CA2980845A1 - Water-soluble prodrugs - Google Patents
Water-soluble prodrugs Download PDFInfo
- Publication number
- CA2980845A1 CA2980845A1 CA2980845A CA2980845A CA2980845A1 CA 2980845 A1 CA2980845 A1 CA 2980845A1 CA 2980845 A CA2980845 A CA 2980845A CA 2980845 A CA2980845 A CA 2980845A CA 2980845 A1 CA2980845 A1 CA 2980845A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- optionally substituted
- halogen atom
- 6alkoxy
- membered monocyclic
- 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.)
- Abandoned
Links
- 229940002612 prodrug Drugs 0.000 title description 21
- 239000000651 prodrug Substances 0.000 title description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 319
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 259
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 240
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 229
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 195
- 150000003839 salts Chemical class 0.000 claims abstract description 194
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 182
- 125000003277 amino group Chemical group 0.000 claims abstract description 170
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 78
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 70
- 125000005843 halogen group Chemical group 0.000 claims description 364
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 286
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 274
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 253
- 125000001424 substituent group Chemical group 0.000 claims description 215
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 137
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical group [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 133
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 126
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 76
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 74
- 206010028980 Neoplasm Diseases 0.000 claims description 66
- 201000011510 cancer Diseases 0.000 claims description 65
- 239000003814 drug Substances 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 56
- 238000004519 manufacturing process Methods 0.000 claims description 50
- 239000008194 pharmaceutical composition Substances 0.000 claims description 48
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 38
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 229940124597 therapeutic agent Drugs 0.000 claims description 27
- 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 25
- 208000006332 Choriocarcinoma Diseases 0.000 claims description 24
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- 125000006586 (C3-C10) cycloalkylene group Chemical group 0.000 claims description 17
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 17
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 13
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 11
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
- 230000000069 prophylactic effect Effects 0.000 claims description 10
- 206010006187 Breast cancer Diseases 0.000 claims description 9
- 208000026310 Breast neoplasm Diseases 0.000 claims description 9
- 206010009944 Colon cancer Diseases 0.000 claims description 9
- 206010025323 Lymphomas Diseases 0.000 claims description 9
- 208000029742 colonic neoplasm Diseases 0.000 claims description 9
- 125000006585 (C6-C10) arylene group Chemical group 0.000 claims description 8
- 206010000830 Acute leukaemia Diseases 0.000 claims description 8
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 8
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 8
- 206010004593 Bile duct cancer Diseases 0.000 claims description 8
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 8
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 8
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 8
- 206010014733 Endometrial cancer Diseases 0.000 claims description 8
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 8
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 8
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 8
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 8
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 8
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- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 8
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 8
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 8
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 8
- 206010039491 Sarcoma Diseases 0.000 claims description 8
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 8
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 8
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims description 8
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 8
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 8
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 8
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 8
- 208000008383 Wilms tumor Diseases 0.000 claims description 8
- 208000017733 acquired polycythemia vera Diseases 0.000 claims description 8
- 208000026900 bile duct neoplasm Diseases 0.000 claims description 8
- 201000010881 cervical cancer Diseases 0.000 claims description 8
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 8
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 8
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 8
- 201000004101 esophageal cancer Diseases 0.000 claims description 8
- 210000000232 gallbladder Anatomy 0.000 claims description 8
- 206010017758 gastric cancer Diseases 0.000 claims description 8
- 201000010536 head and neck cancer Diseases 0.000 claims description 8
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 8
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 8
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 8
- 201000001441 melanoma Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 208000025189 neoplasm of testis Diseases 0.000 claims description 8
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 8
- 201000008968 osteosarcoma Diseases 0.000 claims description 8
- 201000002528 pancreatic cancer Diseases 0.000 claims description 8
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 8
- 208000037244 polycythemia vera Diseases 0.000 claims description 8
- 206010038038 rectal cancer Diseases 0.000 claims description 8
- 201000001275 rectum cancer Diseases 0.000 claims description 8
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims description 8
- 201000000849 skin cancer Diseases 0.000 claims description 8
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 8
- 201000011549 stomach cancer Diseases 0.000 claims description 8
- 201000003120 testicular cancer Diseases 0.000 claims description 8
- 201000002510 thyroid cancer Diseases 0.000 claims description 8
- 206010044412 transitional cell carcinoma Diseases 0.000 claims description 8
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 13
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 7
- 101001046686 Homo sapiens Integrin alpha-M Proteins 0.000 claims 5
- 102100022338 Integrin alpha-M Human genes 0.000 claims 5
- 108020004021 3-ketosteroid receptors Proteins 0.000 claims 3
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 claims 1
- -1 amine cation Chemical class 0.000 description 140
- 239000013543 active substance Substances 0.000 description 61
- 239000003112 inhibitor Substances 0.000 description 52
- 239000002246 antineoplastic agent Substances 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000203 mixture Substances 0.000 description 29
- 125000006239 protecting group Chemical group 0.000 description 29
- 230000010261 cell growth Effects 0.000 description 28
- 229940079593 drug Drugs 0.000 description 26
- 239000002904 solvent Substances 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 238000009472 formulation Methods 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000002401 inhibitory effect Effects 0.000 description 18
- 230000003054 hormonal effect Effects 0.000 description 17
- 239000002955 immunomodulating agent Substances 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 16
- 229940127089 cytotoxic agent Drugs 0.000 description 16
- DPHUWDIXHNQOSY-UHFFFAOYSA-N napabucasin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1OC(C(=O)C)=C2 DPHUWDIXHNQOSY-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 102000009465 Growth Factor Receptors Human genes 0.000 description 15
- 108010009202 Growth Factor Receptors Proteins 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 229910052731 fluorine Inorganic materials 0.000 description 15
- 125000001153 fluoro group Chemical group F* 0.000 description 15
- 239000003102 growth factor Substances 0.000 description 15
- 239000003124 biologic agent Substances 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229960001592 paclitaxel Drugs 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 11
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
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- 229910052736 halogen Inorganic materials 0.000 description 10
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000004579 taxol derivatives Chemical class 0.000 description 1
- 229960000235 temsirolimus Drugs 0.000 description 1
- QFJCIRLUMZQUOT-UHFFFAOYSA-N temsirolimus Natural products C1CC(O)C(OC)CC1CC(C)C1OC(=O)C2CCCCN2C(=O)C(=O)C(O)(O2)C(C)CCC2CC(OC)C(C)=CC=CC=CC(C)CC(C)C(=O)C(OC)C(O)C(C)=CC(C)C(=O)C1 QFJCIRLUMZQUOT-UHFFFAOYSA-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
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000000015 thermotherapy Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000005557 thiazolylene group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- PLHJCIYEEKOWNM-HHHXNRCGSA-N tipifarnib Chemical compound CN1C=NC=C1[C@](N)(C=1C=C2C(C=3C=C(Cl)C=CC=3)=CC(=O)N(C)C2=CC=1)C1=CC=C(Cl)C=C1 PLHJCIYEEKOWNM-HHHXNRCGSA-N 0.000 description 1
- 229950009158 tipifarnib Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229960003989 tocilizumab Drugs 0.000 description 1
- 229960005267 tositumomab Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005558 triazinylene group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 102000015534 trkB Receptor Human genes 0.000 description 1
- 108010064880 trkB Receptor Proteins 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 229950009811 ubenimex Drugs 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229950001212 volociximab Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229950008250 zalutumumab Drugs 0.000 description 1
- 229950009002 zanolimumab Drugs 0.000 description 1
- 235000016804 zinc Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562139077P | 2015-03-27 | 2015-03-27 | |
| US62/139,077 | 2015-03-27 | ||
| PCT/IB2016/051706 WO2016157052A1 (en) | 2015-03-27 | 2016-03-25 | Water-soluble prodrugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2980845A1 true CA2980845A1 (en) | 2016-10-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2980845A Abandoned CA2980845A1 (en) | 2015-03-27 | 2016-03-25 | Water-soluble prodrugs |
Country Status (7)
| Country | Link |
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| US (3) | US10183925B2 (OSRAM) |
| EP (1) | EP3274346A1 (OSRAM) |
| JP (3) | JP6630364B2 (OSRAM) |
| CN (1) | CN107660202B (OSRAM) |
| CA (1) | CA2980845A1 (OSRAM) |
| TW (1) | TWI710555B (OSRAM) |
| WO (1) | WO2016157052A1 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016157052A1 (en) | 2015-03-27 | 2016-10-06 | Boston Biomedical, Inc. | Water-soluble prodrugs |
| JP6936214B2 (ja) | 2016-03-25 | 2021-09-15 | 大日本住友製薬株式会社 | ２−アルキルカルボニルナフト［２，３−ｂ］フラン−４，９−ジオンの関連物質の製造方法、及びその関連物質 |
| CA3045306A1 (en) | 2016-11-29 | 2018-06-07 | Boston Biomedical, Inc. | Naphthofuran derivatives, preparation, and methods of use thereof |
| JP2020520923A (ja) | 2017-05-17 | 2020-07-16 | ボストン バイオメディカル， インコーポレイテッド | がんを処置するための方法 |
| US20200207782A1 (en) * | 2017-09-22 | 2020-07-02 | Sumitomo Dainippon Pharma Co., Ltd | Chemically activated water-soluble prodrug |
| JPWO2021039616A1 (OSRAM) * | 2019-08-23 | 2021-03-04 | ||
| FR3112145A1 (fr) * | 2020-07-03 | 2022-01-07 | Nanotracks Diagnostics | Derives uree de macrolides polyeniques, composes chimiques particuliers susceptibles d’etre utilises pour obtenir ces derives uree, compositions les contenant et utilisations |
| WO2022003181A1 (fr) * | 2020-07-03 | 2022-01-06 | Nanotracks Diagnostics | Derivés urée de l'amphotéricine amb, compositions les contenant et leurs utilisations, dérivés isocyanate d'alkyle omega-aminés et leur utilisation pour obtenir lesdits dérivés urée |
| CN112194598B (zh) * | 2020-10-15 | 2021-12-21 | 郑州猫眼农业科技有限公司 | 3-(叔丁氧基羰基-r氧基羰基甲基-氨基)-丙酸酯的制备方法 |
| EP4431491A4 (en) * | 2021-11-08 | 2025-03-05 | Asahi Kasei Kabushiki Kaisha | CARBONYL COMPOUND, METHOD FOR PRODUCING A CARBONYL COMPOUND, METHOD FOR PRODUCING AN ISOCYANATE COMPOUND AND ISOCYANATE COMPOSITION |
| CN118302407A (zh) * | 2021-11-08 | 2024-07-05 | 旭化成株式会社 | 羰基化合物、羰基化合物的制造方法、异氰酸酯化合物的制造方法以及异氰酸酯组合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20160949T1 (hr) | 2007-09-10 | 2016-10-07 | Boston Biomedical, Inc. | Novi sastavi i metode za liječenje karcinoma |
| WO2012119265A1 (en) | 2011-03-04 | 2012-09-13 | Zhoushan Haizhongzhou Xinsheng Pharmaceuticals Co., Ltd. | NOVEL ESTERS OF 4,9-DIHYDROXY-NAPHTHO[2,3-b]FURANS FOR DISEASE THERAPIES |
| CN104080449A (zh) * | 2012-02-17 | 2014-10-01 | 舟山海中洲新生药业有限公司 | 4，9-二羟基-萘并[2，3-b]呋喃脂肪酸酯衍生物的纳米颗粒水悬液的制备方法 |
| GB201203705D0 (en) | 2012-03-02 | 2012-04-18 | Kappa Bioscience As | Prodrugs |
| WO2013166618A1 (en) | 2012-05-08 | 2013-11-14 | Zhoushan Haizhongzhou Xinsheng Pharmaceuticals Co., Ltd. | PRODRUGS OF 4,9-DIHYDROXY-NAPHTHO[2,3-b]FURANS FOR CIRCUMVENTING CANCER MULTIDRUG RESISTANCE |
| WO2016157052A1 (en) * | 2015-03-27 | 2016-10-06 | Boston Biomedical, Inc. | Water-soluble prodrugs |
-
2016
- 2016-03-25 WO PCT/IB2016/051706 patent/WO2016157052A1/en not_active Ceased
- 2016-03-25 EP EP16714015.1A patent/EP3274346A1/en not_active Ceased
- 2016-03-25 JP JP2017549601A patent/JP6630364B2/ja not_active Expired - Fee Related
- 2016-03-25 TW TW105109636A patent/TWI710555B/zh not_active IP Right Cessation
- 2016-03-25 CA CA2980845A patent/CA2980845A1/en not_active Abandoned
- 2016-03-25 US US15/561,828 patent/US10183925B2/en active Active
- 2016-03-25 CN CN201680030052.0A patent/CN107660202B/zh not_active Expired - Fee Related
-
2018
- 2018-11-19 US US16/194,525 patent/US10800752B2/en not_active Expired - Fee Related
-
2019
- 2019-12-06 JP JP2019221478A patent/JP6885999B2/ja not_active Expired - Fee Related
-
2020
- 2020-08-28 US US17/005,597 patent/US11414394B2/en active Active
-
2021
- 2021-05-13 JP JP2021081570A patent/JP2021120401A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US10183925B2 (en) | 2019-01-22 |
| JP2020055854A (ja) | 2020-04-09 |
| JP6885999B2 (ja) | 2021-06-16 |
| TW201639824A (zh) | 2016-11-16 |
| US20190084955A1 (en) | 2019-03-21 |
| HK1243079A1 (zh) | 2018-07-06 |
| JP2021120401A (ja) | 2021-08-19 |
| JP2018509441A (ja) | 2018-04-05 |
| US11414394B2 (en) | 2022-08-16 |
| EP3274346A1 (en) | 2018-01-31 |
| TWI710555B (zh) | 2020-11-21 |
| WO2016157052A1 (en) | 2016-10-06 |
| CN107660202A (zh) | 2018-02-02 |
| US20180111914A1 (en) | 2018-04-26 |
| JP6630364B2 (ja) | 2020-01-15 |
| US10800752B2 (en) | 2020-10-13 |
| US20200392098A1 (en) | 2020-12-17 |
| CN107660202B (zh) | 2021-12-24 |
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Effective date: 20210222 |
|
| EEER | Examination request |
Effective date: 20210222 |
|
| EEER | Examination request |
Effective date: 20210222 |
|
| FZDE | Discontinued |
Effective date: 20231011 |