CA1333771C - Use of imexon as an immune suppressive and pharmaceutical compositions containing them - Google Patents
Use of imexon as an immune suppressive and pharmaceutical compositions containing themInfo
- Publication number
- CA1333771C CA1333771C CA000606620A CA606620A CA1333771C CA 1333771 C CA1333771 C CA 1333771C CA 000606620 A CA000606620 A CA 000606620A CA 606620 A CA606620 A CA 606620A CA 1333771 C CA1333771 C CA 1333771C
- Authority
- CA
- Canada
- Prior art keywords
- imexon
- pharmaceutical composition
- acid addition
- addition salt
- acceptable acid
- 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.)
- Expired - Fee Related
Links
- BIXBBIPTYBJTRY-UHFFFAOYSA-N imexon Chemical compound NC1=NC(=O)N2CC12 BIXBBIPTYBJTRY-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 229950003978 imexon Drugs 0.000 title claims abstract description 71
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 41
- 230000006028 immune-suppresssive effect Effects 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 210000003719 b-lymphocyte Anatomy 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 239000011149 active material Substances 0.000 claims abstract description 14
- 230000001506 immunosuppresive effect Effects 0.000 claims abstract description 14
- 230000004913 activation Effects 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 230000035755 proliferation Effects 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 208000023275 Autoimmune disease Diseases 0.000 claims description 11
- 206010001513 AIDS related complex Diseases 0.000 claims description 10
- 208000030507 AIDS Diseases 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 230000001629 suppression Effects 0.000 claims description 7
- 206010038997 Retroviral infections Diseases 0.000 claims description 6
- 208000036142 Viral infection Diseases 0.000 claims description 6
- 230000009826 neoplastic cell growth Effects 0.000 claims description 6
- 210000004180 plasmocyte Anatomy 0.000 claims description 6
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 5
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 5
- 230000000798 anti-retroviral effect Effects 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 208000032839 leukemia Diseases 0.000 claims description 5
- 201000011649 lymphoblastic lymphoma Diseases 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000003612 virological effect Effects 0.000 claims description 5
- 206010025323 Lymphomas Diseases 0.000 claims description 4
- 230000001085 cytostatic effect Effects 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims 5
- 208000004736 B-Cell Leukemia Diseases 0.000 claims 2
- 208000003950 B-cell lymphoma Diseases 0.000 claims 2
- 230000000840 anti-viral effect Effects 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 10
- 108010062580 Concanavalin A Proteins 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 210000004698 lymphocyte Anatomy 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229960004397 cyclophosphamide Drugs 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 206010039491 Sarcoma Diseases 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 210000001744 T-lymphocyte Anatomy 0.000 description 3
- 230000003460 anti-nuclear Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003102 growth factor Substances 0.000 description 3
- 230000008629 immune suppression Effects 0.000 description 3
- 229940125721 immunosuppressive agent Drugs 0.000 description 3
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229930105110 Cyclosporin A Natural products 0.000 description 2
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 2
- 108010036949 Cyclosporine Proteins 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 201000008808 Fibrosarcoma Diseases 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- PPQNQXQZIWHJRB-UHFFFAOYSA-N Methylcholanthrene Chemical compound C1=CC=C2C3=CC4=CC=C(C)C(CC5)=C4C5=C3C=CC2=C1 PPQNQXQZIWHJRB-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000714180 Rauscher mink cell focus-forming virus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000024932 T cell mediated immunity Effects 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
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- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229960001265 ciclosporin Drugs 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
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- 239000003814 drug Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000012797 qualification Methods 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000004989 spleen cell Anatomy 0.000 description 2
- 210000004988 splenocyte Anatomy 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- KOYMTVWMCXDJNV-UHFFFAOYSA-N 1-[(2-methoxy-6-methylpyridin-3-yl)methyl]aziridine-2-carbonitrile Chemical compound COC1=NC(C)=CC=C1CN1C(C#N)C1 KOYMTVWMCXDJNV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 1
- 230000003844 B-cell-activation Effects 0.000 description 1
- 208000011691 Burkitt lymphomas Diseases 0.000 description 1
- 108010036941 Cyclosporins Proteins 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- HCIHJOTZGZSMLV-UHFFFAOYSA-N Lutinine Natural products O=C1C(=Nc2ccccc2)C=C(Nc3ccccc3)c4ccccc14 HCIHJOTZGZSMLV-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 208000007452 Plasmacytoma Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010058874 Viraemia Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000000781 anti-lymphocytic effect Effects 0.000 description 1
- 229940045686 antimetabolites antineoplastic purine analogs Drugs 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000001516 cell proliferation assay Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
- 229950003453 ciamexon Drugs 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- -1 cyclo-phosphamide Chemical class 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 239000004052 folic acid antagonist Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000008076 immune mechanism Effects 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000035752 proliferative phase Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000002226 simultaneous effect Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229960002555 zidovudine Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Prostheses (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3825667A DE3825667A1 (de) | 1988-07-28 | 1988-07-28 | Verwendung von imexon als immunsuppressivum |
| DEP3825667.3 | 1988-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1333771C true CA1333771C (en) | 1995-01-03 |
Family
ID=6359767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000606620A Expired - Fee Related CA1333771C (en) | 1988-07-28 | 1989-07-25 | Use of imexon as an immune suppressive and pharmaceutical compositions containing them |
Country Status (14)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200604579B (en) * | 2003-12-08 | 2007-10-31 | Univ Arizona | Synergistic anti-cancer compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2528460A1 (de) * | 1975-06-26 | 1977-01-13 | Boehringer Mannheim Gmbh | Verwendung von l-carboxamido-2- cyan-aziridin als immunstimulans |
| DE2530398A1 (de) * | 1975-07-08 | 1977-01-27 | Boehringer Mannheim Gmbh | Organische verbindung |
| DE2736296A1 (de) * | 1977-08-12 | 1979-02-22 | Boehringer Mannheim Gmbh | Verwendung von 2-cyan-aziridin und seinen derivaten zur immunstimulierung |
-
1988
- 1988-07-28 DE DE3825667A patent/DE3825667A1/de active Granted
-
1989
- 1989-07-21 PH PH38984A patent/PH26684A/en unknown
- 1989-07-21 EP EP89113425A patent/EP0352652B1/de not_active Expired - Lifetime
- 1989-07-21 AT AT89113425T patent/ATE117551T1/de not_active IP Right Cessation
- 1989-07-21 DE DE58908926T patent/DE58908926D1/de not_active Expired - Fee Related
- 1989-07-21 DK DK198903633A patent/DK175199B1/da not_active IP Right Cessation
- 1989-07-24 AU AU38877/89A patent/AU619027B2/en not_active Ceased
- 1989-07-25 CA CA000606620A patent/CA1333771C/en not_active Expired - Fee Related
- 1989-07-27 PT PT91293A patent/PT91293B/pt not_active IP Right Cessation
- 1989-07-27 ZA ZA895710A patent/ZA895710B/xx unknown
- 1989-07-27 IE IE244889A patent/IE66680B1/en not_active IP Right Cessation
- 1989-07-27 HU HU893821A patent/HU206827B/hu not_active IP Right Cessation
- 1989-07-27 IL IL9113889A patent/IL91138A/en not_active IP Right Cessation
- 1989-07-28 KR KR1019890010705A patent/KR0135757B1/ko not_active Expired - Fee Related
- 1989-07-28 JP JP1194417A patent/JP2848634B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK363389D0 (da) | 1989-07-21 |
| DK175199B1 (da) | 2004-07-05 |
| PT91293A (pt) | 1990-02-08 |
| IL91138A0 (en) | 1990-03-19 |
| AU619027B2 (en) | 1992-01-16 |
| DK363389A (da) | 1990-01-29 |
| HUT52378A (en) | 1990-07-28 |
| IE66680B1 (en) | 1996-01-24 |
| JPH0288521A (ja) | 1990-03-28 |
| JP2848634B2 (ja) | 1999-01-20 |
| KR0135757B1 (ko) | 1998-04-23 |
| EP0352652A3 (de) | 1991-09-04 |
| DE3825667A1 (de) | 1990-03-15 |
| HU206827B (en) | 1993-01-28 |
| IE892448L (en) | 1990-01-28 |
| PH26684A (en) | 1992-09-15 |
| IL91138A (en) | 1994-10-21 |
| DE58908926D1 (de) | 1995-03-09 |
| AU3887789A (en) | 1990-02-01 |
| ZA895710B (en) | 1990-04-25 |
| ATE117551T1 (de) | 1995-02-15 |
| EP0352652B1 (de) | 1995-01-25 |
| KR900001369A (ko) | 1990-02-27 |
| PT91293B (pt) | 1995-03-01 |
| EP0352652A2 (de) | 1990-01-31 |
| DE3825667C2 (enrdf_load_stackoverflow) | 1991-06-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |