CH518918A - Verfahren zur Herstellung von Gona-4,9-dien-3-onen - Google Patents

Verfahren zur Herstellung von Gona-4,9-dien-3-onen

Info

Publication number: CH518918A
Authority: CH; Switzerland
Prior art keywords: group; formula; compound; hydroxyl; bromine
Prior art date: 1963-08-14

Application number

CH1053064A

Other languages

German (de)

English (en)

Inventor

David Dr Hartley

Alan Dr Hughes Gordon

Herchel Dr Smith

Original Assignee

Smith Herchel

Priority date (The priority date 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 date listed.)

1963-08-14

Filing date

1964-08-12

Publication date

1972-02-15

1964-08-12 Application filed by Smith Herchel filed Critical Smith Herchel

1972-02-15 Publication of CH518918A publication Critical patent/CH518918A/de

Links

230000002401 inhibitory effect Effects 0.000 title abstract description 4
239000000583 progesterone congener Substances 0.000 title description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000005977 Ethylene Chemical group 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
239000011541 reaction mixture Substances 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
229910052801 chlorine Inorganic materials 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
238000004064 recycling Methods 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 10
239000000203 mixture Substances 0.000 abstract description 6
125000000217 alkyl group Chemical group 0.000 abstract description 5
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 3
230000001817 pituitary effect Effects 0.000 abstract description 3
125000002252 acyl group Chemical group 0.000 abstract 1
230000001833 anti-estrogenic effect Effects 0.000 abstract 1
229910052681 coesite Inorganic materials 0.000 abstract 1
229910052906 cristobalite Inorganic materials 0.000 abstract 1
230000003152 gestagenic effect Effects 0.000 abstract 1
229940088597 hormone Drugs 0.000 abstract 1
239000005556 hormone Substances 0.000 abstract 1
239000000377 silicon dioxide Substances 0.000 abstract 1
235000012239 silicon dioxide Nutrition 0.000 abstract 1
229910052682 stishovite Inorganic materials 0.000 abstract 1
229910052905 tridymite Inorganic materials 0.000 abstract 1
238000007269 dehydrobromination reaction Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
230000031709 bromination Effects 0.000 description 5
238000005893 bromination reaction Methods 0.000 description 5
-1 bromine compound Chemical class 0.000 description 5
230000001072 progestational effect Effects 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
206010020880 Hypertrophy Diseases 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229940011871 estrogen Drugs 0.000 description 2
239000000262 estrogen Substances 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
125000000232 haloalkynyl group Chemical group 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
210000001672 ovary Anatomy 0.000 description 2
239000000186 progesterone Substances 0.000 description 2
229960003387 progesterone Drugs 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000028327 secretion Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007858 starting material Substances 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
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-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
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
102000006771 Gonadotropins Human genes 0.000 description 1
108010086677 Gonadotropins Proteins 0.000 description 1
241000700159 Rattus Species 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000006243 chemical reaction Methods 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
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000001456 gonadotroph Effects 0.000 description 1
239000002622 gonadotropin Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000011905 homologation Methods 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 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
229910052757 nitrogen Inorganic materials 0.000 description 1
230000002611 ovarian Effects 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000011120 smear test Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003270 steroid hormone Substances 0.000 description 1
150000003431 steroids Chemical group 0.000 description 1
125000001424 substituent group Chemical group 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
210000001215 vagina Anatomy 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)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CH1053064A 1963-08-14 1964-08-12 Verfahren zur Herstellung von Gona-4,9-dien-3-onen CH518918A (de)

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
CH518918A true CH518918A (de)	1972-02-15

Family

ID=10332644

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1053064A CH518918A (de)	1963-08-14	1964-08-12	Verfahren zur Herstellung von Gona-4,9-dien-3-onen
CH663971A CH540895A (de)	1963-08-14	1964-08-12	Verfahren zur Herstellung von Gonadienonen

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH663971A CH540895A (de)	1963-08-14	1964-08-12	Verfahren zur Herstellung von Gonadienonen

Country Status (12)

Country	Link
AT (2)	AT267078B (fr)
BE (1)	BE651798A (fr)
BR (1)	BR6461644D0 (fr)
CH (2)	CH518918A (fr)
DE (1)	DE1468989C2 (fr)
DK (1)	DK131114B (fr)
ES (1)	ES303114A1 (fr)
FR (2)	FR1447954A (fr)
GB (1)	GB1100442A (fr)
NL (1)	NL6409385A (fr)
NO (2)	NO125630B (fr)
SE (2)	SE330381B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2012095644A1 (fr)	2011-01-12	2012-07-19	Siemens Aktiengesellschaft	Source de neutrons compacte à faible énergie

