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 (https=) | 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 (https=) |
| EP (1) | EP1303485A1 (https=) |
| JP (1) | JP4068452B2 (https=) |
| KR (1) | KR100568841B1 (https=) |
| CN (1) | CN1620433A (https=) |
| AR (1) | AR033984A1 (https=) |
| AU (1) | AU2001270627A1 (https=) |
| BR (1) | BR0112580A (https=) |
| CA (1) | CA2414311C (https=) |
| GT (1) | GT200100145A (https=) |
| MX (1) | MXPA03000223A (https=) |
| PA (1) | PA8522501A1 (https=) |
| PE (1) | PE20020294A1 (https=) |
| UY (1) | UY26847A1 (https=) |
| WO (1) | WO2002006222A1 (https=) |
| ZA (1) | ZA200300167B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3983663B2 (ja) * | 2000-07-19 | 2007-09-26 | エフ．ホフマン−ラ ロシュ アーゲー | メタロプロテアーゼインヒビターとしてのピロリジン誘導体 |
| US7157487B2 (en) | 2000-12-28 | 2007-01-02 | Daiichi Pharmaceutical Co., Ltd. | Vla-4 inhibitors |
| EP2161254B1 (en) | 2002-03-05 | 2014-08-13 | Sumitomo Chemical Company, Limited | Intermediate for preparing a biaryl compound |
| US8088737B2 (en) | 2003-04-04 | 2012-01-03 | Incyte Corporation | Compositions, methods and kits relating to Her-2 cleavage |
| JP2006522835A (ja) | 2003-04-10 | 2006-10-05 | アムジェン インコーポレイテッド | 環状アミン誘導体およびブラジキニンによって媒介される炎症関連障害の処置におけるそれらの使用 |
| AU2004231070B2 (en) | 2003-04-10 | 2008-02-14 | Amgen, Inc. | Bicyclic compounds having bradykinin receptors affinity and pharmaceutical compositions thereof |
| US7393852B2 (en) | 2003-06-20 | 2008-07-01 | Amgen Inc. | Piperazine derivatives and methods of use |
| EP1650205B1 (en) | 2003-07-24 | 2012-04-25 | Daiichi Sankyo Company, Limited | Cyclohexanecarboxylic acid compound |
| 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 |
| WO2007119214A2 (en) * | 2006-04-13 | 2007-10-25 | Actelion Pharmaceuticals 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 |
| JP7163916B2 (ja) * | 2017-07-05 | 2022-11-01 | 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 |
| TW202542165A (zh) | 2023-12-19 | 2025-11-01 | 瑞士商愛杜西亞製藥有限公司 | 大環食慾素激動劑 |
| 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 |
| RU2221782C2 (ru) * | 1996-08-28 | 2004-01-20 | Дзе Проктер Энд Гэмбл Компани | Замещенные циклические аминовые ингибиторы металлопротеаз |
| BR9712792A (pt) * | 1996-08-28 | 1999-12-14 | Procter & Gamble | Inibidores de metaloprotease bidentada. |
| AU736136B2 (en) * | 1997-07-10 | 2001-07-26 | Merck Sharp & Dohme Corp. | Crystalline forms of antibiotic side chain intermediates |
| TR200003199T2 (tr) * | 1998-05-01 | 2001-03-21 | Kyoto Pharmaceutical Industries, Ltd. | Karbapenem türevleri, bunların kullanımı ve ara birleşiği |
-
2001
- 2001-07-10 MX MXPA03000223A patent/MXPA03000223A/es not_active Application Discontinuation
- 2001-07-10 JP JP2002512128A patent/JP4068452B2/ja not_active Expired - Fee Related
- 2001-07-10 WO PCT/EP2001/007950 patent/WO2002006222A1/en not_active Ceased
- 2001-07-10 AU AU2001270627A patent/AU2001270627A1/en not_active Abandoned
- 2001-07-10 EP EP01949485A patent/EP1303485A1/en not_active Withdrawn
- 2001-07-10 KR KR1020037000781A patent/KR100568841B1/ko not_active Expired - Fee Related
- 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 CN CNA018130232A patent/CN1620433A/zh active Pending
- 2001-07-16 PE PE2001000711A patent/PE20020294A1/es not_active Application Discontinuation
- 2001-07-16 PA PA20018522501A patent/PA8522501A1/es unknown
- 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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