SK284260B6 - Deriváty cykloalkano-indolu a cykloalkano-azaindolu, spôsob ich výroby, farmaceutické prostriedky tieto látky obsahujúce a ich použitie - Google Patents

Deriváty cykloalkano-indolu a cykloalkano-azaindolu, spôsob ich výroby, farmaceutické prostriedky tieto látky obsahujúce a ich použitie Download PDF

Info

Publication number: SK284260B6
Authority: SK; Slovakia
Prior art keywords: group; carbon atoms; phenyl; cycloalkano; linear
Prior art date: 1994-10-04

Application number

SK1239-95A

Other languages

English (en)

Slovak (sk)

Other versions

SK123995A3 (en

Inventor

Ulrich MLLER

Richard Connell

Siegfried Goldmann

Rudi Gr�Tzmann

Martin Beuck

Hilmar Bischoff

Dirk Denzer

Anke Domdey-Bette

Stefan Wohlfeil

Original Assignee

Bayer Aktiengesellschaft

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.)

1994-10-04

Filing date

1995-10-03

Publication date

2004-12-01

1995-10-03 Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft

1996-06-05 Publication of SK123995A3 publication Critical patent/SK123995A3/sk

2004-12-01 Publication of SK284260B6 publication Critical patent/SK284260B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 18
230000008569 process Effects 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 7
239000003814 drug Substances 0.000 claims abstract description 7
238000004519 manufacturing process Methods 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 98
239000002253 acid Substances 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 35
-1 nitro, carboxyl Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
125000003944 tolyl group Chemical group 0.000 claims description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
238000006722 reduction reaction Methods 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229940059260 amidate Drugs 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
238000005304 joining Methods 0.000 claims 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 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 1
229940079593 drug Drugs 0.000 abstract description 3
230000000879 anti-atherosclerotic effect Effects 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 120
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
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125000000623 heterocyclic group Chemical group 0.000 description 28
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239000000203 mixture Substances 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
210000002966 serum Anatomy 0.000 description 16
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MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
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241000700159 Rattus Species 0.000 description 13
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YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 12
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
239000012043 crude product Substances 0.000 description 11
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 11
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 11
102000006991 Apolipoprotein B-100 Human genes 0.000 description 10
108010008150 Apolipoprotein B-100 Proteins 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000002585 base Substances 0.000 description 10
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 10
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238000012360 testing method Methods 0.000 description 10
241000416162 Astragalus gummifer Species 0.000 description 9
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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239000011734 sodium Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
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238000005160 1H NMR spectroscopy Methods 0.000 description 8
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238000004587 chromatography analysis Methods 0.000 description 8
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000012071 phase Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
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230000000694 effects Effects 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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239000007858 starting material Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Child & Adolescent Psychology (AREA)
Hospice & Palliative Care (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)

SK1239-95A 1994-10-04 1995-10-03 Deriváty cykloalkano-indolu a cykloalkano-azaindolu, spôsob ich výroby, farmaceutické prostriedky tieto látky obsahujúce a ich použitie SK284260B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4435477A DE4435477A1 (de)	1994-10-04	1994-10-04	Cycloalkano-indol- und -azaindol-derivate

Publications (2)

Publication Number	Publication Date
SK123995A3 SK123995A3 (en)	1996-06-05
SK284260B6 true SK284260B6 (sk)	2004-12-01

Family

ID=6529939

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1239-95A SK284260B6 (sk)	1994-10-04	1995-10-03	Deriváty cykloalkano-indolu a cykloalkano-azaindolu, spôsob ich výroby, farmaceutické prostriedky tieto látky obsahujúce a ich použitie

Country Status (35)

Country	Link
US (6)	US5684014A (fr)
EP (1)	EP0705831B1 (fr)
JP (1)	JP3901234B2 (fr)
KR (1)	KR100355986B1 (fr)
CN (2)	CN1050605C (fr)
AT (1)	ATE255580T1 (fr)
AU (1)	AU700609B2 (fr)
CA (1)	CA2159546C (fr)
CZ (1)	CZ291348B6 (fr)
DE (2)	DE4435477A1 (fr)
DK (1)	DK0705831T3 (fr)
DZ (1)	DZ1934A1 (fr)
EE (1)	EE03527B1 (fr)
ES (1)	ES2211890T3 (fr)
FI (2)	FI113048B (fr)
HN (1)	HN1995009160A (fr)
HR (1)	HRP950505B1 (fr)
HU (1)	HU225052B1 (fr)
IL (3)	IL115493A (fr)
MA (1)	MA23683A1 (fr)
MY (1)	MY117282A (fr)
NO (1)	NO305365B1 (fr)
NZ (1)	NZ280130A (fr)
PH (1)	PH31400A (fr)
PL (1)	PL183154B1 (fr)
PT (1)	PT705831E (fr)
RU (1)	RU2157803C2 (fr)
SG (1)	SG63528A1 (fr)
SI (1)	SI0705831T1 (fr)
SK (1)	SK284260B6 (fr)
SV (1)	SV1995000062A (fr)
TN (1)	TNSN95098A1 (fr)
TW (1)	TW448175B (fr)
UA (1)	UA44700C2 (fr)
ZA (1)	ZA958297B (fr)

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WO2004063156A1 (fr) *	2003-01-08	2004-07-29	Biovitrum Ab	Nouveaux derives d'indole utiles comme inhibiteurs de fabp-4
WO2005051382A1 (fr) *	2003-11-28	2005-06-09	Astellas Pharma Inc.	Agent renforçant l'effet hypolipidemiant
US7649002B2 (en)	2004-02-04	2010-01-19	Pfizer Inc	(3,5-dimethylpiperidin-1yl)(4-phenylpyrrolidin-3-yl)methanone derivatives as MCR4 agonists
US7932268B2 (en)	2004-03-05	2011-04-26	The Trustees Of The University Of Pennsylvania	Methods for treating disorders or diseases associated with hyperlipidemia and hypercholesterolemia while minimizing side effects
US7262318B2 (en) *	2004-03-10	2007-08-28	Pfizer, Inc.	Substituted heteroaryl- and phenylsulfamoyl compounds
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US20050288340A1 (en) *	2004-06-29	2005-12-29	Pfizer Inc	Substituted heteroaryl- and phenylsulfamoyl compounds
US20060030623A1 (en) *	2004-07-16	2006-02-09	Noboru Furukawa	Agent for the treatment or prevention of diabetes, obesity or arteriosclerosis
FR2873694B1 (fr) *	2004-07-27	2006-12-08	Merck Sante Soc Par Actions Si	Nouveaux aza-indoles inhibiteurs de la mtp et apob
US8101774B2 (en) *	2004-10-18	2012-01-24	Japan Tobacco Inc.	Ester derivatives and medicinal use thereof
AU2005297923B2 (en) *	2004-10-25	2010-12-23	Japan Tobacco Inc.	Solid medicinal preparation improved in solubility and stability and process for producing the same
PA8660701A1 (es)	2005-02-04	2006-09-22	Pfizer Prod Inc	Agonistas de pyy y sus usos
JP2008542255A (ja) *	2005-05-27	2008-11-27	ファイザー・プロダクツ・インク	肥満症の治療または体重減量の維持のためのカンナビノイド−１受容体アンタゴニストおよびミクロソームトリグリセリド輸送タンパク質阻害物質の併用
WO2007015162A1 (fr) *	2005-08-04	2007-02-08	Pfizer Limited	Composes piperidinoyl-pyrrolidine et piperidinoyl-piperidine
EP1951220A2 (fr) *	2005-10-18	2008-08-06	Aegerion Pharmaceuticals	Compositions destinees a l'abbaissement du cholesterol serique et/ou des triglycerides
US7741317B2 (en)	2005-10-21	2010-06-22	Bristol-Myers Squibb Company	LXR modulators
US7888376B2 (en)	2005-11-23	2011-02-15	Bristol-Myers Squibb Company	Heterocyclic CETP inhibitors
ES2402581T3 (es) *	2006-02-23	2013-05-06	Pfizer Limited	Piperidinoilpirrolidinas como agonistas del receptor de melanocortina tipo 4
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CN101663262B (zh)	2006-12-01	2014-03-26	百时美施贵宝公司	用于治疗动脉粥样硬化和心血管疾病的作为cetp抑制剂的n-(3-苄基)-2,2-(二苯基)-丙-1胺衍生物
CA2673290A1 (fr) *	2006-12-21	2008-07-03	Aegerion Pharmaceuticals, Inc.	Procedes de traitement de l'obesite a l'aide d'une combinaison comprenant un inhibiteur de mtp et un inhibiteur de l'absorption du cholesterol
RU2338745C1 (ru) *	2007-03-21	2008-11-20	Андрей Александрович Иващенко	ЗАМЕЩЕННЫЕ 2,3,4,5-ТЕТРАГИДРО-1Н-ПИРИДО[4,3-b]ИНДОЛЫ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ
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JP5530438B2 (ja) *	2008-08-06	2014-06-25	ファイザー・リミテッド	Ｍｃ４作動薬としてのジアゼピンおよびジアゾカン化合物
CN105120863B (zh)	2013-03-14	2021-06-04	奥斯特克有限公司	促进骨生长的烷基胺骆驼蓬碱衍生物
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CN108218862B (zh) *	2018-02-07	2020-06-23	贵州医科大学	α-卡波林类衍生物在制备抗心肌缺氧复氧损伤药物中的应用
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DE4435477A1 (de) *	1994-10-04	1996-04-11	Bayer Ag	Cycloalkano-indol- und -azaindol-derivate
DE19613549A1 (de)	1996-04-04	1997-10-09	Bayer Ag	Verfahren zur Herstellung von enantiomerenreinen Cycloalkano-indol- und azaindol-carbonsäuren und deren aktivierte Derivate
DE19615119A1 (de) *	1996-04-17	1997-10-23	Bayer Ag	Neue Arylessigsäureamide

1994
- 1994-10-04 DE DE4435477A patent/DE4435477A1/de not_active Withdrawn
1995
- 1995-02-07 HN HN1995009160A patent/HN1995009160A/es unknown
- 1995-09-21 SI SI9530693T patent/SI0705831T1/xx unknown
- 1995-09-21 PT PT95114877T patent/PT705831E/pt unknown
- 1995-09-21 ES ES95114877T patent/ES2211890T3/es not_active Expired - Lifetime
- 1995-09-21 DK DK95114877T patent/DK0705831T3/da active
- 1995-09-21 EP EP95114877A patent/EP0705831B1/fr not_active Expired - Lifetime
- 1995-09-21 DE DE59510839T patent/DE59510839D1/de not_active Expired - Lifetime
- 1995-09-21 AT AT95114877T patent/ATE255580T1/de not_active IP Right Cessation
- 1995-09-27 AU AU32920/95A patent/AU700609B2/en not_active Ceased
- 1995-09-27 HR HR950505A patent/HRP950505B1/xx not_active IP Right Cessation
- 1995-09-28 US US08/535,698 patent/US5684014A/en not_active Expired - Lifetime
- 1995-09-29 NZ NZ280130A patent/NZ280130A/en not_active IP Right Cessation
- 1995-09-29 CA CA2159546A patent/CA2159546C/fr not_active Expired - Fee Related
- 1995-10-02 TW TW084110247A patent/TW448175B/zh active
- 1995-10-02 IL IL11549395A patent/IL115493A/xx not_active IP Right Cessation
- 1995-10-02 IL IL12964199A patent/IL129641A0/xx unknown
- 1995-10-02 FI FI954681A patent/FI113048B/fi active
- 1995-10-02 DZ DZ950116A patent/DZ1934A1/fr active
- 1995-10-02 KR KR1019950033651A patent/KR100355986B1/ko not_active Expired - Fee Related
- 1995-10-02 TN TNTNSN95098A patent/TNSN95098A1/fr unknown
- 1995-10-02 MA MA24027A patent/MA23683A1/fr unknown
- 1995-10-02 IL IL12964195A patent/IL129641A/xx not_active IP Right Cessation
- 1995-10-03 RU RU95117070/04A patent/RU2157803C2/ru not_active IP Right Cessation
- 1995-10-03 HU HU9502891A patent/HU225052B1/hu not_active IP Right Cessation
- 1995-10-03 SK SK1239-95A patent/SK284260B6/sk not_active IP Right Cessation
- 1995-10-03 ZA ZA958297A patent/ZA958297B/xx unknown
- 1995-10-03 EE EE9500071A patent/EE03527B1/xx not_active IP Right Cessation
- 1995-10-03 PL PL95310756A patent/PL183154B1/pl not_active IP Right Cessation
- 1995-10-03 JP JP27966495A patent/JP3901234B2/ja not_active Expired - Fee Related
- 1995-10-03 NO NO953930A patent/NO305365B1/no not_active IP Right Cessation
- 1995-10-03 PH PH51415A patent/PH31400A/en unknown
- 1995-10-03 CZ CZ19952567A patent/CZ291348B6/cs not_active IP Right Cessation
- 1995-10-03 UA UA95104372A patent/UA44700C2/uk unknown
- 1995-10-03 SG SG1995001478A patent/SG63528A1/en unknown
- 1995-10-04 CN CN95117117A patent/CN1050605C/zh not_active Expired - Fee Related
- 1995-10-04 SV SV1995000062A patent/SV1995000062A/es active IP Right Grant
- 1995-10-04 MY MYPI95002964A patent/MY117282A/en unknown
- 1995-10-04 CN CNB981260853A patent/CN1183111C/zh not_active Expired - Fee Related
1997
- 1997-07-03 US US08/887,781 patent/US6245775B1/en not_active Expired - Lifetime
1999
- 1999-05-17 US US09/313,035 patent/US6265431B1/en not_active Expired - Lifetime
2000
- 2000-12-08 FI FI20002693A patent/FI108791B/fi active
- 2000-12-11 US US09/734,955 patent/US20020147209A1/en not_active Abandoned
2001
- 2001-03-21 US US09/814,263 patent/US6479503B2/en not_active Expired - Lifetime
2002
- 2002-07-18 US US10/198,315 patent/US6858622B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
FI20002693L (fi)	2000-12-08
US6858622B2 (en)	2005-02-22
EP0705831A2 (fr)	1996-04-10
PL183154B1 (pl)	2002-05-31
TW448175B (en)	2001-08-01
CN1130631A (zh)	1996-09-11
US20030149073A1 (en)	2003-08-07
RU2157803C2 (ru)	2000-10-20
JPH08225526A (ja)	1996-09-03
IL129641A (en)	2000-08-31
KR960014126A (ko)	1996-05-22
FI954681A0 (fi)	1995-10-02
DE59510839D1 (de)	2004-01-15
NZ280130A (en)	1996-05-28
EE03527B1 (et)	2001-10-15
HN1995009160A (es)	2000-04-24
DE4435477A1 (de)	1996-04-11
NO953930D0 (no)	1995-10-03
CA2159546C (fr)	2010-12-14
FI113048B (fi)	2004-02-27
DZ1934A1 (fr)	2002-02-17
HRP950505B1 (en)	2002-04-30
CA2159546A1 (fr)	1996-04-05
MY117282A (en)	2004-06-30
US6265431B1 (en)	2001-07-24
HU9502891D0 (en)	1995-11-28
CN1224715A (zh)	1999-08-04
IL115493A (en)	1999-10-28
UA44700C2 (uk)	2002-03-15
SI0705831T1 (en)	2004-02-29
PH31400A (en)	1998-10-29
US20020147209A1 (en)	2002-10-10
ZA958297B (en)	1996-05-06
AU700609B2 (en)	1999-01-07
SG63528A1 (en)	1999-03-30
IL129641A0 (en)	2000-02-29
PL310756A1 (en)	1996-04-15
JP3901234B2 (ja)	2007-04-04
HUT73240A (en)	1996-07-29
HRP950505A2 (en)	1997-08-31
CZ291348B6 (cs)	2003-02-12
DK0705831T3 (da)	2004-04-05
FI954681A7 (fi)	1996-04-05
CN1050605C (zh)	2000-03-22
ES2211890T3 (es)	2004-07-16
HK1005139A1 (en)	1998-12-24
MA23683A1 (fr)	1996-07-01
NO953930L (no)	1996-04-09
NO305365B1 (no)	1999-05-18
CZ256795A3 (en)	1996-04-17
EP0705831A3 (fr)	1997-01-22
PT705831E (pt)	2004-04-30
TNSN95098A1 (fr)	1996-02-06
SK123995A3 (en)	1996-06-05
US6479503B2 (en)	2002-11-12
EE9500071A (et)	1996-04-15
US6245775B1 (en)	2001-06-12
ATE255580T1 (de)	2003-12-15
AU3292095A (en)	1996-04-18
HU225052B1 (en)	2006-05-29
KR100355986B1 (ko)	2003-01-06
SV1995000062A (es)	1996-07-10
EP0705831B1 (fr)	2003-12-03
CN1183111C (zh)	2005-01-05
FI108791B (fi)	2002-03-28
US5684014A (en)	1997-11-04
US20020055635A1 (en)	2002-05-09
IL115493A0 (en)	1996-01-19

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Publication	Publication Date	Title
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