NO743449L - - Google Patents

Info

Publication number: NO743449L
Authority: NO; Norway
Prior art keywords: homo; dione; methylene; pregnene; hydroxy
Prior art date: 1973-09-26

Application number

NO743449A

Other languages

English (en)

Norwegian (no)

Inventor

U Kerb

R Wiechert

L Alig

A Fuerst

M Mueller

P Keller

Original Assignee

Schering Ag

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.)

1973-09-26

Filing date

1974-09-25

Publication date

1975-04-28

1974-09-25 Application filed by Schering Ag filed Critical Schering Ag

1975-04-28 Publication of NO743449L publication Critical patent/NO743449L/no

Links

238000000034 method Methods 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
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 claims 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
RJKFOVLPORLFTN-UHFFFAOYSA-N progesterone acetate Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C(=O)C)C1(C)CC2 RJKFOVLPORLFTN-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
239000005457 ice water Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
-1 alkali metal alcohols Chemical class 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229960005215 dichloroacetic acid Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
230000007306 turnover Effects 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids

Landscapes

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)
Epoxy Compounds (AREA)

NO743449A 1973-09-26 1974-09-25 NO743449L (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732349024 DE2349024A1 (de)	1973-09-26	1973-09-26	6beta,7beta-epoxy-1alpha,2alphamethylen-d-homo-4-pregnen-3,20-dione

Publications (1)

Publication Number	Publication Date
NO743449L true NO743449L (fr)	1975-04-28

Family

ID=5894080

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO743449A NO743449L (fr)	1973-09-26	1974-09-25

Country Status (16)

Country	Link
US (1)	US3965128A (fr)
JP (1)	JPS5059362A (fr)
AR (1)	AR202946A1 (fr)
AU (1)	AU7374074A (fr)
BE (1)	BE820381A (fr)
DD (1)	DD114599A5 (fr)
DE (1)	DE2349024A1 (fr)
DK (1)	DK507974A (fr)
FI (1)	FI280574A7 (fr)
FR (1)	FR2244492A1 (fr)
IL (1)	IL45629A0 (fr)
LU (1)	LU70985A1 (fr)
NL (1)	NL7412747A (fr)
NO (1)	NO743449L (fr)
SE (1)	SE7412058L (fr)
ZA (1)	ZA746131B (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1999025703A1 (fr) *	1997-11-14	1999-05-27	Merck & Co., Inc.	Triterpenes tetracycliques immunodepresseurs
US6022890A (en) *	1997-11-14	2000-02-08	Merck & Co., Inc.	Immunosuppressant tetracyclic triterpenes
US7846915B2 (en) *	2004-10-20	2010-12-07	Resverlogix Corporation	Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases
WO2007016525A2 (fr) *	2005-07-29	2007-02-08	Resverlogix Corp.	Compositions pharmaceutiques pour la prevention et le traitement de maladies complexes et leur administration par des dispositifs medicaux inserables
PT2118074E (pt)	2007-02-01	2014-03-20	Resverlogix Corp	Compostos para a prevenção e tratamento de doenças cardiovasculares
US8114995B2 (en)	2008-06-26	2012-02-14	Resverlogix Corp.	Methods of preparing quinazolinone derivatives
ES2542835T3 (es)	2009-01-08	2015-08-12	Resverlogix Corporation	Compuestos para la prevención y el tratamiento de enfermedades cardiovasculares
NZ617779A (en)	2009-03-18	2015-08-28	Resverlogix Corp	Novel anti-inflammatory agents
US9757368B2 (en)	2009-04-22	2017-09-12	Resverlogix Corp.	Anti-inflammatory agents
PT2773354T (pt)	2011-11-01	2019-07-17	Resverlogix Corp	Formulações orais de libertação imediata para quinazolinonas substituídas
US9765039B2 (en)	2012-11-21	2017-09-19	Zenith Epigenetics Ltd.	Biaryl derivatives as bromodomain inhibitors
US9073878B2 (en)	2012-11-21	2015-07-07	Zenith Epigenetics Corp.	Cyclic amines as bromodomain inhibitors
JP2016507496A (ja)	2012-12-21	2016-03-10	ゼニス・エピジェネティクス・コーポレイションＺｅｎｉｔｈＥｐｉｇｅｎｅｔｉｃｓＣｏｒｐ．	ブロモドメイン阻害剤としての新規複素環式化合物
CN114984016A (zh)	2015-03-13	2022-09-02	雷斯韦洛吉克斯公司	用于治疗补体相关疾病之组合物及治疗方法

1973
- 1973-09-26 DE DE19732349024 patent/DE2349024A1/de active Pending
1974
- 1974-09-10 IL IL45629A patent/IL45629A0/xx unknown
- 1974-09-23 US US05/508,492 patent/US3965128A/en not_active Expired - Lifetime
- 1974-09-24 DD DD181291A patent/DD114599A5/xx unknown
- 1974-09-24 LU LU70985A patent/LU70985A1/xx unknown
- 1974-09-25 NO NO743449A patent/NO743449L/no unknown
- 1974-09-25 JP JP49110412A patent/JPS5059362A/ja active Pending
- 1974-09-25 SE SE7412058A patent/SE7412058L/ not_active Application Discontinuation
- 1974-09-26 BE BE148933A patent/BE820381A/fr unknown
- 1974-09-26 NL NL7412747A patent/NL7412747A/xx unknown
- 1974-09-26 DK DK507974A patent/DK507974A/da unknown
- 1974-09-26 FR FR7432429A patent/FR2244492A1/fr not_active Withdrawn
- 1974-09-26 FI FI2805/74A patent/FI280574A7/fi unknown
- 1974-09-26 ZA ZA00746131A patent/ZA746131B/xx unknown
- 1974-09-26 AR AR255786A patent/AR202946A1/es active
- 1974-09-26 AU AU73740/74A patent/AU7374074A/en not_active Expired

Also Published As

Publication number	Publication date
SE7412058L (fr)	1975-03-27
BE820381A (fr)	1975-03-26
DD114599A5 (fr)	1975-08-12
ZA746131B (en)	1975-09-24
FI280574A7 (fr)	1975-03-27
LU70985A1 (fr)	1975-03-06
FR2244492A1 (fr)	1975-04-18
AR202946A1 (es)	1975-07-31
DK507974A (fr)	1975-06-09
US3965128A (en)	1976-06-22
JPS5059362A (fr)	1975-05-22
DE2349024A1 (de)	1975-04-10
NL7412747A (nl)	1975-04-01
AU7374074A (en)	1976-04-01
IL45629A0 (en)	1974-11-29

Publication	Publication Date	Title
US3965128A (en)	1976-06-22	6β,7β-Epoxy-1α,2α-methylen-D-homo-4-pregnen-3,20-diones
US3682983A (en)	1972-08-08	Preparation of {66 {11 {11 -17 ethinyl steroids
NO132558B (fr)	1975-08-18
US3900467A (en)	1975-08-19	Process for the manufacture of ' 13-oxo-7' -acetylthio-17 ' hydroxy 4-androstene-17' yl)-propionic acid' -lactone
US2648663A (en)	1953-08-11	Preparation of 17alpha-hydroxy steroids
US3483226A (en)	1969-12-09	16-oxa and 17 - oxa - d - homoestra - 1,3,5(10)-trien-3-ols and d-nor-seco-diols corresponding,ethers and esters thereof
US3236868A (en)	1966-02-22	9alpha, 11beta-dichloro-17alpha-acyloxy-delta4, 6-pregnadiene-3, 20-diones and corresponding 1-dehydro derivatives
US2769823A (en)	1956-11-06	Preparation of 17alpha-hydroxy-20-keto-pregnenes
US2878246A (en)	1959-03-17	Preparation of 6-methyl steroids of the pregnane series from diosgenin
US3753979A (en)	1973-08-21	Substituted 1,2alpha-methylene-6,7alpha-halomethylene-20-spirox-4-en-3-ones or 3-ols and acyl esters thereof
US3639392A (en)	1972-02-01	Cardioactive oxido-bufatrienolides
US2673847A (en)	1954-03-30	Steroid epoxides
US3178419A (en)	1965-04-13	19-nor-steroids and process for their manufacture
US2813882A (en)	1957-11-19	delta-3, 20-diketo-17-hydroxy-11, 21-bis oxygenated-pregnadiene compounds and processes of preparing the same
US2562030A (en)	1951-07-24	Production of 17-hydroxy 20-keto steroid compounds
US3083199A (en)	1963-03-26	delta3-5alpha-steroids and 3alpha-hydroxy-5alpha-steroids and the preparation thereof
US3014936A (en)	1961-12-26	15-dehydro-cortical hormones
US3029261A (en)	1962-04-10	Steroidal fluoro compounds and process for the production thereof
US3595856A (en)	1971-07-27	17beta-hydroxy-20,21-pregnanedicarboxylic acid gamma-lactones and derivatives
US3579543A (en)	1971-05-18	Delta**1,3,5(10)-2- (or 4-)formyl-3-hydroxyoestratriene compounds
US2931806A (en)	1960-04-05	dl-delta5-3-ethylenedioxy-11-keto-20-cyano pregnenes
NO132391B (fr)	1975-07-28
US2854451A (en)	1958-09-30	11-keto-tigogenin
US2980712A (en)	1961-04-18	Allopregnane-3beta, 17alpha-diol-11, 20-dione and the preparation thereof
US3087941A (en)	1963-04-30	17alpha-bromo-6-methyl-pregnane derivatives