DE2815724A1 - Indolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Indolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2815724A1 DE2815724A1 DE19782815724 DE2815724A DE2815724A1 DE 2815724 A1 DE2815724 A1 DE 2815724A1 DE 19782815724 DE19782815724 DE 19782815724 DE 2815724 A DE2815724 A DE 2815724A DE 2815724 A1 DE2815724 A1 DE 2815724A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- methyl
- group
- acid
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 48
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 152
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 30
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 29
- -1 alkyl radical Chemical class 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 16
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 16
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 12
- 150000003852 triazoles Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000001540 azides Chemical class 0.000 claims description 9
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 8
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 229930016911 cinnamic acid Natural products 0.000 claims description 8
- 235000013985 cinnamic acid Nutrition 0.000 claims description 8
- NGFCTYXFMDWFRQ-UHFFFAOYSA-N isoquinolin-6-amine Chemical compound C1=NC=CC2=CC(N)=CC=C21 NGFCTYXFMDWFRQ-UHFFFAOYSA-N 0.000 claims description 8
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 235000010288 sodium nitrite Nutrition 0.000 claims description 8
- UGYGQUPNHYOWJW-AATRIKPKSA-N (e)-3-(2-methyl-3-nitrophenyl)prop-2-enoic acid Chemical compound CC1=C(\C=C\C(O)=O)C=CC=C1[N+]([O-])=O UGYGQUPNHYOWJW-AATRIKPKSA-N 0.000 claims description 7
- JOTRPRKONYTVBV-UHFFFAOYSA-N 4-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CN=CC=C1Cl JOTRPRKONYTVBV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003172 aldehyde group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- MVYLQDBIAVEAHD-UHFFFAOYSA-N 2-chloro-2-(2-methyl-3-nitrophenyl)propanoic acid Chemical compound CC1=C([N+]([O-])=O)C=CC=C1C(C)(Cl)C(O)=O MVYLQDBIAVEAHD-UHFFFAOYSA-N 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
- HFCFJYRLBAANKN-UHFFFAOYSA-N 2-methyl-3-nitroaniline Chemical compound CC1=C(N)C=CC=C1[N+]([O-])=O HFCFJYRLBAANKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000012188 paraffin wax Substances 0.000 claims description 3
- NNLYGBLHDBWCEO-UHFFFAOYSA-N 3-(3-acetamido-2-methylphenyl)prop-2-enoic acid Chemical compound CC(=O)NC1=CC=CC(C=CC(O)=O)=C1C NNLYGBLHDBWCEO-UHFFFAOYSA-N 0.000 claims description 2
- HREHFGWMMVPDJB-UHFFFAOYSA-N 6-amino-5-methyl-2h-isoquinolin-1-one Chemical compound C1=CNC(=O)C2=C1C(C)=C(N)C=C2 HREHFGWMMVPDJB-UHFFFAOYSA-N 0.000 claims description 2
- MPAAGWPNIQFBMW-UHFFFAOYSA-N CC([O-])=O.CC([O-])=O.C1=CC=C2[NH2+]CCC2=C1.C1=CC=C2[NH2+]CCC2=C1 Chemical compound CC([O-])=O.CC([O-])=O.C1=CC=C2[NH2+]CCC2=C1.C1=CC=C2[NH2+]CCC2=C1 MPAAGWPNIQFBMW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- VTUPGPGMFTYXDB-UHFFFAOYSA-N n-(3-cyano-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C#N)=C1C VTUPGPGMFTYXDB-UHFFFAOYSA-N 0.000 claims description 2
- MPBHUUARFICUKB-UHFFFAOYSA-N n-(3-formyl-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=O)=C1C MPBHUUARFICUKB-UHFFFAOYSA-N 0.000 claims description 2
- OIRPZDREMBKFBR-UHFFFAOYSA-N n-(5,8-dimethyl-1-oxo-2h-isoquinolin-6-yl)acetamide Chemical compound C1=CNC(=O)C=2C1=C(C)C(NC(=O)C)=CC=2C OIRPZDREMBKFBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- GTENNRWWXNGTOJ-ONEGZZNKSA-N (e)-3-(2,5-dimethyl-3-nitrophenyl)prop-2-enoic acid Chemical compound CC1=CC(\C=C\C(O)=O)=C(C)C([N+]([O-])=O)=C1 GTENNRWWXNGTOJ-ONEGZZNKSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 241000699670 Mus sp. Species 0.000 description 73
- 210000004027 cell Anatomy 0.000 description 69
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- 241001465754 Metazoa Species 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- 239000000203 mixture Substances 0.000 description 53
- 241000699666 Mus <mouse, genus> Species 0.000 description 46
- 206010028980 Neoplasm Diseases 0.000 description 45
- 239000000047 product Substances 0.000 description 43
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 241000700605 Viruses Species 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 208000032839 leukemia Diseases 0.000 description 28
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- 238000000921 elemental analysis Methods 0.000 description 26
- 239000002244 precipitate Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 23
- 229940126086 compound 21 Drugs 0.000 description 23
- 238000002474 experimental method Methods 0.000 description 23
- 239000007924 injection Substances 0.000 description 23
- 238000002347 injection Methods 0.000 description 23
- 238000012360 testing method Methods 0.000 description 20
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 19
- 239000013081 microcrystal Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
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- 230000015572 biosynthetic process Effects 0.000 description 10
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 5
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- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000009123 therapy by drug Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Communicable Diseases (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7711148A FR2387229A1 (fr) | 1977-04-13 | 1977-04-13 | Dipyrido (4,3-b) (3,4-f) indoles, procede d'obtention, application therapeutique et compositions pharmaceutiques les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2815724A1 true DE2815724A1 (de) | 1978-10-26 |
| DE2815724C2 DE2815724C2 (en, 2012) | 1991-02-14 |
Family
ID=9189361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782815724 Granted DE2815724A1 (de) | 1977-04-13 | 1978-04-12 | Indolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4266060A (en, 2012) |
| JP (1) | JPS549299A (en, 2012) |
| BE (1) | BE865851A (en, 2012) |
| CA (1) | CA1117945A (en, 2012) |
| CH (1) | CH633796A5 (en, 2012) |
| DE (1) | DE2815724A1 (en, 2012) |
| ES (1) | ES468721A1 (en, 2012) |
| FR (1) | FR2387229A1 (en, 2012) |
| GB (1) | GB1603228A (en, 2012) |
| IT (1) | IT1095582B (en, 2012) |
| LU (1) | LU79422A1 (en, 2012) |
| NL (1) | NL184895C (en, 2012) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4334070A (en) * | 1980-12-15 | 1982-06-08 | Hoffmann-La Roche Inc. | Cycloalka[4,5]pyrrolo[2,3-g]isoquinolines |
| DK158666C (da) * | 1982-11-04 | 1990-11-19 | Glaxo Group Ltd | Analogifremgangsmaade til fremstilling af 5,14-dihydrobenz-oe5,6aa-isoindolooe2,1-baa-isoquinolin-8,13-dion |
| DK160991C (da) * | 1984-05-03 | 1991-11-11 | Glaxo Group Ltd | 5,14-dihydrobenzoe5,6aaisoindolooe2,1-baaisoquinolin-8,13-dionderivater, fremgangsmaade til fremstilling deraf og farmaceutisk praeparat indeholdende en saadan forbindelse |
| JPH0642591B2 (ja) * | 1984-11-30 | 1994-06-01 | ミノルタカメラ株式会社 | プリント配線基板の製造方法 |
| NO872963L (no) * | 1986-07-29 | 1988-02-01 | Glaxo Group Ltd | Isokinolinderivater. |
| DK616087A (da) * | 1986-11-27 | 1988-05-28 | Glaxo Group Ltd | Isoquinolinderivater og farmaceutiske praeparater indeholdende dem |
| GB8800312D0 (en) * | 1988-01-07 | 1988-02-10 | Glaxo Group Ltd | Process |
| FR2627493B1 (fr) * | 1988-02-23 | 1991-10-31 | Sanofi Sa | Procede de preparation de derives d'isoquinoleine |
| FR2645861A1 (fr) * | 1989-04-17 | 1990-10-19 | Inst Nat Sante Rech Med | Utilisation de dipyrido (4,3-b) (3,4-f) indoles pour la preparation de medicaments utiles pour le traitement du sida |
| US5281608A (en) * | 1992-08-28 | 1994-01-25 | American Home Products Corporation | Substituted tetrahydropyrido[3',4':4,5]-pyrrolo[3,2-c]quinolines |
| FR2859474B1 (fr) * | 2003-09-04 | 2006-01-13 | Centre Nat Rech Scient | Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| BRPI0507373A (pt) * | 2004-01-23 | 2007-07-10 | Amgen Inc | compostos e método de uso |
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| KR102016889B1 (ko) | 2009-06-12 | 2019-08-30 | 아비박스 | 조기 노화, 구체적으로 조로증을 치료하는데 유용한 화합물 |
| EP2266972A1 (en) * | 2009-06-12 | 2010-12-29 | Splicos | New chemical molecules that inhibit the splicing mechanism for treating diseases resulting from splicing anomalies |
| EP2465502A1 (en) | 2010-12-15 | 2012-06-20 | Société Splicos | Compounds useful for treating AIDS |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| AU2014285733B2 (en) | 2013-07-05 | 2019-05-16 | Abivax | Bicyclic compounds useful for treating diseases caused by retroviruses |
| EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2248828B1 (en, 2012) * | 1973-10-29 | 1977-04-15 | Anvar | |
| US3933827A (en) * | 1974-10-29 | 1976-01-20 | Hoffmann-La Roche Inc. | 9-Acyloxy-5,11-dimethyl-6H-pyrido[4,3-B]carbazoles |
-
1977
- 1977-04-13 FR FR7711148A patent/FR2387229A1/fr active Granted
-
1978
- 1978-04-10 BE BE186694A patent/BE865851A/xx not_active IP Right Cessation
- 1978-04-12 IT IT22254/78A patent/IT1095582B/it active
- 1978-04-12 CA CA000301011A patent/CA1117945A/en not_active Expired
- 1978-04-12 GB GB14337/78A patent/GB1603228A/en not_active Expired
- 1978-04-12 DE DE19782815724 patent/DE2815724A1/de active Granted
- 1978-04-12 CH CH391878A patent/CH633796A5/fr not_active IP Right Cessation
- 1978-04-12 LU LU79422A patent/LU79422A1/xx unknown
- 1978-04-12 ES ES468721A patent/ES468721A1/es not_active Expired
- 1978-04-13 US US05/896,101 patent/US4266060A/en not_active Expired - Lifetime
- 1978-04-13 JP JP4376678A patent/JPS549299A/ja active Granted
- 1978-04-13 NL NLAANVRAGE7803951,A patent/NL184895C/xx not_active IP Right Cessation
-
1980
- 1980-11-21 US US06/209,091 patent/US4444776A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| Cancer Research, 36, 1976, 3067-76 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES468721A1 (es) | 1978-12-16 |
| CH633796A5 (fr) | 1982-12-31 |
| US4266060A (en) | 1981-05-05 |
| FR2387229A1 (fr) | 1978-11-10 |
| DE2815724C2 (en, 2012) | 1991-02-14 |
| LU79422A1 (fr) | 1979-11-07 |
| GB1603228A (en) | 1981-11-18 |
| NL184895C (nl) | 1989-12-01 |
| BE865851A (fr) | 1978-10-10 |
| CA1117945A (en) | 1982-02-09 |
| NL7803951A (nl) | 1978-10-17 |
| US4444776A (en) | 1984-04-24 |
| NL184895B (nl) | 1989-07-03 |
| JPS549299A (en) | 1979-01-24 |
| FR2387229B1 (en, 2012) | 1980-05-09 |
| IT7822254A0 (it) | 1978-04-12 |
| JPS6225670B2 (en, 2012) | 1987-06-04 |
| IT1095582B (it) | 1985-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SCHOENWALD, K., DR.-ING. FUES, J., DIPL.-CHEM. DR. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |