CA1054599A - Derives de l'oxathiinno (1,4) (2,3-c) pyrrole' leur preparation et les compositions qui les contiennent - Google Patents
Derives de l'oxathiinno (1,4) (2,3-c) pyrrole' leur preparation et les compositions qui les contiennentInfo
- Publication number
- CA1054599A CA1054599A CA239060A CA239060A CA1054599A CA 1054599 A CA1054599 A CA 1054599A CA 239060 A CA239060 A CA 239060A CA 239060 A CA239060 A CA 239060A CA 1054599 A CA1054599 A CA 1054599A
- Authority
- CA
- Canada
- Prior art keywords
- pyrrole
- oxathiinno
- oxo
- tetrahydro
- methyl
- Prior art date
- 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
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- 239000000203 mixture Substances 0.000 title description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 187
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 15
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 8
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 8
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims abstract description 4
- -1 atoms halogen Chemical class 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- AKGSNUOZGBDODP-UHFFFAOYSA-N piperazine-1-carbonyl chloride Chemical compound ClC(=O)N1CCNCC1 AKGSNUOZGBDODP-UHFFFAOYSA-N 0.000 claims description 3
- FBAIGEMWTOSCRU-UHFFFAOYSA-N 4-methylpiperazine-1-carbonyl chloride Chemical compound CN1CCN(C(Cl)=O)CC1 FBAIGEMWTOSCRU-UHFFFAOYSA-N 0.000 claims description 2
- 159000000011 group IA salts Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 2
- 239000003204 tranquilizing agent Substances 0.000 abstract description 2
- 230000002936 tranquilizing effect Effects 0.000 abstract description 2
- 230000001622 hypnogenic effect Effects 0.000 abstract 1
- 230000002040 relaxant effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 239000000047 product Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000011591 potassium Substances 0.000 description 9
- 229910052700 potassium Inorganic materials 0.000 description 9
- 150000008064 anhydrides Chemical class 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002198 insoluble material Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 2
- CVUUCFIVYYDLHL-UHFFFAOYSA-N 7-chloroquinolin-2-amine Chemical compound C1=CC(Cl)=CC2=NC(N)=CC=C21 CVUUCFIVYYDLHL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- RNVDIKYKJMKSEK-UHFFFAOYSA-N 1-methylpiperazine;hydrate Chemical compound O.CN1CCNCC1 RNVDIKYKJMKSEK-UHFFFAOYSA-N 0.000 description 1
- VOGBOMUONXLUTI-UHFFFAOYSA-N 2,7-dichloroquinoline Chemical compound C1=CC(Cl)=NC2=CC(Cl)=CC=C21 VOGBOMUONXLUTI-UHFFFAOYSA-N 0.000 description 1
- FSWRUYCICUXURT-UHFFFAOYSA-N 2-methyl-1,8-naphthyridine Chemical compound C1=CC=NC2=NC(C)=CC=C21 FSWRUYCICUXURT-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- YPWBPONDYDVMLX-UHFFFAOYSA-N 6-methoxypyridazin-3-amine Chemical compound COC1=CC=C(N)N=N1 YPWBPONDYDVMLX-UHFFFAOYSA-N 0.000 description 1
- 102100022749 Aminopeptidase N Human genes 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 101100421144 Danio rerio selenoo1 gene Proteins 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- 101000757160 Homo sapiens Aminopeptidase N Proteins 0.000 description 1
- 241001562081 Ikeda Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100202896 Mus musculus Selenoo gene Proteins 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- QMGVPVSNSZLJIA-FVWCLLPLSA-N Strychnine Natural products O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Inorganic materials [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 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 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 235000009991 pite Nutrition 0.000 description 1
- 244000293655 pite Species 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 206010037833 rales Diseases 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7436962A FR2290208A1 (fr) | 1974-11-07 | 1974-11-07 | Nouveaux derives de l'oxathiinno(1,4)(2,3-c)pyrrole, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054599A true CA1054599A (fr) | 1979-05-15 |
Family
ID=9144747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA239060A Expired CA1054599A (fr) | 1974-11-07 | 1975-11-05 | Derives de l'oxathiinno (1,4) (2,3-c) pyrrole' leur preparation et les compositions qui les contiennent |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4021554A (en, 2012) |
| JP (2) | JPS6029716B2 (en, 2012) |
| AR (2) | AR214045A1 (en, 2012) |
| AT (1) | AT342603B (en, 2012) |
| AU (1) | AU503381B2 (en, 2012) |
| BE (1) | BE835324A (en, 2012) |
| CA (1) | CA1054599A (en, 2012) |
| CH (2) | CH608238A5 (en, 2012) |
| CS (1) | CS191285B2 (en, 2012) |
| DD (1) | DD122541A5 (en, 2012) |
| DE (1) | DE2550163C2 (en, 2012) |
| DK (1) | DK499175A (en, 2012) |
| ES (2) | ES442442A1 (en, 2012) |
| FI (1) | FI59251C (en, 2012) |
| FR (1) | FR2290208A1 (en, 2012) |
| GB (1) | GB1466829A (en, 2012) |
| HU (1) | HU170500B (en, 2012) |
| IE (1) | IE42030B1 (en, 2012) |
| IL (1) | IL48422A (en, 2012) |
| LU (1) | LU73737A1 (en, 2012) |
| NL (1) | NL7512731A (en, 2012) |
| NO (1) | NO143534C (en, 2012) |
| OA (1) | OA05141A (en, 2012) |
| PH (1) | PH14755A (en, 2012) |
| SE (1) | SE419222B (en, 2012) |
| SU (2) | SU576949A3 (en, 2012) |
| YU (2) | YU281175A (en, 2012) |
| ZA (1) | ZA756953B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1072557A (fr) * | 1976-02-20 | 1980-02-26 | Rhone-Poulenc Industries | Derives du dithiepinno (1,4)(2,3-c) pyrrole, leur preparation et les compositions qui les contiennent |
| FR2525605A1 (fr) * | 1982-04-22 | 1983-10-28 | Rhone Poulenc Sante | Nouveaux derives du dithiinno (1,4) (2,3-c) pyrrole, leur preparation et les medicaments qui les contiennent |
| FR2607504B1 (fr) * | 1986-12-02 | 1989-01-27 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
| NZ581544A (en) * | 2007-05-31 | 2012-06-29 | Glycan Biosciences | Sulphated xylans for treatment or prophylaxis of respiratory diseases |
-
1973
- 1973-11-05 ZA ZA00756953A patent/ZA756953B/xx unknown
-
1974
- 1974-11-07 FR FR7436962A patent/FR2290208A1/fr active Granted
-
1975
- 1975-10-20 OA OA55642A patent/OA05141A/xx unknown
- 1975-10-30 NL NL7512731A patent/NL7512731A/xx not_active Application Discontinuation
- 1975-11-05 PH PH17742A patent/PH14755A/en unknown
- 1975-11-05 US US05/628,927 patent/US4021554A/en not_active Expired - Lifetime
- 1975-11-05 IL IL48422A patent/IL48422A/xx unknown
- 1975-11-05 GB GB4593675A patent/GB1466829A/en not_active Expired
- 1975-11-05 CA CA239060A patent/CA1054599A/fr not_active Expired
- 1975-11-05 HU HURO867A patent/HU170500B/hu unknown
- 1975-11-05 JP JP50132199A patent/JPS6029716B2/ja not_active Expired
- 1975-11-05 AU AU86332/75A patent/AU503381B2/en not_active Expired
- 1975-11-05 IE IE2413/75A patent/IE42030B1/en unknown
- 1975-11-05 DD DD189259A patent/DD122541A5/xx unknown
- 1975-11-06 SE SE7512476A patent/SE419222B/xx unknown
- 1975-11-06 AR AR261090A patent/AR214045A1/es active
- 1975-11-06 LU LU73737A patent/LU73737A1/xx unknown
- 1975-11-06 CH CH1437775A patent/CH608238A5/xx not_active IP Right Cessation
- 1975-11-06 DK DK499175A patent/DK499175A/da unknown
- 1975-11-06 BE BE161651A patent/BE835324A/xx not_active IP Right Cessation
- 1975-11-06 SU SU7502186405A patent/SU576949A3/ru active
- 1975-11-06 YU YU02811/75A patent/YU281175A/xx unknown
- 1975-11-06 NO NO753712A patent/NO143534C/no unknown
- 1975-11-06 CH CH782118A patent/CH608808A5/xx not_active IP Right Cessation
- 1975-11-07 CS CS757509A patent/CS191285B2/cs unknown
- 1975-11-07 FI FI753126A patent/FI59251C/fi not_active IP Right Cessation
- 1975-11-07 ES ES442442A patent/ES442442A1/es not_active Expired
- 1975-11-07 ES ES442441A patent/ES442441A1/es not_active Expired
- 1975-11-07 DE DE2550163A patent/DE2550163C2/de not_active Expired
- 1975-11-07 AT AT848575A patent/AT342603B/de not_active IP Right Cessation
-
1976
- 1976-06-21 SU SU762370948A patent/SU615860A3/ru active
- 1976-07-26 AR AR264076A patent/AR214400A1/es active
-
1982
- 1982-05-20 YU YU01080/82A patent/YU108082A/xx unknown
-
1985
- 1985-02-27 JP JP60036703A patent/JPS60222484A/ja active Granted
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