UA80567C2 - The hydroxyindoles, their use as inhibitors of phosphodiesterase-4 and method for production thereof - Google Patents

The hydroxyindoles, their use as inhibitors of phosphodiesterase-4 and method for production thereof Download PDF

Info

Publication number: UA80567C2
Authority: UA; Ukraine
Prior art keywords: alkyl; compounds; formula; substituents; acid
Prior art date: 2002-11-15

Application number

UAA200504467A

Other languages

English (en)

Ukrainian (uk)

Inventor

Norbert Hoefgen

Hildegard Kuss

Ute Egerland

Chris Rundfeldt

Original Assignee

Elbion Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-11-15

Filing date

2003-11-14

Publication date

2007-10-10

2003-11-14 Application filed by Elbion Ag filed Critical Elbion Ag

2007-10-10 Publication of UA80567C2 publication Critical patent/UA80567C2/uk

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 13
MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 title claims abstract description 9
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 title claims abstract description 9
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 title claims abstract description 9
239000003112 inhibitor Substances 0.000 title abstract description 14
NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 81
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
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125000001424 substituent group Chemical group 0.000 claims description 32
-1 chloride anhydrides Chemical class 0.000 claims description 21
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150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
235000015523 tannic acid Nutrition 0.000 description 1
229920002258 tannic acid Polymers 0.000 description 1
229940033123 tannic acid Drugs 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
125000001302 tertiary amino group Chemical group 0.000 description 1
238000010998 test method Methods 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
125000002640 tocopherol group Chemical class 0.000 description 1
235000019149 tocopherols Nutrition 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
230000000699 topical effect Effects 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000000230 xanthan gum Chemical class 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Chemical class 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical class [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- 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
- 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
- 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
- A61P37/08—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
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/22—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an aralkyl radical attached to the ring nitrogen atom

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Pulmonology (AREA)
Virology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Molecular Biology (AREA)
Oncology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
AIDS & HIV (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

UAA200504467A 2002-11-15 2003-11-14 The hydroxyindoles, their use as inhibitors of phosphodiesterase-4 and method for production thereof UA80567C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10253426A DE10253426B4 (de)	2002-11-15	2002-11-15	Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung
PCT/EP2003/012742 WO2004045607A1 (de)	2002-11-15	2003-11-14	Neue hydroxyindole, deren verwendung als inhibitoren der phosphodiesterase 4 und verfahren zu deren herstellung

Publications (1)

Publication Number	Publication Date
UA80567C2 true UA80567C2 (en)	2007-10-10

Family

ID=32240098

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200504467A UA80567C2 (en)	2002-11-15	2003-11-14	The hydroxyindoles, their use as inhibitors of phosphodiesterase-4 and method for production thereof

Country Status (19)

Country	Link
US (2)	US7166637B2 (de)
EP (1)	EP1562584A1 (de)
JP (1)	JP2006508141A (de)
KR (1)	KR20050075014A (de)
CN (1)	CN1711082A (de)
AR (1)	AR042053A1 (de)
AU (1)	AU2003283400A1 (de)
BR (1)	BR0316234A (de)
CA (1)	CA2505988A1 (de)
DE (1)	DE10253426B4 (de)
HR (1)	HRP20050542A2 (de)
MX (1)	MXPA05005138A (de)
NO (1)	NO20052864L (de)
PL (1)	PL376524A1 (de)
RU (1)	RU2005118409A (de)
TW (1)	TW200510306A (de)
UA (1)	UA80567C2 (de)
WO (1)	WO2004045607A1 (de)
ZA (2)	ZA200503399B (de)

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2002
- 2002-11-15 DE DE10253426A patent/DE10253426B4/de not_active Expired - Fee Related
2003
- 2003-11-13 TW TW092131851A patent/TW200510306A/zh unknown
- 2003-11-13 US US10/714,568 patent/US7166637B2/en not_active Expired - Fee Related
- 2003-11-14 JP JP2004552596A patent/JP2006508141A/ja not_active Withdrawn
- 2003-11-14 CA CA002505988A patent/CA2505988A1/en not_active Abandoned
- 2003-11-14 HR HR20050542A patent/HRP20050542A2/hr not_active Application Discontinuation
- 2003-11-14 BR BR0316234-6A patent/BR0316234A/pt not_active IP Right Cessation
- 2003-11-14 AR ARP030104219A patent/AR042053A1/es not_active Application Discontinuation
- 2003-11-14 PL PL376524A patent/PL376524A1/pl unknown
- 2003-11-14 MX MXPA05005138A patent/MXPA05005138A/es active IP Right Grant
- 2003-11-14 AU AU2003283400A patent/AU2003283400A1/en not_active Abandoned
- 2003-11-14 EP EP03775355A patent/EP1562584A1/de not_active Withdrawn
- 2003-11-14 CN CNA200380103190XA patent/CN1711082A/zh active Pending
- 2003-11-14 UA UAA200504467A patent/UA80567C2/uk unknown
- 2003-11-14 RU RU2005118409/04A patent/RU2005118409A/ru not_active Application Discontinuation
- 2003-11-14 WO PCT/EP2003/012742 patent/WO2004045607A1/de not_active Ceased
- 2003-11-14 KR KR1020057008684A patent/KR20050075014A/ko not_active Withdrawn
2005
- 2005-04-28 ZA ZA200503399A patent/ZA200503399B/en unknown
- 2005-06-13 NO NO20052864A patent/NO20052864L/no not_active Application Discontinuation
- 2005-09-01 ZA ZA200507002A patent/ZA200507002B/en unknown
2006
- 2006-11-30 US US11/606,696 patent/US20070093531A1/en not_active Abandoned

Also Published As

Publication number	Publication date
DE10253426A1 (de)	2004-06-03
AU2003283400A1 (en)	2004-06-15
PL376524A1 (pl)	2006-01-09
CA2505988A1 (en)	2004-06-03
HRP20050542A2 (en)	2005-08-31
NO20052864L (no)	2005-06-13
DE10253426B4 (de)	2005-09-22
BR0316234A (pt)	2005-10-11
KR20050075014A (ko)	2005-07-19
AR042053A1 (es)	2005-06-08
EP1562584A1 (de)	2005-08-17
MXPA05005138A (es)	2005-07-22
RU2005118409A (ru)	2006-01-20
US7166637B2 (en)	2007-01-23
TW200510306A (en)	2005-03-16
WO2004045607A1 (de)	2004-06-03
CN1711082A (zh)	2005-12-21
ZA200507002B (en)	2006-06-28
US20040147759A1 (en)	2004-07-29
JP2006508141A (ja)	2006-03-09
US20070093531A1 (en)	2007-04-26
ZA200503399B (en)	2006-06-28

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