC(=O)C1=CC=CC=C1 TVZPFULZXQANLQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 101150009274 nhr-1 gene Proteins 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000935 antidepressant agent Substances 0.000 abstract description 3
- 229940005513 antidepressants Drugs 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 125000002837 carbocyclic group Chemical group 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 description 41
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
- 150000003840 hydrochlorides Chemical class 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- VDPTZNWSWWZWNC-UHFFFAOYSA-N n-(piperidin-4-ylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=O)NC1CCNCC1 VDPTZNWSWWZWNC-UHFFFAOYSA-N 0.000 description 7
- 208000011580 syndromic disease Diseases 0.000 description 7
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- 230000005764 inhibitory process Effects 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 210000004556 brain Anatomy 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 208000013403 hyperactivity Diseases 0.000 description 4
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 4
- 229960004801 imipramine Drugs 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 230000013275 serotonin uptake Effects 0.000 description 4
- RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 3
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- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- DWKUKQRKVCMOLP-UHFFFAOYSA-N 1-piperideine Chemical class C1CCN=CC1 DWKUKQRKVCMOLP-UHFFFAOYSA-N 0.000 description 2
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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- 230000008517 inhibition of serotonin uptake Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- WWPITPSIWMXDPE-UHFFFAOYSA-N para-chloroamphetamine Chemical compound CC(N)CC1=CC=C(Cl)C=C1 WWPITPSIWMXDPE-UHFFFAOYSA-N 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- DXXBBUOVGDAFFJ-UHFFFAOYSA-N urea;hydrobromide Chemical compound [Br-].NC(O)=[NH2+] DXXBBUOVGDAFFJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8007048 | 1980-03-01 | ||
| GB8027435 | 1980-08-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE810392L IE810392L (en) | 1981-09-01 |
| IE52014B1 true IE52014B1 (en) | 1987-05-27 |
Family
ID=26274662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE392/81A IE52014B1 (en) | 1980-03-01 | 1981-02-25 | Piperidine derivatives |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4426387A (en, 2012) |
| EP (1) | EP0035374B1 (en, 2012) |
| KR (4) | KR850000630B1 (en, 2012) |
| AU (1) | AU542950B2 (en, 2012) |
| CA (1) | CA1173037A (en, 2012) |
| DE (1) | DE3168564D1 (en, 2012) |
| DK (1) | DK164546C (en, 2012) |
| EG (1) | EG16004A (en, 2012) |
| ES (4) | ES499716A0 (en, 2012) |
| FI (1) | FI77231C (en, 2012) |
| GR (1) | GR73576B (en, 2012) |
| HU (1) | HU187768B (en, 2012) |
| IE (1) | IE52014B1 (en, 2012) |
| IL (1) | IL62200A (en, 2012) |
| NO (1) | NO156864C (en, 2012) |
| NZ (1) | NZ196324A (en, 2012) |
| PH (1) | PH17019A (en, 2012) |
| PL (4) | PL128510B1 (en, 2012) |
| PT (1) | PT72562B (en, 2012) |
| YU (4) | YU47381A (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8528235D0 (en) * | 1985-11-15 | 1985-12-18 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US4508722A (en) * | 1981-05-18 | 1985-04-02 | Eli Lilly And Company | 1-Benzoyl-3-(arylpyridyl)urea compounds |
| ATE27152T1 (de) * | 1982-04-07 | 1987-05-15 | Ici Plc | Chinolin-derivate. |
| EP0093521B1 (en) * | 1982-05-04 | 1988-08-24 | Imperial Chemical Industries Plc | Quinoline derivatives |
| FR2527205A1 (fr) * | 1982-05-18 | 1983-11-25 | Bouchara Emile | Nouvelles phenyloxoalcoyl piperidines, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
| WO1985001288A1 (fr) * | 1983-09-19 | 1985-03-28 | Bouchara, Emile | Nouvelles piperidinoguanidines substituees, leur procede de preparation et les compositions pharmaceutiques en renfermant |
| US4569933A (en) * | 1984-04-13 | 1986-02-11 | Cornu Pierre Jean | Antihypertensive substituted derivatives of 2,5-diamino 1,4-diazole |
| GB8528234D0 (en) * | 1985-11-15 | 1985-12-18 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US4709094A (en) * | 1986-07-10 | 1987-11-24 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Sigma brain receptor ligands and their use |
| US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
| EP0343307A1 (en) * | 1988-05-26 | 1989-11-29 | Fabrica Espanola De Productos Quimicos Y Farmaceuticos, S.A. | 4-Piperidinealkanamine derivatives |
| GR1000662B (el) * | 1988-07-01 | 1992-09-25 | Janssen Pharmaceutica Nv | Μεθοδος παρασκευης cis-ν-(3-μεθοξυ-4-πιπεριδινυλο)βενζαμιδιων. |
| US5262568A (en) * | 1990-03-02 | 1993-11-16 | State Of Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| AU655176B2 (en) | 1990-03-02 | 1994-12-08 | State of Oregon, acting by and through The Oregon Board of Higher Education acting for and on behalf of The Oregon Health Sciences University, Portland, Oregon, and The University of Oregon, Eugene, Oregon | Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists |
| FR2662162B1 (fr) * | 1990-05-18 | 1995-01-20 | Adir | Nouveaux derives de l'amino piperidine, de l'amino pyrrolidine et de l'amino perhydroazepine, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent. |
| JPH05508836A (ja) * | 1990-05-25 | 1993-12-09 | オレゴン州 | シグマ受容体に対して高い結合性を有する置換グアニジンおよびその使用 |
| US5741661A (en) * | 1991-02-08 | 1998-04-21 | Cambridge Neuroscience, Inc. | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| US5847006A (en) * | 1991-02-08 | 1998-12-08 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| CA2099245A1 (en) * | 1991-02-08 | 1992-08-09 | Stanley M. Goldin | Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers |
| FR2690158B1 (fr) * | 1992-04-17 | 1994-07-22 | Sanofi Elf | Nouveau derive arylpiperidinique, procede pour sa preparation et compositions pharmaceutiques le contenant. |
| DK0705100T3 (da) * | 1993-05-27 | 2003-11-17 | Cenes Ltd | Terapeutiske substituerede guanidiner |
| US5739135A (en) * | 1993-09-03 | 1998-04-14 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| AU705487B2 (en) * | 1993-11-23 | 1999-05-20 | Cambridge Neuroscience, Inc. | Therapeutic substituted guanidines |
| US6143791A (en) * | 1994-02-03 | 2000-11-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US7351743B1 (en) | 1994-02-03 | 2008-04-01 | Wyeth | Therapeutic guanidines |
| JPH09509156A (ja) | 1994-02-03 | 1997-09-16 | ケンブリッジ・ニューロサイエンス・インコーポレーテッド | 治療用グアニジン類 |
| US6787569B1 (en) | 1994-02-03 | 2004-09-07 | Cambridge Neuroscience, Inc. | Therapeutic guanidines |
| US6025355A (en) | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
| US6756389B2 (en) | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| DE19824470A1 (de) | 1998-05-30 | 1999-12-02 | Boehringer Ingelheim Pharma | Neue Neurokininantagonisten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3072663A (en) * | 1961-09-25 | 1963-01-08 | Warner Lambert Pharmaceutical | Polyalkyl substituted-4-guanidopiperidines |
| US3161637A (en) * | 1961-10-10 | 1964-12-15 | Res Lab Dr C Janssen N V | 1-(gamma-aroyl-propyl)-4-(nu-arylcarbonyl amino) piperidines and related compounds |
| US3171838A (en) * | 1961-10-10 | 1965-03-02 | Res Lab Dr C Janssen N V | Aroylalkyl and hydroxyaralkyl derivatives of 4-(n-arylalkanamido)-piperidines and related compounds |
| GB1411783A (en) * | 1972-02-24 | 1975-10-29 | Wyeth John & Brother Ltd | Piperidine derivatives |
| GB1411782A (en) * | 1972-02-24 | 1975-10-29 | Wyeth John & Brother Ltd | Piperidine derivatives |
| US3910930A (en) * | 1973-01-04 | 1975-10-07 | Janssen Pharmaceutica Nv | 1-{55 1-{8 2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl{9 -4-piperidyl{56 -2-benzimidazolinones |
| US4177279A (en) * | 1973-10-10 | 1979-12-04 | John Wyeth & Brother Ltd. | 1-[(3-Indolyl)-alkyl]-piperidyl ureas and hypotensive compositions |
| GB1459506A (en) * | 1974-02-18 | 1976-12-22 | Wyeth John & Brother Ltd | Piperidine derivatives |
| JPS5152176A (en, 2012) * | 1974-10-12 | 1976-05-08 | Yoshitomi Pharmaceutical | |
| AU500990B2 (en) * | 1975-07-25 | 1979-06-07 | John Wyeth & Brother Limited | Piperidine derivatives |
| GB1582239A (en) * | 1976-12-11 | 1981-01-07 | Wyeth John & Brother Ltd | Piperidin-4-yl ureas and thioureas |
| GB1561023A (en) * | 1977-04-22 | 1980-02-13 | Beecham Group Ltd | 2-methoxy - 5 - chloro aniline derivatives |
| IN148482B (en, 2012) * | 1977-06-03 | 1981-03-07 | Pfizer | |
| EP0000485A1 (de) * | 1977-07-08 | 1979-02-07 | Ciba-Geigy Ag | Piperidino-propanole, ihre Herstellung und pharmazeutische Präparate die diese enthalten |
| US4281132A (en) * | 1977-10-29 | 1981-07-28 | John Wyeth & Brother Limited | Piperidino ureas and thioureas |
| GB1586817A (en) * | 1977-12-01 | 1981-03-25 | Wyeth John & Brother Ltd | Indole derivatives |
| US4169202A (en) * | 1978-06-05 | 1979-09-25 | American Home Products Corporation | Process for preparing 4,5-dihydro-4-oxofuran-2-carboxylic acid derivatives |
| GB2034305B (en) * | 1978-10-24 | 1982-12-22 | Wyeth John & Brother Ltd | Preparation of piperidine derivatives |
-
1981
- 1981-02-23 PL PL1981234317A patent/PL128510B1/pl unknown
- 1981-02-23 PL PL1981234316A patent/PL135545B1/pl unknown
- 1981-02-23 PH PH25247A patent/PH17019A/en unknown
- 1981-02-23 ES ES499716A patent/ES499716A0/es active Granted
- 1981-02-23 NO NO810610A patent/NO156864C/no unknown
- 1981-02-23 PL PL1981234318A patent/PL128409B1/pl unknown
- 1981-02-23 CA CA000371466A patent/CA1173037A/en not_active Expired
- 1981-02-23 IL IL62200A patent/IL62200A/xx not_active IP Right Cessation
- 1981-02-23 GR GR64215A patent/GR73576B/el unknown
- 1981-02-23 NZ NZ196324A patent/NZ196324A/xx unknown
- 1981-02-23 PL PL1981229830A patent/PL129174B1/pl unknown
- 1981-02-24 AU AU67614/81A patent/AU542950B2/en not_active Expired
- 1981-02-24 PT PT72562A patent/PT72562B/pt unknown
- 1981-02-24 YU YU00473/81A patent/YU47381A/xx unknown
- 1981-02-25 IE IE392/81A patent/IE52014B1/en not_active IP Right Cessation
- 1981-02-25 EG EG69/81D patent/EG16004A/xx active
- 1981-02-25 FI FI810587A patent/FI77231C/fi not_active IP Right Cessation
- 1981-02-26 KR KR1019810000637A patent/KR850000630B1/ko not_active Expired
- 1981-02-26 EP EP81300801A patent/EP0035374B1/en not_active Expired
- 1981-02-26 HU HU81469A patent/HU187768B/hu unknown
- 1981-02-26 DE DE8181300801T patent/DE3168564D1/de not_active Expired
- 1981-02-26 DK DK087881A patent/DK164546C/da not_active IP Right Cessation
-
1982
- 1982-01-29 ES ES509163A patent/ES8302656A1/es not_active Expired
- 1982-01-29 ES ES509164A patent/ES8302657A1/es not_active Expired
- 1982-01-29 ES ES509165A patent/ES509165A0/es active Granted
- 1982-04-07 US US06/366,266 patent/US4426387A/en not_active Expired - Lifetime
-
1983
- 1983-05-04 YU YU00974/83A patent/YU97483A/xx unknown
- 1983-05-04 YU YU00973/83A patent/YU97383A/xx unknown
- 1983-05-04 YU YU00975/83A patent/YU97583A/xx unknown
- 1983-10-26 US US06/545,802 patent/US4563466A/en not_active Expired - Lifetime
-
1984
- 1984-08-24 KR KR1019840005137A patent/KR850001035B1/ko not_active Expired
- 1984-08-24 KR KR1019840005135A patent/KR850000631B1/ko not_active Expired
- 1984-08-24 KR KR1019840005136A patent/KR850001063B1/ko not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |