NO321536B1 - 3<alfa>-Hydroksy-3<beta>-metoksymetyl-21-heterocyklisk substituerte steroider med bedovende aktivitet - Google Patents

3<alfa>-Hydroksy-3<beta>-metoksymetyl-21-heterocyklisk substituerte steroider med bedovende aktivitet Download PDF

Info

Publication number: NO321536B1
Authority: NO; Norway
Prior art keywords: methoxymethyl; hydroxy; compound; pregnan; imidazolyl
Prior art date: 1999-04-29

Application number

NO20015262A

Other languages

English (en)

Norwegian (no)

Other versions

NO20015262L (no

NO20015262D0 (no

Inventor

Derk J Hogenkamp

Original Assignee

Euro Celtique Sa

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.)

1999-04-29

Filing date

2001-10-26

Publication date

2006-05-22

2001-10-26 Application filed by Euro Celtique Sa filed Critical Euro Celtique Sa

2001-10-26 Publication of NO20015262D0 publication Critical patent/NO20015262D0/no

2001-12-19 Publication of NO20015262L publication Critical patent/NO20015262L/no

2006-05-22 Publication of NO321536B1 publication Critical patent/NO321536B1/no

Links

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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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125000002950 monocyclic group Chemical group 0.000 claims description 6
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
239000000651 prodrug Substances 0.000 claims description 5
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208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 4
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
229940075419 choline hydroxide Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011281 clinical therapy Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010579 first pass effect Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
238000012792 lyophilization process Methods 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229940068918 polyethylene glycol 400 Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
OVYWMEWYEJLIER-UHFFFAOYSA-N quinolin-6-ol Chemical compound N1=CC=CC2=CC(O)=CC=C21 OVYWMEWYEJLIER-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000012439 solid excipient Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
230000002618 waking effect Effects 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Anesthesiology (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)

NO20015262A 1999-04-29 2001-10-26 3<alfa>-Hydroksy-3<beta>-metoksymetyl-21-heterocyklisk substituerte steroider med bedovende aktivitet NO321536B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US13157899P	1999-04-29	1999-04-29
PCT/US2000/011680 WO2000066614A1 (en)	1999-04-29	2000-04-28	3α-HYDROXY-3β METHOXYMETHYL-21-HETEROCYCLE SUBSTITUTED STEROIDS WITH ANESTHETIC ACTIVITY

Publications (3)

Publication Number	Publication Date
NO20015262D0 NO20015262D0 (no)	2001-10-26
NO20015262L NO20015262L (no)	2001-12-19
NO321536B1 true NO321536B1 (no)	2006-05-22

Family

ID=22450073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20015262A NO321536B1 (no)	1999-04-29	2001-10-26	3<alfa>-Hydroksy-3<beta>-metoksymetyl-21-heterocyklisk substituerte steroider med bedovende aktivitet

Country Status (20)

Country	Link
US (2)	US20040034002A1 (zh)
EP (1)	EP1177206A1 (zh)
JP (1)	JP2002543218A (zh)
KR (1)	KR20020013530A (zh)
CN (1)	CN1187367C (zh)
AU (1)	AU780989B2 (zh)
BR (1)	BR0010060A (zh)
CA (1)	CA2372342A1 (zh)
CZ (1)	CZ20013867A3 (zh)
HU (1)	HUP0201818A3 (zh)
IL (1)	IL146230A0 (zh)
MX (1)	MXPA01010915A (zh)
NO (1)	NO321536B1 (zh)
NZ (1)	NZ515779A (zh)
PL (1)	PL351438A1 (zh)
RU (1)	RU2243232C2 (zh)
UA (1)	UA73736C2 (zh)
WO (1)	WO2000066614A1 (zh)
YU (1)	YU77701A (zh)
ZA (1)	ZA200109847B (zh)

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005105822A2 (en) *	2004-04-23	2005-11-10	Euro-Celtique S.A.	3-alpha-hydroxy 21-n- heteroaryl-pregnane derivatives for modulation of brain excitability and a process for the production thereof
US20060074059A1 (en) *	2004-08-26	2006-04-06	Goliber Philip A	Isomorphic crystalline habits of 3alpha-hydroxy-21-(1'-imidazolyl)-3beta-methoxymethyl-5alpha-pregnane-20-one
NZ562979A (en) *	2005-06-09	2010-11-26	Euro Celtique Sa	Pharmaceutical compositions of a pregnanone steroid which provide specific steady state plasma levels and uses thereof
DE102008058436B4 (de) *	2008-11-21	2019-03-07	Osram Opto Semiconductors Gmbh	Kantenemittierender Halbleiterlaserchip
HRP20230747T1 (hr) *	2011-09-08	2024-01-05	Sage Therapeutics, Inc.	Neuroaktivni steroidi, pripravci i njihova uporaba
AU2012323888A1 (en) *	2011-10-14	2014-05-29	Sage Therapeutics, Inc.	3,3 disubstituted 19-nor pregnane compounds, compositions, and uses thereof
IL310348A (en) *	2013-04-17	2024-03-01	Sage Therapeutics Inc	19-nor c3,3-disubstituted c21-n-pyrazolyl steroids and methods of use thereof
EP3719030B1 (en)	2013-04-17	2024-07-10	Sage Therapeutics, Inc.	19-nor neuroactive steroids for inducing sedation
WO2014169836A1 (en)	2013-04-17	2014-10-23	Sage Therapeutics, Inc.	19-nor neuroactive steroids and methods of use thereof
WO2014169831A1 (en)	2013-04-17	2014-10-23	Sage Therapeutics, Inc.	19-nor c3,3-disubstituted c21-c-bound heteroaryl steroids and methods of use thereof
EP3868382A1 (en)	2013-07-19	2021-08-25	Sage Therapeutics, Inc.	Neuroactive steroids, compositions, and uses thereof
ES2848823T3 (es)	2013-08-23	2021-08-12	Sage Therapeutics Inc	Esteroides neuroactivos, composiciones y usos de los mismos
US20180179247A1 (en) *	2014-05-29	2018-06-28	Sage Therapeutics, Inc.	Neuroactive steroids, compositions, and uses thereof
WO2015195962A1 (en)	2014-06-18	2015-12-23	Sage Therapeutics, Inc.	Neuroactive steroids, compositions, and uses thereof
KR102612943B1 (ko) *	2014-10-16	2023-12-13	세이지 테라퓨틱스, 인크.	Cns 장애의 치료를 위한 조성물 및 방법
RS60642B1 (sr)	2014-10-16	2020-09-30	Sage Therapeutics Inc	Kompozicije i postupci za lečenje poremećaja cns-a
SMT202000276T1 (it)	2014-11-27	2020-07-08	Sage Therapeutics Inc	Composizioni e metodi per trattare disturbi del snc
SMT202100113T1 (it)	2015-01-26	2021-05-07	Sage Therapeutics Inc	Composizioni e metodi per trattare disturbi del snc
EP3258939B1 (en)	2015-02-20	2022-09-07	Sage Therapeutics, Inc.	Neuroactive steroids, compositions, and uses thereof
ES2865258T3 (es)	2015-07-06	2021-10-15	Sage Therapeutics Inc	Oxiesteroles y procedimientos de uso de los mismos
MA44526A (fr)	2016-04-01	2021-06-02	Sage Therapeutics Inc	Oxystérols et leurs méthodes d'utilisation
JP7049313B2 (ja)	2016-07-11	2022-04-06	セージセラピューティクス，インコーポレイテッド	Ｃ１７、ｃ２０、およびｃ２１置換神経刺激性ステロイドおよびそれらの使用方法
WO2018013615A1 (en)	2016-07-11	2018-01-18	Sage Therapeutics, Inc.	C7, c12, and c16 substituted neuroactive steroids and their methods of use
MA46351A (fr)	2016-09-30	2021-06-02	Sage Therapeutics Inc	Oxystérols substitués en c7 et procédés en tant que modulateurs nmda
EP4105223B1 (en)	2016-10-18	2025-04-30	Sage Therapeutics, Inc.	Oxysterols and methods of use thereof
US10562930B1 (en) *	2018-08-31	2020-02-18	Praxis Precision Medicines, Inc.	Salts and crystal forms of GABAA positive allosteric modulator
US12325726B2 (en)	2018-12-17	2025-06-10	Intra-Cellular Therapies, Inc.	Organic compounds
PH12021553005A1 (en)	2019-05-31	2023-08-14	Sage Therapeutics Inc	Neuroactive steroids and compositions thereof
US20230414636A1 (en)	2020-03-25	2023-12-28	Sage Therapeutics, Inc.	Use of gabaa modulators for treatment of respiratory conditions
WO2022040545A1 (en) *	2020-08-20	2022-02-24	Intra-Cellular Therapies, Inc.	Organic compounds
US20240148756A1 (en)	2021-02-18	2024-05-09	Sage Therapeutics, Inc.	Use of neuroactive steroid for treatment of sexual dysfunction
WO2023159035A1 (en)	2022-02-16	2023-08-24	Sage Therapeutics, Inc.	Neuroactive steroids for treatment of cns-related disorders
WO2023159094A2 (en) *	2022-02-16	2023-08-24	Praxis Precision Medicines, Inc.	PROCESS OF MAKING 3α-HYDROXY-3β-METHOXYMETHYL-21-(1'- IMIDAZOLYL)-5α-PREGNAN-20-ONE
WO2023164386A1 (en)	2022-02-28	2023-08-31	Sage Therapeutics, Inc.	Neuroactive steroids for treatment of gastrointestinal diseases or conditions
CN120917034A (zh) *	2023-05-11	2025-11-07	上海枢境生物科技有限公司	甾体类化合物、制备方法及其用途

