OA12894A - Crystal forms of quinoxaline-2-carboxylic acid [4-carbamoy 1-1-(3-fluorobenzyl)-2,7-dihydroxy-7-met hyl-octyl]-amide. - Google Patents

Crystal forms of quinoxaline-2-carboxylic acid [4-carbamoy 1-1-(3-fluorobenzyl)-2,7-dihydroxy-7-met hyl-octyl]-amide. Download PDF

Info

Publication number: OA12894A
Authority: OA; OAPI
Prior art keywords: dihydroxy; octyl; quinoxaline; carboxylic acid; carbamoyl
Prior art date: 2002-08-12

Application number

OA1200500028A

Other languages

English (en)

Inventor

John Charles Kath

Zheng Jane Li

Zhengong Bryan Li

Eric Brock Mcelroy

Clifford Nathaniel Meltz

Christopher Stanley Poss

Original Assignee

Pfizer Prod Inc

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.)

2002-08-12

Filing date

2003-07-31

Publication date

2006-10-13

2003-07-31 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2006-10-13 Publication of OA12894A publication Critical patent/OA12894A/en

Links

239000013078 crystal Substances 0.000 title claims abstract description 68
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YEQJVHQCUDMXFG-UHFFFAOYSA-N n-[5-carbamoyl-1-(3-fluorophenyl)-3,8-dihydroxy-8-methylnonan-2-yl]quinoxaline-2-carboxamide Chemical compound C=1N=C2C=CC=CC2=NC=1C(=O)NC(C(O)CC(CCC(C)(O)C)C(N)=O)CC1=CC=CC(F)=C1 YEQJVHQCUDMXFG-UHFFFAOYSA-N 0.000 claims abstract description 29
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UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229960003444 immunosuppressant agent Drugs 0.000 description 1
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239000012535 impurity Substances 0.000 description 1
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229910052738 indium Inorganic materials 0.000 description 1
APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
125000000686 lactone group Chemical group 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
UPRXAOPZPSAYHF-UHFFFAOYSA-N lithium;cyclohexyl(propan-2-yl)azanide Chemical compound CC(C)N([Li])C1CCCCC1 UPRXAOPZPSAYHF-UHFFFAOYSA-N 0.000 description 1
244000144972 livestock Species 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004698 lymphocyte Anatomy 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
229940032007 methylethyl ketone Drugs 0.000 description 1
HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
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238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
YZIVBPNWAKJRRQ-UHFFFAOYSA-N n-[2-(3-fluorophenyl)-1-[4-(3-methylbut-2-enyl)-5-oxooxolan-2-yl]ethyl]quinoxaline-2-carboxamide Chemical compound O1C(=O)C(CC=C(C)C)CC1C(NC(=O)C=1N=C2C=CC=CC2=NC=1)CC1=CC=CC(F)=C1 YZIVBPNWAKJRRQ-UHFFFAOYSA-N 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
229960002009 naproxen Drugs 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229960005489 paracetamol Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
229960002702 piroxicam Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
229960004618 prednisone Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
SOPDQKNXOCUBSR-UHFFFAOYSA-N quinoxaline-2-carbonyl chloride Chemical compound C1=CC=CC2=NC(C(=O)Cl)=CN=C21 SOPDQKNXOCUBSR-UHFFFAOYSA-N 0.000 description 1
VRUYRTGYUJTBRQ-UHFFFAOYSA-N quinoxaline-2-carbonyl chloride;quinoxaline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CN=C21.C1=CC=CC2=NC(C(=O)Cl)=CN=C21 VRUYRTGYUJTBRQ-UHFFFAOYSA-N 0.000 description 1
ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000405 serological effect Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
229960002930 sirolimus Drugs 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000009987 spinning Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LXIKEPCNDFVJKC-QXMHVHEDSA-N tenidap Chemical compound C12=CC(Cl)=CC=C2N(C(=O)N)C(=O)\C1=C(/O)C1=CC=CS1 LXIKEPCNDFVJKC-QXMHVHEDSA-N 0.000 description 1
229960003676 tenidap Drugs 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
239000003104 tissue culture media Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/08—Antibacterial agents for leprosy
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Virology (AREA)
Dermatology (AREA)
Physical Education & Sports Medicine (AREA)
AIDS & HIV (AREA)
Molecular Biology (AREA)
Pulmonology (AREA)
Tropical Medicine & Parasitology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)

OA1200500028A 2002-08-12 2003-07-31 Crystal forms of quinoxaline-2-carboxylic acid [4-carbamoy 1-1-(3-fluorobenzyl)-2,7-dihydroxy-7-met hyl-octyl]-amide. OA12894A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US40321602P	2002-08-12	2002-08-12

Publications (1)

Publication Number	Publication Date
OA12894A true OA12894A (en)	2006-10-13

Family

ID=31715961

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200500028A OA12894A (en)	2002-08-12	2003-07-31	Crystal forms of quinoxaline-2-carboxylic acid [4-carbamoy 1-1-(3-fluorobenzyl)-2,7-dihydroxy-7-met hyl-octyl]-amide.

Country Status (22)

Country	Link
US (1)	US20040072834A1 (fr)
EP (1)	EP1539715A1 (fr)
JP (1)	JP2005538130A (fr)
AP (1)	AP2005003226A0 (fr)
AR (1)	AR040839A1 (fr)
AU (1)	AU2003250450A1 (fr)
BR (1)	BR0313378A (fr)
CA (1)	CA2494776A1 (fr)
EC (1)	ECSP055588A (fr)
GT (1)	GT200300169A (fr)
IL (1)	IL166548A0 (fr)
IS (1)	IS7674A (fr)
MX (1)	MXPA05001781A (fr)
NO (1)	NO20050540L (fr)
OA (1)	OA12894A (fr)
PA (1)	PA8580401A1 (fr)
PE (1)	PE20040866A1 (fr)
TN (1)	TNSN05035A1 (fr)
TW (1)	TW200407316A (fr)
UY (1)	UY27928A1 (fr)
WO (1)	WO2004014875A1 (fr)
ZA (1)	ZA200500768B (fr)

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JP5731538B2 (ja)	2009-12-23	2015-06-10	アイアンウッドファーマシューティカルズインコーポレイテッド	Ｃｒｔｈ２モジュレーター
WO2012009137A1 (fr)	2010-07-12	2012-01-19	Ironwood Pharmaceuticals, Inc.	Modulateurs de crth2
US20130259830A1 (en)	2010-07-12	2013-10-03	Ironwood Pharmaceuticals, Inc.	Crth2 modulators
CN102276539B (zh) *	2011-06-29	2013-08-14	赵雪梅	一种具有抑菌作用的化合物及其制备方法

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BE640616A (fr) *	1962-12-19
US3492397A (en) *	1967-04-07	1970-01-27	Warner Lambert Pharmaceutical	Sustained release dosage in the pellet form and process thereof
US4060598A (en) *	1967-06-28	1977-11-29	Boehringer Mannheim G.M.B.H.	Tablets coated with aqueous resin dispersions
US3538214A (en) *	1969-04-22	1970-11-03	Merck & Co Inc	Controlled release medicinal tablets
US4173626A (en) *	1978-12-11	1979-11-06	Merck & Co., Inc.	Sustained release indomethacin
WO1998038167A1 (fr) *	1997-02-26	1998-09-03	Pfizer Inc.	Derives amines de l'acide heteroaryle-hexanoique, leur preparation, et leur utilisation comme inhibiteurs selectifs du mip-1 alpha par fixation a son recepteur ccr1
UA57824C2 (uk) *	1998-02-05	2003-07-15	Пфайзер Продактс Інк.	Похідні дигідроксигексанової кислоти, фармацевтична композиція, що їх містить (варіанти), та спосіб лікування (варіанти)

2003
- 2003-07-31 WO PCT/IB2003/003464 patent/WO2004014875A1/fr not_active Ceased
- 2003-07-31 AP AP2005003226A patent/AP2005003226A0/xx unknown
- 2003-07-31 CA CA002494776A patent/CA2494776A1/fr not_active Abandoned
- 2003-07-31 OA OA1200500028A patent/OA12894A/en unknown
- 2003-07-31 MX MXPA05001781A patent/MXPA05001781A/es not_active Application Discontinuation
- 2003-07-31 JP JP2004527195A patent/JP2005538130A/ja active Pending
- 2003-07-31 BR BR0313378-8A patent/BR0313378A/pt not_active Application Discontinuation
- 2003-07-31 AU AU2003250450A patent/AU2003250450A1/en not_active Abandoned
- 2003-07-31 EP EP03784383A patent/EP1539715A1/fr not_active Withdrawn
- 2003-08-05 UY UY27928A patent/UY27928A1/es not_active Application Discontinuation
- 2003-08-06 GT GT200300169A patent/GT200300169A/es unknown
- 2003-08-06 TW TW092121503A patent/TW200407316A/zh unknown
- 2003-08-08 US US10/637,475 patent/US20040072834A1/en not_active Abandoned
- 2003-08-08 AR AR20030102881A patent/AR040839A1/es unknown
- 2003-08-08 PE PE2003000794A patent/PE20040866A1/es not_active Application Discontinuation
- 2003-08-12 PA PA20038580401A patent/PA8580401A1/es unknown
2005
- 2005-01-26 ZA ZA200500768A patent/ZA200500768B/xx unknown
- 2005-01-27 IL IL16654805A patent/IL166548A0/xx unknown
- 2005-01-27 IS IS7674A patent/IS7674A/is unknown
- 2005-01-31 NO NO20050540A patent/NO20050540L/no unknown
- 2005-02-03 EC EC2005005588A patent/ECSP055588A/es unknown
- 2005-02-11 TN TNP2005000035A patent/TNSN05035A1/fr unknown

Also Published As

Publication number	Publication date
IS7674A (is)	2005-01-27
TW200407316A (en)	2004-05-16
ECSP055588A (es)	2005-04-18
ZA200500768B (en)	2006-07-26
AP2005003226A0 (en)	2005-03-31
JP2005538130A (ja)	2005-12-15
BR0313378A (pt)	2005-07-12
UY27928A1 (es)	2004-03-31
NO20050540L (no)	2005-03-10
PA8580401A1 (es)	2004-02-16
CA2494776A1 (fr)	2004-02-19
WO2004014875A1 (fr)	2004-02-19
US20040072834A1 (en)	2004-04-15
GT200300169A (es)	2004-05-12
MXPA05001781A (es)	2005-04-25
PE20040866A1 (es)	2004-11-26
IL166548A0 (en)	2006-01-15
EP1539715A1 (fr)	2005-06-15
AR040839A1 (es)	2005-04-20
AU2003250450A1 (en)	2004-02-25
TNSN05035A1 (fr)	2007-05-14

Publication	Publication Date	Title
DE10064105A1 (de)	2002-06-27	Neue Substituierte Imidazotriazinone
DE10108752A1 (de)	2002-09-05	Neue Substituierte Imidazotriazinone
DE69811360T2 (de)	2003-10-09	Diazepinoindolone als phophodiesterase 4 inhibitoren
JP2020528433A (ja)	2020-09-24	アリピプラゾールラウロキシルの調製方法
FR2656609A1 (fr)	1991-07-05	Derives de 2-aminopyrimidine-4-carboxamide, leur preparation et leur application en therapeutique.
JP5202129B2 (ja)	2013-06-05	５−ヒドロキシ−１−メチルヒダントインの製造方法
OA12894A (en)	2006-10-13	Crystal forms of quinoxaline-2-carboxylic acid [4-carbamoy 1-1-(3-fluorobenzyl)-2,7-dihydroxy-7-met hyl-octyl]-amide.
JPH0615527B2 (ja)	1994-03-02	アルキルジアミン誘導体、その製造法および抗不整脈剤
JPS6379876A (ja)	1988-04-09	新規なナフチル誘導体、その製造法およびそれらの化合物を含有する医薬組成物
Timberlake et al.	1989	Synthesis of 1, 2, 5-thiadiazolidin-3-one 1, 1-dioxides: x-ray structure determination of 4, 4-diphenyl-1, 2, 5-thiadiazolidin-3-one 1, 1-dioxide
CN112745255A (zh)	2021-05-04	一种btk激酶抑制剂的制备方法
CA2155849A1 (fr)	1994-08-18	Nouveaux derives heterocycliques de l'aminomethyl-4 piperidine, leur preparation et leur application en therapeutique
EP0146787B1 (fr)	1988-08-17	Dérivés d'indole, médicaments contenant ces composés et procédé pour leur preparation
HK56697A (en)	1997-05-09	Substituted piperazines, their process of preparation and the pharmaceutical compositions containing them
NL8000289A (nl)	1980-08-04	Werkwijze ter bereiding van 6,7-dimethoxy-4-amino- -2-4-(2-furoyl)-1-piperazinyl chinazolinehydro- chloride met een antihypertensieve werking.
KR20050046005A (ko)	2005-05-17	퀴녹살린-2-카르복실산[4-카르바모일-1-(3-플루오로벤질)-2,7-디히드록시-7-메틸-옥틸]-아미드의 결정형
DE69607622T2 (de)	2000-08-31	Verfahren zur herstellung von ethyl 3s[[4-[[4-(aminoiminomethyl)phenyl)amino)-2,4-dioxobutyl)amino)-4-pentynsäure
EP0461012B1 (fr)	1994-04-20	Dérivés de (1-phénylpyrrolidin-2-yl)méthylpipérazine, leur préparation et leur application en thérapeutique
EP0055145A1 (fr)	1982-06-30	Dérivés de l'acide (aminométhyl)-4 cyclohexane-carboxylique-1
Pfeiffer et al.	1988	A short synthesis of 4‐imidazolidinone
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US6858744B2 (en)	2005-02-22	Dihydoxyhexanoic acid derivatives, their intermediates, and methods of making
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EP1210340A1 (fr)	2002-06-05	Derives de piperazine substitues, leur fabrication et leur utilisation comme medicaments