CA1144163A - Derives sulfures de l'isoquinolines; methode de preparation, et compositions pharmaceutiques qui en renferment - Google Patents

Derives sulfures de l'isoquinolines; methode de preparation, et compositions pharmaceutiques qui en renferment

Info

Publication number: CA1144163A
Authority: CA; Canada
Prior art keywords: general formula; alpha; dotted line; dihydro; isoquinolyl
Prior art date: 1980-07-04
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.): Expired

Application number

CA000355538A

Other languages

English (en)

Inventor

Kalman Takacs

Gabor Kovacs

Maria H. Pap

Antal Simay

Ilona K. Ajzert

Peter Literati-Nagy

Marian E. Puskas

Gyula Sebestyen

Zoltan Sumeghy

Istvan Stadler

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.)

Chinoin Private Co Ltd

Original Assignee

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

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.)

1980-07-04

Filing date

1980-07-04

Publication date

1983-04-05

1980-07-04 Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

1980-07-04 Priority to CA000355538A priority Critical patent/CA1144163A/fr

1983-04-05 Application granted granted Critical

1983-04-05 Publication of CA1144163A publication Critical patent/CA1144163A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 64
238000002360 preparation method Methods 0.000 title claims description 9
229910052717 sulfur Inorganic materials 0.000 title abstract description 40
239000008194 pharmaceutical composition Substances 0.000 title abstract description 3
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title abstract 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract 2
239000011593 sulfur Substances 0.000 title abstract 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 71
150000001875 compounds Chemical class 0.000 claims abstract description 48
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 34
-1 carbazoyl Chemical group 0.000 claims abstract description 33
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
239000001257 hydrogen Substances 0.000 claims abstract description 25
125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
238000004519 manufacturing process Methods 0.000 claims abstract description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
150000003950 cyclic amides Chemical class 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical group 0.000 claims abstract description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
125000004423 acyloxy group Chemical group 0.000 claims abstract description 5
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 3
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 15
125000005843 halogen group Chemical group 0.000 claims abstract 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 45
239000000203 mixture Substances 0.000 claims description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 24
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 19
239000000126 substance Substances 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
150000002537 isoquinolines Chemical class 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000012024 dehydrating agents‎ Substances 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 4
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 4
229940106681 chloroacetic acid Drugs 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 3
LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
150000007944 thiolates Chemical class 0.000 claims description 3
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 2
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
230000009435 amidation Effects 0.000 claims description 2
238000007112 amidation reaction Methods 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000003573 thiols Chemical class 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 11
230000003301 hydrolyzing effect Effects 0.000 claims 9
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 8
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 3
ILROLYQPRYHHFG-UHFFFAOYSA-N 1-$l^{1}-oxidanylprop-2-en-1-one Chemical group [O]C(=O)C=C ILROLYQPRYHHFG-UHFFFAOYSA-N 0.000 claims 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims 2
239000012458 free base Substances 0.000 claims 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 2
KIEWLNQXCNMBPD-UHFFFAOYSA-N 2-(3,4-dihydroisoquinolin-1-yl)-2,2-dimethoxyacetonitrile Chemical compound COC(C#N)(C1=NCCC2=CC=CC=C12)OC KIEWLNQXCNMBPD-UHFFFAOYSA-N 0.000 claims 1
RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 claims 1
GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 claims 1
LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
150000008065 acid anhydrides Chemical class 0.000 claims 1
239000003377 acid catalyst Substances 0.000 claims 1
150000001449 anionic compounds Chemical class 0.000 claims 1
150000001767 cationic compounds Chemical class 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
229910001412 inorganic anion Inorganic materials 0.000 claims 1
229910001411 inorganic cation Inorganic materials 0.000 claims 1
238000002955 isolation Methods 0.000 claims 1
150000002891 organic anions Chemical class 0.000 claims 1
150000002892 organic cations Chemical class 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
238000010992 reflux Methods 0.000 claims 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 10
239000004480 active ingredient Substances 0.000 abstract description 7
239000003085 diluting agent Substances 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 3
239000002934 diuretic Substances 0.000 abstract description 2
230000001882 diuretic effect Effects 0.000 abstract description 2
208000001953 Hypotension Diseases 0.000 abstract 1
125000002947 alkylene group Chemical group 0.000 abstract 1
230000001088 anti-asthma Effects 0.000 abstract 1
239000002260 anti-inflammatory agent Substances 0.000 abstract 1
229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
239000000924 antiasthmatic agent Substances 0.000 abstract 1
239000002220 antihypertensive agent Substances 0.000 abstract 1
208000021822 hypotensive Diseases 0.000 abstract 1
230000001077 hypotensive effect Effects 0.000 abstract 1
229910052757 nitrogen Inorganic materials 0.000 description 41
235000013350 formula milk Nutrition 0.000 description 35
238000002844 melting Methods 0.000 description 32
230000008018 melting Effects 0.000 description 32
239000000243 solution Substances 0.000 description 14
239000000460 chlorine Substances 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 8
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000002775 capsule Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
206010030113 Oedema Diseases 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
229960000278 theophylline Drugs 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 3
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
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239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000758 substrate Substances 0.000 description 3
210000002700 urine Anatomy 0.000 description 3
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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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150000001340 alkali metals Chemical class 0.000 description 2
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235000011114 ammonium hydroxide Nutrition 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
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125000004429 atom Chemical group 0.000 description 2
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102000004190 Enzymes Human genes 0.000 description 1
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FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
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239000000443 aerosol Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
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150000004781 alginic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
DQSGVVGOPRWTKI-QVFAWCHISA-N atazanavir sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H](NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)[C@@H](O)CN(CC=1C=CC(=CC=1)C=1N=CC=CC=1)NC(=O)[C@@H](NC(=O)OC)C(C)(C)C)C1=CC=CC=C1 DQSGVVGOPRWTKI-QVFAWCHISA-N 0.000 description 1
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
235000011116 calcium hydroxide Nutrition 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000008298 dragée Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000005755 formation reaction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
QBQQKHZEHKZMJF-NXUSYKNTSA-N mioe Chemical compound C=1([C@@H]2OC(=O)C[C@@H]3[C@@]2(C)CC[C@H]2C3=C[C@@H]3[C@@H](OC(=O)C(C)C)C(C)(C)[C@@H]([C@@]2(C)C3=O)CC(=O)OC)C=COC=1 QBQQKHZEHKZMJF-NXUSYKNTSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material 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
238000002560 therapeutic procedure Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1

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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000355538A 1980-07-04 1980-07-04 Derives sulfures de l'isoquinolines; methode de preparation, et compositions pharmaceutiques qui en renferment Expired CA1144163A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000355538A CA1144163A (fr)	1980-07-04	1980-07-04	Derives sulfures de l'isoquinolines; methode de preparation, et compositions pharmaceutiques qui en renferment

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000355538A CA1144163A (fr)	1980-07-04	1980-07-04	Derives sulfures de l'isoquinolines; methode de preparation, et compositions pharmaceutiques qui en renferment

Publications (1)

Publication Number	Publication Date
CA1144163A true CA1144163A (fr)	1983-04-05

Family

ID=4117352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000355538A Expired CA1144163A (fr)	1980-07-04	1980-07-04	Derives sulfures de l'isoquinolines; methode de preparation, et compositions pharmaceutiques qui en renferment

Country Status (1)

Country	Link
CA (1)	CA1144163A (fr)

1980
- 1980-07-04 CA CA000355538A patent/CA1144163A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2000-04-05	MKEX	Expiry

Publication	Publication Date	Title
CA1087205A (fr)	1980-10-07	Acides 2-amino-3-(5-et 6-)benzoylphenylacetiques, leurs esters et sels metalliques
CA1297111C (fr)	1992-03-10	.alpha.-ALKYL-4-AMINO-3-QUINOLINEMETHANOL ET 1-(4-ARYLALKYLAMINO-3-QUINOLIMYL)ALCANONES, PROCEDE POUR LEUR PREPRARATION ET LEUR UTILISTION COMME MEDICAMENTS
PL119501B1 (en)	1982-01-30	Process for manufacturing novel,condensed pyrimidine derivatives pirimidina
US4855291A (en)	1989-08-08	1,4dihydroquinoline-3-carboxamides
EP0081756B1 (fr)	1985-05-15	Composés ayant une activité anti-inflammatoire et anti-tussive, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0190367B1 (fr)	1990-01-17	COMPOSES DE BENZO ADh BDCINNOLINE, PROCEDE DE PREPARATION DE CES COMPOSES ET COMPOSITION MEDICINALE LES CONTENANT
US4219551A (en)	1980-08-26	Aminoalkoxyphenylpyrrolidone antihypertonic agents and use thereof
US4415569A (en)	1983-11-15	Pyrazoloindazole derivatives and pharmaceutical composition containing the same
US4704391A (en)	1987-11-03	Pyridazinones, and pharmaceutical preparations thereof
IE46376B1 (en)	1983-05-18	Isoquinoline and naphthyridine substituted aminoalkoxyphenyl derivatives
CA1203801A (fr)	1986-04-29	Derives de piperazines, leur preparation et produits pharmaceutiques qui les renferment
US5084456A (en)	1992-01-28	Oxazolopyridine compounds
EP0350990B1 (fr)	1995-09-20	Dérivés de pyridazinone
US4373104A (en)	1983-02-08	Sulfur-containing isoquinoline derivatives, process for the preparation thereof and pharmaceutical compositions containing them
NO140012B (no)	1979-03-12	Analogifremgangsmaate for fremstilling av nye terapeutisk aktive derivater av naftyridin
US5973165A (en)	1999-10-26	Process for preparing 2-oxindole
US4167570A (en)	1979-09-11	2-Methyl-6-alkyl-11-aminoalkyl-6,11-dihydro-5H-pyrido(2,3-B)(1,5)benzodiazepin-5-ones and salts thereof
CA1244419A (fr)	1988-11-08	Pyridazinones substitues, procede de production, preparations pharmaceutiques contenant lesdits composes et applications
US4411907A (en)	1983-10-25	Antiinflammatory 3H-naphtho(1,2-d)imidazoles
US4136190A (en)	1979-01-23	4,4-dimethyl-3,5-pyrrolidinediones
IE46823B1 (en)	1983-10-05	Improvements in or relating to new chromene derivatives
CA1110249A (fr)	1981-10-06	Indolopyrones ayant des proprietes antiallergiques
NO136840B (no)	1977-08-08	Analogifremgangsm}te til fremstilling av nye, terapeutisk aktive derivater av isoindolin.
US4281125A (en)	1981-07-28	Quinoline catalyzed synthesis of pyridazinone pharmaceutical intermediates
JPH06511487A (ja)	1994-12-22	ベンゾ［ｂ］ナフチリジン類の製造方法