ZA200307321B - Substituted propane-1,3-diamine derivatives and the pharmaceutical use thereof. - Google Patents
Substituted propane-1,3-diamine derivatives and the pharmaceutical use thereof. Download PDFInfo
- Publication number
- ZA200307321B ZA200307321B ZA200307321A ZA200307321A ZA200307321B ZA 200307321 B ZA200307321 B ZA 200307321B ZA 200307321 A ZA200307321 A ZA 200307321A ZA 200307321 A ZA200307321 A ZA 200307321A ZA 200307321 B ZA200307321 B ZA 200307321B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- aryl
- cycloalkyl
- syn
- denotes
- Prior art date
Links
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 title description 4
- 125000003118 aryl group Chemical group 0.000 claims description 127
- 125000000623 heterocyclic group Chemical group 0.000 claims description 56
- -1 -(Ci.¢-alkyl)- aryl Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 206010012735 Diarrhoea Diseases 0.000 claims description 4
- 208000003251 Pruritus Diseases 0.000 claims description 4
- 208000009205 Tinnitus Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 230000007803 itching Effects 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 231100000886 tinnitus Toxicity 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- KNNGVMHGNVLLJF-UHFFFAOYSA-N 1-[2-[phenyl(pyrrolidin-3-yl)methyl]cyclohexyl]pyrrolidine Chemical compound C1CCCN1C1C(C(C2CNCC2)C=2C=CC=CC=2)CCCC1 KNNGVMHGNVLLJF-UHFFFAOYSA-N 0.000 claims description 2
- IGZOKUVEYDHRGX-UHFFFAOYSA-N 1-[2-methyl-1-(2-pyrrolidin-1-ylcyclohexyl)propyl]piperidine Chemical compound C1CCCCN1C(C(C)C)C1CCCCC1N1CCCC1 IGZOKUVEYDHRGX-UHFFFAOYSA-N 0.000 claims description 2
- SRTOWTKPZYRHEL-UHFFFAOYSA-N 1-[phenyl-(2-pyrrolidin-1-ylcyclohexyl)methyl]piperidine Chemical compound C1CCCN1C1C(C(N2CCCCC2)C=2C=CC=CC=2)CCCC1 SRTOWTKPZYRHEL-UHFFFAOYSA-N 0.000 claims description 2
- AQBYNAXUHUVNEP-UHFFFAOYSA-N 2-methyl-1,3-diphenyl-3-piperidin-1-yl-n-propylpropan-1-amine Chemical compound C=1C=CC=CC=1C(NCCC)C(C)C(C=1C=CC=CC=1)N1CCCCC1 AQBYNAXUHUVNEP-UHFFFAOYSA-N 0.000 claims description 2
- PSHBZXDMIIMNHJ-UHFFFAOYSA-N 4-(1,3-diphenyl-3-pyrrolidin-1-ylpropyl)morpholine Chemical compound C1COCCN1C(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)N1CCCC1 PSHBZXDMIIMNHJ-UHFFFAOYSA-N 0.000 claims description 2
- DYAYPYUZZFUKQN-UHFFFAOYSA-N 4-[phenyl-(2-pyrrolidin-1-ylcyclohexyl)methyl]morpholine Chemical compound C1CCCN1C1C(C(N2CCOCC2)C=2C=CC=CC=2)CCCC1 DYAYPYUZZFUKQN-UHFFFAOYSA-N 0.000 claims description 2
- PGCXBRJNQLPNEX-UHFFFAOYSA-N n,n,2-trimethyl-1,3-diphenyl-3-pyrrolidin-1-ylpropan-1-amine Chemical compound C1CCCN1C(C=1C=CC=CC=1)C(C)C(N(C)C)C1=CC=CC=C1 PGCXBRJNQLPNEX-UHFFFAOYSA-N 0.000 claims description 2
- MWYQAKHUTWIFNY-UHFFFAOYSA-N n,n,2-trimethyl-3-morpholin-4-yl-1-phenylpentan-1-amine Chemical compound C1COCCN1C(CC)C(C)C(N(C)C)C1=CC=CC=C1 MWYQAKHUTWIFNY-UHFFFAOYSA-N 0.000 claims description 2
- GTFFELNJEONHLC-UHFFFAOYSA-N n,n-diethyl-n',n',2-trimethyl-1,3-diphenylpropane-1,3-diamine Chemical compound C=1C=CC=CC=1C(N(CC)CC)C(C)C(N(C)C)C1=CC=CC=C1 GTFFELNJEONHLC-UHFFFAOYSA-N 0.000 claims description 2
- FBVWYDRZROMVJE-UHFFFAOYSA-N n,n-dimethyl-1-(2-morpholin-4-ylcyclohexyl)-1-phenylmethanamine Chemical compound C=1C=CC=CC=1C(N(C)C)C1CCCCC1N1CCOCC1 FBVWYDRZROMVJE-UHFFFAOYSA-N 0.000 claims description 2
- CDYYOAXWNXFBGI-UHFFFAOYSA-N n-benzyl-2-[dimethylamino(phenyl)methyl]cyclohexan-1-amine Chemical compound C=1C=CC=CC=1C(N(C)C)C1CCCCC1NCC1=CC=CC=C1 CDYYOAXWNXFBGI-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 35
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 15
- 238000006243 chemical reaction Methods 0.000 claims 8
- 150000002466 imines Chemical class 0.000 claims 5
- 150000001540 azides Chemical class 0.000 claims 4
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 150000004985 diamines Chemical class 0.000 claims 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
- 238000010792 warming Methods 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical group CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- RNIHAPSVIGPAFF-UHFFFAOYSA-N Acrylamide-acrylic acid resin Chemical compound NC(=O)C=C.OC(=O)C=C RNIHAPSVIGPAFF-UHFFFAOYSA-N 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- 101100043731 Caenorhabditis elegans syx-3 gene Proteins 0.000 claims 1
- 101100535673 Drosophila melanogaster Syn gene Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 101100368134 Mus musculus Syn1 gene Proteins 0.000 claims 1
- 229910020889 NaBH3 Inorganic materials 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 150000007975 iminium salts Chemical class 0.000 claims 1
- FORRYAQDSDQINQ-UHFFFAOYSA-N n,n-dimethyl-1-phenyl-1-(2-pyrrolidin-1-ylcyclohexyl)methanamine Chemical compound C=1C=CC=CC=1C(N(C)C)C1CCCCC1N1CCCC1 FORRYAQDSDQINQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 description 11
- 230000001684 chronic effect Effects 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010010774 Constipation Diseases 0.000 description 2
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 2
- 206010038678 Respiratory depression Diseases 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000006193 alkinyl group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- 229940005483 opioid analgesics Drugs 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 230000008673 vomiting Effects 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 230000002981 neuropathic effect Effects 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000006194 pentinyl group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C07D213/73—Unsubstituted amino or imino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/40—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing only non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/78—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
-
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10108307A DE10108307A1 (de) | 2001-02-21 | 2001-02-21 | Substituierte Propan-1,3-diamin-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200307321B true ZA200307321B (en) | 2005-01-10 |
Family
ID=7674965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200307321A ZA200307321B (en) | 2001-02-21 | 2003-09-18 | Substituted propane-1,3-diamine derivatives and the pharmaceutical use thereof. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US7230018B2 (sk) |
| EP (1) | EP1363885B1 (sk) |
| JP (1) | JP4447837B2 (sk) |
| KR (1) | KR20030091995A (sk) |
| CN (1) | CN100434421C (sk) |
| AR (1) | AR035752A1 (sk) |
| AT (1) | ATE362916T1 (sk) |
| AU (1) | AU2002246095B2 (sk) |
| CA (1) | CA2438704C (sk) |
| CY (1) | CY1106711T1 (sk) |
| CZ (1) | CZ20031968A3 (sk) |
| DE (2) | DE10108307A1 (sk) |
| DK (1) | DK1363885T3 (sk) |
| EC (1) | ECSP034739A (sk) |
| ES (1) | ES2286240T3 (sk) |
| HK (1) | HK1060730A1 (sk) |
| HU (1) | HUP0302746A3 (sk) |
| IL (2) | IL157494A0 (sk) |
| MX (1) | MXPA03006744A (sk) |
| NO (1) | NO20033697L (sk) |
| PE (1) | PE20021007A1 (sk) |
| PL (1) | PL372089A1 (sk) |
| PT (1) | PT1363885E (sk) |
| RU (1) | RU2003127397A (sk) |
| SI (1) | SI1363885T1 (sk) |
| SK (1) | SK286980B6 (sk) |
| WO (1) | WO2002066432A1 (sk) |
| ZA (1) | ZA200307321B (sk) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005061428A1 (de) * | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
| ITMI20120536A1 (it) * | 2012-04-02 | 2013-10-03 | Carlo Angelo Ghisalberti | Composizioni per il trattamento dell¿incontinenza urinaria da stress in soggetti femminili |
| GB201601301D0 (en) * | 2016-01-25 | 2016-03-09 | Takeda Pharmaceutical | Novel compounds |
| CN110021156A (zh) * | 2018-01-10 | 2019-07-16 | 金宝电子工业股份有限公司 | 遥控系统以及遥控方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4017637A (en) * | 1973-03-26 | 1977-04-12 | American Home Products Corporation | Benzylamine analgesics |
| DE19915602A1 (de) | 1999-04-07 | 2000-10-19 | Gruenenthal Gmbh | 3-Amino-4-arylpropan-1-ol-Derivate, deren Herstellung und Verwendung |
| DE19915601A1 (de) * | 1999-04-07 | 2000-10-19 | Gruenenthal Gmbh | 3-Amino-3-arylpropan-1-ol-Derivate, deren Herstellung und Verwendung |
-
2001
- 2001-02-21 DE DE10108307A patent/DE10108307A1/de not_active Withdrawn
-
2002
- 2002-02-19 AR ARP020100567A patent/AR035752A1/es not_active Application Discontinuation
- 2002-02-20 AU AU2002246095A patent/AU2002246095B2/en not_active Ceased
- 2002-02-20 CZ CZ20031968A patent/CZ20031968A3/cs unknown
- 2002-02-20 PL PL02372089A patent/PL372089A1/xx not_active Application Discontinuation
- 2002-02-20 AT AT02714169T patent/ATE362916T1/de active
- 2002-02-20 EP EP02714169A patent/EP1363885B1/de not_active Expired - Lifetime
- 2002-02-20 PE PE2002000142A patent/PE20021007A1/es not_active Application Discontinuation
- 2002-02-20 CA CA2438704A patent/CA2438704C/en not_active Expired - Fee Related
- 2002-02-20 CN CNB028052463A patent/CN100434421C/zh not_active Expired - Fee Related
- 2002-02-20 JP JP2002565949A patent/JP4447837B2/ja not_active Expired - Fee Related
- 2002-02-20 MX MXPA03006744A patent/MXPA03006744A/es active IP Right Grant
- 2002-02-20 DK DK02714169T patent/DK1363885T3/da active
- 2002-02-20 ES ES02714169T patent/ES2286240T3/es not_active Expired - Lifetime
- 2002-02-20 SK SK1030-2003A patent/SK286980B6/sk not_active IP Right Cessation
- 2002-02-20 HU HU0302746A patent/HUP0302746A3/hu unknown
- 2002-02-20 IL IL15749402A patent/IL157494A0/xx unknown
- 2002-02-20 DE DE50210197T patent/DE50210197D1/de not_active Expired - Lifetime
- 2002-02-20 SI SI200230563T patent/SI1363885T1/sl unknown
- 2002-02-20 KR KR10-2003-7011008A patent/KR20030091995A/ko not_active Application Discontinuation
- 2002-02-20 WO PCT/EP2002/001765 patent/WO2002066432A1/de active IP Right Grant
- 2002-02-20 RU RU2003127397/04A patent/RU2003127397A/ru not_active Application Discontinuation
- 2002-02-20 PT PT02714169T patent/PT1363885E/pt unknown
-
2003
- 2003-08-20 IL IL157494A patent/IL157494A/en not_active IP Right Cessation
- 2003-08-20 NO NO20033697A patent/NO20033697L/no not_active Application Discontinuation
- 2003-08-20 EC EC2003004739A patent/ECSP034739A/es unknown
- 2003-08-21 US US10/644,981 patent/US7230018B2/en not_active Expired - Fee Related
- 2003-09-18 ZA ZA200307321A patent/ZA200307321B/en unknown
-
2004
- 2004-05-20 HK HK04103603A patent/HK1060730A1/xx not_active IP Right Cessation
-
2007
- 2007-07-09 CY CY20071100903T patent/CY1106711T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR850001035B1 (ko) | 피페리딘 유도체의 제조방법 | |
| US6127541A (en) | Imidazoquinazoline derivatives | |
| AU751139B2 (en) | Amide derivative | |
| KR100442561B1 (ko) | ５산화２질소신타아제의억제제로유용한환상아미디노제 | |
| AU2005233437A1 (en) | Thienopyridine derivatives | |
| CZ276896A3 (en) | Naphthyl amides as agents for central neural system | |
| WO2003064404A1 (fr) | Hydrazides d'acide 2-furancarboxylique et compositions pharmaceutiques les contenant | |
| RU2003117719A (ru) | Профилактические или лечебные лекарственные средства от диабета, содержащие конденсированные гетероциклические соединения или их соли | |
| WO2013170147A1 (en) | Compounds useful for promoting protein degradation and methods using same | |
| CA2399196A1 (en) | Pyrimidine compounds | |
| SK283394B6 (sk) | Zlúčeniny 4-fenylpiperidínu a jej farmaceuticky prijateľné soli, spôsob ich prípravy, liečivo s ich obsahom a ich použitie | |
| CN111233731B (zh) | 精神药剂及其用途 | |
| ZA200307321B (en) | Substituted propane-1,3-diamine derivatives and the pharmaceutical use thereof. | |
| JP2005325099A (ja) | チエノピリジン誘導体 | |
| SK287069B6 (sk) | Deriváty aminotiazolu, spôsob ich prípravy a farmaceutické kompozície, ktoré ich obsahujú, a ich použitie | |
| WO2001064675A1 (en) | Condensed thiazolamines and their use as neuropeptide y5 antagonists | |
| JPH021439A (ja) | ジアミン化合物、その製法及び該化合物を含有する高血圧症及び炎症を治療するための医薬 | |
| CN110944630A (zh) | 精神药剂及其用途 | |
| JP2007131617A (ja) | チエノピリジン誘導体を含有する医薬 | |
| PL81548B1 (en) | 2,2,-diaryl-4-4-aryl-4-hydroxy-piperidino butyramides[gb1319040a] | |
| CA2742903A1 (en) | Novel bis-amides as antimalarial agents | |
| EP1389611B1 (en) | 20-hydroxyeicosatetraenoic acid production inhibitors | |
| US20040259861A1 (en) | Medicament inhibiting sodium/calcium exchange system | |
| CZ658590A3 (en) | Aminopyridinylmethanols, aminomethylpyridinamines and their derivatives, process of their preparation, pharmaceutical composition containing such compounds and use thereof | |
| JP2005503330A5 (sk) |