ES2310772T3 - Prolinilarilacetamidas. - Google Patents
Prolinilarilacetamidas. Download PDFInfo
- Publication number
- ES2310772T3 ES2310772T3 ES04820404T ES04820404T ES2310772T3 ES 2310772 T3 ES2310772 T3 ES 2310772T3 ES 04820404 T ES04820404 T ES 04820404T ES 04820404 T ES04820404 T ES 04820404T ES 2310772 T3 ES2310772 T3 ES 2310772T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- methyl
- amido
- amide
- hydroxy
- 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.)
- Expired - Lifetime
Links
- HHDQVBSXYDRQGD-QWWZWVQMSA-N (2r,4r)-4-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound O[C@@H]1C[C@H](C(O)=O)N(C(O)=O)C1 HHDQVBSXYDRQGD-QWWZWVQMSA-N 0.000 claims abstract description 109
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 107
- 239000002253 acid Substances 0.000 claims abstract description 92
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- -1 N-butyl-amino Chemical group 0.000 claims abstract description 69
- 150000003839 salts Chemical class 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 239000012453 solvate Substances 0.000 claims abstract description 19
- HIVWIEDJMNQQRT-UHFFFAOYSA-N n-(4-aminophenyl)-2-methoxy-n-methylacetamide Chemical compound COCC(=O)N(C)C1=CC=C(N)C=C1 HIVWIEDJMNQQRT-UHFFFAOYSA-N 0.000 claims abstract description 8
- FXTJCYDXMWCGAE-UHFFFAOYSA-N n-(4-aminophenyl)-2-(dimethylamino)-n-methylacetamide Chemical compound CN(C)CC(=O)N(C)C1=CC=C(N)C=C1 FXTJCYDXMWCGAE-UHFFFAOYSA-N 0.000 claims abstract description 7
- QEIHSYGISQYKFL-UHFFFAOYSA-N n-(4-aminophenyl)-2-chloro-n-methylacetamide Chemical compound ClCC(=O)N(C)C1=CC=C(N)C=C1 QEIHSYGISQYKFL-UHFFFAOYSA-N 0.000 claims abstract description 7
- XJDZERKGXWDYKG-UHFFFAOYSA-N CCNCC(N(C)C(C=C1)=CC=C1N)=O Chemical compound CCNCC(N(C)C(C=C1)=CC=C1N)=O XJDZERKGXWDYKG-UHFFFAOYSA-N 0.000 claims abstract description 4
- QKFJNGKSEAXNQP-UHFFFAOYSA-N N-(4-aminophenyl)-2-(cyclohexylamino)-N-methylacetamide Chemical compound CN(C1=CC=C(C=C1)N)C(=O)CNC2CCCCC2 QKFJNGKSEAXNQP-UHFFFAOYSA-N 0.000 claims abstract description 4
- GEDKUVJVXNOQHG-UHFFFAOYSA-N N-(4-aminophenyl)-2-(cyclopropylmethylamino)-N-methylacetamide Chemical compound CN(C1=CC=C(C=C1)N)C(=O)CNCC2CC2 GEDKUVJVXNOQHG-UHFFFAOYSA-N 0.000 claims abstract description 4
- LPZRAAFOJSCDKI-UHFFFAOYSA-N N-(4-aminophenyl)-2-butoxy-N-methylacetamide Chemical compound CCCCOCC(=O)N(C)C1=CC=C(N)C=C1 LPZRAAFOJSCDKI-UHFFFAOYSA-N 0.000 claims abstract description 4
- KMKIXWMTCOVOOD-UHFFFAOYSA-N N-(4-aminophenyl)-N-methyl-2-(methylamino)acetamide Chemical compound CNCC(=O)N(C)C1=CC=C(C=C1)N KMKIXWMTCOVOOD-UHFFFAOYSA-N 0.000 claims abstract description 4
- VBRAHAVGFJYINX-UHFFFAOYSA-N N-(4-aminophenyl)-N-methyl-2-(propan-2-ylamino)acetamide Chemical compound CC(C)NCC(=O)N(C)C1=CC=C(C=C1)N VBRAHAVGFJYINX-UHFFFAOYSA-N 0.000 claims abstract description 4
- MATIVMNAYVKWJE-UHFFFAOYSA-N N-(4-aminophenyl)-N-methyl-2-propoxyacetamide Chemical compound CCCOCC(=O)N(C)C1=CC=C(N)C=C1 MATIVMNAYVKWJE-UHFFFAOYSA-N 0.000 claims abstract description 4
- QUGWUQDXDFDIIM-UHFFFAOYSA-N N-(6-aminopyridin-3-yl)-2-(dimethylamino)-N-methylacetamide Chemical compound CN(C)CC(=O)N(C)C1=CN=C(C=C1)N QUGWUQDXDFDIIM-UHFFFAOYSA-N 0.000 claims abstract description 4
- KHCBNRYAAGMYRW-UHFFFAOYSA-N N-(6-aminopyridin-3-yl)-2-methoxy-N-methylacetamide Chemical compound CN(C1=CN=C(C=C1)N)C(=O)COC KHCBNRYAAGMYRW-UHFFFAOYSA-N 0.000 claims abstract description 4
- IRXSLDSGVBCBSS-UHFFFAOYSA-N n-(4-aminophenyl)-2-(diethylamino)-n-methylacetamide Chemical compound CCN(CC)CC(=O)N(C)C1=CC=C(N)C=C1 IRXSLDSGVBCBSS-UHFFFAOYSA-N 0.000 claims abstract description 4
- XFCZCIMGBKXODO-UHFFFAOYSA-N n-(4-aminophenyl)-2-ethoxy-n-methylacetamide Chemical compound CCOCC(=O)N(C)C1=CC=C(N)C=C1 XFCZCIMGBKXODO-UHFFFAOYSA-N 0.000 claims abstract description 4
- SLCRJADUBQJEOJ-UHFFFAOYSA-N n-(4-aminophenyl)-2-hydroxy-n-methylacetamide Chemical compound OCC(=O)N(C)C1=CC=C(N)C=C1 SLCRJADUBQJEOJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 18
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- 208000019695 Migraine disease Diseases 0.000 claims description 5
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- 238000004519 manufacturing process Methods 0.000 claims description 4
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- WPVZTXPFONVQJF-UHFFFAOYSA-N 4-n-methyl-4-n-(2-morpholin-4-ylethyl)benzene-1,4-diamine Chemical compound C=1C=C(N)C=CC=1N(C)CCN1CCOCC1 WPVZTXPFONVQJF-UHFFFAOYSA-N 0.000 claims description 3
- XCHINKOFTKMLHS-UHFFFAOYSA-N N-(4-aminophenyl)-2-(cyclopentylamino)-N-methylacetamide Chemical compound CN(C1=CC=C(C=C1)N)C(=O)CNC2CCCC2 XCHINKOFTKMLHS-UHFFFAOYSA-N 0.000 claims description 3
- CYHGSZJHRCVXCB-UHFFFAOYSA-N N-(4-aminophenyl)-2-(tert-butylamino)-N-methylacetamide Chemical compound CC(C)(C)NCC(=O)N(C)C1=CC=C(C=C1)N CYHGSZJHRCVXCB-UHFFFAOYSA-N 0.000 claims description 3
- MKIZQIPAEYHENT-UHFFFAOYSA-N [2-(4-amino-N-methylanilino)-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)N(C)C1=CC=C(C=C1)N MKIZQIPAEYHENT-UHFFFAOYSA-N 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 229940126534 drug product Drugs 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- HGZIVFJSHCCKJL-UHFFFAOYSA-N N-(4-aminophenyl)-2-(4-hydroxypiperidin-1-yl)-N-methylacetamide Chemical compound C=1C=C(N)C=CC=1N(C)C(=O)CN1CCC(O)CC1 HGZIVFJSHCCKJL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 235000002639 sodium chloride Nutrition 0.000 description 43
- 239000000047 product Substances 0.000 description 41
- 239000002585 base Substances 0.000 description 15
- 108010074860 Factor Xa Proteins 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000008194 pharmaceutical composition Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000003826 tablet Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 108090000190 Thrombin Proteins 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229960004072 thrombin Drugs 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 108010054265 Factor VIIa Proteins 0.000 description 7
- 239000003146 anticoagulant agent Substances 0.000 description 7
- 239000006071 cream Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
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- 239000002775 capsule Substances 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
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- 108010048049 Factor IXa Proteins 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10358814 | 2003-12-16 | ||
| DE10358814A DE10358814A1 (de) | 2003-12-16 | 2003-12-16 | Prolinylarylacetamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2310772T3 true ES2310772T3 (es) | 2009-01-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04820404T Expired - Lifetime ES2310772T3 (es) | 2003-12-16 | 2004-11-26 | Prolinilarilacetamidas. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7732481B2 (https=) |
| EP (1) | EP1697318B1 (https=) |
| JP (1) | JP4800969B2 (https=) |
| KR (1) | KR20060113729A (https=) |
| CN (1) | CN1894210A (https=) |
| AR (1) | AR046765A1 (https=) |
| AT (1) | ATE406350T1 (https=) |
| AU (1) | AU2004299197B2 (https=) |
| BR (1) | BRPI0417630A (https=) |
| CA (1) | CA2549589A1 (https=) |
| DE (2) | DE10358814A1 (https=) |
| ES (1) | ES2310772T3 (https=) |
| MX (1) | MXPA06006740A (https=) |
| RU (1) | RU2006125509A (https=) |
| WO (1) | WO2005058817A1 (https=) |
| ZA (1) | ZA200605841B (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1818330A1 (de) | 2006-02-14 | 2007-08-15 | Boehringer Ingelheim Pharma GmbH & Co.KG | Substituierte Prolinamide, deren Herstellung und deren Verwendung als Arzneimittel |
| MY146623A (en) | 2006-05-16 | 2012-09-14 | Boehringer Ingelheim Int | Substituted prolinamides, manufacturing, and the use thereof as medicaments |
| WO2009000878A1 (en) * | 2007-06-28 | 2008-12-31 | Novartis Ag | Kallikrein 7 modulators |
| WO2011027888A1 (ja) * | 2009-09-07 | 2011-03-10 | 大日本住友製薬株式会社 | ジアミド－フェニル誘導体、またはその薬学的に許容される塩 |
| CN109761957B (zh) * | 2019-01-18 | 2020-05-19 | 西安交通大学 | 一种含有羟脯氨酸的化合物及其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7030141B2 (en) | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| BRPI0408444A (pt) * | 2003-04-03 | 2006-04-04 | Merck Patent Gmbh | derivados de 1-n-(fenil)-2-n-(fenil) pirazolidina-1,2-dicarboxamida como inibidores de fator xa de coagulação para o tratamento de trombose |
| PL377633A1 (pl) * | 2003-04-03 | 2006-02-06 | Merck Patent Gmbh | Związki karbonylowe |
| DE102004014945A1 (de) * | 2004-03-26 | 2005-10-13 | Merck Patent Gmbh | Prolinylderivate |
-
2003
- 2003-12-16 DE DE10358814A patent/DE10358814A1/de not_active Withdrawn
-
2004
- 2004-11-26 AU AU2004299197A patent/AU2004299197B2/en not_active Ceased
- 2004-11-26 RU RU2006125509/04A patent/RU2006125509A/ru not_active Application Discontinuation
- 2004-11-26 US US10/583,094 patent/US7732481B2/en not_active Expired - Fee Related
- 2004-11-26 AT AT04820404T patent/ATE406350T1/de not_active IP Right Cessation
- 2004-11-26 JP JP2006544256A patent/JP4800969B2/ja not_active Expired - Fee Related
- 2004-11-26 MX MXPA06006740A patent/MXPA06006740A/es not_active Application Discontinuation
- 2004-11-26 KR KR1020067011704A patent/KR20060113729A/ko not_active Withdrawn
- 2004-11-26 WO PCT/EP2004/013509 patent/WO2005058817A1/de not_active Ceased
- 2004-11-26 CN CNA2004800376989A patent/CN1894210A/zh active Pending
- 2004-11-26 CA CA002549589A patent/CA2549589A1/en not_active Abandoned
- 2004-11-26 BR BRPI0417630-8A patent/BRPI0417630A/pt not_active Application Discontinuation
- 2004-11-26 ES ES04820404T patent/ES2310772T3/es not_active Expired - Lifetime
- 2004-11-26 DE DE502004007959T patent/DE502004007959D1/de not_active Expired - Lifetime
- 2004-11-26 EP EP04820404A patent/EP1697318B1/de not_active Expired - Lifetime
- 2004-12-15 AR ARP040104656A patent/AR046765A1/es unknown
-
2006
- 2006-07-14 ZA ZA200605841A patent/ZA200605841B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20060113729A (ko) | 2006-11-02 |
| DE502004007959D1 (de) | 2008-10-09 |
| ZA200605841B (en) | 2007-10-31 |
| US7732481B2 (en) | 2010-06-08 |
| DE10358814A1 (de) | 2005-07-21 |
| JP4800969B2 (ja) | 2011-10-26 |
| CN1894210A (zh) | 2007-01-10 |
| AU2004299197B2 (en) | 2010-08-05 |
| EP1697318B1 (de) | 2008-08-27 |
| MXPA06006740A (es) | 2006-08-18 |
| US20070185189A1 (en) | 2007-08-09 |
| WO2005058817A1 (de) | 2005-06-30 |
| ATE406350T1 (de) | 2008-09-15 |
| JP2007513988A (ja) | 2007-05-31 |
| EP1697318A1 (de) | 2006-09-06 |
| AR046765A1 (es) | 2005-12-21 |
| RU2006125509A (ru) | 2008-01-27 |
| CA2549589A1 (en) | 2005-06-30 |
| BRPI0417630A (pt) | 2007-03-27 |
| AU2004299197A1 (en) | 2005-06-30 |
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