IL91128A - Pharmaceuticals containing imidazo [A-2,1] isoquinolines 5-aryl or 5-troaryl are converted to prophylactic treatment for late shortening by inhalation - Google Patents

Pharmaceuticals containing imidazo [A-2,1] isoquinolines 5-aryl or 5-troaryl are converted to prophylactic treatment for late shortening by inhalation

Info

Publication number: IL91128A
Authority: IL; Israel
Prior art keywords: hydrogen; chloro; fluoro; compound; independently
Prior art date: 1988-07-29

Application number

IL9112889A

Other languages

English (en)

Hebrew (he)

Other versions

IL91128A0 (en

Original Assignee

Sandoz 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.)

1988-07-29

Filing date

1989-07-27

Publication date

1996-01-31

1989-07-27 Application filed by Sandoz Ag filed Critical Sandoz Ag

1990-03-19 Publication of IL91128A0 publication Critical patent/IL91128A0/xx

1996-01-31 Publication of IL91128A publication Critical patent/IL91128A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 14
208000006673 asthma Diseases 0.000 title claims description 11
238000011321 prophylaxis Methods 0.000 title claims description 9
BYLPZVAKOZYZPH-UHFFFAOYSA-N imidazo[2,1-a]isoquinoline Chemical class C1=CC=C2C3=NC=CN3C=CC2=C1 BYLPZVAKOZYZPH-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 65
-1 monochlorophenyl Chemical group 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000001153 fluoro group Chemical group F* 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000001309 chloro group Chemical group Cl* 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 16
125000002541 furyl group Chemical group 0.000 claims description 10
125000001544 thienyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 7
125000005936 piperidyl group Chemical group 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
206010006482 Bronchospasm Diseases 0.000 claims description 5
230000007885 bronchoconstriction Effects 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 3
239000004480 active ingredient Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000006199 nebulizer Substances 0.000 claims description 3
229940098458 powder spray Drugs 0.000 claims description 3
239000003380 propellant Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000000080 wetting agent Substances 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
238000012360 testing method Methods 0.000 description 33
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 24
239000013566 allergen Substances 0.000 description 21
IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 20
HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 18
108010003541 Platelet Activating Factor Proteins 0.000 description 17
241001465754 Metazoa Species 0.000 description 15
239000000443 aerosol Substances 0.000 description 12
108010058846 Ovalbumin Proteins 0.000 description 8
210000003979 eosinophil Anatomy 0.000 description 8
229940092253 ovalbumin Drugs 0.000 description 8
230000000694 effects Effects 0.000 description 7
OUQVKRKGTAUJQA-UHFFFAOYSA-N n-[(1-chloro-4-hydroxyisoquinolin-3-yl)carbonyl]glycine Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C21 OUQVKRKGTAUJQA-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 6
210000004027 cell Anatomy 0.000 description 5
241000700199 Cavia porcellus Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical class N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 description 4
230000002685 pulmonary effect Effects 0.000 description 4
230000009257 reactivity Effects 0.000 description 4
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
SKDFWEPBABSFMG-UHFFFAOYSA-N 1,2-dichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)CCl SKDFWEPBABSFMG-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
229940109248 cromoglycate Drugs 0.000 description 3
IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 3
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000011597 hartley guinea pig Methods 0.000 description 3
230000035874 hyperreactivity Effects 0.000 description 3
238000000034 method Methods 0.000 description 3
230000000069 prophylactic effect Effects 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
VLBPIWYTPAXCFJ-XMMPIXPASA-O Lyso-PAF C-16-d4 Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](O)COP(O)(=O)OCC[N+](C)(C)C VLBPIWYTPAXCFJ-XMMPIXPASA-O 0.000 description 2
108700020675 O-deacetyl platelet activating factor Proteins 0.000 description 2
YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000000692 Student's t-test Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000002158 endotoxin Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
150000002537 isoquinolines Chemical class 0.000 description 2
210000000265 leukocyte Anatomy 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
238000005303 weighing Methods 0.000 description 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
PQIXUJAMYUOYCA-UHFFFAOYSA-N 5-[4-[(2,3,4-trimethoxyphenyl)methoxy]phenyl]-2,3-dihydroimidazo[2,1-a]isoquinoline;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC=C1COC1=CC=C(C=2N3CCN=C3C3=CC=CC=C3C=2)C=C1 PQIXUJAMYUOYCA-UHFFFAOYSA-N 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
241000947840 Alteromonadales Species 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
206010013709 Drug ineffective Diseases 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
206010014950 Eosinophilia Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000004852 Lung Injury Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
206010069363 Traumatic lung injury Diseases 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
238000001949 anaesthesia Methods 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000000427 antigen Substances 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
229940098773 bovine serum albumin Drugs 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
229960003957 dexamethasone Drugs 0.000 description 1
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 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000003304 gavage Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
YNVAJQXKPOSSPH-UHFFFAOYSA-N imidazo[2,1-a]isoquinoline hydrochloride Chemical compound Cl.N=1C=CN2C1C1=CC=CC=C1C=C2 YNVAJQXKPOSSPH-UHFFFAOYSA-N 0.000 description 1
238000002513 implantation Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
231100000824 inhalation exposure Toxicity 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
GACFTYIPBQCTQB-UHFFFAOYSA-N isoquinoline;dihydrochloride Chemical compound Cl.Cl.C1=NC=CC2=CC=CC=C21 GACFTYIPBQCTQB-UHFFFAOYSA-N 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
231100000515 lung injury Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
229960004618 prednisone Drugs 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
201000009732 pulmonary eosinophilia Diseases 0.000 description 1
230000007115 recruitment Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
238000012353 t test Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000011282 treatment Methods 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

