NO313617B1 - Cytotoksisk medikament, konjugater av metyltritisantitumor- midler, mellomprodukter og anvendelse derav samt fremgangsmåte forfremstilling, farmasöytisk preparat og frysetörket farmasöytiskpreparat - Google Patents
Cytotoksisk medikament, konjugater av metyltritisantitumor- midler, mellomprodukter og anvendelse derav samt fremgangsmåte forfremstilling, farmasöytisk preparat og frysetörket farmasöytiskpreparat Download PDFInfo
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- NO313617B1 NO313617B1 NO19952206A NO952206A NO313617B1 NO 313617 B1 NO313617 B1 NO 313617B1 NO 19952206 A NO19952206 A NO 19952206A NO 952206 A NO952206 A NO 952206A NO 313617 B1 NO313617 B1 NO 313617B1
- Authority
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- Norway
- Prior art keywords
- bond
- alkyl
- alk
- nconhr
- halogen
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Links
- 238000000034 method Methods 0.000 title claims description 133
- 229940127089 cytotoxic agent Drugs 0.000 title claims description 22
- 239000002254 cytotoxic agent Substances 0.000 title claims description 21
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 52
- 239000002246 antineoplastic agent Substances 0.000 title description 6
- 239000000543 intermediate Substances 0.000 title description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 77
- 150000002367 halogens Chemical class 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 73
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- -1 5-oxazolyl Chemical group 0.000 claims description 63
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 62
- 210000004027 cell Anatomy 0.000 claims description 58
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 52
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 49
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 35
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- 150000003839 salts Chemical class 0.000 claims description 31
- 229930195731 calicheamicin Natural products 0.000 claims description 30
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- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 24
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 108090000623 proteins and genes Proteins 0.000 claims description 19
- 239000000427 antigen Substances 0.000 claims description 18
- 102000036639 antigens Human genes 0.000 claims description 18
- 108091007433 antigens Proteins 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
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- 206010028980 Neoplasm Diseases 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 125000004001 thioalkyl group Chemical group 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 229950000688 phenothiazine Drugs 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
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- 150000001450 anions Chemical class 0.000 claims description 10
- HXCHCVDVKSCDHU-LULTVBGHSA-N calicheamicin Chemical compound C1[C@H](OC)[C@@H](NCC)CO[C@H]1O[C@H]1[C@H](O[C@@H]2C\3=C(NC(=O)OC)C(=O)C[C@](C/3=C/CSSSC)(O)C#C\C=C/C#C2)O[C@H](C)[C@@H](NO[C@@H]2O[C@H](C)[C@@H](SC(=O)C=3C(=C(OC)C(O[C@H]4[C@@H]([C@H](OC)[C@@H](O)[C@H](C)O4)O)=C(I)C=3C)OC)[C@@H](O)C2)[C@@H]1O HXCHCVDVKSCDHU-LULTVBGHSA-N 0.000 claims description 10
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- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 8
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 7
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 5
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 229930006000 Sucrose Natural products 0.000 claims description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 4
- 239000005720 sucrose Substances 0.000 claims description 4
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 4
- 125000006715 (C1-C5) alkylthio group Chemical group 0.000 claims description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
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- 102000010789 Interleukin-2 Receptors Human genes 0.000 claims description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
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- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 claims 1
- PBYIIRLNRCVTMQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorophenol Chemical compound OC1=C(F)C(F)=CC(F)=C1F PBYIIRLNRCVTMQ-UHFFFAOYSA-N 0.000 claims 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 claims 1
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- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims 1
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- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims 1
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- 230000014759 maintenance of location Effects 0.000 description 67
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- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 10
- XCJOFTQRNQNUPS-UHFFFAOYSA-N 4-(2-acetyl-5-methoxyphenoxy)butanoic acid Chemical compound COC1=CC=C(C(C)=O)C(OCCCC(O)=O)=C1 XCJOFTQRNQNUPS-UHFFFAOYSA-N 0.000 description 9
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- QHLKXVXBJDXSHQ-UHFFFAOYSA-N 4-(3-formylphenoxy)butanoic acid Chemical compound OC(=O)CCCOC1=CC=CC(C=O)=C1 QHLKXVXBJDXSHQ-UHFFFAOYSA-N 0.000 description 8
- NGFMLSYWOOYFPR-UHFFFAOYSA-N 4-(5-formyl-2,3-dimethoxyphenoxy)butanoic acid Chemical compound COC1=CC(C=O)=CC(OCCCC(O)=O)=C1OC NGFMLSYWOOYFPR-UHFFFAOYSA-N 0.000 description 8
- YLUUREXLUWBLKT-UHFFFAOYSA-N 5-[4-(4-acetylphenyl)piperazin-1-yl]pentanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1N1CCN(CCCCC(O)=O)CC1 YLUUREXLUWBLKT-UHFFFAOYSA-N 0.000 description 8
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 8
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- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 8
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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Classifications
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
- A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
- A61K47/6807—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug or compound being a sugar, nucleoside, nucleotide, nucleic acid, e.g. RNA antisense
- A61K47/6809—Antibiotics, e.g. antitumor antibiotics anthracyclins, adriamycin, doxorubicin or daunomycin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/253,877 US5773001A (en) | 1994-06-03 | 1994-06-03 | Conjugates of methyltrithio antitumor agents and intermediates for their synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO952206D0 NO952206D0 (no) | 1995-06-02 |
| NO952206L NO952206L (no) | 1995-12-04 |
| NO313617B1 true NO313617B1 (no) | 2002-11-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19952206A NO313617B1 (no) | 1994-06-03 | 1995-06-02 | Cytotoksisk medikament, konjugater av metyltritisantitumor- midler, mellomprodukter og anvendelse derav samt fremgangsmåte forfremstilling, farmasöytisk preparat og frysetörket farmasöytiskpreparat |
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| US (4) | US5773001A (ja) |
| EP (1) | EP0689845B1 (ja) |
| JP (2) | JP3650165B2 (ja) |
| KR (1) | KR100408376B1 (ja) |
| AT (1) | ATE223234T1 (ja) |
| AU (1) | AU697280B2 (ja) |
| BR (2) | BR1101078A (ja) |
| CA (1) | CA2150785C (ja) |
| CY (1) | CY2334B1 (ja) |
| DE (1) | DE69528016T2 (ja) |
| DK (1) | DK0689845T3 (ja) |
| ES (1) | ES2181752T3 (ja) |
| FI (1) | FI117690B (ja) |
| IL (1) | IL113984A (ja) |
| NO (1) | NO313617B1 (ja) |
| NZ (3) | NZ272274A (ja) |
| PT (1) | PT689845E (ja) |
| SI (1) | SI0689845T1 (ja) |
| TW (1) | TW394778B (ja) |
| ZA (1) | ZA954570B (ja) |
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