NO318648B1 - Anvendelse av 6-substituerte acylfulvenanaloger som har antitumorvirkning - Google Patents
Anvendelse av 6-substituerte acylfulvenanaloger som har antitumorvirkning Download PDFInfo
- Publication number
- NO318648B1 NO318648B1 NO19953099A NO953099A NO318648B1 NO 318648 B1 NO318648 B1 NO 318648B1 NO 19953099 A NO19953099 A NO 19953099A NO 953099 A NO953099 A NO 953099A NO 318648 B1 NO318648 B1 NO 318648B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- tumor
- stated
- cell
- acylfulvene
- Prior art date
Links
- 230000000259 anti-tumor effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims abstract description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims abstract description 4
- 208000000389 T-cell leukemia Diseases 0.000 claims abstract description 4
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 claims abstract description 4
- 201000008275 breast carcinoma Diseases 0.000 claims abstract description 4
- 201000005296 lung carcinoma Diseases 0.000 claims abstract description 4
- 239000003937 drug carrier Substances 0.000 claims abstract 4
- 206010028980 Neoplasm Diseases 0.000 claims description 25
- 239000003814 drug Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 10
- -1 p-methoxybenzyl Chemical group 0.000 claims description 10
- 230000004614 tumor growth Effects 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000001990 intravenous administration Methods 0.000 claims description 4
- 238000007912 intraperitoneal administration Methods 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 230000002611 ovarian Effects 0.000 claims description 3
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
- 201000000050 myeloid neoplasm Diseases 0.000 claims 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 abstract description 9
- 230000005764 inhibitory process Effects 0.000 abstract description 4
- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- 230000004565 tumor cell growth Effects 0.000 abstract description 3
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 210000004027 cell Anatomy 0.000 abstract 5
- 208000025113 myeloid leukemia Diseases 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 25
- QVMDIQLUNODCTG-UHFFFAOYSA-N (3'R)-3'r,6't-Dihydroxy-2',2',4',6'c-tetramethyl-2',3'-dihydro-spiro[cyclopropan-1,5'-inden]-7'-on Natural products CC1=C2C(O)C(C)(C)C=C2C(=O)C(C)(O)C11CC1 QVMDIQLUNODCTG-UHFFFAOYSA-N 0.000 description 24
- HLAKJNQXUARACO-ZDUSSCGKSA-N (5'r)-5'-hydroxy-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one Chemical class O=C([C@@]1(O)C)C2=CC(C)=CC2=C(C)C21CC2 HLAKJNQXUARACO-ZDUSSCGKSA-N 0.000 description 20
- AKYKZQWKCBEJHI-UHFFFAOYSA-N Illudin S Natural products CC1=C2C(O)C(C)(CO)C=C2C(=O)C(O)C13CC3 AKYKZQWKCBEJHI-UHFFFAOYSA-N 0.000 description 18
- DDLLIYKVDWPHJI-UHFFFAOYSA-N Lampterol Natural products CC1=C2C(O)C(C)(CO)C=C2C(=O)C(C)(O)C11CC1 DDLLIYKVDWPHJI-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- DDLLIYKVDWPHJI-RDBSUJKOSA-N Illudin S Chemical compound C12([C@@](C)(O)C(=O)C3=C[C@@](C)(CO)[C@H](O)C3=C2C)CC1 DDLLIYKVDWPHJI-RDBSUJKOSA-N 0.000 description 17
- NICJCIQSJJKZAH-AWEZNQCLSA-N irofulven Chemical compound O=C([C@@]1(O)C)C2=CC(C)=C(CO)C2=C(C)C21CC2 NICJCIQSJJKZAH-AWEZNQCLSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229950005254 irofulven Drugs 0.000 description 12
- 239000002246 antineoplastic agent Substances 0.000 description 11
- 229930012538 Paclitaxel Natural products 0.000 description 10
- 229960001592 paclitaxel Drugs 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 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 10
- HLAKJNQXUARACO-UHFFFAOYSA-N acylfulvene Natural products CC1(O)C(=O)C2=CC(C)=CC2=C(C)C21CC2 HLAKJNQXUARACO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 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 8
- 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 8
- 229930190064 illudin Natural products 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QVMDIQLUNODCTG-OCCSQVGLSA-N Illudin M Chemical compound C12([C@@](C)(O)C(=O)C3=CC(C)(C)[C@H](O)C3=C2C)CC1 QVMDIQLUNODCTG-OCCSQVGLSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 231100000419 toxicity Toxicity 0.000 description 6
- 230000001988 toxicity Effects 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229940127089 cytotoxic agent Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 229960004857 mitomycin Drugs 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 229940009456 adriamycin Drugs 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 231100001274 therapeutic index Toxicity 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- NICVUHKZCHQOBC-UHFFFAOYSA-N (5-methylidenecyclopenta-1,3-dien-1-yl)methanol Chemical compound OCC1=CC=CC1=C NICVUHKZCHQOBC-UHFFFAOYSA-N 0.000 description 3
- TURODGSNSRINTH-UHFFFAOYSA-N 4-[(5-methylidenecyclopenta-1,3-dien-1-yl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC1=C TURODGSNSRINTH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 3
- 206010059866 Drug resistance Diseases 0.000 description 3
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 3
- 206010070863 Toxicity to various agents Diseases 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 201000005249 lung adenocarcinoma Diseases 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 229930192392 Mitomycin Natural products 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000002456 taxol group Chemical group 0.000 description 2
- 238000006257 total synthesis reaction Methods 0.000 description 2
- GQMNUIIAPHOQJZ-ZDUSSCGKSA-N (5'r)-5'-hydroxy-1'-iodo-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one Chemical class O=C([C@@]1(O)C)C2=CC(C)=C(I)C2=C(C)C21CC2 GQMNUIIAPHOQJZ-ZDUSSCGKSA-N 0.000 description 1
- KLELEQGKTUGEPV-UHFFFAOYSA-N 1-(1-acetylcyclopropyl)ethanone Chemical compound CC(=O)C1(C(C)=O)CC1 KLELEQGKTUGEPV-UHFFFAOYSA-N 0.000 description 1
- YORMDTTYGSNHDZ-UHFFFAOYSA-N 1-bromo-5-methylidenecyclopenta-1,3-diene Chemical compound BrC1=CC=CC1=C YORMDTTYGSNHDZ-UHFFFAOYSA-N 0.000 description 1
- GLVCTBCUWWSFTM-UHFFFAOYSA-N 1-iodo-5-methylidenecyclopenta-1,3-diene Chemical compound IC1=CC=CC1=C GLVCTBCUWWSFTM-UHFFFAOYSA-N 0.000 description 1
- GGBPFSSFAIWWFL-UHFFFAOYSA-N 2-cyclopenta-2,4-dien-1-ylideneethanol Chemical compound OCC=C1C=CC=C1 GGBPFSSFAIWWFL-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001480079 Corymbia calophylla Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical group ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 235000006552 Liquidambar styraciflua Nutrition 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241001674286 Omphalotus illudens Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 206010066901 Treatment failure Diseases 0.000 description 1
- 206010064390 Tumour invasion Diseases 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000000735 allogeneic effect Effects 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010322 bone marrow transplantation Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 230000009400 cancer invasion Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000007877 drug screening Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Chemical group 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical compound O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 238000012606 in vitro cell culture Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011395 multi-agent chemotherapy Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 231100000916 relative toxicity Toxicity 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- 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
- A61K31/12—Ketones
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
- C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
- C07C49/737—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/015,179 US5439936A (en) | 1989-10-03 | 1993-02-09 | Method of treating certain tumors using illudin analogs |
PCT/US1994/001232 WO1994018151A1 (en) | 1993-02-09 | 1994-02-02 | Acylfulvene analogues as antitumor agents |
Publications (3)
Publication Number | Publication Date |
---|---|
NO953099D0 NO953099D0 (no) | 1995-08-07 |
NO953099L NO953099L (no) | 1995-10-09 |
NO318648B1 true NO318648B1 (no) | 2005-04-25 |
Family
ID=21769946
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19953099A NO318648B1 (no) | 1993-02-09 | 1995-08-07 | Anvendelse av 6-substituerte acylfulvenanaloger som har antitumorvirkning |
Country Status (22)
Country | Link |
---|---|
US (3) | US5439936A (zh) |
EP (1) | EP0683762B1 (zh) |
JP (1) | JP3908270B2 (zh) |
KR (1) | KR100311327B1 (zh) |
CN (1) | CN1046934C (zh) |
AT (1) | ATE174894T1 (zh) |
AU (1) | AU676889B2 (zh) |
BR (1) | BR9405689A (zh) |
CA (1) | CA2155329C (zh) |
CZ (1) | CZ288596B6 (zh) |
DE (1) | DE69415507T2 (zh) |
DK (1) | DK0683762T3 (zh) |
ES (1) | ES2125441T3 (zh) |
GR (1) | GR3029736T3 (zh) |
HU (1) | HU220059B (zh) |
MD (1) | MD1418G2 (zh) |
NO (1) | NO318648B1 (zh) |
NZ (1) | NZ262282A (zh) |
PL (1) | PL175024B1 (zh) |
RU (1) | RU2145849C1 (zh) |
TJ (1) | TJ266B (zh) |
WO (1) | WO1994018151A1 (zh) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5932553A (en) * | 1996-07-18 | 1999-08-03 | The Regents Of The University Of California | Illudin analogs useful as antitumor agents |
US5723632A (en) * | 1996-08-08 | 1998-03-03 | Mgi Pharma, Inc. | Total synthesis of antitumor acylfulvenes |
US7141603B2 (en) * | 1999-02-19 | 2006-11-28 | The Regents Of The University California | Antitumor agents |
US6025328A (en) * | 1998-02-20 | 2000-02-15 | The Regents Of The University Of California | Antitumor agents |
US6436916B1 (en) | 2000-10-12 | 2002-08-20 | Alvin Guttag | Ibuprofen-aspirin and hydroxymethylacylfulvene analogs |
US7015247B2 (en) * | 2000-10-12 | 2006-03-21 | Alvin Guttag | Ibuprofen-aspirin, hydroxymethylacylfulvene analogs and L-sugar illudin analogs |
EP2277595A3 (en) | 2004-06-24 | 2011-09-28 | Novartis Vaccines and Diagnostics, Inc. | Compounds for immunopotentiation |
WO2007019308A2 (en) * | 2005-08-03 | 2007-02-15 | The Regents Of The University Of California | Illudin analogs useful as anticancer agents |
NZ594236A (en) * | 2009-01-26 | 2014-08-29 | Univ Taipei Medical | Use of pterosin compounds for treating diabetes and obesity |
US10285955B2 (en) | 2014-04-10 | 2019-05-14 | Af Chemicals, Llc | Affinity medicant conjugate |
US11135182B2 (en) | 2014-04-10 | 2021-10-05 | Af Chemicals, Llc | Affinity medicant conjugates |
EP4257186A3 (en) | 2014-04-10 | 2023-11-15 | AF Chemicals LLC | Affinity medicant conjugates |
CN106083953A (zh) * | 2016-06-15 | 2016-11-09 | 成都医学院 | 一种从蕨菜中提取原蕨苷以及制备高纯度原蕨苷的方法 |
WO2018170230A1 (en) * | 2017-03-15 | 2018-09-20 | Memorial Sloan Kettering Cancer Center | Diagnosis & treatment of ercc3-mutant cancer |
CN112804995A (zh) * | 2018-09-04 | 2021-05-14 | 蓝腾制药公司 | 隐杯伞素类似物、其应用及其合成方法 |
EP3667323A1 (en) | 2018-12-11 | 2020-06-17 | Kelner, Michael | Methods, compositions and devices for treating cancer with illudofulvenes |
RU2738848C1 (ru) * | 2019-10-24 | 2020-12-17 | Общество с ограниченной ответственностью "Научно-исследовательский институт ХимРар" (ООО "НИИ ХимРар") | Ингибитор вируса гепатита В (ВГВ), представляющий собой производные N-{ 3-[6-(диалкиламино)пиридазин-3-ил]фенил} арилсульфонамида и производные N-{ 4-[6-(диалкиламино)пиридазин-3-ил]фенил} арилсульфонамида |
US11591295B2 (en) | 2019-11-25 | 2023-02-28 | Af Chemicals Llc | Affinity illudofulvene conjugates |
EP4035684A1 (en) | 2019-11-25 | 2022-08-03 | AF Chemical LLC | Affinity illudofulvene conjugates |
CN112972443A (zh) * | 2021-03-29 | 2021-06-18 | 杭州添帆生物科技有限公司 | 一种抗癌药物及其应用 |
WO2023239821A2 (en) * | 2022-06-07 | 2023-12-14 | Lantern Pharma Inc. | Treating cancers with combinations of acylfulvenes with ibrutinib or bortezomib |
WO2024016014A2 (en) * | 2022-07-15 | 2024-01-18 | Lantern Pharma Inc. | Method for treating breast cancers and parp resistant breast cancers |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2091249T3 (es) * | 1989-10-03 | 1996-11-01 | Univ California | Analogos de iludina utilizables como agentes antitumorales. |
GB9017024D0 (en) * | 1990-08-03 | 1990-09-19 | Erba Carlo Spa | New linker for bioactive agents |
FI85318C (fi) * | 1990-08-14 | 1992-03-25 | Tecnomen Oy | Kompensering av felet i en klockas gaong. |
JPH06223404A (ja) * | 1993-01-25 | 1994-08-12 | Mitsubishi Kasei Corp | 光学的情報記録用媒体 |
-
1993
- 1993-02-09 US US08/015,179 patent/US5439936A/en not_active Expired - Lifetime
-
1994
- 1994-02-02 HU HU9502358A patent/HU220059B/hu not_active IP Right Cessation
- 1994-02-02 EP EP94908702A patent/EP0683762B1/en not_active Expired - Lifetime
- 1994-02-02 CN CN94191560A patent/CN1046934C/zh not_active Expired - Fee Related
- 1994-02-02 PL PL94310159A patent/PL175024B1/pl not_active IP Right Cessation
- 1994-02-02 MD MD96-0212A patent/MD1418G2/ro not_active IP Right Cessation
- 1994-02-02 TJ TJ96000336A patent/TJ266B/xx unknown
- 1994-02-02 AT AT94908702T patent/ATE174894T1/de not_active IP Right Cessation
- 1994-02-02 RU RU95121694A patent/RU2145849C1/ru not_active IP Right Cessation
- 1994-02-02 JP JP51820894A patent/JP3908270B2/ja not_active Expired - Fee Related
- 1994-02-02 ES ES94908702T patent/ES2125441T3/es not_active Expired - Lifetime
- 1994-02-02 KR KR1019950703280A patent/KR100311327B1/ko not_active IP Right Cessation
- 1994-02-02 AU AU61700/94A patent/AU676889B2/en not_active Ceased
- 1994-02-02 CA CA002155329A patent/CA2155329C/en not_active Expired - Fee Related
- 1994-02-02 DE DE69415507T patent/DE69415507T2/de not_active Expired - Lifetime
- 1994-02-02 NZ NZ262282A patent/NZ262282A/en not_active IP Right Cessation
- 1994-02-02 WO PCT/US1994/001232 patent/WO1994018151A1/en active IP Right Grant
- 1994-02-02 BR BR9405689A patent/BR9405689A/pt not_active Application Discontinuation
- 1994-02-02 CZ CZ19951986A patent/CZ288596B6/cs not_active IP Right Cessation
- 1994-02-02 DK DK94908702T patent/DK0683762T3/da active
- 1994-07-15 US US08/276,169 patent/US5563176A/en not_active Expired - Lifetime
- 1994-11-01 US US08/332,940 patent/US5523490A/en not_active Expired - Lifetime
-
1995
- 1995-08-07 NO NO19953099A patent/NO318648B1/no not_active IP Right Cessation
-
1999
- 1999-03-19 GR GR990400821T patent/GR3029736T3/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO318648B1 (no) | Anvendelse av 6-substituerte acylfulvenanaloger som har antitumorvirkning | |
JPS59225150A (ja) | 殺生物性芳香族化合物、その合成および医薬としてのその使用 | |
CA2833780C (en) | Prenylated hydroxystilbenes | |
JP2007517861A (ja) | カンナビノイドのキノン派生物の治療使用方法 | |
US20080233208A1 (en) | Use of erianin in preparing pharmaceutical for treating tumors | |
JPH05503077A (ja) | 抗腫瘍剤としてのイルージンアナログ | |
US20190077808A1 (en) | 4-azapodophylotoxins compounds | |
JP2016539956A (ja) | ゲムシタビン誘導体、該誘導体を含む組成物及び該誘導体の製薬用途 | |
KR100406736B1 (ko) | 나프토퀴논계 화합물을 포함하는 항암제 | |
US7632863B2 (en) | 3,4,5,4′-tetramethoxyl-α,β-diphenylethane-3′-O-sodium sulphate and its use | |
JPH02311462A (ja) | 制ガン剤ならびに制ガン剤として有用な新規複素環化合物またはそれらの塩 | |
WO2004080455A1 (ja) | 抗菌剤と抗ガン剤 | |
JP2007521337A (ja) | 癌治療に有効なピラノン誘導体 | |
CN110590778A (zh) | 3,10二对甲氧基苯基6,12二氮杂四高立方烷类化合物及合成方法应用和药物组合物 | |
EA000166B1 (ru) | Биологически активные уреидо-производные, полезные при лечении рассеянного склероза | |
FI90075B (fi) | Foerfarande foer framstaellning av ett terapeutiskt aktivt 1,3,5-tritianderivat substituerat i position 2 | |
JPS6040423B2 (ja) | ユーフエニル―2,3,4,5―テトラヒドロ―1h―3―ベンズアゼピン類 | |
US11142539B2 (en) | Phosphinogold(I) complexes and methods of treating cancer | |
Hemalatha et al. | Crystal structure, Hirshfeld surfaces and energy framework studies of a biologically active compound (3E)-3-(2, 3, 4-trimethoxyphenyl) methylidene)-2, 3-dihydro-4H-1-benzopyran-4-one | |
US5494930A (en) | Caribenolide I | |
JPS62500453A (ja) | ピロチン誘導体の使用 | |
Avula et al. | New 1H-1, 2, 3-triazole analogues of boswellic acid are potential anti-breast cancer agents | |
WO2022232109A1 (en) | Synthesis of cbn and cbnv | |
KR100501843B1 (ko) | 새로운 항암성 비타민 d₃유도체 | |
CN101157628A (zh) | 一类取代苯甲酸类含氮衍生物及其抗肿瘤医药用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |