NO312764B1 - Benzonaftyridiner som bronkialterapeutika - Google Patents

Benzonaftyridiner som bronkialterapeutika Download PDF

Info

Publication number: NO312764B1
Authority: NO; Norway
Prior art keywords: compounds; cis; methyl; naphthyridine; hexahydrobenzo
Prior art date: 1996-11-11

Application number

NO19992282A

Other languages

English (en)

Norwegian (no)

Other versions

NO992282D0 (no

NO992282L (no

Inventor

Beate Gutterer

Wolf-Ruediger Ulrich

Thomas Martin

Thomas Baer

Hermann Amschler

Dietrich Haefner

Armin Hatzelmann

Hans-Peter Kley

Karl Sanders

Karl-Josef Goebel

Rolf Beume

Dieter Flockerzi

Hildegard Boss

Original Assignee

Takeda 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.)

1996-11-11

Filing date

1999-05-11

Publication date

2002-07-01

1999-05-11 Application filed by Takeda Gmbh filed Critical Takeda Gmbh

1999-05-11 Publication of NO992282D0 publication Critical patent/NO992282D0/no

1999-05-11 Publication of NO992282L publication Critical patent/NO992282L/no

2002-07-01 Publication of NO312764B1 publication Critical patent/NO312764B1/no

Links

239000003814 drug Substances 0.000 title claims abstract description 15
BJVCSICIEDHBNI-UHFFFAOYSA-N benzo[b][1,8]naphthyridine Chemical class N1=CC=CC2=CC3=CC=CC=C3N=C21 BJVCSICIEDHBNI-UHFFFAOYSA-N 0.000 title description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 141
150000001875 compounds Chemical class 0.000 claims description 107
-1 1-piperidyl Chemical group 0.000 claims description 45
150000003839 salts Chemical class 0.000 claims description 42
230000003287 optical effect Effects 0.000 claims description 39
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 16
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
229940079593 drug Drugs 0.000 claims description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
BWYRUGYLRJXRFN-AXEKQOJOSA-N (3r,4s)-3-(3,4-diethoxyphenyl)-1-methylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1=C(OCC)C(OCC)=CC=C1[C@H]1[C@@H](N)CCN(C)C1 BWYRUGYLRJXRFN-AXEKQOJOSA-N 0.000 claims description 2
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150000002431 hydrogen Chemical class 0.000 claims 3
CVDXFPBVOIERBH-DQEYMECFSA-N 4-[(4as,10br)-9-ethoxy-8-methoxy-2-methyl-3,4,4a,10b-tetrahydro-1h-benzo[c][1,6]naphthyridin-6-yl]-n,n-di(propan-2-yl)benzamide Chemical compound N([C@H]1CCN(C)C[C@H]1C=1C=C(C(=CC=11)OC)OCC)=C1C1=CC=C(C(=O)N(C(C)C)C(C)C)C=C1 CVDXFPBVOIERBH-DQEYMECFSA-N 0.000 claims 1
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
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HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
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XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
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GOZNZGWCQSNZFX-UHFFFAOYSA-N 1,6-naphthyridine;hydrochloride Chemical compound Cl.C1=CN=CC2=CC=CN=C21 GOZNZGWCQSNZFX-UHFFFAOYSA-N 0.000 description 2
QYQKEEKSROGRBQ-UHFFFAOYSA-N 6-phenylbenzo[b][1,8]naphthyridine Chemical class C1=CC=CC=C1C1=CC=CC2=NC3=NC=CC=C3C=C12 QYQKEEKSROGRBQ-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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239000002547 new drug Substances 0.000 description 1
210000001331 nose Anatomy 0.000 description 1
108010028584 nucleotidase Proteins 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
210000003695 paranasal sinus Anatomy 0.000 description 1
244000045947 parasite Species 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000035699 permeability Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
210000003800 pharynx Anatomy 0.000 description 1
239000002570 phosphodiesterase III inhibitor Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
230000010118 platelet activation Effects 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
JDHDNVYHHODZLJ-GOTSBHOMSA-N propan-2-yl 4-[[(3R,4S)-3-(3,4-diethoxyphenyl)-1-methylpiperidin-4-yl]carbamoyl]benzoate Chemical compound C(C)(C)OC(C1=CC=C(C(=O)N[C@@H]2[C@@H](CN(CC2)C)C2=CC(=C(C=C2)OCC)OCC)C=C1)=O JDHDNVYHHODZLJ-GOTSBHOMSA-N 0.000 description 1
RYTMPLWNLQTRKQ-SFTDATJTSA-N propan-2-yl 4-[[(3R,4S)-3-(3,4-dimethoxyphenyl)-1-methylpiperidin-4-yl]carbamoyl]benzoate Chemical compound C(C)(C)OC(C1=CC=C(C(=O)N[C@@H]2[C@@H](CN(CC2)C)C2=CC(=C(C=C2)OC)OC)C=C1)=O RYTMPLWNLQTRKQ-SFTDATJTSA-N 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
230000037387 scars Effects 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
230000035939 shock Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000003998 snake venom Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
238000009121 systemic therapy Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000002883 vasorelaxation effect Effects 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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
- 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
- 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
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A61P25/00—Drugs for disorders of the nervous 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
- 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
- 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
- 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

Landscapes

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

NO19992282A 1996-11-11 1999-05-11 Benzonaftyridiner som bronkialterapeutika NO312764B1 (no)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19646298		1996-11-11
EP96118188		1996-11-13
DE19739056		1997-09-05
PCT/EP1997/006096 WO1998021208A1 (en)	1996-11-11	1997-11-05	Benzonaphthyridines as bronchial therapeutics

Publications (3)

Publication Number	Publication Date
NO992282D0 NO992282D0 (no)	1999-05-11
NO992282L NO992282L (no)	1999-05-11
NO312764B1 true NO312764B1 (no)	2002-07-01

Family

ID=27216810

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19992282A NO312764B1 (no)	1996-11-11	1999-05-11	Benzonaftyridiner som bronkialterapeutika

Country Status (31)

Country	Link
US (1)	US6008215A (zh)
EP (1)	EP0937074B1 (zh)
JP (1)	JP4223075B2 (zh)
KR (1)	KR100484045B1 (zh)
CN (1)	CN1090188C (zh)
AT (1)	ATE234300T1 (zh)
AU (1)	AU733129B2 (zh)
BG (1)	BG63695B1 (zh)
BR (1)	BR9713338B1 (zh)
CA (1)	CA2270964C (zh)
CY (1)	CY2476B1 (zh)
CZ (1)	CZ288752B6 (zh)
DE (1)	DE69719778T2 (zh)
DK (1)	DK0937074T3 (zh)
EA (1)	EA001551B1 (zh)
EE (1)	EE03829B1 (zh)
ES (1)	ES2195189T3 (zh)
GE (1)	GEP20012390B (zh)
HK (1)	HK1022151A1 (zh)
HU (1)	HU226981B1 (zh)
ID (1)	ID22042A (zh)
IL (1)	IL129054A (zh)
NO (1)	NO312764B1 (zh)
NZ (1)	NZ334976A (zh)
PL (1)	PL189641B1 (zh)
PT (1)	PT937074E (zh)
RS (1)	RS49607B (zh)
SI (1)	SI0937074T1 (zh)
SK (1)	SK283269B6 (zh)
TR (1)	TR199900856T2 (zh)
WO (1)	WO1998021208A1 (zh)

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PT1075477E (pt)	1998-05-05	2003-07-31	Altana Pharma Ag	Novos n-oxidos de benzonaftiridina
JP2002523505A (ja) *	1998-08-31	2002-07-30	ビイクグルデンロンベルクヒエーミツシエフアブリークゲゼルシヤフトミツトベシユレンクテルハフツング	Ｐｄｅ３−及びｐｄｅ−４抑制作用を有するベンゾナフチリデン−ｎ−オキシド
IT1303272B1 (it)	1998-10-29	2000-11-06	Zambon Spa	Derivati triciclici inibitori della fosfodiesterasi 4
EP1163226B1 (en) *	1999-01-15	2007-03-14	ALTANA Pharma AG	Polysubstituted 6-phenylphenanthridines with pde-iv inhibiting activity
DE60024581T2 (de) *	1999-01-15	2006-08-10	Altana Pharma Ag	6-phenylphenanthridine mit pde-iv hemmender wirkung
DK1147103T3 (da)	1999-01-15	2005-08-29	Altana Pharma Ag	Phenanthridin-N-oxider med PDE-IV-inhiberende aktivitet
CA2359404A1 (en)	1999-01-15	2000-07-20	Beate Gutterer	Phenanthridine-n-oxides with pde-iv inhibiting activity
EP2193808A1 (en) *	1999-08-21	2010-06-09	Nycomed GmbH	Synergistic combination
NL1017973C2 (nl) *	2000-05-10	2002-11-08	Tristem Trading Cyprus Ltd	Inrichting.
DK1377574T3 (da) *	2001-02-21	2005-04-25	Altana Pharma Ag	6-phenylbenzonaphtyridiner
US6479493B1 (en)	2001-08-23	2002-11-12	Cell Pathways, Inc.	Methods for treatment of type I diabetes
PL373598A1 (en) *	2002-08-17	2005-09-05	Altana Pharma Ag	Novel benzonaphthyridines
US7470704B2 (en) *	2002-09-04	2008-12-30	Nycomed Gmbh	Benzonaphthyridines
ATE360021T1 (de) *	2002-09-04	2007-05-15	Altana Pharma Ag	Neue benzonaphthyridine
ES2505473T3 (es)	2004-03-03	2014-10-10	Takeda Gmbh	Nuevas hidroxi-6-heteroarilfenantridinas y su uso como inhibidores de la PDE4
AR049419A1 (es) *	2004-03-03	2006-08-02	Altana Pharma Ag	Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo
KR20060130697A (ko) *	2004-03-10	2006-12-19	알타나 파마 아게	신규한 아미도-치환 히드록시-6-페닐페난트리딘 및 ｐｄｅ4억제제로서의 이의 용도
JP2007529471A (ja) *	2004-03-17	2007-10-25	アルタナ　ファルマ　アクチエンゲゼルシャフト	新規のｎ−（アルコキシアルキル）カルバモイル置換された６−フェニル−ベンゾナフチリジン誘導体及びｐｄｅ３／４インヒビターとしてのそれらの使用
CA2579000C (en)	2004-09-08	2013-02-05	Altana Pharma Ag	Novel 3-thia-10-aza-phenanthrene derivatives
WO2006027344A2 (en) *	2004-09-08	2006-03-16	Altana Pharma Ag	3-oxa-10-aza-phenanthrenes as pde4 or pde3/4 inhibitors
US7718668B2 (en)	2005-03-02	2010-05-18	Nycomed Gmbh	Salts of 6-heterocycle substituted hexahydrophenanthridine derivatives
CA2626612A1 (en)	2005-10-19	2007-04-26	Ranbaxy Laboratories Limited	Pharmaceutical compositions of muscarinic receptor antagonists
TW200808695A (en) *	2006-06-08	2008-02-16	Amgen Inc	Benzamide derivatives and uses related thereto
MX2009002298A (es) *	2006-09-01	2009-06-04	Cylene Pharmaceuticals Inc	Moduladores de serina-treonina proteina quinasa y de parp.
MX2010011288A (es)	2008-04-23	2010-11-09	Rigel Pharmaceuticals Inc	Compuestos de carboxamida para el tratamiento de trastornos metabolicos.
AR079451A1 (es)	2009-12-18	2012-01-25	Nycomed Gmbh	Compuestos 3,4,4a,10b-tetrahidro-1h-tiopirano[4,3-c]isoquinolina
CN108299429B (zh) *	2018-04-09	2021-10-08	中南大学	一类八氢苯并萘啶化合物及其制备方法和应用

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EP0247971A3 (en) *	1986-05-29	1990-01-17	Sandoz Ag	Novel pharmaceutical compositions comprising and use of cis-6-(4-acetanilido)-8,9-dimethoxy-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridin
MY105344A (en) *	1990-05-16	1994-09-30	Byk Gulden Lomberg Chemische Fabrik	New sulphonyl compounds

1997
- 1997-11-05 EA EA199900421A patent/EA001551B1/ru not_active IP Right Cessation
- 1997-11-05 SI SI9730535T patent/SI0937074T1/xx unknown
- 1997-11-05 ID IDW990180A patent/ID22042A/id unknown
- 1997-11-05 TR TR1999/00856T patent/TR199900856T2/xx unknown
- 1997-11-05 AT AT97950093T patent/ATE234300T1/de active
- 1997-11-05 PL PL97333429A patent/PL189641B1/pl unknown
- 1997-11-05 RS YUP-194/99A patent/RS49607B/sr unknown
- 1997-11-05 KR KR10-1999-7004024A patent/KR100484045B1/ko not_active IP Right Cessation
- 1997-11-05 US US09/284,458 patent/US6008215A/en not_active Expired - Lifetime
- 1997-11-05 PT PT97950093T patent/PT937074E/pt unknown
- 1997-11-05 IL IL12905497A patent/IL129054A/en not_active IP Right Cessation
- 1997-11-05 JP JP52212098A patent/JP4223075B2/ja not_active Expired - Fee Related
- 1997-11-05 CZ CZ19991675A patent/CZ288752B6/cs not_active IP Right Cessation
- 1997-11-05 EP EP97950093A patent/EP0937074B1/en not_active Expired - Lifetime
- 1997-11-05 DE DE69719778T patent/DE69719778T2/de not_active Expired - Lifetime
- 1997-11-05 CN CN97199529A patent/CN1090188C/zh not_active Expired - Fee Related
- 1997-11-05 BR BRPI9713338-8A patent/BR9713338B1/pt not_active IP Right Cessation
- 1997-11-05 ES ES97950093T patent/ES2195189T3/es not_active Expired - Lifetime
- 1997-11-05 SK SK623-99A patent/SK283269B6/sk not_active IP Right Cessation
- 1997-11-05 WO PCT/EP1997/006096 patent/WO1998021208A1/en active IP Right Grant
- 1997-11-05 AU AU53170/98A patent/AU733129B2/en not_active Ceased
- 1997-11-05 DK DK97950093T patent/DK0937074T3/da active
- 1997-11-05 NZ NZ334976A patent/NZ334976A/xx not_active IP Right Cessation
- 1997-11-05 EE EEP199900105A patent/EE03829B1/xx not_active IP Right Cessation
- 1997-11-05 HU HU0000426A patent/HU226981B1/hu not_active IP Right Cessation
- 1997-11-05 GE GEAP19974710A patent/GEP20012390B/en unknown
- 1997-11-05 CA CA002270964A patent/CA2270964C/en not_active Expired - Fee Related
1999
- 1999-04-05 BG BG103310A patent/BG63695B1/bg unknown
- 1999-05-11 NO NO19992282A patent/NO312764B1/no not_active IP Right Cessation
2000
- 2000-02-24 HK HK00101112A patent/HK1022151A1/xx not_active IP Right Cessation
2004
- 2004-09-03 CY CY0400068A patent/CY2476B1/xx unknown

Also Published As

Publication number	Publication date
CZ288752B6 (cs)	2001-08-15
BR9713338B1 (pt)	2009-12-01
SK62399A3 (en)	1999-10-08
JP4223075B2 (ja)	2009-02-12
US6008215A (en)	1999-12-28
YU19499A (sh)	2001-09-28
NO992282D0 (no)	1999-05-11
NO992282L (no)	1999-05-11
BG103310A (en)	2000-05-31
ATE234300T1 (de)	2003-03-15
SI0937074T1 (en)	2003-08-31
DK0937074T3 (da)	2003-06-23
PT937074E (pt)	2003-07-31
SK283269B6 (sk)	2003-04-01
KR20000053100A (ko)	2000-08-25
KR100484045B1 (ko)	2005-04-20
EP0937074B1 (en)	2003-03-12
AU733129B2 (en)	2001-05-10
NZ334976A (en)	2000-10-27
CN1236367A (zh)	1999-11-24
IL129054A (en)	2002-07-25
JP2001503442A (ja)	2001-03-13
IL129054A0 (en)	2000-02-17
EA001551B1 (ru)	2001-04-23
EA199900421A1 (ru)	1999-10-28
EE9900105A (et)	1999-10-15
BR9713338A (pt)	2000-05-09
ES2195189T3 (es)	2003-12-01
CY2476B1 (en)	2005-05-03
PL189641B1 (pl)	2005-09-30
CA2270964C (en)	2007-07-31
CZ167599A3 (cs)	1999-11-17
CA2270964A1 (en)	1998-05-22
HU226981B1 (hu)	2010-04-28
AU5317098A (en)	1998-06-03
EP0937074A1 (en)	1999-08-25
TR199900856T2 (xx)	1999-07-21
DE69719778T2 (de)	2004-02-05
DE69719778D1 (de)	2003-04-17
PL333429A1 (en)	1999-12-06
HK1022151A1 (en)	2000-07-28
HUP0000426A2 (hu)	2001-02-28
EE03829B1 (et)	2002-08-15
HUP0000426A3 (en)	2001-04-28
RS49607B (sr)	2007-06-04
WO1998021208A1 (en)	1998-05-22
BG63695B1 (bg)	2002-09-30
ID22042A (id)	1999-08-26
CN1090188C (zh)	2002-09-04
GEP20012390B (en)	2001-03-25

Legal Events

Date	Code	Title	Description
2013-03-25	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: TAKEDA GMBH, DE
2015-03-09	CHAD	Change of the owner's name or address (par. 44 patent law, par. patentforskriften)	Owner name: TAKEDA GMBH, DE
2016-06-27	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO312764B1 (no)	2002-07-01	Benzonaftyridiner som bronkialterapeutika
US6306869B1 (en)	2001-10-23	N-oxides
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