JP3280021B2 - 骨吸収を阻害する化合物及び組成物 - Google Patents
骨吸収を阻害する化合物及び組成物Info
- Publication number
- JP3280021B2 JP3280021B2 JP50160992A JP50160992A JP3280021B2 JP 3280021 B2 JP3280021 B2 JP 3280021B2 JP 50160992 A JP50160992 A JP 50160992A JP 50160992 A JP50160992 A JP 50160992A JP 3280021 B2 JP3280021 B2 JP 3280021B2
- Authority
- JP
- Japan
- Prior art keywords
- pthrp
- amino acid
- bone resorption
- bone
- hydrogen
- 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
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- 230000024279 bone resorption Effects 0.000 title claims abstract description 62
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- 102000043299 Parathyroid hormone-related Human genes 0.000 claims abstract description 174
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 7
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- 108700020797 Parathyroid Hormone-Related Proteins 0.000 claims description 63
- 230000000694 effects Effects 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
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- 125000006239 protecting group Chemical group 0.000 claims description 11
- 238000006467 substitution reaction Methods 0.000 claims description 11
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- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 8
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- 239000001963 growth medium Substances 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 108010025306 histidylleucine Proteins 0.000 description 1
- 230000009097 homeostatic mechanism Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000002601 intratumoral effect Effects 0.000 description 1
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 1
- JDNTWHVOXJZDSN-UHFFFAOYSA-N iodoacetic acid Chemical compound OC(=O)CI JDNTWHVOXJZDSN-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 1
- NEGQCMNHXHSFGU-UHFFFAOYSA-N methyl pyridine-2-carboximidate Chemical compound COC(=N)C1=CC=CC=N1 NEGQCMNHXHSFGU-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 210000005088 multinucleated cell Anatomy 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- SCIFESDRCALIIM-UHFFFAOYSA-N n-methylphenylalanine Chemical compound CNC(C(O)=O)CC1=CC=CC=C1 SCIFESDRCALIIM-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- YFZOUMNUDGGHIW-UHFFFAOYSA-M p-chloromercuribenzoic acid Chemical compound OC(=O)C1=CC=C([Hg]Cl)C=C1 YFZOUMNUDGGHIW-UHFFFAOYSA-M 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000013600 plasmid vector Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000018398 positive regulation of bone resorption Effects 0.000 description 1
- 230000001323 posttranslational effect Effects 0.000 description 1
- 230000001144 postural effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 239000003881 protein kinase C inhibitor Substances 0.000 description 1
- 238000001742 protein purification Methods 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960003581 pyridoxal Drugs 0.000 description 1
- 235000008164 pyridoxal Nutrition 0.000 description 1
- 239000011674 pyridoxal Substances 0.000 description 1
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 1
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 description 1
- 229960001327 pyridoxal phosphate Drugs 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000010188 recombinant method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 108010068072 salmon calcitonin Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000007423 screening assay Methods 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- 238000001542 size-exclusion chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- IHQKEDIOMGYHEB-UHFFFAOYSA-M sodium dimethylarsinate Chemical compound [Na+].C[As](C)([O-])=O IHQKEDIOMGYHEB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 239000003104 tissue culture media Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000005253 yeast cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/635—Parathyroid hormone, i.e. parathormone; Parathyroid hormone-related peptides
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K2319/00—Fusion polypeptide
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Physical Education & Sports Medicine (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Zoology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Genetics & Genomics (AREA)
- Toxicology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Mobile Radio Communication Systems (AREA)
- Transceivers (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPK387990 | 1990-12-13 | ||
| AU3879 | 1990-12-13 | ||
| AU9567 | 1991-11-19 | ||
| AUPK956791 | 1991-11-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06503330A JPH06503330A (ja) | 1994-04-14 |
| JP3280021B2 true JP3280021B2 (ja) | 2002-04-30 |
Family
