NO127193B - - Google Patents
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- Publication number
- NO127193B NO127193B NO16575366A NO16575366A NO127193B NO 127193 B NO127193 B NO 127193B NO 16575366 A NO16575366 A NO 16575366A NO 16575366 A NO16575366 A NO 16575366A NO 127193 B NO127193 B NO 127193B
- Authority
- NO
- Norway
- Prior art keywords
- group
- carbon atoms
- chloroethynyl
- hydrogen
- ring
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- -1 steroid ketone Chemical class 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 150000003431 steroids Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 238000002425 crystallisation Methods 0.000 claims 2
- 230000008025 crystallization Effects 0.000 claims 2
- DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- KZQSXALQTHVPDQ-UHFFFAOYSA-M sodium;butanedioate;hydron Chemical compound [Na+].OC(=O)CCC([O-])=O KZQSXALQTHVPDQ-UHFFFAOYSA-M 0.000 claims 1
- 239000000047 product Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 230000000875 corresponding effect Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 210000001672 ovary Anatomy 0.000 description 3
- 230000001817 pituitary effect Effects 0.000 description 3
- 230000001072 progestational effect Effects 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000003637 steroidlike Effects 0.000 description 3
- 208000012868 Overgrowth Diseases 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000001456 gonadotroph Effects 0.000 description 2
- 125000000232 haloalkynyl group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000837 carbohydrate group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001447 compensatory effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011905 homologation Methods 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61K31/567—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
-
- 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
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK448162AA DK113641B (da) | 1961-10-19 | 1962-10-17 | Fremgangsmåde til fremstilling af steroidketoner. |
| GB3206463A GB1100441A (en) | 1963-08-14 | 1963-08-14 | 13-alkyl 17-halogenoalkynyl-steroid 3-ketones and their derivatives |
| DK400464A DK134161B (da) | 1962-10-17 | 1964-08-13 | Analogifremgangsmåde til fremstilling af steroidketoner. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127193B true NO127193B (de) | 1973-05-21 |
Family
ID=27221920
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15427664A NO126016B (de) | 1962-10-17 | 1964-08-05 | |
| NO16575366A NO127193B (de) | 1962-10-17 | 1966-11-25 | |
| NO495971A NO129905B (de) | 1962-10-17 | 1971-12-30 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO15427664A NO126016B (de) | 1962-10-17 | 1964-08-05 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO495971A NO129905B (de) | 1962-10-17 | 1971-12-30 |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4837029B1 (de) |
| AT (3) | AT269376B (de) |
| BE (1) | BE651797A (de) |
| BR (1) | BR6461643D0 (de) |
| CH (1) | CH498819A (de) |
| DE (4) | DE1618871C3 (de) |
| DK (3) | DK134161B (de) |
| FR (2) | FR1566154A (de) |
| GB (2) | GB1100444A (de) |
| IL (1) | IL21826A (de) |
| IN (2) | IN95058B (de) |
| NL (2) | NL139307B (de) |
| NO (3) | NO126016B (de) |
| SE (5) | SE331470B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2913381A1 (de) * | 1979-03-30 | 1980-10-16 | Schering Ag | 11-methylensteroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| JPS57106714U (de) * | 1980-12-23 | 1982-07-01 | ||
| DE3214689A1 (de) * | 1982-04-16 | 1983-10-27 | Schering AG, 1000 Berlin und 4709 Bergkamen | 11ss-chlor-steroide, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| EP2675820A1 (de) * | 2011-02-17 | 2013-12-25 | Lupin Limited | Verbessertes verfahren zur herstellung von levonorgestrel |
-
0
- BE BE651797D patent/BE651797A/xx unknown
-
1963
- 1963-08-14 GB GB4001767A patent/GB1100444A/en not_active Expired
- 1963-08-14 GB GB4001667A patent/GB1100443A/en not_active Expired
-
1964
- 1964-08-03 IL IL2182664A patent/IL21826A/en unknown
- 1964-08-05 NO NO15427664A patent/NO126016B/no unknown
- 1964-08-05 IN IN95058A patent/IN95058B/en unknown
- 1964-08-10 DE DE19641618871 patent/DE1618871C3/de not_active Expired
- 1964-08-10 DE DE19641618872 patent/DE1618872C3/de not_active Expired
- 1964-08-10 DE DE19641468988 patent/DE1468988B1/de active Pending
- 1964-08-10 DE DE19641793641 patent/DE1793641C2/de not_active Expired
- 1964-08-10 BR BR16164364A patent/BR6461643D0/pt unknown
- 1964-08-12 CH CH1052964A patent/CH498819A/de not_active IP Right Cessation
- 1964-08-13 FR FR1566154D patent/FR1566154A/fr not_active Expired
- 1964-08-13 AT AT696964A patent/AT269376B/de active
- 1964-08-13 DK DK400464A patent/DK134161B/da unknown
- 1964-08-13 AT AT227470A patent/AT301045B/de not_active IP Right Cessation
- 1964-08-13 AT AT292768A patent/AT301039B/de not_active IP Right Cessation
- 1964-08-14 NL NL6409391A patent/NL139307B/xx unknown
- 1964-08-14 SE SE983464A patent/SE331470B/xx unknown
- 1964-08-14 SE SE843170A patent/SE350256B/xx unknown
- 1964-11-12 FR FR994684A patent/FR4915M/fr not_active Expired
-
1966
- 1966-11-25 NO NO16575366A patent/NO127193B/no unknown
-
1968
- 1968-03-29 SE SE04237/68A patent/SE335119B/xx unknown
- 1968-03-29 SE SE04239/68A patent/SE334879B/xx unknown
- 1968-03-29 SE SE04238/68A patent/SE335120B/xx unknown
-
1969
- 1969-12-10 DK DK655269A patent/DK127598B/da unknown
-
1971
- 1971-08-02 JP JP5758471A patent/JPS4837029B1/ja active Pending
- 1971-12-30 NO NO495971A patent/NO129905B/no unknown
-
1972
- 1972-05-03 DK DK220272A patent/DK127475B/da unknown
-
1973
- 1973-06-19 NL NL7308508A patent/NL7308508A/xx unknown
-
1974
- 1974-05-03 IN IN137555A patent/IN137555B/en unknown
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