DD156975A5 - Verfahren zur herstellung neuer mehrfach ungesaettigter bnc-halogenide - Google Patents

Verfahren zur herstellung neuer mehrfach ungesaettigter bnc-halogenide Download PDF

Info

Publication number: DD156975A5
Authority: DD; German Democratic Republic
Prior art keywords: bnc; chloride; pregna; halides; reaction
Prior art date: 1980-01-15

Application number

DD81226986A

Other languages

German (de)

English (en)

Inventor

Leroy O Krbechek

Wolfgang Preuss

Original Assignee

Henkel Kg

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.)

1980-01-15

Filing date

1981-01-14

Publication date

1982-10-06

1980-01-15 Priority claimed from DE19803001222 external-priority patent/DE3001222A1/de

1980-02-04 Priority claimed from AT0058280A external-priority patent/ATA58280A/de

1980-02-19 Priority claimed from US06/122,397 external-priority patent/US4255345A/en

1981-01-14 Application filed by Henkel Kg filed Critical Henkel Kg

1982-10-06 Publication of DD156975A5 publication Critical patent/DD156975A5/de

Links

238000004519 manufacturing process Methods 0.000 title abstract description 4
-1 BNC halides Chemical class 0.000 claims abstract description 24
150000001875 compounds Chemical class 0.000 claims abstract description 10
238000006243 chemical reaction Methods 0.000 claims description 31
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
238000000034 method Methods 0.000 claims description 15
238000002360 preparation method Methods 0.000 claims description 8
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 5
YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 claims description 4
BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 claims description 4
PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 4
229940031439 squalene Drugs 0.000 claims description 4
TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
230000035484 reaction time Effects 0.000 claims description 3
150000008282 halocarbons Chemical class 0.000 claims description 2
235000021388 linseed oil Nutrition 0.000 claims description 2
239000000944 linseed oil Substances 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 7
QETBTXOVEBTJQH-WAMTXRNCSA-N 3-oxo-23,24-bisnorchol-4-en-22-oic acid Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)C(O)=O)[C@@]1(C)CC2 QETBTXOVEBTJQH-WAMTXRNCSA-N 0.000 abstract description 3
108700041286 delta Proteins 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000000460 chlorine Substances 0.000 description 10
230000002140 halogenating effect Effects 0.000 description 10
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 6
150000004820 halides Chemical class 0.000 description 5
150000003431 steroids Chemical group 0.000 description 5
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
NRESKKGDHRQEMH-HPGXARPTSA-N 2-[(8r,9s,10s,13s,14s,17r)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]propanoic acid Chemical class C1CC2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(C)C(O)=O)[C@@]1(C)CC2 NRESKKGDHRQEMH-HPGXARPTSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 2
JFGNAYZCSHYUJF-FCMAGTKHSA-N (8s,9s,10r,13s,14s)-17-ethylidene-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(=CC)[C@@]1(C)CC2 JFGNAYZCSHYUJF-FCMAGTKHSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
FTWGUJZXVWYZGD-WFLKQGPQSA-N 2-[(8r,9s,10r,13s,14s)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-17-ylidene]propanoic acid Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(=C(C(O)=O)C)[C@@]1(C)CC2 FTWGUJZXVWYZGD-WFLKQGPQSA-N 0.000 description 1
JJVWWLILUCSYPJ-WFLKQGPQSA-N 2-[(8s,9s,10r,13s,14s)-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-ylidene]propanoic acid Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(=C(C(O)=O)C)[C@@]1(C)CC2 JJVWWLILUCSYPJ-WFLKQGPQSA-N 0.000 description 1
SAPOLFJAFIPJGT-WFLKQGPQSA-N 2-[(8s,9s,10r,13s,14s)-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-ylidene]propanoyl chloride Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(=C(C(Cl)=O)C)[C@@]1(C)CC2 SAPOLFJAFIPJGT-WFLKQGPQSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
LIMQQADUEULBSO-UHFFFAOYSA-N butyl isothiocyanate Chemical group CCCCN=C=S LIMQQADUEULBSO-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000011031 large-scale manufacturing process Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
238000013048 microbiological method Methods 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000005245 sintering Methods 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000010409 thin film Substances 0.000 description 1
LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)

DD81226986A 1980-01-15 1981-01-14 Verfahren zur herstellung neuer mehrfach ungesaettigter bnc-halogenide DD156975A5 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19803001222 DE3001222A1 (de)	1980-01-15	1980-01-15	Pregna-1,4-dien-3-on-20-carbonylchlorid und verfahren zu seiner herstellung
AT0058280A ATA58280A (de)	1980-02-04	1980-02-04	Verfahren zur herstellung von neuem 20-carboxypregna-1,4,17(20)-trien-3-on (delta 1,4,17-bnc)
US06/122,397 US4255345A (en)	1980-02-19	1980-02-19	Steroid production

Publications (1)

Publication Number	Publication Date
DD156975A5 true DD156975A5 (de)	1982-10-06

Family

ID=27146483

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81226986A DD156975A5 (de)	1980-01-15	1981-01-14	Verfahren zur herstellung neuer mehrfach ungesaettigter bnc-halogenide

Country Status (4)

Country	Link
EP (1)	EP0034248B1 (da)
DD (1)	DD156975A5 (da)
DE (1)	DE3164924D1 (da)
DK (1)	DK17081A (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE478913T1 (de)	2000-06-02	2010-09-15	Stanford Res Inst Int	Polymermembranzusammensetzung
US7316855B2 (en)	2001-06-01	2008-01-08	Polyfuel, Inc.	Fuel cell assembly for portable electronic device and interface, control, and regulator circuit for fuel cell powered electronic device
WO2002099916A2 (en)	2001-06-01	2002-12-12	Polyfuel, Inc	Fuel cell assembly for portable electronic device and interface, control, and regulator circuit for fuel cell powered electronic device
CA2485971A1 (en)	2002-05-13	2004-05-21	Polyfuel, Inc.	Ion conductive block copolymers

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3994933A (en) *	1975-04-30	1976-11-30	G. D. Searle & Co.	3-Oxo-pregna-4,17(20)-dien-20-carboxylic acid and esters
AT362086B (de) *	1978-04-17	1981-04-27	Henkel Kgaa	Verfahren zur herstellung von 17-c-steroid- -alpha-propionsaeureverbindungen durch mikro- biellen seitenkettenabbau an 17-c-seitenketten- -steroidsubstraten

1981
- 1981-01-10 DE DE8181100145T patent/DE3164924D1/de not_active Expired
- 1981-01-10 EP EP81100145A patent/EP0034248B1/de not_active Expired
- 1981-01-14 DD DD81226986A patent/DD156975A5/de unknown
- 1981-01-15 DK DK17081A patent/DK17081A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP0034248A1 (de)	1981-08-26
DE3164924D1 (en)	1984-08-30
EP0034248B1 (de)	1984-07-25
DK17081A (da)	1981-07-16

Publication	Publication Date	Title
EP0291860A1 (de)	1988-11-23	Verfahren zur Herstellung von CF3I
DD156975A5 (de)	1982-10-06	Verfahren zur herstellung neuer mehrfach ungesaettigter bnc-halogenide
AT363202B (de)	1981-07-27	Verfahren zur herstellung von neuen mehrfach halogenierten steroiden
EP0034364B1 (de)	1984-11-07	Neue 20-substituierte 3-Oxo-pregna-4-en-steroidverbindungen und Verfahren zu ihrer Herstellung
DE2748442B2 (da)	1980-09-18
DE2149798A1 (de)	1972-08-03	Steroide der Pregnanreihe und Verfahren zu ihrer Herstellung
DE2246203C3 (de)	1982-01-21	Verfahren zur Herstellung von Steroid-21-alkoholen
DE2754759C2 (de)	1987-03-26	3&alpha;-Hydroxy-5&beta;-cholest-24-en
EP0005523B1 (de)	1981-08-26	D-Homosteroide, Verfahren zu deren Herstellung
AT374205B (de)	1984-03-26	Verfahren zur herstellung eines neuen delta 1,4,17-bisnovcholansaeure-derivates
DE955949C (de)	1957-01-10	Verfahren zur Herstellung von in ª‡-Stellung zur Ketogruppe chlorierten Ketosteroiden
DE2225324C3 (de)	1977-10-27	Verfahren zur Herstellung von 6 a, 21-Difluor-20oxopregnansteroiden
DD204096A5 (de)	1983-11-16	Neue 3-chlorpregnan-derivate und verfahren zu ihrer herstellung
DE2148631B2 (de)	1973-03-22	Verfahren zur herstellung von in der 9(11)- und/oder 16-stellung ungesaettigten steroiden
EP0039895B1 (de)	1984-07-18	Neue Pregnan-20-Carbonsäurederivate und Verfahren zu ihrer Herstellung
EP0034368B1 (de)	1984-06-20	Verfahren zur Umwandlung von Steroid-20-Carbonsäureamiden in die entsprechenden Steroid-20-Carbamate
DE2365102C2 (de)	1982-12-02	Neue Pregnansäure-Derivate
DE3001222A1 (de)	1981-07-23	Pregna-1,4-dien-3-on-20-carbonylchlorid und verfahren zu seiner herstellung
AT229497B (de)	1963-09-25	Verfahren zur Herstellung von 9-Halogen-1, 4-pregnadien-11-olen
AT364098B (de)	1981-09-25	Verfahren zur herstellung von neuen estern von androstadien-17-carbonsaeuren
AT362888B (de)	1981-06-25	Verfahren zur herstellung von neuen estern von androstadien-17-carbonsaeuren
EP0039861A1 (de)	1981-11-18	Verfahren zum Abbau der 20-Carboxylgruppe in delta-1,4-BNC und verwandten Steroidverbindungen sowie neue stickstoffhaltige C-21-Steroidverbindungen
DE961534C (de)	1957-04-11	Verfahren zur Herstellung von in 4-Stellung halogenierten 3-Ketosteroiden
AT232657B (de)	1964-03-25	Verfahren zur Herstellung von Enolacylaten von 16α-Alkyl-20-ketosteroiden
DE3431009A1 (de)	1985-03-21	Verfahren zur herstellung von 6-demethyl-6-desoxy-6-methylen-5-oxytetracyclin und dessen 11a-chlorderivat