CA2125681A1 - Derives 4-amino-3-acylquinolines et leur utilisation comme inhibiteurs de la secretion acide gastrique - Google Patents

Derives 4-amino-3-acylquinolines et leur utilisation comme inhibiteurs de la secretion acide gastrique

Info

Publication number: CA2125681A1
Authority: CA; Canada
Prior art keywords: denotes; methylphenylamino; quinolin; ester; butyryl
Prior art date: 1991-12-12
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA002125681A

Other languages

English (en)

Inventor

Gerhard Gundler

Georg Rainer

Robert John Ife

Colin Andrew Leach

Stefan Postius

Richard Riedel

Hartmann Schaefer

Jorg Senn-Bilfinger

Wolfgang-Alexander Simon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SmithKline Beecham Intercredit BV

Original Assignee

Individual

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.)

1991-12-12

Filing date

1992-12-10

Publication date

1993-06-24

1992-12-10 Application filed by Individual filed Critical Individual

1993-06-24 Publication of CA2125681A1 publication Critical patent/CA2125681A1/fr

Status Abandoned legal-status Critical Current

Links

230000027119 gastric acid secretion Effects 0.000 title abstract description 4
239000003112 inhibitor Substances 0.000 title abstract description 3
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 56
150000003839 salts Chemical class 0.000 claims abstract description 34
-1 oxytrimethylene Chemical group 0.000 claims abstract description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 11
239000005977 Ethylene Substances 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 8
150000002431 hydrogen Chemical class 0.000 claims abstract description 7
125000006353 oxyethylene group Chemical group 0.000 claims abstract description 7
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 4
150000002367 halogens Chemical class 0.000 claims abstract description 4
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 4
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 5
238000002560 therapeutic procedure Methods 0.000 claims abstract 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
NAXRYHGOQXSKKN-UHFFFAOYSA-N 4-[2-[3-butanoyl-4-(2-methylanilino)quinolin-8-yl]oxyethoxy]-4-oxobutanoic acid Chemical compound CCCC(=O)C1=CN=C2C(OCCOC(=O)CCC(O)=O)=CC=CC2=C1NC1=CC=CC=C1C NAXRYHGOQXSKKN-UHFFFAOYSA-N 0.000 claims description 3
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
150000001990 dicarboxylic acid derivatives Chemical class 0.000 claims description 2
230000002496 gastric effect Effects 0.000 claims description 2
230000005764 inhibitory process Effects 0.000 claims description 2
230000028327 secretion Effects 0.000 claims description 2
NVBFKAKHBKRUJI-UHFFFAOYSA-N 4-[2-[3-butanoyl-4-(4-fluoro-2-methylanilino)quinolin-8-yl]oxyethoxy]-4-oxobutanoic acid Chemical compound C(CCC)(=O)C=1C=NC2=C(C=CC=C2C1NC1=C(C=C(C=C1)F)C)OCCOC(CCC(=O)O)=O NVBFKAKHBKRUJI-UHFFFAOYSA-N 0.000 claims 2
XNWJKPSLFXCIGK-UHFFFAOYSA-N 3-[2-[3-butanoyl-4-(2-methylanilino)quinolin-8-yl]oxyethoxy]-3-oxopropanoic acid Chemical compound C(CCC)(=O)C=1C=NC2=C(C=CC=C2C1NC1=C(C=CC=C1)C)OCCOC(CC(=O)O)=O XNWJKPSLFXCIGK-UHFFFAOYSA-N 0.000 claims 1
WMIZHTSSFXZTNZ-UHFFFAOYSA-N 4-[2-[4-(4-fluoro-2-methylanilino)-3-propanoylquinolin-8-yl]oxyethoxy]-4-oxobutanoic acid Chemical compound C(CC)(=O)C=1C=NC2=C(C=CC=C2C1NC1=C(C=C(C=C1)F)C)OCCOC(CCC(=O)O)=O WMIZHTSSFXZTNZ-UHFFFAOYSA-N 0.000 claims 1
AFSYDQILKMFUJQ-UHFFFAOYSA-N 5-[2-[3-butanoyl-4-(2-methylanilino)quinolin-8-yl]oxyethoxy]-2,2-dimethyl-5-oxopentanoic acid Chemical compound C(CCC)(=O)C=1C=NC2=C(C=CC=C2C1NC1=C(C=CC=C1)C)OCCOC(CCC(C(=O)O)(C)C)=O AFSYDQILKMFUJQ-UHFFFAOYSA-N 0.000 claims 1
XWHKYPRYTOKVIZ-UHFFFAOYSA-N 5-[2-[3-butanoyl-4-(2-methylanilino)quinolin-8-yl]oxyethoxy]-3-methyl-5-oxopentanoic acid Chemical compound CCCC(=O)C1=CN=C2C(OCCOC(=O)CC(C)CC(O)=O)=CC=CC2=C1NC1=CC=CC=C1C XWHKYPRYTOKVIZ-UHFFFAOYSA-N 0.000 claims 1
LOLRNNCGNNWETC-UHFFFAOYSA-N 5-[2-[3-butanoyl-4-(2-methylanilino)quinolin-8-yl]oxyethoxy]-5-oxopentanoic acid Chemical compound C(CCC)(=O)C=1C=NC2=C(C=CC=C2C1NC1=C(C=CC=C1)C)OCCOC(CCCC(=O)O)=O LOLRNNCGNNWETC-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
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 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 15
239000000243 solution Substances 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 11
101150065749 Churc1 gene Proteins 0.000 description 11
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239000003814 drug Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 10
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
239000000047 product Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
239000001384 succinic acid Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
GTOFKXZQQDSVFH-UHFFFAOYSA-N 2-benzylsuccinic acid Chemical compound OC(=O)CC(C(O)=O)CC1=CC=CC=C1 GTOFKXZQQDSVFH-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
210000002784 stomach Anatomy 0.000 description 5
238000011282 treatment Methods 0.000 description 5
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
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238000011321 prophylaxis Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
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239000003795 chemical substances by application Substances 0.000 description 3
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210000000936 intestine Anatomy 0.000 description 3
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RFPMGSKVEAUNMZ-UHFFFAOYSA-N pentylidene Chemical group [CH2+]CCC[CH-] RFPMGSKVEAUNMZ-UHFFFAOYSA-N 0.000 description 1
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230000000144 pharmacologic effect Effects 0.000 description 1
RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
229960004633 pirenzepine Drugs 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
125000006410 propenylene group Chemical group 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
229960000620 ranitidine Drugs 0.000 description 1
BZGIPVGCJGXQTA-UHFFFAOYSA-N s-[2-(diethylamino)ethyl] n,n-diphenylcarbamothioate Chemical compound C=1C=CC=CC=1N(C(=O)SCCN(CC)CC)C1=CC=CC=C1 BZGIPVGCJGXQTA-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229950004351 telenzepine Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960002372 tetracaine Drugs 0.000 description 1
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Landscapes

