NO791144L - 4-halogenetansyre og derivater derav, samt fremgangsmaate til deres fremstilling - Google Patents
4-halogenetansyre og derivater derav, samt fremgangsmaate til deres fremstillingInfo
- Publication number
- NO791144L NO791144L NO791144A NO791144A NO791144L NO 791144 L NO791144 L NO 791144L NO 791144 A NO791144 A NO 791144A NO 791144 A NO791144 A NO 791144A NO 791144 L NO791144 L NO 791144L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- hydrogen
- carbon atoms
- formula
- fluorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 57
- 238000002360 preparation method Methods 0.000 title claims description 26
- 239000002253 acid Substances 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000000460 chlorine Substances 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000011737 fluorine Substances 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 10
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 230000000699 topical effect Effects 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
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- 239000003937 drug carrier Substances 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 23
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- 239000002904 solvent Substances 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 150000003431 steroids Chemical class 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- -1 n- hexyl Chemical group 0.000 description 15
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- 239000000243 solution Substances 0.000 description 14
- 238000001914 filtration Methods 0.000 description 13
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- 239000011541 reaction mixture Substances 0.000 description 10
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 10
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 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 8
- 239000002674 ointment Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- XHFXMNZYIKFCPN-UHFFFAOYSA-N perchloryl fluoride Chemical compound FCl(=O)(=O)=O XHFXMNZYIKFCPN-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 5
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- ZKLFRQSZDUSMQE-UHFFFAOYSA-N 5,5-dichloroimidazolidine-2,4-dione Chemical compound ClC1(Cl)NC(=O)NC1=O ZKLFRQSZDUSMQE-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- 230000025033 vasoconstriction Effects 0.000 description 4
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- 125000005907 alkyl ester group Chemical group 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- WXURHACBFYSXBI-GQKYHHCASA-N flumethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 1
- BHEKYOLNRIGGLB-UHFFFAOYSA-N tert-butyl n,n'-dicyclohexylcarbamimidate Chemical compound C1CCCCC1N=C(OC(C)(C)C)NC1CCCCC1 BHEKYOLNRIGGLB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J3/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom
- C07J3/005—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by one carbon atom the carbon atom being part of a carboxylic function
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pain & Pain Management (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89364378A | 1978-04-05 | 1978-04-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791144L true NO791144L (no) | 1979-10-08 |
Family
ID=25401852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791144A NO791144L (no) | 1978-04-05 | 1979-04-04 | 4-halogenetansyre og derivater derav, samt fremgangsmaate til deres fremstilling |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0004772A3 (de) |
| JP (1) | JPS54141757A (de) |
| AU (1) | AU4575479A (de) |
| CS (2) | CS208494B2 (de) |
| DK (1) | DK136779A (de) |
| ES (1) | ES479270A1 (de) |
| FI (1) | FI791087A (de) |
| GR (1) | GR65613B (de) |
| IL (1) | IL56990A0 (de) |
| IT (1) | IT7967677A0 (de) |
| NO (1) | NO791144L (de) |
| PL (1) | PL214674A1 (de) |
| PT (1) | PT69411A (de) |
| ZA (1) | ZA791636B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04506066A (ja) * | 1989-06-16 | 1992-10-22 | ジ・アップジョン・カンパニー | 脈管形成を抑制するためのスラミン・タイプの化合物および脈管形成抑止ステロイド類 |
| US5646136A (en) * | 1994-01-04 | 1997-07-08 | Duke University | Methods of inhibiting angiogenesis and tumor growth, and treating ophthalmologic conditions with angiostatic and therapeutic steroids |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636010A (en) * | 1968-12-23 | 1972-01-18 | Ciba Geigy Corp | Esters of steroid-17-carboxylic acids |
| CH628355A5 (de) * | 1976-02-24 | 1982-02-26 | Ciba Geigy Ag | Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren und ihrer ester und salze. |
-
1979
- 1979-03-30 IT IT7967677A patent/IT7967677A0/it unknown
- 1979-03-30 PT PT69411A patent/PT69411A/pt unknown
- 1979-03-31 GR GR58746A patent/GR65613B/el unknown
- 1979-04-02 IL IL56990A patent/IL56990A0/xx unknown
- 1979-04-02 FI FI791087A patent/FI791087A/fi not_active Application Discontinuation
- 1979-04-03 DK DK136779A patent/DK136779A/da unknown
- 1979-04-03 EP EP79300548A patent/EP0004772A3/de not_active Withdrawn
- 1979-04-03 AU AU45754/79A patent/AU4575479A/en not_active Abandoned
- 1979-04-04 CS CS792304A patent/CS208494B2/cs unknown
- 1979-04-04 ES ES479270A patent/ES479270A1/es not_active Expired
- 1979-04-04 CS CS797019A patent/CS208495B2/cs unknown
- 1979-04-04 PL PL21467479A patent/PL214674A1/xx unknown
- 1979-04-04 NO NO791144A patent/NO791144L/no unknown
- 1979-04-05 JP JP4041279A patent/JPS54141757A/ja active Pending
- 1979-04-05 ZA ZA791636A patent/ZA791636B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI791087A (fi) | 1979-10-06 |
| DK136779A (da) | 1979-10-06 |
| AU4575479A (en) | 1979-10-11 |
| IL56990A0 (en) | 1979-07-25 |
| ES479270A1 (es) | 1980-01-16 |
| ZA791636B (en) | 1980-11-26 |
| PL214674A1 (de) | 1980-08-11 |
| CS208495B2 (en) | 1981-09-15 |
| EP0004772A3 (de) | 1979-10-31 |
| PT69411A (en) | 1979-04-01 |
| IT7967677A0 (it) | 1979-03-30 |
| EP0004772A2 (de) | 1979-10-17 |
| CS208494B2 (en) | 1981-09-15 |
| GR65613B (en) | 1980-10-14 |
| JPS54141757A (en) | 1979-11-05 |
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