SK283316B6 - Substituované benzamidy a ich použitie - Google Patents

Substituované benzamidy a ich použitie Download PDF

Info

Publication number: SK283316B6
Authority: SK; Slovakia
Prior art keywords: formula; carbon atoms; group; radical; straight
Prior art date: 1998-09-24

Application number

SK1308-99A

Other languages

English (en)

Slovak (sk)

Other versions

SK130899A3 (en

Inventor

Tieno Germann

Stefanie Frosch

Oswald Zimmer

Original Assignee

Grnenthal Gmbh

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.)

1998-09-24

Filing date

1999-09-23

Publication date

2003-05-02

1999-09-23 Application filed by Grnenthal Gmbh filed Critical Grnenthal Gmbh

2000-06-12 Publication of SK130899A3 publication Critical patent/SK130899A3/sk

2003-05-02 Publication of SK283316B6 publication Critical patent/SK283316B6/sk

Links

150000003936 benzamides Chemical class 0.000 title claims abstract description 13
229940054066 benzamide antipsychotics Drugs 0.000 title claims abstract description 10
239000002955 immunomodulating agent Substances 0.000 title claims abstract description 9
229940121354 immunomodulator Drugs 0.000 title claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
230000002584 immunomodulator Effects 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 description 14
210000001616 monocyte Anatomy 0.000 description 14
239000000126 substance Substances 0.000 description 11
201000010099 disease Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
208000023275 Autoimmune disease Diseases 0.000 description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 6
230000002757 inflammatory effect Effects 0.000 description 6
230000004054 inflammatory process Effects 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
102000004127 Cytokines Human genes 0.000 description 4
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230000019734 interleukin-12 production Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 4
201000004624 Dermatitis Diseases 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
206010009887 colitis Diseases 0.000 description 3
230000001506 immunosuppresive effect Effects 0.000 description 3
210000002540 macrophage Anatomy 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
210000004400 mucous membrane Anatomy 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000011231 Crohn disease Diseases 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
241000282412 Homo Species 0.000 description 2
101000946889 Homo sapiens Monocyte differentiation antigen CD14 Proteins 0.000 description 2
208000022559 Inflammatory bowel disease Diseases 0.000 description 2
102100037850 Interferon gamma Human genes 0.000 description 2
108010074328 Interferon-gamma Proteins 0.000 description 2
102100035877 Monocyte differentiation antigen CD14 Human genes 0.000 description 2
BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
230000004913 activation Effects 0.000 description 2
208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
238000010171 animal model Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000001514 detection method Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
229960003957 dexamethasone Drugs 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
230000002519 immonomodulatory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
230000003902 lesion Effects 0.000 description 2
239000011325 microbead Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
201000006417 multiple sclerosis Diseases 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
238000010606 normalization Methods 0.000 description 2
229960001476 pentoxifylline Drugs 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000001737 promoting effect Effects 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 2
229950005741 rolipram Drugs 0.000 description 2
