JP5060685B2 - 新規４−デジメチルアミノテトラサイクリン誘導体 - Google Patents
新規４−デジメチルアミノテトラサイクリン誘導体 Download PDFInfo
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- JP5060685B2 JP5060685B2 JP2000582031A JP2000582031A JP5060685B2 JP 5060685 B2 JP5060685 B2 JP 5060685B2 JP 2000582031 A JP2000582031 A JP 2000582031A JP 2000582031 A JP2000582031 A JP 2000582031A JP 5060685 B2 JP5060685 B2 JP 5060685B2
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- JP
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- Prior art keywords
- deoxy
- hydrogen
- amino
- dedimethylaminotetracycline
- dedimethylamino
- 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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- XCCHQGIGHCRZOS-KBKZQPOHSA-N (4as,5as,6s,12ar)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide Chemical class C1=CC=C2[C@@](C)(O)[C@@H](C[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)C3)(O)C3=O)C3=C(O)C2=C1O XCCHQGIGHCRZOS-KBKZQPOHSA-N 0.000 title abstract description 17
- 239000001257 hydrogen Substances 0.000 claims description 166
- 229910052739 hydrogen Inorganic materials 0.000 claims description 165
- -1 4-dedimethylaminotetracycline compound Chemical class 0.000 claims description 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 abstract description 34
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- 230000008901 benefit Effects 0.000 abstract description 4
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- 229960002180 tetracycline Drugs 0.000 description 76
- 229930101283 tetracycline Natural products 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 150000003522 tetracyclines Chemical class 0.000 description 54
- 125000000217 alkyl group Chemical group 0.000 description 45
- 229910052736 halogen Inorganic materials 0.000 description 41
- 150000002367 halogens Chemical class 0.000 description 41
- 239000000203 mixture Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 150000002431 hydrogen Chemical class 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
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- 239000007787 solid Substances 0.000 description 25
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- 230000000694 effects Effects 0.000 description 22
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 15
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 11
- 229940040944 tetracyclines Drugs 0.000 description 11
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
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- 239000002904 solvent Substances 0.000 description 10
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
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- 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 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
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- XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 229960004023 minocycline Drugs 0.000 description 6
- PGSADBUBUOPOJS-UHFFFAOYSA-N neutral red Chemical compound Cl.C1=C(C)C(N)=CC2=NC3=CC(N(C)C)=CC=C3N=C21 PGSADBUBUOPOJS-UHFFFAOYSA-N 0.000 description 6
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
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- 102000002274 Matrix Metalloproteinases Human genes 0.000 description 5
- 108010000684 Matrix Metalloproteinases Proteins 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 5
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- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 0 CC=CC(c1c(C)c(B=C)c(*)c(O)c1C1=O)=C(C[C@]2CC(O)=C3*)C1=C(*)C2C3=O Chemical compound CC=CC(c1c(C)c(B=C)c(*)c(O)c1C1=O)=C(C[C@]2CC(O)=C3*)C1=C(*)C2C3=O 0.000 description 4
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- GELBJKSFQHNCJX-UHFFFAOYSA-N O-(2-aminoethyl) azidosulfanylmethanethioate Chemical compound NCCOC(=S)SN=[N+]=[N-] GELBJKSFQHNCJX-UHFFFAOYSA-N 0.000 description 4
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- C07C329/12—Dithiocarbonic acids; Derivatives thereof
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- C07C329/20—Esters of dithiocarbonic acids having sulfur atoms of dithiocarbonic groups bound to carbon atoms of six-membered aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10894898P | 1998-11-18 | 1998-11-18 | |
| US19501398A | 1998-11-18 | 1998-11-18 | |
| US60/108,948 | 1998-11-18 | ||
| US09/195,013 | 1998-11-18 | ||
| PCT/US1999/027304 WO2000028983A1 (en) | 1998-11-18 | 1999-11-18 | Novel 4-dedimethy laminotetra cycline derivatives |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
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| JP2009228453A Division JP2010043102A (ja) | 1998-11-18 | 2009-09-30 | 新規４−デジメチルアミノテトラサイクリン誘導体 |
| JP2010238591A Division JP5130417B2 (ja) | 1998-11-18 | 2010-10-25 | 新規４−デジメチルアミノテトラサイクリン誘導体 |
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| JP2002529501A JP2002529501A (ja) | 2002-09-10 |
| JP2002529501A5 JP2002529501A5 (enExample) | 2009-11-19 |
| JP5060685B2 true JP5060685B2 (ja) | 2012-10-31 |
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| JP2000582031A Expired - Fee Related JP5060685B2 (ja) | 1998-11-18 | 1999-11-18 | 新規４−デジメチルアミノテトラサイクリン誘導体 |
| JP2009228453A Pending JP2010043102A (ja) | 1998-11-18 | 2009-09-30 | 新規４−デジメチルアミノテトラサイクリン誘導体 |
| JP2010238591A Expired - Fee Related JP5130417B2 (ja) | 1998-11-18 | 2010-10-25 | 新規４−デジメチルアミノテトラサイクリン誘導体 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2009228453A Pending JP2010043102A (ja) | 1998-11-18 | 2009-09-30 | 新規４−デジメチルアミノテトラサイクリン誘導体 |
| JP2010238591A Expired - Fee Related JP5130417B2 (ja) | 1998-11-18 | 2010-10-25 | 新規４−デジメチルアミノテトラサイクリン誘導体 |
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| EP (2) | EP1743632A1 (enExample) |
| JP (3) | JP5060685B2 (enExample) |
| KR (1) | KR100701635B1 (enExample) |
| AT (1) | ATE336238T1 (enExample) |
| AU (1) | AU766200B2 (enExample) |
| CA (1) | CA2351703C (enExample) |
| CY (1) | CY1106224T1 (enExample) |
| DE (1) | DE69932846T2 (enExample) |
| DK (1) | DK1137410T3 (enExample) |
| ES (1) | ES2272097T3 (enExample) |
| NZ (1) | NZ511194A (enExample) |
| PT (1) | PT1137410E (enExample) |
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Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6506740B1 (en) | 1998-11-18 | 2003-01-14 | Robert A. Ashley | 4-dedimethylaminotetracycline derivatives |
| ES2272097T3 (es) * | 1998-11-18 | 2007-04-16 | Collagenex Pharmaceuticals, Inc. | Nuevos derivados de 4-desdimetilaminotetraciclina. |
| US6946453B2 (en) | 1998-11-18 | 2005-09-20 | Collagenex Pharmaceuticals, Inc. | 4-dedimethylaminotracycline derivatives |
| BR0112265A (pt) * | 2000-07-07 | 2003-06-24 | Tufts College | Compostos de tetraciclina substituìda, e de sanciclina 7-substituìda, método para tratar um estado responsivo à tetraciclina em um indivìduo, e, composição farmacêutica |
| ATE504562T1 (de) * | 2000-07-07 | 2011-04-15 | Tufts College | 7-, 8- und 9-substitutierte tetracyclinverbindungen |
| CZ2003344A3 (cs) | 2000-07-07 | 2003-05-14 | Trustees Of Tufts College | 9-Substituované minocyklinové sloučeniny |
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-
1999
- 1999-11-18 ES ES99967109T patent/ES2272097T3/es not_active Expired - Lifetime
- 1999-11-18 KR KR1020017006216A patent/KR100701635B1/ko not_active Expired - Fee Related
- 1999-11-18 CA CA002351703A patent/CA2351703C/en not_active Expired - Fee Related
- 1999-11-18 DK DK99967109T patent/DK1137410T3/da active
- 1999-11-18 JP JP2000582031A patent/JP5060685B2/ja not_active Expired - Fee Related
- 1999-11-18 AU AU23456/00A patent/AU766200B2/en not_active Ceased
- 1999-11-18 WO PCT/US1999/027304 patent/WO2000028983A1/en not_active Ceased
- 1999-11-18 DE DE69932846T patent/DE69932846T2/de not_active Expired - Lifetime
- 1999-11-18 NZ NZ511194A patent/NZ511194A/en not_active IP Right Cessation
- 1999-11-18 EP EP06076306A patent/EP1743632A1/en not_active Withdrawn
- 1999-11-18 AT AT99967109T patent/ATE336238T1/de active
- 1999-11-18 PT PT99967109T patent/PT1137410E/pt unknown
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| Publication number | Publication date |
|---|---|
| DE69932846D1 (de) | 2006-09-28 |
| AU766200B2 (en) | 2003-10-09 |
| CA2351703A1 (en) | 2000-05-25 |
| EP1743632A1 (en) | 2007-01-17 |
| NZ511194A (en) | 2003-08-29 |
| WO2000028983A1 (en) | 2000-05-25 |
| EP1137410B1 (en) | 2006-08-16 |
| JP2010043102A (ja) | 2010-02-25 |
| ATE336238T1 (de) | 2006-09-15 |
| AU2345600A (en) | 2000-06-05 |
| EP1137410A4 (en) | 2002-06-26 |
| KR100701635B1 (ko) | 2007-03-30 |
| JP2011021032A (ja) | 2011-02-03 |
| DE69932846T2 (de) | 2007-03-15 |
| CA2351703C (en) | 2008-12-30 |
| JP5130417B2 (ja) | 2013-01-30 |
| ES2272097T3 (es) | 2007-04-16 |
| EP1137410A1 (en) | 2001-10-04 |
| PT1137410E (pt) | 2007-01-31 |
| JP2002529501A (ja) | 2002-09-10 |
| KR20010082303A (ko) | 2001-08-29 |
| CY1106224T1 (el) | 2011-06-08 |
| DK1137410T3 (da) | 2006-12-27 |
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