DD297824A5 - N-substituierte aminoalkandiphosphonsaeuren - Google Patents
N-substituierte aminoalkandiphosphonsaeuren Download PDFInfo
- Publication number
- DD297824A5 DD297824A5 DD90338447A DD33844790A DD297824A5 DD 297824 A5 DD297824 A5 DD 297824A5 DD 90338447 A DD90338447 A DD 90338447A DD 33844790 A DD33844790 A DD 33844790A DD 297824 A5 DD297824 A5 DD 297824A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- hydroxy
- salt
- alk
- amino
- formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 12
- 150000007513 acids Chemical class 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 129
- 150000001875 compounds Chemical class 0.000 claims abstract description 126
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 230000000865 phosphorylative effect Effects 0.000 claims abstract description 5
- -1 carboxy, carbamyl Chemical group 0.000 claims description 153
- 238000000034 method Methods 0.000 claims description 58
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 21
- 229910014033 C-OH Inorganic materials 0.000 claims description 20
- 229910014570 C—OH Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 17
- 239000005977 Ethylene Substances 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 10
- 229910052727 yttrium Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- ASMGFLAYDQSOPU-UHFFFAOYSA-N hydroxy-[1-hydroxy-3-[methyl(3-phenoxypropyl)azaniumyl]-1-phosphonopropyl]phosphinate Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCCOC1=CC=CC=C1 ASMGFLAYDQSOPU-UHFFFAOYSA-N 0.000 claims description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- UNIREAWRNZTCNK-UHFFFAOYSA-N [1-hydroxy-3-[2-(4-methoxyphenoxy)ethylamino]-1-phosphonopropyl]phosphonic acid Chemical compound COC1=CC=C(OCCNCCC(O)(P(O)(O)=O)P(O)(O)=O)C=C1 UNIREAWRNZTCNK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 claims description 2
- VKCKEACFQGUUMQ-UHFFFAOYSA-N [1-hydroxy-3-[methyl-[3-(3-methylphenoxy)propyl]amino]-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCCOC1=CC=CC(C)=C1 VKCKEACFQGUUMQ-UHFFFAOYSA-N 0.000 claims description 2
- TZRQLNHNYFPOGE-UHFFFAOYSA-N [1-hydroxy-3-[2-(2-hydroxyphenoxy)ethyl-methylamino]-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCOC1=CC=CC=C1O TZRQLNHNYFPOGE-UHFFFAOYSA-N 0.000 claims 2
- NMVTUWIKAHUBPG-UHFFFAOYSA-N [1-hydroxy-3-[methyl(3-pyrimidin-2-ylpropyl)amino]-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCCC1=NC=CC=N1 NMVTUWIKAHUBPG-UHFFFAOYSA-N 0.000 claims 2
- BLVFIODMGHEXHI-UHFFFAOYSA-N [1-hydroxy-3-[methyl-[3-(pyridin-2-ylamino)propyl]amino]-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCCNC1=CC=CC=N1 BLVFIODMGHEXHI-UHFFFAOYSA-N 0.000 claims 2
- STPLISLRBATLKY-UHFFFAOYSA-N [3-[3-(4-fluorophenoxy)propyl-methylamino]-1-hydroxy-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCCOC1=CC=C(F)C=C1 STPLISLRBATLKY-UHFFFAOYSA-N 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 claims 2
- KZFMRKCPGOONMR-UHFFFAOYSA-N [1-hydroxy-3-(3-phenoxypropylamino)-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CCNCCCOC1=CC=CC=C1 KZFMRKCPGOONMR-UHFFFAOYSA-N 0.000 claims 1
- ZUEWACIUWCRHMM-UHFFFAOYSA-N [1-hydroxy-3-[3-(4-methoxyphenoxy)propyl-methylamino]-1-phosphonopropyl]phosphonic acid Chemical compound COC1=CC=C(OCCCN(C)CCC(O)(P(O)(O)=O)P(O)(O)=O)C=C1 ZUEWACIUWCRHMM-UHFFFAOYSA-N 0.000 claims 1
- ZEQNCEOOAYAQEG-UHFFFAOYSA-N [1-hydroxy-3-[methyl(2-phenoxyethyl)amino]-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCOC1=CC=CC=C1 ZEQNCEOOAYAQEG-UHFFFAOYSA-N 0.000 claims 1
- YCHQUCXDXRXKBE-UHFFFAOYSA-N [1-hydroxy-3-[methyl(4-phenylsulfanylbutyl)amino]-1-phosphonopropyl]phosphonic acid Chemical compound C1(=CC=CC=C1)SCCCCN(C)CCC(P(O)(=O)O)(P(O)(=O)O)O YCHQUCXDXRXKBE-UHFFFAOYSA-N 0.000 claims 1
- PUABCAYSGXVGFC-UHFFFAOYSA-N [1-hydroxy-3-[methyl-[2-[3-(trifluoromethyl)anilino]ethyl]amino]-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCNC1=CC=CC(C(F)(F)F)=C1 PUABCAYSGXVGFC-UHFFFAOYSA-N 0.000 claims 1
- DCILPIGCJYXCSD-UHFFFAOYSA-N [3-[2-(4-chlorophenoxy)ethyl-methylamino]-1-hydroxy-1-phosphonopropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)(P(O)(O)=O)CCN(C)CCOC1=CC=C(Cl)C=C1 DCILPIGCJYXCSD-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 230000003913 calcium metabolism Effects 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 abstract 1
- 125000004149 thio group Chemical group *S* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 150000002148 esters Chemical group 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001340 alkali metals Chemical class 0.000 description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 6
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000037147 Hypercalcaemia Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
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- 229920002472 Starch Polymers 0.000 description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 125000005277 alkyl imino group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
- 230000000148 hypercalcaemia Effects 0.000 description 3
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- XHAZMZWXAOBLQG-UHFFFAOYSA-N (1-hydroxy-1-phosphonopropyl)phosphonic acid Chemical compound CCC(O)(P(O)(O)=O)P(O)(O)=O XHAZMZWXAOBLQG-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
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- 229920001800 Shellac Polymers 0.000 description 2
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical group C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound 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-YRZJJWOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003751 zinc Chemical class 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH86689 | 1989-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD297824A5 true DD297824A5 (de) | 1992-01-23 |
Family
ID=4197009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD90338447A DD297824A5 (de) | 1989-03-08 | 1990-03-06 | N-substituierte aminoalkandiphosphonsaeuren |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5036058A (fi) |
| EP (1) | EP0387194B1 (fi) |
| JP (1) | JPH02279689A (fi) |
| KR (1) | KR900014413A (fi) |
| AT (1) | ATE117308T1 (fi) |
| AU (1) | AU629298B2 (fi) |
| CA (1) | CA2011586A1 (fi) |
| DD (1) | DD297824A5 (fi) |
| DE (1) | DE59008275D1 (fi) |
| DK (1) | DK0387194T3 (fi) |
| ES (1) | ES2067010T3 (fi) |
| FI (1) | FI95264C (fi) |
| HU (1) | HU206120B (fi) |
| IE (1) | IE64984B1 (fi) |
| IL (1) | IL93586A (fi) |
| MX (1) | MX19785A (fi) |
| NO (1) | NO174152C (fi) |
| NZ (1) | NZ232805A (fi) |
| PH (1) | PH26923A (fi) |
| PT (1) | PT93353B (fi) |
| ZA (1) | ZA901742B (fi) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4015715A1 (de) * | 1990-05-16 | 1991-11-21 | Bayer Ag | Neuartige oligophosphate mit antiviraler wirkung |
| IE912115A1 (en) * | 1990-06-25 | 1992-01-01 | Takeda Chemical Industries Ltd | Bisphosphonic acid derivatives, their production and use |
| US5159108A (en) * | 1990-09-18 | 1992-10-27 | Merck & Co., Inc. | Process for preparing an antihypercalcemic agent |
| CA2058012A1 (en) * | 1990-12-19 | 1992-06-20 | Takashi Sohda | Bisphosphonic acid derivatives, their production and use |
| IT1244698B (it) * | 1991-02-01 | 1994-08-08 | Gentili Ist Spa | Acidi aril-o arilalchil-acil ammino-alchil-idrossidifosfonici, procedimento per la loro preparazione e loro uso in terapia osteo-articolare e dei tessuti connettori in generale |
| ES2096061T3 (es) * | 1991-08-27 | 1997-03-01 | Ciba Geigy Ag | Acidos aminometanodifosfonicos n-substituidos. |
| EP0541037A3 (en) * | 1991-11-06 | 1997-02-26 | Takeda Chemical Industries Ltd | Squalene synthetase inhibitory composition and use thereof |
| US5283057A (en) * | 1992-04-24 | 1994-02-01 | The Procter & Gamble Company | Risedronate in oral compositions |
| JP2006176499A (ja) * | 2004-11-25 | 2006-07-06 | Nippon Seibutsu Seizai:Kk | 眼疾患治療剤 |
| FR2926081B1 (fr) * | 2008-01-03 | 2010-02-19 | Univ Nantes | Derives d'acide hydroxy-bisphosphonique comme vecteur ciblant le tissu osseux |
| FR2973378B1 (fr) | 2011-03-28 | 2013-10-04 | Atlanthera | Derives d'acide hydroxybisphosphonique bifonctionnels |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3203308A1 (de) * | 1982-01-27 | 1983-07-28 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diphosphonsaeure-derivate und diese enthaltende pharmazeutische praeparate |
| FR2531088B1 (fr) * | 1982-07-29 | 1987-08-28 | Sanofi Sa | Produits anti-inflammatoires derives de l'acide methylenediphosphonique et leur procede de preparation |
| GB8419489D0 (en) * | 1984-07-31 | 1984-09-05 | Leo Pharm Prod Ltd | Chemical compounds |
| US4639338A (en) * | 1984-08-06 | 1987-01-27 | Ciba-Geigy Corporation | Preparation of crystalline disodium 3-amino-1-hydroxypropane-1,1-diphosphonate pentahydrate |
| IL77243A (en) * | 1984-12-21 | 1996-11-14 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds |
| IT1187828B (it) * | 1985-05-24 | 1987-12-23 | Gentili Ist Spa | Composizione farmaceutica a base di difosfonati per il trattamento dell aretrosi |
| DE3770982D1 (de) * | 1986-04-24 | 1991-08-01 | Fujisawa Pharmaceutical Co | Diphosphonsaeure-verbindungen, verfahren zu deren herstellung und sie enthaltende arzneimittel. |
| DE3623397A1 (de) * | 1986-07-11 | 1988-01-14 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| GB8618259D0 (en) * | 1986-07-25 | 1986-09-03 | Leo Pharm Prod Ltd | Pharmaceutical compositions |
| ES2039259T3 (es) * | 1986-11-21 | 1993-09-16 | Ciba-Geigy Ag | Procedimiento para la obtencion de acidos azacicloalquil alcandifosfonicos aromaticamente substituidos. |
| US4933472A (en) * | 1988-04-08 | 1990-06-12 | Yamanouchi Pharmaceutical Co., Ltd. | Substituted aminomethylenebis(phosphonic acid) derivatives |
-
1990
- 1990-02-14 PH PH40050A patent/PH26923A/en unknown
- 1990-02-16 US US07/481,482 patent/US5036058A/en not_active Expired - Fee Related
- 1990-02-16 AU AU49884/90A patent/AU629298B2/en not_active Ceased
- 1990-02-27 AT AT90810150T patent/ATE117308T1/de not_active IP Right Cessation
- 1990-02-27 DE DE59008275T patent/DE59008275D1/de not_active Expired - Fee Related
- 1990-02-27 ES ES90810150T patent/ES2067010T3/es not_active Expired - Lifetime
- 1990-02-27 EP EP90810150A patent/EP0387194B1/de not_active Expired - Lifetime
- 1990-02-27 DK DK90810150.4T patent/DK0387194T3/da active
- 1990-03-01 IL IL9358690A patent/IL93586A/en not_active IP Right Cessation
- 1990-03-05 FI FI901103A patent/FI95264C/fi not_active IP Right Cessation
- 1990-03-06 DD DD90338447A patent/DD297824A5/de unknown
- 1990-03-06 KR KR1019900002896A patent/KR900014413A/ko not_active Application Discontinuation
- 1990-03-06 PT PT93353A patent/PT93353B/pt not_active IP Right Cessation
- 1990-03-06 CA CA002011586A patent/CA2011586A1/en not_active Abandoned
- 1990-03-06 NZ NZ232805A patent/NZ232805A/en unknown
- 1990-03-06 MX MX19785A patent/MX19785A/es unknown
- 1990-03-07 HU HU901348A patent/HU206120B/hu not_active IP Right Cessation
- 1990-03-07 NO NO901077A patent/NO174152C/no unknown
- 1990-03-07 IE IE80990A patent/IE64984B1/en not_active IP Right Cessation
- 1990-03-07 ZA ZA901742A patent/ZA901742B/xx unknown
- 1990-03-08 JP JP2055163A patent/JPH02279689A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HUT53112A (en) | 1990-09-28 |
| AU4988490A (en) | 1990-09-13 |
| NZ232805A (en) | 1992-06-25 |
| FI95264B (fi) | 1995-09-29 |
| US5036058A (en) | 1991-07-30 |
| NO901077D0 (no) | 1990-03-07 |
| EP0387194B1 (de) | 1995-01-18 |
| HU901348D0 (en) | 1990-05-28 |
| JPH02279689A (ja) | 1990-11-15 |
| AU629298B2 (en) | 1992-10-01 |
| EP0387194A1 (de) | 1990-09-12 |
| FI901103A0 (fi) | 1990-03-05 |
| HU206120B (en) | 1992-08-28 |
| NO174152B (no) | 1993-12-13 |
| CA2011586A1 (en) | 1990-09-08 |
| IL93586A0 (en) | 1990-12-23 |
| DE59008275D1 (de) | 1995-03-02 |
| KR900014413A (ko) | 1990-10-23 |
| PT93353B (pt) | 1996-02-29 |
| PT93353A (pt) | 1990-11-07 |
| IL93586A (en) | 1995-06-29 |
| MX19785A (es) | 1994-03-31 |
| IE64984B1 (en) | 1995-09-20 |
| ATE117308T1 (de) | 1995-02-15 |
| DK0387194T3 (da) | 1995-03-20 |
| PH26923A (en) | 1992-12-03 |
| NO174152C (no) | 1994-03-23 |
| NO901077L (no) | 1990-09-10 |
| ES2067010T3 (es) | 1995-03-16 |
| IE900809L (en) | 1990-09-08 |
| ZA901742B (en) | 1990-10-31 |
| FI95264C (fi) | 1996-01-10 |
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