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

IL9112889A 1988-07-29 1989-07-27 Pharmaceuticals containing imidazo [A-2,1] isoquinolines 5-aryl or 5-troaryl are converted to prophylactic treatment for late shortening by inhalation IL91128A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US22630588A	1988-07-29	1988-07-29
US07/302,720 US4910206A (en)	1986-07-14	1989-01-27	5-hetero-or aryl-substituted-imidazo(2,1-a)isoquinolines and their use as PAF receptor antagonists

Publications (2)

Publication Number	Publication Date
IL91128A0 IL91128A0 (en)	1990-03-19
IL91128A true IL91128A (en)	1996-01-31

Family

ID=26920416

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9112889A IL91128A (en)	1988-07-29	1989-07-27	Pharmaceuticals containing imidazo [A-2,1] isoquinolines 5-aryl or 5-troaryl are converted to prophylactic treatment for late shortening by inhalation

Country Status (16)

Country	Link
US (1)	US4910206A (no)
EP (1)	EP0357550B1 (no)
JP (1)	JPH0273016A (no)
KR (1)	KR910002445A (no)
AU (1)	AU632487B2 (no)
CA (1)	CA1336503C (no)
DE (1)	DE68913397T2 (no)
DK (1)	DK372089A (no)
ES (1)	ES2062092T3 (no)
FI (1)	FI893616A (no)
HU (1)	HU206040B (no)
IE (1)	IE63243B1 (no)
IL (1)	IL91128A (no)
NO (1)	NO177485C (no)
NZ (1)	NZ230098A (no)
PT (1)	PT91302B (no)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1989010143A1 (en) *	1988-04-27	1989-11-02	Schering Corporation	Certain paf antagonist antihistamine combinations and methods
US5639782A (en) *	1992-03-04	1997-06-17	Center For Innovative Technology	Neolignan derivatives as platelet activating factor receptor antagonists and 5-lipoxygenase inhibitors
US5530141A (en) *	1992-03-04	1996-06-25	Center For Innovative Technology	2,4-diaryl-1,3-dithiolanes; 2,4-diaryl-1,3-dioxolanes; 2,4-diaryl-1,3-oxathiolanes; and 2,5-diaryl-1,3-oxathiolanes for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5358938A (en) *	1992-07-13	1994-10-25	Cytomed, Inc.	Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
EP0650485B1 (en)	1992-07-13	2000-10-11	Cytomed, Inc.	2,5-diaryl tetrahydro-thiophenes, -furans and analogs for the treatment of inflammatory and immune disorders
US5434151A (en) *	1992-08-24	1995-07-18	Cytomed, Inc.	Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5463083A (en) *	1992-07-13	1995-10-31	Cytomed, Inc.	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5648486A (en) *	1992-07-13	1997-07-15	Cytomed, Inc.	Compounds and methods for the treatment of inflammatory and immune disorders
US5703093A (en) *	1995-05-31	1997-12-30	Cytomed, Inc.	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5792776A (en) *	1994-06-27	1998-08-11	Cytomed, Inc.,	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5750565A (en) *	1995-05-25	1998-05-12	Cytomed, Inc.	Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
FR2756560A1 (fr) *	1996-12-04	1998-06-05	Adir	Nouveaux derives de l'imidazoline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CN1076728C (zh) *	1999-02-05	2001-12-26	浙江大学	2－芳基咪唑并[2,1－a]异喹啉的衍生物及其用途
CN112574176B (zh) *	2019-09-27	2024-03-15	隆泰申医药科技(南京)有限公司	一种杂芳基类化合物及其应用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4101553A (en) *	1974-01-02	1978-07-18	Sandoz, Inc.	Imidazo[2,1-a]isoquinolines
HU172649B (hu) *	1975-04-24	1978-11-28	Gyogyszerkutato Intezet	Sposob poluchenija novykh biologicheski aktivnykh lizergamidov
DE3777919D1 (de) *	1986-07-14	1992-05-07	Sandoz Ag	5-hetero- oder -aryl-substituierte imidazo(2,1-a)isochinoline.

1989
- 1989-01-27 US US07/302,720 patent/US4910206A/en not_active Expired - Fee Related
- 1989-07-18 HU HU893613A patent/HU206040B/hu not_active IP Right Cessation
- 1989-07-25 ES ES89810565T patent/ES2062092T3/es not_active Expired - Lifetime
- 1989-07-25 EP EP89810565A patent/EP0357550B1/en not_active Expired - Lifetime
- 1989-07-25 DE DE68913397T patent/DE68913397T2/de not_active Expired - Fee Related
- 1989-07-27 NO NO893062A patent/NO177485C/no unknown
- 1989-07-27 PT PT91302A patent/PT91302B/pt not_active IP Right Cessation
- 1989-07-27 DK DK372089A patent/DK372089A/da not_active Application Discontinuation
- 1989-07-27 NZ NZ230098A patent/NZ230098A/en unknown
- 1989-07-27 IL IL9112889A patent/IL91128A/en not_active IP Right Cessation
- 1989-07-27 AU AU39017/89A patent/AU632487B2/en not_active Ceased
- 1989-07-28 CA CA000606986A patent/CA1336503C/en not_active Expired - Fee Related
- 1989-07-28 IE IE245989A patent/IE63243B1/en not_active IP Right Cessation
- 1989-07-28 JP JP1194436A patent/JPH0273016A/ja active Pending
- 1989-07-28 KR KR1019890010692A patent/KR910002445A/ko not_active Application Discontinuation
- 1989-07-28 FI FI893616A patent/FI893616A/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
ES2062092T3 (es)	1994-12-16
IL91128A0 (en)	1990-03-19
FI893616A (fi)	1990-01-30
NZ230098A (en)	1992-02-25
PT91302B (pt)	1995-03-01
AU3901789A (en)	1990-02-01
IE63243B1 (en)	1995-04-05
NO177485C (no)	1995-09-27
HU206040B (en)	1992-08-28
AU632487B2 (en)	1993-01-07
KR910002445A (ko)	1991-02-25
PT91302A (pt)	1990-02-08
DE68913397D1 (de)	1994-04-07
DE68913397T2 (de)	1994-08-11
EP0357550B1 (en)	1994-03-02
JPH0273016A (ja)	1990-03-13
HUT50630A (en)	1990-03-28
US4910206A (en)	1990-03-20
EP0357550A2 (en)	1990-03-07
NO893062D0 (no)	1989-07-27
NO177485B (no)	1995-06-19
EP0357550A3 (en)	1991-04-03
DK372089D0 (da)	1989-07-27
CA1336503C (en)	1995-08-01
FI893616A0 (fi)	1989-07-28
DK372089A (da)	1990-01-30
NO893062L (no)	1990-01-30
IE892459L (en)	1990-01-29

Legal Events

Date	Code	Title
1996-07-23	FF	Patent granted
1996-10-16	KB	Patent renewed
1997-11-20	HC	Change of name of proprietor(s)
2000-07-16	RH	Patent void

Publication	Publication Date	Title
IL91128A (en)	1996-01-31	Pharmaceuticals containing imidazo [A-2,1] isoquinolines 5-aryl or 5-troaryl are converted to prophylactic treatment for late shortening by inhalation
CA2268957C (en)	2008-04-29	Immune response modifier compounds for treatment of th2 mediated and related diseases
EP1550662B1 (en)	2012-07-04	Adenine compound and use thereof
EP1389094B1 (en)	2008-09-03	Delivery of sedative-hypnotics trough an inhalation route
AU775588B2 (en)	2004-08-05	Novel medicament compositions, based on anticholinergically effective compounds and beta-mimetics
Djerassi et al.	1976	Methotrexate and citrovorum factor rescue in the management of childhood lymphosarcoma and reticulum cell sarcoma (non‐Hodgkin's lymphomas). Prolonged Unmaintained Remissions
JP2006515829A (ja)	2006-06-08	炎症性疾病の処置のための、ａ２ａアデノシン受容体アゴニストの使用
JP2007536241A (ja)	2007-12-13	糖尿病性腎症の処置のためのａ２ａアデノシンレセプターアゴニスト
JPH02501929A (ja)	1990-06-28	医学的使用
JPH04506215A (ja)	1992-10-29	モノカイン活性干渉
EA001929B1 (ru)	2001-10-22	Способ лечения заболеваний млекопитающих и цвиттерионная композиция
CA2029704C (en)	1995-02-07	Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders
OA12660A (en)	2006-06-19	Inhalation compositions comprising tricyclic 5,6-dihydro-9H-pyrazolo(3,4-C)-1,2,4-triazolo (4,3-aopha)pyridines.
US5599817A (en)	1997-02-04	Xanthine derivatives as diuretic agents
JP4783787B2 (ja)	2011-09-28	炎症疾患を処置するためのニコチン受容体アゴニスト
CN111032041A (zh)	2020-04-17	治疗类风湿关节炎的组合物和方法
EP0258175B1 (en)	1992-04-01	5-hetero- or aryl-substituted-imidazo[2,1-a]isoquinolines
US4639445A (en)	1987-01-27	Metabolites of triazolo[1,5-c]pyrimidines
US3743733A (en)	1973-07-03	Method of treating bronchial asthma
FI85481B (fi)	1992-01-15	Foerfarande foer framstaellning av 2,3 -dihydro-1-(8-metyl-1,2,4-triazolo/4,3-b/pyridazin-6-yl)-4(1h) -pyridinon.
US20080004296A1 (en)	2008-01-03	Organic Compounds
AU637542B2 (en)	1993-05-27	Method of inhibiting activity of leukocyte derived cytokines
CA2161980A1 (en)	1994-11-10	Substituted methylenedioxy¬3',4':6,7\|indolizino-¬1,2-b\|quinolinones
JPH0459776A (ja)	1992-02-26	フェノキシプロピルアミン誘導体およびこれを含有する抗潰瘍剤
JPH04128220A (ja)	1992-04-28	抗ヘルペスウイルス剤