JP2009521467A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009521467A5 JP2009521467A5 JP2008547546A JP2008547546A JP2009521467A5 JP 2009521467 A5 JP2009521467 A5 JP 2009521467A5 JP 2008547546 A JP2008547546 A JP 2008547546A JP 2008547546 A JP2008547546 A JP 2008547546A JP 2009521467 A5 JP2009521467 A5 JP 2009521467A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidine
- carboxylic acid
- pharmaceutically acceptable
- aminoacetyl
- compound
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- -1 2-aminoacetyl Chemical group 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- DWBJILOIAXQNOL-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(4-hydroxybenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NC(=O)C1=CC=C(O)C=C1 DWBJILOIAXQNOL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000178 monomer Substances 0.000 claims 3
- BIZKIHUJGMSVFD-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NC(=O)C1=CC=CC=C1 BIZKIHUJGMSVFD-UHFFFAOYSA-N 0.000 claims 2
- 206010003662 Atrial flutter Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 230000001746 atrial effect Effects 0.000 claims 2
- 206010061592 cardiac fibrillation Diseases 0.000 claims 2
- BIZKIHUJGMSVFD-MNOVXSKESA-N danegaptide Chemical compound C1[C@@H](C(O)=O)N(C(=O)CN)C[C@@H]1NC(=O)C1=CC=CC=C1 BIZKIHUJGMSVFD-MNOVXSKESA-N 0.000 claims 2
- 230000002600 fibrillogenic effect Effects 0.000 claims 2
- 208000037906 ischaemic injury Diseases 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 208000003663 ventricular fibrillation Diseases 0.000 claims 2
- 206010047302 ventricular tachycardia Diseases 0.000 claims 2
- DWBJILOIAXQNOL-KOLCDFICSA-N (2s,4r)-1-(2-aminoacetyl)-4-[(4-hydroxybenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)CN)C[C@@H]1NC(=O)C1=CC=C(O)C=C1 DWBJILOIAXQNOL-KOLCDFICSA-N 0.000 claims 1
- JDVMUTUTRUIQMU-PWSUYJOCSA-N (2s,4r)-1-(2-aminoacetyl)-4-[(4-methoxybenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(=O)N[C@H]1CN(C(=O)CN)[C@H](C(O)=O)C1 JDVMUTUTRUIQMU-PWSUYJOCSA-N 0.000 claims 1
- XMMUSAHYRGRXKP-NEPJUHHUSA-N (2s,4r)-1-(2-aminoacetyl)-4-[(4-methylbenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)N[C@H]1CN(C(=O)CN)[C@H](C(O)=O)C1 XMMUSAHYRGRXKP-NEPJUHHUSA-N 0.000 claims 1
- JKKQXROZVXIGNK-KOLCDFICSA-N (2s,4r)-1-(2-aminoacetyl)-4-[(4-nitrobenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)CN)C[C@@H]1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 JKKQXROZVXIGNK-KOLCDFICSA-N 0.000 claims 1
- HTXAMMYKSMZQMY-MNOVXSKESA-N (2s,4r)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxamide Chemical compound C1[C@@H](C(N)=O)N(C(=O)CN)C[C@@H]1NC(=O)C1=CC=CC=C1 HTXAMMYKSMZQMY-MNOVXSKESA-N 0.000 claims 1
- XMYARXHHOGTBQV-NEPJUHHUSA-N (2s,4r)-4-benzamido-1-(2-formamidoacetyl)pyrrolidine-2-carboxylic acid Chemical compound C1N(C(=O)CNC=O)[C@H](C(=O)O)C[C@H]1NC(=O)C1=CC=CC=C1 XMYARXHHOGTBQV-NEPJUHHUSA-N 0.000 claims 1
- YEPVKXVZWITHHP-NEPJUHHUSA-N (2s,4r)-4-benzamido-1-[2-(methylamino)acetyl]pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)CNC)C[C@@H]1NC(=O)C1=CC=CC=C1 YEPVKXVZWITHHP-NEPJUHHUSA-N 0.000 claims 1
- KPGGKSWVSBIMSD-KGLIPLIRSA-N (2s,4r)-4-benzamido-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)CNC(=O)OC(C)(C)C)C[C@@H]1NC(=O)C1=CC=CC=C1 KPGGKSWVSBIMSD-KGLIPLIRSA-N 0.000 claims 1
- JDVMUTUTRUIQMU-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(4-methoxybenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C(=O)NC1CN(C(=O)CN)C(C(O)=O)C1 JDVMUTUTRUIQMU-UHFFFAOYSA-N 0.000 claims 1
- XMMUSAHYRGRXKP-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(4-methylbenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)NC1CN(C(=O)CN)C(C(O)=O)C1 XMMUSAHYRGRXKP-UHFFFAOYSA-N 0.000 claims 1
- JKKQXROZVXIGNK-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(4-nitrobenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 JKKQXROZVXIGNK-UHFFFAOYSA-N 0.000 claims 1
- HTXAMMYKSMZQMY-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxamide Chemical compound C1C(C(N)=O)N(C(=O)CN)CC1NC(=O)C1=CC=CC=C1 HTXAMMYKSMZQMY-UHFFFAOYSA-N 0.000 claims 1
- XMYARXHHOGTBQV-UHFFFAOYSA-N 4-benzamido-1-(2-formamidoacetyl)pyrrolidine-2-carboxylic acid Chemical compound C1N(C(=O)CNC=O)C(C(=O)O)CC1NC(=O)C1=CC=CC=C1 XMYARXHHOGTBQV-UHFFFAOYSA-N 0.000 claims 1
- YEPVKXVZWITHHP-UHFFFAOYSA-N 4-benzamido-1-[2-(methylamino)acetyl]pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CNC)CC1NC(=O)C1=CC=CC=C1 YEPVKXVZWITHHP-UHFFFAOYSA-N 0.000 claims 1
- UVVZGPLJJCGVRQ-UHFFFAOYSA-N 4-benzamido-1-[2-[(2,2,2-trifluoroacetyl)amino]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C1N(C(=O)CNC(=O)C(F)(F)F)C(C(=O)O)CC1NC(=O)C1=CC=CC=C1 UVVZGPLJJCGVRQ-UHFFFAOYSA-N 0.000 claims 1
- KPGGKSWVSBIMSD-UHFFFAOYSA-N 4-benzamido-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CNC(=O)OC(C)(C)C)CC1NC(=O)C1=CC=CC=C1 KPGGKSWVSBIMSD-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 description 61
- 125000001072 heteroaryl group Chemical group 0.000 description 48
- 150000002148 esters Chemical class 0.000 description 27
- 150000001413 amino acids Chemical group 0.000 description 26
- 150000004677 hydrates Chemical class 0.000 description 25
- 229940002612 prodrug Drugs 0.000 description 25
- 239000000651 prodrug Substances 0.000 description 25
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 21
- 239000004472 Lysine Substances 0.000 description 21
- 235000018977 lysine Nutrition 0.000 description 21
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 20
- 125000005842 heteroatom Chemical group 0.000 description 20
- 125000003710 aryl alkyl group Chemical group 0.000 description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 125000004404 heteroalkyl group Chemical group 0.000 description 14
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 11
- 239000004475 Arginine Substances 0.000 description 11
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 11
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 11
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 11
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 11
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 11
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 11
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 11
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 11
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 11
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 11
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 11
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 11
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 11
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 11
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 11
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 11
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 11
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 11
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 11
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 11
- 239000004473 Threonine Substances 0.000 description 11
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 11
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 11
- 235000004279 alanine Nutrition 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 229940024606 amino acid Drugs 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 11
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 11
- 235000009697 arginine Nutrition 0.000 description 11
- 235000009582 asparagine Nutrition 0.000 description 11
- 229960001230 asparagine Drugs 0.000 description 11
- 235000003704 aspartic acid Nutrition 0.000 description 11
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 11
- 235000018417 cysteine Nutrition 0.000 description 11
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 11
- 235000013922 glutamic acid Nutrition 0.000 description 11
- 239000004220 glutamic acid Substances 0.000 description 11
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 11
- 235000004554 glutamine Nutrition 0.000 description 11
- 235000014304 histidine Nutrition 0.000 description 11
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 11
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 11
- 229960000310 isoleucine Drugs 0.000 description 11
- 229930182817 methionine Natural products 0.000 description 11
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 11
- 235000004400 serine Nutrition 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 235000008521 threonine Nutrition 0.000 description 11
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 11
- 239000004474 valine Substances 0.000 description 11
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 10
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 0 CN(*)[C@@](C[C@@]1C(*)=O)CN1C(C(*)*)=O Chemical compound CN(*)[C@@](C[C@@]1C(*)=O)CN1C(C(*)*)=O 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 5
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 5
- 150000003852 triazoles Chemical class 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical compound OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- PGXFRGHJXDPFSG-UHFFFAOYSA-N 1-(2-aminopropanoyl)-4-benzamidopiperidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)C(N)C)CCC1NC(=O)C1=CC=CC=C1 PGXFRGHJXDPFSG-UHFFFAOYSA-N 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- DHHUBZSDZXWGLP-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-(5-phenyl-1h-imidazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1C1=NC(C=2C=CC=CC=2)=CN1 DHHUBZSDZXWGLP-UHFFFAOYSA-N 0.000 description 2
- RZIYTPSLDCOJQZ-UHFFFAOYSA-N 1-(2-aminopropanoyl)-4-benzamidopyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)C(N)C)CC1NC(=O)C1=CC=CC=C1 RZIYTPSLDCOJQZ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 2
- BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical class NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000001980 alanyl group Chemical group 0.000 description 2
- 125000005600 alkyl phosphonate group Chemical group 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000009510 drug design Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- BNZBMEIFAOYZEA-UHFFFAOYSA-N n-cyanoacetamide Chemical compound CC(=O)NC#N BNZBMEIFAOYZEA-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IUYNNZGFAZFAQV-OLZOCXBDSA-N (2s,4r)-1-(2-acetamidoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)CNC(=O)C)C[C@@H]1NC(=O)C1=CC=CC=C1 IUYNNZGFAZFAQV-OLZOCXBDSA-N 0.000 description 1
- AJSQJHBBBQFNQL-KOLCDFICSA-N (2s,4r)-1-(2-aminoacetyl)-4-(benzenesulfonamido)pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)CN)C[C@@H]1NS(=O)(=O)C1=CC=CC=C1 AJSQJHBBBQFNQL-KOLCDFICSA-N 0.000 description 1
- VDUZIECBQGRUTB-NEPJUHHUSA-N (2s,4r)-1-(2-aminoacetyl)-4-(benzylamino)pyrrolidine-2-carboxylic acid Chemical compound C1[C@@H](C(O)=O)N(C(=O)CN)C[C@@H]1NCC1=CC=CC=C1 VDUZIECBQGRUTB-NEPJUHHUSA-N 0.000 description 1
- AGAZXYKIVDSJHE-NEPJUHHUSA-N (2s,4r)-4-benzamido-1-(1h-imidazole-2-carbonyl)pyrrolidine-2-carboxylic acid Chemical compound C([C@@H](C[C@H]1C(=O)O)NC(=O)C=2C=CC=CC=2)N1C(=O)C1=NC=CN1 AGAZXYKIVDSJHE-NEPJUHHUSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- ABZPRXZMPSNFMV-UHFFFAOYSA-N 1-(2-amino-3-phenylpropanoyl)-4-benzamidopiperidine-2-carboxylic acid Chemical compound C1CC(NC(=O)C=2C=CC=CC=2)CC(C(O)=O)N1C(=O)C(N)CC1=CC=CC=C1 ABZPRXZMPSNFMV-UHFFFAOYSA-N 0.000 description 1
- KKMHWRXQITVTBJ-UHFFFAOYSA-N 1-(2-amino-4-carboxybutanoyl)-3-benzoylimidazolidine-2-carboxylic acid Chemical compound OC(=O)C1N(C(=O)C(CCC(O)=O)N)CCN1C(=O)C1=CC=CC=C1 KKMHWRXQITVTBJ-UHFFFAOYSA-N 0.000 description 1
- IHTMKMJKWYSGLI-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-(4-phenyl-1,3-oxazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1C1=NC(C=2C=CC=CC=2)=CO1 IHTMKMJKWYSGLI-UHFFFAOYSA-N 0.000 description 1
- BKGFCIHHVSSKPI-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-(5-phenyl-1,3-oxazol-2-yl)pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1C1=NC=C(C=2C=CC=CC=2)O1 BKGFCIHHVSSKPI-UHFFFAOYSA-N 0.000 description 1
- AJSQJHBBBQFNQL-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-(benzenesulfonamido)pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NS(=O)(=O)C1=CC=CC=C1 AJSQJHBBBQFNQL-UHFFFAOYSA-N 0.000 description 1
- VDUZIECBQGRUTB-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-(benzylamino)pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NCC1=CC=CC=C1 VDUZIECBQGRUTB-UHFFFAOYSA-N 0.000 description 1
- QWFSVLRJILNQKU-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-(phenacylamino)pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NCC(=O)C1=CC=CC=C1 QWFSVLRJILNQKU-UHFFFAOYSA-N 0.000 description 1
- WQQDQGHMVARVSR-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-(pyrimidine-5-carbonylamino)pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NC(=O)C1=CN=CN=C1 WQQDQGHMVARVSR-UHFFFAOYSA-N 0.000 description 1
- UELHIZYUZPWHCG-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(2-fluorobenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NC(=O)C1=CC=CC=C1F UELHIZYUZPWHCG-UHFFFAOYSA-N 0.000 description 1
- ITBROHKQJIOMHP-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(2-methylbenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound CC1=CC=CC=C1C(=O)NC1CN(C(=O)CN)C(C(O)=O)C1 ITBROHKQJIOMHP-UHFFFAOYSA-N 0.000 description 1
- PPHDSZVHEDKINH-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(2-phenylacetyl)amino]pyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NC(=O)CC1=CC=CC=C1 PPHDSZVHEDKINH-UHFFFAOYSA-N 0.000 description 1
- FWRDSZCQDGIPEI-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-[(3-methylbenzoyl)amino]pyrrolidine-2-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2CN(C(C2)C(O)=O)C(=O)CN)=C1 FWRDSZCQDGIPEI-UHFFFAOYSA-N 0.000 description 1
- CDLXIBYNVGEIOW-UHFFFAOYSA-N 1-(2-aminoacetyl)-4-anilinopyrrolidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CN)CC1NC1=CC=CC=C1 CDLXIBYNVGEIOW-UHFFFAOYSA-N 0.000 description 1
- XSNJKRVDDZIKLL-UHFFFAOYSA-N 1-benzoyl-3-(2-hydroxyacetyl)imidazolidine-2-carboxamide Chemical compound NC(=O)C1N(C(=O)CO)CCN1C(=O)C1=CC=CC=C1 XSNJKRVDDZIKLL-UHFFFAOYSA-N 0.000 description 1
- DNAVGNOCCXMWGU-UHFFFAOYSA-N 1-benzoyl-3-(2-hydroxyacetyl)imidazolidine-2-carboxylic acid Chemical compound OC(=O)C1N(C(=O)CO)CCN1C(=O)C1=CC=CC=C1 DNAVGNOCCXMWGU-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 description 1
- KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 1
- JCZAVVUIFWZMQI-UHFFFAOYSA-N 1h-thieno[2,3-d]imidazole Chemical compound N1C=NC2=C1C=CS2 JCZAVVUIFWZMQI-UHFFFAOYSA-N 0.000 description 1
- VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
- GOFWAZBPPMEXNJ-UHFFFAOYSA-N 2-[(1-benzoylimidazolidine-2-carbonyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1NCCN1C(=O)C1=CC=CC=C1 GOFWAZBPPMEXNJ-UHFFFAOYSA-N 0.000 description 1
- OOUHUXLLFPJKIE-UHFFFAOYSA-N 2-[(3,5-diaminobenzoyl)amino]acetic acid Chemical compound NC1=CC(N)=CC(C(=O)NCC(O)=O)=C1 OOUHUXLLFPJKIE-UHFFFAOYSA-N 0.000 description 1
- RCZAYQDERJASIA-UHFFFAOYSA-N 2-[(4-amino-1-benzoylpiperidine-4-carbonyl)amino]acetic acid Chemical compound C1CC(N)(C(=O)NCC(O)=O)CCN1C(=O)C1=CC=CC=C1 RCZAYQDERJASIA-UHFFFAOYSA-N 0.000 description 1
- DOKDBMXRHLYMGB-UHFFFAOYSA-N 2-[(4-benzamidopiperidine-2-carbonyl)amino]acetic acid Chemical compound C1CNC(C(=O)NCC(=O)O)CC1NC(=O)C1=CC=CC=C1 DOKDBMXRHLYMGB-UHFFFAOYSA-N 0.000 description 1
- DDLXVTUBYRPCDU-UHFFFAOYSA-N 2-[(4-benzamidopiperidine-2-carbonyl)amino]propanoic acid Chemical compound C1CNC(C(=O)NC(C)C(O)=O)CC1NC(=O)C1=CC=CC=C1 DDLXVTUBYRPCDU-UHFFFAOYSA-N 0.000 description 1
- YPFIAGRUDBCYNF-UHFFFAOYSA-N 2-[(4-benzamidopyrrolidine-2-carbonyl)amino]-3-phenylpropanoic acid Chemical compound C1C(NC(=O)C=2C=CC=CC=2)CNC1C(=O)NC(C(=O)O)CC1=CC=CC=C1 YPFIAGRUDBCYNF-UHFFFAOYSA-N 0.000 description 1
- REUPRJCRTIRITC-UHFFFAOYSA-N 2-[(4-benzamidopyrrolidine-2-carbonyl)amino]-4-methylpentanoic acid Chemical compound C1NC(C(=O)NC(CC(C)C)C(O)=O)CC1NC(=O)C1=CC=CC=C1 REUPRJCRTIRITC-UHFFFAOYSA-N 0.000 description 1
- SBPSVDHCZCQLML-UHFFFAOYSA-N 2-[(4-benzamidopyrrolidine-2-carbonyl)amino]acetic acid Chemical compound C1NC(C(=O)NCC(=O)O)CC1NC(=O)C1=CC=CC=C1 SBPSVDHCZCQLML-UHFFFAOYSA-N 0.000 description 1
- QHKRPBOWGIDUPB-UHFFFAOYSA-N 2-[[1-(4-nitrobenzoyl)imidazolidine-2-carbonyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)C1NCCN1C(=O)C1=CC=C([N+]([O-])=O)C=C1 QHKRPBOWGIDUPB-UHFFFAOYSA-N 0.000 description 1
- AVSKXAORDQWIJU-UHFFFAOYSA-N 2-[[2-amino-3-(4-benzamidophenyl)propanoyl]amino]acetic acid Chemical compound C1=CC(CC(N)C(=O)NCC(O)=O)=CC=C1NC(=O)C1=CC=CC=C1 AVSKXAORDQWIJU-UHFFFAOYSA-N 0.000 description 1
- DUQRDGUNTTVYFV-UHFFFAOYSA-N 2-[[3-amino-5-[(4-methylbenzoyl)amino]benzoyl]amino]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC(N)=CC(C(=O)NCC(O)=O)=C1 DUQRDGUNTTVYFV-UHFFFAOYSA-N 0.000 description 1
- PPIPSFOQVNFQPQ-UHFFFAOYSA-N 2-[[4-[(4-methoxybenzoyl)amino]pyrrolidine-2-carbonyl]amino]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)NC1CC(C(=O)NCC(O)=O)NC1 PPIPSFOQVNFQPQ-UHFFFAOYSA-N 0.000 description 1
- UHEXTCYUAQJLLH-UHFFFAOYSA-N 2-[[4-[(4-nitrobenzoyl)amino]pyrrolidine-2-carbonyl]amino]acetic acid Chemical compound C1NC(C(=O)NCC(=O)O)CC1NC(=O)C1=CC=C([N+]([O-])=O)C=C1 UHEXTCYUAQJLLH-UHFFFAOYSA-N 0.000 description 1
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- QIBXDEKSOQIMRS-UHFFFAOYSA-N 3-[(2-aminoacetyl)amino]-5-[(4-methylbenzoyl)amino]benzoic acid Chemical compound C1=CC(C)=CC=C1C(=O)NC1=CC(NC(=O)CN)=CC(C(O)=O)=C1 QIBXDEKSOQIMRS-UHFFFAOYSA-N 0.000 description 1
- LPRUJVQUSXNWFD-UHFFFAOYSA-N 3-[(4-benzamidopyrrolidine-2-carbonyl)amino]propanoic acid Chemical compound C1NC(C(=O)NCCC(=O)O)CC1NC(=O)C1=CC=CC=C1 LPRUJVQUSXNWFD-UHFFFAOYSA-N 0.000 description 1
- SOXHDHIGOVNDRW-UHFFFAOYSA-N 3-benzamido-5-[(2,4-diamino-4-oxobutanoyl)amino]benzoic acid Chemical compound OC(=O)C1=CC(NC(=O)C(CC(N)=O)N)=CC(NC(=O)C=2C=CC=CC=2)=C1 SOXHDHIGOVNDRW-UHFFFAOYSA-N 0.000 description 1
- WHBLTZLKXOVOGI-UHFFFAOYSA-N 4-amino-2-[(4-benzamidopyrrolidine-2-carbonyl)amino]-4-oxobutanoic acid Chemical compound C1NC(C(=O)NC(CC(=O)N)C(O)=O)CC1NC(=O)C1=CC=CC=C1 WHBLTZLKXOVOGI-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- AGAZXYKIVDSJHE-UHFFFAOYSA-N 4-benzamido-1-(1h-imidazole-2-carbonyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CC(NC(=O)C=2C=CC=CC=2)CN1C(=O)C1=NC=CN1 AGAZXYKIVDSJHE-UHFFFAOYSA-N 0.000 description 1
- YCVJAXONGLDJJB-UHFFFAOYSA-N 4-benzamido-1-(1h-imidazole-5-carbonyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CC(NC(=O)C=2C=CC=CC=2)CN1C(=O)C1=CN=CN1 YCVJAXONGLDJJB-UHFFFAOYSA-N 0.000 description 1
- WCKKIBAKNWBFJQ-UHFFFAOYSA-N 4-benzamido-1-(1h-pyrazole-5-carbonyl)pyrrolidine-2-carboxylic acid Chemical class OC(=O)C1CC(NC(=O)C=2C=CC=CC=2)CN1C(=O)C1=CC=NN1 WCKKIBAKNWBFJQ-UHFFFAOYSA-N 0.000 description 1
- AHJSFKXUVHZYEC-UHFFFAOYSA-N 4-benzamido-1-(2-hydroxyacetyl)piperidine-2-carboxylic acid Chemical compound C1C(C(O)=O)N(C(=O)CO)CCC1NC(=O)C1=CC=CC=C1 AHJSFKXUVHZYEC-UHFFFAOYSA-N 0.000 description 1
- XJDOOPPGIYZOFW-UHFFFAOYSA-N 4-benzamidopyrrolidine-2-carboxylic acid Chemical compound C1NC(C(=O)O)CC1NC(=O)C1=CC=CC=C1 XJDOOPPGIYZOFW-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- NKDWHLARLLEGAO-UHFFFAOYSA-N C1C(CNC1C(=O)N)NC(=O)C2=CC=CC=C2 Chemical compound C1C(CNC1C(=O)N)NC(=O)C2=CC=CC=C2 NKDWHLARLLEGAO-UHFFFAOYSA-N 0.000 description 1
- OAYBEDNAVLBHHV-UHFFFAOYSA-N C1CN(CC1NC(=O)C2=CC(=CC=C2)O)C(=O)CN Chemical compound C1CN(CC1NC(=O)C2=CC(=CC=C2)O)C(=O)CN OAYBEDNAVLBHHV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241000288147 Meleagris gallopavo Species 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- WFIHKLWVLPBMIQ-UHFFFAOYSA-N [1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC=NC2=C1 WFIHKLWVLPBMIQ-UHFFFAOYSA-N 0.000 description 1
- YNDUPGQMECPWKD-UHFFFAOYSA-N [O-][N+](=O)S[N+]([O-])=O Chemical compound [O-][N+](=O)S[N+]([O-])=O YNDUPGQMECPWKD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000001998 leucyl group Chemical group 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 125000001288 lysyl group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- OHZYAOYVLLHTGW-UHFFFAOYSA-N pyrido[3,2-c]pyridazine Chemical compound C1=CN=NC2=CC=CN=C21 OHZYAOYVLLHTGW-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 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 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RBRCCWBAMGPRSN-UHFFFAOYSA-N thieno[2,3-d][1,3]thiazole Chemical compound S1C=NC2=C1C=CS2 RBRCCWBAMGPRSN-UHFFFAOYSA-N 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 description 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US75362805P | 2005-12-23 | 2005-12-23 | |
| US60/753,628 | 2005-12-23 | ||
| PCT/US2006/048790 WO2007078990A2 (en) | 2005-12-23 | 2006-12-21 | Modified lysine-mimetic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009521467A JP2009521467A (ja) | 2009-06-04 |
| JP2009521467A5 true JP2009521467A5 (enExample) | 2013-04-04 |
| JP5473334B2 JP5473334B2 (ja) | 2014-04-16 |
Family
ID=38110525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008547546A Active JP5473334B2 (ja) | 2005-12-23 | 2006-12-21 | 修飾リジン模倣化合物 |
Country Status (26)
| Country | Link |
|---|---|
| US (4) | US7622496B2 (enExample) |
| EP (2) | EP1966130B1 (enExample) |
| JP (1) | JP5473334B2 (enExample) |
| KR (1) | KR101397915B1 (enExample) |
| CN (2) | CN101336229B (enExample) |
| AR (1) | AR058748A1 (enExample) |
| AU (1) | AU2006332945C1 (enExample) |
| BR (1) | BRPI0620436B8 (enExample) |
| CA (1) | CA2634743C (enExample) |
| CR (1) | CR10089A (enExample) |
| DK (1) | DK1966130T3 (enExample) |
| EC (1) | ECSP088633A (enExample) |
| ES (1) | ES2443242T3 (enExample) |
| GT (1) | GT200800123A (enExample) |
| HN (1) | HN2008000957A (enExample) |
| IL (1) | IL192395A (enExample) |
| NZ (1) | NZ569293A (enExample) |
| PE (1) | PE20070849A1 (enExample) |
| PL (1) | PL1966130T3 (enExample) |
| PT (1) | PT1966130E (enExample) |
| RU (1) | RU2494095C2 (enExample) |
| SG (1) | SG170767A1 (enExample) |
| SI (1) | SI1966130T1 (enExample) |
| TW (1) | TWI411597B (enExample) |
| UA (1) | UA96283C2 (enExample) |
| WO (1) | WO2007078990A2 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101336229B (zh) * | 2005-12-23 | 2012-06-13 | 西兰岛药物有限公司 | 改性的拟赖氨酸化合物 |
| PL2468724T3 (pl) * | 2006-12-21 | 2016-05-31 | Zealand Pharma As | Synteza związków pirolidynowych |
| JP2010533690A (ja) * | 2007-07-15 | 2010-10-28 | ジーランド・ファーマ・ア／エス | ペプチドギャップ結合モジュレーター |
| US8377968B2 (en) | 2008-06-02 | 2013-02-19 | Zalicus Pharmaceuticals, Ltd. | N-piperidinyl acetamide derivatives as calcium channel blockers |
| CA2771612A1 (en) * | 2009-09-18 | 2011-03-24 | Zalicus Pharmaceuticals Ltd. | Selective calcium channel modulators |
| WO2013109991A1 (en) * | 2012-01-20 | 2013-07-25 | Acucela Inc. | Substituted heterocyclic compounds for disease treatment |
| EP2961403A4 (en) | 2013-03-01 | 2016-11-30 | Zalicus Pharmaceuticals Ltd | HETEROCYCLIC INHIBITORS OF SODIUM CHANNEL |
| US10179781B2 (en) | 2013-03-15 | 2019-01-15 | Chromocell Corporation | Sodium channel modulators for the treatment of pain |
| EP3043787B1 (en) * | 2013-09-10 | 2018-09-05 | Chromocell Corporation | Sodium channel modulators for the treatment of pain and diabetes |
| WO2015116846A1 (en) * | 2014-01-30 | 2015-08-06 | The Board Of Trustees Of The Leland Stanford Junior University | Modulation of tissue transglutaminase activation in disease |
| KR20160127025A (ko) * | 2014-02-28 | 2016-11-02 | 히칼 리미티드 | 빌다글립틴의 신규하고 경제적인 제조 |
| WO2018202865A1 (en) | 2017-05-05 | 2018-11-08 | Zealand Pharma A/S | Gap junction intercellular communication modulators and their use for the treatment of diabetic eye disease |
| AU2018311976B2 (en) * | 2017-08-04 | 2022-10-13 | Takeda Pharmaceutical Company Limited | Inhibitors of Plasma Kallikrein and uses thereof |
| CN111094233B (zh) | 2017-08-09 | 2024-03-15 | 戴纳立制药公司 | 化合物、组合物及方法 |
| PT3676297T (pt) | 2017-09-01 | 2023-08-29 | Denali Therapeutics Inc | Compostos, composições e métodos |
| EP3684366A4 (en) | 2017-09-22 | 2021-09-08 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES OF THE LATEST |
| WO2019060742A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc | AGENTS FOR DEGRADING PROTEINS AND USES THEREOF |
| IL315310A (en) | 2017-12-26 | 2024-10-01 | Kymera Therapeutics Inc | Irak degraders and uses thereof |
| EP3737675A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | Crbn ligands and uses thereof |
| WO2019140380A1 (en) | 2018-01-12 | 2019-07-18 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| US11292792B2 (en) | 2018-07-06 | 2022-04-05 | Kymera Therapeutics, Inc. | Tricyclic CRBN ligands and uses thereof |
| WO2020010227A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Protein degraders and uses thereof |
| US11352350B2 (en) | 2018-11-30 | 2022-06-07 | Kymera Therapeutics, Inc. | IRAK degraders and uses thereof |
| CA3129609A1 (en) | 2019-02-13 | 2020-08-20 | Denali Therapeutics Inc. | Eukaryotic initiation factor 2b modulators |
| MA54959A (fr) | 2019-02-13 | 2021-12-22 | Denali Therapeutics Inc | Composés, compositions et procédés |
| SG11202110829YA (en) | 2019-04-05 | 2021-10-28 | Kymera Therapeutics Inc | Stat degraders and uses thereof |
| CN112142823B (zh) * | 2019-06-28 | 2022-08-05 | 深圳翰宇药业股份有限公司 | 一种zp-1609的合成方法 |
| WO2020264499A1 (en) | 2019-06-28 | 2020-12-30 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| CN114340670A (zh) | 2019-07-11 | 2022-04-12 | 普拉克西斯精密药物股份有限公司 | T-型钙通道调节剂的制剂及其使用方法 |
| WO2021127283A2 (en) | 2019-12-17 | 2021-06-24 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| EP4076520A4 (en) | 2019-12-17 | 2024-03-27 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| BR112022012410A2 (pt) | 2019-12-23 | 2022-08-30 | Kymera Therapeutics Inc | Degradadores smarca e usos dos mesmos |
| PH12022552458A1 (en) | 2020-03-19 | 2024-01-22 | Kymera Therapeutics Inc | Mdm2 degraders and uses thereof |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| WO2022120355A1 (en) | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead degraders and uses thereof |
| TW202241891A (zh) | 2020-12-30 | 2022-11-01 | 美商凱麥拉醫療公司 | Irak降解劑及其用途 |
| US20240108598A1 (en) | 2021-02-10 | 2024-04-04 | Breye Therapeutics Aps | Danegaptide for Use in the Treatment or Prevention of a Kidney Disease |
| JP2024506656A (ja) | 2021-02-15 | 2024-02-14 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋ４分解剤およびその使用 |
| US12097261B2 (en) | 2021-05-07 | 2024-09-24 | Kymera Therapeutics, Inc. | CDK2 degraders and uses thereof |
| IL312330A (en) | 2021-10-25 | 2024-06-01 | Kymera Therapeutics Inc | Tyk2 degraders and uses thereof |
| WO2023076556A1 (en) | 2021-10-29 | 2023-05-04 | Kymera Therapeutics, Inc. | Irak4 degraders and synthesis thereof |
| CN118450892A (zh) | 2021-12-22 | 2024-08-06 | 布雷耶疗法有限公司 | 缝隙连接调节剂及其用于治疗年龄相关性黄斑变性的用途 |
| JP2025504059A (ja) | 2022-01-31 | 2025-02-06 | カイメラ セラピューティクス， インコーポレイテッド | Ｉｒａｋデグレーダー及びその使用 |
Family Cites Families (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1125587B (de) * | 1957-03-06 | 1962-03-15 | Schering Ag | Roentgenkontrastmittel |
| US4462943A (en) | 1980-11-24 | 1984-07-31 | E. R. Squibb & Sons, Inc. | Carboxyalkyl amino acid derivatives of various substituted prolines |
| ZA817601B (en) * | 1980-11-24 | 1982-10-27 | Squibb & Sons Inc | Carboxyalkyl amino acid derivatives of various substituted prolines |
| ATE22692T1 (de) | 1981-08-03 | 1986-10-15 | Squibb & Sons Inc | Phosphonamidate verbindungen. |
| EP0088350B1 (en) | 1982-03-08 | 1985-02-20 | Schering Corporation | Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them |
| US4514391A (en) | 1983-07-21 | 1985-04-30 | E. R. Squibb & Sons, Inc. | Hydroxy substituted peptide compounds |
| US5684016A (en) * | 1984-04-12 | 1997-11-04 | Hoechst Aktiengesellschaft | Method of treating cardiac insufficiency |
| US4560506A (en) | 1984-05-25 | 1985-12-24 | E. R. Squibb & Sons, Inc. | Mercaptocycloalkylcarbonyl and mercaptoarylcarbonyl dipeptides |
| EP0175266B1 (en) * | 1984-09-12 | 1996-03-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Antihypertensive derivatives |
| US4746676A (en) * | 1984-09-12 | 1988-05-24 | Rorer Pharmaceutical Corporation | Carboxyalkyl dipeptide compounds |
| JPS61148198A (ja) | 1984-12-22 | 1986-07-05 | Ajinomoto Co Inc | 新規トリペプチド化合物および甘味剤 |
| JPS6259296A (ja) | 1985-09-10 | 1987-03-14 | Green Cross Corp:The | ペプタイド誘導体 |
| EP0566157A1 (en) | 1986-06-20 | 1993-10-20 | Schering Corporation | Neutral metalloendopeptidase inhibitors in the treatment of hypertension |
| EP0254032A3 (en) | 1986-06-20 | 1990-09-05 | Schering Corporation | Neutral metalloendopeptidase inhibitors in the treatment of hypertension |
| US4849525A (en) | 1987-09-21 | 1989-07-18 | E. R. Squibb & Sons, Inc. | Phosphinylcycloalkylcarbonyl and phosphinylcycloalkenylcarbonyl dipeptides |
| US5120859A (en) * | 1989-09-22 | 1992-06-09 | Genentech, Inc. | Chimeric amino acid analogues |
| FR2700166B1 (fr) * | 1993-01-07 | 1995-02-17 | Rhone Poulenc Rorer Sa | Dérivés de pyrrolidine, leur préparation et les médicaments les contenant. |
| KR960705808A (ko) | 1993-11-09 | 1996-11-08 | 조셉 에프. 디프리마 | 성장 호르몬의 방출을 촉진시키는 피페리딘, 피롤리딘 및 헥사하이드로-1H-아제핀(Piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone) |
| DE4408531A1 (de) | 1994-03-14 | 1995-09-28 | Hoechst Ag | PNA-Synthese unter Verwendung einer gegen schwache Säuren labilen Amino-Schutzgruppe |
| GB9409150D0 (en) | 1994-05-09 | 1994-06-29 | Black James Foundation | Cck and gastrin receptor ligands |
| JPH0892207A (ja) * | 1994-07-26 | 1996-04-09 | Sankyo Co Ltd | ピロリジン誘導体 |
| US5491164A (en) | 1994-09-29 | 1996-02-13 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| AU2722297A (en) | 1996-04-03 | 1997-10-22 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| SK25099A3 (en) | 1996-08-28 | 2000-02-14 | Procter & Gamble | Substituted cyclic amine metalloprotease inhibitors |
| ATE290014T1 (de) | 1996-09-09 | 2005-03-15 | Zealand Pharma As | Festphasen-peptidsynthese |
| WO1998010653A1 (en) | 1996-09-13 | 1998-03-19 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| UA79749C2 (en) * | 1996-10-18 | 2007-07-25 | Vertex Pharma | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
| WO1998017625A1 (en) * | 1996-10-22 | 1998-04-30 | Daiichi Pharmaceutical Co., Ltd. | Novel remedies for infectious diseases |
| WO1998025897A1 (en) | 1996-12-12 | 1998-06-18 | Merck & Co., Inc. | Piperidines, pyrrolidines and hexahydro-1h-azepines promote release of growth hormone |
| CN1213036C (zh) | 1997-08-22 | 2005-08-03 | 科研制药株式会社 | 新的酰胺类衍生物 |
| US6399629B1 (en) * | 1998-06-01 | 2002-06-04 | Microcide Pharmaceuticals, Inc. | Efflux pump inhibitors |
| RU2243214C2 (ru) * | 1998-06-04 | 2004-12-27 | Астразенека Аб | Новые производные и аналоги 3-арилпропионовой кислоты |
| US6426331B1 (en) * | 1998-07-08 | 2002-07-30 | Tularik Inc. | Inhibitors of STAT function |
| US6242422B1 (en) | 1998-10-22 | 2001-06-05 | Idun Pharmacueticals, Inc. | (Substituted)Acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases |
| HUP0203375A3 (en) | 1999-07-28 | 2005-03-29 | Aventis Pharm Prod Inc | Substituted oxoazaheterocyclyl compounds |
| AU780612C (en) | 1999-10-14 | 2005-10-20 | Curis, Inc. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| US6552016B1 (en) | 1999-10-14 | 2003-04-22 | Curis, Inc. | Mediators of hedgehog signaling pathways, compositions and uses related thereto |
| WO2001034594A1 (en) | 1999-11-12 | 2001-05-17 | Guilford Pharmaceuticals, Inc. | Dipeptidyl peptidase iv inhibitors and methods of making and using dipeptidyl peptidase iv inhibitors |
| EP1226160B1 (en) | 2000-02-23 | 2004-12-15 | Zealand Pharma A/S | Novel antiarrhythmic peptides |
| CA2404314A1 (en) | 2000-03-31 | 2001-10-11 | Lorin Andrew Thompson | Succinoylamino heterocycles as inhibitors of a.beta. protein production |
| AU2001253633A1 (en) | 2000-04-17 | 2001-10-30 | Idun Pharmaceuticals, Inc. | Inhibitors of the ice/ced-3 family of cysteine proteases |
| AU2000249828A1 (en) | 2000-05-03 | 2001-11-12 | Taisho Pharmaceutical Co. Ltd. | Stat4 and stat6 binding dipeptide derivatives |
| EP1294752A2 (en) | 2000-06-16 | 2003-03-26 | Curis, Inc. | Angiogenesis-modulating compositions and uses |
| AR029851A1 (es) | 2000-07-21 | 2003-07-16 | Dendreon Corp | Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c |
| US7244721B2 (en) | 2000-07-21 | 2007-07-17 | Schering Corporation | Peptides as NS3-serine protease inhibitors of hepatitis C virus |
| CN1498224A (zh) | 2000-07-21 | 2004-05-19 | ���鹫˾ | 用作丙型肝炎病毒ns3-丝氨酸蛋白酶抑制剂的新型肽 |
| JP2004504407A (ja) | 2000-07-21 | 2004-02-12 | コルバス・インターナショナル・インコーポレイテッド | Ｃ型肝炎ウイルスのｎｓ３−セリンプロテアーゼ阻害剤としての新規ペプチド |
| AU2001282871A1 (en) * | 2000-08-17 | 2002-02-25 | Eli Lilly And Company | Antithrombotic agents |
| DK1387674T3 (en) | 2000-10-13 | 2017-04-10 | Curis Inc | Hedgehog antagonists, methods and uses related thereto |
| US6376514B1 (en) | 2000-10-17 | 2002-04-23 | The Procter & Gamble Co. | Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof |
| FR2816838B1 (fr) | 2000-11-17 | 2004-12-03 | Oreal | Utilisation de derives de l'acide 2-oxothiazolidine- 4-carboxylique comme agents prodesquamants |
| MXPA03007537A (es) | 2001-02-22 | 2005-09-30 | Zealand Pharma As | Usos medicos nuevos de compuestos que facilitan la comunicacion intercelular. |
| EP1408986B1 (en) | 2001-05-08 | 2008-09-24 | Yale University | Proteomimetic compounds and methods |
| EP1425029A4 (en) | 2001-08-10 | 2006-06-07 | Palatin Technologies Inc | PEPTIDOMIMETICS OF BIOLOGICALLY ACTIVE METALLOPEPTIDES |
| WO2003062228A1 (en) | 2002-01-23 | 2003-07-31 | Schering Corporation | Proline compounds as ns3-serine protease inhibitors for use in treatment of hepatites c virus infection |
| WO2003072528A2 (en) | 2002-02-08 | 2003-09-04 | Idun Pharmaceuticals, Inc. | (substituted)acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases |
| US20060128632A1 (en) * | 2002-07-02 | 2006-06-15 | Sharma Sushil K | Peptide inhibitors of smac protein binding to inhibitor of apoptosis proteins (iap) |
| AU2003265853A1 (en) | 2002-08-29 | 2004-03-19 | Curis, Inc. | Hedgehog antagonists, methods and uses related thereto |
| WO2004032834A2 (en) * | 2002-10-04 | 2004-04-22 | Merck & Co., Inc. | Thrombin inhibitors |
| AU2003302084A1 (en) | 2002-11-15 | 2004-06-15 | Bristol-Myers Squibb Company | Open chain prolyl urea-related modulators of androgen receptor function |
| AU2003281986B2 (en) * | 2002-11-25 | 2009-06-04 | Zealand Pharma A/S | Peptide gap junction modulators |
| DE502004009440D1 (de) | 2003-04-03 | 2009-06-10 | Merck Patent Gmbh | Pyrrolidin-1,2-dicarbonsäure-1-(phenylamid)-2-(4-(3-oxo-morpholin-4-yl)-phenylamid) derivate und verwandte verbindungen als inhibitoren des koagulationsfaktors xa zur behandlung von thromboembolischen erkrankungen |
| WO2004099134A2 (en) | 2003-05-05 | 2004-11-18 | Prosidion Ltd. | Glutaminyl based dp iv-inhibitors |
| CN103145715B (zh) | 2003-10-14 | 2016-08-03 | F·霍夫曼-罗须公司 | 作为hcv复制抑制剂的巨环羧酸和酰基磺酰胺 |
| CN1528745A (zh) | 2003-10-21 | 2004-09-15 | 山东大学 | 吡咯烷类基质金属蛋白酶抑制剂及其制备方法 |
| US7507760B2 (en) | 2004-01-22 | 2009-03-24 | Neuromed Pharmaceuticals Ltd. | N-type calcium channel blockers |
| EP1742914A1 (en) | 2004-02-27 | 2007-01-17 | Schering Corporation | Cyclobutenedione groups-containing compounds as inhibitors of hepatitis c virus ns3 serine protease |
| HRP20110694T1 (hr) * | 2004-03-15 | 2011-12-31 | Janssen Pharmaceutica Nv | Novi spojevi kao modulatori opioidnog receptora |
| WO2005095403A2 (en) | 2004-03-30 | 2005-10-13 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| WO2005116009A1 (en) * | 2004-05-18 | 2005-12-08 | Schering Corporation | Substituted 2-quinolyl-oxazoles useful as pde4 inhibitors |
| EP1604977A1 (en) * | 2004-06-02 | 2005-12-14 | Faust Pharmaceuticals | CIS pyrrolidinyl derivatives and their uses |
| EP2316839B1 (en) | 2004-07-16 | 2014-03-12 | Gilead Sciences, Inc. | Antiviral heterocyclic compounds having phosphonate groups |
| US7820699B2 (en) | 2005-04-27 | 2010-10-26 | Hoffmann-La Roche Inc. | Cyclic amines |
| CA2606785A1 (en) | 2005-05-19 | 2006-11-23 | Genentech, Inc. | Fibroblast activation protein inhibitor compounds and methods |
| CN101336229B (zh) * | 2005-12-23 | 2012-06-13 | 西兰岛药物有限公司 | 改性的拟赖氨酸化合物 |
| PL2468724T3 (pl) | 2006-12-21 | 2016-05-31 | Zealand Pharma As | Synteza związków pirolidynowych |
-
2006
- 2006-12-21 CN CN2006800518550A patent/CN101336229B/zh active Active
- 2006-12-21 CA CA2634743A patent/CA2634743C/en active Active
- 2006-12-21 PL PL06849152T patent/PL1966130T3/pl unknown
- 2006-12-21 UA UAA200808527A patent/UA96283C2/uk unknown
- 2006-12-21 DK DK06849152.1T patent/DK1966130T3/da active
- 2006-12-21 EP EP06849152.1A patent/EP1966130B1/en active Active
- 2006-12-21 RU RU2008126246/04A patent/RU2494095C2/ru active
- 2006-12-21 CN CN201210106810.6A patent/CN102690221B/zh active Active
- 2006-12-21 WO PCT/US2006/048790 patent/WO2007078990A2/en not_active Ceased
- 2006-12-21 ES ES06849152.1T patent/ES2443242T3/es active Active
- 2006-12-21 EP EP11166328.2A patent/EP2386539B1/en active Active
- 2006-12-21 BR BRPI0620436A patent/BRPI0620436B8/pt active IP Right Grant
- 2006-12-21 JP JP2008547546A patent/JP5473334B2/ja active Active
- 2006-12-21 US US11/643,192 patent/US7622496B2/en active Active
- 2006-12-21 SG SG201102116-9A patent/SG170767A1/en unknown
- 2006-12-21 AU AU2006332945A patent/AU2006332945C1/en active Active
- 2006-12-21 KR KR1020087018182A patent/KR101397915B1/ko not_active Expired - Fee Related
- 2006-12-21 NZ NZ569293A patent/NZ569293A/en not_active IP Right Cessation
- 2006-12-21 PT PT68491521T patent/PT1966130E/pt unknown
- 2006-12-21 SI SI200631729T patent/SI1966130T1/sl unknown
- 2006-12-22 TW TW095148422A patent/TWI411597B/zh active
- 2006-12-22 PE PE2006001691A patent/PE20070849A1/es not_active Application Discontinuation
- 2006-12-26 AR ARP060105793A patent/AR058748A1/es not_active Application Discontinuation
-
2008
- 2008-06-19 CR CR10089A patent/CR10089A/es not_active Application Discontinuation
- 2008-06-20 HN HN2008000957A patent/HN2008000957A/es unknown
- 2008-06-20 GT GT200800123A patent/GT200800123A/es unknown
- 2008-06-23 IL IL192395A patent/IL192395A/en not_active IP Right Cessation
- 2008-07-18 EC EC2008008633A patent/ECSP088633A/es unknown
-
2009
- 2009-10-30 US US12/610,172 patent/US8026272B2/en active Active
-
2011
- 2011-09-16 US US13/234,956 patent/US8431540B2/en active Active
-
2013
- 2013-04-01 US US13/854,423 patent/US20130225644A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009521467A5 (enExample) | ||
| JP5473334B2 (ja) | 修飾リジン模倣化合物 | |
| JP4472691B2 (ja) | 神経変性疾患の処置のための１−フェニルアルカンカルボン酸誘導体 | |
| JP2010513283A5 (enExample) | ||
| AU781003B2 (en) | 8,8A-dihydro-indeno(1,2-D)thiazole derivatives, substituted in position 8A, a method for their production and their use as medicaments, e.g. anorectic agents | |
| SK288422B6 (sk) | Omega-aminoalkylamidy kyseliny (R)-2-arylpropiónovej a ich použitie ako liečivo | |
| CN1372548A (zh) | 杂环化合物及其医药用途 | |
| CA2513408A1 (en) | Mono-acylated o-phenylendiamines derivatives and their use against cancer | |
| JPH10500986A (ja) | 金属タンパク質分解酵素阻害剤 | |
| RU2014120013A (ru) | Амидные производные n-карбамид-замещенных аминокислот как модуляторы формилпептидного рецептора-1 (fprl-1) | |
| RU2263113C2 (ru) | Производные 8,8а-дигидроиндено [1,2-d]тиазола, содержащие в положении 2 заместитель с сульфонамидной или сульфоновой структурой, способ их получения и их применение в качестве лекарственного средства | |
| WO2011145669A1 (ja) | アミド誘導体 | |
| JP2009537595A5 (enExample) | ||
| CA2744425A1 (en) | Quinazoline inhibitors of bace 1 and methods of using | |
| CN1303372A (zh) | 新的杂环取代酰胺、其制备以及应用 | |
| RU2528826C2 (ru) | Новые бензолсульфонамидные соединения, способ их получения и применение в терапии и косметике | |
| US20220251112A1 (en) | Process for preparation of edoxaban | |
| JP4866851B2 (ja) | 神経変性疾患の処置のための１−フェニルアルカンカルボン酸の誘導体 | |
| US6277876B1 (en) | Matrix metalloproteinase inhibitors | |
| US7217707B2 (en) | Amide of R-2-(aminoaryl)-propionic acid for use in the prevention of leucocyte activation | |
| SK16222002A3 (sk) | Amidy (R)-enantiomérov 2-arylpropiónových kyselín, spôsob ich výroby, farmaceutický prostriedok s ich obsahom a ich použitie | |
| JP2005272419A (ja) | ヒストン脱アセチル化酵素阻害剤 | |
| JPWO2005035471A1 (ja) | エーテル誘導体 | |
| AU2001246539A1 (en) | Amides of R-2-(aminoaryl)-propionic acids for use in the prevention of leucocyte activation | |
| US10000474B2 (en) | Histone deacetylase inhibitors and uses thereof |