JP2003506355A5 - - Google Patents
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- JP2003506355A5 JP2003506355A5 JP2001514300A JP2001514300A JP2003506355A5 JP 2003506355 A5 JP2003506355 A5 JP 2003506355A5 JP 2001514300 A JP2001514300 A JP 2001514300A JP 2001514300 A JP2001514300 A JP 2001514300A JP 2003506355 A5 JP2003506355 A5 JP 2003506355A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- methyl
- hydrogen
- benzamide
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 229910052739 hydrogen Inorganic materials 0.000 description 193
- 239000001257 hydrogen Substances 0.000 description 193
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 154
- 125000003118 aryl group Chemical group 0.000 description 154
- 125000000217 alkyl group Chemical group 0.000 description 120
- 125000000623 heterocyclic group Chemical group 0.000 description 104
- 150000001875 compounds Chemical class 0.000 description 88
- -1 amidoalkyl Chemical group 0.000 description 87
- 125000003710 aryl alkyl group Chemical group 0.000 description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 75
- 125000003302 alkenyloxy group Chemical group 0.000 description 54
- 125000001188 haloalkyl group Chemical group 0.000 description 39
- 150000002431 hydrogen Chemical class 0.000 description 38
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 33
- 125000003342 alkenyl group Chemical group 0.000 description 30
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 description 27
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 27
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 27
- 125000004966 cyanoalkyl group Chemical group 0.000 description 27
- 125000000753 cycloalkyl group Chemical group 0.000 description 27
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
- 125000004093 cyano group Chemical group *C#N 0.000 description 22
- 201000010099 disease Diseases 0.000 description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 18
- 239000008194 pharmaceutical composition Substances 0.000 description 18
- 125000004076 pyridyl group Chemical group 0.000 description 17
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 16
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 16
- 125000001544 thienyl group Chemical group 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 description 11
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 7
- 125000001475 halogen functional group Chemical group 0.000 description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
- 125000004438 haloalkoxy group Chemical group 0.000 description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 208000008967 Enuresis Diseases 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 3
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- ZEBGRPVZGUGIFN-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1 ZEBGRPVZGUGIFN-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- JHLOXZBALBYGLY-UHFFFAOYSA-N 4-methyl-n-[2,2,2-trifluoro-1-(phenylcarbamothioylamino)ethyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(F)(F)F)NC(=S)NC1=CC=CC=C1 JHLOXZBALBYGLY-UHFFFAOYSA-N 0.000 description 2
- 208000000187 Abnormal Reflex Diseases 0.000 description 2
- 201000004384 Alopecia Diseases 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- 208000005171 Dysmenorrhea Diseases 0.000 description 2
- 206010013935 Dysmenorrhoea Diseases 0.000 description 2
- 208000030814 Eating disease Diseases 0.000 description 2
- 208000010228 Erectile Dysfunction Diseases 0.000 description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 description 2
- 206010057671 Female sexual dysfunction Diseases 0.000 description 2
- 206010020853 Hypertonic bladder Diseases 0.000 description 2
- 206010022562 Intermittent claudication Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 206010036018 Pollakiuria Diseases 0.000 description 2
- 208000005107 Premature Birth Diseases 0.000 description 2
- 206010036590 Premature baby Diseases 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- 206010037211 Psychomotor hyperactivity Diseases 0.000 description 2
- 208000022901 Reynold syndrome Diseases 0.000 description 2
- 208000016717 Reynolds syndrome Diseases 0.000 description 2
- 206010046543 Urinary incontinence Diseases 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
- 125000005336 allyloxy group Chemical group 0.000 description 2
- 231100000360 alopecia Toxicity 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000005961 cardioprotection Effects 0.000 description 2
- 235000014632 disordered eating Nutrition 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 206010020745 hyperreflexia Diseases 0.000 description 2
- 230000035859 hyperreflexia Effects 0.000 description 2
- 201000001881 impotence Diseases 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 208000021156 intermittent vascular claudication Diseases 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 206010036596 premature ejaculation Diseases 0.000 description 2
- QXPARVLZIKNFEQ-UHFFFAOYSA-N 2-[1-(6-chloro-3-oxo-1h-isoindol-2-yl)-2,2-dimethylpropyl]-1-cyano-3-pyridin-3-ylguanidine Chemical compound C1C2=CC(Cl)=CC=C2C(=O)N1C(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1 QXPARVLZIKNFEQ-UHFFFAOYSA-N 0.000 description 1
- VGWAEGVIAGYXPR-UHFFFAOYSA-N 2-tert-butyl-3-(4-chlorobenzoyl)-n-cyano-n'-pyridin-3-ylimidazolidine-1-carboximidamide Chemical compound CC(C)(C)C1N(C(NC=2C=NC=CC=2)=NC#N)CCN1C(=O)C1=CC=C(Cl)C=C1 VGWAEGVIAGYXPR-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- QKQHYQRTAIIYFF-UHFFFAOYSA-N 4-chloro-n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethyl-4-sulfamoylbutyl]benzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(CCS(N)(=O)=O)C)NC(=NC#N)NC1=CC=CN=C1 QKQHYQRTAIIYFF-UHFFFAOYSA-N 0.000 description 1
- MKMVNHFGQFNVAD-UHFFFAOYSA-N 4-chloro-n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-2-fluorobenzamide Chemical compound C=1C=C(Cl)C=C(F)C=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1 MKMVNHFGQFNVAD-UHFFFAOYSA-N 0.000 description 1
- DCGRLPHOFDXNNR-UHFFFAOYSA-N 4-chloro-n-[1-[[(cyanoamino)-(pyrimidin-5-ylamino)methylidene]amino]-2,2-dimethylpropyl]-2-fluorobenzamide Chemical compound C=1C=C(Cl)C=C(F)C=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CN=CN=C1 DCGRLPHOFDXNNR-UHFFFAOYSA-N 0.000 description 1
- BZHJDQYBCGAWSO-UHFFFAOYSA-N 4-chloro-n-[1-[[(cyanoamino)-[(4-ethylpyridin-3-yl)amino]methylidene]amino]-2,2-dimethylpropyl]-2-fluorobenzamide Chemical compound CCC1=CC=NC=C1NC(=NC#N)NC(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1F BZHJDQYBCGAWSO-UHFFFAOYSA-N 0.000 description 1
- FIAIGTYMYOTVDD-UHFFFAOYSA-N 4-chloro-n-[2,2-dichloro-1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-4-sulfamoylbutyl]benzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(Cl)(Cl)CCS(=O)(=O)N)NC(=NC#N)NC1=CC=CN=C1 FIAIGTYMYOTVDD-UHFFFAOYSA-N 0.000 description 1
- PWRTXFFFEVPTCB-UHFFFAOYSA-N 4-chloro-n-[2,2-dimethyl-1-[[(pyridin-3-ylamino)-(sulfamoylamino)methylidene]amino]propyl]benzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(C)C)NC(=NS(N)(=O)=O)NC1=CC=CN=C1 PWRTXFFFEVPTCB-UHFFFAOYSA-N 0.000 description 1
- OIDGAGNPJXRINB-UHFFFAOYSA-N 4-chloro-n-[3,3-dimethyl-1-[[(pyridin-3-ylamino)-(sulfamoylamino)methylidene]amino]butyl]benzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(CC(C)(C)C)NC(=NS(N)(=O)=O)NC1=CC=CN=C1 OIDGAGNPJXRINB-UHFFFAOYSA-N 0.000 description 1
- VGBPSZXWFHTUCI-GOSISDBHSA-N 4-methyl-n-[(1r)-2-[(2-methylpropan-2-yl)oxy]-1-[(3-nitrophenyl)carbamothioylamino]ethyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)N[C@@H](COC(C)(C)C)NC(=S)NC1=CC=CC([N+]([O-])=O)=C1 VGBPSZXWFHTUCI-GOSISDBHSA-N 0.000 description 1
- VGHBOZCMKOXANF-UHFFFAOYSA-N 4-methyl-n-[2,2,2-trichloro-1-(phenylcarbamoylamino)ethyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(Cl)(Cl)Cl)NC(=O)NC1=CC=CC=C1 VGHBOZCMKOXANF-UHFFFAOYSA-N 0.000 description 1
- IPPPTPWWCMPFDH-UHFFFAOYSA-N 4-methyl-n-[2,2,2-trichloro-1-(pyridin-3-ylcarbamoylamino)ethyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(Cl)(Cl)Cl)NC(=O)NC1=CC=CN=C1 IPPPTPWWCMPFDH-UHFFFAOYSA-N 0.000 description 1
- ZFYCYFNABYGTHG-UHFFFAOYSA-N 4-methyl-n-[2,2,2-trichloro-1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]ethyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(Cl)(Cl)Cl)NC(=NC#N)NC1=CC=CN=C1 ZFYCYFNABYGTHG-UHFFFAOYSA-N 0.000 description 1
- PRRSTBPLKWZJMK-UHFFFAOYSA-N 4-methyl-n-[2,2,2-trifluoro-1-(pyridin-3-ylcarbamothioylamino)ethyl]benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(F)(F)F)NC(=S)NC1=CC=CN=C1 PRRSTBPLKWZJMK-UHFFFAOYSA-N 0.000 description 1
- HOAQWQRXTKZKDD-UHFFFAOYSA-N CC(C)(C)C(C(C=C(C=C1)Cl)=C1C(N)=O)NC(NC(C=NC(Br)=C1)=C1F)=NC#N Chemical compound CC(C)(C)C(C(C=C(C=C1)Cl)=C1C(N)=O)NC(NC(C=NC(Br)=C1)=C1F)=NC#N HOAQWQRXTKZKDD-UHFFFAOYSA-N 0.000 description 1
- FSRVDPQHOBNVHK-UHFFFAOYSA-N CC(C)(C)C(C(C=C(C=C1)I)=C1C(N)=O)NC(NC1=CC=CN=C1)=NC#N Chemical compound CC(C)(C)C(C(C=C(C=C1)I)=C1C(N)=O)NC(NC1=CC=CN=C1)=NC#N FSRVDPQHOBNVHK-UHFFFAOYSA-N 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 description 1
- 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 description 1
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- XJQDTCIZMLBFMP-UHFFFAOYSA-N methyl 4-[(4-chlorobenzoyl)amino]-4-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-3,3-dimethylbutanoate Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(C)CC(=O)OC)NC(=NC#N)NC1=CC=CN=C1 XJQDTCIZMLBFMP-UHFFFAOYSA-N 0.000 description 1
- AGDSSJIOIMSADQ-QGZVFWFLSA-N n-[(1r)-2,2-dimethyl-1-(pyridin-3-ylcarbamothioylamino)propyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N[C@@H](C(C)(C)C)NC(=S)NC1=CC=CN=C1 AGDSSJIOIMSADQ-QGZVFWFLSA-N 0.000 description 1
- AGDSSJIOIMSADQ-KRWDZBQOSA-N n-[(1s)-2,2-dimethyl-1-(pyridin-3-ylcarbamothioylamino)propyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N[C@H](C(C)(C)C)NC(=S)NC1=CC=CN=C1 AGDSSJIOIMSADQ-KRWDZBQOSA-N 0.000 description 1
- AHDUOIQGEBOCAO-UHFFFAOYSA-N n-[1-[(2,3-difluorophenyl)carbamothioylamino]-2,2,2-trifluoroethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(F)(F)F)NC(=S)NC1=CC=CC(F)=C1F AHDUOIQGEBOCAO-UHFFFAOYSA-N 0.000 description 1
- LPWLQBLDQZKREE-UHFFFAOYSA-N n-[1-[(2,5-difluorophenyl)carbamothioylamino]-2,2,2-trifluoroethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(F)(F)F)NC(=S)NC1=CC(F)=CC=C1F LPWLQBLDQZKREE-UHFFFAOYSA-N 0.000 description 1
- QUJJKTNTKNVWRZ-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)carbamothioylamino]-2,2,2-trifluoroethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(F)(F)F)NC(=S)NC1=CC=C(Cl)N=C1 QUJJKTNTKNVWRZ-UHFFFAOYSA-N 0.000 description 1
- IINYSOZDOONMIH-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(3-fluoroanilino)methylidene]amino]-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CC(F)=C1 IINYSOZDOONMIH-UHFFFAOYSA-N 0.000 description 1
- SZSFSBAJCVOQDZ-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-2-fluoro-4-sulfamoylbenzamide Chemical compound C=1C=C(S(N)(=O)=O)C=C(F)C=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1 SZSFSBAJCVOQDZ-UHFFFAOYSA-N 0.000 description 1
- YOHQIZCCEHJROI-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1 YOHQIZCCEHJROI-UHFFFAOYSA-N 0.000 description 1
- AYGVYGRNTGYPAI-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-2-phenylacetamide Chemical compound C=1C=CN=CC=1NC(=NC#N)NC(C(C)(C)C)NC(=O)CC1=CC=CC=C1 AYGVYGRNTGYPAI-UHFFFAOYSA-N 0.000 description 1
- HJDNONAVGSVGOE-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-3,5-difluorobenzamide Chemical compound C=1C(F)=CC(F)=CC=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1 HJDNONAVGSVGOE-UHFFFAOYSA-N 0.000 description 1
- XCHPMYOIMGUTCW-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC(NC(NC=2C=NC=CC=2)=NC#N)C(C)(C)C)=C1 XCHPMYOIMGUTCW-UHFFFAOYSA-N 0.000 description 1
- NVAUSEBIFREFCV-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-3-phenylpropanamide Chemical compound C=1C=CN=CC=1NC(=NC#N)NC(C(C)(C)C)NC(=O)CCC1=CC=CC=C1 NVAUSEBIFREFCV-UHFFFAOYSA-N 0.000 description 1
- ULVNJYUOZJJAOD-UHFFFAOYSA-N n-[1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]-2,2-dimethylpropyl]-4-fluorobenzamide Chemical compound C=1C=C(F)C=CC=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1 ULVNJYUOZJJAOD-UHFFFAOYSA-N 0.000 description 1
- JXRVLNPWNRLCCS-UHFFFAOYSA-N n-[1-[[[(2-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dimethylpropyl]-4-chlorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=CN=C1Br JXRVLNPWNRLCCS-UHFFFAOYSA-N 0.000 description 1
- JPOFWFBWBZPMGD-UHFFFAOYSA-N n-[1-[[[(4-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2,2-trichloroethyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC(C(Cl)(Cl)Cl)NC(=NC#N)NC1=CN=CC=C1Br JPOFWFBWBZPMGD-UHFFFAOYSA-N 0.000 description 1
- QSAFIEDBPCYLQI-UHFFFAOYSA-N n-[1-[[[(5-aminoperoxysulfanylpyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dimethylpropyl]-4-chlorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CN=CC(SOON)=C1 QSAFIEDBPCYLQI-UHFFFAOYSA-N 0.000 description 1
- XKXXKWYPBYIYBO-UHFFFAOYSA-N n-[1-[[[(5-bromo-4-ethylpyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dimethylpropyl]-4-chlorobenzamide Chemical compound CCC1=C(Br)C=NC=C1NC(=NC#N)NC(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 XKXXKWYPBYIYBO-UHFFFAOYSA-N 0.000 description 1
- YDPLOPXIEHMLDV-UHFFFAOYSA-N n-[1-[[[(5-bromo-6-chloropyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dimethylpropyl]-4-chlorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CN=C(Cl)C(Br)=C1 YDPLOPXIEHMLDV-UHFFFAOYSA-N 0.000 description 1
- LCBPIAMOSXMBDA-UHFFFAOYSA-N n-[1-[[[(5-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dimethylpropyl]-4-chlorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CN=CC(Br)=C1 LCBPIAMOSXMBDA-UHFFFAOYSA-N 0.000 description 1
- PNVVUEVMWCOCCM-UHFFFAOYSA-N n-[1-[[[(6-bromopyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dimethylpropyl]-4-chlorobenzamide Chemical compound C=1C=C(Cl)C=CC=1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=C(Br)N=C1 PNVVUEVMWCOCCM-UHFFFAOYSA-N 0.000 description 1
- BNGGBVOISPXMPB-UHFFFAOYSA-N n-[1-[[[(6-chloropyridin-3-yl)amino]-(cyanoamino)methylidene]amino]-2,2-dimethylpropyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(C)(C)C)NC(=NC#N)NC1=CC=C(Cl)N=C1 BNGGBVOISPXMPB-UHFFFAOYSA-N 0.000 description 1
- DULQRJDLNFVZDO-UHFFFAOYSA-N n-[1-[[anilino-(cyanoamino)methylidene]amino]-2,2,2-trichloroethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(Cl)(Cl)Cl)NC(=NC#N)NC1=CC=CC=C1 DULQRJDLNFVZDO-UHFFFAOYSA-N 0.000 description 1
- HOVVJCUXRJKERL-UHFFFAOYSA-N n-[1-adamantyl-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]methyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC(C12CC3CC(CC(C3)C1)C2)NC(=NC#N)NC1=CC=CN=C1 HOVVJCUXRJKERL-UHFFFAOYSA-N 0.000 description 1
- YVIXLNPHCMOKBE-UHFFFAOYSA-N n-[2,2,2-trichloro-1-(pyridin-3-ylcarbamoylamino)ethyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C(Cl)(Cl)Cl)NC(=O)NC1=CC=CN=C1 YVIXLNPHCMOKBE-UHFFFAOYSA-N 0.000 description 1
- USNLQXVJCGGNOX-UHFFFAOYSA-N n-[2,2,2-trichloro-1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]ethyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C(Cl)(Cl)Cl)NC(=NC#N)NC1=CC=CN=C1 USNLQXVJCGGNOX-UHFFFAOYSA-N 0.000 description 1
- UOHSXGWRHRNIMP-UHFFFAOYSA-N n-[2,2-dichloro-1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]propyl]-3,5-difluorobenzamide Chemical compound C=1C(F)=CC(F)=CC=1C(=O)NC(C(Cl)(Cl)C)NC(=NC#N)NC1=CC=CN=C1 UOHSXGWRHRNIMP-UHFFFAOYSA-N 0.000 description 1
- IETHEAUZLFFESN-UHFFFAOYSA-N n-[2,2-dimethyl-1-(pyridin-3-ylcarbamothioylamino)propyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC(C(C)(C)C)NC(=S)NC1=CC=CN=C1 IETHEAUZLFFESN-UHFFFAOYSA-N 0.000 description 1
- AGDSSJIOIMSADQ-UHFFFAOYSA-N n-[2,2-dimethyl-1-(pyridin-3-ylcarbamothioylamino)propyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(C)(C)C)NC(=S)NC1=CC=CN=C1 AGDSSJIOIMSADQ-UHFFFAOYSA-N 0.000 description 1
- HYPVVDFQMIUCNC-UHFFFAOYSA-N n-[2,2-dimethyl-1-(pyridin-3-ylcarbamothioylamino)propyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C(C)(C)C)NC(=S)NC1=CC=CN=C1 HYPVVDFQMIUCNC-UHFFFAOYSA-N 0.000 description 1
- CZLSITUXPFHZHR-UHFFFAOYSA-N n-[2,2-dimethyl-1-[(3-nitrophenyl)carbamothioylamino]propyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(C(C)(C)C)NC(=S)NC1=CC=CC([N+]([O-])=O)=C1 CZLSITUXPFHZHR-UHFFFAOYSA-N 0.000 description 1
- WRUJLAJJKQLHKL-UHFFFAOYSA-N n-[2,2-dimethyl-1-[[nitramido-(pyridin-3-ylamino)methylidene]amino]propyl]-4-phenylbenzamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)NC(C(C)(C)C)NC(=N[N+]([O-])=O)NC1=CC=CN=C1 WRUJLAJJKQLHKL-UHFFFAOYSA-N 0.000 description 1
- FFTIPVXSPAOHSO-UHFFFAOYSA-N n-[2-(1-adamantyl)-1-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]ethyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC(NC(NC=1C=NC=CC=1)=NC#N)CC1(C2)CC(C3)CC2CC3C1 FFTIPVXSPAOHSO-UHFFFAOYSA-N 0.000 description 1
- VWDFAVQIGJBWIY-UHFFFAOYSA-N n-[2-(1-adamantyl)-1-[[nitramido-(pyridin-3-ylamino)methylidene]amino]ethyl]-4-chlorobenzamide Chemical compound C=1C=CN=CC=1NC(=N[N+](=O)[O-])NC(CC12CC3CC(CC(C3)C1)C2)NC(=O)C1=CC=C(Cl)C=C1 VWDFAVQIGJBWIY-UHFFFAOYSA-N 0.000 description 1
- UXAFJJSBSSWVRB-UHFFFAOYSA-N n-[2-fluoro-1-[(3-nitrophenyl)carbamothioylamino]ethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC(CF)NC(=S)NC1=CC=CC([N+]([O-])=O)=C1 UXAFJJSBSSWVRB-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- OPWRXDJBNOZKJV-UXHICEINSA-N tert-butyl (2r)-2-[(s)-[(4-chlorobenzoyl)amino]-[[(cyanoamino)-(pyridin-3-ylamino)methylidene]amino]methyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1[C@@H](NC(=O)C=1C=CC(Cl)=CC=1)NC(=NC#N)NC1=CC=CN=C1 OPWRXDJBNOZKJV-UXHICEINSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36477199A | 1999-08-03 | 1999-08-03 | |
| US09/364,771 | 1999-08-03 | ||
| US62115400A | 2000-07-21 | 2000-07-21 | |
| US09/621,154 | 2000-07-21 | ||
| PCT/US2000/021054 WO2001009096A2 (en) | 1999-08-03 | 2000-08-02 | Potassium channel openers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003506355A JP2003506355A (ja) | 2003-02-18 |
| JP2003506355A5 true JP2003506355A5 (https=) | 2007-09-20 |
Family
ID=27002637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001514300A Pending JP2003506355A (ja) | 1999-08-03 | 2000-08-02 | カリウムチャンネル開放剤 |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1198456B1 (https=) |
| JP (1) | JP2003506355A (https=) |
| AT (1) | ATE373642T1 (https=) |
| CA (1) | CA2378936A1 (https=) |
| DE (1) | DE60036476T2 (https=) |
| ES (1) | ES2292462T3 (https=) |
| MX (1) | MXPA02001207A (https=) |
| WO (1) | WO2001009096A2 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6645968B2 (en) * | 1999-08-03 | 2003-11-11 | Abbott Laboratories | Potassium channel openers |
| US6946474B2 (en) | 2000-09-14 | 2005-09-20 | Merck & Co., Inc. | Nitrogen-containing compounds and their use as glycine transport inhibitors |
| WO2002062761A1 (en) * | 2001-02-07 | 2002-08-15 | Abbott Laboratories | Aminal diones as potassium channel openers |
| IL158574A0 (en) | 2001-05-24 | 2004-05-12 | Leo Pharma As | Novel pyridyl cyanoguanidine compounds |
| US7920906B2 (en) | 2005-03-10 | 2011-04-05 | Dexcom, Inc. | System and methods for processing analyte sensor data for sensor calibration |
| US9247900B2 (en) | 2004-07-13 | 2016-02-02 | Dexcom, Inc. | Analyte sensor |
| US8989833B2 (en) | 2004-07-13 | 2015-03-24 | Dexcom, Inc. | Transcutaneous analyte sensor |
| JP5189367B2 (ja) * | 2004-12-22 | 2013-04-24 | レオ ファーマ アクティーゼルスカブ | 新規シアノグアニジン化合物 |
| EP1917244A2 (de) | 2005-08-24 | 2008-05-07 | Abbott GmbH & Co. KG | Hetaryl substituierte guanidinverbindungen und ihre verwendung als bindungspartner für 5-ht5-rezeptoren |
| US9604931B2 (en) | 2007-01-22 | 2017-03-28 | Gtx, Inc. | Nuclear receptor binding agents |
| ES2475193T3 (es) | 2007-01-22 | 2014-07-10 | Gtx, Inc. | Agentes de unión al receptor nuclear |
| US9623021B2 (en) | 2007-01-22 | 2017-04-18 | Gtx, Inc. | Nuclear receptor binding agents |
| WO2011140680A1 (zh) * | 2010-05-14 | 2011-11-17 | 中国人民解放军总医院 | 脲类化合物及其抑制细胞凋亡的用途 |
| CN110366691B (zh) * | 2017-03-03 | 2022-02-18 | 日本化药株式会社 | 图像显示装置 |
| CN113683535B (zh) * | 2020-05-18 | 2022-08-30 | 中国药科大学 | 含氰胍结构的化合物及其制备方法与用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1810293A1 (de) * | 1968-11-22 | 1970-06-11 | Bayer Ag | N-Fluoracetylamino-methyl-harnstoffe und Verfahren zu ihrer Herstellung |
| US4146646A (en) * | 1976-02-12 | 1979-03-27 | Fisons Limited | Bis-amide fungicidal compounds |
| MX170706B (es) * | 1989-02-03 | 1993-09-08 | Lilly Co Eli | Procedimiento para la preparacion de (-) -n"ciano-n-3- piridil -n'- 1, 2, 2-trimetilpropilguanidina |
| US5140031A (en) * | 1989-05-31 | 1992-08-18 | E. R. Squibb & Sons, Inc. | Pyranyl cyanoguanidine derivatives |
| JPH05294935A (ja) * | 1991-03-15 | 1993-11-09 | Green Cross Corp:The | アミノピリジン系化合物 |
| DK28893D0 (da) * | 1993-03-15 | 1993-03-15 | Neurosearch As | Benzimidazole derivater, deres fremstilling og anvendelse |
| GB9407432D0 (en) * | 1994-04-14 | 1994-06-08 | Zeneca Ltd | Heterocyclic derivative |
| US5565483A (en) * | 1995-06-07 | 1996-10-15 | Bristol-Myers Squibb Company | 3-substituted oxindole derivatives as potassium channel modulators |
| US6191140B1 (en) * | 1998-10-28 | 2001-02-20 | Abbott Laboratories | Pyrano, piperidino, and thiopyrano compounds and methods of use |
| EP1133474B1 (en) * | 1998-12-04 | 2007-02-21 | Bristol-Myers Squibb Company | 3-substituted-4-arylquinolin-2-one derivatives as potassium channel modulators |
-
2000
- 2000-08-02 AT AT00955327T patent/ATE373642T1/de not_active IP Right Cessation
- 2000-08-02 ES ES00955327T patent/ES2292462T3/es not_active Expired - Lifetime
- 2000-08-02 WO PCT/US2000/021054 patent/WO2001009096A2/en not_active Ceased
- 2000-08-02 CA CA002378936A patent/CA2378936A1/en not_active Abandoned
- 2000-08-02 JP JP2001514300A patent/JP2003506355A/ja active Pending
- 2000-08-02 DE DE60036476T patent/DE60036476T2/de not_active Expired - Lifetime
- 2000-08-02 EP EP00955327A patent/EP1198456B1/en not_active Expired - Lifetime
- 2000-08-02 MX MXPA02001207A patent/MXPA02001207A/es unknown
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