UA72580C2 - 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1 -pyrolysine-5-yl acetic acid, a method for the preparation thereof (variants), a pharmaceutical composition based thereon and an intermediary compound - Google Patents

6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1 -pyrolysine-5-yl acetic acid, a method for the preparation thereof (variants), a pharmaceutical composition based thereon and an intermediary compound Download PDF

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Publication number: UA72580C2
Authority: UA; Ukraine
Prior art keywords: compound; ether; fact; formula; phase
Prior art date: 2000-01-28

Application number

UA2002086986A

Other languages

English (en)

Ukrainian (uk)

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.)

2000-01-28

Filing date

2001-01-26

Publication date

2005-03-15

2000-01-28 Priority claimed from MXPA/A/2000/001047A external-priority patent/MXPA00001047A/xx

2001-01-26 Application filed filed Critical

2005-03-15 Publication of UA72580C2 publication Critical patent/UA72580C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 84
238000000034 method Methods 0.000 title claims description 36
238000002360 preparation method Methods 0.000 title claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 20
239000008194 pharmaceutical composition Substances 0.000 title 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 210
239000012071 phase Substances 0.000 claims abstract description 47
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 36
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims abstract description 30
239000008346 aqueous phase Substances 0.000 claims abstract description 11
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
238000006243 chemical reaction Methods 0.000 claims description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
239000013078 crystal Substances 0.000 claims description 21
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 18
238000009835 boiling Methods 0.000 claims description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
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238000010586 diagram Methods 0.000 claims description 11
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IDLOIKCKXBJPPI-UHFFFAOYSA-N 5-benzyl-3,3-dimethyl-2,4-dihydropyrrole Chemical compound C1C(C)(C)CN=C1CC1=CC=CC=C1 IDLOIKCKXBJPPI-UHFFFAOYSA-N 0.000 claims 1
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NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
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239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000004807 desolvation Methods 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
230000029087 digestion Effects 0.000 description 1
239000000539 dimer Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000011888 foil Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000010855 food raising agent Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
235000012907 honey Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000007654 immersion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000007130 inorganic reaction Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
238000006864 oxidative decomposition reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
229920001223 polyethylene glycol Polymers 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
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
230000005855 radiation Effects 0.000 description 1
206010037844 rash Diseases 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000552 rheumatic effect Effects 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000000844 transformation Methods 0.000 description 1
230000007704 transition Effects 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
239000012808 vapor phase Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- A61P17/04—Antipruritics
- 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
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- 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
- A61P37/08—Antiallergic agents
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Dermatology (AREA)
Hematology (AREA)
Orthopedic Medicine & Surgery (AREA)
Pulmonology (AREA)
Immunology (AREA)
Diabetes (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Oncology (AREA)
Neurology (AREA)
Pain & Pain Management (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

UA2002086986A 2000-01-28 2001-01-26 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1 -pyrolysine-5-yl acetic acid, a method for the preparation thereof (variants), a pharmaceutical composition based thereon and an intermediary compound UA72580C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
MXPA/A/2000/001047A MXPA00001047A (en)		2000-01-28	Method for producing 6-(4-chlorophenyl) -2,2-dimethyl-7- phenyl -2,3-dihydro- 1h-pyrrolizine- 5-yl acetic acid
PCT/EP2001/000852 WO2001055149A1 (de)	2000-01-28	2001-01-26	Verfahren zur herstellung von 6-(4-chlorphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1h-pyrrolizin-5-yl-essigsäure

Publications (1)

Publication Number	Publication Date
UA72580C2 true UA72580C2 (en)	2005-03-15

Family

ID=32589023

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002086986A UA72580C2 (en)	2000-01-28	2001-01-26	6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1 -pyrolysine-5-yl acetic acid, a method for the preparation thereof (variants), a pharmaceutical composition based thereon and an intermediary compound

Country Status (31)

