SE448166B - Derivat av 11-desoxi-17alfa-hydroxikortikosteron - Google Patents
Derivat av 11-desoxi-17alfa-hydroxikortikosteronInfo
- Publication number
- SE448166B SE448166B SE8601344A SE8601344A SE448166B SE 448166 B SE448166 B SE 448166B SE 8601344 A SE8601344 A SE 8601344A SE 8601344 A SE8601344 A SE 8601344A SE 448166 B SE448166 B SE 448166B
- Authority
- SE
- Sweden
- Prior art keywords
- deoxy
- chloroethyl
- hydroxy
- corticosterone
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 51
- 206010028980 Neoplasm Diseases 0.000 description 35
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 22
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 22
- 241001465754 Metazoa Species 0.000 description 17
- UQFHJDVUQSAVOQ-UHFFFAOYSA-N (2-aminophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1N UQFHJDVUQSAVOQ-UHFFFAOYSA-N 0.000 description 15
- 230000000259 anti-tumor effect Effects 0.000 description 15
- 238000011282 treatment Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 210000005075 mammary gland Anatomy 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- RQAFMLCWWGDNLI-UHFFFAOYSA-N 2-[4-[bis(2-chloroethyl)amino]phenyl]acetic acid Chemical group OC(=O)CC1=CC=C(N(CCCl)CCCl)C=C1 RQAFMLCWWGDNLI-UHFFFAOYSA-N 0.000 description 8
- 201000011510 cancer Diseases 0.000 description 8
- 230000002269 spontaneous effect Effects 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 7
- 229960004630 chlorambucil Drugs 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- 239000002253 acid Substances 0.000 description 6
- -1 (2-chloroethyl) -amide pyrenyl acetate Chemical compound 0.000 description 5
- 102000053602 DNA Human genes 0.000 description 5
- 108020004414 DNA Proteins 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 229940088597 hormone Drugs 0.000 description 5
- UIHVAXRVVJJTHU-UHFFFAOYSA-N 2-[bis(2-chloroethyl)amino]acetic acid Chemical group OC(=O)CN(CCCl)CCCl UIHVAXRVVJJTHU-UHFFFAOYSA-N 0.000 description 4
- 102000003676 Glucocorticoid Receptors Human genes 0.000 description 4
- 108090000079 Glucocorticoid Receptors Proteins 0.000 description 4
- HFVNWDWLWUCIHC-GUPDPFMOSA-N Prednimustine Chemical compound O=C([C@@]1(O)CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)[C@@H](O)C[C@@]21C)COC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 HFVNWDWLWUCIHC-GUPDPFMOSA-N 0.000 description 4
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- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 3
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- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 2
- ZHXRJNVLFWPSPO-UHFFFAOYSA-N 2-amino-5-chloro-3-methyl-2-phenylpentanoic acid Chemical compound ClCCC(C(C(=O)O)(C1=CC=CC=C1)N)C ZHXRJNVLFWPSPO-UHFFFAOYSA-N 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
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- 201000009030 Carcinoma Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
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- 238000005917 acylation reaction Methods 0.000 description 2
- 239000003470 adrenal cortex hormone Substances 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 description 2
- 230000001086 cytosolic effect Effects 0.000 description 2
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- 230000001085 cytostatic effect Effects 0.000 description 2
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- ADFOJJHRTBFFOF-RBRWEJTLSA-N estramustine phosphate Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)OP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 ADFOJJHRTBFFOF-RBRWEJTLSA-N 0.000 description 2
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- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
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- 238000002255 vaccination Methods 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- DQDDXBMHFSRJMM-UHFFFAOYSA-N 2-chloroethyl 2-amino-2-phenylacetate Chemical compound NC(C(=O)OCCCl)C1=CC=CC=C1 DQDDXBMHFSRJMM-UHFFFAOYSA-N 0.000 description 1
- HOMSZIFULUHWLN-UHFFFAOYSA-N 2-chloroethylcarbamic acid Chemical compound OC(=O)NCCCl HOMSZIFULUHWLN-UHFFFAOYSA-N 0.000 description 1
- RIZNFWFCXMTRIW-UHFFFAOYSA-N 3-methylbutanoic acid;hydrochloride Chemical compound Cl.CC(C)CC(O)=O RIZNFWFCXMTRIW-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- 108010077544 Chromatin Proteins 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 241000766026 Coregonus nasus Species 0.000 description 1
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- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010059024 Gastrointestinal toxicity Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 1
- 241000272041 Naja Species 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
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- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- 230000004727 humoral immunity Effects 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
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- 230000005923 long-lasting effect Effects 0.000 description 1
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- 201000005296 lung carcinoma Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002395 mineralocorticoid Substances 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- 229940037129 plain mineralocorticoids for systemic use Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
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- 206010073373 small intestine adenocarcinoma Diseases 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of only two carbon atoms, e.g. pregnane derivatives
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/SU1984/000043 WO1986000908A1 (fr) | 1984-07-31 | 1984-07-31 | DERIVES DE 11-DESOXY-17alpha-OXYCORTICOSTERONE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8601344D0 SE8601344D0 (sv) | 1986-03-21 |
| SE8601344L SE8601344L (sv) | 1986-03-21 |
| SE448166B true SE448166B (sv) | 1987-01-26 |
Family
ID=21616860
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8601344A SE448166B (sv) | 1984-07-31 | 1986-03-21 | Derivat av 11-desoxi-17alfa-hydroxikortikosteron |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4810701A (enExample) |
| JP (1) | JPH01500111A (enExample) |
| CH (1) | CH666044A5 (enExample) |
| DE (2) | DE3490749C2 (enExample) |
| FI (1) | FI80048C (enExample) |
| GB (1) | GB2176189B (enExample) |
| SE (1) | SE448166B (enExample) |
| WO (1) | WO1986000908A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4933332A (en) * | 1986-03-21 | 1990-06-12 | Kurdjumova Kira N | 11-desoxy-17-α-hydroxycorticosterone derivatives |
| US5483697A (en) * | 1989-05-22 | 1996-01-16 | Board Of Regents The University Of Texas | Multilayer protective coverings with a sealing solution |
| AP141A (en) * | 1990-04-25 | 1991-08-25 | Richter Gedeon Vegyeszet | Novel steroid doils. |
| AU1773892A (en) * | 1991-04-09 | 1992-11-17 | Upjohn Company, The | Use of amines to sensitize multidrug-resistant cells |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1793461A1 (de) * | 1968-09-20 | 1971-07-01 | Hoechst Ag | 21-(Cyclobutyl-carbonsaeure)-ester von Steroidderivaten und Verfahren zu ihrer Herstellung |
| GB1272841A (en) * | 1969-01-23 | 1972-05-03 | Leo Ab | New corticoid steroid compounds of cytostatic interest |
| GB1558472A (en) * | 1976-01-22 | 1980-01-03 | Leo Ab | 17-esters of 17- hydroxy gestogens |
| US4261910A (en) * | 1978-08-14 | 1981-04-14 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the preparation of Chlorambucil derivatives |
-
1984
- 1984-07-31 US US06/852,459 patent/US4810701A/en not_active Expired - Fee Related
- 1984-07-31 GB GB08606415A patent/GB2176189B/en not_active Expired
- 1984-07-31 WO PCT/SU1984/000043 patent/WO1986000908A1/ru not_active Ceased
- 1984-07-31 JP JP59503853A patent/JPH01500111A/ja active Granted
- 1984-07-31 DE DE19843490749 patent/DE3490749C2/de not_active Expired
- 1984-07-31 DE DE19843490749 patent/DE3490749T1/de active Pending
- 1984-07-31 CH CH1341/86A patent/CH666044A5/de not_active IP Right Cessation
-
1986
- 1986-03-21 SE SE8601344A patent/SE448166B/sv not_active IP Right Cessation
- 1986-03-26 FI FI861325A patent/FI80048C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1986000908A1 (fr) | 1986-02-13 |
| FI80048C (fi) | 1990-04-10 |
| FI861325L (fi) | 1986-03-26 |
| FI80048B (fi) | 1989-12-29 |
| JPH0124160B2 (enExample) | 1989-05-10 |
| CH666044A5 (de) | 1988-06-30 |
| DE3490749T1 (de) | 1986-08-07 |
| SE8601344D0 (sv) | 1986-03-21 |
| DE3490749C2 (de) | 1989-12-28 |
| US4810701A (en) | 1989-03-07 |
| GB2176189B (en) | 1988-03-02 |
| GB8606415D0 (en) | 1986-04-23 |
| SE8601344L (sv) | 1986-03-21 |
| GB2176189A (en) | 1986-12-17 |
| JPH01500111A (ja) | 1989-01-19 |
| FI861325A0 (fi) | 1986-03-26 |
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|---|---|---|---|
| NUG | Patent has lapsed |
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