239000002904 solvent Substances 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
208000024891 symptom Diseases 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
238000011282 treatment Methods 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
KRXOUFMTPNHYGO-UHFFFAOYSA-N 2-(morpholine-4-carbonyl)-n-[1-(morpholin-4-ylmethyl)-2,6-dioxopiperidin-3-yl]benzamide Chemical compound C=1C=CC=C(C(=O)N2CCOCC2)C=1C(=O)NC(C1=O)CCC(=O)N1CN1CCOCC1 KRXOUFMTPNHYGO-UHFFFAOYSA-N 0.000 description 1
OQOZUZCUNBVHLC-UHFFFAOYSA-N 2-[[1-(morpholin-4-ylmethyl)-2,6-dioxopiperidin-3-yl]carbamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1C(=O)N(CN2CCOCC2)C(=O)CC1 OQOZUZCUNBVHLC-UHFFFAOYSA-N 0.000 description 1
206010003011 Appendicitis Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
MXPCDEAOUOIMLM-UHFFFAOYSA-N CCN(C1CC(=O)N(C(=O)C1)CN2CCCCC2)C(=O)C3=CC=CC=C3C(=O)N Chemical compound CCN(C1CC(=O)N(C(=O)C1)CN2CCCCC2)C(=O)C3=CC=CC=C3C(=O)N MXPCDEAOUOIMLM-UHFFFAOYSA-N 0.000 description 1
206010006895 Cachexia Diseases 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
206010012438 Dermatitis atopic Diseases 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
206010016654 Fibrosis Diseases 0.000 description 1
229920001917 Ficoll Polymers 0.000 description 1
102000012153 HLA-B27 Antigen Human genes 0.000 description 1
108010061486 HLA-B27 Antigen Proteins 0.000 description 1
206010062016 Immunosuppression Diseases 0.000 description 1
108010002352 Interleukin-1 Proteins 0.000 description 1
238000006683 Mannich reaction Methods 0.000 description 1
206010027202 Meningitis bacterial Diseases 0.000 description 1
-1 Morpholine-4-carbonyl Chemical group 0.000 description 1
206010028116 Mucosal inflammation Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010033645 Pancreatitis Diseases 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
201000010001 Silicosis Diseases 0.000 description 1
206010052779 Transplant rejections Diseases 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
206010046851 Uveitis Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
208000037883 airway inflammation Diseases 0.000 description 1
239000013566 allergen Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
201000008937 atopic dermatitis Diseases 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
201000009904 bacterial meningitis Diseases 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
239000007910 chewable tablet Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
238000000432 density-gradient centrifugation Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
239000002329 esterase inhibitor Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
208000024908 graft versus host disease Diseases 0.000 description 1
239000008187 granular material Substances 0.000 description 1
210000003714 granulocyte Anatomy 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000036039 immunity Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000031261 interleukin-10 production Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000011835 investigation Methods 0.000 description 1
206010023332 keratitis Diseases 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
206010034674 peritonitis Diseases 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
230000010410 reperfusion Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000003118 sandwich ELISA Methods 0.000 description 1
201000000306 sarcoidosis Diseases 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
241000894007 species Species 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000011580 syndromic disease Diseases 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
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
230000003827 upregulation Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Immunology (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

SK1308-99A 1998-09-24 1999-09-23 Substituované benzamidy a ich použitie SK283316B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19843793A DE19843793C2 (de)	1998-09-24	1998-09-24	Substituierte Benzamide

Publications (2)

Publication Number	Publication Date
SK130899A3 SK130899A3 (en)	2000-06-12
SK283316B6 true SK283316B6 (sk)	2003-05-02

Family

ID=7882078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1308-99A SK283316B6 (sk)	1998-09-24	1999-09-23	Substituované benzamidy a ich použitie

Country Status (26)

Country	Link
US (1)	US6080742A (cs)
EP (1)	EP0989121B1 (cs)
JP (1)	JP2000095761A (cs)
KR (1)	KR20000023339A (cs)
CN (1)	CN1126741C (cs)
AR (1)	AR021814A1 (cs)
AT (1)	ATE309987T1 (cs)
AU (1)	AU750919B2 (cs)
BR (1)	BR9906070A (cs)
CA (1)	CA2283021A1 (cs)
CO (1)	CO5160263A1 (cs)
CZ (1)	CZ295496B6 (cs)
DE (2)	DE19843793C2 (cs)
DK (1)	DK0989121T3 (cs)
ES (1)	ES2251143T3 (cs)
HU (1)	HUP9903216A3 (cs)
IL (1)	IL132012A (cs)
NO (1)	NO312671B1 (cs)
NZ (1)	NZ337531A (cs)
PE (1)	PE20001050A1 (cs)
PL (1)	PL194897B1 (cs)
RU (1)	RU2221783C2 (cs)
SI (1)	SI0989121T1 (cs)
SK (1)	SK283316B6 (cs)
UY (1)	UY25712A1 (cs)
ZA (1)	ZA996133B (cs)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10002509A1 (de) *	2000-01-21	2001-07-26	Gruenenthal Gmbh	Substituierte Glutarimide
WO2001070688A2 (de) *	2000-03-20	2001-09-27	Grünenthal GmbH	N-(2,6-dioxo-piperidin-3-yl) benzamide und ihre verwendung als immunomodulatoren
US20050118137A1 (en) *	2000-07-19	2005-06-02	Chih-Ping Liu	Method of treatment using interferon-tau
US20050118138A1 (en) *	2000-07-19	2005-06-02	Chih-Ping Liu	Method of treatment using interferon-tau
US20050201981A1 (en) *	2004-03-10	2005-09-15	Chih-Ping Liu	Method of optimizing treatment with interferon-tau
US20050084478A1 (en) *	2000-10-17	2005-04-21	Chih-Ping Liu	Combination therapy using interferon-tau
US20040247565A1 (en) *	2000-07-19	2004-12-09	Chih-Ping Liu	Method of treatment using interferon-tau
US7431920B2 (en) *	2000-07-19	2008-10-07	Pepgen Corporation	Method of treating IL-10 deficiency
US20050226845A1 (en) *	2004-03-10	2005-10-13	Chih-Ping Liu	Method of treatment using interferon-tau
EP1188438A1 (en) *	2000-09-15	2002-03-20	Warner-Lambert Company	Pharmaceutical composition for preventing or treating a disease associated with an excess of Il-12 production
EP1199074A1 (en) *	2000-09-15	2002-04-24	Warner-Lambert Company	Pharmaceutical composition for preventing or treating a disease associated with an excess of il-12 production
EP1389203B8 (en) *	2001-02-27	2010-03-10	The Governement of the United States of America, represented by The Secretary Department of Health and Human services	Analogs of thalidomide as angiogenesis inhibitors
US6479493B1 (en)	2001-08-23	2002-11-12	Cell Pathways, Inc.	Methods for treatment of type I diabetes
WO2003037365A1 (en) *	2001-11-01	2003-05-08	The Johns Hopkins University	Methods and compositions for treating vascular leak using hepatocyte growth factor
DE10163595A1 (de) *	2001-12-21	2003-08-07	Gruenenthal Gmbh	In 3-Position heterocyclisch substituierte Piperidin-2,6-dione
US8952895B2 (en)	2011-06-03	2015-02-10	Apple Inc.	Motion-based device operations
WO2005028436A2 (en)	2003-09-17	2005-03-31	The Government Of The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services	Thalidomide analogs as tnf-alpha modulators
US20080025948A1 (en) *	2004-03-10	2008-01-31	Chih-Ping Liu	Methods of Treatment Using Interferon-Tau
US20060078942A1 (en) *	2004-03-10	2006-04-13	Pepgen Corporation	Method of treatment using interferon-tau
DE102004026703A1 (de) *	2004-05-28	2005-12-29	Grünenthal GmbH	Verfahren zur Herstellung von in 3-Position heterocyclisch substituierten Piperidin-2,6-dionen
CA2648216C (en) *	2006-04-13	2016-06-07	Michael Gutschow	Tetrahalogenated compounds useful as inhibitors of angiogenesis
JP5658138B2 (ja) *	2008-04-23	2015-01-21	ライジェルファーマシューティカルズ，インコーポレイテッド	代謝障害の処置のためのカルボキサミド化合物
US8927725B2 (en)	2011-12-02	2015-01-06	The United States Of America, As Represented By The Secretary, Department Of Health And Human Services	Thio compounds
KR102316961B1 (ko) *	2020-01-29	2021-10-26	프라비바이오 주식회사	면역억제제로서의 벤젠 유도체의 면역억제용 약학적 조성물

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1545672B2 (de) *	1965-05-08	1974-11-07	Chemie Gruenenthal Gmbh, 5190 Stolberg	Dikarbonsäureimidderivate und Verfahren zu ihrer Herstellung
GB8928043D0 (en) *	1989-12-12	1990-02-14	Pfizer Ltd	Muscarinic receptor antagonists

1998
- 1998-09-24 DE DE19843793A patent/DE19843793C2/de not_active Expired - Fee Related
1999
- 1999-08-27 NZ NZ337531A patent/NZ337531A/xx not_active IP Right Cessation
- 1999-09-03 AT AT99117319T patent/ATE309987T1/de active
- 1999-09-03 DE DE59912795T patent/DE59912795D1/de not_active Expired - Lifetime
- 1999-09-03 DK DK99117319T patent/DK0989121T3/da active
- 1999-09-03 ES ES99117319T patent/ES2251143T3/es not_active Expired - Lifetime
- 1999-09-03 SI SI9930863T patent/SI0989121T1/sl unknown
- 1999-09-03 EP EP99117319A patent/EP0989121B1/de not_active Expired - Lifetime
- 1999-09-15 UY UY25712A patent/UY25712A1/es unknown
- 1999-09-17 PE PE1999000942A patent/PE20001050A1/es not_active Application Discontinuation
- 1999-09-17 AR ARP990104701A patent/AR021814A1/es unknown
- 1999-09-21 CO CO99059817A patent/CO5160263A1/es unknown
- 1999-09-21 KR KR1019990040635A patent/KR20000023339A/ko not_active Ceased
- 1999-09-22 CA CA002283021A patent/CA2283021A1/en not_active Abandoned
- 1999-09-22 AU AU48861/99A patent/AU750919B2/en not_active Ceased
- 1999-09-22 JP JP11269084A patent/JP2000095761A/ja not_active Withdrawn
- 1999-09-22 HU HU9903216A patent/HUP9903216A3/hu unknown
- 1999-09-23 ZA ZA9906133A patent/ZA996133B/xx unknown
- 1999-09-23 IL IL13201299A patent/IL132012A/en not_active IP Right Cessation
- 1999-09-23 PL PL335555A patent/PL194897B1/pl not_active IP Right Cessation
- 1999-09-23 SK SK1308-99A patent/SK283316B6/sk not_active IP Right Cessation
- 1999-09-23 RU RU99120663/04A patent/RU2221783C2/ru not_active IP Right Cessation
- 1999-09-23 NO NO19994626A patent/NO312671B1/no not_active IP Right Cessation
- 1999-09-23 CN CN99120232A patent/CN1126741C/zh not_active Expired - Fee Related
- 1999-09-23 CZ CZ19993386A patent/CZ295496B6/cs not_active IP Right Cessation
- 1999-09-23 BR BR9906070-1A patent/BR9906070A/pt not_active IP Right Cessation
- 1999-09-24 US US09/405,180 patent/US6080742A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
NO312671B1 (no)	2002-06-17
PE20001050A1 (es)	2000-11-18
NZ337531A (en)	2000-09-29
SK130899A3 (en)	2000-06-12
HUP9903216A3 (en)	2000-10-30
CO5160263A1 (es)	2002-05-30
CA2283021A1 (en)	2000-03-24
UY25712A1 (es)	2001-05-31
JP2000095761A (ja)	2000-04-04
PL335555A1 (en)	2000-03-27
CZ295496B6 (cs)	2005-08-17
EP0989121A1 (de)	2000-03-29
HU9903216D0 (en)	1999-11-29
BR9906070A (pt)	2000-08-15
ZA996133B (en)	2000-04-06
EP0989121B1 (de)	2005-11-16
PL194897B1 (pl)	2007-07-31
AU750919B2 (en)	2002-08-01
CZ338699A3 (cs)	2000-08-16
IL132012A0 (en)	2001-03-19
CN1126741C (zh)	2003-11-05
AR021814A1 (es)	2002-08-07
SI0989121T1 (sl)	2006-04-30
AU4886199A (en)	2000-03-30
NO994626L (no)	2000-03-27
ATE309987T1 (de)	2005-12-15
RU2221783C2 (ru)	2004-01-20
IL132012A (en)	2004-02-19
NO994626D0 (no)	1999-09-23
DE19843793A1 (de)	2000-04-20
CN1250048A (zh)	2000-04-12
KR20000023339A (ko)	2000-04-25
DE59912795D1 (de)	2005-12-22
DK0989121T3 (da)	2005-12-12
HK1026211A1 (en)	2000-12-08
US6080742A (en)	2000-06-27
DE19843793C2 (de)	2000-08-03
HUP9903216A2 (hu)	2000-06-28
ES2251143T3 (es)	2006-04-16

Legal Events

Date	Code	Title	Description
2011-06-06	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20100923

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