NO125630B - - Google Patents
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- Publication number
- NO125630B NO125630B NO154277A NO15427764A NO125630B NO 125630 B NO125630 B NO 125630B NO 154277 A NO154277 A NO 154277A NO 15427764 A NO15427764 A NO 15427764A NO 125630 B NO125630 B NO 125630B
- Authority
- NO
- Norway
- Prior art keywords
- group
- compound
- dehydrobromination
- carbon atoms
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- 238000007269 dehydrobromination reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 230000031709 bromination Effects 0.000 claims description 8
- 238000005893 bromination reaction Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 239000005977 Ethylene Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- -1 chloroethynyl- Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000001072 progestational effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000001672 ovary Anatomy 0.000 description 3
- 230000001817 pituitary effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 208000012868 Overgrowth Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000001456 gonadotroph Effects 0.000 description 2
- 125000000232 haloalkynyl group Chemical group 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
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- 206010020880 Hypertrophy Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001447 compensatory effect Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- 238000011121 vaginal smear 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
-
- 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
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32065/63A GB1100442A (en) | 1963-08-14 | 1963-08-14 | Gonadienones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125630B true NO125630B (de) | 1972-10-09 |
Family
ID=10332644
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO154277A NO125630B (de) | 1963-08-14 | 1964-08-05 | |
| NO00165751A NO126366B (de) | 1963-08-14 | 1966-11-25 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00165751A NO126366B (de) | 1963-08-14 | 1966-11-25 |
Country Status (12)
| Country | Link |
|---|---|
| AT (2) | AT292207B (de) |
| BE (1) | BE651798A (de) |
| BR (1) | BR6461644D0 (de) |
| CH (2) | CH540895A (de) |
| DE (1) | DE1468989C2 (de) |
| DK (1) | DK131114B (de) |
| ES (1) | ES303114A1 (de) |
| FR (2) | FR1447954A (de) |
| GB (1) | GB1100442A (de) |
| NL (1) | NL6409385A (de) |
| NO (2) | NO125630B (de) |
| SE (2) | SE328872B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012095644A1 (en) | 2011-01-12 | 2012-07-19 | Siemens Aktiengesellschaft | A compact, low energy neutron source |
-
0
- BE BE651798D patent/BE651798A/xx unknown
-
1963
- 1963-08-14 GB GB32065/63A patent/GB1100442A/en not_active Expired
-
1964
- 1964-08-05 NO NO154277A patent/NO125630B/no unknown
- 1964-08-10 BR BR161644/64A patent/BR6461644D0/pt unknown
- 1964-08-10 DE DE1468989A patent/DE1468989C2/de not_active Expired
- 1964-08-12 CH CH663971A patent/CH540895A/de not_active IP Right Cessation
- 1964-08-12 CH CH1053064A patent/CH518918A/de not_active IP Right Cessation
- 1964-08-13 DK DK400564AA patent/DK131114B/da unknown
- 1964-08-13 ES ES0303114A patent/ES303114A1/es not_active Expired
- 1964-08-13 AT AT762366A patent/AT292207B/de not_active IP Right Cessation
- 1964-08-13 FR FR985157A patent/FR1447954A/fr not_active Expired
- 1964-08-13 AT AT697064A patent/AT267078B/de active
- 1964-08-14 SE SE03944/68A patent/SE328872B/xx unknown
- 1964-08-14 NL NL6409385A patent/NL6409385A/xx unknown
- 1964-08-14 SE SE09835/64A patent/SE330381B/xx unknown
- 1964-11-12 FR FR994685A patent/FR4877M/fr not_active Expired
-
1966
- 1966-11-25 NO NO00165751A patent/NO126366B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR4877M (de) | 1967-03-06 |
| SE330381B (de) | 1970-11-16 |
| NO126366B (de) | 1973-01-29 |
| AT292207B (de) | 1971-08-25 |
| SE328872B (de) | 1970-09-28 |
| GB1100442A (en) | 1968-01-24 |
| FR1447954A (fr) | 1966-08-05 |
| BR6461644D0 (pt) | 1973-08-07 |
| AT267078B (de) | 1968-12-10 |
| NL6409385A (de) | 1965-08-25 |
| CH518918A (de) | 1972-02-15 |
| DK131114C (de) | 1975-10-27 |
| CH540895A (de) | 1973-10-15 |
| ES303114A1 (es) | 1965-02-01 |
| BE651798A (de) | |
| DE1468989C2 (de) | 1974-05-30 |
| DE1468989B1 (de) | 1973-10-25 |
| DK131114B (da) | 1975-05-26 |
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