Country	Link
US (1)	US6417371B1 (ja)
EP (1)	EP1252164B1 (ja)
JP (1)	JP5143326B2 (ja)
KR (1)	KR100749222B1 (ja)
CN (1)	CN1160357C (ja)
AT (1)	ATE262529T1 (ja)
AU (1)	AU779616B2 (ja)
BG (1)	BG65567B1 (ja)
BR (1)	BR0107898A (ja)
CA (1)	CA2397767C (ja)
CU (1)	CU23193A3 (ja)
DE (1)	DE50101761D1 (ja)
DK (1)	DK1252164T3 (ja)
EA (1)	EA004938B1 (ja)
EE (1)	EE05125B1 (ja)
ES (1)	ES2218382T3 (ja)
GE (1)	GEP20043408B (ja)
HK (1)	HK1047590A1 (ja)
HR (1)	HRP20020707B1 (ja)
HU (1)	HUP0300604A3 (ja)
IS (1)	IS2404B (ja)
NZ (1)	NZ520429A (ja)
PL (1)	PL208027B1 (ja)
PT (1)	PT1252164E (ja)
RS (1)	RS50374B (ja)
SK (1)	SK286608B6 (ja)
TR (1)	TR200400691T4 (ja)
TW (1)	TWI289561B (ja)
UA (1)	UA72580C2 (ja)
WO (1)	WO2001055149A1 (ja)
ZA (1)	ZA200206832B (ja)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10141285A1 (de) *	2001-08-23	2003-03-27	Merckle Gmbh	Verfahren zur Herstellung von 6-(4-Chlorphenyl)-2,2-dimethyl-7-phnyl-2,3-dihydro-1H-pyrrolizin-5-yl-essigsäure
DE102005012971A1 (de) *	2005-03-21	2006-09-28	Merckle Gmbh	Polymorphe Form von 6-(4-Chlorphenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl-essigsäure
WO2007108006A1 (en) *	2006-03-23	2007-09-27	Unichem Laboratories Limited	Process for the preparation of 6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2, 3-dihydro-1h-pyrrolizin-5-yl acetic acid and its intermediates
PL2350082T3 (pl) *	2008-10-31	2015-08-31	C A I R Biosciences Gmbh	Sól likofelonu z choliną i trometaminą
US10206904B2 (en)	2015-07-17	2019-02-19	The Board Of Regents Of The University Of Oklahoma	Licofelone derivatives and methods of use

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5260451A (en)	1989-05-11	1993-11-09	Merckle Gmbh	Substituted pyrrole compounds and use thereof in pharmaceutical compositions
DE3915450A1 (de) *	1989-05-11	1990-11-15	Gerd Prof Dr Dannhardt	Substituierte pyrrolverbindungen und deren anwendung in der pharmazie
DE4419315A1 (de)	1994-06-01	1995-12-07	Merckle Gmbh	Heteropyrrolizinverbindungen und deren Anwendung in der Pharmazie
DE4419246A1 (de)	1994-06-01	1995-12-07	Merckle Gmbh	Heteroarylsubstituierte Pyrrolizinverbindungen und deren Anwendung in der Pharmazie
DE4419247A1 (de)	1994-06-01	1995-12-07	Merckle Gmbh	Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie

2001
- 2001-01-26 AT AT01905691T patent/ATE262529T1/de active
- 2001-01-26 GE GE4919A patent/GEP20043408B/en unknown
- 2001-01-26 SK SK1043-2002A patent/SK286608B6/sk not_active IP Right Cessation
- 2001-01-26 UA UA2002086986A patent/UA72580C2/uk unknown
- 2001-01-26 HU HU0300604A patent/HUP0300604A3/hu unknown
- 2001-01-26 BR BR0107898-4A patent/BR0107898A/pt not_active Application Discontinuation
- 2001-01-26 CA CA002397767A patent/CA2397767C/en not_active Expired - Fee Related
- 2001-01-26 TR TR2004/00691T patent/TR200400691T4/xx unknown
- 2001-01-26 KR KR1020027009706A patent/KR100749222B1/ko active IP Right Grant
- 2001-01-26 RS YUP-565/02A patent/RS50374B/sr unknown
- 2001-01-26 NZ NZ520429A patent/NZ520429A/en not_active IP Right Cessation
- 2001-01-26 DE DE50101761T patent/DE50101761D1/de not_active Expired - Lifetime
- 2001-01-26 EP EP01905691A patent/EP1252164B1/de not_active Expired - Lifetime
- 2001-01-26 PL PL356774A patent/PL208027B1/pl unknown
- 2001-01-26 JP JP2001561008A patent/JP5143326B2/ja not_active Expired - Fee Related
- 2001-01-26 WO PCT/EP2001/000852 patent/WO2001055149A1/de active IP Right Grant
- 2001-01-26 EA EA200200740A patent/EA004938B1/ru not_active IP Right Cessation
- 2001-01-26 DK DK01905691T patent/DK1252164T3/da active
- 2001-01-26 EE EEP200200417A patent/EE05125B1/xx not_active IP Right Cessation
- 2001-01-26 CN CNB01804235XA patent/CN1160357C/zh not_active Expired - Fee Related
- 2001-01-26 ES ES01905691T patent/ES2218382T3/es not_active Expired - Lifetime
- 2001-01-26 US US09/769,742 patent/US6417371B1/en not_active Expired - Lifetime
- 2001-01-26 AU AU33711/01A patent/AU779616B2/en not_active Ceased
- 2001-01-26 PT PT01905691T patent/PT1252164E/pt unknown
- 2001-05-09 TW TW090111072A patent/TWI289561B/zh not_active IP Right Cessation
2002
- 2002-07-17 CU CU20020150A patent/CU23193A3/es not_active IP Right Cessation
- 2002-07-19 IS IS6475A patent/IS2404B/is unknown
- 2002-07-24 BG BG106951A patent/BG65567B1/bg unknown
- 2002-08-27 ZA ZA200206832A patent/ZA200206832B/en unknown
- 2002-08-28 HR HR20020707A patent/HRP20020707B1/xx not_active IP Right Cessation
- 2002-12-17 HK HK02109153A patent/HK1047590A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
HRP20020707B1 (en)	2006-05-31
US6417371B1 (en)	2002-07-09
CN1160357C (zh)	2004-08-04
NZ520429A (en)	2003-08-29
GEP20043408B (en)	2004-06-10
US20020028953A1 (en)	2002-03-07
EE05125B1 (et)	2009-02-16
BR0107898A (pt)	2002-11-05
HRP20020707A2 (en)	2004-12-31
PL208027B1 (pl)	2011-03-31
BG106951A (en)	2003-07-31
TR200400691T4 (tr)	2004-11-22
AU3371101A (en)	2001-08-07
TWI289561B (en)	2007-11-11
JP5143326B2 (ja)	2013-02-13
YU56502A (sh)	2005-06-10
EE200200417A (et)	2003-12-15
RS50374B (sr)	2009-11-10
SK286608B6 (sk)	2009-02-05
CA2397767C (en)	2008-05-06
EA004938B1 (ru)	2004-10-28
DK1252164T3 (da)	2004-07-05
CA2397767A1 (en)	2001-08-02
KR20020075895A (ko)	2002-10-07
CU23193A3 (es)	2007-03-23
WO2001055149A1 (de)	2001-08-02
JP2004517799A (ja)	2004-06-17
ES2218382T3 (es)	2004-11-16
BG65567B1 (bg)	2008-12-30
EP1252164B1 (de)	2004-03-24
IS6475A (is)	2002-07-19
EA200200740A1 (ru)	2002-12-26
ZA200206832B (en)	2003-10-07
PT1252164E (pt)	2004-08-31
EP1252164A1 (de)	2002-10-30
DE50101761D1 (de)	2004-04-29
SK10432002A3 (sk)	2003-02-04
IS2404B (is)	2008-09-15
PL356774A1 (en)	2004-07-12
AU779616B2 (en)	2005-02-03
HUP0300604A2 (hu)	2003-07-28
HK1047590A1 (en)	2003-02-28
HUP0300604A3 (en)	2003-10-28
KR100749222B1 (ko)	2007-08-13
ATE262529T1 (de)	2004-04-15
CN1396922A (zh)	2003-02-12

Publication	Publication Date	Title
TW200526595A (en)	2005-08-16	Chemical compounds
FR2651497A1 (fr)	1991-03-08	Nouveaux sels de metaux bivalents de l'acide n, n-di (carboxymethyl)amino-2 cyano-3 carboxymethyl-4 carboxy-5 thiophene, leur procede de preparation et les compositions pharmaceutiques les renfermant.
JP2009263377A (ja)	2009-11-12	カリウムチャネルモジュレーター
JP2008514729A (ja)	2008-05-08	スピロ−ヒダントイン化合物の結晶形および製造方法
KR20140009125A (ko)	2014-01-22	당뇨병 및 이상지질혈증 치료 방법 및 조성물
JP2021063111A (ja)	2021-04-22	二メシル酸パルボシクリブの固体形態
JP2005514454A6 (ja)	2005-08-04	カリウムチャネルモジュレーター
UA72580C2 (en)	2005-03-15	6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1 -pyrolysine-5-yl acetic acid, a method for the preparation thereof (variants), a pharmaceutical composition based thereon and an intermediary compound
KR101418624B1 (ko)	2014-07-15	Ｎ｛２플루오로5［３（티오펜２카보닐）피라졸로［１，５ａ］피리미딘７일］페닐｝ｎ메틸아세트아미드의 다형체 ｂ
FI83958B (fi)	1991-06-14	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara, substituerade 8-tiotetrahydrokinoliner samt deras salter.
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