NO864518L - Fremgangsmaate for fremstilling av thiazolo(4,5-c)kinoliner - Google Patents

Fremgangsmaate for fremstilling av thiazolo(4,5-c)kinoliner

Info

Publication number: NO864518L
Authority: NO; Norway
Prior art keywords: general formula; quinoline; thiazolo; acid addition; acid
Prior art date: 1985-11-12

Application number

NO864518A

Other languages

English (en)

Norwegian (no)

Other versions

NO864518D0 (no

Inventor

Jozsef Knoll

Edit Berenyi

Katalin Budai

Berta Knoll

Zsuzsa Fuerts

Julia Timbr

Gabriella Zsila

Ildiko Niklya

Lujza Petoz

Attila Mandi

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1985-11-12

Filing date

1986-11-12

Publication date

1987-05-13

1986-11-12 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1986-11-12 Publication of NO864518D0 publication Critical patent/NO864518D0/no

1987-05-13 Publication of NO864518L publication Critical patent/NO864518L/no

Links

238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 4
229940111121 antirheumatic drug quinolines Drugs 0.000 title 1
150000003248 quinolines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 36
239000002253 acid Substances 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
YJBLTYRYUXKJLE-UHFFFAOYSA-N 3-amino-1h-quinoline-4-thione Chemical compound C1=CC=C2C(=S)C(N)=CNC2=C1 YJBLTYRYUXKJLE-UHFFFAOYSA-N 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
OWHMGQJEHHCWCJ-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]quinoline Chemical class C1=CC=CC2=C(SC=N3)C3=CN=C21 OWHMGQJEHHCWCJ-UHFFFAOYSA-N 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
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150000002367 halogens Chemical class 0.000 claims description 5
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OSUDJKDDCBAIBJ-UHFFFAOYSA-N ethanesulfonic acid;[1,3]thiazolo[4,5-c]quinoline Chemical compound CCS(O)(=O)=O.C1=CC=CC2=C(SC=N3)C3=CN=C21 OSUDJKDDCBAIBJ-UHFFFAOYSA-N 0.000 description 6
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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210000003169 central nervous system Anatomy 0.000 description 2
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ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 2
229960004782 chlordiazepoxide Drugs 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
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FYWDUUCSIVYZLY-UHFFFAOYSA-N 2-(trifluoromethyl)-[1,3]thiazolo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(SC(C(F)(F)F)=N3)C3=CN=C21 FYWDUUCSIVYZLY-UHFFFAOYSA-N 0.000 description 1
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WJDUOAAAWXDSHV-UHFFFAOYSA-N 2-methyl-[1,3]thiazolo[4,5-c]quinoline Chemical compound C1=CC=CC2=C(SC(C)=N3)C3=CN=C21 WJDUOAAAWXDSHV-UHFFFAOYSA-N 0.000 description 1
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229960005181 morphine Drugs 0.000 description 1
KSHSRFOLLXJJGF-UHFFFAOYSA-N n-(7-chloro-4-sulfanylidene-1h-quinolin-3-yl)acetamide Chemical compound C1=C(Cl)C=CC2=C(S)C(NC(=O)C)=CN=C21 KSHSRFOLLXJJGF-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000004081 narcotic agent Substances 0.000 description 1
230000003533 narcotic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
210000004303 peritoneum Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
208000018299 prostration Diseases 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000012216 screening Methods 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
239000000932 sedative agent Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 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 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
IDELNEDBPWKHGK-UHFFFAOYSA-N thiobutabarbital Chemical compound CCC(C)C1(CC)C(=O)NC(=S)NC1=O IDELNEDBPWKHGK-UHFFFAOYSA-N 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO864518A 1985-11-12 1986-11-12 Fremgangsmaate for fremstilling av thiazolo(4,5-c)kinoliner NO864518L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU854304A HU197019B (en)	1985-11-12	1985-11-12	Process for producing thiqzolo (4,5-c) quinoline derivatives and pharmaceuticals comprising same

Publications (2)

Publication Number	Publication Date
NO864518D0 NO864518D0 (no)	1986-11-12
NO864518L true NO864518L (no)	1987-05-13

Family

ID=10967593

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO864518A NO864518L (no)	1985-11-12	1986-11-12	Fremgangsmaate for fremstilling av thiazolo(4,5-c)kinoliner

