New vitamin D derivatives with cyclic substructures in the side chains, process and intermediate products for their production, and the use for the production of pharmaceutical agents

• US 20030149006A1
• Filed: 11/26/2002
• Published: 08/07/2003
• Est. Priority Date: 07/23/1999
• Status: Active Grant

• Current Assignee: Andreas Steinmeyer, Claudia Giesen, Katica Schwarz, Marianne Fahnrich, Martin Haberey
• Original Assignee: Andreas Steinmeyer, Claudia Giesen, Katica Schwarz, Marianne Fahnrich, Martin Haberey
• Inventors: Steinmeyer, Andreas, Haberey, Martin, Fahnrich, Marianne, Schwarz, Katica, Giesen, Claudia
• Granted Patent: US 7,115,758 B2
• Time in Patent Office: Days
• US Class Current: 514/167
• CPC Class Codes: A61P 11/00 Drugs for disorders of the respiratory system
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/02 for treating wounds, ulcers, burns, scars, keloids, or the like
• CPC Class Codes: A61P 17/04 Antipruritics
• CPC Class Codes: A61P 17/06 Antipsoriatics
• CPC Class Codes: A61P 17/14 for baldness or alopecia
• CPC Class Codes: A61P 19/00 Drugs for skeletal disorders
• CPC Class Codes: A61P 19/02 for joint disorders, e.g. arthritis, arthrosis
• CPC Class Codes: A61P 19/08 for bone diseases, e.g. rachitism, Paget's disease
• CPC Class Codes: A61P 19/10 for osteoporosis
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/02 for peripheral neuropathies
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 3/00 Drugs for disorders of the metabolism of the blood or the extracellular fluid A61P7/00
• CPC Class Codes: A61P 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 3/14 for calcium homeostasis vitamin D A61P3/02; parathyroid hormones A61P5/18; calcitonin A61P5/22; osteoporosis A61P19/10; bone metastasis A61P35/04
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 37/00 Drugs for immunological or allergic disorders
• CPC Class Codes: A61P 9/10 : for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: B21C 25/02 : Dies
• CPC Class Codes: B21C 25/10 : Making tools by operations not covered by a single other subclass
• CPC Class Codes: C07C 401/00 : Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
• CPC Class Codes: C07D 235/12 : Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 263/32 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 277/24 : Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 307/80 : Radicals substituted by oxygen atoms
• CPC Class Codes: C07D 333/16 : by oxygen atoms
• CPC Class Codes: C07D 333/22 : Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
• CPC Class Codes: Y02P 20/55 : Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention relates to vitamin D derivatives of general formula I,

process for their production, intermediate products of the process as well as the use for the production of pharmaceutical agents.

Claims

1. Vitamin D derivatives of general formula I,

2. Compounds of general formula I according to claim 1, in which

R₃ or R₄ means hydrogen,

X₁ and X₂ together mean a carbonyl group,

or X₁ means a hydroxyl group or a fluorine atom and X₂ means a hydrogen atom

or X₁ means a hydrogen atom and X₂ means a hydroxyl group or a fluorine atom

or X₁ means an —

OC(O)R₅ group and X₂ means a hydrogen atom

or X₁ means a hydrogen atom and X₂ means an —

OC(O)R₅ group, and

X represents an aromatic ring system.

3. Compounds of general formula I according to claim 1,

in which R₃ or R₄ means hydrogen,

X₁ and X₂ together mean a carbonyl group,

or X₁ means a hydroxyl group or a fluorine atom and X₂ means a hydrogen atom

or X₁ means a hydrogen atom and X₂ means a hydroxyl group or a fluorine atom

or X₁ means an —

OC(O)R₅ group and X₂ means a hydrogen atom

or X₁ means a hydrogen atom and X₂ means an —

OC(O)R₅ group, and

Z represents a heteroaromatic ring system.

4. Compounds according to claim 1, in which the stereochemistry in 20-position in the unnatural 20-epi-configuration is present.

5. Vitamin D derivatives of general formula I according to claim 1,

(7E)-(1R,3R,24aR)-24a-(Oxazol-4-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24 as)-24a-(oxazol-4-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(5Z,7E)-(1S,3R,24aR)-24a-(oxazol-4-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24aS)-24a-(oxazol-4-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(7E)-(1R,3R,24aR)-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-(thiazol-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,24aR)-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24aS)-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(7E)-(1R,3R,24aR)-24a-(4-methylthiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(4-methylthiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-(4-methylthiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,24aR)-24a-(4-methylthiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24aS)-24a-(4-methylthiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24a-(4-methylthiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(7E)-(1R,3R,24aR)-24a-(thien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(thien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-(thien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,24aR)-24a-(thien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24aS)-24a-(thien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(7E)-(1R,2S,3R,24aR)-24a-thien-2-yl-24a-homo-19-nor-9,10-secochola-5,7-diene-1,2,3,24-tetrol

