CN1485327A - 替莫唑胺-8-羧酸脂和-8-酰胺衍生物,它们的合成方法以及它们在制备抗癌制剂中的应用 - Google Patents
替莫唑胺-8-羧酸脂和-8-酰胺衍生物,它们的合成方法以及它们在制备抗癌制剂中的应用 Download PDFInfo
- Publication number
- CN1485327A CN1485327A CNA021313466A CN02131346A CN1485327A CN 1485327 A CN1485327 A CN 1485327A CN A021313466 A CNA021313466 A CN A021313466A CN 02131346 A CN02131346 A CN 02131346A CN 1485327 A CN1485327 A CN 1485327A
- Authority
- CN
- China
- Prior art keywords
- methyl
- imidazolo
- oxo
- amide derivatives
- temozolomide
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title abstract description 7
- 230000001093 anti-cancer Effects 0.000 title description 11
- 230000002194 synthesizing effect Effects 0.000 title description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 25
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 23
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 150000001263 acyl chlorides Chemical class 0.000 claims abstract description 3
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- -1 substituted-phenyl Chemical group 0.000 claims description 32
- 238000010521 absorption reaction Methods 0.000 claims description 22
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 5
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 claims description 4
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 2
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000012317 TBTU Substances 0.000 claims description 2
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 claims description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([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
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003560 cancer drug Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 19
- VVTMIOYTNALQAW-UHFFFAOYSA-N 3-methyl-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid Chemical compound O=C1N(C)N=NC2=C(C(O)=O)N=CN21 VVTMIOYTNALQAW-UHFFFAOYSA-N 0.000 abstract description 15
- 239000002243 precursor Substances 0.000 abstract description 4
- 239000002246 antineoplastic agent Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 1
- 229960004964 temozolomide Drugs 0.000 description 53
- 210000003491 skin Anatomy 0.000 description 42
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 40
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 238000001819 mass spectrum Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 238000009792 diffusion process Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- 239000003814 drug Substances 0.000 description 10
- 230000008595 infiltration Effects 0.000 description 10
- 238000001764 infiltration Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012466 permeate Substances 0.000 description 9
- 229920002050 silicone resin Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 229920002379 silicone rubber Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 230000004060 metabolic process Effects 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000037317 transdermal delivery Effects 0.000 description 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- 108090000371 Esterases Proteins 0.000 description 3
- JTPUMZTWMWIVPA-UHFFFAOYSA-O Isopropamide Chemical compound C=1C=CC=CC=1C(C(N)=O)(CC[N+](C)(C(C)C)C(C)C)C1=CC=CC=C1 JTPUMZTWMWIVPA-UHFFFAOYSA-O 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000003940 butylamines Chemical class 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 210000002615 epidermis Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 201000001441 melanoma Diseases 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 101000693619 Starmerella bombicola Lactone esterase Proteins 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 2
- 229960003901 dacarbazine Drugs 0.000 description 2
- 238000013016 damping Methods 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
- 229960001737 isopropamide Drugs 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical group CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 150000003941 n-butylamines Chemical class 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 201000000849 skin cancer Diseases 0.000 description 2
- 201000008261 skin carcinoma Diseases 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- DPZMVZIQRMVBBW-UHFFFAOYSA-N 5-Phenyl-1-pentanol Chemical compound OCCCCCC1=CC=CC=C1 DPZMVZIQRMVBBW-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010051779 Bone marrow toxicity Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229960004311 betamethasone valerate Drugs 0.000 description 1
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 231100000366 bone marrow toxicity Toxicity 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical class CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical class CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- OSSQSXOTMIGBCF-UHFFFAOYSA-N non-1-yne Chemical group CCCCCCCC#C OSSQSXOTMIGBCF-UHFFFAOYSA-N 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 230000008591 skin barrier function Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02131346 CN1244583C (zh) | 2002-09-29 | 2002-09-29 | 替莫唑胺-8-羧酸脂和-8-酰胺衍生物,它们的合成方法以及它们在制备抗癌制剂中的应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 02131346 CN1244583C (zh) | 2002-09-29 | 2002-09-29 | 替莫唑胺-8-羧酸脂和-8-酰胺衍生物,它们的合成方法以及它们在制备抗癌制剂中的应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1485327A true CN1485327A (zh) | 2004-03-31 |
CN1244583C CN1244583C (zh) | 2006-03-08 |
Family
ID=34144895
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 02131346 Expired - Lifetime CN1244583C (zh) | 2002-09-29 | 2002-09-29 | 替莫唑胺-8-羧酸脂和-8-酰胺衍生物,它们的合成方法以及它们在制备抗癌制剂中的应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN1244583C (zh) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006024238A1 (fr) * | 2004-09-02 | 2006-03-09 | Tianjin North Pharma Sci-Tech Co., Ltd. | Composition pharmaceutique contenant des esters temozolomide-8-carboxyliques et utilisation des esters temozolomide-8-carboxyliques pour la fabrication de medicaments antitumoraux |
WO2006032190A1 (fr) | 2004-09-22 | 2006-03-30 | Tian Jin Tasly Group Co., Ltd. | Composition pharmaceutique comprenant un ester de temozolomide |
CN1727340B (zh) * | 2004-07-29 | 2011-05-18 | 天津帝士力投资控股集团有限公司 | 一种替莫唑胺-8-羧酸酯及其组合物 |
CN101190916B (zh) * | 2006-11-30 | 2011-06-08 | 天津天士力集团有限公司 | 一种抗癌化合物、其制备方法、用途及含有该化合物的组合物 |
CN110393806A (zh) * | 2019-09-05 | 2019-11-01 | 江苏师范大学 | 一种替莫唑胺聚合物前药及其制备方法与应用 |
US10995094B2 (en) * | 2016-09-22 | 2021-05-04 | The University Of Massachusetts | Temozolomide compounds, polymers prepared therefrom, and method of treating a disease |
-
2002
- 2002-09-29 CN CN 02131346 patent/CN1244583C/zh not_active Expired - Lifetime
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1727340B (zh) * | 2004-07-29 | 2011-05-18 | 天津帝士力投资控股集团有限公司 | 一种替莫唑胺-8-羧酸酯及其组合物 |
WO2006024238A1 (fr) * | 2004-09-02 | 2006-03-09 | Tianjin North Pharma Sci-Tech Co., Ltd. | Composition pharmaceutique contenant des esters temozolomide-8-carboxyliques et utilisation des esters temozolomide-8-carboxyliques pour la fabrication de medicaments antitumoraux |
US7173021B2 (en) * | 2004-09-02 | 2007-02-06 | Tianjin North Pharm Sci-Tech Co., Ltd. | Synthesis of temozolomide esters as potent anticancer pro-drugs for topical and transdermal applications in treatments of cancers |
WO2006032190A1 (fr) | 2004-09-22 | 2006-03-30 | Tian Jin Tasly Group Co., Ltd. | Composition pharmaceutique comprenant un ester de temozolomide |
JP2008513523A (ja) * | 2004-09-22 | 2008-05-01 | ティエンジン テイスリー グループ カンパニー リミティッド | テモゾロマイドエステルよりなる医薬組成物 |
AU2005287799B2 (en) * | 2004-09-22 | 2009-03-26 | Jiangsu Tasly Diyi Pharmaceutical Co., Ltd. | Pharmaceutical composition comprising temozolomide ester |
KR101065984B1 (ko) | 2004-09-22 | 2011-09-19 | 탄진 탈시 그룹 컴퍼니 리미티드 | 테모졸로마이드 에스테르를 포함하는 약학 조성물 |
JP2013028630A (ja) * | 2004-09-22 | 2013-02-07 | Tianjin Tasly Group Co Ltd | テモゾロマイドエステルよりなる医薬組成物 |
CN101190916B (zh) * | 2006-11-30 | 2011-06-08 | 天津天士力集团有限公司 | 一种抗癌化合物、其制备方法、用途及含有该化合物的组合物 |
US10995094B2 (en) * | 2016-09-22 | 2021-05-04 | The University Of Massachusetts | Temozolomide compounds, polymers prepared therefrom, and method of treating a disease |
US11912709B2 (en) | 2016-09-22 | 2024-02-27 | University Of Massachusetts | Temozolomide compounds, polymers prepared therefrom, and method of treating a disease |
CN110393806A (zh) * | 2019-09-05 | 2019-11-01 | 江苏师范大学 | 一种替莫唑胺聚合物前药及其制备方法与应用 |
Also Published As
Publication number | Publication date |
---|---|
CN1244583C (zh) | 2006-03-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1039011C (zh) | 雪花胺衍生物及其制备方法和其作为药剂的用途 | |
KR101363308B1 (ko) | 비만을 치료하기 위한 벤조―융합된 헤테로사이클 설파미드유도체의 용도 | |
CN1678305A (zh) | 卡维地洛磷酸盐和/或其溶剂合物和/或相应组合物和/或治疗方法 | |
CN104356118B (zh) | 多取代吡咯类他汀内酯脱水化合物及其用途 | |
CN1100770C (zh) | 促进水解的紫杉烷疏水性衍生物 | |
CN1089838A (zh) | 一种防治运动病综合征的药物组合物 | |
JP3430322B2 (ja) | スポンギスタチン5、7、8及び9 | |
CN1929829A (zh) | 作为d3激动剂的(s)-2-n-丙基氨基-5-羟基四氢化萘 | |
EP3880680A1 (en) | A crystalline spirocyclic compound inhibitor of tryptophan hydroxylase 1 (tph1) for treating diseases or disorders associated with peripheral serotonin | |
CN1244583C (zh) | 替莫唑胺-8-羧酸脂和-8-酰胺衍生物,它们的合成方法以及它们在制备抗癌制剂中的应用 | |
CN1089336C (zh) | 有抗炎和肌肉松驰活性的秋水仙碱和硫代秋水仙碱衍生物 | |
CN1352545A (zh) | 吲哚衍生物 | |
CN111961097B (zh) | 一种辣椒素类衍生物及其制备方法和在制备心血管疾病的药物中的应用 | |
CN1058706C (zh) | 前列腺素衍生物 | |
CN1726025A (zh) | 作为免疫调节剂和抗癌剂的雷公藤内酯醇衍生物 | |
Krug et al. | Isolation and Synthesis of Tanyolides A and B, Metabolites of the Nudibranch Sclerodoris tanya. | |
WO2013092739A1 (en) | [1,2,4]triazolopyridines and their use as phospodiesterase inhibitors | |
CN1486691A (zh) | 波棱素化合物及其制法和其药物组合物与用途 | |
CN1409714A (zh) | 五环紫杉烷化合物 | |
SA05260060A (ar) | مشتقات1-[ 2 h - بنزوبيران-2-أون-8-يل ] ببرازين لعلاج اضطرابات الحركة | |
CN1088703C (zh) | 水溶性紫杉醇衍生物 | |
CN1012732B (zh) | 偕-二卤代-1,8-二氨基-4-氮杂-辛烷的制备方法 | |
CN1298700C (zh) | 新型假神经酰胺和包含它的化妆品组合物 | |
CN1849312A (zh) | 用作神经营养的具有羟基化长链的生育酚衍生物 | |
EP0346281B1 (de) | Carbamoylierte Hydroxamsäurederivate und Verfahren zu ihrer Herstellung |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee |
Owner name: TASLY HOLDING GROUP CO., LTD. Free format text: FORMER NAME: TIANJIN TASLY GROUP CO., LTD. |
|
CP01 | Change in the name or title of a patent holder |
Address after: 300402 Tianjin Beichen Xinyi white road Liaohe Road No. 1 Patentee after: TASLY HOLDING GROUP Co.,Ltd. Address before: 300402 Tianjin Beichen Xinyi white road Liaohe Road No. 1 Patentee before: Tianjin Tasly Group Co.,Ltd. |
|
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20040331 Assignee: JIANGSU TASLY DIYI PHARMACEUTICAL Co.,Ltd. Assignor: TASLY HOLDING GROUP Co.,Ltd. Contract record no.: 2015320000317 Denomination of invention: Tiemomium azoleamine-8-carboxylic acid ester and 8-amide derivatives,its synthesizing method and application in producing anticancer preparation Granted publication date: 20060308 License type: Exclusive License Record date: 20150508 |
|
LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160727 Address after: 223003 Jiangsu Huaian Qingpu Industrial Park, Chaoyang Road No. 168 Patentee after: JIANGSU TASLY DIYI PHARMACEUTICAL Co.,Ltd. Address before: 300402 Tianjin Beichen Xinyi white road Liaohe Road No. 1 Patentee before: TASLY HOLDING GROUP Co.,Ltd. |
|
CX01 | Expiry of patent term |
Granted publication date: 20060308 |
|
CX01 | Expiry of patent term |