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3953429A (en) *	1970-12-17	1976-04-27	Glaxo Laboratories Limited	Anaesthetic steroids of the androstance and pregnane series
US3943124A (en) *	1970-12-17	1976-03-09	Gordon Hanley Phillipps	Chemical compounds
US3969345A (en) *	1970-12-17	1976-07-13	Glaxo Laboratories Limited	20β,21-Epoxy-3α-hydroxy-5α-pregnanes and derivatives thereof
GB1377608A (en) *	1970-12-17	1974-12-18	Glaxo Lab Ltd	3alpha-hydroxy or acyloxy pregnene-21-ethers
US3959260A (en) *	1972-05-05	1976-05-25	Glaxo Laboratories Limited	Anaesthetic steroids of the pregnane and 19-norpregnane series having a sulfur-containing group at the 21-position
GB1436324A (en) *	1972-05-12	1976-05-19	Glaxo Lab Ltd	Anaesthetic 3alpha-hydroxy pregnanes
US4192871A (en) *	1976-01-06	1980-03-11	Glaxo Laboratories Limited	Chemical compounds
US4197296A (en) *	1977-03-23	1980-04-08	Glaxo Group Limited	Androstanes
US4297350A (en) *	1978-10-10	1981-10-27	The Upjohn Company	Male contraceptive steroids and methods of use
US5319115A (en) *	1987-08-25	1994-06-07	Cocensys Inc.	Method for making 3α-hydroxy, 3β-substituted-pregnanes
US5120723A (en) *	1987-08-25	1992-06-09	University Of Southern California	Method, compositions, and compounds for modulating brain excitability
US5232917A (en) *	1987-08-25	1993-08-03	University Of Southern California	Methods, compositions, and compounds for allosteric modulation of the GABA receptor by members of the androstane and pregnane series
US5208227A (en) *	1987-08-25	1993-05-04	University Of Southern California	Method, compositions, and compounds for modulating brain excitability
US4898694A (en) *	1987-11-25	1990-02-06	Schwartz Arthur G	17-Hydroxy-steroids
DK0752860T3 (da) *	1994-02-14	2000-11-13	Euro Celtique Sa	Androstaner og pregnaner til allosterisk modulering af GABA-receptor
US5939545A (en) *	1994-02-14	1999-08-17	Cocensys, Inc.	Method, compositions, and compounds for allosteric modulation of the gaba receptor by members of the androstane and pregnane series
ES2235187T3 (es) *	1995-06-06	2005-07-01	Euro-Celtique S.A.	Esteroides neuroactivos de las series del androstano y el pregnano.

2000
- 2000-04-28 MX MXPA01010915A patent/MXPA01010915A/es unknown
- 2000-04-28 CZ CZ20013867A patent/CZ20013867A3/cs unknown
- 2000-04-28 KR KR1020017013819A patent/KR20020013530A/ko not_active Ceased
- 2000-04-28 EP EP00930250A patent/EP1177206A1/en not_active Withdrawn
- 2000-04-28 PL PL00351438A patent/PL351438A1/xx not_active Application Discontinuation
- 2000-04-28 JP JP2000615643A patent/JP2002543218A/ja not_active Withdrawn
- 2000-04-28 UA UA2001118125A patent/UA73736C2/uk unknown
- 2000-04-28 CN CNB008083606A patent/CN1187367C/zh not_active Expired - Fee Related
- 2000-04-28 NZ NZ515779A patent/NZ515779A/en unknown
- 2000-04-28 CA CA002372342A patent/CA2372342A1/en not_active Abandoned
- 2000-04-28 IL IL14623000A patent/IL146230A0/xx unknown
- 2000-04-28 AU AU48104/00A patent/AU780989B2/en not_active Ceased
- 2000-04-28 YU YU77701A patent/YU77701A/sh unknown
- 2000-04-28 HU HU0201818A patent/HUP0201818A3/hu unknown
- 2000-04-28 WO PCT/US2000/011680 patent/WO2000066614A1/en not_active Ceased
- 2000-04-28 BR BR0010060-9A patent/BR0010060A/pt not_active IP Right Cessation
- 2000-04-28 RU RU2001132583/04A patent/RU2243232C2/ru not_active IP Right Cessation
2001
- 2001-10-26 NO NO20015262A patent/NO321536B1/no unknown
- 2001-11-29 ZA ZA200109847A patent/ZA200109847B/xx unknown
2003
- 2003-08-15 US US10/641,073 patent/US20040034002A1/en not_active Abandoned
2005
- 2005-01-03 US US11/027,682 patent/US20050171074A1/en not_active Abandoned

Also Published As

Publication number	Publication date
NO20015262L (no)	2001-12-19
NO20015262D0 (no)	2001-10-26
HK1047594A1 (zh)	2003-02-28
CN1360591A (zh)	2002-07-24
HUP0201818A3 (en)	2004-04-28
CN1187367C (zh)	2005-02-02
PL351438A1 (en)	2003-04-22
AU780989B2 (en)	2005-04-28
YU77701A (sh)	2005-07-19
WO2000066614A8 (en)	2001-03-15
RU2243232C2 (ru)	2004-12-27
AU4810400A (en)	2000-11-17
BR0010060A (pt)	2002-01-15
CA2372342A1 (en)	2000-11-09
UA73736C2 (en)	2005-09-15
US20050171074A1 (en)	2005-08-04
ZA200109847B (en)	2003-02-26
HUP0201818A2 (en)	2002-10-28
NZ515779A (en)	2003-11-28
IL146230A0 (en)	2002-07-25
KR20020013530A (ko)	2002-02-20
WO2000066614A1 (en)	2000-11-09
US20040034002A1 (en)	2004-02-19
JP2002543218A (ja)	2002-12-17
EP1177206A1 (en)	2002-02-06
CZ20013867A3 (cs)	2002-07-17
MXPA01010915A (es)	2002-11-07

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US20170349624A1 (en)	2017-12-07	Pro-drug forming compounds
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