CS221811B2 - Method of making the new isochimoline derivatives with contents of sulphur - Google Patents
Method of making the new isochimoline derivatives with contents of sulphur Download PDFInfo
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- CS221811B2 CS221811B2 CS82941A CS94182A CS221811B2 CS 221811 B2 CS221811 B2 CS 221811B2 CS 82941 A CS82941 A CS 82941A CS 94182 A CS94182 A CS 94182A CS 221811 B2 CS221811 B2 CS 221811B2
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- Czechoslovakia
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- 238000004519 manufacturing process Methods 0.000 title claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims 3
- 239000005864 Sulphur Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
- -1 carbazoyl Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 125000004423 acyloxy group Chemical group 0.000 claims abstract 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000007944 thiolates Chemical class 0.000 claims description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- 150000001767 cationic compounds Chemical class 0.000 claims description 2
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 2
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000020335 dealkylation Effects 0.000 claims 1
- 238000006900 dealkylation reaction Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 150000002537 isoquinolines Chemical class 0.000 abstract description 5
- 150000003839 salts Chemical class 0.000 abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 239000002934 diuretic Substances 0.000 abstract description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
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- 238000004458 analytical method Methods 0.000 description 21
- 238000001953 recrystallisation Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 13
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- 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 6
- 239000002775 capsule Substances 0.000 description 6
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- CKNWJTRUFRABKE-UHFFFAOYSA-N [amino(sulfanyl)methylidene]-methylazanium;bromide Chemical compound [Br-].C[NH+]=C(N)S CKNWJTRUFRABKE-UHFFFAOYSA-N 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
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- 150000004679 hydroxides Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
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- YEGYGWAHLJOBFP-UHFFFAOYSA-N 2-(6,7-diethoxy-3,4-dihydroisoquinolin-1-yl)-2-(2-hydroxyethylsulfanyl)acetonitrile Chemical compound C1CN=C(C(SCCO)C#N)C2=C1C=C(OCC)C(OCC)=C2 YEGYGWAHLJOBFP-UHFFFAOYSA-N 0.000 description 1
- PJTJYSZHEYRJHX-UHFFFAOYSA-N 2-(6,7-diethoxy-3,4-dihydroisoquinolin-1-yl)-2-(3-hydroxypropylsulfanyl)acetonitrile Chemical compound C1CN=C(C(SCCCO)C#N)C2=C1C=C(OCC)C(OCC)=C2 PJTJYSZHEYRJHX-UHFFFAOYSA-N 0.000 description 1
- HBNPQPLUWAWNAH-UHFFFAOYSA-N 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-2-ethylsulfanylacetonitrile Chemical compound COC1=C(OC)C=C2C(C(C#N)SCC)=NCCC2=C1 HBNPQPLUWAWNAH-UHFFFAOYSA-N 0.000 description 1
- XQOCCMYWBYSROC-UHFFFAOYSA-N 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-4-(dimethylamino)-2-sulfanylbutanenitrile;hydrochloride Chemical compound Cl.C1CN=C(C(S)(CCN(C)C)C#N)C2=C1C=C(OC)C(OC)=C2 XQOCCMYWBYSROC-UHFFFAOYSA-N 0.000 description 1
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- AKBPHZLNBCXBQP-UHFFFAOYSA-N 2-[cyano-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)methyl]sulfanylacetic acid Chemical compound C1CN=C(C(SCC(O)=O)C#N)C2=C1C=C(OC)C(OC)=C2 AKBPHZLNBCXBQP-UHFFFAOYSA-N 0.000 description 1
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- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 230000002000 scavenging effect Effects 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
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 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
- 210000002784 stomach Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- 210000003437 trachea Anatomy 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 238000005303 weighing Methods 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
- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79CI1944A HU178454B (en) | 1979-07-02 | 1979-07-02 | Process for preparing new isoquinoline derivatives containing sulphur |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS221811B2 true CS221811B2 (en) | 1983-04-29 |
Family
ID=10994753
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS82941A CS221811B2 (en) | 1979-07-02 | 1980-07-02 | Method of making the new isochimoline derivatives with contents of sulphur |
| CS804727A CS221810B2 (en) | 1979-07-02 | 1980-07-02 | Method of making the new isochinoline derivatives with contanets of sulphur |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS804727A CS221810B2 (en) | 1979-07-02 | 1980-07-02 | Method of making the new isochinoline derivatives with contanets of sulphur |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4373104A (en, 2012) |
| JP (1) | JPS5649365A (en, 2012) |
| AT (1) | AT376664B (en, 2012) |
| AU (1) | AU534697B2 (en, 2012) |
| BE (1) | BE884101A (en, 2012) |
| BG (2) | BG36631A3 (en, 2012) |
| CH (1) | CH651554A5 (en, 2012) |
| CS (2) | CS221811B2 (en, 2012) |
| DD (1) | DD151751A5 (en, 2012) |
| DE (1) | DE3023717A1 (en, 2012) |
| DK (1) | DK160422C (en, 2012) |
| ES (1) | ES8105715A1 (en, 2012) |
| FI (1) | FI76324C (en, 2012) |
| FR (1) | FR2460934A1 (en, 2012) |
| GB (1) | GB2053914B (en, 2012) |
| GR (1) | GR69299B (en, 2012) |
| HU (1) | HU178454B (en, 2012) |
| IL (1) | IL60408A (en, 2012) |
| IN (1) | IN151448B (en, 2012) |
| NL (1) | NL190700C (en, 2012) |
| NO (1) | NO155539C (en, 2012) |
| PL (2) | PL124602B1 (en, 2012) |
| PT (1) | PT71472A (en, 2012) |
| SE (1) | SE455701B (en, 2012) |
| SU (2) | SU936809A3 (en, 2012) |
| YU (1) | YU170480A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| HU189764B (en) * | 1983-10-25 | 1986-07-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing 1-(bis (substituted methyl)-methyl)-isoquinoline-derivatives |
| HU189765B (en) * | 1983-10-25 | 1986-07-28 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing n-substituted 1-(bis (hydroxy-metiol)-methyl)-isoquinoline-derivatives |
| US4584379A (en) * | 1985-01-22 | 1986-04-22 | Merrell Dow Pharmaceuticals Inc. | Isoquinoline thromboxane synthetase inhibitors |
| JPS63236994A (ja) * | 1987-03-26 | 1988-10-03 | 株式会社三協精機製作所 | シ−ルド部材 |
| HU209930B (en) * | 1990-11-14 | 1994-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing of 2-mercapto-2-(1-isoquinolylidene)-acetonitrile derivatives and pharmaceutical compositions comprising them |
| DE4343683A1 (de) * | 1993-12-21 | 1995-06-22 | Boehringer Ingelheim Kg | Anellierte Dihydropyridine und deren Verwendung für die Herstellung von pharmazeutischen Zubereitungen |
| HUP0000920A3 (en) * | 2000-02-28 | 2002-03-28 | Sanofi Synthelabo | Pde4 inhibitor isoquinolinylidene derivatives, process for their preparation and medicaments containing them |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2985649A (en) * | 1959-09-17 | 1961-05-23 | Pfizer & Co C | Derivatives of thiabenzopyrrocoline, thiabenzopyridocoline and thiazepine |
| GB1145254A (en) * | 1965-03-18 | 1969-03-12 | Bristol Myers Co | Novel tetrahydroisoquinoline derivatives and a process for the preparation thereof |
| GB1127525A (en) * | 1966-04-01 | 1968-09-18 | Pfizer Ltd | Di- and tetrahydroisoquinoline derivatives |
| US3389141A (en) * | 1966-05-16 | 1968-06-18 | Bristol Myers Co | 1-beta-aryloxyethyltetrahydro-isoquinolines |
| US3389140A (en) * | 1966-05-16 | 1968-06-18 | Bristol Myers Co | 1-beta-arylaminoethyl-2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolines |
| US3455933A (en) * | 1966-11-15 | 1969-07-15 | American Home Prod | Thiazolo and thiazino isoquinoline derivatives |
| US3846432A (en) * | 1970-12-29 | 1974-11-05 | Fujisawa Pharmaceutical Co | Derivatives of 1,2,3,4-tetrahydroisoquinoline |
| JPS5516138B2 (en, 2012) * | 1971-11-17 | 1980-04-30 | ||
| AT333763B (de) * | 1972-06-20 | 1976-12-10 | Fujisawa Pharmaceutical Co | Verfahren zur herstellung von neuen 1,2,3,4-tetrahydroisochinolinen und deren salzen |
| HU170680B (en, 2012) * | 1973-05-30 | 1977-08-28 | ||
| AT351540B (de) * | 1974-07-17 | 1979-07-25 | Fujisawa Pharmaceutical Co | Verfahren zur herstellung von neuen tetrahydro- isochinolinderivaten und deren salzen |
-
1979
- 1979-07-02 HU HU79CI1944A patent/HU178454B/hu not_active IP Right Cessation
-
1980
- 1980-06-25 DE DE19803023717 patent/DE3023717A1/de active Granted
- 1980-06-26 IL IL60408A patent/IL60408A/xx not_active IP Right Cessation
- 1980-06-26 AT AT0334880A patent/AT376664B/de not_active IP Right Cessation
- 1980-06-30 PT PT71472A patent/PT71472A/pt not_active IP Right Cessation
- 1980-06-30 IN IN753/CAL/80A patent/IN151448B/en unknown
- 1980-07-01 GB GB8021506A patent/GB2053914B/en not_active Expired
- 1980-07-01 SE SE8004869A patent/SE455701B/sv not_active IP Right Cessation
- 1980-07-01 SU SU802942303A patent/SU936809A3/ru active
- 1980-07-01 FR FR8014645A patent/FR2460934A1/fr active Granted
- 1980-07-01 PL PL1980225380A patent/PL124602B1/pl unknown
- 1980-07-01 BG BG048347A patent/BG36631A3/xx unknown
- 1980-07-01 GR GR62324A patent/GR69299B/el unknown
- 1980-07-01 BG BG062873A patent/BG36934A3/xx unknown
- 1980-07-01 DK DK284880A patent/DK160422C/da not_active IP Right Cessation
- 1980-07-01 CH CH5069/80A patent/CH651554A5/de not_active IP Right Cessation
- 1980-07-01 YU YU01704/80A patent/YU170480A/xx unknown
- 1980-07-01 PL PL1980230938A patent/PL126804B1/pl unknown
- 1980-07-01 FI FI802093A patent/FI76324C/fi not_active IP Right Cessation
- 1980-07-01 DD DD80222310A patent/DD151751A5/de not_active IP Right Cessation
- 1980-07-01 US US06/164,939 patent/US4373104A/en not_active Ceased
- 1980-07-01 BE BE0/201252A patent/BE884101A/fr not_active IP Right Cessation
- 1980-07-01 NL NL8003803A patent/NL190700C/xx not_active IP Right Cessation
- 1980-07-01 NO NO801982A patent/NO155539C/no unknown
- 1980-07-01 AU AU60001/80A patent/AU534697B2/en not_active Ceased
- 1980-07-02 JP JP8928180A patent/JPS5649365A/ja active Granted
- 1980-07-02 CS CS82941A patent/CS221811B2/cs unknown
- 1980-07-02 CS CS804727A patent/CS221810B2/cs unknown
- 1980-07-02 ES ES493569A patent/ES8105715A1/es not_active Expired
-
1981
- 1981-05-15 SU SU813282447A patent/SU1047389A3/ru active
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