CN1101038A - 4-取代的6，9-双(取代的氨基)苯并[g]异喹啉-5，10-二酮 - Google Patents
4-取代的6，9-双(取代的氨基)苯并[g]异喹啉-5，10-二酮 Download PDFInfo
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- CN1101038A CN1101038A CN93117376A CN93117376A CN1101038A CN 1101038 A CN1101038 A CN 1101038A CN 93117376 A CN93117376 A CN 93117376A CN 93117376 A CN93117376 A CN 93117376A CN 1101038 A CN1101038 A CN 1101038A
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- China
- Prior art keywords
- compound
- amino
- alkyl
- hydroxyl
- isoquinoline
- Prior art date
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- -1 4-substituted 6,9-bis(substituted-amino) benzo(g) isoquinoline-5, 10-Di-ones Chemical class 0.000 title claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- 230000000259 anti-tumor effect Effects 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 56
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
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- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 claims description 5
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- 238000010438 heat treatment Methods 0.000 claims description 5
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
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- ROTNFTXFUKFPHE-UHFFFAOYSA-N 2-butan-2-ylthiophene Chemical compound CCC(C)C1=CC=CS1 ROTNFTXFUKFPHE-UHFFFAOYSA-N 0.000 claims description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- ABOLPUDOABZSNW-UHFFFAOYSA-N N1CCNCC1.CC1=C(C=C(C(=O)O)C=C1)C(=O)O Chemical compound N1CCNCC1.CC1=C(C=C(C(=O)O)C=C1)C(=O)O ABOLPUDOABZSNW-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
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- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 230000037431 insertion Effects 0.000 description 1
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- 235000014655 lactic acid Nutrition 0.000 description 1
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- 239000007937 lozenge Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
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- 229960001237 podophyllotoxin Drugs 0.000 description 1
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- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
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- 238000012216 screening Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- 231100000820 toxicity test Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/08—Aza-anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94183192A | 1992-09-08 | 1992-09-08 | |
| US07/941,831 | 1992-09-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1101038A true CN1101038A (zh) | 1995-04-05 |
Family
ID=25477142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN93117376A Pending CN1101038A (zh) | 1992-09-08 | 1993-09-08 | 4-取代的6，9-双(取代的氨基)苯并[g]异喹啉-5，10-二酮 |
Country Status (5)
| Country | Link |
|---|---|
| CN (1) | CN1101038A (enExample) |
| AU (1) | AU5099793A (enExample) |
| TW (1) | TW276251B (enExample) |
| WO (1) | WO1994005641A1 (enExample) |
| ZA (1) | ZA936396B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025152949A1 (zh) * | 2024-01-17 | 2025-07-24 | 浙江大学 | 一种异喹啉-5,8-二酮衍生物及其制备方法与应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197249A (en) * | 1977-08-15 | 1980-04-08 | American Cyanamid Company | 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof |
| US5141957A (en) * | 1990-11-02 | 1992-08-25 | Sphinx Pharmaceuticals Corporation | 1,4-bis-(amino-hydroxyalkylamino)-anthraquinones for inhibiting protein kinase c |
| NZ241868A (en) * | 1991-03-08 | 1995-05-26 | Univ Vermont | 6,9-bis(substituted-amino)benzo[g]isoquinoline-5,10-diones, preparation and pharmaceutical compositions thereof |
-
1993
- 1993-08-31 ZA ZA936396A patent/ZA936396B/xx unknown
- 1993-09-02 TW TW082107150A patent/TW276251B/zh active
- 1993-09-08 AU AU50997/93A patent/AU5099793A/en not_active Withdrawn
- 1993-09-08 CN CN93117376A patent/CN1101038A/zh active Pending
- 1993-09-08 WO PCT/US1993/008242 patent/WO1994005641A1/en not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025152949A1 (zh) * | 2024-01-17 | 2025-07-24 | 浙江大学 | 一种异喹啉-5,8-二酮衍生物及其制备方法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5099793A (en) | 1994-03-29 |
| ZA936396B (en) | 1994-06-13 |
| WO1994005641A1 (en) | 1994-03-17 |
| TW276251B (enExample) | 1996-05-21 |
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| C06 | Publication | ||
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| C01 | Deemed withdrawal of patent application (patent law 1993) | ||
| WD01 | Invention patent application deemed withdrawn after publication |