IL113113A - Vitamin d analogues process for their preparation and pharmaceutical compositions containing them - Google Patents
Vitamin d analogues process for their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL113113A IL113113A IL11311395A IL11311395A IL113113A IL 113113 A IL113113 A IL 113113A IL 11311395 A IL11311395 A IL 11311395A IL 11311395 A IL11311395 A IL 11311395A IL 113113 A IL113113 A IL 113113A
- Authority
- IL
- Israel
- Prior art keywords
- disease
- compounds
- group
- formula
- compound
- Prior art date
Links
- 229940046008 vitamin d Drugs 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title claims description 46
- 238000002360 preparation method Methods 0.000 title claims description 39
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 230000008569 process Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 187
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 94
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 46
- -1 cyclohexylidene moiety Chemical group 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 19
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims abstract description 17
- 239000011710 vitamin D Substances 0.000 claims abstract description 16
- 229930003316 Vitamin D Natural products 0.000 claims abstract description 15
- 235000019166 vitamin D Nutrition 0.000 claims abstract description 15
- 150000003710 vitamin D derivatives Chemical class 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 76
- 238000006243 chemical reaction Methods 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 208000020084 Bone disease Diseases 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 238000006317 isomerization reaction Methods 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 102000003982 Parathyroid hormone Human genes 0.000 claims description 6
- 108090000445 Parathyroid hormone Proteins 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
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- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 239000000199 parathyroid hormone Substances 0.000 claims description 6
- 229960001319 parathyroid hormone Drugs 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 208000028698 Cognitive impairment Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000021642 Muscular disease Diseases 0.000 claims description 5
- 201000009623 Myopathy Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 208000001132 Osteoporosis Diseases 0.000 claims description 5
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 5
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 5
- 206010039966 Senile dementia Diseases 0.000 claims description 5
- 206010052779 Transplant rejections Diseases 0.000 claims description 5
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- 230000009826 neoplastic cell growth Effects 0.000 claims description 5
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- 230000002265 prevention Effects 0.000 claims description 5
- 208000007442 rickets Diseases 0.000 claims description 5
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 230000001629 suppression Effects 0.000 claims description 5
- 230000029663 wound healing Effects 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- 208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 201000006409 renal osteodystrophy Diseases 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000000640 hydroxylating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 208000013038 Hypocalcemia Diseases 0.000 claims 6
- 230000000705 hypocalcaemia Effects 0.000 claims 6
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 4
- 206010004659 Biliary cirrhosis Diseases 0.000 claims 4
- 208000000038 Hypoparathyroidism Diseases 0.000 claims 4
- 208000029663 Hypophosphatemia Diseases 0.000 claims 4
- 208000001647 Renal Insufficiency Diseases 0.000 claims 4
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 claims 4
- 206010041969 Steatorrhoea Diseases 0.000 claims 4
- 201000006370 kidney failure Diseases 0.000 claims 4
- 208000005368 osteomalacia Diseases 0.000 claims 4
- 208000001162 steatorrhea Diseases 0.000 claims 4
- 208000003217 Tetany Diseases 0.000 claims 2
- 230000001184 hypocalcaemic effect Effects 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 description 108
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 96
- 229910052739 hydrogen Inorganic materials 0.000 description 72
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 70
- 239000000047 product Substances 0.000 description 65
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 58
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 54
- 101150041968 CDC13 gene Proteins 0.000 description 52
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 48
- KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical compound CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000004587 chromatography analysis Methods 0.000 description 26
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 150000001408 amides Chemical class 0.000 description 17
- 229910052727 yttrium Inorganic materials 0.000 description 17
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 13
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 8
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- 150000002148 esters Chemical class 0.000 description 8
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 7
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 230000000125 calcaemic effect Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 150000001299 aldehydes Chemical group 0.000 description 5
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 5
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- 229910052698 phosphorus Inorganic materials 0.000 description 5
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- 238000010626 work up procedure Methods 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
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- 229960005084 calcitriol Drugs 0.000 description 4
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- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 4
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- MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
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- ZSUUCLLIOSUIFH-UHFFFAOYSA-N n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(C)=O ZSUUCLLIOSUIFH-UHFFFAOYSA-N 0.000 description 3
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 235000001892 vitamin D2 Nutrition 0.000 description 3
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- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000007726 management method Methods 0.000 description 2
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- 210000001616 monocyte Anatomy 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- LMTGCJANOQOGPI-UHFFFAOYSA-N n-methyl-n-phenylacetamide Chemical compound CC(=O)N(C)C1=CC=CC=C1 LMTGCJANOQOGPI-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
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- 125000003003 spiro group Chemical group 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/18—Drugs for disorders of the endocrine system of the parathyroid hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Nutrition Science (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9405715A GB9405715D0 (en) | 1994-03-23 | 1994-03-23 | Chemical compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL113113A0 IL113113A0 (en) | 1995-06-29 |
| IL113113A true IL113113A (en) | 2001-03-19 |
Family
ID=10752346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL11311395A IL113113A (en) | 1994-03-23 | 1995-03-23 | Vitamin d analogues process for their preparation and pharmaceutical compositions containing them |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5811562A (fr) |
| EP (1) | EP0751932B1 (fr) |
| JP (1) | JP3790544B2 (fr) |
| KR (1) | KR100361556B1 (fr) |
| CN (1) | CN1073557C (fr) |
| AT (1) | ATE181063T1 (fr) |
| AU (1) | AU685249B2 (fr) |
| CA (1) | CA2185813A1 (fr) |
| CZ (1) | CZ290304B6 (fr) |
| DE (1) | DE69510189T2 (fr) |
| DK (1) | DK0751932T3 (fr) |
| ES (1) | ES2132651T3 (fr) |
| FI (1) | FI112359B (fr) |
| GB (1) | GB9405715D0 (fr) |
| GR (1) | GR3031084T3 (fr) |
| HU (1) | HUT75520A (fr) |
| IL (1) | IL113113A (fr) |
| NO (1) | NO309188B1 (fr) |
| NZ (1) | NZ282453A (fr) |
| WO (1) | WO1995025718A1 (fr) |
| ZA (1) | ZA952377B (fr) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19619036A1 (de) | 1996-04-30 | 1997-11-13 | Schering Ag | Neue Vitamin D-Derivate mit carbo- oder heterocyclischen Substituenten an C-25, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
| US6043385A (en) * | 1997-12-16 | 2000-03-28 | Hoffman-La Roche Inc. | Vitamin D derivatives |
| DE19935771A1 (de) * | 1999-07-23 | 2001-02-01 | Schering Ag | Neue Vitamin D-Derivate mit cyclischen Substrukturen in den Seitenketten, Verfahren und Zwischenprodukte zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
| WO2001012312A2 (fr) * | 1999-08-17 | 2001-02-22 | Battelle Memorial Institute | Reacteur chimique et procede permettant de conduire des reactions catalytiques avec des reactifs en phase gazeuse |
| AU2005201074B2 (en) * | 1999-08-17 | 2007-10-18 | Battelle Memorial Institute | A Chemical reactor and method for gas phase reactant catalytic reactions |
| US6358939B1 (en) | 1999-12-21 | 2002-03-19 | Northern Lights Pharmaceuticals, Llc | Use of biologically active vitamin D compounds for the prevention and treatment of inflammatory bowel disease |
| US6989377B2 (en) | 1999-12-21 | 2006-01-24 | Wisconsin Alumni Research Foundation | Treating vitamin D responsive diseases |
| WO2002028862A2 (fr) | 2000-10-02 | 2002-04-11 | Emory University | Analogues de triptolides destines au traitement des troubles autoimmuns et inflammatoires |
| CA2981549A1 (fr) | 2009-01-27 | 2010-08-05 | Berg Llc | Vitamines d3 et analogues de celles-ci pour soulagement des effets secondaires associes a une chimiotherapie |
| CN106265695B (zh) | 2009-08-14 | 2021-05-07 | 博格有限责任公司 | 用于治疗脱发的维生素d3及其类似物 |
| CN112156097A (zh) | 2013-05-29 | 2021-01-01 | 博格有限责任公司 | 使用维生素d预防或减轻化疗诱发的脱发 |
| JP7644444B2 (ja) * | 2021-03-02 | 2025-03-12 | 学校法人東京理科大学 | 異性体調製装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU221008B1 (hu) * | 1991-11-07 | 2002-07-29 | Research Institute For Medicine And Chemistry | D-vitamin-származékok és azokat tartalmazó gyógyászati készítmények |
| GB9206648D0 (en) * | 1992-03-26 | 1992-05-06 | Leo Pharm Prod Ltd | Chemical compounds |
| DE4234382A1 (de) * | 1992-10-06 | 1994-04-07 | Schering Ag | 25-Carbonsäure-Derivate in der Vitamin D-Reihe, Verfahren zu ihrer Herstellung, Zwischenprodukte für dieses Verfahren, diese Derivate enthaltende pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| GB9309422D0 (en) * | 1993-05-07 | 1993-06-23 | Res Inst Medicine Chem | Chemical compounds |
-
1994
- 1994-03-23 GB GB9405715A patent/GB9405715D0/en active Pending
-
1995
- 1995-03-23 HU HU9602572A patent/HUT75520A/hu unknown
- 1995-03-23 CN CN95192735A patent/CN1073557C/zh not_active Expired - Fee Related
- 1995-03-23 WO PCT/GB1995/000658 patent/WO1995025718A1/fr not_active Ceased
- 1995-03-23 IL IL11311395A patent/IL113113A/en not_active IP Right Cessation
- 1995-03-23 KR KR1019960705257A patent/KR100361556B1/ko not_active Expired - Fee Related
- 1995-03-23 AT AT95912345T patent/ATE181063T1/de not_active IP Right Cessation
- 1995-03-23 JP JP52450395A patent/JP3790544B2/ja not_active Expired - Fee Related
- 1995-03-23 US US08/704,613 patent/US5811562A/en not_active Expired - Fee Related
- 1995-03-23 CA CA002185813A patent/CA2185813A1/fr not_active Abandoned
- 1995-03-23 EP EP95912345A patent/EP0751932B1/fr not_active Expired - Lifetime
- 1995-03-23 ZA ZA952377A patent/ZA952377B/xx unknown
- 1995-03-23 ES ES95912345T patent/ES2132651T3/es not_active Expired - Lifetime
- 1995-03-23 AU AU19560/95A patent/AU685249B2/en not_active Ceased
- 1995-03-23 DE DE69510189T patent/DE69510189T2/de not_active Expired - Fee Related
- 1995-03-23 CZ CZ19962660A patent/CZ290304B6/cs unknown
- 1995-03-23 DK DK95912345T patent/DK0751932T3/da active
- 1995-03-23 NZ NZ282453A patent/NZ282453A/en unknown
-
1996
- 1996-09-20 FI FI963754A patent/FI112359B/fi not_active IP Right Cessation
- 1996-09-20 NO NO963949A patent/NO309188B1/no unknown
-
1999
- 1999-08-26 GR GR990402167T patent/GR3031084T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE181063T1 (de) | 1999-06-15 |
| KR100361556B1 (ko) | 2003-02-17 |
| DE69510189D1 (de) | 1999-07-15 |
| GR3031084T3 (en) | 1999-12-31 |
| JPH09510472A (ja) | 1997-10-21 |
| KR970701692A (ko) | 1997-04-12 |
| CZ266096A3 (en) | 1997-06-11 |
| CA2185813A1 (fr) | 1995-09-28 |
| WO1995025718A1 (fr) | 1995-09-28 |
| NO309188B1 (no) | 2000-12-27 |
| FI112359B (fi) | 2003-11-28 |
| NZ282453A (en) | 1997-04-24 |
| AU1956095A (en) | 1995-10-09 |
| HUT75520A (en) | 1997-05-28 |
| EP0751932A1 (fr) | 1997-01-08 |
| NO963949D0 (no) | 1996-09-20 |
| CN1149288A (zh) | 1997-05-07 |
| FI963754L (fi) | 1996-09-20 |
| CZ290304B6 (cs) | 2002-07-17 |
| US5811562A (en) | 1998-09-22 |
| GB9405715D0 (en) | 1994-05-11 |
| CN1073557C (zh) | 2001-10-24 |
| DE69510189T2 (de) | 1999-11-11 |
| HU9602572D0 (en) | 1996-11-28 |
| IL113113A0 (en) | 1995-06-29 |
| ES2132651T3 (es) | 1999-08-16 |
| EP0751932B1 (fr) | 1999-06-09 |
| NO963949L (no) | 1996-11-22 |
| AU685249B2 (en) | 1998-01-15 |
| DK0751932T3 (da) | 1999-11-15 |
| ZA952377B (en) | 1996-02-07 |
| FI963754A0 (fi) | 1996-09-20 |
| JP3790544B2 (ja) | 2006-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |