DE2001305C3 - Cytostatisch wirksame Corticosteroid-21 -ester, deren Herstellung sowie diese enthaltende Arzneimittel - Google Patents
Cytostatisch wirksame Corticosteroid-21 -ester, deren Herstellung sowie diese enthaltende ArzneimittelInfo
- Publication number
- DE2001305C3 DE2001305C3 DE2001305A DE2001305A DE2001305C3 DE 2001305 C3 DE2001305 C3 DE 2001305C3 DE 2001305 A DE2001305 A DE 2001305A DE 2001305 A DE2001305 A DE 2001305A DE 2001305 C3 DE2001305 C3 DE 2001305C3
- Authority
- DE
- Germany
- Prior art keywords
- amino
- bis
- chloroethyl
- prednisolone
- small
- 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
Links
- 150000002148 esters Chemical class 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- -1 beta-chloroethyl Chemical group 0.000 claims description 87
- 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 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229960005205 prednisolone Drugs 0.000 claims description 35
- 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 claims description 35
- 238000000034 method Methods 0.000 claims description 24
- 229960000890 hydrocortisone Drugs 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 10
- 229960004618 prednisone Drugs 0.000 claims description 10
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 claims description 7
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 claims description 7
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
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- 125000003545 alkoxy group Chemical group 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 125000001424 substituent group Chemical group 0.000 description 5
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 239000003470 adrenal cortex hormone Substances 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3952/69A GB1272841A (en) | 1969-01-23 | 1969-01-23 | New corticoid steroid compounds of cytostatic interest |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2001305A1 DE2001305A1 (de) | 1970-08-27 |
| DE2001305B2 DE2001305B2 (de) | 1974-08-15 |
| DE2001305C3 true DE2001305C3 (de) | 1975-05-07 |
Family
ID=9767981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2001305A Expired DE2001305C3 (de) | 1969-01-23 | 1970-01-13 | Cytostatisch wirksame Corticosteroid-21 -ester, deren Herstellung sowie diese enthaltende Arzneimittel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3732260A (enExample) |
| AT (1) | AT300212B (enExample) |
| BE (1) | BE744766A (enExample) |
| BR (1) | BR7016251D0 (enExample) |
| CA (1) | CA935152A (enExample) |
| CH (1) | CH534143A (enExample) |
| DE (1) | DE2001305C3 (enExample) |
| DK (1) | DK123713B (enExample) |
| ES (1) | ES375613A1 (enExample) |
| FI (1) | FI47659C (enExample) |
| FR (1) | FR2034483B1 (enExample) |
| GB (1) | GB1272841A (enExample) |
| IE (1) | IE33953B1 (enExample) |
| NL (1) | NL160570C (enExample) |
| NO (1) | NO130476C (enExample) |
| SE (1) | SE358387B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1036870B (it) * | 1975-02-13 | 1979-10-30 | Acraf | Derivati steroidei dell acido bendazolico |
| US4261910A (en) * | 1978-08-14 | 1981-04-14 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the preparation of Chlorambucil derivatives |
| DE3490749C2 (de) * | 1984-07-31 | 1989-12-28 | V Onkologiceskij Naucnyj Centr | 11-Desoxy-17alpha-hydroxycorticosteronester |
| ATE489080T1 (de) * | 2001-06-25 | 2010-12-15 | Ajinomoto Kk | Antitumorale mittel |
| US8790691B2 (en) * | 2008-05-23 | 2014-07-29 | The University Of British Columbia | Modified drugs for use in liposomal nanoparticles |
-
1969
- 1969-01-23 GB GB3952/69A patent/GB1272841A/en not_active Expired
-
1970
- 1970-01-13 NO NO123/70A patent/NO130476C/no unknown
- 1970-01-13 DE DE2001305A patent/DE2001305C3/de not_active Expired
- 1970-01-14 CH CH49670A patent/CH534143A/de not_active IP Right Cessation
- 1970-01-19 US US00004067A patent/US3732260A/en not_active Expired - Lifetime
- 1970-01-19 FI FI700138A patent/FI47659C/fi active
- 1970-01-19 ES ES375613A patent/ES375613A1/es not_active Expired
- 1970-01-20 SE SE00674/70A patent/SE358387B/xx unknown
- 1970-01-21 IE IE80/70A patent/IE33953B1/xx unknown
- 1970-01-21 FR FR7002113A patent/FR2034483B1/fr not_active Expired
- 1970-01-22 BE BE744766D patent/BE744766A/xx not_active IP Right Cessation
- 1970-01-22 CA CA072847A patent/CA935152A/en not_active Expired
- 1970-01-22 DK DK29470AA patent/DK123713B/da not_active IP Right Cessation
- 1970-01-23 NL NL7000977.A patent/NL160570C/xx not_active IP Right Cessation
- 1970-01-23 AT AT64870A patent/AT300212B/de not_active IP Right Cessation
- 1970-01-23 BR BR216251/70A patent/BR7016251D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO130476B (enExample) | 1974-09-09 |
| CA935152A (en) | 1973-10-09 |
| BE744766A (fr) | 1970-07-01 |
| AT300212B (de) | 1972-07-25 |
| FR2034483B1 (enExample) | 1974-02-01 |
| IE33953L (en) | 1970-07-23 |
| CH534143A (de) | 1973-02-28 |
| FR2034483A1 (enExample) | 1970-12-11 |
| FI47659B (enExample) | 1973-10-31 |
| NL160570B (nl) | 1979-06-15 |
| ES375613A1 (es) | 1972-10-16 |
| NL7000977A (enExample) | 1970-07-27 |
| DE2001305A1 (de) | 1970-08-27 |
| FI47659C (fi) | 1974-02-11 |
| NO130476C (enExample) | 1974-12-18 |
| IE33953B1 (en) | 1974-12-30 |
| DE2001305B2 (de) | 1974-08-15 |
| GB1272841A (en) | 1972-05-03 |
| DK123713B (da) | 1972-07-24 |
| SE358387B (enExample) | 1973-07-30 |
| US3732260A (en) | 1973-05-08 |
| BR7016251D0 (pt) | 1973-01-25 |
| NL160570C (nl) | 1979-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: BERENDT, T., DIPL.-CHEM. DR. LEYH, H., DIPL.-ING. DR.-ING., PAT.-ANW., 8000 MUENCHEN |