NL8005064A - Cholecalciferolderivaten. - Google Patents

Cholecalciferolderivaten. Download PDF

Info

Publication number: NL8005064A
Authority: NL; Netherlands
Prior art keywords: formula; carbon atoms; small number; compound; groups
Prior art date: 1979-09-14

Application number

NL8005064A

Other languages

English (en)

Dutch (nl)

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1979-09-14

Filing date

1980-09-08

Publication date

1981-03-17

1980-09-08 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1981-03-17 Publication of NL8005064A publication Critical patent/NL8005064A/nl

Links

150000003704 vitamin D3 derivatives Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 50
125000004432 carbon atom Chemical group C* 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 18
238000000034 method Methods 0.000 claims description 13
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
239000011575 calcium Substances 0.000 claims description 6
229910052791 calcium Inorganic materials 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
ZGDVRBVTNMQMEX-LDHZKLTISA-N (8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylhept-6-en-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)=C)C)[C@@]1(C)CC2 ZGDVRBVTNMQMEX-LDHZKLTISA-N 0.000 claims 2
230000001105 regulatory effect Effects 0.000 claims 2
150000003702 vitamin D1 derivatives Chemical class 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
-1 methoxymethoxy group Chemical group 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
238000006317 isomerization reaction Methods 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
239000002207 metabolite Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
QOWCBCXATJITSI-ZLNGONTQSA-N (6r)-6-[(1r,3as,4e,7ar)-4-[(2z)-2-[(5s)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-1-yl]-2-methylheptane-1,2-diol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(O)CO)C)=C\C=C1\C[C@@H](O)CCC1=C QOWCBCXATJITSI-ZLNGONTQSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
ICGLPKIVTVWCFT-UHFFFAOYSA-N 4-methylbenzenesulfonohydrazide Chemical compound CC1=CC=C(S(=O)(=O)NN)C=C1 ICGLPKIVTVWCFT-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930003316 Vitamin D Natural products 0.000 description 1
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 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
229910001516 alkali metal iodide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
LSMAIBOZUPTNBR-UHFFFAOYSA-N phosphanium;iodide Chemical compound [PH4+].[I-] LSMAIBOZUPTNBR-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000009991 scouring Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
- 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
- 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
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Obesity (AREA)
Hematology (AREA)
Molecular Biology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Biochemistry (AREA)
Reproductive Health (AREA)
Nutrition Science (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL8005064A 1979-09-14 1980-09-08 Cholecalciferolderivaten. NL8005064A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH834679A CH644100A5 (de)	1979-09-14	1979-09-14	Cholecalciferolderivate.
CH834679		1979-09-14

Publications (1)

Publication Number	Publication Date
NL8005064A true NL8005064A (nl)	1981-03-17

Family

ID=4338917

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8005064A NL8005064A (nl)	1979-09-14	1980-09-08	Cholecalciferolderivaten.

Country Status (10)

Country	Link
US (1)	US4407754A (it)
JP (1)	JPS5651447A (it)
AT (1)	AT372943B (it)
BE (1)	BE885204A (it)
CH (1)	CH644100A5 (it)
DE (1)	DE3034722A1 (it)
FR (1)	FR2468587A1 (it)
GB (1)	GB2060642B (it)
IT (1)	IT1131777B (it)
NL (1)	NL8005064A (it)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0086350A3 (de) *	1982-02-12	1984-11-28	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Verfahren zur Herstellung von Cholesterinderivaten
CA1206882A (en) *	1982-02-12	1986-07-02	Hoffmann-La Roche Limited	Use of cholecalciferol derivatives
US4617297A (en) *	1982-02-12	1986-10-14	Hoffmann-La Roche Inc.	Method of treating disease states by the administration of 1α,25,26-trihydroxycholecalciferol
US5120722A (en) *	1984-02-08	1992-06-09	Hoffmann-La Roche Inc.	Trihydroxy-cholecacliferol and trihydroxy-ergocalciferol for treating leukemia
WO1990000560A1 (fr) *	1988-07-05	1990-01-25	Kuraray Co., Ltd.	Composes steroidiques
CN101381389B (zh) *	2008-09-29	2011-05-25	浙江工业大学	5,7-双烯甾类化合物的化学合成方法

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US3739001A (en) *	1971-10-22	1973-06-12	Wisconsin Alumni Res Found	25,26-dihydroxycholecalciferol
US4204995A (en) *	1978-03-15	1980-05-27	Hoffmann-La Roche Inc.	Cholestane derivatives
EP0019059B1 (de) *	1979-05-18	1982-12-29	F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft	Verfahren zur Herstellung von Cholestenderivaten und neue Zwischenprodukte in deren Herstellung
US4265822A (en) *	1979-09-10	1981-05-05	Wisconsin Alumni Research Foundation	Process for preparing 1-hydroxylated vitamin D compounds from 5,6-trans-vitamin D compounds

