DD229135A5 - Verfahren und herstellung von cyclischen 17, 21-orthoester-corticoidderivaten - Google Patents

Verfahren und herstellung von cyclischen 17, 21-orthoester-corticoidderivaten Download PDF

Info

Publication number: DD229135A5
Authority: DD; German Democratic Republic
Prior art keywords: methyl; pregnadiene; fluoro; triol; trione
Prior art date: 1983-09-07

Application number

DD84274493A

Other languages

German (de)

English (en)

Inventor

Issei Nitta

Kenichiro Nakao

Motoyoshi Miyake

Akira Maruyama

Junko Takashima

Hiroaki Ueno

Original Assignee

Mitsubishi Chem Ind

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.)

1983-09-07

Filing date

1984-09-06

Publication date

1985-10-30

1983-09-07 Priority claimed from JP58164772A external-priority patent/JPS6056997A/ja

1984-06-12 Priority claimed from JP59120439A external-priority patent/JPS611698A/ja

1984-09-06 Application filed by Mitsubishi Chem Ind filed Critical Mitsubishi Chem Ind

1985-10-30 Publication of DD229135A5 publication Critical patent/DD229135A5/de

Links

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125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000002905 orthoesters Chemical class 0.000 claims description 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
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238000000354 decomposition reaction Methods 0.000 description 7
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CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 description 5
229960004703 clobetasol propionate Drugs 0.000 description 5
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125000004043 oxo group Chemical group O=* 0.000 description 5
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
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CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 3
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
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239000011737 fluorine Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
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DVDMHNNCRXYJLU-UHFFFAOYSA-N methoxymethanetriol Chemical compound COC(O)(O)O DVDMHNNCRXYJLU-UHFFFAOYSA-N 0.000 description 2
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239000000546 pharmaceutical excipient Substances 0.000 description 2
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239000007858 starting material Substances 0.000 description 2
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241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
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239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003470 adrenal cortex hormone Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
208000002399 aphthous stomatitis Diseases 0.000 description 1
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235000019445 benzyl alcohol Nutrition 0.000 description 1
CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000740 bleeding effect Effects 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
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
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238000011097 chromatography purification Methods 0.000 description 1
206010009887 colitis Diseases 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
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239000006196 drop Substances 0.000 description 1
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210000005069 ears Anatomy 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 0.000 description 1
XJDFEHQFPQRNRJ-UHFFFAOYSA-N ethoxycarbonyl butanoate Chemical compound CCCC(=O)OC(=O)OCC XJDFEHQFPQRNRJ-UHFFFAOYSA-N 0.000 description 1
MFOMDTCBCZQHQZ-UHFFFAOYSA-N ethoxymethanetriol Chemical compound CCOC(O)(O)O MFOMDTCBCZQHQZ-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
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CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
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239000002674 ointment Substances 0.000 description 1
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239000000843 powder Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
ZLMGJSDPCYCCQB-UHFFFAOYSA-N propoxymethanetriol Chemical compound CCCOC(O)(O)O ZLMGJSDPCYCCQB-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
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239000011734 sodium Substances 0.000 description 1
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239000007921 spray Substances 0.000 description 1
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239000000829 suppository Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
- C07J5/0061—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16
- C07J5/0069—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
- C07J5/0076—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
- 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
- C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
- C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD84274493A 1983-09-07 1984-09-06 Verfahren und herstellung von cyclischen 17, 21-orthoester-corticoidderivaten DD229135A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP58164772A JPS6056997A (ja)	1983-09-07	1983-09-07	新規な６−酸素化コルチコイド／７α−カ−ボネ−ト誘導体およびその製法
JP59120439A JPS611698A (ja)	1984-06-12	1984-06-12	新規なコルチコイド誘導体およびその製法

Publications (1)

Publication Number	Publication Date
DD229135A5 true DD229135A5 (de)	1985-10-30

Family

ID=26458022

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD84274493A DD229135A5 (de)	1983-09-07	1984-09-06	Verfahren und herstellung von cyclischen 17, 21-orthoester-corticoidderivaten
DD84275355A DD229702A5 (de)	1983-09-07	1984-09-06	Verfahren zur herstellung von neuen corticoidderivaten
DD84267066A DD232497A5 (de)	1983-09-07	1984-09-06	Verfahren zur herstellung von neuen corticoidderivaten

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD84275355A DD229702A5 (de)	1983-09-07	1984-09-06	Verfahren zur herstellung von neuen corticoidderivaten
DD84267066A DD232497A5 (de)	1983-09-07	1984-09-06	Verfahren zur herstellung von neuen corticoidderivaten

Country Status (9)

Country	Link
EP (1)	EP0136586B1 (da)
AT (1)	ATE41013T1 (da)
AU (1)	AU558725B2 (da)
DD (3)	DD229135A5 (da)
DE (1)	DE3476885D1 (da)
DK (1)	DK168631B1 (da)
HU (2)	HU201092B (da)
NO (1)	NO843548L (da)
SU (2)	SU1561827A3 (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4025342A1 (de) *	1990-08-10	1992-02-13	Hoechst Ag	In 17-stellung substituierte corticoid-17-alkylcarbonate, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE69702450T2 (de)	1996-05-01	2001-03-08	The Government Of The United States Of America As Represented By The Secretary Of National Institute Of Health, Office Of Technology Transfer	21-substituierte progesteron derivate als antigestagene
US6900193B1 (en)	1996-05-01	2005-05-31	The United States Of America As Represented By The Department Of Health And Human Services	Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1518179B1 (de) *	1964-10-07	1970-01-02	Warner Lambert Pharmaceutical	Verfahren zur Herstellung von 17alpha-Acyloxy-20-keto-21-desoxy-steroiden
US3558675A (en) *	1969-06-30	1971-01-26	Merck & Co Inc	Steroid carbonates and process
GB1440063A (en) *	1972-08-11	1976-06-23	Glaxo Lab Ltd	17alpha-esters of 17alpha,21-dihydroxy-20-oxo-steroids
DE2735110A1 (de) *	1977-08-04	1979-02-15	Hoechst Ag	Corticoid-17-alkylcarbonate und verfahren zu ihrer herstellung
DE2817988A1 (de) *	1978-04-25	1979-11-08	Hoechst Ag	Corticoid 17-alkylcarbonate und verfahren zu deren herstellung
DE3133082A1 (de) *	1981-08-18	1983-03-10	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue hydrocortison-derivate, ihre herstellung und verwendung

1984
- 1984-08-23 AU AU32311/84A patent/AU558725B2/en not_active Ceased
- 1984-08-24 DK DK407384A patent/DK168631B1/da not_active IP Right Cessation
- 1984-09-04 HU HU843321A patent/HU201092B/hu not_active IP Right Cessation
- 1984-09-04 HU HU852282A patent/HUT44040A/hu unknown
- 1984-09-05 EP EP84110572A patent/EP0136586B1/en not_active Expired
- 1984-09-05 AT AT84110572T patent/ATE41013T1/de not_active IP Right Cessation
- 1984-09-05 DE DE8484110572T patent/DE3476885D1/de not_active Expired
- 1984-09-06 NO NO843548A patent/NO843548L/no unknown
- 1984-09-06 DD DD84274493A patent/DD229135A5/de not_active IP Right Cessation
- 1984-09-06 SU SU843792254A patent/SU1561827A3/ru active
- 1984-09-06 DD DD84275355A patent/DD229702A5/de not_active IP Right Cessation
- 1984-09-06 DD DD84267066A patent/DD232497A5/de not_active IP Right Cessation
1987
- 1987-11-17 SU SU874203674A patent/SU1551250A3/ru active