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

CA002125681A 1991-12-12 1992-12-10 Derives 4-amino-3-acylquinolines et leur utilisation comme inhibiteurs de la secretion acide gastrique Abandoned CA2125681A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB919126438A GB9126438D0 (en)	1991-12-12	1991-12-12	New quinoline derivatives
GB9126438.2		1991-12-12

Publications (1)

Publication Number	Publication Date
CA2125681A1 true CA2125681A1 (fr)	1993-06-24

Family

ID=10706172

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002125681A Abandoned CA2125681A1 (fr)	1991-12-12	1992-12-10	Derives 4-amino-3-acylquinolines et leur utilisation comme inhibiteurs de la secretion acide gastrique

Country Status (8)

Country	Link
EP (1)	EP0642500A1 (fr)
JP (1)	JPH07501812A (fr)
AU (1)	AU665223B2 (fr)
CA (1)	CA2125681A1 (fr)
GB (1)	GB9126438D0 (fr)
MX (1)	MX9207162A (fr)
WO (1)	WO1993012090A1 (fr)
ZA (1)	ZA929568B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IS4164A (is) *	1993-06-11	1994-12-12	Ab Astra	Efnasambönd sem hindra flæði magasýru
US5556863A (en) *	1993-06-11	1996-09-17	Astra Aktiebolag	Compound for gastric acid secretion inhibition
UA80393C2 (uk)	2000-12-07	2007-09-25	Алтана Фарма Аг	Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці
MY140561A (en)	2002-02-20	2009-12-31	Nycomed Gmbh	Dosage form containing pde 4 inhibitor as active ingredient

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8621425D0 (en) *	1986-09-05	1986-10-15	Smith Kline French Lab	Compounds
GB8804444D0 (en) *	1988-02-25	1988-03-23	Smithkline Beckman Intercredit	Compounds
GB8918265D0 (en) *	1989-08-10	1989-09-20	Smithkline Beckman Intercredit	Compounds
HUT67609A (en) *	1991-01-29	1995-04-28	Smithkline Beecham Intercredit	Salts of a 4-amino-3-acyl-quinoline derivative, their preparation and pharmaceutical compositions comprising them

1991
- 1991-12-12 GB GB919126438A patent/GB9126438D0/en active Pending
1992
- 1992-12-10 CA CA002125681A patent/CA2125681A1/fr not_active Abandoned
- 1992-12-10 WO PCT/EP1992/002898 patent/WO1993012090A1/fr not_active Ceased
- 1992-12-10 ZA ZA929568A patent/ZA929568B/xx unknown
- 1992-12-10 AU AU31585/93A patent/AU665223B2/en not_active Ceased
- 1992-12-10 MX MX9207162A patent/MX9207162A/es unknown
- 1992-12-10 JP JP5510627A patent/JPH07501812A/ja active Pending
- 1992-12-10 EP EP93900050A patent/EP0642500A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
AU665223B2 (en)	1995-12-21
EP0642500A1 (fr)	1995-03-15
ZA929568B (en)	1994-06-10
AU3158593A (en)	1993-07-19
MX9207162A (es)	1994-08-31
GB9126438D0 (en)	1992-02-12
WO1993012090A1 (fr)	1993-06-24
JPH07501812A (ja)	1995-02-23

Publication	Publication Date	Title
EP0310950B1 (fr)	1993-01-13	Quinoléines intermédiaires pour la synthèse des 1H-imidazo[4,5-c]quinoléines et 1H-imidazo[4,5-c]quinoléine-4-amines
US4698348A (en)	1987-10-06	1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents
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