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 DE DE1468989A patent/DE1468989C2/de not_active Expired
- 1964-08-10 BR BR161644/64A patent/BR6461644D0/pt unknown
- 1964-08-12 CH CH1053064A patent/CH518918A/de not_active IP Right Cessation
- 1964-08-12 CH CH663971A patent/CH540895A/de not_active IP Right Cessation
- 1964-08-13 AT AT697064A patent/AT267078B/de active
- 1964-08-13 ES ES0303114A patent/ES303114A1/es not_active Expired
- 1964-08-13 FR FR985157A patent/FR1447954A/fr not_active Expired
- 1964-08-13 DK DK400564AA patent/DK131114B/da unknown
- 1964-08-13 AT AT762366A patent/AT292207B/de not_active IP Right Cessation
- 1964-08-14 SE SE09835/64A patent/SE330381B/xx unknown
- 1964-08-14 SE SE03944/68A patent/SE328872B/xx unknown
- 1964-08-14 NL NL6409385A patent/NL6409385A/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
SE330381B (fr)	1970-11-16
FR4877M (fr)	1967-03-06
DE1468989C2 (de)	1974-05-30
FR1447954A (fr)	1966-08-05
NO125630B (fr)	1972-10-09
DK131114B (da)	1975-05-26
AT267078B (de)	1968-12-10
GB1100442A (en)	1968-01-24
NL6409385A (fr)	1965-08-25
AT292207B (de)	1971-08-25
NO126366B (fr)	1973-01-29
BE651798A (fr)
DK131114C (fr)	1975-10-27
CH540895A (de)	1973-10-15
ES303114A1 (es)	1965-02-01
SE328872B (fr)	1970-09-28
DE1468989B1 (de)	1973-10-25
BR6461644D0 (pt)	1973-08-07

Legal Events

Date	Code	Title	Description
1983-07-29	PL	Patent ceased

Publication	Publication Date	Title
DE2301317C2 (de)	1983-11-03	Alkylierte 3,20-Diketo-&Delta;&uarr;4&uarr;-steroide der Pregnanreihe und Verfahren zu deren Herstellung
CH518918A (de)	1972-02-15	Verfahren zur Herstellung von Gona-4,9-dien-3-onen
DE1468410A1 (de)	1969-11-20	Verfahren zur Herstellung von 16-Methylensteroiden
DE1793633C3 (de)	1973-10-04	Verfahren zur Herstellung von Gona 4(5),9(10)dien3 onen Ausscheidung aus 1468642
DE1793641C2 (de)	1973-12-20	Verfahren zur Herstellung von 17-Halogenalkinyl 3-ketogonen und deren Verwendung. Ausscheidung aus: 1468988
CH550156A (de)	1974-06-14	Verfahren zur herstellung von 3,6-dihydroxy-(delta)5(10)-steroiden.
DE1468988C (de)	1972-07-06	nalpha-Chloräthinyl-lSbeta-äthyl-4-oder-5( 10)- gonen-3 -ketone.'
AT228410B (de)	1963-07-10	Verfahren zur Herstellung neuer 6-Methyl-3-oxo-4, 6-dien-steroide
DE1468642C (de)	1971-10-28	Gona-4(5), 9(10>dien-3-one
DE2030056C (de)	1973-03-22	Verfahren zur Äthinylierung von 17-Ketosteroiden
DE882548C (de)	1953-07-09	Verfahren zur Herstellung von ?-Estern von Steroidsapogeninen mit einer 3-Oxygruppe und einer Spiroketalseitenkette in 16, 17-Stellung
AT160824B (de)	1942-05-20	Verfahren zur Darstellung ungesättigter Oxyketone der Cyclopentanopolyhydrophenanthrenreihe.
AT265542B (de)	1968-10-10	Verfahren zur Herstellung neuer 9β,10α-Steroide
AT235479B (de)	1964-08-25	Verfahren zur Herstellung von neuen 17α-Halogenäthinylsteroiden der Androstan- oder der 19-nor-Androstanreihe
DE1543282C3 (de)	1976-01-22	9beta, lOalpha-Steroide, Verfahren zur Herstellung dieser Verbindungen und pharmazeutische Präparate, welche diese Verbindungen als Wirkstoffe enthalten
DE2110140B2 (fr)	1979-06-21
DE1114487B (de)	1961-10-05	Verfahren zur Herstellung von 6a, 6a-Dichlor-6,7-methylen- und 6a, 6a-Dibrom-6,7-methylenverbindungen von í¸-3-Ketosteroiden der Androstan- und Pregnanreihe
CH376909A (de)	1964-04-30	Verfahren zur Herstellung von 6a,6a-Dichlor-6,7-methylen- und 6a,6a-Dibrom-6,7-methylenverbindungen von 4-3-Ketosteroiden
DE1044077B (de)	1958-11-20	Verfahren zur Herstellung von 1,4,6-Trien-3-ketosteroiden
DE1040546B (de)	1958-10-09	Verfahren zur Herstellung von ungesaettigten, gegebenenfalls Brom enthaltenden Steroidverbindungen der Androstan- und Pregnanreihe
CH498820A (de)	1970-11-15	Verfahren zur Herstellung von Steroidketonderivaten mit 17- oder 17a-Halogenalkinylgruppen
DE1081888B (de)	1960-05-19	Verfahren zur Herstellung von ?-3-Keto-9 ª‡-halogensteroiden
DE1176131B (de)	1964-08-20	Verfahren zur Herstellung von 16-Cyan- und 16-Cyan-16, 17-seco-steroiden
DE1117572B (de)	1961-11-23	Verfahren zur Herstellung von Alkylaethern sekundaerer Steroidalkohole der Androstan-, Oestran- und Pregnanreihe
DE1543468A1 (de)	1969-09-18	Verfahren zur Herstellung neuer Cyclopentanophenanthrenderivate