FI113265B - Menetelmä uusien, verihiutaleiden aggregaatiota estävien 2,5-dioksoimidatsolidinyylijohdannaisten valmistamiseksi - Google Patents
Menetelmä uusien, verihiutaleiden aggregaatiota estävien 2,5-dioksoimidatsolidinyylijohdannaisten valmistamiseksi Download PDFInfo
- Publication number
- FI113265B FI113265B FI962043A FI962043A FI113265B FI 113265 B FI113265 B FI 113265B FI 962043 A FI962043 A FI 962043A FI 962043 A FI962043 A FI 962043A FI 113265 B FI113265 B FI 113265B
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- phenyl
- mmol
- dioxo
- imidazolidin
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- -1 2,5-dioxoimidazolidinyl Chemical class 0.000 title claims description 76
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 10
- 208000010110 spontaneous platelet aggregation Diseases 0.000 title claims description 9
- 230000002401 inhibitory effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000005074 adamantylmethyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000012634 fragment Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000003841 chloride salts Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 92
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- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
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- 239000000243 solution Substances 0.000 description 74
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- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 62
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- 229960000583 acetic acid Drugs 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000463 material Substances 0.000 description 39
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- 239000008346 aqueous phase Substances 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
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- 239000000725 suspension Substances 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 150000002334 glycols Chemical class 0.000 description 14
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 13
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 102100023038 WD and tetratricopeptide repeats protein 1 Human genes 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 229960005261 aspartic acid Drugs 0.000 description 11
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 10
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- 239000000126 substance Substances 0.000 description 9
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- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 7
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- XSOHXMFFSKTSIT-UHFFFAOYSA-N 1-adamantylmethanamine Chemical compound C1C(C2)CC3CC2CC1(CN)C3 XSOHXMFFSKTSIT-UHFFFAOYSA-N 0.000 description 5
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/021—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4338944A DE4338944A1 (de) | 1993-11-15 | 1993-11-15 | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE4338944 | 1993-11-15 | ||
| DE4427979A DE4427979A1 (de) | 1993-11-15 | 1994-08-08 | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE4427979 | 1994-08-08 | ||
| PCT/EP1994/003491 WO1995014008A1 (de) | 1993-11-15 | 1994-10-24 | Substituierte 5-ring-heterocyclen, ihre herstellung und ihre verwendung |
| EP9403491 | 1994-10-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI962043L FI962043L (fi) | 1996-05-14 |
| FI962043A0 FI962043A0 (fi) | 1996-05-14 |
| FI113265B true FI113265B (fi) | 2004-03-31 |
Family
ID=25931237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI962043A FI113265B (fi) | 1993-11-15 | 1996-05-14 | Menetelmä uusien, verihiutaleiden aggregaatiota estävien 2,5-dioksoimidatsolidinyylijohdannaisten valmistamiseksi |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US5981492A (cs) |
