ZA200102426B - Drugs for improving vesical excretory strength. - Google Patents
Drugs for improving vesical excretory strength. Download PDFInfo
- Publication number
- ZA200102426B ZA200102426B ZA200102426A ZA200102426A ZA200102426B ZA 200102426 B ZA200102426 B ZA 200102426B ZA 200102426 A ZA200102426 A ZA 200102426A ZA 200102426 A ZA200102426 A ZA 200102426A ZA 200102426 B ZA200102426 B ZA 200102426B
- Authority
- ZA
- South Africa
- Prior art keywords
- carbonyl
- lower alkyl
- alkyl
- phenyl
- carbamoyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 11
- 229940079593 drug Drugs 0.000 title description 3
- -1 amine compound Chemical class 0.000 claims description 406
- 125000000217 alkyl group Chemical group 0.000 claims description 114
- 229910052757 nitrogen Inorganic materials 0.000 claims description 80
- 125000003282 alkyl amino group Chemical group 0.000 claims description 73
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 43
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 229910052760 oxygen Inorganic materials 0.000 claims description 43
- 239000001301 oxygen Chemical group 0.000 claims description 43
- 229910052717 sulfur Chemical group 0.000 claims description 43
- 239000011593 sulfur Chemical group 0.000 claims description 43
- 239000003795 chemical substances by application Substances 0.000 claims description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 38
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 37
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 34
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
- 125000004414 alkyl thio group Chemical group 0.000 claims description 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 210000003932 urinary bladder Anatomy 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 230000027939 micturition Effects 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 206010013990 dysuria Diseases 0.000 claims description 10
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 102000012440 Acetylcholinesterase Human genes 0.000 claims description 5
- 108010022752 Acetylcholinesterase Proteins 0.000 claims description 5
- 229940022698 acetylcholinesterase Drugs 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000000304 alkynyl group Chemical group 0.000 claims 18
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 9
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims 9
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 9
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 9
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 9
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 9
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 9
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 claims 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 9
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 8
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 8
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 4
- 125000003944 tolyl group Chemical group 0.000 claims 4
- 125000001207 fluorophenyl group Chemical group 0.000 claims 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims 3
- RXBYRTSOWREATF-UHFFFAOYSA-N 1,2,3,4-tetrahydroacridine Chemical compound C1=CC=C2C=C(CCCC3)C3=NC2=C1 RXBYRTSOWREATF-UHFFFAOYSA-N 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 125000006196 aroyl alkyl group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims 1
- 125000004212 difluorophenyl group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical class O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 150000002829 nitrogen Chemical class 0.000 claims 1
- 125000005412 pyrazyl group Chemical group 0.000 claims 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000000694 effects Effects 0.000 description 7
- 210000003205 muscle Anatomy 0.000 description 6
- 150000001555 benzenes Chemical group 0.000 description 5
- 230000029142 excretion Effects 0.000 description 5
- 210000005036 nerve Anatomy 0.000 description 5
- 230000000069 prophylactic effect Effects 0.000 description 5
- 239000000544 cholinesterase inhibitor Substances 0.000 description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- 208000026723 Urinary tract disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229960001446 distigmine Drugs 0.000 description 3
- GJHSNEVFXQVOHR-UHFFFAOYSA-L distigmine bromide Chemical compound [Br-].[Br-].C=1C=C[N+](C)=CC=1OC(=O)N(C)CCCCCCN(C)C(=O)OC1=CC=C[N+](C)=C1 GJHSNEVFXQVOHR-UHFFFAOYSA-L 0.000 description 3
- 210000003708 urethra Anatomy 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- NZUPCNDJBJXXRF-UHFFFAOYSA-O bethanechol Chemical compound C[N+](C)(C)CC(C)OC(N)=O NZUPCNDJBJXXRF-UHFFFAOYSA-O 0.000 description 2
- 229960000910 bethanechol Drugs 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000004118 muscle contraction Effects 0.000 description 2
- 229960002362 neostigmine Drugs 0.000 description 2
- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 230000002485 urinary effect Effects 0.000 description 2
- VZUPRYJLEGMFBC-UHFFFAOYSA-N 1-(2,3,4,5-tetrahydro-1h-1-benzazepin-8-yl)propan-1-one Chemical compound C1CCCNC2=CC(C(=O)CC)=CC=C21 VZUPRYJLEGMFBC-UHFFFAOYSA-N 0.000 description 1
- QGMBTMRFZXNSTP-UHFFFAOYSA-N 3-(1-benzylpiperidin-4-yl)-1-[4-(dimethylamino)phenyl]propan-1-one Chemical compound C1=CC(N(C)C)=CC=C1C(=O)CCC1CCN(CC=2C=CC=CC=2)CC1 QGMBTMRFZXNSTP-UHFFFAOYSA-N 0.000 description 1
- NESAEEGNYRYMIJ-UHFFFAOYSA-N 3-(4-benzylpiperazin-1-yl)-3-(5-benzyl-2,3,4,5-tetrahydro-1h-3-benzazepin-8-yl)propanal Chemical compound C=1C=C2C(CC=3C=CC=CC=3)CNCCC2=CC=1C(CC=O)N(CC1)CCN1CC1=CC=CC=C1 NESAEEGNYRYMIJ-UHFFFAOYSA-N 0.000 description 1
- 206010000087 Abdominal pain upper Diseases 0.000 description 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 241000909851 Epiphora Species 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- 101710151321 Melanostatin Proteins 0.000 description 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 description 1
- 206010029279 Neurogenic bladder Diseases 0.000 description 1
- 102400000064 Neuropeptide Y Human genes 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 206010036018 Pollakiuria Diseases 0.000 description 1
- 206010051482 Prostatomegaly Diseases 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000006251 butylcarbonyl group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 125000006637 cyclobutyl carbonyl 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
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 125000006638 cyclopentyl carbonyl group Chemical group 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
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 208000008384 ileus Diseases 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 208000016747 lacrimal apparatus disease Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 210000005037 parasympathetic nerve Anatomy 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 210000005070 sphincter Anatomy 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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US7091218B1 (en) | 1999-09-01 | 2006-08-15 | Eisai Co., Ltd. | 4-substituted piperidine compound |
DE60139781D1 (de) | 2000-06-21 | 2009-10-15 | Eisai R&D Man Co Ltd | 4-substituierte piperidinverbindung |
EP1319661B1 (en) * | 2000-09-21 | 2006-03-01 | Takeda Pharmaceutical Company Limited | Process for producing a tricyclic fused heterocyclic derivative |
US7132547B2 (en) | 2001-12-28 | 2006-11-07 | Takeda Pharmaceutical Company Limited | Preventives/remedies for urinary disturbance |
AU2003207089A1 (en) * | 2003-02-14 | 2004-09-06 | Takeda Pharmaceutical Company Limited | Preparation for topical administration |
CA2531019A1 (en) * | 2003-06-30 | 2005-01-06 | Takeda Pharmaceutical Company Limited | Preventive/remedy for urinary disturbance |
US8597184B2 (en) | 2005-10-18 | 2013-12-03 | Pneumoflex Systems, Llc | Techniques for evaluating urinary stress incontinence and use of involuntary reflex cough as a medical diagnostic tool |
US9011328B2 (en) * | 2005-10-18 | 2015-04-21 | Pneumoflex Systems, Llc | Oral-esophageal-gastric device with esophageal cuff to reduce gastric reflux and/or emesis |
EP1937143B1 (en) * | 2005-10-18 | 2016-11-30 | Pneumoflex Systems, LLC | Apparatus for evaluating urinary stress incontinence |
US8602987B2 (en) | 2005-10-18 | 2013-12-10 | Pneumoflex Systems, Llc | Techniques for evaluating stress urinary incontinence (SUI) using involuntary reflex cough test |
US9028406B2 (en) * | 2005-10-18 | 2015-05-12 | Pneumoflex Systems, Llc | Oral-esophageal-gastric device to diagnose reflux and/or emesis |
PE20070702A1 (es) * | 2005-11-02 | 2007-07-20 | Takeda Pharmaceutical | COMPUESTOS DERIVADOS DE (TRIFLUOROMETOXI-FENIL)-ETILAMINO COMO INHIBIDORES DE LA ACETILCOLINESTERASA Y ANTAGONISTAS DEL RECEPTOR DE ADRENALINA alfa1 |
WO2007081626A2 (en) * | 2005-12-09 | 2007-07-19 | Pneumoflex Systems, Llc | Involuntary contraction induced pressure as a medical diagnostic tool |
US8597183B2 (en) * | 2005-12-09 | 2013-12-03 | Pneumoflex Systems, Llc | Involuntary contraction induced pressure as a medical diagnostic tool using involuntary reflex cough test |
US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
KR100689873B1 (ko) * | 2006-11-10 | 2007-03-12 | 이동언 | 케이블 트레이의 결합구조 |
MX2012008721A (es) | 2010-02-16 | 2012-08-17 | Pfizer | (r)-4-((4-((4-(tetrahidrofuran-3-iloxi)benzo[d]isoxazol-3-iloxi)m etil) tetrahidro-2h-piran-4-ol, un agonista pacial de receptores 5-ht4. |
EP2642998B1 (en) | 2010-11-24 | 2020-09-16 | The Trustees of Columbia University in the City of New York | A non-retinoid rbp4 antagonist for treatment of age-related macular degeneration and stargardt disease |
CN102675206A (zh) * | 2011-03-08 | 2012-09-19 | 中南大学 | 新型乙酰胆碱酯酶抑制剂的制备及其活性 |
RS57497B1 (sr) | 2013-03-14 | 2018-10-31 | Alkermes Pharma Ireland Ltd | Prolekovi fumarata i njihova upotreba u lečenju raznih bolesti |
US8669281B1 (en) | 2013-03-14 | 2014-03-11 | Alkermes Pharma Ireland Limited | Prodrugs of fumarates and their use in treating various diseases |
KR101537400B1 (ko) * | 2013-03-21 | 2015-07-17 | 중앙대학교 산학협력단 | 아세틸콜린을 포함하는 전립선 비대증 치료용 조성물 |
AU2015218587B2 (en) | 2014-02-24 | 2017-04-27 | Alkermes Pharma Ireland Limited | Sulfonamide and sulfinamide prodrugs of fumarates and their use in treating various diseases |
CN104211638A (zh) * | 2014-08-13 | 2014-12-17 | 李增 | 一种脂肪氨基取代的芸香碱类衍生物及其制备和作为抗阿尔兹海默症的药物中的应用 |
CN114652675A (zh) * | 2020-12-23 | 2022-06-24 | 燃点(南京)生物医药科技有限公司 | 一种盐酸乌拉地尔注射液的制备方法 |
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-
1999
- 1999-09-30 KR KR1020017004082A patent/KR100648869B1/ko not_active IP Right Cessation
- 1999-09-30 CA CA002344894A patent/CA2344894A1/en not_active Abandoned
- 1999-09-30 HU HU0104493A patent/HUP0104493A3/hu unknown
- 1999-09-30 AU AU59995/99A patent/AU758802B2/en not_active Ceased
- 1999-09-30 CN CNA2004100396842A patent/CN1535682A/zh active Pending
- 1999-09-30 CN CNA2004100628464A patent/CN1572299A/zh active Pending
- 1999-09-30 BR BR9914163-9A patent/BR9914163A/pt not_active Application Discontinuation
- 1999-09-30 CN CNA200510118165XA patent/CN1768745A/zh active Pending
- 1999-09-30 EP EP05020329A patent/EP1604653A1/en not_active Withdrawn
- 1999-09-30 KR KR1020067004875A patent/KR100639543B1/ko not_active IP Right Cessation
- 1999-09-30 WO PCT/JP1999/005367 patent/WO2000018391A1/ja not_active Application Discontinuation
- 1999-09-30 NZ NZ510685A patent/NZ510685A/en unknown
- 1999-09-30 EP EP07023437A patent/EP1891954A3/en not_active Withdrawn
- 1999-09-30 CN CNB998138894A patent/CN1163224C/zh not_active Expired - Fee Related
- 1999-09-30 EP EP99969675A patent/EP1118322A4/en not_active Withdrawn
-
2001
- 2001-03-23 ZA ZA200102426A patent/ZA200102426B/en unknown
- 2001-03-29 NO NO20011602A patent/NO20011602L/no not_active Application Discontinuation
-
2003
- 2003-12-04 US US10/726,486 patent/US20040116457A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CN1768745A (zh) | 2006-05-10 |
NO20011602L (no) | 2001-05-22 |
EP1604653A1 (en) | 2005-12-14 |
WO2000018391A1 (fr) | 2000-04-06 |
AU5999599A (en) | 2000-04-17 |
CA2344894A1 (en) | 2000-04-06 |
KR20060026972A (ko) | 2006-03-24 |
KR100648869B1 (ko) | 2007-02-28 |
AU758802B2 (en) | 2003-03-27 |
HUP0104493A2 (hu) | 2002-04-29 |
CN1572299A (zh) | 2005-02-02 |
KR100639543B1 (ko) | 2006-10-31 |
NZ510685A (en) | 2003-10-31 |
EP1118322A4 (en) | 2004-10-20 |
BR9914163A (pt) | 2001-08-14 |
NO20011602D0 (no) | 2001-03-29 |
CN1328451A (zh) | 2001-12-26 |
EP1118322A1 (en) | 2001-07-25 |
CN1163224C (zh) | 2004-08-25 |
US20040116457A1 (en) | 2004-06-17 |
CN1535682A (zh) | 2004-10-13 |
KR20010085865A (ko) | 2001-09-07 |
EP1891954A2 (en) | 2008-02-27 |
HUP0104493A3 (en) | 2002-12-28 |
EP1891954A3 (en) | 2009-01-14 |
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