PH27084A - Agents for the treatment of acute and chronic obstructive respiratory passage diseases - Google Patents

Agents for the treatment of acute and chronic obstructive respiratory passage diseases Download PDF

Info

Publication number: PH27084A
Authority: PH; Philippines
Prior art keywords: compound; dibenz; dihydro; methyl; azepin
Prior art date: 1988-11-17

Application number

PH39548A

Other languages

English (en)

Inventor

Wolfgang Dr Eberlein

Wolfhard Dr Engel

Gerhard Dr Mihm

Klaus Dr Rudolf

Norbert Dr Mayer

Henri Dr Doods

Original Assignee

Thomae Gmbh Dr K

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.)

1988-11-17

Filing date

1989-11-17

Publication date

1993-02-19

1989-11-17 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1993-02-19 Publication of PH27084A publication Critical patent/PH27084A/en

Links

230000000241 respiratory effect Effects 0.000 title claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 11
230000000414 obstructive effect Effects 0.000 title claims description 9
230000001154 acute effect Effects 0.000 title description 5
230000001684 chronic effect Effects 0.000 title description 5
201000010099 disease Diseases 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 21
-1 1-methyl-4- piperidinyl Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
229940126062 Compound A Drugs 0.000 claims description 6
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
206010006458 Bronchitis chronic Diseases 0.000 claims description 4
206010014561 Emphysema Diseases 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
206010006451 bronchitis Diseases 0.000 claims description 4
208000007451 chronic bronchitis Diseases 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 15
230000000694 effects Effects 0.000 description 14
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 11
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
239000000126 substance Substances 0.000 description 10
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 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
239000000829 suppository Substances 0.000 description 7
229930003347 Atropine Natural products 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
229960000396 atropine Drugs 0.000 description 6
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
210000000056 organ Anatomy 0.000 description 6
ALOCUZOKRULSAA-UHFFFAOYSA-N 1-methylpiperidin-4-amine Chemical compound CN1CCC(N)CC1 ALOCUZOKRULSAA-UHFFFAOYSA-N 0.000 description 5
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
229960004373 acetylcholine Drugs 0.000 description 5
230000027455 binding Effects 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 4
206010006482 Bronchospasm Diseases 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
210000000621 bronchi Anatomy 0.000 description 4
230000007885 bronchoconstriction Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
238000000926 separation method Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000001022 anti-muscarinic effect Effects 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000011534 incubation Methods 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
239000003149 muscarinic antagonist Substances 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
235000005985 organic acids Nutrition 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
235000001258 Cinchona calisaya Nutrition 0.000 description 2
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
240000004760 Pimpinella anisum Species 0.000 description 2
235000012550 Pimpinella anisum Nutrition 0.000 description 2
230000001078 anti-cholinergic effect Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
210000003710 cerebral cortex Anatomy 0.000 description 2
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
230000008602 contraction Effects 0.000 description 2
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
230000000574 ganglionic effect Effects 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229940041616 menthol Drugs 0.000 description 2
210000002569 neuron Anatomy 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000003380 propellant Substances 0.000 description 2
229960000948 quinine Drugs 0.000 description 2
239000002287 radioligand Substances 0.000 description 2
239000002002 slurry Substances 0.000 description 2
229960001462 sodium cyclamate Drugs 0.000 description 2
230000009870 specific binding Effects 0.000 description 2
UIKHKLFBHLPAPO-UHFFFAOYSA-N 2,3-diacetyl-2,3-dihydroxybutanedioic acid Chemical compound CC(=O)C(O)(C(O)=O)C(O)(C(C)=O)C(O)=O UIKHKLFBHLPAPO-UHFFFAOYSA-N 0.000 description 1
GBJFSZCDZHSAOP-UHFFFAOYSA-N 2,3-dihydroxy-4-methoxy-4-oxobutanoic acid Chemical compound COC(=O)C(O)C(O)C(O)=O GBJFSZCDZHSAOP-UHFFFAOYSA-N 0.000 description 1
150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 1
208000000884 Airway Obstruction Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
206010010774 Constipation Diseases 0.000 description 1
208000012895 Gastric disease Diseases 0.000 description 1
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
208000006550 Mydriasis Diseases 0.000 description 1
206010039424 Salivary hypersecretion Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
239000003708 ampul Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
SFZBBUSDVJSDGR-XWFYHZIMSA-N beta-D-Galp-(1->4)-[alpha-L-Fucp-(1->3)]-beta-D-GlcpNAc-(1->3)-beta-D-Galp Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O[C@@H](O[C@H]2[C@H]([C@@H](CO)O[C@@H](O)[C@@H]2O)O)[C@@H]1NC(C)=O SFZBBUSDVJSDGR-XWFYHZIMSA-N 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000001813 broncholytic effect Effects 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
210000004720 cerebrum Anatomy 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
238000009795 derivation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000011990 functional testing Methods 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
229960001383 methylscopolamine Drugs 0.000 description 1
230000003551 muscarinic effect Effects 0.000 description 1
YHPZJPHWYNWYAZ-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-6-oxo-5,11-dihydrobenzo[c][1]benzazepine-11-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1C2=CC=CC=C2C(=O)NC2=CC=CC=C21 YHPZJPHWYNWYAZ-UHFFFAOYSA-N 0.000 description 1
AUZJUQLPAGNLMM-UHFFFAOYSA-N n-(1-methylpiperidin-4-yl)-6-oxo-5,11-dihydrobenzo[c][1]benzazepine-11-carboxamide;hydrochloride Chemical compound Cl.C1CN(C)CCC1NC(=O)C1C2=CC=CC=C2C(=O)NC2=CC=CC=C21 AUZJUQLPAGNLMM-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
210000000192 parasympathetic ganglia Anatomy 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229960004633 pirenzepine Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000009153 reflex inhibition Effects 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000009121 systemic therapy Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- 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

