NO971217L - Dihydroksy-trisdehydro-kolekalsiferolderivater - Google Patents

Dihydroksy-trisdehydro-kolekalsiferolderivater

Info

Publication number: NO971217L
Authority: NO; Norway
Prior art keywords: formula; lower alkyl; compound; diseases; aryl
Prior art date: 1996-03-21

Application number

NO971217A

Other languages

English (en)

Norwegian (no)

Other versions

NO971217D0 (no

Inventor

Bernard Michael Hennessy

Jerome Anthony Iacobelli

Milan Radoje Uskokovic

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.)

1996-03-21

Filing date

1997-03-17

Publication date

1997-09-22

1997-03-17 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1997-03-17 Publication of NO971217D0 publication Critical patent/NO971217D0/no

1997-09-22 Publication of NO971217L publication Critical patent/NO971217L/no

Links

150000001875 compounds Chemical class 0.000 claims description 103
239000000203 mixture Substances 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 15
208000002874 Acne Vulgaris Diseases 0.000 claims description 8
208000015390 Sebaceous gland disease Diseases 0.000 claims description 8
206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 8
206010000496 acne Diseases 0.000 claims description 8
230000003463 hyperproliferative effect Effects 0.000 claims description 8
230000005764 inhibitory process Effects 0.000 claims description 8
208000008742 seborrheic dermatitis Diseases 0.000 claims description 8
208000017520 skin disease Diseases 0.000 claims description 8
201000004681 Psoriasis Diseases 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
230000001613 neoplastic effect Effects 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 6
239000000543 intermediate Substances 0.000 claims description 6
208000032839 leukemia Diseases 0.000 claims description 6
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
210000004881 tumor cell Anatomy 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
150000002221 fluorine Chemical class 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 2
150000002009 diols Chemical class 0.000 claims description 2
238000009472 formulation Methods 0.000 claims description 2
239000003495 polar organic solvent Substances 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
210000004027 cell Anatomy 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000012267 brine Substances 0.000 description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
238000012360 testing method Methods 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
239000012043 crude product Substances 0.000 description 8
108091003079 Bovine Serum Albumin Proteins 0.000 description 6
239000012894 fetal calf serum Substances 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000010410 layer Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
210000001744 T-lymphocyte Anatomy 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
239000000499 gel Substances 0.000 description 5
239000002609 medium Substances 0.000 description 5
JPXMTWWFLBLUCD-UHFFFAOYSA-N nitro blue tetrazolium(2+) Chemical compound COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 JPXMTWWFLBLUCD-UHFFFAOYSA-N 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
210000003491 skin Anatomy 0.000 description 5
239000006208 topical dosage form Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000002585 base Substances 0.000 description 4
239000006285 cell suspension Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
210000000987 immune system Anatomy 0.000 description 4
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 4
239000011736 potassium bicarbonate Substances 0.000 description 4
235000015497 potassium bicarbonate Nutrition 0.000 description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
230000035755 proliferation Effects 0.000 description 4
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
-1 trialkylsilyl chloride Chemical compound 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
108010047620 Phytohemagglutinins Proteins 0.000 description 3
239000012980 RPMI-1640 medium Substances 0.000 description 3
206010052779 Transplant rejections Diseases 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000004069 differentiation Effects 0.000 description 3
JGHYBJVUQGTEEB-UHFFFAOYSA-M dimethylalumanylium;chloride Chemical compound C[Al](C)Cl JGHYBJVUQGTEEB-UHFFFAOYSA-M 0.000 description 3
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000012259 ether extract Substances 0.000 description 3
208000024908 graft versus host disease Diseases 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000006186 oral dosage form Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 3
239000002953 phosphate buffered saline Substances 0.000 description 3
230000001885 phytohemagglutinin Effects 0.000 description 3
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000011550 stock solution Substances 0.000 description 3
229940104230 thymidine Drugs 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000167854 Bourreria succulenta Species 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
229930182816 L-glutamine Natural products 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
241001465754 Metazoa Species 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
239000012979 RPMI medium Substances 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
230000006052 T cell proliferation Effects 0.000 description 2
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000004663 cell proliferation Effects 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
235000019693 cherries Nutrition 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000006071 cream Substances 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
210000002950 fibroblast Anatomy 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
239000012737 fresh medium Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
230000006698 induction Effects 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
210000002510 keratinocyte Anatomy 0.000 description 2
210000000265 leukocyte Anatomy 0.000 description 2
239000006210 lotion Substances 0.000 description 2
210000004698 lymphocyte Anatomy 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
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
210000005087 mononuclear cell Anatomy 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002674 ointment Substances 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 2
229940074439 potassium sodium tartrate Drugs 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
238000000746 purification Methods 0.000 description 2
210000004378 sebocyte Anatomy 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000011006 sodium potassium tartrate Nutrition 0.000 description 2
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
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239000005720 sucrose Substances 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 2
238000010998 test method Methods 0.000 description 2
GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 description 1
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CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
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YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
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125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Engineering & Computer Science (AREA)
Oncology (AREA)
Hematology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Liquid Crystal Substances (AREA)
Furan Compounds (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

