JP2011516672A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011516672A5 JP2011516672A5 JP2011503216A JP2011503216A JP2011516672A5 JP 2011516672 A5 JP2011516672 A5 JP 2011516672A5 JP 2011503216 A JP2011503216 A JP 2011503216A JP 2011503216 A JP2011503216 A JP 2011503216A JP 2011516672 A5 JP2011516672 A5 JP 2011516672A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- disease
- pharmaceutical composition
- composition
- pharmaceutically acceptable
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 4
- 229940013085 2-diethylaminoethanol Drugs 0.000 claims description 2
- 239000004475 Arginine Chemical class 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N Diethylethanolamine Chemical class CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical class NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical class OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- 239000004472 Lysine Chemical class 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical class CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N ethanolamine Chemical class NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical class CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- KIUKXJAPPMFGSW-MNSSHETKSA-N Hyaluronan Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-MNSSHETKSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 230000002757 inflammatory Effects 0.000 claims 4
- 208000009745 Eye Disease Diseases 0.000 claims 3
- 229940099552 Hyaluronan Drugs 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 201000004624 dermatitis Diseases 0.000 claims 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 3
- 229920002674 hyaluronan Polymers 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 206010012601 Diabetes mellitus Diseases 0.000 claims 2
- 206010021972 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000006641 Skin Disease Diseases 0.000 claims 2
- 238000005804 alkylation reaction Methods 0.000 claims 2
- 230000003110 anti-inflammatory Effects 0.000 claims 2
- 231100000406 dermatitis Toxicity 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 230000003637 steroidlike Effects 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 200000000019 wound Diseases 0.000 claims 2
- 206010000496 Acne Diseases 0.000 claims 1
- 208000009621 Actinic Keratosis Diseases 0.000 claims 1
- 206010069351 Acute lung injury Diseases 0.000 claims 1
- 206010064930 Age-related macular degeneration Diseases 0.000 claims 1
- 208000002205 Allergic Conjunctivitis Diseases 0.000 claims 1
- 208000002029 Allergic Contact Dermatitis Diseases 0.000 claims 1
- 206010057380 Allergic keratitis Diseases 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 208000008581 Brain Disease Diseases 0.000 claims 1
- 208000008787 Cardiovascular Disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 208000005679 Eczema Diseases 0.000 claims 1
- 208000010201 Exanthema Diseases 0.000 claims 1
- 208000008665 Gastrointestinal Disease Diseases 0.000 claims 1
- 240000008669 Hedera helix Species 0.000 claims 1
- 206010062639 Herpes dermatitis Diseases 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- 229940088597 Hormone Drugs 0.000 claims 1
- 206010021425 Immune system disease Diseases 0.000 claims 1
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 1
- 208000001083 Kidney Disease Diseases 0.000 claims 1
- 229960005015 Local anesthetics Drugs 0.000 claims 1
- 229940083877 Local anesthetics for treatment of hemorrhoids and anal fissures for topical use Drugs 0.000 claims 1
- 208000009856 Lung Disease Diseases 0.000 claims 1
- 229940035363 MUSCLE RELAXANTS Drugs 0.000 claims 1
- 208000002780 Macular Degeneration Diseases 0.000 claims 1
- 229940083876 Muscle relaxants FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 claims 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-Acetylglucosamine Chemical group CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 claims 1
- 229920000272 Oligonucleotide Polymers 0.000 claims 1
- 206010067621 Oral disease Diseases 0.000 claims 1
- 206010037844 Rash Diseases 0.000 claims 1
- 206010072736 Rheumatic disease Diseases 0.000 claims 1
- 206010039073 Rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 Rhinitis Diseases 0.000 claims 1
- 241001303601 Rosacea Species 0.000 claims 1
- 206010039580 Scar Diseases 0.000 claims 1
- 208000008742 Seborrheic Dermatitis Diseases 0.000 claims 1
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims 1
- 208000007056 Sickle Cell Anemia Diseases 0.000 claims 1
- 210000003491 Skin Anatomy 0.000 claims 1
- 206010040943 Skin ulcer Diseases 0.000 claims 1
- 239000000150 Sympathomimetic Substances 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 230000000202 analgesic Effects 0.000 claims 1
- 230000000844 anti-bacterial Effects 0.000 claims 1
- 230000001773 anti-convulsant Effects 0.000 claims 1
- 230000000843 anti-fungal Effects 0.000 claims 1
- 230000001754 anti-pyretic Effects 0.000 claims 1
- 230000002921 anti-spasmodic Effects 0.000 claims 1
- 230000000840 anti-viral Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000002221 antipyretic Substances 0.000 claims 1
- -1 antispasmodics Substances 0.000 claims 1
- 239000003699 antiulcer agent Substances 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000000271 cardiovascular Effects 0.000 claims 1
- 239000002327 cardiovascular agent Substances 0.000 claims 1
- 230000002254 contraceptive Effects 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 201000003883 cystic fibrosis Diseases 0.000 claims 1
- 231100000080 dermatitis contact Toxicity 0.000 claims 1
- 125000000600 disaccharide group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 231100001003 eczema Toxicity 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 201000005884 exanthem Diseases 0.000 claims 1
- 201000002146 gastrointestinal system disease Diseases 0.000 claims 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims 1
- 239000003102 growth factor Substances 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 230000000147 hypnotic Effects 0.000 claims 1
- 238000007918 intramuscular administration Methods 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 201000004614 iritis Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000003589 local anesthetic agent Substances 0.000 claims 1
- 229940064003 local anesthetic throat preparations Drugs 0.000 claims 1
- 230000003340 mental Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 claims 1
- 230000000926 neurological Effects 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 201000008838 periodontal disease Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrugs Drugs 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000004681 psoriasis Diseases 0.000 claims 1
- 230000000241 respiratory Effects 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 230000037390 scarring Effects 0.000 claims 1
- 230000037387 scars Effects 0.000 claims 1
- 230000001624 sedative Effects 0.000 claims 1
- 239000000932 sedative agent Substances 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 231100000019 skin ulcer Toxicity 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 238000005670 sulfation reaction Methods 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 210000001519 tissues Anatomy 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- AEMOLEFTQBMNLQ-QIUUJYRFSA-N β-D-glucuronic acid Chemical group O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-QIUUJYRFSA-N 0.000 claims 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K Aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper(II) hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L Iron(II) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L Magnesium hydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 102100020102 SAGE1 Human genes 0.000 description 1
- 101700079108 SAGE1 Proteins 0.000 description 1
- 235000017276 Salvia Nutrition 0.000 description 1
- 241001072909 Salvia Species 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L Zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- MSNWSDPPULHLDL-UHFFFAOYSA-K iron(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Fe+3] MSNWSDPPULHLDL-UHFFFAOYSA-K 0.000 description 1
- 229910021506 iron(II) hydroxide Inorganic materials 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Description
本明細書に記載されたアルキル化およびフルオロアルキル化ＳＡＧＥはいずれもその薬学的に許容される塩またはエステルであってもよい。薬学的に許容される塩は、遊離酸を適量の薬学的に許容される塩基で処理することによって調製される。代表的な薬学的に許容される塩基は、水酸化アンモニウム、水酸化ナトリウム、水酸化カリウム、水酸化リチウム、水酸化カルシウム、水酸化マグネシウム、水酸化第１鉄、水酸化亜鉛、水酸化銅、水酸化アルミニウム、水酸化第２鉄、イソプロピルアミン、トリメチルアミン、ジエチルアミン、トリエチルアミン、トリプロピルアミン、エタノールアミン、２−ジメチルアミノエタノール、２−ジエチルアミノエタノール、リジン、アルギニン、ヒスチジン等である。一態様においては、反応は、水を単独または水と混合可能な不活性有機溶媒との混合物中において約０℃〜約１００℃の温度（室温等）で実施される。構造式Ｉの化合物対使用される塩基のモル比は、任意の特定の塩に所望される比が得られるように選択される。例えば、遊離酸出発物質のアンモニウム塩を調製する場合は、出発物質を約１当量の薬学的に許容される塩基で処理することによって中性塩を得てもよい。
Claims (21)
- 修飾されたヒアルロナンまたはその薬学的に許容される塩もしくはエステルを含む化合物であって、前記ヒアルロナンまたはその薬学的に許容される塩もしくはエステルが少なくとも１個の硫酸基を含み、かつＮ−アセチル−グルコサミン残基の少なくとも１個の第１級Ｃ−６ヒドロキシル位に非置換のアルキル基またはフルオロアルキル基を含む、化合物。
- 前記非置換のアルキル基が、Ｃ１〜Ｃ１０分岐または直鎖アルキル基を含む、請求項１に記載の化合物。
- 前記非置換のアルキル基が、メチル、エチル、プロピル、イソプロピル、ブチル、ペンチル、またはヘキシルである、請求項１または２に記載の化合物。
- 前記フルオロアルキル基が、少なくとも１個のトリフルオロメチル基または−ＣＨ２（ＣＦ２）ｎＣＦ３（式中、ｎは、０〜１０の整数である）を含む、請求項１に記載の化合物。
- 前記薬学的に許容されるエステルが、プロドラッグである、請求項１〜４のいずれか一項に記載の化合物。
- 前記Ｎ−アセチル−グルコサミン残基の前記第１級Ｃ−６ヒドロキシルプロトンの１％〜５０％が、アルキル基またはフルオロアルキル基で置換されている、請求項１〜５のいずれか一項に記載の化合物。
- 前記ヒアルロナンの分子量が、アルキル化またはフルオロアルキル化前は１０ｋＤａを超え、好ましくはアルキル化またはフルオロアルキル化前は４０ｋＤａ〜２０００ｋＤａである、請求項１〜６のいずれか一項に記載の化合物。
- ヒアルロナンのグルクロン酸環上に存在するＣ−２ヒドロキシルプロトンおよび／またはＣ−３ヒドロキシルプロトンが硫酸基で置換されており、前記化合物の硫酸化度が二糖単位当たり０．５〜３．５であり、かつ前記化合物の分子量が２ｋＤａ〜１０ｋＤａである、請求項１〜７のいずれか一項に記載の化合物。
- ＮＨ ４＋ 、Ｎａ ＋ 、Ｌｉ ＋ 、Ｋ ＋ 、Ｃａ ＋２ 、Ｍｇ ＋２ 、Ｆｅ ＋２ 、Ｆｅ ＋３ 、Ｃｕ ＋２ 、Ａｌ ＋３ およびＺｎ ＋２ あるいはイソプロピルアミン、トリメチルアミン、ジエチルアミン、トリエチルアミン、トリプロピルアミン、エタノールアミン、２−ジメチルアミノエタノール、２−ジエチルアミノエタノール、リジン、アルギニンおよびヒスチジンの第４級塩からなる群から選択される、修飾されたヒアルロナンの薬学的に許容される塩である、請求項１に記載の化合物。
- 薬学的に許容される化合物および請求項１〜９のいずれか一項に記載の化合物を含む医薬組成物であって、静脈内、筋肉内、皮下、関節腔内、点眼、膣内、直腸内、鼻腔内、または局所投与することができる、組成物。
- 前記組成物が、抗炎症剤、解熱剤、ステロイド性および非ステロイド性抗炎症剤、ホルモン、成長因子、避妊薬、抗ウイルス剤、抗菌剤、抗真菌剤、鎮痛剤、催眠剤、鎮静剤、精神安定剤、抗痙攣薬、筋弛緩剤、局所麻酔剤、鎮痙薬、抗潰瘍薬、ペプチド性アゴニスト、交感神経作用薬、心血管作動薬、抗腫瘍剤、またはオリゴヌクレオチドをさらに含む、請求項１０に記載の組成物。
- 皮膚の表面に適用するための、請求項１〜１１のいずれか一項に記載の化合物または組成物を含む、皮膚障害の治療または予防用医薬組成物。
- 前記皮膚障害が、酒さ、アトピー性皮膚炎（湿疹）、アレルギー性接触皮膚炎、乾癬、ヘルペス状皮膚炎、ざ瘡、糖尿病性皮膚潰瘍および他の糖尿病性創傷、熱傷、日光皮膚炎、瘢痕予防、光線角化症、虫刺されによる炎症、ツタウルシによるかぶれ、放射線皮膚炎／熱傷、または脂漏性皮膚炎を含む、請求項１２に記載の医薬組成物。
- 眼に投与するための、請求項１〜１１のいずれか一項に記載の化合物または組成物を含む、眼疾患の治療または予防用医薬組成物。
- 前記眼疾患が、加齢黄斑変性、糖尿病性網膜症、眼球乾燥症候群、結膜炎、虹彩炎、ブドウ膜炎、アレルギー性結膜炎、または角膜炎および瘢痕を含む、請求項１４に記載の医薬組成物。
- 眼内投与される、請求項１４に記載の医薬組成物。
- 創傷に接触させるための、請求項１〜１１のいずれか一項に記載の化合物または組成物を含む、創傷治癒の改善用医薬組成物。
- 少なくとも１種の薬学的に許容される化合物の送達を必要とする患者にこのような送達を行うための、前記薬学的に許容される化合物を受容することができる少なくとも１つの組織に接触させる医薬組成物であって、請求項１〜１１のいずれか一項に記載の化合物または組成物を含み、前記化合物が、前記薬学的に許容される化合物を含む、医薬組成物。
- 眼科学的状態、尿生殖器状態、呼吸器状態、心血管状態、胃腸疾患、リウマチおよび免疫疾患、腎疾患、変性関節疾患、歯科もしくは口腔疾患、または神経疾患を治療または予防するための、請求項１〜１１のいずれか一項に記載の化合物または組成物を含む医薬組成物。
- 歯科または口腔外科において使用するための、請求項１〜１１のいずれか一項に記載の化合物または組成物を含む医薬組成物。
- 請求項１〜１１のいずれか一項に記載の化合物または組成物の有効量を含む、炎症を軽減または予防するための医薬組成物であって、前記炎症が、癌、多発性硬化症、変形性関節症、関節リウマチ、アルツハイマーのベータアミロイド、歯周疾患、炎症性腸疾患、喘息、鼻炎、副鼻腔炎、慢性閉塞性肺疾患、急性肺傷害、嚢胞性線維症、鎌状赤血球貧血、炎症性心血管疾患、炎症性肺疾患、炎症性眼疾患、間質性膀胱炎、炎症性脳疾患、または炎症性腸管疾患により生じる、医薬組成物。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4231008P | 2008-04-04 | 2008-04-04 | |
| US61/042,310 | 2008-04-04 | ||
| PCT/US2009/039498 WO2009124266A2 (en) | 2008-04-04 | 2009-04-03 | Alkylated sem-synthetic glycosaminoglycosan ethers, and methods for making and using thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011516672A JP2011516672A (ja) | 2011-05-26 |
| JP2011516672A5 true JP2011516672A5 (ja) | 2012-05-24 |
| JP5758797B2 JP5758797B2 (ja) | 2015-08-05 |
Family
ID=41055226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011503216A Active JP5758797B2 (ja) | 2008-04-04 | 2009-04-03 | アルキル化半合成グリコサミノグリカンエーテルならびにその製造および使用方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (5) | US8399430B2 (ja) |
| EP (1) | EP2281008B1 (ja) |
| JP (1) | JP5758797B2 (ja) |
| KR (1) | KR101594552B1 (ja) |
| CN (1) | CN102177180A (ja) |
| AU (1) | AU2009231634B2 (ja) |
| BR (1) | BRPI0909849A2 (ja) |
| CA (1) | CA2719666C (ja) |
| MX (1) | MX2010010904A (ja) |
| WO (1) | WO2009124266A2 (ja) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2719254C (en) | 2008-03-27 | 2019-04-30 | Purdue Research Foundation | Collagen-binding synthetic peptidoglycans, preparation, and methods of use |
| US8343942B2 (en) * | 2008-04-04 | 2013-01-01 | University Of Utah Research Foundation | Methods for treating interstitial cystitis |
| WO2009124266A2 (en) * | 2008-04-04 | 2009-10-08 | University Of Utah Research Foundation | Alkylated sem-synthetic glycosaminoglycosan ethers, and methods for making and using thereof |
| US20130035307A1 (en) * | 2010-01-26 | 2013-02-07 | University Of Utah Research Foundation | Methods for treating or preventing the spread of cancer using semi-synthetic glycosaminoglycosan ethers |
| CA2790682C (en) * | 2010-03-03 | 2020-11-24 | Neocutis Sa | Compositions and methods for the treatment of skin diseases and disorders using antimicrobial peptide sequestering compounds |
| US20130209531A1 (en) | 2010-06-08 | 2013-08-15 | University Of Utah Research Foundation | Applications of partially and fully sulfated hyaluronan |
| KR20140042795A (ko) * | 2011-03-23 | 2014-04-07 | 유니버시티 오브 유타 리서치 파운데이션 | 비뇨기 염증을 치료 또는 예방하는 방법 |
| US9522162B2 (en) | 2011-03-23 | 2016-12-20 | University Of Utah Research Foundation | Methods for treating or preventing urological inflammation |
| AU2012258706B2 (en) | 2011-05-24 | 2017-05-18 | Symic OA ApS | Hyaluronic acid-binding synthetic peptidoglycans, preparation, and methods of use |
| JP5873319B2 (ja) * | 2011-12-16 | 2016-03-01 | 株式会社コーセー | メイラード反応阻害剤 |
| AU2012354229B2 (en) | 2011-12-19 | 2016-12-01 | Dilafor Ab | Non anti-coagulative glycosaminoglycans comprising repeating disaccharide unit and their medical use |
| WO2013095215A1 (en) * | 2011-12-19 | 2013-06-27 | Dilaforette Ab | Low anticoagulant heparins |
| WO2013169355A1 (en) | 2012-05-09 | 2013-11-14 | Paringenix, Inc. | Treatment of myelosuppression |
| EP2849773A1 (en) * | 2012-05-14 | 2015-03-25 | University of Southern California | Methods for limiting development of a skin wound |
| US9717752B2 (en) | 2012-05-15 | 2017-08-01 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Uses of antagonists of hyaluronan signaling |
| EP2931753A1 (en) * | 2012-12-12 | 2015-10-21 | Solvay Specialty Polymers Italy S.p.A. | Fluorinated chitosan derivatives |
| SG11201506966RA (en) | 2013-03-15 | 2015-10-29 | Symic Biomedical Inc | Extracellular matrix-binding synthetic peptidoglycans |
| EP2807925A1 (en) * | 2013-05-26 | 2014-12-03 | Symrise AG | Antimicrobial compositions |
| EP3613423B1 (en) | 2013-07-10 | 2022-10-26 | Matrix Biology Institute | Compositions of hyaluronan with high elasticity and uses thereof |
| KR20160101898A (ko) * | 2013-10-22 | 2016-08-26 | 캔텍스 파마슈티칼즈, 인크. | 방사선 손상의 치료 및 예방 방법 |
| US9187576B2 (en) | 2013-11-25 | 2015-11-17 | Deuteria Biomaterials, Llc | Deuterium-enriched hyaluronan |
| US9637712B2 (en) | 2014-01-10 | 2017-05-02 | Lost Spirits Distillery, Llc | Method for rapid maturation of distilled spirits using light and heat processes |
| US10947488B2 (en) | 2014-01-10 | 2021-03-16 | Lost Spirits Technology Llc | Method for rapid maturation of distilled spirits using light and heat processes |
| US9637713B2 (en) | 2014-01-10 | 2017-05-02 | Lost Spirits Distillery, Llc | Method for rapid maturation of distilled spirits using light and heat processes |
| US10508259B2 (en) | 2014-01-10 | 2019-12-17 | Lost Spirits Technology Llc | Method for rapid maturation of distilled spirits using light, heat, and negative pressure processes |
| WO2015164822A1 (en) | 2014-04-25 | 2015-10-29 | Purdue Research Foundation | Collagen binding synthetic peptidoglycans for treatment of endothelial dysfunction |
| WO2016133910A1 (en) | 2015-02-17 | 2016-08-25 | Cantex Pharmaceuticals, Inc. | Treatment of cancers and hematopoietic stem cell disorders privileged by cxcl12-cxcr4 interaction |
| PL3842047T3 (pl) | 2015-09-24 | 2024-10-28 | Matrix Biology Institute | Kompozycje hialuronanu o wysokiej elastyczności i sposoby ich zastosowania |
| ITUB20155623A1 (it) * | 2015-11-16 | 2017-05-16 | Fidia Farm Spa | Processo migliorato per la produzione di HA solfatato di elevata purezza |
| US11337994B2 (en) | 2016-09-15 | 2022-05-24 | University Of Utah Research Foundation | In situ gelling compositions for the treatment or prevention of inflammation and tissue damage |
| US10849914B2 (en) | 2017-06-12 | 2020-12-01 | University Of Utah Research Foundation | Methods for producing chemoembolic agents for the delivery of anti-cancer agents |
| AU2018298224B2 (en) | 2017-07-07 | 2024-08-15 | Symic Ip, Llc | Synthetic bioconjugates |
| CN111491641A (zh) * | 2017-10-18 | 2020-08-04 | 格莱科米拉治疗公司 | 治疗慢性鼻窦炎的方法和组合物 |
| CN108586574B (zh) * | 2018-04-26 | 2019-11-12 | 国家海洋局第三海洋研究所 | 氨基葡萄糖肽类化合物及其制备方法与应用 |
| CN113164430A (zh) | 2018-06-03 | 2021-07-23 | 格莱科米拉治疗公司 | 用于在暴露于电离辐射和/或化学疗法之后预防严重健康后果和/或组织损伤的方法 |
| CN111228653A (zh) * | 2018-11-13 | 2020-06-05 | 格莱科米拉治疗公司 | 用电离辐射加强癌症治疗的方法 |
| WO2020159690A1 (en) | 2019-01-30 | 2020-08-06 | Bausch & Lomb Incorporated | Crosslinked polymeric network and use thereof |
| WO2022157307A1 (en) * | 2021-01-22 | 2022-07-28 | Dsm Ip Assets B.V. | Hyaluronic acid as antimicrobial agent for use on the skin |
| WO2022157314A1 (en) * | 2021-01-22 | 2022-07-28 | Dsm Ip Assets B.V. | Hyaluronic acid for use on the skin |
Family Cites Families (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2599172A (en) | 1948-11-29 | 1952-06-03 | Searle & Co | Sulfuric acid esters of hyaluronic acid and processes for the production thereof |
| US4240163A (en) * | 1979-01-31 | 1980-12-23 | Galin Miles A | Medicament coated intraocular lens |
| US5166331A (en) | 1983-10-10 | 1992-11-24 | Fidia, S.P.A. | Hyaluronics acid fractions, methods for the preparation thereof, and pharmaceutical compositions containing same |
| US4851521A (en) | 1985-07-08 | 1989-07-25 | Fidia, S.P.A. | Esters of hyaluronic acid |
| FR2584728B1 (fr) | 1985-07-12 | 1987-11-20 | Choay Sa | Procede de sulfatation de glycosaminoglycanes et de leurs fragments |
| AU604236B2 (en) | 1986-04-28 | 1990-12-13 | Iolab, Inc. | Intraocular dosage compositions and method of use |
| SE453394B (sv) * | 1986-07-07 | 1988-02-01 | Pharmacia Ab | Forfarande for framstellning av sulfaterade polysackarider genom anvendning av ett reducerande medel for sulfateringsreaktionen |
| EP0285357A3 (en) | 1987-03-31 | 1989-10-25 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Control of retroviruses |
| DK505588D0 (da) | 1988-02-26 | 1988-09-09 | Jesper Hamburger | Middel og anvendelse af samme |
| IT1217458B (it) | 1988-05-02 | 1990-03-22 | Crinos Ind Farmacoriologica S | Sulfoamino derivati di condroitin solfati,del dermatan solfato e dell' acido ialuronico e loro proprieta' farmacologiche |
| JP2769584B2 (ja) * | 1990-06-04 | 1998-06-25 | 参天製薬株式会社 | 局所投与用抗アレルギー剤 |
| IT1247175B (it) | 1991-04-19 | 1994-12-12 | Fidia Spa | Procedimento per la purificazione di acido ialuronico e frazione di acido ialuronico puro per uso oftalmico. |
| JPH06509731A (ja) | 1991-08-16 | 1994-11-02 | ギャリン，マイルス エイ | 薬剤被覆した屈折性の目前室挿入体 |
| ITPD940054A1 (it) * | 1994-03-23 | 1995-09-23 | Fidia Advanced Biopolymers Srl | Polisaccaridi solfatati |
| WO1996024362A1 (fr) | 1995-02-07 | 1996-08-15 | Shiseido Company, Ltd. | Agents anti-inflammatoires |
| GB2317182B (en) | 1996-09-11 | 2000-11-01 | Johnson & Johnson Medical | Sulfated polysaccharides and uses thereof in medical treatment |
| JPH10195107A (ja) | 1997-01-10 | 1998-07-28 | Shiseido Co Ltd | オリゴ硫酸化ヒアルロン酸 |
| JP4278716B2 (ja) * | 1997-04-04 | 2009-06-17 | フィディーア・ファルマチェウティチ・ソシエタ・ペル・アチオニ | Ｎ−硫酸化ヒアルロン酸化合物、その誘導体および製造方法 |
| US5981509A (en) | 1997-05-20 | 1999-11-09 | Shiseido Company, Ltd. | Preparation for prophylaxis or treatment of renal diseases containing sulfated polysaccharide |
| IT1293484B1 (it) | 1997-06-11 | 1999-03-01 | Fidia Advanced Biopolymers Srl | Materiale biologico comprendente una efficiente coltura di cellule e una matrice tridimensionale biocompatibile e biodegradabile |
| IT1294797B1 (it) * | 1997-07-28 | 1999-04-15 | Fidia Advanced Biopolymers Srl | Uso dei derivati dell'acido ialuronico nella preparazione di biomateriali aventi attivita' emostatica fisica e tamponante |
| ITPD980037A1 (it) | 1998-02-25 | 1999-08-25 | Fidia Advanced Biopolymers Srl | Acido ialuronico solfatato e i suoi derivati legati covalentemente a polimeri sintetici pe la preparazione di biomateriali e per il rivesti |
| DE19813234A1 (de) | 1998-03-26 | 1999-09-30 | Knoell Hans Forschung Ev | Verfahren zur Herstellung hochsulfatierter Hyaluronsäuren |
| JPH11279042A (ja) | 1998-03-30 | 1999-10-12 | Shiseido Co Ltd | 皮膚外用剤 |
| US6984667B2 (en) | 1998-04-08 | 2006-01-10 | Theta Biomedical Consulting And Development Co. | Synergistic proteoglycan compositions for inflammatory conditions |
| ITPD980149A1 (it) | 1998-06-17 | 1999-12-17 | Fidia Advanced Biopolymers Srl | Protesi tridimensionali comprendenti derivati dell'acido ialuronico per riparare o ricostruire i tessuti danneggiati e processo per la |
| ATE270677T1 (de) | 1998-07-31 | 2004-07-15 | Seikagaku Kogyo Co Ltd | Neues glycosaminoglycan und dieses enthaltendes arzneimittel |
| IT1303735B1 (it) | 1998-11-11 | 2001-02-23 | Falorni Italia Farmaceutici S | Acidi ialuronici reticolati e loro usi medici. |
| IT1306644B1 (it) | 1999-04-08 | 2001-10-02 | Fidia Advanced Biopolymers Srl | Strutture tridimensionali comprendenti derivati dell'acido ialuronicoottenibili mediante la tecnica antisolvente supercritico. |
| US6288043B1 (en) * | 1999-06-18 | 2001-09-11 | Orquest, Inc. | Injectable hyaluronate-sulfated polysaccharide conjugates |
| JP2001097997A (ja) | 1999-10-01 | 2001-04-10 | Shiseido Co Ltd | 硫酸化ヒアルロン酸を用いたアフィニティー吸着担体及びその使用 |
| JP4139029B2 (ja) * | 1999-12-10 | 2008-08-27 | 大阪瓦斯株式会社 | 電源装置 |
| JP2001163789A (ja) | 1999-12-13 | 2001-06-19 | Maruho Co Ltd | マトリックスメタロプロテアーゼ阻害用医薬組成物 |
| WO2001051003A2 (en) | 2000-01-10 | 2001-07-19 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Use of lipid conjugates in the treatment of disease |
| US6828308B2 (en) * | 2000-07-28 | 2004-12-07 | Sinclair Pharmaceuticals, Ltd. | Compositions and methods for the treatment or prevention of inflammation |
| IT1317359B1 (it) * | 2000-08-31 | 2003-06-16 | Fidia Advanced Biopolymers Srl | Polisaccaridi percarbossilati, quali l'acido ialuronico, processo perla loro preparazione e loro impiego in campo farmaceutico e |
| DE10053053A1 (de) * | 2000-10-19 | 2002-05-16 | Knoell Hans Forschung Ev | Pharmazeutische Formulierungen zur Hemmung von entzündlichen Arthritiden |
| ITPD20020064A1 (it) | 2002-03-12 | 2003-09-12 | Fidia Advanced Biopolymers Srl | Derivati esterei dell'acido ialuronico per la preparazione di idrogelda utilizzare in campo biomedico, sanitario e chirurgico e come sistem |
| WO2003086474A2 (en) | 2002-04-11 | 2003-10-23 | Carbomer, Inc | Fluorinated or paramagnetic alginate polymer, annexin paramagnetic conjugate, and their use as contrasting agent in mri |
| JP2005531648A (ja) | 2002-04-11 | 2005-10-20 | カルボマー インク | 生体適合性物質およびプローブ類 |
| CN102178692A (zh) | 2002-07-03 | 2011-09-14 | 派瑞克科学公司 | 透明质酸组合物以及使用方法 |
| JP2004262777A (ja) * | 2003-02-27 | 2004-09-24 | Shiseido Co Ltd | アセチル化ヒアルロン酸含有眼用医薬組成物 |
| DE10352137A1 (de) | 2003-11-04 | 2005-06-16 | Beschorner, Katharina, Dr. | Verwendung sulfatierter Hyaluronsäure |
| ZA200604869B (en) | 2003-12-04 | 2007-11-28 | Univ Utah Res Found | Modified macromolecules and methods of making and using thereof |
| US20050203056A1 (en) * | 2003-12-19 | 2005-09-15 | Aventis Pharma S.A. | Carboxyl-reduced derivatives of hyaluronic acid, preparation thereof, use thereof as a medicinal product and the pharmaceutical compositions containing them |
| FR2864090B1 (fr) * | 2003-12-19 | 2006-01-27 | Aventis Pharma Sa | Derives carboxy-reduits de l'acide hyaluronique, leur preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant |
| ITPD20040245A1 (it) | 2004-10-08 | 2005-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali costituiti da acido ialuronico solfatato e gellano utilizzabili nella prevenzione delle adesioni spinali |
| DE102005004643B4 (de) | 2005-01-28 | 2010-04-08 | Innovent E.V. Technologieentwicklung | Antivirale Kombinationen sowie ihre Verwendung |
| JP2006206849A (ja) | 2005-01-31 | 2006-08-10 | Seikagaku Kogyo Co Ltd | アルキルエステル化されたグリコサミノグリカンの製造方法 |
| US20090105463A1 (en) | 2005-03-29 | 2009-04-23 | Massachusetts Institute Of Technology | Compositions of and Methods of Using Oversulfated Glycosaminoglycans |
| US20060223781A1 (en) | 2005-04-04 | 2006-10-05 | Neoparin, Inc. | Process for induction of intramolecular migration of sulfates, phosphates, and other oxyanions |
| ITPD20050206A1 (it) | 2005-07-07 | 2007-01-08 | Fidia Advanced Biopolymers Srl | Biomateriali in forma di fibra da impiegarsi come dispositivi medici nel trattamento delle ferite e loro processi di produzione |
| US7993678B2 (en) | 2005-09-26 | 2011-08-09 | Novozymes Biopolymer A/S | Hyaluronic acid derivatives |
| US7517856B2 (en) | 2005-10-11 | 2009-04-14 | Ben-Gurion University Of The Negev Research And Development Authority | Bioconjugates comprising sulfated polysaccharides and their uses |
| CN103120701B (zh) | 2005-10-12 | 2014-11-05 | 生化学工业株式会社 | 包含疏水基团结合型糖胺聚糖在制备预防或治疗角膜上皮层病症的药物中的用途 |
| WO2007059890A1 (en) * | 2005-11-22 | 2007-05-31 | Centre National De Recherche Scientifique | New derivatives of hyaluronic acid, their preparation process and their uses |
| US20070166266A1 (en) * | 2006-01-19 | 2007-07-19 | Solazyme, Inc. | Methods and compositions for improving the health and appearance of skin |
| EP1994062B1 (en) | 2006-03-02 | 2009-07-15 | Novozymes Biopolymer A/S | Aryl/alkyl vinyl sulfone hyaluronic acid derivatives |
| ITPD20060219A1 (it) | 2006-05-31 | 2007-12-01 | Fidia Farmaceutici | Composizioni farmaceutiche contenenti acido ialuronico solfatato nel trattamento dell'osteoartrosi |
| WO2008008859A2 (en) | 2006-07-11 | 2008-01-17 | University Of Utah Research Foundation | Macromolecules modified with electrophilic groups and methods of making and using thereof |
| AR062046A1 (es) | 2006-07-25 | 2008-08-10 | Osmotica Pharmaceutical Argentina S A | Soluciones oftalmicas |
| TW200838552A (en) | 2007-01-25 | 2008-10-01 | Novozymes Biopolymer As | Methyl esters of hyaluronic acid |
| JP5088864B2 (ja) | 2007-03-16 | 2012-12-05 | オリンパス株式会社 | 生体組織補填材とその製造方法 |
| EP2025687A1 (en) | 2007-07-23 | 2009-02-18 | Istituto Scientifico di Chimica E Biochimica "G Ronzoni | Process for the preparation of heparanase-inhibiting sulfated hyaluronates and products obtained thereby |
| WO2009033047A2 (en) * | 2007-09-07 | 2009-03-12 | University Of Chicago | Methods and compositions for treating diseases and conditions involving higher molecular weight hyaluronan |
| EP2057983A1 (en) | 2007-11-07 | 2009-05-13 | Bruschettini S.r.l. | Compositions for the topical protection of the ocular tissues from the damaging effects of ultraviolet radiations |
| US8093365B2 (en) | 2008-03-03 | 2012-01-10 | New York University | Biocompatible materials containing stable complexes method of TSG-6 and hyaluronan and method of using same |
| US8343942B2 (en) | 2008-04-04 | 2013-01-01 | University Of Utah Research Foundation | Methods for treating interstitial cystitis |