Country Status (24)

Country	Link
US (1)	US4904669A (de)
JP (1)	JPS62161792A (de)
CN (1)	CN86107754A (de)
AU (1)	AU592384B2 (de)
BE (1)	BE905719A (de)
BG (1)	BG46156A3 (de)
CH (1)	CH670829A5 (de)
DD (1)	DD254202A5 (de)
DE (1)	DE3638563A1 (de)
DK (1)	DK539786A (de)
ES (1)	ES2002543A6 (de)
FI (1)	FI864611A7 (de)
FR (1)	FR2603588A1 (de)
GB (1)	GB2184117B (de)
HU (1)	HU197019B (de)
IL (1)	IL80611A0 (de)
IT (1)	IT1213379B (de)
NL (1)	NL8602878A (de)
NO (1)	NO864518L (de)
PL (1)	PL148186B1 (de)
SE (1)	SE8604839L (de)
SU (1)	SU1544190A3 (de)
YU (1)	YU192186A (de)
ZA (1)	ZA868583B (de)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU199423B (en) *	1987-04-24	1990-02-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing 3-amino-4-/ethylthio/-quinoline and pharmaceutical compositions comprising such compounds
US6110929A (en)	1998-07-28	2000-08-29	3M Innovative Properties Company	Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof
US6677347B2 (en) *	2000-12-08	2004-01-13	3M Innovative Properties Company	Sulfonamido ether substituted imidazoquinolines
WO2004096144A2 (en) *	2003-04-28	2004-11-11	3M Innovative Properties Company	Compositions and methods for induction of opioid receptors
MXPA06001669A (es) *	2003-08-12	2006-04-28	3M Innovative Properties Co	Compuestos que contienen imidazo-oxima sustituidos.
NZ545412A (en) *	2003-08-27	2008-12-24	Coley Pharm Group Inc	Aryloxy and arylalkyleneoxy substituted imidazoquinolines
JP2007504269A (ja) *	2003-09-05	2007-03-01	スリーエムイノベイティブプロパティズカンパニー	Ｃｄ５＋ｂ細胞リンパ腫の治療方法
EP1673087B1 (de) *	2003-10-03	2015-05-13	3M Innovative Properties Company	Alkoxy-substituierte imidazochinoline
US7544697B2 (en) *	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
US20090075980A1 (en) *	2003-10-03	2009-03-19	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and Analogs Thereof
CN1906192A (zh) *	2003-11-14	2007-01-31	3M创新有限公司	羟胺取代的咪唑环化合物
WO2005048933A2 (en)	2003-11-14	2005-06-02	3M Innovative Properties Company	Oxime substituted imidazo ring compounds
AU2004293078B2 (en) *	2003-11-25	2012-01-19	3M Innovative Properties Company	Substituted imidazo ring systems and methods
JP2007517035A (ja) *	2003-12-29	2007-06-28	スリーエムイノベイティブプロパティズカンパニー	アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン
EP1699788A2 (de) *	2003-12-30	2006-09-13	3M Innovative Properties Company	Imidazochinolinyl-, imidazopyridinyl- und imidazonaphthyridinylsulfonamide
US8697873B2 (en) *	2004-03-24	2014-04-15	3M Innovative Properties Company	Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines
US8017779B2 (en) *	2004-06-15	2011-09-13	3M Innovative Properties Company	Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines
US7915281B2 (en) *	2004-06-18	2011-03-29	3M Innovative Properties Company	Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method
WO2006009826A1 (en) *	2004-06-18	2006-01-26	3M Innovative Properties Company	Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines
WO2006009832A1 (en) *	2004-06-18	2006-01-26	3M Innovative Properties Company	Substituted imidazo ring systems and methods
WO2006038923A2 (en) *	2004-06-18	2006-04-13	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
WO2006026760A2 (en) *	2004-09-02	2006-03-09	3M Innovative Properties Company	1-amino imidazo-containing compounds and methods
JP2008523076A (ja) *	2004-12-08	2008-07-03	スリーエムイノベイティブプロパティズカンパニー	免疫調節性の組成物、合剤、および方法
JP5313502B2 (ja)	2004-12-30	2013-10-09	スリーエムイノベイティブプロパティズカンパニー	置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物
CA2592904C (en) *	2004-12-30	2015-04-07	3M Innovative Properties Company	Chiral fused [1,2]imidazo[4,5-c] ring compounds
JP2008530022A (ja)	2005-02-04	2008-08-07	コーリーファーマシューティカルグループ，インコーポレイテッド	免疫反応調節物質を含む水性ゲル処方物
CA2602083A1 (en) *	2005-02-09	2006-08-09	Coley Pharmaceutical Group, Inc.	Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods
EP1846405A2 (de)	2005-02-11	2007-10-24	3M Innovative Properties Company	Oxim- und hydroxylaminsubstituierte imidazo-4,5-c-ringverbindungen und verfahren
CA2602683A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	Pyrazolopyridine-1,4-diamines and analogs thereof
CA2602590A1 (en)	2005-04-01	2006-10-12	Coley Pharmaceutical Group, Inc.	1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases
WO2008008432A2 (en) *	2006-07-12	2008-01-17	Coley Pharmaceutical Group, Inc.	Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods
JP7443357B2 (ja)	2018-10-23	2024-03-05	ビーエーエスエフソシエタス・ヨーロピア	三環式の殺有害生物化合物
AU2021256876A1 (en)	2020-04-14	2022-11-03	Basf Se	Tricyclic pesticidal compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2024207A (en) *	1978-05-26	1980-01-09	Lepetit Spa	New tricyclic ortho-fused heterocyclic compounds
HU196308B (en) *	1985-11-12	1988-11-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing pharmaceutical compositions containing 2-methyl-thiazolo/4,5-c/quinoline as active component

1985
- 1985-11-12 HU HU854304A patent/HU197019B/hu not_active IP Right Cessation
1986
- 1986-11-07 BE BE1/011572A patent/BE905719A/fr not_active IP Right Cessation
- 1986-11-10 CH CH4491/86A patent/CH670829A5/de not_active IP Right Cessation
- 1986-11-12 FI FI864611A patent/FI864611A7/fi not_active Application Discontinuation
- 1986-11-12 YU YU01921/86A patent/YU192186A/xx unknown
- 1986-11-12 US US06/929,353 patent/US4904669A/en not_active Expired - Fee Related
- 1986-11-12 SE SE8604839A patent/SE8604839L/xx not_active Application Discontinuation
- 1986-11-12 AU AU65089/86A patent/AU592384B2/en not_active Expired - Fee Related
- 1986-11-12 IT IT8622312A patent/IT1213379B/it active
- 1986-11-12 FR FR8615655A patent/FR2603588A1/fr active Pending
- 1986-11-12 PL PL1986262346A patent/PL148186B1/pl unknown
- 1986-11-12 ES ES8603003A patent/ES2002543A6/es not_active Expired
- 1986-11-12 DK DK539786A patent/DK539786A/da not_active Application Discontinuation
- 1986-11-12 DD DD86296208A patent/DD254202A5/de not_active IP Right Cessation
- 1986-11-12 ZA ZA868583A patent/ZA868583B/xx unknown
- 1986-11-12 GB GB8627043A patent/GB2184117B/en not_active Expired
- 1986-11-12 NL NL8602878A patent/NL8602878A/nl not_active Application Discontinuation
- 1986-11-12 NO NO864518A patent/NO864518L/no unknown
- 1986-11-12 SU SU864028529A patent/SU1544190A3/ru active
- 1986-11-12 JP JP61267869A patent/JPS62161792A/ja active Pending
- 1986-11-12 DE DE19863638563 patent/DE3638563A1/de not_active Withdrawn
- 1986-11-12 BG BG77078A patent/BG46156A3/xx unknown
- 1986-11-12 IL IL80611A patent/IL80611A0/xx unknown
- 1986-11-12 CN CN198686107754A patent/CN86107754A/zh active Pending

Also Published As

Publication number	Publication date
YU192186A (en)	1988-10-31
IT8622312A0 (it)	1986-11-12
HUT44260A (en)	1988-02-29
FI864611A0 (fi)	1986-11-12
DK539786A (da)	1987-05-13
ES2002543A6 (es)	1988-08-16
ZA868583B (en)	1987-08-26
CN86107754A (zh)	1987-08-05
SE8604839D0 (sv)	1986-11-12
PL262346A1 (en)	1988-03-03
NO864518D0 (no)	1986-11-12
PL148186B1 (en)	1989-09-30
NL8602878A (nl)	1987-06-01
SE8604839L (sv)	1987-05-13
FR2603588A1 (fr)	1988-03-11
BG46156A3 (en)	1989-10-16
DE3638563A1 (de)	1987-06-25
GB2184117A (en)	1987-06-17
DD254202A5 (de)	1988-02-17
HU197019B (en)	1989-02-28
CH670829A5 (de)	1989-07-14
GB8627043D0 (en)	1986-12-10
JPS62161792A (ja)	1987-07-17
IL80611A0 (en)	1987-02-27
AU6508986A (en)	1987-05-14
US4904669A (en)	1990-02-27
DK539786D0 (da)	1986-11-12
IT1213379B (it)	1989-12-20
BE905719A (fr)	1987-05-07
AU592384B2 (en)	1990-01-11
SU1544190A3 (ru)	1990-02-15
FI864611A7 (fi)	1987-05-13
GB2184117B (en)	1989-10-11

Publication	Publication Date	Title
AU592384B2 (en)	1990-01-11	Thiazolo(4,5-c)quinolines
KR900006853B1 (ko)	1990-09-22	약리학적으로 활성인 피라졸로/4,3-c/피리딘의 제조방법
KR101383228B1 (ko)	2014-04-09	Ａ3 아데노신 수용체 알로스테릭 조절제
RU2300523C2 (ru)	2007-06-10	ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ ИНДЕНО[ [1,2-с] ИЗОХИНОЛИНА, КОМПОЗИЦИИ И СПОСОБЫ ЛЕЧЕНИЯ НА ИХ ОСНОВЕ
NZ264887A (en)	1996-12-20	Heterocyclic carboxamides
SK99795A3 (en)	1995-12-06	Imidazopyrimidines, method of their preparation, treating with their contents and use
ITMI20012060A1 (it)	2003-04-05	Nuovi eterocilcli n-acilati
SK283536B6 (sk)	2003-09-11	Pyridylftalazindióny, spôsob ich prípravy a použitie a farmaceutické prostriedky na ich báze
KR910006986B1 (ko)	1991-09-14	치환된 5,11-디하이드로-6H-디벤즈[b,e]아제핀-6-온의 제조방법
CN115925699B (zh)	2023-10-03	具有镇痛活性的稠环化合物及其制备方法与用途
MacLeod et al.	1995	Identification of 3, 5-dihydro-2-aryl-1H-pyrazolo [3, 4-c] quinoline-1, 4 (2H)-diones as novel high-affinity glycine site N-methyl-D-aspartate antagonists
US20130005709A1 (en)	2013-01-03	Sulfone compounds as 5-ht6 receptor ligands
HU182562B (en)	1984-02-28	Process for preparing new 4-amino-2-piperidino-quinazoline derivatives
CN106928311B (zh)	2019-06-04	柠檬苦素衍生物、其制备方法及医药用途
AU623205B2 (en)	1992-05-07	N-pyridinyl-9h-carbazol-9-amines, a process their preparation and their use as medicaments
US4778811A (en)	1988-10-18	Pharmaceutical compositions of 2-methyl-thiazolo[4,5-c]quinoline
KR100557804B1 (ko)	2006-06-20	인돌로모르피난유도체및뇌장해치료·예방제
HU220874B1 (en)	2002-06-29	Imidazopyridine-azolidinones, process for producing them, the use thereof and pharmaceutical compositions containing them
DK149753B (da)	1986-09-22	Analogifremgangsmaade til fremstilling af morfinderivater
JP3727569B2 (ja)	2005-12-14	テトラヒドロキナゾリン−２，４−ジオンおよびそれらの治療用途
KR0140504B1 (ko)	1998-06-01	양쪽성 3환식 화합물
US4350698A (en)	1982-09-21	Antiallergic imidosulfamides
SK8732000A3 (en)	2000-11-07	Potassium channel openers
PL94080B1 (en)	1977-07-30	Lactams and process for their manufacture[US3951985A]
AU602209B2 (en)	1990-10-04	Quinoline thioethers