CA2465399A1 - Alkane diol derivatives as therapeutic agents for the treatment of bone conditions - Google Patents
Alkane diol derivatives as therapeutic agents for the treatment of bone conditions Download PDFInfo
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- CA2465399A1 CA2465399A1 CA002465399A CA2465399A CA2465399A1 CA 2465399 A1 CA2465399 A1 CA 2465399A1 CA 002465399 A CA002465399 A CA 002465399A CA 2465399 A CA2465399 A CA 2465399A CA 2465399 A1 CA2465399 A1 CA 2465399A1
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- -1 Alkane diol Chemical class 0.000 title claims abstract description 191
- 210000000988 bone and bone Anatomy 0.000 title claims description 90
- 238000011282 treatment Methods 0.000 title claims description 59
- 239000003814 drug Substances 0.000 title claims description 32
- 229940124597 therapeutic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 415
- 210000002997 osteoclast Anatomy 0.000 claims abstract description 150
- 150000002148 esters Chemical class 0.000 claims abstract description 106
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 230000000694 effects Effects 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 44
- 208000006386 Bone Resorption Diseases 0.000 claims abstract description 34
- 230000024279 bone resorption Effects 0.000 claims abstract description 33
- 239000000651 prodrug Substances 0.000 claims abstract description 26
- 229940002612 prodrug Drugs 0.000 claims abstract description 26
- 239000012453 solvate Substances 0.000 claims abstract description 25
- 150000001408 amides Chemical class 0.000 claims abstract description 23
- 230000004083 survival effect Effects 0.000 claims abstract description 22
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 20
- 230000001404 mediated effect Effects 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 16
- 150000002170 ethers Chemical class 0.000 claims abstract description 16
- 206010061218 Inflammation Diseases 0.000 claims abstract description 15
- 230000004054 inflammatory process Effects 0.000 claims abstract description 15
- 208000020084 Bone disease Diseases 0.000 claims abstract description 13
- 230000004913 activation Effects 0.000 claims abstract description 13
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 13
- 208000016738 bone Paget disease Diseases 0.000 claims abstract description 12
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- 238000001727 in vivo Methods 0.000 claims abstract description 11
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- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims abstract 9
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- 238000000034 method Methods 0.000 claims description 172
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 65
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- 125000001424 substituent group Chemical group 0.000 claims description 31
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 29
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
- NEZHKHMZNSFKGS-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-(methylamino)butan-1-one Chemical compound CCC(NC)C(=O)C1=CC=C(F)C=C1 NEZHKHMZNSFKGS-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
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- 125000000623 heterocyclic group Chemical group 0.000 description 21
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- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 19
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
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- 210000002435 tendon Anatomy 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- KHVCOYGKHDJPBZ-WDCZJNDASA-N tetrahydrooxazine Chemical compound OC[C@H]1ONC[C@@H](O)[C@@H]1O KHVCOYGKHDJPBZ-WDCZJNDASA-N 0.000 description 1