ID=25643990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50160992A Expired - Lifetime JP3280021B2 (ja) | 1990-12-13 | 1991-12-13 | 骨吸収を阻害する化合物及び組成物 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5688760A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0561877B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP3280021B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE181336T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU666838B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2096933C (cg-RX-API-DMAC7.html) |
| DE (1) | DE69131355T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK0561877T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2135398T3 (cg-RX-API-DMAC7.html) |
| GR (1) | GR3030947T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUT64565A (cg-RX-API-DMAC7.html) |
| WO (1) | WO1992010511A1 (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006508646A (ja) * | 2002-08-15 | 2006-03-16 | バスキュロスタティン エルエルシー | ＰＴＨｒＰ由来の平滑筋増殖モジュレータ |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI954721L (fi) * | 1993-04-08 | 1995-11-22 | Ciba Geigy Ag | Luuresorptiota inhiboivat sykliset yhdisteet ja koostumukset |
| GB9425582D0 (en) * | 1994-12-19 | 1995-02-15 | Iaf Biochem Int | Peptides having immunomodulatory activity |
| AU691725B2 (en) * | 1995-02-20 | 1998-05-21 | Masahiro Iwamoto | Therapeutics of osteoarthritis and inflammatory joint disease |
| CN1079290C (zh) * | 1995-03-20 | 2002-02-20 | 国际壳牌研究有限公司 | 催化剂再生的方法 |
| EP0902036A1 (en) | 1997-09-05 | 1999-03-17 | Roche Diagnostics GmbH | Peptide containing an arginine mimetic for the treatment of osteoporosis, their production, and drugs containing these compounds |
| IL138214A0 (en) * | 1998-03-09 | 2001-10-31 | Zealand Pharmaceuticals As | Pharmacolgically active peptide conjugates having a reduced tendency towards enzymatic hydrolysis |
| EP1531855A4 (en) * | 2002-01-10 | 2009-07-22 | Osteotrophin Llc | TREATMENT OF BONE DISEASES WITH SKELETTAL ANABOLIKA |
| WO2009033722A2 (en) * | 2007-09-11 | 2009-03-19 | Mondobiotech Laboratories Ag | Use of a octreotide as a therapeutic agent |
| ES2605813B1 (es) * | 2015-09-16 | 2018-01-17 | Fundación Instituto De Investigación Sanitaria Fundación Jiménez Díaz | Uso de osteostatina en la preparación de un medicamento para el tratamiento de artrosis |
| EP4218784A3 (en) * | 2017-05-22 | 2023-09-13 | National Hellenic Research Foundation | Macrocyclic modulators of disease associated protein misfolding and aggregation |
| WO2024238631A2 (en) * | 2023-05-15 | 2024-11-21 | Purdue Research Foundation | A cytokine-like propeptide gene therapy platform |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL78342A (en) * | 1985-04-04 | 1991-06-10 | Gen Hospital Corp | Pharmaceutical composition for treatment of osteoporosis in humans comprising a parathyroid hormone or a fragment thereof |
| JPS63259972A (ja) * | 1987-04-17 | 1988-10-27 | Fuji Electric Co Ltd | 燃料電池設備 |
| CA1341048C (en) * | 1987-05-20 | 2000-07-11 | Thomas John Martin | Method and compositions for making acsf and acsf antagonists |
| US5312810A (en) * | 1987-05-20 | 1994-05-17 | The University Of Melbourne | Method and compositions for making ACSF and ACSF antagonists |
| US4819504A (en) * | 1987-05-27 | 1989-04-11 | Sampson Sports, Inc. | Self contained braking system for bicycle pedals |
| EP0341962B1 (en) * | 1988-05-09 | 1995-03-15 | Merck & Co. Inc. | Humoral hypercalcemic factor antagonists |
| JP2752987B2 (ja) * | 1988-06-01 | 1998-05-18 | 株式会社東芝 | リン酸型燃料電池発電プラント |
-
1991
- 1991-12-13 JP JP50160992A patent/JP3280021B2/ja not_active Expired - Lifetime
- 1991-12-13 DK DK92900438T patent/DK0561877T3/da active
- 1991-12-13 DE DE69131355T patent/DE69131355T2/de not_active Expired - Lifetime
- 1991-12-13 EP EP92900438A patent/EP0561877B1/en not_active Expired - Lifetime
- 1991-12-13 HU HU9301726A patent/HUT64565A/hu unknown
- 1991-12-13 WO PCT/AU1991/000580 patent/WO1992010511A1/en not_active Ceased
- 1991-12-13 ES ES92900438T patent/ES2135398T3/es not_active Expired - Lifetime
- 1991-12-13 US US08/064,111 patent/US5688760A/en not_active Expired - Lifetime
- 1991-12-13 AU AU90632/91A patent/AU666838B2/en not_active Expired
- 1991-12-13 AT AT92900438T patent/ATE181336T1/de not_active IP Right Cessation
- 1991-12-13 CA CA002096933A patent/CA2096933C/en not_active Expired - Lifetime
-
1999
- 1999-08-10 GR GR990402028T patent/GR3030947T3/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006508646A (ja) * | 2002-08-15 | 2006-03-16 | バスキュロスタティン エルエルシー | ＰＴＨｒＰ由来の平滑筋増殖モジュレータ |
Also Published As
| Publication number | Publication date |
|---|---|
| HU9301726D0 (en) | 1993-10-28 |
| AU666838B2 (en) | 1996-02-29 |
| US5688760A (en) | 1997-11-18 |
| EP0561877A1 (en) | 1993-09-29 |
| WO1992010511A1 (en) | 1992-06-25 |
| GR3030947T3 (en) | 1999-11-30 |
| EP0561877A4 (cg-RX-API-DMAC7.html) | 1994-03-23 |
| CA2096933C (en) | 2003-05-13 |
| DE69131355D1 (de) | 1999-07-22 |
| DE69131355T2 (de) | 1999-12-30 |
| JPH06503330A (ja) | 1994-04-14 |
| ATE181336T1 (de) | 1999-07-15 |
| HUT64565A (en) | 1994-01-28 |
| AU9063291A (en) | 1992-07-08 |
| CA2096933A1 (en) | 1992-06-14 |
| EP0561877B1 (en) | 1999-06-16 |
| ES2135398T3 (es) | 1999-11-01 |
| DK0561877T3 (da) | 1999-12-27 |
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