IL140824A - Calcium Salt of (3S) - Tetrahydro - 3 Fornyl (2R, 1S) - 3 - [[4 - Aminophenyl) Sulfonyl] (Isobutyl) Amino] - 1 - Benzyl - 2 - (Phosphonoxy) propylcarbamate - Google Patents

Calcium Salt of (3S) - Tetrahydro - 3 Fornyl (2R, 1S) - 3 - [[4 - Aminophenyl) Sulfonyl] (Isobutyl) Amino] - 1 - Benzyl - 2 - (Phosphonoxy) propylcarbamate

Info

Publication number: IL140824A
Authority: IL; Israel
Prior art keywords: compound; formula; preparation; calcium; amino
Prior art date: 1998-07-18

Application number

IL14082499A

Other languages

English (en)

Hebrew (he)

Other versions

IL140824A0 (en

Original Assignee

Glaxo Group Ltd

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.)

1998-07-18

Filing date

1999-07-15

Publication date

2004-09-27

1999-07-15 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2002-02-10 Publication of IL140824A0 publication Critical patent/IL140824A0/xx

2004-09-27 Publication of IL140824A publication Critical patent/IL140824A/en

Links

XOGQXKBFJZURRD-HQROKSDRSA-N calcium;[(3s)-oxolan-3-yl] n-[(2s,3r)-4-[(4-aminophenyl)sulfonyl-(2-methylpropyl)amino]-1-phenyl-3-phosphonooxybutan-2-yl]carbamate Chemical compound [Ca].C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 XOGQXKBFJZURRD-HQROKSDRSA-N 0.000 title description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims abstract description 17
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 16
239000011575 calcium Substances 0.000 claims abstract description 13
229910052791 calcium Inorganic materials 0.000 claims abstract description 13
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 12
238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052802 copper Inorganic materials 0.000 claims abstract description 5
239000010949 copper Substances 0.000 claims abstract description 5
239000000843 powder Substances 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 28
239000002904 solvent Substances 0.000 claims description 26
239000011928 denatured alcohol Substances 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 16
YNTOKMNHRPSGFU-UHFFFAOYSA-N n-Propyl carbamate Chemical compound CCCOC(N)=O YNTOKMNHRPSGFU-UHFFFAOYSA-N 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 11
239000007787 solid Substances 0.000 claims description 9
239000000725 suspension Substances 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 7
229910001424 calcium ion Inorganic materials 0.000 claims description 7
239000003638 chemical reducing agent Substances 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
230000000865 phosphorylative effect Effects 0.000 claims description 7
239000001639 calcium acetate Substances 0.000 claims description 6
229960005147 calcium acetate Drugs 0.000 claims description 6
235000011092 calcium acetate Nutrition 0.000 claims description 6
159000000000 sodium salts Chemical class 0.000 claims description 4
208000005074 Retroviridae Infections Diseases 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
238000013160 medical therapy Methods 0.000 claims description 3
238000001816 cooling Methods 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
238000003306 harvesting Methods 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical group [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 description 12
238000009472 formulation Methods 0.000 description 12
239000000243 solution Substances 0.000 description 12
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 11
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 11
229940043265 methyl isobutyl ketone Drugs 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
229960001830 amprenavir Drugs 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
ZMNCIAGFQBUWTJ-OEMFJLHTSA-N [(3s)-oxolan-3-yl] n-[(2s,3r)-3-hydroxy-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenylbutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 ZMNCIAGFQBUWTJ-OEMFJLHTSA-N 0.000 description 9
239000003826 tablet Substances 0.000 description 9
-1 tetrahydro-3-furanyl Chemical group 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
XQKKWWCELHKGKB-UHFFFAOYSA-L calcium acetate monohydrate Chemical compound O.[Ca+2].CC([O-])=O.CC([O-])=O XQKKWWCELHKGKB-UHFFFAOYSA-L 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
239000004030 hiv protease inhibitor Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 5
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
208000030507 AIDS Diseases 0.000 description 4
206010001513 AIDS related complex Diseases 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 description 4
239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
208000031886 HIV Infections Diseases 0.000 description 3
241000725303 Human immunodeficiency virus Species 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
208000036142 Viral infection Diseases 0.000 description 3
230000000840 anti-viral effect Effects 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
239000000920 calcium hydroxide Substances 0.000 description 3
229910001861 calcium hydroxide Inorganic materials 0.000 description 3
XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229940023488 pill Drugs 0.000 description 3
239000006187 pill Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
230000009385 viral infection Effects 0.000 description 3
GWKIPRVERALPRD-ZDUSSCGKSA-N (s)-4-isopropoxycarbonyl-6-methoxy-3-methylthiomethyl-3,4-dihydroquinoxalin-2(1h)-thione Chemical compound N1C(=S)[C@H](CSC)N(C(=O)OC(C)C)C2=CC(OC)=CC=C21 GWKIPRVERALPRD-ZDUSSCGKSA-N 0.000 description 2
208000037357 HIV infectious disease Diseases 0.000 description 2
229940122440 HIV protease inhibitor Drugs 0.000 description 2
241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
102000014961 Protein Precursors Human genes 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 2
YADJFRGSGWGMNH-UHFFFAOYSA-N [chloro(phenylmethoxy)phosphoryl]oxymethylbenzene Chemical compound C=1C=CC=CC=1COP(=O)(Cl)OCC1=CC=CC=C1 YADJFRGSGWGMNH-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
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239000008346 aqueous phase Substances 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
239000002775 capsule Substances 0.000 description 2
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208000033519 human immunodeficiency virus infectious disease Diseases 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
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
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NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
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ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
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239000002244 precipitate Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
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ZHYMGSPDEVXULU-UHFFFAOYSA-N 1,2-benzodiazepin-3-one Chemical class N1=NC(=O)C=CC2=CC=CC=C21 ZHYMGSPDEVXULU-UHFFFAOYSA-N 0.000 description 1
SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical class C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 description 1
HDMHBHNRWDNNCD-UHFFFAOYSA-N 1-[(2-hydroxyethoxy)methyl]-6-(phenylsulfanyl)thymine Chemical compound OCCOCN1C(=O)NC(=O)C(C)=C1SC1=CC=CC=C1 HDMHBHNRWDNNCD-UHFFFAOYSA-N 0.000 description 1
ASOMNDIOOKDVDC-UHFFFAOYSA-N 1h-indol-2-yl-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazin-1-yl]methanone Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=CC=C3C=2)CC1 ASOMNDIOOKDVDC-UHFFFAOYSA-N 0.000 description 1
VDZJXIOFISBBLT-UHFFFAOYSA-N 3-[(4,7-dimethyl-1,3-benzoxazol-2-yl)methylamino]-5-ethyl-6-methyl-1h-pyridin-2-one Chemical compound O=C1NC(C)=C(CC)C=C1NCC1=NC2=C(C)C=CC(C)=C2O1 VDZJXIOFISBBLT-UHFFFAOYSA-N 0.000 description 1
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229920002785 Croscarmellose sodium Polymers 0.000 description 1
BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 1
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WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
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OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 description 1
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HHEVDQQNXOSEBD-OEMFJLHTSA-N [(3s)-oxolan-3-yl] n-[(2s,3r)-4-[2-methylpropyl-(4-nitrophenyl)sulfonylamino]-1-phenyl-3-phosphonooxybutan-2-yl]carbamate Chemical compound C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 HHEVDQQNXOSEBD-OEMFJLHTSA-N 0.000 description 1
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MLBVMOWEQCZNCC-OEMFJLHTSA-N fosamprenavir Chemical compound C([C@@H]([C@H](OP(O)(O)=O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 MLBVMOWEQCZNCC-OEMFJLHTSA-N 0.000 description 1
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238000010965 in-process control Methods 0.000 description 1
229960001936 indinavir Drugs 0.000 description 1
CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
KELNNWMENBUHNS-NSHDSACASA-N isopropyl (2s)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxaline-1(2h)-carboxylate Chemical compound FC1=CC=C2NC(=O)[C@H](CC)N(C(=O)OC(C)C)C2=C1 KELNNWMENBUHNS-NSHDSACASA-N 0.000 description 1
238000011068 loading method Methods 0.000 description 1
CJPLEFFCVDQQFZ-UHFFFAOYSA-N loviride Chemical compound CC(=O)C1=CC=C(C)C=C1NC(C(N)=O)C1=C(Cl)C=CC=C1Cl CJPLEFFCVDQQFZ-UHFFFAOYSA-N 0.000 description 1
229950006243 loviride Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
229960000884 nelfinavir Drugs 0.000 description 1
QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
229960000689 nevirapine Drugs 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000003305 oral gavage Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
150000003252 quinoxalines Chemical class 0.000 description 1
WTTIBCHOELPGFK-LBPRGKRZSA-N r82150 Chemical class C1N(CC=C(C)C)[C@@H](C)CN2C(=S)NC3=CC=CC1=C32 WTTIBCHOELPGFK-LBPRGKRZSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
229960000311 ritonavir Drugs 0.000 description 1
NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
229960001852 saquinavir Drugs 0.000 description 1
QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000015096 spirit Nutrition 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000006068 taste-masking agent Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
230000006514 viral protein processing Effects 0.000 description 1
210000002845 virion Anatomy 0.000 description 1
229960000523 zalcitabine Drugs 0.000 description 1
229960002555 zidovudine Drugs 0.000 description 1
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- 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
- 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
- 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
- A61K31/66—Phosphorus compounds
- A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Virology (AREA)
Molecular Biology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Immunology (AREA)
Biochemistry (AREA)
Epidemiology (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL14082499A 1998-07-18 1999-07-15 Calcium Salt of (3S) - Tetrahydro - 3 Fornyl (2R, 1S) - 3 - [[4 - Aminophenyl) Sulfonyl] (Isobutyl) Amino] - 1 - Benzyl - 2 - (Phosphonoxy) propylcarbamate IL140824A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9815567.4A GB9815567D0 (en)	1998-07-18	1998-07-18	Antiviral compound
PCT/EP1999/004991 WO2000004033A1 (fr)	1998-07-18	1999-07-15	Calcium (3s) tetrahydro-3-furanyle (1s,2r)-3-[[(4-aminophenyle) sulfonyle] (isobutyle) amino]-1-benzyle-2-(phosphonooxy) propylcarbamate

Publications (2)

Publication Number	Publication Date
IL140824A0 IL140824A0 (en)	2002-02-10
IL140824A true IL140824A (en)	2004-09-27

Family

ID=10835689

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL14082499A IL140824A (en)	1998-07-18	1999-07-15	Calcium Salt of (3S) - Tetrahydro - 3 Fornyl (2R, 1S) - 3 - [[4 - Aminophenyl) Sulfonyl] (Isobutyl) Amino] - 1 - Benzyl - 2 - (Phosphonoxy) propylcarbamate

Country Status (47)

Country	Link
US (3)	US6514953B1 (fr)
EP (2)	EP1240903A3 (fr)
JP (1)	JP3437553B2 (fr)
KR (1)	KR100694721B1 (fr)
CN (1)	CN1188422C (fr)
AP (1)	AP2001002039A0 (fr)
AR (1)	AR019388A1 (fr)
AT (1)	ATE229964T1 (fr)
AU (1)	AU766056B2 (fr)
BG (1)	BG105253A (fr)
BR (1)	BRPI9912156B8 (fr)
CA (1)	CA2337857C (fr)
CO (1)	CO5090836A1 (fr)
CZ (1)	CZ300447B6 (fr)
DE (1)	DE69904600T2 (fr)
DK (1)	DK1098898T3 (fr)
DZ (1)	DZ2845A1 (fr)
EA (1)	EA003191B1 (fr)
EE (1)	EE200100038A (fr)
ES (1)	ES2189450T3 (fr)
GB (1)	GB9815567D0 (fr)
GC (1)	GC0000105A (fr)
GE (1)	GEP20033030B (fr)
GT (1)	GT199900111A (fr)
HR (1)	HRP20010046A2 (fr)
HU (1)	HU229700B1 (fr)
ID (1)	ID28070A (fr)
IL (1)	IL140824A (fr)
IS (1)	IS5808A (fr)
JO (1)	JO2114B1 (fr)
MA (1)	MA26660A1 (fr)
MY (1)	MY122323A (fr)
NO (1)	NO329676B1 (fr)
NZ (1)	NZ509291A (fr)
OA (1)	OA11706A (fr)
PA (1)	PA8477801A1 (fr)
PE (1)	PE20000869A1 (fr)
PL (1)	PL195736B1 (fr)
PT (1)	PT1098898E (fr)
SK (1)	SK285311B6 (fr)
SV (1)	SV1999000096A (fr)
TN (1)	TNSN99145A1 (fr)
TR (1)	TR200100111T2 (fr)
TW (1)	TWI245770B (fr)
WO (1)	WO2000004033A1 (fr)
YU (1)	YU3401A (fr)
ZA (1)	ZA200100417B (fr)

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1998
- 1998-07-18 GB GBGB9815567.4A patent/GB9815567D0/en not_active Ceased
1999
- 1999-07-14 DZ DZ990145A patent/DZ2845A1/fr active
- 1999-07-14 GC GCP1999203 patent/GC0000105A/xx active
- 1999-07-14 AR ARP990103446A patent/AR019388A1/es not_active Application Discontinuation
- 1999-07-15 BR BRPI9912156A patent/BRPI9912156B8/pt not_active IP Right Cessation
- 1999-07-15 SV SV1999000096A patent/SV1999000096A/es not_active Application Discontinuation
- 1999-07-15 AU AU50379/99A patent/AU766056B2/en not_active Expired
- 1999-07-15 HU HU0103432A patent/HU229700B1/hu unknown
- 1999-07-15 NZ NZ509291A patent/NZ509291A/en not_active IP Right Cessation
- 1999-07-15 ES ES99934698T patent/ES2189450T3/es not_active Expired - Lifetime
- 1999-07-15 DE DE69904600T patent/DE69904600T2/de not_active Expired - Lifetime
- 1999-07-15 GE GEAP19995716A patent/GEP20033030B/en unknown
- 1999-07-15 HR HR20010046A patent/HRP20010046A2/hr not_active Application Discontinuation
- 1999-07-15 WO PCT/EP1999/004991 patent/WO2000004033A1/fr not_active Ceased
- 1999-07-15 SK SK76-2001A patent/SK285311B6/sk not_active IP Right Cessation
- 1999-07-15 TR TR2001/00111T patent/TR200100111T2/xx unknown
- 1999-07-15 OA OA1200100016A patent/OA11706A/fr unknown
- 1999-07-15 PE PE1999000714A patent/PE20000869A1/es not_active Application Discontinuation
- 1999-07-15 IL IL14082499A patent/IL140824A/en not_active IP Right Cessation
- 1999-07-15 MY MYPI99002983A patent/MY122323A/en unknown
- 1999-07-15 EE EEP200100038A patent/EE200100038A/xx unknown
- 1999-07-15 TN TNTNSN99145A patent/TNSN99145A1/fr unknown
- 1999-07-15 YU YU3401A patent/YU3401A/sh unknown
- 1999-07-15 EP EP02013136A patent/EP1240903A3/fr not_active Withdrawn
- 1999-07-15 EP EP99934698A patent/EP1098898B1/fr not_active Expired - Lifetime
- 1999-07-15 CN CNB998108383A patent/CN1188422C/zh not_active Expired - Lifetime
- 1999-07-15 DK DK99934698T patent/DK1098898T3/da active
- 1999-07-15 US US09/744,051 patent/US6514953B1/en not_active Expired - Lifetime
- 1999-07-15 KR KR1020017000740A patent/KR100694721B1/ko not_active Expired - Lifetime
- 1999-07-15 AP APAP/P/2001/002039A patent/AP2001002039A0/en unknown
- 1999-07-15 EA EA200100053A patent/EA003191B1/ru not_active IP Right Cessation
- 1999-07-15 JP JP2000560139A patent/JP3437553B2/ja not_active Expired - Lifetime
- 1999-07-15 CZ CZ20010219A patent/CZ300447B6/cs not_active IP Right Cessation
- 1999-07-15 MA MA25684A patent/MA26660A1/fr unknown
- 1999-07-15 CA CA2337857A patent/CA2337857C/fr not_active Expired - Lifetime
- 1999-07-15 CO CO99044882A patent/CO5090836A1/es unknown
- 1999-07-15 JO JO19992114A patent/JO2114B1/en active
- 1999-07-15 PT PT99934698T patent/PT1098898E/pt unknown
- 1999-07-15 PL PL99345620A patent/PL195736B1/pl unknown
- 1999-07-15 ID IDW20010145A patent/ID28070A/id unknown
- 1999-07-15 GT GT199900111A patent/GT199900111A/es unknown
- 1999-07-15 AT AT99934698T patent/ATE229964T1/de active
- 1999-07-16 PA PA19998477801A patent/PA8477801A1/es unknown
- 1999-08-06 TW TW088113428A patent/TWI245770B/zh not_active IP Right Cessation
2001
- 2001-01-12 IS IS5808A patent/IS5808A/is unknown
- 2001-01-15 ZA ZA200100417A patent/ZA200100417B/en unknown
- 2001-01-17 NO NO20010282A patent/NO329676B1/no not_active IP Right Cessation
- 2001-02-14 BG BG105253A patent/BG105253A/xx unknown
2002
- 2002-11-25 US US10/303,213 patent/US20030100537A1/en not_active Abandoned
- 2002-11-25 US US10/303,366 patent/US20030096795A1/en not_active Abandoned

Also Published As

Publication number	Publication date
PL345620A1 (en)	2002-01-02
ATE229964T1 (de)	2003-01-15
HK1034261A1 (en)	2001-10-19
DZ2845A1 (fr)	2003-12-01
OA11706A (en)	2005-01-13
CN1324363A (zh)	2001-11-28
BG105253A (en)	2001-12-29
AR019388A1 (es)	2002-02-13
EP1240903A2 (fr)	2002-09-18
PA8477801A1 (es)	2000-05-24
EP1240903A3 (fr)	2003-02-12
HRP20010046A2 (en)	2002-02-28
CZ300447B6 (cs)	2009-05-20
PE20000869A1 (es)	2000-09-08
EP1098898A1 (fr)	2001-05-16
IS5808A (is)	2001-01-12
JP3437553B2 (ja)	2003-08-18
US20030096795A1 (en)	2003-05-22
GC0000105A (en)	2005-06-29
NO20010282L (no)	2001-03-07
PL195736B1 (pl)	2007-10-31
AP2001002039A0 (en)	2001-03-31
DE69904600D1 (de)	2003-01-30
PT1098898E (pt)	2003-04-30
EE200100038A (et)	2002-06-17
ID28070A (id)	2001-05-03
BRPI9912156B8 (pt)	2021-05-25
ZA200100417B (en)	2002-02-27
EA200100053A1 (ru)	2001-08-27
EA003191B1 (ru)	2003-02-27
CA2337857A1 (fr)	2000-01-27
EP1098898B1 (fr)	2002-12-18
MY122323A (en)	2006-04-29
DE69904600T2 (de)	2003-11-13
MA26660A1 (fr)	2004-12-20
CN1188422C (zh)	2005-02-09
HUP0103432A3 (en)	2003-01-28
TNSN99145A1 (fr)	2005-11-10
NZ509291A (en)	2003-05-30
JO2114B1 (en)	2000-05-21
SV1999000096A (es)	2000-07-06
AU766056B2 (en)	2003-10-09
NO329676B1 (no)	2010-11-29
GT199900111A (es)	2001-01-05
ES2189450T3 (es)	2003-07-01
BR9912156A (pt)	2001-04-10
GEP20033030B (en)	2003-07-25
AU5037999A (en)	2000-02-07
TR200100111T2 (tr)	2002-02-21
CA2337857C (fr)	2011-01-25
CO5090836A1 (es)	2001-10-30
WO2000004033A1 (fr)	2000-01-27
YU3401A (sh)	2005-06-10
SK762001A3 (en)	2001-10-08
DK1098898T3 (da)	2003-04-07
KR100694721B1 (ko)	2007-03-15
HU229700B1 (en)	2014-05-28
BRPI9912156B1 (pt)	2016-07-26
US6514953B1 (en)	2003-02-04
HUP0103432A2 (hu)	2002-04-29
KR20010071952A (ko)	2001-07-31
US20030100537A1 (en)	2003-05-29
SK285311B6 (sk)	2006-10-05
NO20010282D0 (no)	2001-01-17
GB9815567D0 (en)	1998-09-16
IL140824A0 (en)	2002-02-10
CZ2001219A3 (cs)	2001-07-11
JP2003521447A (ja)	2003-07-15
TWI245770B (en)	2005-12-21

Legal Events

Date	Code	Title
2005-02-20	FF	Patent granted
2005-03-20	KB	Patent renewed
2005-09-25	KB	Patent renewed
2010-02-14	KB	Patent renewed
2013-07-31	KB	Patent renewed
2017-06-29	KB	Patent renewed
2020-02-27	EXP	Patent expired

Publication	Publication Date	Title
EP1098898B1 (fr)	2002-12-18	Calcium (3s) tetrahydro-3-furanyle (1s,2r)-3-[[(4-aminophenyle) sulfonyle] (isobutyle) amino]-1-benzyle-2-(phosphonooxy) propylcarbamate
EA020489B1 (ru)	2014-11-28	Модуляторы фармакокинетических свойств лекарственных средств
NO326265B1 (no)	2008-10-27	Sulfonamid-derivater som medisinforloper av aspartylproteaseinhibitorer
PL204458B1 (pl)	2010-01-29	Pochodne fosforanowe (1R,cis)-4-(6-amino-9H-puryn-9-ylo)-2-cyklopenteno-1-metanolu, kompozycje zawierające te związki, sposób wytwarzania tych związków oraz ich zastosowanie
EP0350012A2 (fr)	1990-01-10	Composition antivirale
WO2021257569A1 (fr)	2021-12-23	Composés antiviraux et leurs procédés d'utilisation
WO2001000635A2 (fr)	2001-01-04	Derives de (3s) tetrahydro-3-furanyl (1s,2r)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-(phosphono-oxy)propylcarbamate
HK87696A (en)	1996-05-24	Indolyl propanols, process for their preparation, their uses and preparation containing them
US20060134190A1 (en)	2006-06-22	Formulations of bisphosphonate drugs with improved bioavailability
HK1034261B (en)	2003-07-25	Calcium (3s) tetrahydro-3-furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl] (isobutyl) amino] -1-benzyl-2- (phosphonooxy) propylcarbamate
MXPA01000617A (en)	2001-12-04	Calcium (3s) tetrahydro-3- furanyl(1s,2r)-3-[[(4-aminophenyl) sulfonyl](isobutyl) amino]-1-benzyl-2- (phosphonooxy) propylcarbamate
RU2256451C1 (ru)	2005-07-20	Лекарственное средство для лечения атипичной пневмонии
HRP980264A2 (en)	1999-02-28	Antiviral combinations
WO1998056781A1 (fr)	1998-12-17	Forme v d'amprenavir (vx-478) en tant que compose antiviral
DK200200115U3 (da)	2002-06-28	Hidtil ukendte salte af 4-amino-1-hydroxybutyliden-1, 1-bisphosphonsyre, deres fremstilling og anvendelse
JPH05279253A (ja)	1993-10-26	骨粗鬆症予防および治療剤