Technologies

Pharmaceuticals & Vitamin D : Vitamin D

Pharmaceuticals & Vitamin D Portfolios

Technologies

Vitamin D Analogs “WT-51” and “WT-52” Boost Bone and Skin Health

UW–Madison researchers have developed two new vitamin D3 analogs, (22E)-(24R/S)-2-methylene-22-dehydro-1α,24,25-trihydroxy-19-nor-vitamin D3, known as WT-51 and WT-52. These compounds show activity similar to that of the native hormone in stimulating intestinal calcium transport, but are up to 10 times more potent in promoting cell differentiation and gene transcription.
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Crystallized Vitamin D Analog “SAG-2”

UW–Madison researchers now have developed a method using a mixture of 2-propanol and hexane to crystallize SAG-2. Also, certain diol precursors formed during synthesis may be obtained in crystalline form using ethyl acetate as the solvent. This efficient process removes most of the contaminants from the synthetic SAG-2, resulting in a highly pure product.
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Crystallized Vitamin D Analog “24F2-DM”

UW–Madison researchers now have developed a method using a mixture of 2-propanol and hexane to crystallize 24F2-DM. This efficient process removes most of the contaminants from the synthetic 24F2-DM, resulting in a highly pure product.
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Crystallized Vitamin D Analog “F-24”

UW–Madison researchers now have developed a method using a mixture of 2-propanol and hexane to crystallize F-24. This efficient process removes most of the contaminants from the synthetic F-24, resulting in a highly pure product.
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Crystallized Vitamin D Analogs “MET-1” and “MET-2”

UW–Madison researchers now have developed a method using either diethyl ether or a mixture of 2-propanol and hexane to crystallize MET-1 and MET-2. This efficient process removes most of the contaminants from the synthetic forms, resulting in a highly pure product.
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Vitamin D Analog “DA2HE” to Treat and Prevent Polyps, Hyperplastic Intestinal Disorders

UW–Madison researchers have developed a vitamin D analog, seco-A-2,19-dinor-1,25-dihydroxyvitamin D3. Known as DA2HE, the compound exhibits high activity in vivo, especially in intestinal tissues. Relatively low receptor binding, differentiation and transcription activities suggest strong cell selectivity for use against polyps, some cancers and intestinal disorders. The compound’s high intestinal calcium transport activity may be useful against bone diseases.
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Vitamin D Analogs 2AMD and 2MD to Treat Islet Cell Transplant Patients

UW–Madison researchers have identified vitamin D analogs that could be used to promote the long-term survival and function of transplanted islet cells.

The compounds are 2α-methyl-19-nor-20(S)-1,25-dihydroxyvitamin D3 (known as 2AMD) and 2-methylene-19-nor-20(S)-1,25-dihydroxyvitamin D3 (known as 2MD).

A pharmaceutical containing the analogs and an immunosuppressant could be administered in an appropriate amount to an islet transplant patient, leading to a prolonged period of normoglycemia. This period preferably would last for several years.
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Vitamin D Analogs “2EG” and “T-2EG-S” for Treating Cancer and Bone Disease

UW–Madison researchers have developed vitamin D analogs (20S) and (20R)- 1a,25-dihydroxy-2-methylene-vitamin D3 and (5E)-(20S)-1a,25-dihysroxy-2-methylene-vitamin D3.These compounds exhibit high binding affinity and cell differentiation activity, suggesting anticancer properties. Also, high calcemic activity may be harnessed for the treatment of bone diseases where less frequent doses are desired.
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Vitamin D Analogs “1D-QM” and “1D-QMS” for Cancer, Bone Disease Therapy

UW–Madison researchers have developed vitamin D analogs (20S) and (20R)-25-hydroxy-2-methylene-vitamin D3. In vivo, these compounds could act as prodrugs since 1-hydroxylation can occur in a regulated manner and extended vitamin release activity is predicted. The compounds exhibit high binding affinity and cell differentiation activity, suggesting anticancer properties. Also, high calcemic activity may be harnessed for bone disease treatments in which less frequent doses are preferred, like senile osteoporosis.
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Vitamin D Analogs “3D-QM” and “3D-QMS” for Treating Cancer and Bone Diseases

UW–Madison researchers have developed vitamin D analogs (20S) and (20R)-3-desoxy-1a,25-dihydroxy-2-methylene vitamin D3.These compounds are known also as 3D-QMS and 3D-QM, respectively. They exhibit anticancer properties of high binding affinity and cell differentiation activity. High calcemic activity suggests treatment for bone ailments and diseases.
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Crystallized Vitamin D Analog 2-Methylene-18,19-Dinor-1Alpha-Hydroxy-Homopregnacalciferol

UW–Madison researchers now have developed a method using precipitation with hexane from ethyl acetate. This efficient process removes most of the contaminants, resulting in a highly pure product. Crystals acceptable for X-ray experiment also can be obtained using hexane from benzene via diffusion exchange.
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Crystallized Vitamin D Compound Known as “20DCM”

UW–Madison researchers now have developed a method of using ethyl formate or an ethyl formate and hexane mixture to crystallize 20DCM. This efficient process removes most of the contaminants from the synthetic 20DCM, resulting in a highly pure product.
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Vitamin D Analog “UW-05” for Skin Therapy, Parathyroid and Autoimmune Disease Treatment

UW–Madison researchers have developed a vitamin D analog, 2-methylene-(22E)-25-hexanoyl-24-oxo-26,27-cyclo-22-dehydro-19-nor-1α-hydroxyvitamin D3. Known as UW-05, the compound shows high transcription activity, pronounced activity in arresting proliferating cells and inducing their differentiation. Bone calcium mobilization activity is lower compared to the native hormone. UW-05 may be useful against autoimmune diseases, some cancers, skin wrinkles and disorders, inflammatory problems and obesity.
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Vitamin D Analogs for Treating Bone Cancers and Diseases

UW–Madison researchers have developed vitamin D analogs,(20S)-3-desoxy-2-methylene-1a,25-diydroxy-19-nor-vitamin D3 and (20R)-3-desoxy-2-methylene-1a,25-diydroxy-19-nor-vitamin D3.These compounds exhibit promising anti-cancer activities: high receptor binding, and the arrest and induced-differentiation of proliferating cells. High calcemic mobilization suggests particular effectiveness in the treatment of bone diseases.
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Vitamin D Analog “CPA-1” for Treating and Preventing Deadliest Cancers

UW–Madison researchers have developed a novel vitamin D analog, N-cycloporpyl-(20R)-2-methylene-19,26,27-trinor-25-aza-1a-hydroxyvitamin D3, also known as CPA-1. This compound binds to vitamin D receptors with high affinity, shows some cell-type selectivity, and is almost as potent as the native hormone in causing cellular differentiation. It also is less active than calcitriol in raising tissue calcium levels. It potentially may be developed into a useful anticancer agent.
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Vitamin D Analog “TS-17” for the Treatment of Cancer, Particularly Leukemia and Lung Cancer

UW–Madison researchers have developed a novel vitamin D analog, (20S)-25,26,27-trinor-24-(p-methylphenylsulfonate)-vitamin D3, also known as TS-17. This analog binds the vitamin D receptor with very low affinity and has very low ability to stimulate gene transcription. TS-17 has little calcemic activity and showed no calcium-related toxicity issues. It does not promote cellular differentiation, but has been shown to kill cancer cells in a leukemia cell line as well as in a small cell lung carcinoma cell line, making it potentially useful for the treatment of some types of cancer.
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Vitamin D Analog “AB-47” for Cancer Prevention and Treatment

UW–Madison researchers have developed a novel vitamin D analog, 22-bromoacetoxy-homopregnacalciferol, also known as AB-47. This analog binds the vitamin D receptor with much lower affinity than the native hormone, has very low ability to stimulate gene transcription and has little calcemic activity. AB-47 does not promote cancer cell differentiation. Instead, it has been shown to kill cancer cells in a leukemia cell line as well as in small cell lung carcinoma, making it potentially useful for the treatment of some types of cancer.
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Crystallized Vitamin D Compound Known as “NEL”

UW–Madison researchers now have developed a method of using water and methanol to crystallize NEL. This efficient process removes most of the contaminants from the synthetic NEL, resulting in a highly pure product.
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Vitamin D Analogs 2MD and 2AMD Prevent Type 1 Diabetes without Inducing Hypercalcemia

UW–Madison researchers have identified vitamin D analogs that can prevent type 1 diabetes in the NOD mouse at doses that do not induce hypercalcemia. The vitamin D compounds are 2α-methyl-19-nor-20(S)-1,25-dihydroxyvitamin D3, known as 2AMD, and 2-methylene-19-nor-20(S)-1,25-dihydroxyvitamin D3, known as 2MD.
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Vitamin D Analog for Cancer Prevention and Treatment

UW–Madison researchers have developed a novel vitamin D analog, (20S)-25-hydroxy-1-desoxy-2-methylene-19-nor-vitamin D3. This compound binds the vitamin D receptor and causes differentiation of cancer cells nearly as well as calcitriol but does not raise tissue calcium levels to the same degree, suggesting that it could be developed into a useful anticancer agent.
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Vitamin D Analog “N-23” for Cancer Prevention and Treatment

UW–Madison researchers have developed a novel vitamin D analog, (20S,22E)-methylene-19-nor-22-ene-1α,25-dihydroxyvitamin D3, also known as N-23. This compound binds the vitamin D receptor with the same affinity as the native hormone but is more potent in causing cellular differentiation and increasing expression of the 24-hydroxylase gene. It also is less active than calcitriol in causing intestinal calcium transport. It potentially may be developed into a useful anticancer agent.
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Vitamin D Analogs “DO-REVA” and “DO-REVB” for Cancer Prevention and Treatment

UW–Madison researchers have developed two novel vitamin D analogs, 1,2-cyclopentene-25-hydroxy-19-nor-vitamin D3, known as DO-REVA, and 3,2-cyclopentene-1α-25-dihydroxy-19-nor-vitamin D3, known as DO-REVB. Both analogs bind the vitamin D receptor with lower affinity than the native hormone. One of the analogs, DO-REVA, has measurable transcription activity at higher concentrations, suggesting that it may serve as a slow-release anticancer drug or be used as a local-acting drug when coupled with an appropriate delivery method. The other analog, DO-REVB, promotes cancer cell differentiation, making it potentially useful for the treatment of cancer. Like DO-REVA, DO-REVB also may serve as a slow-release or local-acting drug.
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Vitamin D Analog “Me-Cvit” Potentially Useful to Inhibit Hypercalcemia, Treat Cancer

UW–Madison researchers have developed a novel vitamin D analog, 1α,25-dihydroxy-6-methylvitamin D3, also known as Me-Cvit. This compound binds the vitamin D receptor with the same affinity as the native hormone but shows much less potency for other biological activities, including promotion of calcium transport. It could act as a dominant negative and be useful as an antidote for vitamin D intoxication to help treat hypercalcemia caused by a vitamin D analog. In addition, because Me-Cvit shows some cellular differentiation activity and ability to promote transcription of 24-hydroxylase but does not promote intestinal calcium transport, it may be useful as an anticancer agent, particularly for leukemia, colon cancer, breast cancer, skin cancer or prostate cancer.
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Vitamin D Compounds for the Treatment of Ocular Hypertension

UW–Madison researchers have developed a method of treating OHT by administering a vitamin D analog.  The vitamin D compound can be applied topically to one or both of an individual’s eyes to reduce IOP.
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Calcitonin and Calcitonin-Like Compounds for Multiple Sclerosis

UW-Madison researchers have developed methods of preventing and treating MS by administering synthetic calcitonin, calcitonin-like peptides or calcitonin mimetics to a patient to diminish MS symptoms.  Vitamin D analogs can be administered in combination with the calcitonin to further reduce symptoms. 
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2-Methylene-19,21-Dinor-1Alpha-Hydroxy-Bishomopregnacalciferol

UW-Madison researchers have developed a new vitamin D analog, 2-methylene-19,21-dinor-1α-hydroxy-bishomopregnacalciferol. Compared to 1α,25-dihydroxyvitamin D3, this compound exhibits relatively high binding to vitamin D receptors, very low intestinal calcium transport activity, and very low ability to mobilize calcium from bone. It also displays relatively high cell differentiation activity, making it potentially useful as an anti-cancer agent or a therapeutic agent for treating skin conditions.
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2-Methylene-19-Nor-1Alpha-Hydroxy-17-Ene-Homopregnacalciferol

UW-Madison researchers have developed a new vitamin D analog, 2-methylene-19-nor-1α-hydroxy-17-ene-homopregnacalciferol. This compound, a 2-methylene-19-nor-17-ene vitamin D analog, is characterized by a hydroxyl group at carbon 1, a methylene substituent at carbon 2, a double bond between carbons 17 and 20 and the elimination of carbons 23,24,25,26 and 27.

Compared to 1α,25-dihydroxyvitamin D3, the new analog exhibits relatively high binding to vitamin D receptors, very low intestinal calcium transport activity, and very low ability to mobilize calcium from bone. It also displays relatively high cell differentiation activity, making it potentially useful as an anti-cancer agent or a therapeutic agent for treating skin conditions.
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2-Methylene-18,19-Dinor-1Alpha-Hydroxy-Homopregnacalciferol

UW-Madison researchers have developed a new vitamin D analog, 2-methylene-18,19-dinor-1α-hydroxy-homopregnacalciferol. This compound, a 2-methylene-18,19-dinor vitamin D analog, is characterized by a hydroxyl group at carbon 1, a methylene substituent at carbon 2, a hydrogen at carbon 18 and the elimination of carbons 23,24,25,26 and 27.

Compared to 1α,25-dihydroxyvitamin D3, the new analog exhibits relatively high binding to vitamin D receptors, very low intestinal calcium transport activity, and very low ability to mobilize calcium from bone. It also displays relatively high cell differentiation activity, making it potentially useful as an anti-cancer agent or a therapeutic agent for treating skin conditions.
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Vitamin D Receptor Antagonists for the Treatment of Asthma

UW-Madison researchers have identified several antagonists of the vitamin D receptor that are useful for treating asthma and eczema. The antagonists include various 19-nor 2 alkylidene and 2alpha-alkyl analogs of vitamin D. These compounds interfere with binding between vitamin D and its receptor both in vivo and in vitro.
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Vitamin D Analog for the Treatment of Cancer, Psoriasis and Osteoporosis

UW-Madison researchers have developed a novel vitamin D analog, 2-methylene-19-nor-20(S)-25-methyl-1alpha-hydroxycalciferol. This compound is characterized by relatively high intestinal calcium transport activity and relatively low bone calcium mobilization activity as compared to calcitriol, making it highly specific in its calcemic activity. This compound also exhibits high cell differentiation activity.
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