JP2012031185A5 - - Google Patents
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- JP2012031185A5 JP2012031185A5 JP2011204707A JP2011204707A JP2012031185A5 JP 2012031185 A5 JP2012031185 A5 JP 2012031185A5 JP 2011204707 A JP2011204707 A JP 2011204707A JP 2011204707 A JP2011204707 A JP 2011204707A JP 2012031185 A5 JP2012031185 A5 JP 2012031185A5
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- Prior art keywords
- naphthacenecarboxamide
- octahydro
- dioxo
- dimethylamino
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
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- -1 carboxy ester Chemical class 0.000 claims 9
- 239000004098 Tetracycline Substances 0.000 claims 8
- 229960002180 tetracycline Drugs 0.000 claims 8
- 235000019364 tetracycline Nutrition 0.000 claims 8
- 229930101283 tetracycline Natural products 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 229950000614 sancycline Drugs 0.000 claims 6
- 238000000034 method Methods 0.000 claims 4
- 239000002243 precursor Substances 0.000 claims 4
- 150000003522 tetracyclines Chemical class 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 229960003722 doxycycline Drugs 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229960004023 minocycline Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- MTCQOMXDZUULRV-ADOAZJKMSA-N (4s,4as,5ar,12ar)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O MTCQOMXDZUULRV-ADOAZJKMSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- XXYRJHQJYSUIJA-YABKDXSZSA-N (2s,5r,6r)-6-[[(2r)-2-[[[(4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carbonyl]amino]methylamino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxy Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3[C@H](C(C)(C)S[C@@H]32)C(O)=O)=O)NCNC(=O)C2=C(O)[C@@]3(O)C(=O)C=4[C@@H]([C@](C5=CC=CC(O)=C5C=4O)(C)O)C[C@H]3[C@@H](C2=O)N(C)C)=CC=CC=C1 XXYRJHQJYSUIJA-YABKDXSZSA-N 0.000 claims 1
- XIYOPDCBBDCGOE-IWVLMIASSA-N (4s,4ar,5s,5ar,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C=C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1[C@H](O)[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O XIYOPDCBBDCGOE-IWVLMIASSA-N 0.000 claims 1
- SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims 1
- FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 claims 1
- NWXMGUDVXFXRIG-WESIUVDSSA-N (4s,4as,5as,6s,12ar)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O NWXMGUDVXFXRIG-WESIUVDSSA-N 0.000 claims 1
- GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1([C@H]2O)=C(Cl)C=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 claims 1
- FAMUIRDLAWWMCQ-AQFAATAFSA-N (4s,4as,5as,6s,12ar)-n-[[4-[n-(diaminomethylidene)carbamimidoyl]piperazin-1-yl]methyl]-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical compound OC([C@@]1(O)C(=O)C=2[C@@H]([C@](C3=CC=CC(O)=C3C=2O)(C)O)C[C@H]1[C@@H](C1=O)N(C)C)=C1C(=O)NCN1CCN(C(=N)N=C(N)N)CC1 FAMUIRDLAWWMCQ-AQFAATAFSA-N 0.000 claims 1
- BZUKDLNEDCDORL-ULRSWZSCSA-N C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(=O)NCN(C)CCN(C)CNC(=O)C=5C([C@@]6(O)C(O)=C7[C@@H]([C@](C8=CC=CC(O)=C8C7=O)(C)O)C[C@H]6[C@@H](C=5O)N(C)C)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O Chemical compound C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(=O)NCN(C)CCN(C)CNC(=O)C=5C([C@@]6(O)C(O)=C7[C@@H]([C@](C8=CC=CC(O)=C8C7=O)(C)O)C[C@H]6[C@@H](C=5O)N(C)C)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O BZUKDLNEDCDORL-ULRSWZSCSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004099 Chlortetracycline Substances 0.000 claims 1
- FMTDIUIBLCQGJB-UHFFFAOYSA-N Demethylchlortetracyclin Natural products C1C2C(O)C3=C(Cl)C=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O FMTDIUIBLCQGJB-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000004100 Oxytetracycline Substances 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 claims 1
- 229960004475 chlortetracycline Drugs 0.000 claims 1
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 claims 1
- 235000019365 chlortetracycline Nutrition 0.000 claims 1
- 229960002398 demeclocycline Drugs 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229950004798 etamocycline Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229950007488 guamecycline Drugs 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229940042016 methacycline Drugs 0.000 claims 1
- 229960000625 oxytetracycline Drugs 0.000 claims 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims 1
- 235000019366 oxytetracycline Nutrition 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229960003187 penimepicycline Drugs 0.000 claims 1
- MEGKRPMNPGTIIG-VNYBMUHKSA-N penimepicycline Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1.O=C([C@@]1(O)C(O)=C2[C@@H]([C@](C3=CC=CC(O)=C3C2=O)(C)O)C[C@H]1[C@@H](C=1O)N(C)C)C=1C(=O)NCN1CCN(CCO)CC1 MEGKRPMNPGTIIG-VNYBMUHKSA-N 0.000 claims 1
- 229950005777 penimocycline Drugs 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 claims 1
- 229910052723 transition metal Inorganic materials 0.000 claims 1
- 150000003624 transition metals Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Claims (5)
- 以下の構造を有する化合物であって、
式中、Rはメチル、エチルまたはプロピルであり、9位は、アルキニル、シクロアルキル、アリール、アルキルカルボニル、アリールカルボニル、アリールオキシカルボニル、ヒドロキシ、シアノ、アルコキシ、アリールオキシ、カルボキシル、カルボキサミド、カルボキシエステル、および炭素環基またはヘテロ環基からなる群より選択される置換基で置換されている、
化合物、および
[4S−(4α,12aα)]−9−(カルボキシ)−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチル−1,11−ジオキソ−2−ナフタセンカルボキサミド、
[4S−(4α,12aα)]−9−[1’−(E)−(2’−フェニル)エテニル]−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチル−1,11−ジオキソ−2−ナフタセンカルボキサミド、
[4S−(4a,12aα)]−9−[3’−(E)−プロペン酸]−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチル−1,11−ジオキソ−2−ナフタセンカルボキサミド、
[4S−(4a,12aα)]−9−[3’−(E)−プロペン酸ブチル]−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチル−1,11−ジオキソ−2−ナフタセンカルボキサミド、
[4S−(4a,12aα)]−9−[3’−(E)−プロペン酸ブチル]−4,7−ビス(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,10,12,12a−テトラヒドロキシ−1,11−ジオキソ−2−ナフタセンカルボキサミド、
9−フェニルミノサイクリン、
[4S−(4α,12aα)]−7−[3’−(E)−プロペン酸ブチル]−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチル−1,11−ジオキソ−2−ナフタセンカルボキサミド、
7−エチレニルサンサイクリン、
7,9−ジフェニルサンサイクリン、
[4S−(4a,12aα)]−13−(4’−メチルフェニル)−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチレン−1,11−ジオキソ−2−ナフタセンカルボキサミド、
[4S−(4a,12aα)]−13−(3’−カルボキシフェニル)−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチレン−1,11−ジオキソ−2−ナフタセンカルボキサミド、
[4S−(4a,12aα)]−13−(4’−エトキシフェニル)−4−(ジメチルアミノ)−1,4,4a,5,5a,6,11,12a−オクタヒドロ−3,5,10,12,12a−ペンタヒドロキシ−6−メチレン−1,11−ジオキソ−2−ナフタセンカルボキサミド、
9−ヨード−ミノサイクリン、
9−ヨード−サンサイクリン、
9−ヨード−ドキシサイクリン、
7,9−ジヨードサンサイクリン、および
7−ヨードドキシサイクリン
からなる群より選択される化合物、またはその薬学的に許容の塩。 - Rがメチルである、請求項1に記載の化合物、またはその薬学的に許容の塩。
- 置換テトラサイクリン化合物を調製するときの、9−ヨード−ミノサイクリン、9−ヨード−サンサイクリン、9−ヨード−ドキシサイクリン、7,9−ジヨードサンサイクリンおよび7−ヨードドキシサイクリンから選択される化合物、またはその薬学的に許容の塩の使用。
- 9位置換テトラサイクリン化合物を調製するための方法であって、以下の、
(i)反応性テトラサイクリン化学錯体と反応性有機置換基前駆体を、以下の式:
の9位置換テトラサイクリン化合物を形成する条件下で接触させる工程であって、該反応性テトラサイクリン化学錯体は、反応性化学中間体を形成する反応性テトラサイクリンベース前駆化合物と遷移金属触媒を含む、工程、および
(ii)該9位置換テトラサイクリン化合物を触媒水素化して対応する9位アルキル誘導体を形成する工程であって、
該反応性有機置換基前駆体は、以下の式
のアルケニル誘導体である、工程
を包含する方法であって、
該式中、Aは該テトラサイクリンベース前駆化合物であり、かつ、オキシテトラサイクリン、クロルテトラサイクリン、デメクロサイクリン、ドキシサイクリン、ケロカルジン、ミノサイクリン、ロリテテトラサイクリン、リメサイクリン、サンサイクリン、メタサイクリン、アピサイクリン、クロモサイクリン、グアメサイクリン、メグルサイクリン、メピルサイクリン、ペニメピサイクリン、ピパサイクリン、エタモサイクリンおよびペニモサイクリンから選択され、
Rは水素、アルキル、アルケニル、アルキニル、シクロアルキル、アリール、アルキルカルボニル、アリールカルボニル、アルコキシカルボニル、アリールオキシカルボニル、アミノ、ヒドロキシ、シアノ、アルコキシ、アリールオキシおよびカルボキシルからなる群より選択されるか、またはRは−C(O)−R 4 であり、R 4 は水素、シアノもしくはC 1 −C 5 アルコキシ基である、
方法。 - 前記触媒水素化が、炭素上の白金触媒またはパラジウム触媒を用いて低圧水素下にて達成される、請求項4に記載の方法。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15470199P | 1999-09-14 | 1999-09-14 | |
US60/154,701 | 1999-09-14 | ||
US23209100P | 2000-09-12 | 2000-09-12 | |
US60/232,091 | 2000-09-12 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2001523365A Division JP5093953B2 (ja) | 1999-09-14 | 2000-09-13 | 遷移金属を用いた化学反応による置換テトラサイクリンの調製方法 |
Publications (2)
Publication Number | Publication Date |
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JP2012031185A JP2012031185A (ja) | 2012-02-16 |
JP2012031185A5 true JP2012031185A5 (ja) | 2012-12-06 |
Family
ID=26851695
Family Applications (2)
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JP2001523365A Expired - Fee Related JP5093953B2 (ja) | 1999-09-14 | 2000-09-13 | 遷移金属を用いた化学反応による置換テトラサイクリンの調製方法 |
JP2011204707A Withdrawn JP2012031185A (ja) | 1999-09-14 | 2011-09-20 | 遷移金属を用いた化学反応による置換テトラサイクリンの調製方法 |
Family Applications Before (1)
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JP2001523365A Expired - Fee Related JP5093953B2 (ja) | 1999-09-14 | 2000-09-13 | 遷移金属を用いた化学反応による置換テトラサイクリンの調製方法 |
Country Status (21)
Country | Link |
---|---|
US (3) | US6617318B1 (ja) |
EP (5) | EP1666453A1 (ja) |
JP (2) | JP5093953B2 (ja) |
KR (1) | KR100764992B1 (ja) |
CN (2) | CN102336680A (ja) |
AT (2) | ATE323671T1 (ja) |
AU (3) | AU781439C (ja) |
BR (1) | BR0013993A (ja) |
CA (2) | CA2383364C (ja) |
CY (1) | CY1105094T1 (ja) |
CZ (1) | CZ301835B6 (ja) |
DE (1) | DE60027465T2 (ja) |
DK (1) | DK1240133T3 (ja) |
EA (3) | EA012203B1 (ja) |
ES (1) | ES2260051T3 (ja) |
HR (1) | HRP20020322B1 (ja) |
HU (1) | HUP0202798A3 (ja) |
IL (4) | IL148482A0 (ja) |
MX (1) | MXPA02002595A (ja) |
PT (1) | PT1240133E (ja) |
WO (1) | WO2001019784A1 (ja) |
Families Citing this family (62)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6756365B2 (en) * | 1991-11-06 | 2004-06-29 | Trustees Of Tufts College | Reducing tetracycline resistance in living cells |
IL137445A0 (en) * | 1998-01-23 | 2001-07-24 | Tufts College | Pharmaceutically active compounds and methods of use thereof |
US8106225B2 (en) * | 1999-09-14 | 2012-01-31 | Trustees Of Tufts College | Methods of preparing substituted tetracyclines with transition metal-based chemistries |
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2003
- 2003-07-09 US US10/616,531 patent/US7067681B2/en not_active Expired - Lifetime
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2005
- 2005-08-25 AU AU2005204259A patent/AU2005204259B2/en not_active Ceased
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2006
- 2006-03-28 US US11/390,902 patent/US7696187B2/en not_active Expired - Fee Related
- 2006-07-17 CY CY20061100984T patent/CY1105094T1/el unknown
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2007
- 2007-05-10 IL IL183125A patent/IL183125A0/en unknown
- 2007-05-10 IL IL183124A patent/IL183124A/en not_active IP Right Cessation
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2009
- 2009-10-15 AU AU2009225351A patent/AU2009225351B2/en not_active Ceased
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2011
- 2011-09-20 JP JP2011204707A patent/JP2012031185A/ja not_active Withdrawn
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