NO325275B1 - Vandige formuleringer for behandling av krefttumorer samt anvendelse derav. - Google Patents
Vandige formuleringer for behandling av krefttumorer samt anvendelse derav. Download PDFInfo
- Publication number
- NO325275B1 NO325275B1 NO19995109A NO995109A NO325275B1 NO 325275 B1 NO325275 B1 NO 325275B1 NO 19995109 A NO19995109 A NO 19995109A NO 995109 A NO995109 A NO 995109A NO 325275 B1 NO325275 B1 NO 325275B1
- Authority
- NO
- Norway
- Prior art keywords
- tirapazamine
- treatment
- compound
- radiation
- solubility
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 48
- 238000011282 treatment Methods 0.000 title claims abstract description 24
- 201000011510 cancer Diseases 0.000 title claims abstract description 11
- 239000013011 aqueous formulation Substances 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000009472 formulation Methods 0.000 claims abstract description 23
- 239000007979 citrate buffer Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000000872 buffer Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000004959 laryngeal benign neoplasm Diseases 0.000 claims 1
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 2
- GTLQQCMKADHZLK-UHFFFAOYSA-N 1-oxido-1,2,4-benzotriazin-4-ium 4-oxide Chemical class C1=CC=C2N([O-])N=C[N+](=O)C2=C1 GTLQQCMKADHZLK-UHFFFAOYSA-N 0.000 abstract 1
- ORYDPOVDJJZGHQ-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=CC2=[N+]([O-])C(N)=N[N+]([O-])=C21 ORYDPOVDJJZGHQ-UHFFFAOYSA-N 0.000 description 77
- 229950002376 tirapazamine Drugs 0.000 description 75
- 206010021143 Hypoxia Diseases 0.000 description 23
- 230000005855 radiation Effects 0.000 description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- 210000004027 cell Anatomy 0.000 description 20
- 230000001146 hypoxic effect Effects 0.000 description 18
- 239000002904 solvent Substances 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 241000699666 Mus <mouse, genus> Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 210000004881 tumor cell Anatomy 0.000 description 9
- 238000002512 chemotherapy Methods 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 8
- 238000001959 radiotherapy Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 230000000259 anti-tumor effect Effects 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 231100000135 cytotoxicity Toxicity 0.000 description 6
- 230000003013 cytotoxicity Effects 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000007954 hypoxia Effects 0.000 description 5
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical class N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 description 4
- BNZPFJBUHRBLNB-UHFFFAOYSA-N 1-oxido-1,2,4-benzotriazin-1-ium Chemical class C1=CC=C2[N+]([O-])=NC=NC2=C1 BNZPFJBUHRBLNB-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000022534 cell killing Effects 0.000 description 4
- 231100000433 cytotoxic Toxicity 0.000 description 4
- 230000001472 cytotoxic effect Effects 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 3
- 201000008808 Fibrosarcoma Diseases 0.000 description 3
- 208000012766 Growth delay Diseases 0.000 description 3
- 206010040914 Skin reaction Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229960004397 cyclophosphamide Drugs 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000010534 mechanism of action Effects 0.000 description 3
- 229960001924 melphalan Drugs 0.000 description 3
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 239000002534 radiation-sensitizing agent Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 231100000430 skin reaction Toxicity 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000004614 tumor growth Effects 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004820 blood count Methods 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229960005243 carmustine Drugs 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 210000005260 human cell Anatomy 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 239000007972 injectable composition Substances 0.000 description 2
- 210000002414 leg Anatomy 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 229940069328 povidone Drugs 0.000 description 2
- 230000000637 radiosensitizating effect Effects 0.000 description 2
- 230000035483 skin reaction Effects 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 210000000689 upper leg Anatomy 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 1
- YUQABXKDXVGEBK-UHFFFAOYSA-N 3-(2-methoxyethyl)-1-oxido-1,2,4-benzotriazin-4-ium 4-oxide Chemical compound C1=CC=CC2=[N+]([O-])C(CCOC)=N[N+]([O-])=C21 YUQABXKDXVGEBK-UHFFFAOYSA-N 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 230000005778 DNA damage Effects 0.000 description 1
- 231100000277 DNA damage Toxicity 0.000 description 1
- 230000005971 DNA damage repair Effects 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- HRHKSTOGXBBQCB-UHFFFAOYSA-N Mitomycin E Natural products O=C1C(N)=C(C)C(=O)C2=C1C(COC(N)=O)C1(OC)C3N(C)C3CN12 HRHKSTOGXBBQCB-UHFFFAOYSA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 150000001204 N-oxides Chemical group 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 206010039424 Salivary hypersecretion Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012829 chemotherapy agent Substances 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000005782 double-strand break Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- WCDWBPCFGJXFJZ-UHFFFAOYSA-N etanidazole Chemical compound OCCNC(=O)CN1C=CN=C1[N+]([O-])=O WCDWBPCFGJXFJZ-UHFFFAOYSA-N 0.000 description 1
- 229950006566 etanidazole Drugs 0.000 description 1
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
- 238000012395 formulation development Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HRHKSTOGXBBQCB-VFWICMBZSA-N methylmitomycin Chemical compound O=C1C(N)=C(C)C(=O)C2=C1[C@@H](COC(N)=O)[C@@]1(OC)[C@H]3N(C)[C@H]3CN12 HRHKSTOGXBBQCB-VFWICMBZSA-N 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 230000032147 negative regulation of DNA repair Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 230000037311 normal skin Effects 0.000 description 1
- HGASFNYMVGEKTF-UHFFFAOYSA-N octan-1-ol;hydrate Chemical compound O.CCCCCCCCO HGASFNYMVGEKTF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 229950004406 porfiromycin Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000005783 single-strand break Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000012496 stress study Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/837,637 US5827850A (en) | 1995-09-25 | 1997-04-21 | 1,2,4-benzotriazine oxides formulations |
| PCT/US1998/007391 WO1998047512A1 (en) | 1997-04-21 | 1998-04-14 | 1,2,4-benzotriazine oxides formulations |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995109D0 NO995109D0 (no) | 1999-10-20 |
| NO995109L NO995109L (no) | 1999-12-21 |
| NO325275B1 true NO325275B1 (no) | 2008-03-17 |
Family
ID=25275027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995109A NO325275B1 (no) | 1997-04-21 | 1999-10-20 | Vandige formuleringer for behandling av krefttumorer samt anvendelse derav. |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5827850A (https=) |
| EP (1) | EP1044005B1 (https=) |
| JP (1) | JP2001523248A (https=) |
| AT (1) | ATE332139T1 (https=) |
| AU (1) | AU6969098A (https=) |
| BR (1) | BR9808958A (https=) |
| CA (1) | CA2287257C (https=) |
| DE (1) | DE69835167T8 (https=) |
| DK (1) | DK1044005T3 (https=) |
| ES (1) | ES2267183T3 (https=) |
| NO (1) | NO325275B1 (https=) |
| PT (1) | PT1044005E (https=) |
| WO (1) | WO1998047512A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5624925A (en) * | 1986-09-25 | 1997-04-29 | Sri International | 1,2,4-benzotriazine oxides as radiosensitizers and selective cytotoxic agents |
| NZ521436A (en) * | 2002-09-17 | 2005-07-29 | Auckland Uniservices Ltd | DNA- targeted benzotriazine 1,4-dioxides and their use in cancer therapy |
| US20050282814A1 (en) * | 2002-10-03 | 2005-12-22 | Targegen, Inc. | Vasculostatic agents and methods of use thereof |
| CA2456569A1 (en) * | 2003-03-14 | 2004-09-14 | Auckland Uniservices Limited | Benzoazine mono-n-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments |
| KR20070011458A (ko) | 2004-04-08 | 2007-01-24 | 탈자진 인코포레이티드 | 키나제의 벤조트리아진 억제제 |
| PL382308A1 (pl) | 2004-08-25 | 2007-08-20 | Targegen, Inc. | Związki heterocykliczne i sposoby stosowania |
| US7834178B2 (en) * | 2006-03-01 | 2010-11-16 | Bristol-Myers Squibb Company | Triazine 11-beta hydroxysteroid dehydrogenase type 1 inhibitors |
| CN101683346B (zh) * | 2008-09-24 | 2015-04-01 | 杭州民生药业有限公司 | 一种替拉扎明非肠道含水制剂及其制备方法 |
| CN101683319B (zh) * | 2008-09-24 | 2012-09-05 | 杭州民生药业有限公司 | 一种替拉扎明非肠道给药含水制剂及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3980779A (en) * | 1972-02-01 | 1976-09-14 | Bayer Aktiengesellschaft | 3-Amino-1,2,4-benzotriazine-1,4-di-N-oxide compositions and method of using same |
| US4001410A (en) * | 1972-02-01 | 1977-01-04 | Bayer Aktiengesellschaft | 3-amino-1,2,4-benzotriazine-1,4-di-n-oxide compositions and method of using same |
| US5175287A (en) * | 1986-09-25 | 1992-12-29 | S R I International | Process for preparing 1,2,4-benzotriazine oxides |
| DE69636837T2 (de) * | 1995-09-25 | 2007-10-25 | Sanofi-Aventis U.S. Llc | 1,2,4-benzotriazinoxid-formulierungen |
-
1997
- 1997-04-21 US US08/837,637 patent/US5827850A/en not_active Expired - Fee Related
-
1998
- 1998-04-14 ES ES98915529T patent/ES2267183T3/es not_active Expired - Lifetime
- 1998-04-14 AU AU69690/98A patent/AU6969098A/en not_active Abandoned
- 1998-04-14 PT PT98915529T patent/PT1044005E/pt unknown
- 1998-04-14 DE DE69835167T patent/DE69835167T8/de not_active Expired - Fee Related
- 1998-04-14 BR BR9808958-7A patent/BR9808958A/pt not_active Application Discontinuation
- 1998-04-14 CA CA002287257A patent/CA2287257C/en not_active Expired - Fee Related
- 1998-04-14 DK DK98915529T patent/DK1044005T3/da active
- 1998-04-14 JP JP54612298A patent/JP2001523248A/ja not_active Ceased
- 1998-04-14 EP EP98915529A patent/EP1044005B1/en not_active Expired - Lifetime
- 1998-04-14 AT AT98915529T patent/ATE332139T1/de not_active IP Right Cessation
- 1998-04-14 WO PCT/US1998/007391 patent/WO1998047512A1/en not_active Ceased
- 1998-09-21 US US09/157,905 patent/US6153610A/en not_active Expired - Fee Related
-
1999
- 1999-10-20 NO NO19995109A patent/NO325275B1/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT1044005E (pt) | 2006-10-31 |
| EP1044005A4 (en) | 2001-08-08 |
| ATE332139T1 (de) | 2006-07-15 |
| CA2287257A1 (en) | 1998-10-29 |
| DK1044005T3 (da) | 2006-09-25 |
| CA2287257C (en) | 2007-06-12 |
| WO1998047512A1 (en) | 1998-10-29 |
| EP1044005A1 (en) | 2000-10-18 |
| US5827850A (en) | 1998-10-27 |
| US6153610A (en) | 2000-11-28 |
| BR9808958A (pt) | 2000-08-01 |
| DE69835167T2 (de) | 2007-06-06 |
| ES2267183T3 (es) | 2007-03-01 |
| AU6969098A (en) | 1998-11-13 |
| EP1044005B1 (en) | 2006-07-05 |
| DE69835167T8 (de) | 2007-12-06 |
| DE69835167D1 (de) | 2006-08-17 |
| NO995109D0 (no) | 1999-10-20 |
| JP2001523248A (ja) | 2001-11-20 |
| NO995109L (no) | 1999-12-21 |
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