NO971217A 1996-03-21 1997-03-17 Dihydroksy-trisdehydro-kolekalsiferolderivater NO971217L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US1380996P	1996-03-21	1996-03-21

Publications (2)

Publication Number	Publication Date
NO971217D0 NO971217D0 (no)	1997-03-17
NO971217L true NO971217L (no)	1997-09-22

Family

ID=21761865

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO971217A NO971217L (no)	1996-03-21	1997-03-17	Dihydroksy-trisdehydro-kolekalsiferolderivater

Country Status (30)

Country	Link
EP (1)	EP0796843B1 (cs)
JP (1)	JP2801587B2 (cs)
KR (1)	KR100240541B1 (cs)
CN (1)	CN1110477C (cs)
AR (1)	AR006315A1 (cs)
AT (1)	ATE240941T1 (cs)
AU (1)	AU708679B2 (cs)
BR (1)	BR9701404A (cs)
CA (1)	CA2199893C (cs)
CO (1)	CO4820396A1 (cs)
CZ (1)	CZ85897A3 (cs)
DE (1)	DE69722064T2 (cs)
DK (1)	DK0796843T3 (cs)
ES (1)	ES2198512T3 (cs)
HR (1)	HRP970162A2 (cs)
HU (1)	HUP9700609A3 (cs)
ID (1)	ID16285A (cs)
IL (1)	IL120469A0 (cs)
MA (1)	MA26423A1 (cs)
MX (1)	MX9702139A (cs)
NO (1)	NO971217L (cs)
NZ (1)	NZ314424A (cs)
PE (1)	PE42998A1 (cs)
PL (1)	PL319070A1 (cs)
PT (1)	PT796843E (cs)
SG (1)	SG70589A1 (cs)
TR (1)	TR199700219A2 (cs)
TW (1)	TW444001B (cs)
YU (1)	YU10397A (cs)
ZA (1)	ZA972302B (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9625271D0 (en) *	1996-12-04	1997-01-22	Leo Pharm Prod Ltd	Chemical compounds
US6331642B1 (en) *	1999-07-12	2001-12-18	Hoffmann-La Roche Inc.	Vitamin D3 analogs
KR101285720B1 (ko) *	2012-03-02	2013-07-19	주식회사 유니크메디케어	여드름 개선용 조성물
KR102493627B1 (ko)	2015-11-26	2023-01-31	코웨이 주식회사	호르데닌을 유효성분으로 함유하는 피부암 예방 또는 치료용 약학 조성물

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA8923B (en) *	1988-01-20	1989-09-27	Hoffmann La Roche	16-dehydro-vitamin d3-derivatives
DE69005897D1 (de) *	1989-05-18	1994-02-24	Hoffmann La Roche	Dehydrocholecalciferolderivate.

1997
- 1997-03-06 AU AU15135/97A patent/AU708679B2/en not_active Ceased
- 1997-03-11 SG SG1997000771A patent/SG70589A1/en unknown
- 1997-03-12 PE PE1997000190A patent/PE42998A1/es not_active Application Discontinuation
- 1997-03-13 TW TW086103109A patent/TW444001B/zh active
- 1997-03-13 CA CA002199893A patent/CA2199893C/en not_active Expired - Fee Related
- 1997-03-14 PT PT97104387T patent/PT796843E/pt unknown
- 1997-03-14 ES ES97104387T patent/ES2198512T3/es not_active Expired - Lifetime
- 1997-03-14 DE DE69722064T patent/DE69722064T2/de not_active Expired - Fee Related
- 1997-03-14 EP EP97104387A patent/EP0796843B1/en not_active Expired - Lifetime
- 1997-03-14 AT AT97104387T patent/ATE240941T1/de not_active IP Right Cessation
- 1997-03-14 DK DK97104387T patent/DK0796843T3/da active
- 1997-03-17 IL IL12046997A patent/IL120469A0/xx unknown
- 1997-03-17 NZ NZ314424A patent/NZ314424A/en unknown
- 1997-03-17 ZA ZA9702302A patent/ZA972302B/xx unknown
- 1997-03-17 NO NO971217A patent/NO971217L/no not_active Application Discontinuation
- 1997-03-18 JP JP9064030A patent/JP2801587B2/ja not_active Expired - Fee Related
- 1997-03-19 YU YU10397A patent/YU10397A/sh unknown
- 1997-03-19 ID IDP970894A patent/ID16285A/id unknown
- 1997-03-19 HU HU9700609A patent/HUP9700609A3/hu unknown
- 1997-03-19 HR HR60/013,809A patent/HRP970162A2/xx not_active Application Discontinuation
- 1997-03-19 AR ARP970101091A patent/AR006315A1/es not_active Application Discontinuation
- 1997-03-20 KR KR1019970009478A patent/KR100240541B1/ko not_active Expired - Fee Related
- 1997-03-20 CO CO97015089A patent/CO4820396A1/es unknown
- 1997-03-20 BR BR9701404A patent/BR9701404A/pt not_active IP Right Cessation
- 1997-03-20 CN CN97103358A patent/CN1110477C/zh not_active Expired - Fee Related
- 1997-03-20 TR TR97/00219A patent/TR199700219A2/xx unknown
- 1997-03-20 CZ CZ97858A patent/CZ85897A3/cs unknown
- 1997-03-20 MX MX9702139A patent/MX9702139A/es not_active IP Right Cessation
- 1997-03-20 PL PL97319070A patent/PL319070A1/xx unknown
- 1997-03-21 MA MA24528A patent/MA26423A1/fr unknown

Also Published As

Publication number	Publication date
CA2199893C (en)	2008-02-05
PE42998A1 (es)	1998-08-11
DK0796843T3 (da)	2003-09-15
CN1172793A (zh)	1998-02-11
EP0796843A3 (en)	1999-04-14
DE69722064D1 (de)	2003-06-26
DE69722064T2 (de)	2004-04-08
HU9700609D0 (en)	1997-05-28
ZA972302B (en)	1997-09-22
HUP9700609A3 (en)	1999-03-01
KR100240541B1 (ko)	2000-01-15
CO4820396A1 (es)	1999-07-28
TR199700219A3 (tr)	1997-10-21
HRP970162A2 (en)	1998-04-30
MA26423A1 (fr)	2004-12-20
PT796843E (pt)	2003-09-30
TR199700219A2 (xx)	1997-10-21
ID16285A (id)	1997-09-18
CZ85897A3 (cs)	1998-04-15
MX9702139A (es)	1998-04-30
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