NO313198B1 - Imino-aza-antracyklinonderivater fremgangsmåte for fremstilling, anvendelse samt farmasöytiske sammensetningerinneholdende derivatene - Google Patents
Imino-aza-antracyklinonderivater fremgangsmåte for fremstilling, anvendelse samt farmasöytiske sammensetningerinneholdende derivatene Download PDFInfo
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- NO313198B1 NO313198B1 NO19993549A NO993549A NO313198B1 NO 313198 B1 NO313198 B1 NO 313198B1 NO 19993549 A NO19993549 A NO 19993549A NO 993549 A NO993549 A NO 993549A NO 313198 B1 NO313198 B1 NO 313198B1
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- Prior art keywords
- formula
- compound
- alkyl
- mmol
- hydrogen
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- 238000000034 method Methods 0.000 title claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 9
- 229940045799 anthracyclines and related substance Drugs 0.000 title description 4
- 230000008569 process Effects 0.000 title description 2
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- 239000000203 mixture Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
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- 238000006243 chemical reaction Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
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- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
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- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- 230000036210 malignancy Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- INOCPWZDQJBNMJ-UHFFFAOYSA-N o-(pyridin-4-ylmethyl)hydroxylamine;hydrochloride Chemical compound Cl.NOCC1=CC=NC=C1 INOCPWZDQJBNMJ-UHFFFAOYSA-N 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 238000004393 prognosis Methods 0.000 description 1
- 230000005522 programmed cell death Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 208000012263 renal involvement Diseases 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000007470 synaptic degeneration Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 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
- 239000012085 test solution Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9701628.1A GB9701628D0 (en) | 1997-01-27 | 1997-01-27 | Imino-aza-anthracyclinone derivatives |
| PCT/EP1998/000152 WO1998032754A1 (en) | 1997-01-27 | 1998-01-09 | Imino-aza-anthracyclinone derivatives for the treatment of amyloidosis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993549D0 NO993549D0 (no) | 1999-07-20 |
| NO993549L NO993549L (no) | 1999-09-21 |
| NO313198B1 true NO313198B1 (no) | 2002-08-26 |
Family
ID=10806639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993549A NO313198B1 (no) | 1997-01-27 | 1999-07-20 | Imino-aza-antracyklinonderivater fremgangsmåte for fremstilling, anvendelse samt farmasöytiske sammensetningerinneholdende derivatene |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6194422B1 (ja) |
| EP (1) | EP0970080B1 (ja) |
| JP (1) | JP2001511123A (ja) |
| KR (1) | KR20000070483A (ja) |
| CN (1) | CN1103774C (ja) |
| AR (1) | AR011572A1 (ja) |
| AT (1) | ATE235494T1 (ja) |
| AU (1) | AU745981B2 (ja) |
| BR (1) | BR9815448A (ja) |
| CA (1) | CA2277951C (ja) |
| DE (1) | DE69812599T2 (ja) |
| DK (1) | DK0970080T3 (ja) |
| EA (1) | EA001887B1 (ja) |
| ES (1) | ES2195313T3 (ja) |
| GB (1) | GB9701628D0 (ja) |
| HU (1) | HUP0001222A3 (ja) |
| IL (1) | IL130831A (ja) |
| NO (1) | NO313198B1 (ja) |
| NZ (1) | NZ337221A (ja) |
| PL (1) | PL190304B1 (ja) |
| PT (1) | PT970080E (ja) |
| TW (1) | TW519544B (ja) |
| UA (1) | UA57063C2 (ja) |
| WO (1) | WO1998032754A1 (ja) |
| ZA (1) | ZA98611B (ja) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9902938D0 (en) * | 1999-02-10 | 1999-03-31 | Novartis Ag | Organic compounds |
| GB9911804D0 (en) * | 1999-05-20 | 1999-07-21 | Merck Sharp & Dohme | Therapeutic combination |
| US7053191B2 (en) * | 2003-05-21 | 2006-05-30 | Solux Corporation | Method of preparing 4-R-substituted 4-demethoxydaunorubicin |
| US8357785B2 (en) * | 2008-01-08 | 2013-01-22 | Solux Corporation | Method of aralkylation of 4′-hydroxyl group of anthracylins |
| US9376406B2 (en) | 2011-03-03 | 2016-06-28 | Indiana University Research And Technology Corporation | uPAR-uPA interaction inhibitors and methods for treating cancer |
| US8846882B2 (en) | 2011-04-29 | 2014-09-30 | Synbias Pharma Ag | Method of producing 4-demethoxydaunorubicin |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2258652A (en) * | 1991-08-15 | 1993-02-17 | Merck Sharp & Dohme | Pharmaceutically useful azabicyclic oxime ethers |
| GB9416007D0 (en) * | 1994-08-08 | 1994-09-28 | Erba Carlo Spa | Anthracyclinone derivatives |
| GB9418260D0 (en) * | 1994-09-09 | 1994-10-26 | Erba Carlo Spa | Anthracycline derivatives |
| GB9516349D0 (en) * | 1995-08-09 | 1995-10-11 | Pharmacia Spa | Aza-anthracyclinone derivatives |
-
1997
- 1997-01-27 GB GBGB9701628.1A patent/GB9701628D0/en active Pending
- 1997-12-10 TW TW086118863A patent/TW519544B/zh active
-
1998
- 1998-01-09 IL IL13083198A patent/IL130831A/xx not_active IP Right Cessation
- 1998-01-09 DE DE69812599T patent/DE69812599T2/de not_active Expired - Fee Related
- 1998-01-09 NZ NZ337221A patent/NZ337221A/xx unknown
- 1998-01-09 EA EA199900684A patent/EA001887B1/ru not_active IP Right Cessation
- 1998-01-09 ES ES98901964T patent/ES2195313T3/es not_active Expired - Lifetime
- 1998-01-09 EP EP98901964A patent/EP0970080B1/en not_active Expired - Lifetime
- 1998-01-09 CN CN98802091A patent/CN1103774C/zh not_active Expired - Fee Related
- 1998-01-09 HU HU0001222A patent/HUP0001222A3/hu unknown
- 1998-01-09 JP JP53153498A patent/JP2001511123A/ja not_active Withdrawn
- 1998-01-09 BR BR9815448-6A patent/BR9815448A/pt not_active Application Discontinuation
- 1998-01-09 AT AT98901964T patent/ATE235494T1/de not_active IP Right Cessation
- 1998-01-09 KR KR1019997006726A patent/KR20000070483A/ko not_active Application Discontinuation
- 1998-01-09 US US09/341,703 patent/US6194422B1/en not_active Expired - Fee Related
- 1998-01-09 WO PCT/EP1998/000152 patent/WO1998032754A1/en not_active Application Discontinuation
- 1998-01-09 PL PL98334803A patent/PL190304B1/pl not_active IP Right Cessation
- 1998-01-09 DK DK98901964T patent/DK0970080T3/da active
- 1998-01-09 AU AU58633/98A patent/AU745981B2/en not_active Ceased
- 1998-01-09 CA CA002277951A patent/CA2277951C/en not_active Expired - Fee Related
- 1998-01-09 PT PT98901964T patent/PT970080E/pt unknown
- 1998-01-26 AR ARP980100326A patent/AR011572A1/es unknown
- 1998-01-26 ZA ZA98611A patent/ZA98611B/xx unknown
- 1998-09-01 UA UA99084831A patent/UA57063C2/uk unknown
-
1999
- 1999-07-20 NO NO19993549A patent/NO313198B1/no unknown
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