Landscapes

Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

PH39548A 1988-11-17 1989-11-17 Agents for the treatment of acute and chronic obstructive respiratory passage diseases PH27084A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3838912A DE3838912A1 (de)	1988-11-17	1988-11-17	Mittel zur behandlung von akuten und chronischen obstruktiven atemwegserkrankungen

Publications (1)

Publication Number	Publication Date
PH27084A true PH27084A (en)	1993-02-19

Family

ID=6367356

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH39548A PH27084A (en)	1988-11-17	1989-11-17	Agents for the treatment of acute and chronic obstructive respiratory passage diseases

Country Status (13)

Country	Link
US (1)	US5011836A (hu)
EP (1)	EP0369286A3 (hu)
JP (1)	JPH02180829A (hu)
KR (1)	KR900007421A (hu)
AU (1)	AU618422B2 (hu)
CA (1)	CA2002980A1 (hu)
DE (1)	DE3838912A1 (hu)
DK (1)	DK574289A (hu)
HU (1)	HU203283B (hu)
IL (1)	IL92314A0 (hu)
NZ (1)	NZ231403A (hu)
PH (1)	PH27084A (hu)
ZA (1)	ZA898741B (hu)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1049700B9 (en)	1998-01-21	2006-05-10	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
US6509346B2 (en)	1998-01-21	2003-01-21	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
JP2002501052A (ja) *	1998-01-21	2002-01-15	ミレニアム・ファーマシューティカルズ・インコーポレイテッド	ケモカイン受容体アンタゴニストおよびその使用方法
US6613905B1 (en)	1998-01-21	2003-09-02	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
US7271176B2 (en) *	1998-09-04	2007-09-18	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use thereof
US7541365B2 (en)	2001-11-21	2009-06-02	Millennium Pharmaceuticals, Inc.	Chemokine receptor antagonists and methods of use therefor
TWI291467B (en)	2002-11-13	2007-12-21	Millennium Pharm Inc	CCR1 antagonists and methods of use therefor
KR100863492B1 (ko) *	2007-06-05	2008-10-14	주식회사 오에스티	플라즈마 디스플레이 패널의 형광체 세정 방법 및 그 장치

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3204157A1 (de) *	1982-02-06	1983-08-11	Dr. Karl Thomae Gmbh, 7950 Biberach	Substituierte dibenzodiazepinone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE3402060A1 (de) *	1984-01-21	1985-08-01	Dr. Karl Thomae Gmbh, 7950 Biberach	Substituierte 5,11-dihydro-6h-dibenz(b,e)azepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1988
- 1988-11-17 DE DE3838912A patent/DE3838912A1/de not_active Withdrawn
1989
- 1989-11-07 EP EP19890120553 patent/EP0369286A3/de not_active Ceased
- 1989-11-15 IL IL92314A patent/IL92314A0/xx unknown
- 1989-11-15 CA CA002002980A patent/CA2002980A1/en not_active Abandoned
- 1989-11-15 NZ NZ231403A patent/NZ231403A/en unknown
- 1989-11-16 DK DK574289A patent/DK574289A/da not_active Application Discontinuation
- 1989-11-16 ZA ZA898741A patent/ZA898741B/xx unknown
- 1989-11-16 HU HU895932A patent/HU203283B/hu not_active IP Right Cessation
- 1989-11-16 KR KR1019890016583A patent/KR900007421A/ko not_active Application Discontinuation
- 1989-11-16 JP JP1298727A patent/JPH02180829A/ja active Pending
- 1989-11-17 AU AU44760/89A patent/AU618422B2/en not_active Ceased
- 1989-11-17 US US07/438,827 patent/US5011836A/en not_active Expired - Fee Related
- 1989-11-17 PH PH39548A patent/PH27084A/en unknown

Also Published As

Publication number	Publication date
AU4476089A (en)	1990-05-24
AU618422B2 (en)	1991-12-19
EP0369286A3 (de)	1992-01-02
US5011836A (en)	1991-04-30
DE3838912A1 (de)	1990-05-23
EP0369286A2 (de)	1990-05-23
KR900007421A (ko)	1990-06-01
HU895932D0 (en)	1990-02-28
JPH02180829A (ja)	1990-07-13
IL92314A0 (en)	1990-07-26
CA2002980A1 (en)	1990-05-17
DK574289D0 (da)	1989-11-16
NZ231403A (en)	1992-06-25
DK574289A (da)	1990-05-18
HUT51898A (en)	1990-06-28
ZA898741B (en)	1991-07-31
HU203283B (en)	1991-07-29

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