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- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- BQAJJINKFRRSFO-UHFFFAOYSA-N thiolane Chemical compound C1CCSC1.C1CCSC1 BQAJJINKFRRSFO-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- WEMNATFLVGEPEW-UHFFFAOYSA-N thiophene Chemical compound C=1C=CSC=1.C=1C=CSC=1 WEMNATFLVGEPEW-UHFFFAOYSA-N 0.000 description 1
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- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- 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]
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0126157.7A GB0126157D0 (en) | 2001-10-31 | 2001-10-31 | Therapeutic compounds |
| GB0126157.7 | 2001-10-31 | ||
| PCT/GB2002/004933 WO2003037321A1 (en) | 2001-10-31 | 2002-10-31 | Alkane diol derivatives as therapeutic agents for the treatment of bone conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2465399A1 true CA2465399A1 (en) | 2003-05-08 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002465399A Abandoned CA2465399A1 (en) | 2001-10-31 | 2002-10-31 | Alkane diol derivatives as therapeutic agents for the treatment of bone conditions |
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|---|---|
| US (1) | US7745424B2 (enExample) |
| EP (1) | EP1441716B1 (enExample) |
| JP (1) | JP2005511556A (enExample) |
| KR (1) | KR20050042044A (enExample) |
| AT (1) | ATE327748T1 (enExample) |
| CA (1) | CA2465399A1 (enExample) |
| DE (1) | DE60211935T2 (enExample) |
| GB (1) | GB0126157D0 (enExample) |
| WO (1) | WO2003037321A1 (enExample) |
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| US20060177416A1 (en) | 2003-10-14 | 2006-08-10 | Medivas, Llc | Polymer particle delivery compositions and methods of use |
| US20060286064A1 (en) * | 2000-08-30 | 2006-12-21 | Medivas, Llc | Therapeutic polymers and methods |
| ATE380025T1 (de) | 2003-05-07 | 2007-12-15 | Univ Aberdeen | Ketone und reduzierte ketone als therapeutische mittel zur behandlung von knochenerkrankungen |
| US20060188469A1 (en) * | 2003-10-14 | 2006-08-24 | Medivas, Llc | Vaccine delivery compositions and methods of use |
| KR20060048138A (ko) | 2004-05-28 | 2006-05-18 | 가부시키가이샤 닛폰 쇼쿠바이 | 불소 함유 화합물 |
| GB0412553D0 (en) | 2004-06-04 | 2004-07-07 | Univ Aberdeen | Therapeutic agents for the treatment of bone conditions |
| US20070053984A1 (en) * | 2005-03-03 | 2007-03-08 | Monique Spann-Wade | Topical gels compositions |
| JP5178520B2 (ja) | 2005-09-22 | 2013-04-10 | メディバス エルエルシー | 固体ポリマー送達組成物およびその使用法 |
| EP1926780B1 (en) | 2005-09-22 | 2013-08-14 | Medivas, LLC | Bis-( -amino)-diol-diester-containing poly(ester amide) and poly(ester urethane) compositions and methods of use |
| US20080317684A1 (en) * | 2006-09-06 | 2008-12-25 | Isw Group, Inc. | Topical Compositions |
| GB0705400D0 (en) * | 2007-03-21 | 2007-05-02 | Univ Aberdeen | Therapeutic compounds andm their use |
| GB0817207D0 (en) | 2008-09-19 | 2008-10-29 | Pimco 2664 Ltd | therapeutic apsac compounds and their use |
| GB0817208D0 (en) | 2008-09-19 | 2008-10-29 | Pimco 2664 Ltd | Therapeutic apsap compounds and their use |
| WO2010036973A1 (en) * | 2008-09-25 | 2010-04-01 | Comgenrx, Inc. | Treatment of hyperproliferative disorders using cardiac glycosides |
| EP3159368B1 (en) | 2011-06-23 | 2024-07-24 | DSM IP Assets B.V. | New biodegradable polyesteramide copolymers for drug delivery |
| US9873765B2 (en) | 2011-06-23 | 2018-01-23 | Dsm Ip Assets, B.V. | Biodegradable polyesteramide copolymers for drug delivery |
| WO2013010400A1 (zh) * | 2011-07-21 | 2013-01-24 | Hou Wenge | 一种基于布洛芬的化合物及其制备方法和应用及药物制剂 |
| WO2014039042A1 (en) | 2012-09-06 | 2014-03-13 | Northeastern University | Novel cannabinergic compounds and uses thereof |
| US11964956B2 (en) | 2012-09-06 | 2024-04-23 | Northeastern University | Cannabinergic compounds and uses thereof |
| WO2014134127A1 (en) | 2013-02-26 | 2014-09-04 | Northeastern University | Cannabinergic nitrate esters and related analogs |
| EP2818531B1 (en) * | 2013-06-25 | 2017-07-26 | Merck Patent GmbH | Polymerisable compounds and the use thereof in liquid-crystal displays |
| GB201311361D0 (en) | 2013-06-26 | 2013-08-14 | Pimco 2664 Ltd | Compounds and their therapeutic use |
| CA2970578C (en) | 2014-12-17 | 2024-01-02 | Pimco 2664 Limited | N-(4-hydroxy-4-methyl-cyclohexyl)-4-phenyl-benzenesulfonamide and n-(4-hydroxy-4-methyl-cyclohexyl)-4-(2-pyridyl)-benzenesulfonamide compounds and their therapeutic use |
| AU2015366355B2 (en) | 2014-12-18 | 2020-05-28 | Dsm Ip Assets B.V. | Drug delivery system for delivery of acid sensitive drugs |
| CN113402386B (zh) * | 2021-05-28 | 2024-05-03 | 武汉亿科德精细化工有限公司 | 一种新戊二醇二苯甲酸酯的合成方法 |
| WO2024083934A1 (en) | 2022-10-19 | 2024-04-25 | Basf Se | Method for preparing 1,4-butanediol diesters |
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| GB663072A (en) | 1947-05-24 | 1951-12-19 | British Celanese | Improvements relating to compositions comprising organic thermoplastic substances |
| GB661185A (en) | 1947-11-24 | 1951-11-21 | Sterling Drug Inc | Improvements in or relating to the production of alkoxyalkyl esters of iodobenzoic acids |
| GB716877A (en) | 1951-07-25 | 1954-10-13 | British Celanese | Improvements in polyesters and their intermediates |
| GB774180A (en) | 1953-11-18 | 1957-05-08 | Cecil Reginald Burch | Grading or separation of solid materials in liquid suspension |
| GB774635A (en) | 1954-06-29 | 1957-05-15 | Thomae Gmbh Dr K | New benzoic acid derivatives, and processes for their preparation |
| JPS4326316Y1 (enExample) | 1964-11-21 | 1968-11-01 | ||
| CH496647A (de) | 1967-12-15 | 1970-09-30 | Hoechst Ag | Verfahren zur Herstellung von Terephthalsäure-(B-hydroxy-äthyl)-estern |
| US3689535A (en) | 1968-09-26 | 1972-09-05 | John Kollar | Process for preparing ethylene glycol esters |
| US3715389A (en) | 1971-03-01 | 1973-02-06 | Halcon International Inc | Process for preparing glycol esters from olefinically unsaturated compounds |
| DE2602030C2 (de) | 1976-01-21 | 1983-12-01 | Henkel KGaA, 4000 Düsseldorf | Diphosphonoalkancarbonsäuren und Verfahren zu deren Herstellung |
| JP2748005B2 (ja) | 1988-10-13 | 1998-05-06 | 旭電化工業株式会社 | 光学活性ビフェニル化合物および該化合物含有液晶組成物 |
| IT1256450B (it) * | 1992-11-26 | 1995-12-05 | Soldato Piero Del | Esteri nitrici con attivita' farmacologica e procedimento per la loro preparazione |
| US5374707A (en) * | 1993-02-18 | 1994-12-20 | Monsanto Company | Hydroxy ethyl bibenzoate |
| JP3538444B2 (ja) * | 1993-09-30 | 2004-06-14 | 株式会社三光開発科学研究所 | ジヒドロキシ化合物およびその製造方法 |
| US6124474A (en) | 1999-12-21 | 2000-09-26 | Abbott Laboratories | Synthesis of chiral 2-azetidinemethanol compounds |
| JP4326316B2 (ja) | 2003-12-09 | 2009-09-02 | 日産自動車株式会社 | 車両のトラクションコントロール装置 |
-
2001
- 2001-10-31 GB GBGB0126157.7A patent/GB0126157D0/en not_active Ceased
-
2002
- 2002-10-31 CA CA002465399A patent/CA2465399A1/en not_active Abandoned
- 2002-10-31 US US10/494,327 patent/US7745424B2/en not_active Expired - Lifetime
- 2002-10-31 WO PCT/GB2002/004933 patent/WO2003037321A1/en not_active Ceased
- 2002-10-31 DE DE60211935T patent/DE60211935T2/de not_active Expired - Lifetime
- 2002-10-31 EP EP02777456A patent/EP1441716B1/en not_active Expired - Lifetime
- 2002-10-31 AT AT02777456T patent/ATE327748T1/de not_active IP Right Cessation
- 2002-10-31 KR KR1020047006591A patent/KR20050042044A/ko not_active Withdrawn
- 2002-10-31 JP JP2003539665A patent/JP2005511556A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60211935D1 (de) | 2006-07-06 |
| ATE327748T1 (de) | 2006-06-15 |
| WO2003037321A1 (en) | 2003-05-08 |
| EP1441716B1 (en) | 2006-05-31 |
| KR20050042044A (ko) | 2005-05-04 |
| JP2005511556A (ja) | 2005-04-28 |
| EP1441716A1 (en) | 2004-08-04 |
| US7745424B2 (en) | 2010-06-29 |
| DE60211935T2 (de) | 2007-01-11 |
| US20040254151A1 (en) | 2004-12-16 |
| GB0126157D0 (en) | 2002-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |