SE501548C2 - Isokinolinderivat, deras framställning och deras användning - Google Patents

Isokinolinderivat, deras framställning och deras användning

Info

Publication number: SE501548C2
Authority: SE; Sweden
Prior art keywords: dimethoxy; formula; hydrogen; dimethoxyphenyl; compound
Prior art date: 1988-01-08

Application number

SE8900039A

Other languages

English (en)

Swedish (sv)

Other versions

SE8900039L (sv

SE8900039D0 (sv

Inventor

Klaus Hasspacher

Reto Naef

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.)

1988-01-08

Filing date

1989-01-05

Publication date

1995-03-13

1989-01-05 Application filed by Sandoz Ag filed Critical Sandoz Ag

1989-01-05 Publication of SE8900039D0 publication Critical patent/SE8900039D0/xx

1989-07-09 Publication of SE8900039L publication Critical patent/SE8900039L/xx

1995-03-13 Publication of SE501548C2 publication Critical patent/SE501548C2/sv

Links

238000002360 preparation method Methods 0.000 title claims description 4
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 67
150000003839 salts Chemical group 0.000 claims abstract description 40
239000001257 hydrogen Substances 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
150000002431 hydrogen Chemical group 0.000 claims abstract description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract 2
239000002253 acid Substances 0.000 claims description 36
238000000034 method Methods 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
-1 3,5-dimethoxyphenyl Chemical group 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
DMHHZHNQPPVBBI-UHFFFAOYSA-N 1-(2-ethoxy-3,5-dimethoxyphenyl)-6,7-dimethoxy-3-methyl-3,4-dihydroisoquinoline Chemical compound CCOC1=C(OC)C=C(OC)C=C1C1=NC(C)CC2=CC(OC)=C(OC)C=C12 DMHHZHNQPPVBBI-UHFFFAOYSA-N 0.000 claims 1
FVERZONBNNHMAO-UHFFFAOYSA-N 1-(2-ethoxy-3,5-dimethoxyphenyl)-6,7-dimethoxy-3-methylisoquinoline Chemical group CCOC1=C(OC)C=C(OC)C=C1C1=NC(C)=CC2=CC(OC)=C(OC)C=C12 FVERZONBNNHMAO-UHFFFAOYSA-N 0.000 claims 1
UVAVGOKRURKQSB-UHFFFAOYSA-N 1-(2-ethoxy-3,5-dimethoxyphenyl)-6,7-dimethoxy-3-phenyl-3,4-dihydroisoquinoline Chemical compound C1(=CC=CC=C1)C1N=C(C2=CC(=C(C=C2C1)OC)OC)C1=C(C(=CC(=C1)OC)OC)OCC UVAVGOKRURKQSB-UHFFFAOYSA-N 0.000 claims 1
VHHPXPHITCJXED-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-3-ethyl-6,7-dimethoxy-3,4-dihydroisoquinoline Chemical compound N=1C(CC)CC2=CC(OC)=C(OC)C=C2C=1C1=CC(OC)=CC(OC)=C1 VHHPXPHITCJXED-UHFFFAOYSA-N 0.000 claims 1
QEXKYNTWXSVACK-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-diethoxy-3,4-dihydroisoquinoline Chemical compound C1=2C=C(OCC)C(OCC)=CC=2CCN=C1C1=CC(OC)=CC(OC)=C1 QEXKYNTWXSVACK-UHFFFAOYSA-N 0.000 claims 1
LYFJDACQGCQHHS-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-1,4-dimethyl-2H-isoquinoline Chemical compound COC1=CC(OC)=CC(C2(C)C3=CC(OC)=C(OC)C=C3C(C)=CN2)=C1 LYFJDACQGCQHHS-UHFFFAOYSA-N 0.000 claims 1
LKLNENIIYYSTSC-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-3,3-dimethyl-4h-isoquinoline Chemical compound COC1=CC(OC)=CC(C=2C3=CC(OC)=C(OC)C=C3CC(C)(C)N=2)=C1 LKLNENIIYYSTSC-UHFFFAOYSA-N 0.000 claims 1
FDUVRUPJHXWBFK-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-3,4-dihydroisoquinoline Chemical compound COC1=CC(OC)=CC(C=2C3=CC(OC)=C(OC)C=C3CCN=2)=C1 FDUVRUPJHXWBFK-UHFFFAOYSA-N 0.000 claims 1
MKYSAGPSWGOWQV-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-3-methyl-3,4-dihydroisoquinoline Chemical compound COC1=CC(OC)=CC(C=2C3=CC(OC)=C(OC)C=C3CC(C)N=2)=C1 MKYSAGPSWGOWQV-UHFFFAOYSA-N 0.000 claims 1
ZJRBDWFZHXJBFT-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-3-propyl-3,4-dihydroisoquinoline Chemical compound N=1C(CCC)CC2=CC(OC)=C(OC)C=C2C=1C1=CC(OC)=CC(OC)=C1 ZJRBDWFZHXJBFT-UHFFFAOYSA-N 0.000 claims 1
BRQANDYUFPUOAF-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-3-propylisoquinoline Chemical compound N=1C(CCC)=CC2=CC(OC)=C(OC)C=C2C=1C1=CC(OC)=CC(OC)=C1 BRQANDYUFPUOAF-UHFFFAOYSA-N 0.000 claims 1
UBTQKODDMYHWPC-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxy-4-methyl-3,4-dihydroisoquinoline Chemical compound COC1=CC(OC)=CC(C=2C3=CC(OC)=C(OC)C=C3C(C)CN=2)=C1 UBTQKODDMYHWPC-UHFFFAOYSA-N 0.000 claims 1
FVMIFRSMXXZSPL-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-6,7-dimethoxyisoquinoline Chemical compound COC1=CC(OC)=CC(C=2C3=CC(OC)=C(OC)C=C3C=CN=2)=C1 FVMIFRSMXXZSPL-UHFFFAOYSA-N 0.000 claims 1
WQMSCXCVYMIQHO-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-7-methoxy-3,4-dihydroisoquinolin-6-ol Chemical compound COC1=CC(OC)=CC(C=2C3=CC(OC)=C(O)C=C3CCN=2)=C1 WQMSCXCVYMIQHO-UHFFFAOYSA-N 0.000 claims 1
USKARTOPESBXKX-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)-7-methoxy-6-(2-methoxyethoxy)-3,4-dihydroisoquinoline Chemical compound C1=2C=C(OC)C(OCCOC)=CC=2CCN=C1C1=CC(OC)=CC(OC)=C1 USKARTOPESBXKX-UHFFFAOYSA-N 0.000 claims 1
QJQBMBQVKZQWME-UHFFFAOYSA-N 1-(3,5-dimethoxyphenyl)isoquinoline Chemical compound COC1=CC(OC)=CC(C=2C3=CC=CC=C3C=CN=2)=C1 QJQBMBQVKZQWME-UHFFFAOYSA-N 0.000 claims 1
FHYUNOHOHGWZEY-UHFFFAOYSA-N 1-(4-bromo-2-ethoxy-3,5-dimethoxyphenyl)-6,7-dimethoxy-3-methyl-3,4-dihydroisoquinoline Chemical group CCOC1=C(OC)C(Br)=C(OC)C=C1C1=NC(C)CC2=CC(OC)=C(OC)C=C12 FHYUNOHOHGWZEY-UHFFFAOYSA-N 0.000 claims 1
UFPQCQCZPCMEIA-UHFFFAOYSA-N 1-[4-bromo-3,5-bis(2-methoxyethoxy)phenyl]-6,7-dimethoxy-3-methylisoquinoline Chemical compound COCCOC1=C(Br)C(OCCOC)=CC(C=2C3=CC(OC)=C(OC)C=C3C=C(C)N=2)=C1 UFPQCQCZPCMEIA-UHFFFAOYSA-N 0.000 claims 1
ADSOCUHDKZIXRJ-UHFFFAOYSA-N 2-[1-[3,5-bis(2-methoxyethoxy)phenyl]-7-methoxy-3-methylisoquinolin-6-yl]oxyethanol Chemical compound COCCOC1=CC(OCCOC)=CC(C=2C3=CC(OC)=C(OCCO)C=C3C=C(C)N=2)=C1 ADSOCUHDKZIXRJ-UHFFFAOYSA-N 0.000 claims 1
125000004438 haloalkoxy group Chemical group 0.000 claims 1
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
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230000000414 obstructive effect Effects 0.000 abstract description 8
238000009825 accumulation Methods 0.000 abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 4
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229910052736 halogen Chemical group 0.000 abstract description 3
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125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
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WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
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208000003401 eosinophilic granuloma Diseases 0.000 description 1
201000009580 eosinophilic pneumonia Diseases 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
208000024711 extrinsic asthma Diseases 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
ICLWTJIMXVISSR-UHFFFAOYSA-N gallamine Chemical compound CCN(CC)CCOC1=CC=CC(OCCN(CC)CC)=C1OCCN(CC)CC ICLWTJIMXVISSR-UHFFFAOYSA-N 0.000 description 1
229960003054 gallamine Drugs 0.000 description 1
238000002309 gasification Methods 0.000 description 1
201000005298 gastrointestinal allergy Diseases 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000007686 hepatotoxicity Effects 0.000 description 1
231100000304 hepatotoxicity Toxicity 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
206010020718 hyperplasia Diseases 0.000 description 1
230000002390 hyperplastic effect Effects 0.000 description 1
206010021198 ichthyosis Diseases 0.000 description 1
208000013397 idiopathic acute eosinophilic pneumonia Diseases 0.000 description 1
201000007156 immunoglobulin alpha deficiency Diseases 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
201000006334 interstitial nephritis Diseases 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
238000000464 low-speed centrifugation Methods 0.000 description 1
230000004199 lung function Effects 0.000 description 1
201000006512 mast cell neoplasm Diseases 0.000 description 1
208000006971 mastocytoma Diseases 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002483 medication Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
208000007892 occupational asthma Diseases 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000003071 parasitic effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
229960002695 phenobarbital Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
201000006292 polyarteritis nodosa Diseases 0.000 description 1
238000009117 preventive therapy Methods 0.000 description 1
208000037920 primary disease Diseases 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
230000007017 scission Effects 0.000 description 1
208000029138 selective IgA deficiency disease Diseases 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
208000004003 siderosis Diseases 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
239000003506 spasmogen Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000013517 stratification Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000002992 thymic effect Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000009423 ventilation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

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

SE8900039A 1988-01-08 1989-01-05 Isokinolinderivat, deras framställning och deras användning SE501548C2 (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888800397A GB8800397D0 (en)	1988-01-08	1988-01-08	Improvements in/relating to organic compounds

Publications (3)

Publication Number	Publication Date
SE8900039D0 SE8900039D0 (sv)	1989-01-05
SE8900039L SE8900039L (sv)	1989-07-09
SE501548C2 true SE501548C2 (sv)	1995-03-13

Family

ID=10629678

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8900039A SE501548C2 (sv)	1988-01-08	1989-01-05	Isokinolinderivat, deras framställning och deras användning

Country Status (28)

Country	Link
US (1)	US4980359A (de)
JP (1)	JPH0649686B2 (de)
KR (1)	KR0142686B1 (de)
AT (1)	AT394365B (de)
AU (1)	AU622429B2 (de)
BE (1)	BE1002730A3 (de)
CA (1)	CA1332944C (de)
CH (1)	CH678727A5 (de)
DE (1)	DE3900233C2 (de)
DK (1)	DK5789A (de)
ES (1)	ES2010071A6 (de)
FI (1)	FI90865C (de)
FR (1)	FR2625743B1 (de)
GB (2)	GB8800397D0 (de)
GR (1)	GR1002750B (de)
HU (1)	HU205083B (de)
IE (1)	IE61914B1 (de)
IL (1)	IL88899A (de)
IT (1)	IT1229523B (de)
LU (1)	LU87423A1 (de)
MY (1)	MY103963A (de)
NL (1)	NL8900029A (de)
NZ (1)	NZ227561A (de)
PH (1)	PH25640A (de)
PL (1)	PL156099B1 (de)
PT (1)	PT89405B (de)
SE (1)	SE501548C2 (de)
ZA (1)	ZA89133B (de)

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US2723674A (en) *	1951-11-28	1955-11-15	Charles E Harris	Telephone cableman's tent
US3007541A (en) *	1959-02-24	1961-11-07	Jr John B Mast	Temporary covering and support structure therefor
GB8807922D0 (en) *	1988-04-05	1988-05-05	Fujisawa Pharmaceutical Co	Isoquinoline compound & process for preparation thereof
US4956371A (en) *	1989-09-19	1990-09-11	Euroceltique, S.A.	Substituted isoquinolines and methods of using same
GB8921304D0 (en) *	1989-09-20	1989-11-08	Wyeth John & Brother Ltd	New method of treatment and heterocyclic compounds used therein
GB9027055D0 (en) *	1990-12-13	1991-02-06	Sandoz Ltd	Organic compounds
KR930703259A (ko) *	1990-12-17	1993-11-29	알베르투스 빌헬무스 요아네스 쩨스트라텐	살균성 이소퀴놀린 유도체
CA2093577C (en) *	1992-05-07	2006-01-03	Michael Klaus	Alkyl or alkoxy substituted s-heterocyclic retinoids
US5350423A (en) *	1992-09-23	1994-09-27	Burlington Industries Inc.	Fabric finishing procedure
GB9322828D0 (en) *	1993-11-05	1993-12-22	Sandoz Ltd	Organic compounds
US5783184A (en) *	1994-12-23	1998-07-21	Smithkline Beecham Corporation	Method for treatment and diagnosis of IL-5 mediated disorders
JP2001523083A (ja) *	1994-12-23	2001-11-20	スミスクライン・ビーチャム・コーポレイション	Ｉｌ−５により媒介される疾病の治療に有用な組み換えｉｌ−５アンタゴニスト
US7399837B2 (en) *	1995-12-22	2008-07-15	Smithkline Beecham Corporation	Recombinant IL-5 antagonists useful in treatment of IL-5 mediated disorders
US5683892A (en) *	1994-12-23	1997-11-04	Smithkline Beecham Corporation	DNA encoding recombinant IL-5 antagonists useful in treatment of IL-5 mediated disorders
GB9622386D0 (en) *	1996-10-28	1997-01-08	Sandoz Ltd	Organic compounds
RU2174123C2 (ru) *	1996-10-28	2001-09-27	Новартис Аг	Производные 8-арил-1,7-нафтиридина и фармацевтическая композиция, обладающая противовоспалительной активностью
IT1296985B1 (it) *	1997-12-19	1999-08-03	Zambon Spa	Derivati benzazinici inibitori della fosfodiesterasi 4
ATE356810T1 (de) *	1999-01-15	2007-04-15	Altana Pharma Ag	Polysubstituted 6-phenylphenanthridines mit pde- iv hemmender wirkung
PL200923B1 (pl)	1999-08-21	2009-02-27	Nycomed Gmbh	Lek zawierający inhibitor PDE w połączeniu z agonistą receptoraß₂ -adrenergicznego oraz zastosowanie połączenia roflumilastu i salmeterolu
RU2213735C2 (ru) *	2001-09-24	2003-10-10	ГУ Институт технической химии Уральского отделения РАН	Способ получения 1-замещенных 3,3-диметил-3,4-дигидроизохинолинов
AR037517A1 (es) *	2001-11-05	2004-11-17	Novartis Ag	Derivados de naftiridinas, un proceso para su preparacion, composicion farmaceutica y el uso de los mismos para la preparacion de un medicamento para el tratamiento de una enfermedad inflamatoria
JP2006522151A (ja)	2003-04-01	2006-09-28	アプライドリサーチシステムズエーアールエスホールディングナームロゼフェンノートシャップ	不妊症におけるホスホジエステラーゼ阻害剤
WO2008134724A2 (en) *	2007-04-30	2008-11-06	Smithkline Beecham Corporation	Methods for administering anti-il-5 antibodies
KR20100134702A (ko)	2008-03-28	2010-12-23	글락소스미스클라인 엘엘씨	치료 방법
AU2009303389B2 (en)	2008-10-17	2014-10-16	Wisconsin Alumni Research Foundation	Method of making biologically active alpha-beta peptides
CN110913887A (zh)	2017-06-06	2020-03-24	葛兰素史克有限责任公司	用于儿科患者的生物药物组合物和方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB645139A (en) *	1946-10-22	1950-10-25	Servita Gyogyszeryar Es Vegyip	Improved process for the production of isoquinoline derivatives
DE1184344B (de) *	1962-06-16	1964-12-31	Orgamol Sa	Verfahren zur Herstellung von Isochinolinderivaten
US3878215A (en) *	1971-12-01	1975-04-15	Sandoz Ag	2-Alkyl-3-substituted-4-aryl isoquinolines
DE2401453A1 (de) *	1973-01-16	1974-07-18	John James Voorhees	Pharmazeutische zusammensetzung zur behandlung von hautproliferationserkrankungen
US4018927A (en) *	1973-12-17	1977-04-19	The Regents Of The University Of Michigan	Treatment of proliferating skin diseases with papaverine alkaloids
FI750205A7 (de) *	1974-02-05	1975-08-06	Sandoz Ag
DE2811361A1 (de) *	1978-03-16	1979-09-27	Hoechst Ag	Neue isochinolinaldehyde und verfahren zu ihrer herstellung
DE3244594A1 (de) *	1982-12-02	1984-06-07	Hoechst Ag, 6230 Frankfurt	1-phenylisochinolinderivate und verfahren zu ihrer herstellung, diese verbindung enthaltende pharmazeutische praeparate und deren anwendung
HU196758B (en) *	1986-05-21	1989-01-30	Gyogyszerkutato Intezet	Process for production of 3-hidroxi-methil-quinolines and medical compositions containing them
CA1330560C (en) *	1986-05-21	1994-07-05	Maurits E. A. Vandewalle	Di- and tetrahydroisoquinoline derivatives

1988
- 1988-01-08 GB GB888800397A patent/GB8800397D0/en active Pending
1989
- 1989-01-03 HU HU8911A patent/HU205083B/hu not_active IP Right Cessation
- 1989-01-04 IT IT8947504A patent/IT1229523B/it active
- 1989-01-04 GB GB8900102A patent/GB2213482B/en not_active Expired - Lifetime
- 1989-01-05 CA CA000587599A patent/CA1332944C/en not_active Expired - Fee Related
- 1989-01-05 SE SE8900039A patent/SE501548C2/sv unknown
- 1989-01-05 ES ES8900053A patent/ES2010071A6/es not_active Expired
- 1989-01-05 DE DE3900233A patent/DE3900233C2/de not_active Expired - Fee Related
- 1989-01-06 BE BE8900018A patent/BE1002730A3/fr not_active IP Right Cessation
- 1989-01-06 MY MYPI89000013A patent/MY103963A/en unknown
- 1989-01-06 FI FI890072A patent/FI90865C/fi not_active IP Right Cessation
- 1989-01-06 LU LU87423A patent/LU87423A1/fr unknown
- 1989-01-06 JP JP1001898A patent/JPH0649686B2/ja not_active Expired - Lifetime
- 1989-01-06 ZA ZA89133A patent/ZA89133B/xx unknown
- 1989-01-06 NZ NZ227561A patent/NZ227561A/xx unknown
- 1989-01-06 PH PH38011A patent/PH25640A/en unknown
- 1989-01-06 FR FR898900128A patent/FR2625743B1/fr not_active Expired - Lifetime
- 1989-01-06 PL PL1989277092A patent/PL156099B1/pl unknown
- 1989-01-06 NL NL8900029A patent/NL8900029A/nl not_active Application Discontinuation
- 1989-01-06 IL IL8889989A patent/IL88899A/en not_active IP Right Cessation
- 1989-01-06 AU AU27795/89A patent/AU622429B2/en not_active Ceased
- 1989-01-06 PT PT89405A patent/PT89405B/pt not_active IP Right Cessation
- 1989-01-06 DK DK005789A patent/DK5789A/da not_active Application Discontinuation
- 1989-01-06 IE IE3789A patent/IE61914B1/en not_active IP Right Cessation
- 1989-01-07 KR KR1019890000151A patent/KR0142686B1/ko not_active Expired - Fee Related
- 1989-01-09 AT AT0003589A patent/AT394365B/de not_active IP Right Cessation
- 1989-01-09 CH CH59/89A patent/CH678727A5/de not_active IP Right Cessation
- 1989-01-09 GR GR890100008A patent/GR1002750B/el unknown
1990
- 1990-04-10 US US07/507,702 patent/US4980359A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
IL88899A (en)	1994-07-31
MY103963A (en)	1993-10-30
SE8900039L (sv)	1989-07-09
DE3900233A1 (de)	1989-07-20
FR2625743A1 (fr)	1989-07-13
DK5789A (da)	1989-07-09
PH25640A (en)	1991-08-21
NL8900029A (nl)	1989-08-01
FI90865C (fi)	1994-04-11
FR2625743B1 (fr)	1990-11-09
GB8900102D0 (en)	1989-03-01
SE8900039D0 (sv)	1989-01-05
JPH01213267A (ja)	1989-08-28
AU622429B2 (en)	1992-04-09
GB2213482B (en)	1991-09-11
FI890072A0 (fi)	1989-01-06
HU205083B (en)	1992-03-30
FI890072A7 (fi)	1989-07-09
IL88899A0 (en)	1989-08-15
LU87423A1 (fr)	1989-08-30
PL156099B1 (pl)	1992-02-28
FI90865B (fi)	1993-12-31
US4980359A (en)	1990-12-25
GB2213482A (en)	1989-08-16
DK5789D0 (da)	1989-01-06
IT8947504A0 (it)	1989-01-04
GR1002750B (el)	1997-08-26
AU2779589A (en)	1989-07-20
DE3900233C2 (de)	2000-04-27
AT394365B (de)	1992-03-25
NZ227561A (en)	1991-11-26
CH678727A5 (de)	1991-10-31
ZA89133B (en)	1990-09-26
IE890037L (en)	1989-07-08
ES2010071A6 (es)	1989-10-16
KR0142686B1 (ko)	1998-07-15
PL277092A1 (en)	1989-09-04
JPH0649686B2 (ja)	1994-06-29
PT89405B (pt)	1993-09-30
ATA3589A (de)	1991-09-15
IT1229523B (it)	1991-09-04
CA1332944C (en)	1994-11-08
GR890100008A (el)	1994-03-31
IE61914B1 (en)	1994-11-30
PT89405A (pt)	1990-02-08
BE1002730A3 (fr)	1991-05-21
KR890011851A (ko)	1989-08-22
GB8800397D0 (en)	1988-02-10
HUT52061A (en)	1990-06-28

Publication	Publication Date	Title
US4980359A (en)	1990-12-25	Isoquinoline derivatives and their use
US5177085A (en)	1993-01-05	Dihydro-isoquinoline derivatives, processes for their production, pharmaceutical compositions containing them, and their use in treating asthma
DK169337B1 (da)	1994-10-10	Xanthinforbindelser, farmaceutisk præparat indeholdende disse, xanthinforbindelser til anvendelse som et farmaceutisk middel samt fremgangsmåde til fremstilling af forbindelserne
US5905156A (en)	1999-05-18	Benzopyrans and pharmaceutical compositions containing them
US4791121A (en)	1988-12-13	4-phenyl-4-(N-(phenyl)amido) piperidine derivatives and pharmaceutical compositions and method employing such compounds
US5574049A (en)	1996-11-12	2,2-dialkyl- and 2,2-dialkyl-3,4-dihydro-3-hydroxy-2H-1-benzopyrans
WO1994012493A1 (en)	1994-06-09	2,2-dialkyl- and 2,2-dialkyl-3,4-dihydro-3-hydroxy-2h-1-benzopyr ans, their use as pharmaceuticals
EP0035819A1 (de)	1981-09-16	Chinolinderivate, solche Verbindungen enthaltende pharmazeutische Zusammensetzungen und Verfahren zur Herstellung dieser Verbindungen
EP0435235A1 (de)	1991-07-03	Isochinolinderivate und ihre Salze als Proteasehemmer
JPH03294277A (ja)	1991-12-25	ピペリジン誘導体
JPH02135A (ja)	1990-01-05	多還式化合物とこれを含有する医薬組成物
AU665040B2 (en)	1995-12-14	4-carboxamido-6(pyridin-4-yl substituted benzopyran derivatives
JPH0859654A (ja)	1996-03-05	中枢神経系治療用薬剤としての６−アミノ−１，４−ジヒドロピリジン類の使用およびそれらの製造方法
MXPA97009004A (en)	1998-10-15	Benzopira
PL154160B1 (pl)	1991-07-31	Sposób wytwarzania nowych pochodnych ksantyny