(7E)-(1R,2S,3R,24aS)-24a-thien-2-yl-24a-homo-19-nor-9,10-secochola-5,7-diene-1,2,3,24-tetrol

(7E)-(1R,2S,3R)-24a-thien-2-yl-1,2,3-trihydroxy-24a-homo-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,24aR)-24a-(4-methylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(4-methylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-(4-methylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,24aR)-24a-(4-methylthien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24aS)-24a-(4-methylthien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24a-(4-methylthien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(7E)-(1R,2S,3R,24aR)-24a-(4-methylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,2,3,24-tetrol

(7E)-(1R,2S,3R,24aS)-24a-(4-methylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,2,3,24-tetrol

(7E)-(1R,2S,3R)-24a-(4-methylthien-2-yl)-1,2,3-trihydroxy-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,24aR)-24a-(5-ethylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(5-ethylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aR)-24a-[5-(2-hydroxyethyl)-4-methylthiazol-2-yl]-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-[5-(2-hydroxyethyl)-4-methylthiazol-2-yl]-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-[5-(2-hydroxyethyl)-4-methylthiazol-2-yl]-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,24aR)-24a-(benzothiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(benzothiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-24a-(benzothiazol-2-yl)-1,3-dihydroxy-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,24aR)-24a-(benzofuran-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(benzofuran-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-24a-(benzofuran-2-yl)-1,3-dihydroxy-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,24aR)-24a-(benzothiophen-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(benzothiophen-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-24a-(benzothiophen-2-yl)-1,3-dihydroxy-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,24aR)-24a-(1-methylbenzimidazol-2-yl)-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(1-methylbenzimidazol-2-yl)-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-(1-methylbenzimidazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R)-1-(1,3-dihydroxy-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-yl)-3-[(4-methoxyphenyl)-methoxy]-1H-pyrazole-4-carboxylic acid ethyl ester

(7E)-(1R,3R)-1-(1,3-dihydroxy-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-yl)-3-hydroxy-1H-pyrazole-4-carboxylic acid ethyl ester

(7E)-(1R,3R,24aR)-24a-(4-methylphenyl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(4-methylphenyl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-(4-methylphenyl)-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,2R,3R,24aR)-24a-(4-methylphenyl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,2,3,24a-tetrol

(7E)-(1R,RS,3R,24aS)-24a-(4-methylphenyl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,2,3,24a-tetrol

(7E)-(1R,3R,24aR)-24a-(4-trifluoromethylphenyl)-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(4-trifluoromethylphenyl)-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol (7E)-(1R,3R)-1,3-dihydroxy-24a-(4-trifluoromethylphenyl)-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,24aR)-24a-(4-methoxyphenyl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(4-methoxyphenyl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-1,3-dihydroxy-24a-(4-methoxyphenyl)-24a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(7E)-(1R,3R,20S,24aR)-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S,24aS)-24a-(thiazol-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S)-1,3-dihydroxy-24a-(thiazol-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,20S,24aR)-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S,24aS)-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(5Z,7E)-(1S,3R,24S)-24-(thiazol-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R,24R)-24-(thiazol-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(thiazol-2-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(7E)-(1R,3R,20S,24aR)-24a-(oxazol-4-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S,24aS)-24a-(oxazol-4-yl)-24-a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S)-1,3-dihydroxy-24a-(oxazol-4-yl)-24-a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,2,0S,24aR)-24a-(oxazol-4-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S,24aS)-24a-(oxazol-4-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-24a-(oxazol-4-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(5Z,7E)-(1S,3R,24R)-24-(oxazol-4-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24S)-24-(oxazol-4-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(oxazol-4-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(7E)-(1R,3R,20S,24aR)-24a-(4-methylthiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S,24aS)-24a-(4-methylthiazol-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S)-1,3-dihydroxy-24a-(4-methylthiazol-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,20S,24aR)-24a-(4-methylthiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S,24aS)-24a-(4-methylthiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-24a-(4-methylthiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(5Z,7E)-(1S,3R,24R)-24-(4-methylthiazol-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24S)-24-(4-methylthiazol-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(4-methylthiazol-2-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(7E)-(1R,3R,20S,24aR)-24a-(4-methylthien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S,24aS)-24a-(4-methylthien-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S)-1,3-dihydroxy-24a-(4-methylthien-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,20S,24aR)-24a-(4-methylthien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S124aS)-24a-(4-methylthien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-24a-(4-methylthien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(5Z,7E)-(1S,3R,24R)-24-(4-methylthien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24S)-24-(4-methylthien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(4-methylthien-2-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(7E)-(1R,3R,20S,24aR)-24a-(thien-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S,24aS)-24a-(thien-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,20S)-1,3-dihydroxy-24a-(thien-2-yl)-24-a-homo-19-nor-9,10-secochola-5,7-dien-24a-one

(5Z,7E)-(1S,3R,20S,24aR)-24a-(thien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S,24aS)-24a-(thien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,20S)-1,3-dihydroxy-24a-(thien-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-trien-24a-one

(5Z,7E)-(1S,3R,24R)-24-(thien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R,24S)-24-(thien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24a-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(thien-2-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(5Z,7E)-(1S,3R,24S)-24-(4-methylthiazol-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R,24R)-24-(4-methylthiazol-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(4-methylthiazol-2-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(5Z,7E)-(1S,3R,24S)-24-(thien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R,24R)-24-(thien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(thien-2-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(5Z,7E)-(1S,3R,24S)-24-(4-methylthien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R,24R)-24-(4-methylthien-2-yl)-9,10-secochola-5,7,10(19)-triene-1,3,24-triol

(5Z,7E)-(1S,3R)-1,3-dihydroxy-24-(4-methylthien-2-yl)-9,10-secochola-5,7,10(19)-trien-24-one

(7E)-(1R,3R,24aR)-24a-fluoro-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3-diol

(7E)-(1R,3R,24aS)-24a-fluoro-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3-diol

(5Z,7E)-(1S,3R,24aR)-24a-fluoro-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3-diol

(5Z,7E)-(1S,3R,24aS)-24a-fluoro-24a-(thiazol-2-yl)-24a-homo-9,10-secochola-5,7,10(19)-triene-1,3-diol

(7E)-(1R,3R,24aR)-24a-(acetyloxy)-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(acetyloxy)-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aR)-24a-(2,2-dimethylpropanoyloxy)-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R,24aS)-24a-(2,2-dimethylpropanoyloxy)-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol

(7E)-(1R,3R)-2-bromo-24a-(thiazol-2-yl)-24a-homo-19-nor-9,10-secochola-5,7-diene-1,3,24a-triol.

6. Process for the production of compounds of general formula I according to claim 1, in which Q means C₂-C₅ alkyl, characterized in that a compound of formula III

7. Intermediate products of general formulas VIIb

8. Pharmaceutical preparations that contain at least one compound according to claim 1 together with pharmaceutically compatible adjuvants and vehicles.

9. Use of the vitamin D derivatives of general formula I according to claim 1 for the production of pharmaceutical agents.

10. Use according to claim 9 for treating diseases that are characterized by hyperproliferation and deficient cell differentiation (e.g., hyperproliferative diseases of the skin:

psoriasis, pityriasis subia pilasis, acne, ichthyosis;

pruritus;

tumor diseases and precancerous stages;

tumors of the intestines, carcinomas of the breast, lung tumors, prostate carcinomas, leukemias, T-cell lymphomas, melanomas, Betazell carcinoma, squamous carcinoma, actinic keratoses, cervix dysplasias, and metastasizing tumors of any type).

11. Use according to claim 9 for treatment and prophylaxis of diseases that are characterized by a disequilibrium of the immune system (e.g., eczemas and diseases of the atopic Formon series and inflammatory diseases:

rheumatoid arthritis, respiratory tract diseases such as asthma, auto-immune diseases, such as multiple sclerosis, diabetes mellitus type I, myasthenia gravis, lupus erythematosus, scleroderma, bullous skin diseases, such as pemphigus, pemphigoid, further rejection reactions in the case of autologous, allogeneic or xenogeneic transplants, as well as AIDS).

12. Use according to claim 10 in combination with other substances that have an immunosuppressive action, such as cyclosporin A, FK 506, rapamycin and anti-CD4-antibodies.

13. Use according to claim 9 for therapy of secondary hyperparathyroidism and renal osteodystrophia as well as diabetes mellitus type II.

14. Use according to claim 9 for accelerated healing in topical administration as well as for treatment of skin ageing or medicinally induced skin atrophy.

15. Use according to claim 9 for treatment of diseases that accompany disrupted hair growth or for supporting physiological hair growth.

16. Use according to claim 9 for therapy and prophylaxis of senile osteoporosis, postmenopausal osteoporosis, steroid-induced osteoporosis, and for accelerated healing of arthroplasties.

17. Use according to claim 9 for treatment of degenerative diseases of the peripheral and central nervous system.

18. Use of compounds of general formula I, which antagonize the calcitriol action, according to claim 9 for therapy and prophylaxis of arteriosclerosis, for therapy of hypercalcemias, for birth control, in the case of AIDS, as immunostimulants, in hirsutism and granulomatous diseases.

20. Intermediate products of the process according to claim 8 of general formula XXXIVc,

19. Process for the production of compounds of general formula IIa