Also Published As

Publication number	Publication date
DD232497A5 (de)	1986-01-29
DE3476885D1 (en)	1989-04-06
HUT37944A (en)	1986-03-28
SU1561827A3 (ru)	1990-04-30
ATE41013T1 (de)	1989-03-15
AU558725B2 (en)	1987-02-05
DK407384D0 (da)	1984-08-24
DK168631B1 (da)	1994-05-09
SU1551250A3 (ru)	1990-03-15
EP0136586A2 (en)	1985-04-10
DD229702A5 (de)	1985-11-13
NO843548L (no)	1985-03-08
EP0136586A3 (en)	1986-01-29
HU201092B (en)	1990-09-28
HUT44040A (en)	1988-01-28
EP0136586B1 (en)	1989-03-01
AU3231184A (en)	1985-03-14
DK407384A (da)	1985-03-08

Legal Events

Date	Code	Title	Description
1994-12-22	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0000742B1 (de)	1982-05-12	Corticoid-17-Alkylcarbonate und Verfahren zu deren Herstellung und diese enthaltende Mittel
DE69033538T2 (de)	2001-01-04	Verfahren zur Herstellung der 1,2-Doppelbindung von 4-aza-Steroiden und kristallinen Proscor(R) und pharmazeutische Präparate davon
DE3126732C2 (de)	1987-04-30	Steroide und sie enthaltende Arzneimittel
EP0004975B1 (de)	1982-02-17	Corticoid-17-Alkylcarbonate, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel gegen Dermatosen
DE69023947T2 (de)	1996-05-30	Fluorierte Gallensäure-Derivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen daraus.
DE2655570A1 (de)	1977-06-16	Neue polyhalogensteroide und verfahren zu ihrer herstellung
DE3878463T2 (de)	1993-06-24	Verfahren zur 9-alpha-dehalogenierung von 9-alpha-steroiden.
DE3005736C2 (da)	1988-05-19
DE2743069C2 (de)	1987-03-05	21-Chlor-6&alpha;-fluor-9&alpha;-halogen-11&beta;-hydroxy-16&beta;-methyl-17&alpha;-propionyloxy-pregna-1,4-dien-3,20-dion-Verbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, welche diese Verbindungen enthalten
DE3336292C2 (da)	1992-09-10
DE2826257C3 (de)	1980-12-04	Hydrocortison-17,21-diester und Verfahren zu deren Herstellung, diese enthaltende Arzneimittel sowie Hydrocortison -17-propionat als Zwischenprodukt
DE2954699C2 (da)	1992-04-16
CH634085A5 (de)	1983-01-14	Verfahren zur herstellung neuer kortikoide.
DD232497A5 (de)	1986-01-29	Verfahren zur herstellung von neuen corticoidderivaten
EP0077541B1 (de)	1985-06-05	Delta-1,3,5-3-Chlor-11-Beta,16-Alpha,17-Alpha,21-tetra-(hydroxy)-pregnan-20-on-16,17-acetonidderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DD232280A5 (de)	1986-01-22	Verfahren zur herstellung von neuen corticoidderivaten
DE1938218A1 (de)	1971-02-04	Neue 21,21-Dichlorsteroide
DE2365992A1 (de)	1977-05-18	6 alpha-fluor-17,21-dihydroxy-16 beta-methylpregna-4,9(11)-dien-3,20- dion-17,21-diacetat und verfahren zu dessen herstellung
DE1568077A1 (de)	1970-03-12	Verfahren zur Herstellung von Steroidestern,neue Steroidester und deren Verwendung
DE2920092A1 (de)	1979-11-29	Antivitamin d-verbindungen und diese enthaltende pharmazeutische zusammensetzungen
CH643864A5 (de)	1984-06-29	16,17-pyrazolino- und 16,17-isopyrazolino-1, 4-pregnadien-derivate.
DE69826356T2 (de)	2006-02-16	Sulfatierung von Östrogen-Mischungen
DE2812741A1 (de)	1978-10-05	Vitamin d tief 3 -derivate, verfahren zu deren herstellung und diese enthaltende arzneimittel
AT395428B (de)	1992-12-28	Verfahren zur herstellung von neuen androstancarbothioaten
DE2409971A1 (de)	1974-09-05	5-cholestenderivate und verfahren zu ihrer herstellung