| EP (1) | EP0729460B1 (cs) |
| JP (1) | JP3813983B2 (cs) |
| KR (1) | KR100402192B1 (cs) |
| CN (1) | CN1069316C (cs) |
| AT (1) | ATE217615T1 (cs) |
| AU (1) | AU693811B2 (cs) |
| CA (1) | CA2169643A1 (cs) |
| CY (1) | CY2385B1 (cs) |
| CZ (1) | CZ292573B6 (cs) |
| DE (2) | DE4427979A1 (cs) |
| DK (1) | DK0729460T3 (cs) |
| ES (1) | ES2176261T3 (cs) |
| FI (1) | FI113265B (cs) |
| HU (1) | HU223806B1 (cs) |
| IL (1) | IL111622A (cs) |
| PL (1) | PL180906B1 (cs) |
| PT (1) | PT729460E (cs) |
| RU (1) | RU2151143C1 (cs) |
| SK (1) | SK284471B6 (cs) |
| TW (1) | TW326040B (cs) |
| WO (1) | WO1995014008A1 (cs) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4427979A1 (de) | 1993-11-15 | 1996-02-15 | Cassella Ag | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE19515177A1 (de) * | 1995-04-28 | 1996-10-31 | Cassella Ag | Hydantoinderivate als Zwischenprodukte für pharmazeutische Wirkstoffe |
| JP3895792B2 (ja) * | 1995-12-08 | 2007-03-22 | プロスケリア・エス・ア・エス | 骨形成促進剤 |
| ES2171768T3 (es) * | 1996-03-20 | 2002-09-16 | Hoechst Ag | Inhibidores de la resorcion osea y antagonistas de receptores de vitronectina. |
| DE19622489A1 (de) * | 1996-06-05 | 1997-12-11 | Hoechst Ag | Salze des 3-(2-(4-(4-(Amino-imino-methyl)-phenyl)-4- methyl-2,5-dioxo-imidazolidin-1-yl)-acetylamino)-3- phenyl-propionsäure-ethylesters |
| DE19624604A1 (de) * | 1996-06-20 | 1998-01-02 | Hoechst Ag | Verfahren zur Herstellung chiraler, nicht racemischer (4-Aryl-2,5-dioxoimidazolidin-1-yl)essigsäuren |
| DE19629816A1 (de) | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Cycloalkyl-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| DE19629817A1 (de) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | Neue Imino-Derivate als Inhibitoren der Knochenresorption und Vitronectinrezeptor-Antagonisten |
| DE19647381A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | Neue Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| KR100697959B1 (ko) * | 1996-11-15 | 2007-07-09 | 훽스트 게엠베하 | 백혈구부착의억제제및vla-4길항제로서의헤테로사이클 |
| DE19647380A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | 5-Ring-Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| PL323130A1 (en) | 1996-11-15 | 1998-05-25 | Hoechst Ag | Application of heterocyclic compounds in production of a pharmaceutic agent, novel heterocyclic compounds and pharmaceutic agent as such |
| DE19741235A1 (de) * | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19741873A1 (de) * | 1997-09-23 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue 5-Ring-Heterocyclen, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19751251A1 (de) | 1997-11-19 | 1999-05-20 | Hoechst Marion Roussel De Gmbh | Substituierte Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmezeutische Präparate |
| DE19821483A1 (de) * | 1998-05-14 | 1999-11-18 | Hoechst Marion Roussel De Gmbh | Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE19922462A1 (de) | 1999-05-17 | 2000-11-23 | Aventis Pharma Gmbh | Spiro-imidazolidinderivate, ihre Herstellung ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| US6624187B1 (en) * | 2000-06-12 | 2003-09-23 | Health Research, Inc. | Long wave length absorbing bacteriochlorin alkyl ether analogs |
| DE10111877A1 (de) * | 2001-03-10 | 2002-09-12 | Aventis Pharma Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| DE10137595A1 (de) | 2001-08-01 | 2003-02-13 | Aventis Pharma Gmbh | Neue Imidazolidinderivate, ihre Herstellung und ihre Verwendung |
| JP2007514742A (ja) * | 2003-12-18 | 2007-06-07 | アストラゼネカ アクチボラグ | トロンビンの阻害薬として有用な新規５，６−ジヒドロピリジン−２−オン化合物 |
| CN107383147A (zh) * | 2017-07-14 | 2017-11-24 | 广东食品药品职业学院 | 一种β‑谷甾醇与依帕司他偶联物及其制备方法和用途 |
| WO2019200202A1 (en) * | 2018-04-12 | 2019-10-17 | Morphic Therapeutic, Inc. | Antagonists of human integrin (alpha4)(beta7) |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| BR112022007284A2 (pt) | 2019-10-16 | 2022-07-05 | Morphic Therapeutic Inc | Inibição de integrina humana alpha-4 beta-7 |
| CN117800921B (zh) * | 2024-02-28 | 2024-06-11 | 南京市鸿舜医药科技有限公司 | 一种咪唑烷二酮类hdac抑制剂、制备方法及应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3300510A (en) * | 1964-03-06 | 1967-01-24 | American Home Prod | Hydantoins |
| DE2714655A1 (de) * | 1977-04-01 | 1978-10-05 | Bayer Ag | Verfahren zur herstellung von hydantoinen |
| EP0006352A1 (en) * | 1978-06-15 | 1980-01-09 | Beecham Group Plc | Hydantoins and thiohydantoins, process for their preparation and pharmaceutical compositions containing them |
| GB2032419B (en) * | 1978-09-05 | 1983-01-19 | Wellcome Found | Hydantoin prostaglandin analogues |
| CA2008116C (en) * | 1989-02-23 | 2001-11-20 | Thomas Weller | Glycine derivatives |
| DE4009506A1 (de) * | 1990-03-24 | 1991-09-26 | Hoechst Ag | Hydantoinderivate |
| WO1992019595A1 (en) * | 1991-05-07 | 1992-11-12 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| DE4126277A1 (de) * | 1991-08-08 | 1993-02-11 | Cassella Ag | Hydantoinderivate |
| DE4207254A1 (de) * | 1992-03-07 | 1993-09-09 | Cassella Ag | 4-oxo-2-thioxoimidazolidin-derivate |
| DE4213634A1 (de) * | 1992-04-24 | 1993-10-28 | Cassella Ag | 2,4-Dioxo-imidazolidin-Derivate |
| DE4224414A1 (de) * | 1992-07-24 | 1994-01-27 | Cassella Ag | Phenylimidazolidin-derivate, ihre Herstellung und ihre Verwendung |
| DE4301747A1 (de) * | 1993-01-23 | 1994-07-28 | Cassella Ag | Substituierte Aminoverbindungen, ihre Herstellung und ihre Verwendung |
| DE4308034A1 (de) | 1993-03-13 | 1994-09-15 | Cassella Ag | Neue Heterocyclen, ihre Herstellung und ihre Verwendung |
| DE4309867A1 (de) | 1993-03-26 | 1994-09-29 | Cassella Ag | Neue Harnstoffderivate, ihre Herstellung und Verwendung |
| DE4427979A1 (de) | 1993-11-15 | 1996-02-15 | Cassella Ag | Substituierte 5-Ring-Heterocyclen, ihre Herstellung und ihre Verwendung |
-
1994
- 1994-08-08 DE DE4427979A patent/DE4427979A1/de not_active Withdrawn
- 1994-10-24 WO PCT/EP1994/003491 patent/WO1995014008A1/de active IP Right Grant
- 1994-10-24 EP EP94930215A patent/EP0729460B1/de not_active Expired - Lifetime
- 1994-10-24 RU RU96113118/04A patent/RU2151143C1/ru not_active IP Right Cessation
- 1994-10-24 SK SK585-96A patent/SK284471B6/sk unknown
- 1994-10-24 PL PL94314306A patent/PL180906B1/pl not_active IP Right Cessation
- 1994-10-24 DK DK94930215T patent/DK0729460T3/da active
- 1994-10-24 DE DE59410120T patent/DE59410120D1/de not_active Expired - Lifetime
- 1994-10-24 CA CA002169643A patent/CA2169643A1/en not_active Abandoned
- 1994-10-24 AT AT94930215T patent/ATE217615T1/de not_active IP Right Cessation
- 1994-10-24 CN CN94194043A patent/CN1069316C/zh not_active Expired - Fee Related
- 1994-10-24 PT PT94930215T patent/PT729460E/pt unknown
- 1994-10-24 AU AU79397/94A patent/AU693811B2/en not_active Ceased
- 1994-10-24 ES ES94930215T patent/ES2176261T3/es not_active Expired - Lifetime
- 1994-10-24 CZ CZ19961162A patent/CZ292573B6/cs not_active IP Right Cessation
- 1994-10-24 HU HU9601300A patent/HU223806B1/hu not_active IP Right Cessation
- 1994-10-24 KR KR1019960702512A patent/KR100402192B1/ko not_active Expired - Fee Related
- 1994-10-24 US US08/640,895 patent/US5981492A/en not_active Expired - Lifetime
- 1994-10-24 JP JP51417695A patent/JP3813983B2/ja not_active Expired - Fee Related
- 1994-11-14 IL IL11162294A patent/IL111622A/xx not_active IP Right Cessation
- 1994-12-13 TW TW083111713A patent/TW326040B/zh active
-
1996
- 1996-05-14 FI FI962043A patent/FI113265B/fi not_active IP Right Cessation
-
1999
- 1999-07-28 US US09/362,363 patent/US6191282B1/en not_active Expired - Fee Related
-
2003
- 2003-11-11 CY CY0300083A patent/CY2385B1/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |