MX2014008957A - Pirano y furanoquinolinas sustituidas, su preparacion y su uso como medicamentos. - Google Patents

Pirano y furanoquinolinas sustituidas, su preparacion y su uso como medicamentos.

Info

Publication number: MX2014008957A
Authority: MX; Mexico
Prior art keywords: quinoline; hydrochloride; hexahydro; cyclohexyl; 4asr
Prior art date: 2012-01-24

Application number

MX2014008957A

Other languages

English (en)

Spanish (es)

Inventor

José-Luis Diaz-Fernández

Ute Christmann

Original Assignee

Esteve Labor Dr

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.)

2012-01-24

Filing date

2013-01-24

Publication date

2014-10-14

2013-01-24 Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr

2014-10-14 Publication of MX2014008957A publication Critical patent/MX2014008957A/es

Links

238000002360 preparation method Methods 0.000 title claims abstract description 17
239000003814 drug Substances 0.000 title claims abstract description 14
NBIQERZFHYWUCH-UHFFFAOYSA-N furo[2,3-h]quinoline Chemical class C1=CN=C2C(C=CO3)=C3C=CC2=C1 NBIQERZFHYWUCH-UHFFFAOYSA-N 0.000 title abstract description 9
238000000034 method Methods 0.000 claims abstract description 45
108010085082 sigma receptors Proteins 0.000 claims abstract description 23
230000008569 process Effects 0.000 claims abstract description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 117
150000001875 compounds Chemical class 0.000 claims description 112
-1 unsaturated aliphatic radical Chemical class 0.000 claims description 102
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 94
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 20
125000005842 heteroatom Chemical group 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
229920006395 saturated elastomer Polymers 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
125000005921 isopentoxy group Chemical group 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
208000004454 Hyperalgesia Diseases 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000002950 monocyclic group Chemical group 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
208000002193 Pain Diseases 0.000 claims description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
229940002612 prodrug Drugs 0.000 claims description 10
239000000651 prodrug Substances 0.000 claims description 10
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RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
TZYSTIRJCFTKHC-UHFFFAOYSA-N 5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline-9-carboxylic acid;hydrochloride Chemical compound Cl.C12CCCOC2C2=CC(C(=O)O)=CC=C2NC1C1CCCCC1 TZYSTIRJCFTKHC-UHFFFAOYSA-N 0.000 claims description 6
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
239000004202 carbamide Substances 0.000 claims description 5
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DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
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125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229960003920 cocaine Drugs 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
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SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
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239000003960 organic solvent Substances 0.000 claims description 3
239000003586 protic polar solvent Substances 0.000 claims description 3
229940124530 sulfonamide Drugs 0.000 claims description 3
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DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
ODTYUTJMXXHBJL-UHFFFAOYSA-N 5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline-7-carboxylic acid;hydrochloride Chemical compound Cl.N1C=2C(C(=O)O)=CC=CC=2C2OCCCC2C1C1CCCCC1 ODTYUTJMXXHBJL-UHFFFAOYSA-N 0.000 claims description 2
OIVPDZVDKXTHAU-UHFFFAOYSA-N 5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline-8-carboxylic acid;hydrochloride Chemical compound Cl.N1C2=CC(C(=O)O)=CC=C2C2OCCCC2C1C1CCCCC1 OIVPDZVDKXTHAU-UHFFFAOYSA-N 0.000 claims description 2
JLZLHBZPTFPBFA-UHFFFAOYSA-N 5-cyclohexyl-7-methyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-8-carboxylic acid hydrochloride Chemical compound CC1=C(C=CC2=C1NC(C3C2OCCC3)C4CCCCC4)C(=O)O.Cl JLZLHBZPTFPBFA-UHFFFAOYSA-N 0.000 claims description 2
239000002841 Lewis acid Substances 0.000 claims description 2
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 2
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 claims description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 2
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WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 2
150000003235 pyrrolidines Chemical class 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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FJXHVZSHZQNFGR-UHFFFAOYSA-N 5-cyclohexyl-3,4,4a,5,6,10b-hexahydro-2h-pyrano[3,2-c]quinoline-10-carboxylic acid;hydrochloride Chemical compound Cl.C12CCCOC2C=2C(C(=O)O)=CC=CC=2NC1C1CCCCC1 FJXHVZSHZQNFGR-UHFFFAOYSA-N 0.000 claims 1
JFSBJSONNKEYEF-UHFFFAOYSA-N 5-cyclopentyl-7-methyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline-8-carboxylic acid hydrochloride Chemical compound CC1=C(C=CC2=C1NC(C3C2OCCC3)C4CCCC4)C(=O)O.Cl JFSBJSONNKEYEF-UHFFFAOYSA-N 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
WIYDEVSKVYFPPV-UHFFFAOYSA-N pentanamide;hydrochloride Chemical compound Cl.CCCCC(N)=O WIYDEVSKVYFPPV-UHFFFAOYSA-N 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered

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MX2014008957A 2012-01-24 2013-01-24 Pirano y furanoquinolinas sustituidas, su preparacion y su uso como medicamentos. MX2014008957A (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP12382020.1A EP2620438A1 (en)	2012-01-24	2012-01-24	Substituted pyrano and furanoquinolines, their preparation and use as medicaments
PCT/EP2013/051328 WO2013110698A1 (en)	2012-01-24	2013-01-24	Substituted pyrano and furanoquinolines, their preparation and use as medicaments

Publications (1)

Publication Number	Publication Date
MX2014008957A true MX2014008957A (es)	2014-10-14

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ID=47624058

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
MX2014008957A MX2014008957A (es)	2012-01-24	2013-01-24	Pirano y furanoquinolinas sustituidas, su preparacion y su uso como medicamentos.

Country Status (9)

Country	Link
US (2)	US9193738B2 (2)
EP (2)	EP2620438A1 (2)
JP (1)	JP2015504908A (2)
CN (1)	CN104245704A (2)
CA (1)	CA2862535A1 (2)
ES (1)	ES2627530T3 (2)
IN (1)	IN2014MN01492A (2)
MX (1)	MX2014008957A (2)
WO (1)	WO2013110698A1 (2)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2620438A1 (en) *	2012-01-24	2013-07-31	Laboratorios Del. Dr. Esteve, S.A.	Substituted pyrano and furanoquinolines, their preparation and use as medicaments
WO2021050721A1 (en) *	2019-09-10	2021-03-18	Emory University	Quinoline derivatives and uses in managing cancer
WO2024105225A1 (en)	2022-11-18	2024-05-23	Universitat De Barcelona	Synergistic combinations of a sigma receptor 1 (s1r) antagonist and a soluble epoxide hydrolase inhibitor (sehi) and their use in the treatment of pain

Family Cites Families (10)

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Publication number	Priority date	Publication date	Assignee	Title
US3631050A (en) *	1968-11-13	1971-12-28	Parke Davis & Co	Hexahydro-9b-methylfuro(3 2-c) quinoline compounds
JP4222893B2 (ja)	2003-07-15	2009-02-12	シャープ株式会社	画像補正装置、画像補正方法、画像補正プログラム、および画像補正プログラムを記録したコンピュータ読取り可能な記録媒体
SI1761515T1 (sl)	2003-12-20	2009-02-28	Merck Patent Gmbh	2-(hetero-)aril substituirani derivati tetrahidrokinolina
JP2007084437A (ja)	2003-12-26	2007-04-05	Dai Ichi Seiyaku Co Ltd	アミノアルキルピラゾール誘導体
EP1634873A1 (en)	2004-08-27	2006-03-15	Laboratorios Del Dr. Esteve, S.A.	Sigma receptor inhibitors
BRPI0514736A (pt) *	2004-08-27	2008-06-24	Esteve Labor Dr	inibidores do receptor sigma
EP1829869A1 (en)	2006-03-02	2007-09-05	Laboratorios Del Dr. Esteve, S.A.	4,5,6,7-Tetrahydrobenzo[b]thiophene derivatives and their use as sigma receptor ligands
EP1847542A1 (en) *	2006-04-21	2007-10-24	Laboratorios del Dr. Esteve S.A.	Spiro[benzopyran] or spiro[benzofuran] derivatives which inhibit the sigma receptor
EP2070933A1 (en)	2007-12-07	2009-06-17	Laboratorios del Dr. Esteve S.A.	Tricyclic triazolic compounds
EP2620438A1 (en) *	2012-01-24	2013-07-31	Laboratorios Del. Dr. Esteve, S.A.	Substituted pyrano and furanoquinolines, their preparation and use as medicaments

2012
- 2012-01-24 EP EP12382020.1A patent/EP2620438A1/en not_active Withdrawn
2013
- 2013-01-24 ES ES13702004.6T patent/ES2627530T3/es active Active
- 2013-01-24 US US14/374,081 patent/US9193738B2/en not_active Expired - Fee Related
- 2013-01-24 CN CN201380009118.4A patent/CN104245704A/zh active Pending
- 2013-01-24 WO PCT/EP2013/051328 patent/WO2013110698A1/en not_active Ceased
- 2013-01-24 CA CA2862535A patent/CA2862535A1/en not_active Abandoned
- 2013-01-24 JP JP2014553714A patent/JP2015504908A/ja not_active Ceased
- 2013-01-24 MX MX2014008957A patent/MX2014008957A/es unknown
- 2013-01-24 IN IN1492MUN2014 patent/IN2014MN01492A/en unknown
- 2013-01-24 EP EP13702004.6A patent/EP2807169B1/en not_active Not-in-force
2015
- 2015-08-20 US US14/830,888 patent/US9408842B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP2620438A1 (en)	2013-07-31
EP2807169A1 (en)	2014-12-03
US9408842B2 (en)	2016-08-09
IN2014MN01492A (2)	2015-04-17
EP2807169B1 (en)	2017-03-01
HK1204613A1 (en)	2015-11-27
WO2013110698A1 (en)	2013-08-01
CA2862535A1 (en)	2013-08-01
ES2627530T3 (es)	2017-07-28
US20150031692A1 (en)	2015-01-29
US20150352098A1 (en)	2015-12-10
US9193738B2 (en)	2015-11-24
JP2015504908A (ja)	2015-02-16
CN104245704A (zh)	2014-12-24

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