JP2004504297A5 - - Google Patents
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- Publication number
- JP2004504297A5 JP2004504297A5 JP2002512128A JP2002512128A JP2004504297A5 JP 2004504297 A5 JP2004504297 A5 JP 2004504297A5 JP 2002512128 A JP2002512128 A JP 2002512128A JP 2002512128 A JP2002512128 A JP 2002512128A JP 2004504297 A5 JP2004504297 A5 JP 2004504297A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- arylalkyl
- aryl
- methyl
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims 40
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims 23
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- -1 arylcarbonylalkyl Chemical group 0.000 claims 12
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 12
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000001072 heteroaryl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 5
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims 5
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 4
- 208000002249 Diabetes Complications Diseases 0.000 claims 4
- 206010012655 Diabetic complications Diseases 0.000 claims 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 4
- 208000010412 Glaucoma Diseases 0.000 claims 4
- 206010019280 Heart failures Diseases 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 206010040047 Sepsis Diseases 0.000 claims 4
- 206010040070 Septic Shock Diseases 0.000 claims 4
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims 4
- 208000001106 Takayasu Arteritis Diseases 0.000 claims 4
- 206010043540 Thromboangiitis obliterans Diseases 0.000 claims 4
- 206010052779 Transplant rejections Diseases 0.000 claims 4
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims 4
- 206010003119 arrhythmia Diseases 0.000 claims 4
- 230000006793 arrhythmia Effects 0.000 claims 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 4
- 239000000824 cytostatic agent Substances 0.000 claims 4
- 230000001085 cytostatic effect Effects 0.000 claims 4
- 208000010643 digestive system disease Diseases 0.000 claims 4
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
- 208000001286 intracranial vasospasm Diseases 0.000 claims 4
- 208000017169 kidney disease Diseases 0.000 claims 4
- 201000005202 lung cancer Diseases 0.000 claims 4
- 208000020816 lung neoplasm Diseases 0.000 claims 4
- 230000005906 menstruation Effects 0.000 claims 4
- 208000031225 myocardial ischemia Diseases 0.000 claims 4
- 210000000056 organ Anatomy 0.000 claims 4
- 201000011461 pre-eclampsia Diseases 0.000 claims 4
- 230000001681 protective effect Effects 0.000 claims 4
- 208000002815 pulmonary hypertension Diseases 0.000 claims 4
- 230000029663 wound healing Effects 0.000 claims 4
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 102000048186 Endothelin-converting enzyme 1 Human genes 0.000 claims 2
- 108030001679 Endothelin-converting enzyme 1 Proteins 0.000 claims 2
- 102000004157 Hydrolases Human genes 0.000 claims 2
- 108090000604 Hydrolases Proteins 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000011701 zinc Substances 0.000 claims 2
- 229910052725 zinc Inorganic materials 0.000 claims 2
- LVVNTXNLOMBDBY-OCCSQVGLSA-N (2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@@H](S)CN1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 LVVNTXNLOMBDBY-OCCSQVGLSA-N 0.000 claims 1
- DHIQNDDDYDYAOK-VWNXMTODSA-N (2s,4r)-n-[2-[4-(hydroxymethyl)-n-methylanilino]-2-oxoethyl]-n-methyl-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)N(C)CC(=O)N(C)C1=CC=C(CO)C=C1 DHIQNDDDYDYAOK-VWNXMTODSA-N 0.000 claims 1
- URQLGFMFTYMWQJ-GGAORHGYSA-N (2s,4r)-n-benzyl-1-naphthalen-2-ylsulfonyl-4-sulfanyl-n-[2-(2h-tetrazol-5-yl)ethyl]pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1C[C@H](CN1S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)S)N(CC=1C=CC=CC=1)CCC1=NN=NN1 URQLGFMFTYMWQJ-GGAORHGYSA-N 0.000 claims 1
- RASBKWUKAAKWET-IRLDBZIGSA-N (2s,4r)-n-benzyl-n-methyl-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)N(C)CC1=CC=CC=C1 RASBKWUKAAKWET-IRLDBZIGSA-N 0.000 claims 1
- DZWFBSMOBOEIPW-MJGOQNOKSA-N (2s,4r)-n-cyclopropyl-1-naphthalen-2-ylsulfonyl-4-sulfanyl-n-[2-(2h-tetrazol-5-yl)ethyl]pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1C[C@H](CN1S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)S)N(C1CC1)CCC1=NN=NN1 DZWFBSMOBOEIPW-MJGOQNOKSA-N 0.000 claims 1
- HIFRPZYHLKDAGD-CTNGQTDRSA-N (2s,4r)-n-hexyl-n-methyl-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carboxamide Chemical compound CCCCCCN(C)C(=O)[C@@H]1C[C@@H](S)CN1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 HIFRPZYHLKDAGD-CTNGQTDRSA-N 0.000 claims 1
- UDISNMIDXZZFOX-IRLDBZIGSA-N (2s,4r)-n-methyl-1-naphthalen-2-ylsulfonyl-n-phenacyl-4-sulfanylpyrrolidine-2-carboxamide Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)N(C)CC(=O)C1=CC=CC=C1 UDISNMIDXZZFOX-IRLDBZIGSA-N 0.000 claims 1
- LNQKCRQYWZQGDY-CTNGQTDRSA-N (2s,4r)-n-methyl-n-(4-methyl-2-oxopentyl)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carboxamide Chemical compound CC(C)CC(=O)CN(C)C(=O)[C@@H]1C[C@@H](S)CN1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 LNQKCRQYWZQGDY-CTNGQTDRSA-N 0.000 claims 1
- BYTFMTJXNIWGRI-HKUYNNGSSA-N 1-[(2s,4s)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1C(=O)[C@H]1N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C[C@@H](S)C1 BYTFMTJXNIWGRI-HKUYNNGSSA-N 0.000 claims 1
- RLBCCMAOTQIXMG-QUCCMNQESA-N 2-[3-methylbutyl-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]amino]acetic acid Chemical compound CC(C)CCN(CC(O)=O)C(=O)[C@@H]1C[C@@H](S)CN1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 RLBCCMAOTQIXMG-QUCCMNQESA-N 0.000 claims 1
- BIWHMCTZQSBFTQ-GCJKJVERSA-N 2-[[2-[methyl-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]amino]acetyl]amino]benzoic acid Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)N(C)CC(=O)NC1=CC=CC=C1C(O)=O BIWHMCTZQSBFTQ-GCJKJVERSA-N 0.000 claims 1
- HSLOUYLTGMNCJP-GGAORHGYSA-N 3-[benzyl-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)N(CCC(=O)O)CC1=CC=CC=C1 HSLOUYLTGMNCJP-GGAORHGYSA-N 0.000 claims 1
- OMNHCFHMYDCIKF-AEFFLSMTSA-N 3-methyl-1-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidin-2-yl]butan-1-one Chemical compound CC(C)CC(=O)[C@@H]1C[C@@H](S)CN1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 OMNHCFHMYDCIKF-AEFFLSMTSA-N 0.000 claims 1
- VTHPWPGJXZCYHN-GGAORHGYSA-N 4-[methyl-[2-[methyl-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]amino]acetyl]amino]benzoic acid Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)N(C)CC(=O)N(C)C1=CC=C(C(O)=O)C=C1 VTHPWPGJXZCYHN-GGAORHGYSA-N 0.000 claims 1
- ZLYVUOYXJOQSCM-GMAHTHKFSA-N C1CC(C(=O)OCC)CCN1C(=O)[C@H]1N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C[C@@H](SC(C)=O)C1 Chemical compound C1CC(C(=O)OCC)CCN1C(=O)[C@H]1N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C[C@@H](SC(C)=O)C1 ZLYVUOYXJOQSCM-GMAHTHKFSA-N 0.000 claims 1
- 208000034189 Sclerosis Diseases 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 230000003143 atherosclerotic effect Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GZNYQFXHIHSTST-CVEARBPZSA-N butyl (2s,4r)-2-(3-phenylpropanoyl)-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CCCCOC(=O)N1C[C@H](S)C[C@H]1C(=O)CCC1=CC=CC=C1 GZNYQFXHIHSTST-CVEARBPZSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- SKYXSYWCKCZYBA-FPOVZHCZSA-N ethyl 1-[(2s,4s)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)[C@H]1N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C[C@@H](S)C1 SKYXSYWCKCZYBA-FPOVZHCZSA-N 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- XQPOFONTMJXZRQ-XXBNENTESA-N methyl 2-[[2-[methyl-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]amino]acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CN(C)C(=O)[C@H]1N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C[C@H](S)C1 XQPOFONTMJXZRQ-XXBNENTESA-N 0.000 claims 1
- APMDTOUBZRTXII-VWNXMTODSA-N methyl 4-[methyl-[2-[methyl-[(2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbonyl]amino]acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N(C)C(=O)CN(C)C(=O)[C@H]1N(S(=O)(=O)C=2C=C3C=CC=CC3=CC=2)C[C@H](S)C1 APMDTOUBZRTXII-VWNXMTODSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- XBDYTZCQNDHGJO-SJORKVTESA-N pentyl (2s,4r)-2-[benzyl(methyl)carbamoyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CCCCCOC(=O)N1C[C@H](S)C[C@H]1C(=O)N(C)CC1=CC=CC=C1 XBDYTZCQNDHGJO-SJORKVTESA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- LNGMYPHQOVNMRM-CABCVRRESA-N propan-2-yl (2s,4r)-2-[benzyl(methyl)carbamoyl]-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CC(C)OC(=O)N1C[C@H](S)C[C@H]1C(=O)N(C)CC1=CC=CC=C1 LNGMYPHQOVNMRM-CABCVRRESA-N 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00114947 | 2000-07-19 | ||
| PCT/EP2001/007950 WO2002006222A1 (en) | 2000-07-19 | 2001-07-10 | Pyrrolidine derivatives as inhibitors of endothelin-converting enzyme |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004504297A JP2004504297A (ja) | 2004-02-12 |
| JP2004504297A5 true JP2004504297A5 (enExample) | 2007-01-18 |
| JP4068452B2 JP4068452B2 (ja) | 2008-03-26 |
Family
ID=8169224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002512128A Expired - Fee Related JP4068452B2 (ja) | 2000-07-19 | 2001-07-10 | エンドセリン変換酵素阻害剤としてのピロリジン誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6541638B2 (enExample) |
| EP (1) | EP1303485A1 (enExample) |
| JP (1) | JP4068452B2 (enExample) |
| KR (1) | KR100568841B1 (enExample) |
| CN (1) | CN1620433A (enExample) |
| AR (1) | AR033984A1 (enExample) |
| AU (1) | AU2001270627A1 (enExample) |
| BR (1) | BR0112580A (enExample) |
| CA (1) | CA2414311C (enExample) |
| GT (1) | GT200100145A (enExample) |
| MX (1) | MXPA03000223A (enExample) |
| PA (1) | PA8522501A1 (enExample) |
| PE (1) | PE20020294A1 (enExample) |
| UY (1) | UY26847A1 (enExample) |
| WO (1) | WO2002006222A1 (enExample) |
| ZA (1) | ZA200300167B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA03000368A (es) * | 2000-07-19 | 2004-09-13 | Hoffmann La Roche | Derivados de pirrolidina como inhibidores de metalproteasa. |
| TWI312779B (enExample) * | 2000-12-28 | 2009-08-01 | Daiichi Seiyaku Co | |
| DE60336986D1 (de) | 2002-03-05 | 2011-06-16 | Sumitomo Chemical Co | Verfahren zur herstellung von biarylverbindungen |
| EP1613269B1 (en) | 2003-04-04 | 2015-02-25 | Incyte Corporation | Compositions, methods and kits relating to her-2 cleavage |
| AU2004231070B2 (en) | 2003-04-10 | 2008-02-14 | Amgen, Inc. | Bicyclic compounds having bradykinin receptors affinity and pharmaceutical compositions thereof |
| CA2522084A1 (en) | 2003-04-10 | 2004-10-28 | Amgen Inc. | Cyclic amine derivatives and their use in the treatment of inflammation-related disorders mediated by bradykinin |
| MXPA05013469A (es) | 2003-06-20 | 2006-03-09 | Amgen Inc | Derivados de piperazina y metodos de uso. |
| MXPA06000850A (es) | 2003-07-24 | 2006-03-30 | Daiichi Seiyaku Co | Compuesto de acido ciclohexancarboxilico. |
| CN1294120C (zh) * | 2003-10-21 | 2007-01-10 | 山东大学 | 吡咯烷类基质金属蛋白酶抑制剂及其应用 |
| US20100022568A1 (en) * | 2006-04-13 | 2010-01-28 | Actelion Pharmaceeuticals Ltd. | Endothelin receptor antagonists for early stage idiopathic pulmonary fibrosis |
| ES2350548B1 (es) * | 2009-06-25 | 2011-09-29 | Institut Univ. De Ciència I Tecnologia, S.A. | N-fenil-1-sulfonil-2-pirrolidinacarboxamidas para la identificacion de actividad biologica y farmacologica. |
| EP2730571A1 (en) * | 2012-11-12 | 2014-05-14 | Universitat De Barcelona | 1-[1-(benzoyl)-pyrrolidine-2-carbonyl]-pyrrolidine-2-carbonitrile derivatives |
| WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
| WO2019009317A1 (ja) * | 2017-07-05 | 2019-01-10 | 日産化学株式会社 | ベンジル化合物 |
| CN110078593A (zh) * | 2018-11-15 | 2019-08-02 | 南通正达农化有限公司 | 一种苹果蠹蛾性信息素的合成方法 |
| WO2025124698A1 (en) | 2023-12-12 | 2025-06-19 | Idorsia Pharmaceuticals Ltd | Aryl sulfone and sulfanone derivatives as orexin receptor modulators |
| WO2025132542A1 (en) | 2023-12-19 | 2025-06-26 | Idorsia Pharmaceuticals Ltd | Macrocyclic orexin agonists |
| CN119661387B (zh) * | 2024-12-18 | 2025-12-16 | 长沙普济生物科技股份有限公司 | 一种烷基胺与3-卤代丙酸酯合成N-烷基-β-氨基丙酸钠的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1283906C (en) * | 1983-05-09 | 1991-05-07 | Makoto Sunagawa | .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF |
| AU644008B2 (en) * | 1990-08-10 | 1993-12-02 | Sumitomo Pharmaceuticals Company, Limited | Beta-lactam compounds, and their production and use |
| JP3091297B2 (ja) * | 1992-01-10 | 2000-09-25 | 住友製薬株式会社 | ピロリジン誘導体およびその製造方法 |
| BR9712792A (pt) * | 1996-08-28 | 1999-12-14 | Procter & Gamble | Inibidores de metaloprotease bidentada. |
| DE69716449T2 (de) * | 1996-08-28 | 2003-08-07 | The Procter & Gamble Company, Cincinnati | Substituierte zyklische amine als metalloproteaseinhibitoren |
| CA2294341C (en) * | 1997-07-10 | 2007-09-25 | Merck & Co., Inc. | Crystalline forms of antibiotic side chain intermediates |
| YU66700A (sh) * | 1998-05-01 | 2003-01-31 | Kyoto Pharmaceutical Industries Ltd. | Derivati karbapenema, njihovo korišćenje i intermedijarna jedinjenja istih |
-
2001
- 2001-07-10 CA CA002414311A patent/CA2414311C/en not_active Expired - Fee Related
- 2001-07-10 BR BR0112580-0A patent/BR0112580A/pt not_active IP Right Cessation
- 2001-07-10 JP JP2002512128A patent/JP4068452B2/ja not_active Expired - Fee Related
- 2001-07-10 AU AU2001270627A patent/AU2001270627A1/en not_active Abandoned
- 2001-07-10 KR KR1020037000781A patent/KR100568841B1/ko not_active Expired - Fee Related
- 2001-07-10 EP EP01949485A patent/EP1303485A1/en not_active Withdrawn
- 2001-07-10 CN CNA018130232A patent/CN1620433A/zh active Pending
- 2001-07-10 MX MXPA03000223A patent/MXPA03000223A/es not_active Application Discontinuation
- 2001-07-10 WO PCT/EP2001/007950 patent/WO2002006222A1/en not_active Ceased
- 2001-07-16 PA PA20018522501A patent/PA8522501A1/es unknown
- 2001-07-16 PE PE2001000711A patent/PE20020294A1/es not_active Application Discontinuation
- 2001-07-17 UY UY26847A patent/UY26847A1/es not_active Application Discontinuation
- 2001-07-17 AR ARP010103416A patent/AR033984A1/es unknown
- 2001-07-17 US US09/907,135 patent/US6541638B2/en not_active Expired - Fee Related
- 2001-07-18 GT GT200100145A patent/GT200100145A/es unknown
-
2003
- 2003-01-07 ZA ZA200300167A patent/ZA200300167B/en unknown
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