| WO2009124266A2 (en) | 2008-04-04 | 2009-10-08 | University Of Utah Research Foundation | Alkylated sem-synthetic glycosaminoglycosan ethers, and methods for making and using thereof |
| MX2011008119A (es) | 2009-02-02 | 2011-08-24 | Otsuka Chemical Co Ltd | Derivado de acido hialuronico polisulfatado de bajo peso molecular, y medicamento que contiene el mismo. |
| US20100204325A1 (en) | 2009-02-11 | 2010-08-12 | Allergan, Inc. | Valproic acid drug delivery systems and intraocular therapeutic uses thereof |
| IT1393945B1 (it) | 2009-04-21 | 2012-05-17 | Fidia Farmaceutici | Composizioni comprendenti acido ialuronico, acido ialuronico solfatato, calcio e vitamina d3 nel trattamento delle malattie osteoarticolari e muscoloscheletriche |
| IT1397246B1 (it) | 2009-05-14 | 2013-01-04 | Fidia Farmaceutici | Nuovi medicamenti ad uso topico a base di acido ialuronico solfatato come agente attivante o inibente l'attivita' citochinica |
| IT1397247B1 (it) | 2009-05-14 | 2013-01-04 | Fidia Farmaceutici | Nuovi agenti regolatori dell'attivita' citochinica |
| US9522162B2 (en) | 2011-03-23 | 2016-12-20 | University Of Utah Research Foundation | Methods for treating or preventing urological inflammation |
-
2009
- 2009-04-03 WO PCT/US2009/039498 patent/WO2009124266A2/en active Application Filing
- 2009-04-03 EP EP09727633.1A patent/EP2281008B1/en active Active
- 2009-04-03 CN CN2009801208979A patent/CN102177180A/zh active Pending
- 2009-04-03 CA CA2719666A patent/CA2719666C/en active Active
- 2009-04-03 AU AU2009231634A patent/AU2009231634B2/en active Active
- 2009-04-03 BR BRPI0909849A patent/BRPI0909849A2/pt not_active IP Right Cessation
- 2009-04-03 MX MX2010010904A patent/MX2010010904A/es active IP Right Grant
- 2009-04-03 KR KR1020107024824A patent/KR101594552B1/ko active IP Right Grant
- 2009-04-03 JP JP2011503216A patent/JP5758797B2/ja active Active
-
2010
- 2010-08-27 US US12/870,774 patent/US8399430B2/en active Active
- 2010-08-27 US US12/870,763 patent/US7855187B1/en active Active
-
2011
- 2011-11-23 US US13/304,292 patent/US8329673B2/en active Active
-
2013
- 2013-01-07 US US13/735,124 patent/US8951990B2/en active Active
-
2015
- 2015-02-04 US US14/613,523 patent/US9549945B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011516672A5 (ja) | ||
| CA2771871C (en) | Pharmaceutical compositions comprising prednisolone metasulfobenzoate and 5-asa for treating ibd | |
| JP6389190B2 (ja) | 固溶体組成物および慢性炎症における使用 | |
| JP6462045B2 (ja) | スルフォラファンの単離及び精製 | |
| JP2010502583A (ja) | 非常に速い皮膚浸透率を有するアセトアミノフェン及び関連化合物の正荷電水溶性プロドラッグ | |
| RU2015150069A (ru) | 2,2-дифторопропионамидные производные бардоксолон-метила, полиморфные формы и способы их пременения | |
| JP2009543857A (ja) | イブプロフェンの正荷電水溶性プロドラッグ | |
| JP2004203795A (ja) | ピリドン誘導体の溶液状医薬組成物 | |
| WO2008147170A1 (es) | Nuevo proceso de síntesis para la obtención de 5-metil-1-fenil-2- (ih) -piridona, composición y uso de la misma | |
| US7854943B2 (en) | Phospholipid gel compositions for drug delivery and methods of treating conditions using same | |
| EP2506711A1 (en) | Hypersulfated disaccharide formulations | |
| JP2012518671A5 (ja) | ||
| WO2024193721A1 (zh) | 一种新的2-(1-羟基戊基)苯甲酸环烷胺盐 | |
| US20110245197A1 (en) | Hypersulfated glucopyranosides | |
| AU2005266449B2 (en) | Compound formulations of 2-amino-1,3-propanediol compounds | |
| CA2902232C (en) | Methods for treatment of ophthalmic diseases and disorders | |
| WO2020055916A1 (en) | Dithiolsaccharide mucolytic agents and uses thereof | |
| JP2013518061A5 (ja) | ||
| CN102225896A (zh) | 大黄酸的醚衍生物以及它们的治疗用途 | |
| TW202300177A (zh) | 新型肽綴合物 | |
| JP2018527406A (ja) | Ｓ１ｐ受容体モジュレーターを含む組成物 | |
| CS197252B2 (en) | Method of producing novel derivatives of oxyphenyl butazone | |
| US20100004200A1 (en) | Meloxicam and glucosamine formulation and uses thereof | |
| JP5855599B2 (ja) | 非常に速い皮膚浸透率を有するアセトアミノフェン及び関連化合物の正荷電水溶性プロドラッグ | |
| EP2340016A2 (en) | Topical formulation of 3-(2,2,2-trimethylhydrazinium) propionate dihydrate |