NO122644B - - Google Patents
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- Publication number
- NO122644B NO122644B NO146141A NO14614162A NO122644B NO 122644 B NO122644 B NO 122644B NO 146141 A NO146141 A NO 146141A NO 14614162 A NO14614162 A NO 14614162A NO 122644 B NO122644 B NO 122644B
- Authority
- NO
- Norway
- Prior art keywords
- bis
- benzoquinone
- starting materials
- acylamino
- benzoquinones
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- KKSCCSVQHNQDBX-UHFFFAOYSA-N n-[2,5-dichloro-3,6-dioxo-4-(propanoylamino)cyclohexa-1,4-dien-1-yl]propanamide Chemical compound CCC(=O)NC1=C(Cl)C(=O)C(NC(=O)CC)=C(Cl)C1=O KKSCCSVQHNQDBX-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 ethylene imino group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QLHPOTDBWHTTBM-UHFFFAOYSA-N 2,5-diamino-3,6-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound NC1=C(Cl)C(=O)C(N)=C(Cl)C1=O QLHPOTDBWHTTBM-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- RCDDYOVHUCQAMN-UHFFFAOYSA-N N-[4-(butanoylamino)-2,5-dichloro-3,6-dioxocyclohexa-1,4-dien-1-yl]butanamide Chemical compound ClC=1C(C(=C(C(C1NC(CCC)=O)=O)Cl)NC(CCC)=O)=O RCDDYOVHUCQAMN-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 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
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000224421 Heterolobosea Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- RFUGMORVSDZBLC-UHFFFAOYSA-N [Na].CC(N)=O Chemical compound [Na].CC(N)=O RFUGMORVSDZBLC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 210000003001 amoeba Anatomy 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940007078 entamoeba histolytica Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- ZYWQUADTNKEZKA-UHFFFAOYSA-N n-(4-acetamido-2,5-dichloro-3,6-dioxocyclohexa-1,4-dien-1-yl)acetamide Chemical compound CC(=O)NC1=C(Cl)C(=O)C(NC(C)=O)=C(Cl)C1=O ZYWQUADTNKEZKA-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000004059 quinone derivatives Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
-
- A—HUMAN NECESSITIES
- A43—FOOTWEAR
- A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
- A43B3/00—Footwear characterised by the shape or the use
- A43B3/12—Sandals; Strap guides thereon
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/569—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone substituted in position 17 alpha, e.g. ethisterone
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Woven Fabrics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37618/61A GB1041279A (en) | 1961-10-19 | 1961-10-19 | 13-alkyl steroid ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122644B true NO122644B (de) | 1971-07-26 |
Family
ID=10397775
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO146143A NO122646B (de) | 1961-10-19 | 1962-10-18 | |
| NO146140A NO122643B (de) | 1961-10-19 | 1962-10-18 | |
| NO146141A NO122644B (de) | 1961-10-19 | 1962-10-18 | |
| NO146142A NO122645B (de) | 1961-10-19 | 1962-10-18 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO146143A NO122646B (de) | 1961-10-19 | 1962-10-18 | |
| NO146140A NO122643B (de) | 1961-10-19 | 1962-10-18 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO146142A NO122645B (de) | 1961-10-19 | 1962-10-18 |
Country Status (12)
| Country | Link |
|---|---|
| AT (4) | AT264730B (de) |
| CH (5) | CH450407A (de) |
| CY (1) | CY429A (de) |
| DE (4) | DE1617818B2 (de) |
| DK (6) | DK113641B (de) |
| ES (1) | ES281669A1 (de) |
| FI (4) | FI41024B (de) |
| FR (1) | FR2796M (de) |
| GB (2) | GB1041279A (de) |
| MY (1) | MY6800075A (de) |
| NO (4) | NO122646B (de) |
| SE (6) | SE312552B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2636404C2 (de) * | 1976-08-12 | 1983-12-08 | Schering AG, 1000 Berlin und 4709 Bergkamen | Δ↑1↑↑5↑-17α-Äthinylsteroide der Östranreihe, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Präparate |
| US8617597B2 (en) | 2006-07-06 | 2013-12-31 | Bayer Intellectual Property Gmbh | Pharmaceutical composition containing a tetrahydrofolic acid |
| CN104926906B (zh) * | 2015-06-04 | 2016-02-10 | 保定北瑞甾体生物有限公司 | 一种17α-羟基黄体酮的制备方法 |
-
1961
- 1961-10-19 GB GB37618/61A patent/GB1041279A/en not_active Expired
- 1961-10-19 GB GB37617/61A patent/GB1041278A/en not_active Expired
-
1962
- 1962-10-15 SE SE11024/62A patent/SE312552B/xx unknown
- 1962-10-15 SE SE11025/62A patent/SE312553B/xx unknown
- 1962-10-15 SE SE11026/62A patent/SE313809B/xx unknown
- 1962-10-15 SE SE01423/67A patent/SE335526B/xx unknown
- 1962-10-15 SE SE11023/62A patent/SE312551B/xx unknown
- 1962-10-17 CH CH1217162A patent/CH450407A/de unknown
- 1962-10-17 DK DK448162AA patent/DK113641B/da unknown
- 1962-10-17 CH CH1562666A patent/CH450408A/de unknown
- 1962-10-17 CH CH1275267A patent/CH459195A/de unknown
- 1962-10-17 CH CH1562766A patent/CH432509A/de unknown
- 1962-10-17 CH CH1562566A patent/CH455763A/de unknown
- 1962-10-18 DK DK449762AA patent/DK115621B/da unknown
- 1962-10-18 AT AT822762A patent/AT264730B/de active
- 1962-10-18 NO NO146143A patent/NO122646B/no unknown
- 1962-10-18 NO NO146140A patent/NO122643B/no unknown
- 1962-10-18 NO NO146141A patent/NO122644B/no unknown
- 1962-10-18 DE DE1962S0111837 patent/DE1617818B2/de active Granted
- 1962-10-18 DE DE19621618855 patent/DE1618855B2/de active Granted
- 1962-10-18 DK DK449662AA patent/DK115549B/da unknown
- 1962-10-18 DE DE1962S0082099 patent/DE1468604C2/de not_active Expired
- 1962-10-18 FI FI1876/62A patent/FI41024B/fi active
- 1962-10-18 NO NO146142A patent/NO122645B/no unknown
- 1962-10-18 FI FI1877/62A patent/FI41025B/fi active
- 1962-10-18 DE DE19621793608 patent/DE1793608B1/de active Pending
- 1962-10-18 DK DK449562AA patent/DK121228B/da unknown
- 1962-10-18 FI FI1879/62A patent/FI41027B/fi active
- 1962-10-18 FI FI1878/62A patent/FI41026B/fi active
- 1962-10-18 ES ES281669A patent/ES281669A1/es not_active Expired
- 1962-10-19 AT AT825662A patent/AT256354B/de active
- 1962-10-19 AT AT825862A patent/AT256356B/de active
- 1962-10-19 AT AT825762A patent/AT256355B/de active
-
1963
- 1963-01-16 FR FR921556A patent/FR2796M/fr not_active Expired
-
1966
- 1966-05-02 SE SE05984/66A patent/SE340619B/xx unknown
-
1968
- 1968-01-15 CY CY42968A patent/CY429A/xx unknown
- 1968-12-31 MY MY196875A patent/MY6800075A/xx unknown
-
1969
- 1969-04-24 DK DK227069AA patent/DK129652B/da unknown
-
1970
- 1970-06-30 DK DK339670AA patent/DK124753B/da unknown
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