1979
- 1979-09-14 CH CH834679A patent/CH644100A5/de not_active IP Right Cessation
1980
- 1980-07-28 IT IT23753/80A patent/IT1131777B/it active
- 1980-09-08 NL NL8005064A patent/NL8005064A/nl not_active Application Discontinuation
- 1980-09-11 JP JP12537280A patent/JPS5651447A/ja active Granted
- 1980-09-12 AT AT0459980A patent/AT372943B/de not_active IP Right Cessation
- 1980-09-12 BE BE0/202077A patent/BE885204A/fr not_active IP Right Cessation
- 1980-09-12 GB GB8029544A patent/GB2060642B/en not_active Expired
- 1980-09-12 FR FR8019721A patent/FR2468587A1/fr active Granted
- 1980-09-15 DE DE19803034722 patent/DE3034722A1/de not_active Ceased
1982
- 1982-03-12 US US06/357,438 patent/US4407754A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CH644100A5 (de)	1984-07-13
DE3034722A1 (de)	1981-04-02
AT372943B (de)	1983-11-25
JPS5651447A (en)	1981-05-09
GB2060642A (en)	1981-05-07
FR2468587B1 (it)	1984-10-19
FR2468587A1 (fr)	1981-05-08
GB2060642B (en)	1983-11-30
IT8023753A0 (it)	1980-07-28
IT1131777B (it)	1986-06-25
BE885204A (fr)	1981-03-12
US4407754A (en)	1983-10-04
ATA459980A (de)	1983-04-15
JPH0144695B2 (it)	1989-09-29

Publication	Publication Date	Title
Bartlett et al.	1983	Asymmetric synthesis via acetal templates. 3. On the stereochemistry observed in the cyclization of chiral acetals of polyolefinic aldehydes; formation of optically active homoallylic alcohols
US4129564A (en)	1978-12-12	Spirolactones
JP3494637B2 (ja)	2004-02-09	１９−ノル−ビタミンｄ化合物の中間体の製造方法
Wadsworth et al.	1987	Preparation of arylpropiolate esters from trichlorocyclopropenium cation and elaboration of the esters to unsymmetrical 1, 4-pentadiyn-3-ones and unsymmetrical tellurapyranones
Pelter et al.	1987	Synthetic routes to the piperolides, fadyenolides, epoxypiperolides, and related compounds
CA1079725A (en)	1980-06-17	Prostaglandin-acetylene analogues and process for their manufacture
LV10428B (en)	1995-10-20	Novel vitamin d analogues
US5719297A (en)	1998-02-17	Vitamin D3 derivatives and production process thereof
KR20010030966A (ko)	2001-04-16	신규한 비타민 ｄ 동족체
EP0579769B1 (en)	1998-10-21	2- and 5-alkyl and phenyl substituted 4-(1-hydroxy, 1-acyloxy or 1-carbamoyloxy)-5-hydroxy-2(5h)-furanones as anti-inflammatory agents
PT97256A (pt)	1992-01-31	Processo para a preparacao de derivados de 24-oxa na serie da vitamina d e de composicoes farmaceuticas que os contem
US4102888A (en)	1978-07-25	3-Thiazolidinyl heptanoic acids
NL8005064A (nl)	1981-03-17	Cholecalciferolderivaten.
Nakamura et al.	1987	Syntheses of bis (vinylenedithio) tetrathiafulvalene and bis (methylvinylenedithio) tetrathiafulvalene.
JP2009256361A (ja)	2009-11-05	２４−ヒドロキシビタミンｄ誘導体
DK145083B (da)	1982-08-23	Prostaglandin-analoge til anvendelse i midler til regulering af den reproduktive cyclos hos raske pattedyr
EP0106576B1 (en)	1988-03-09	Novel 5-membered cyclic compounds, process for the production thereof, and pharmaceutical use thereof
GB1564809A (en)	1980-04-16	24,25-epoxy-cholestane derivatives
JPH05501718A (ja)	1993-04-02	側鎖同族体ビタミン―ｄ―誘導体、その製造法ならびに該誘導体を含有する、過増殖を示す疾病を治療するための製薬学的調製剤
EP0180399B1 (en)	1992-05-20	Anti-tumor 4-hydroxy-2-cyclopentenones
AU615534B2 (en)	1991-10-03	2-substituted-2-cyclopentenones
US4871762A (en)	1989-10-03	Lipid peroxide lowering 1,3-benzoxathiole derivative compositions and method of use therefor
US4038272A (en)	1977-07-26	Stereospecific syntheses of 24r,25- and 24s,25-dihydroxycholesterol and alkanoyl derivatives thereof
US4338332A (en)	1982-07-06	Fluoro-prostaglandins
US4258199A (en)	1981-03-24	Method for preparing cyclic ethers and thioethers including oxygen isomers and sulfur analogs of prostacyclin

Legal Events

Date	Code	Title	Description
1981-07-01	BT	A notification was added to the application dossier and made available to the public
1985-01-01	A85	Still pending on 85-01-01
1987-11-02	BA	A request for search or an international-type search has been filed
1988-03-01	BB	A search report has been drawn up
1988-07-01	BC	A request for examination has been filed
1990-01-16	CNR	Transfer of rights (patent application after its laying open for public inspection)	Free format text: HOFFMANN-LA ROCHE AG. F. -
1993-05-03	BV	The patent application has lapsed