FI91410C - Menetelmä terapeuttisesti aktiivisten oktahydropyrrolo-pyratsino/2,1-i/indol-2-oni-johdannaisten valmistamiseksi - Google Patents
Menetelmä terapeuttisesti aktiivisten oktahydropyrrolo-pyratsino/2,1-i/indol-2-oni-johdannaisten valmistamiseksi Download PDFInfo
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- FI91410C FI91410C FI891807A FI891807A FI91410C FI 91410 C FI91410 C FI 91410C FI 891807 A FI891807 A FI 891807A FI 891807 A FI891807 A FI 891807A FI 91410 C FI91410 C FI 91410C
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- formula
- compound
- compounds
- indol
- pyrazino
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 230000008569 process Effects 0.000 title claims description 10
- 150000005625 indol-2-ones Chemical class 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002253 acid Substances 0.000 claims description 14
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 4
- 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 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
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- 230000000977 initiatory effect Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 241000124008 Mammalia Species 0.000 abstract description 2
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- 208000010877 cognitive disease Diseases 0.000 abstract 1
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- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
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- 239000000243 solution Substances 0.000 description 24
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- -1 strong mineral acids Chemical class 0.000 description 16
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- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- 206010012289 Dementia Diseases 0.000 description 2
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- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000002253 anti-ischaemic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 206010013932 dyslexia Diseases 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- GAKFPRCRMVJEHX-UHFFFAOYSA-N ethene ethyl 2-(2-oxocyclohexyl)acetate Chemical group CCOC(=O)CC1CCCCC1=O.C=C GAKFPRCRMVJEHX-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- FGSGHBPKHFDJOP-UHFFFAOYSA-N ethyl 2-oxocyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCCC1=O FGSGHBPKHFDJOP-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000013102 re-test Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005406 washing Methods 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18380288 | 1988-04-20 | ||
| US07/183,802 US4897399A (en) | 1988-04-20 | 1988-04-20 | Heterotertracyclic lactam derivatives, pharmaceutical compositions, and method of treating impaired memory and learning |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI891807A0 FI891807A0 (fi) | 1989-04-17 |
| FI891807A7 FI891807A7 (fi) | 1989-10-21 |
| FI91410B FI91410B (fi) | 1994-03-15 |
| FI91410C true FI91410C (fi) | 1994-06-27 |
Family
ID=22674346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI891807A FI91410C (fi) | 1988-04-20 | 1989-04-17 | Menetelmä terapeuttisesti aktiivisten oktahydropyrrolo-pyratsino/2,1-i/indol-2-oni-johdannaisten valmistamiseksi |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4897399A (OSRAM) |
| EP (1) | EP0338989B1 (OSRAM) |
| JP (1) | JPH0662620B2 (OSRAM) |
| KR (1) | KR900016204A (OSRAM) |
| AT (1) | ATE86993T1 (OSRAM) |
| AU (1) | AU624129B2 (OSRAM) |
| DD (1) | DD283823A5 (OSRAM) |
| DE (1) | DE68905363T2 (OSRAM) |
| DK (1) | DK189389A (OSRAM) |
| ES (1) | ES2046528T3 (OSRAM) |
| FI (1) | FI91410C (OSRAM) |
| GR (1) | GR3007850T3 (OSRAM) |
| HU (1) | HU203889B (OSRAM) |
| IE (1) | IE891261L (OSRAM) |
| IL (1) | IL89942A (OSRAM) |
| MX (1) | MX15697A (OSRAM) |
| NO (1) | NO168707C (OSRAM) |
| NZ (1) | NZ228779A (OSRAM) |
| PH (1) | PH26084A (OSRAM) |
| PT (1) | PT90302B (OSRAM) |
| YU (1) | YU80689A (OSRAM) |
| ZA (1) | ZA892861B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5015645A (en) * | 1989-10-19 | 1991-05-14 | Ciba-Geigy Corporation | Tetracyclic pyrrole lactam derivatives |
| EP0432099A3 (en) * | 1989-12-08 | 1992-01-08 | Ciba-Geigy Ag | Hydrogenated nitrogen containing heterocycles |
| US5204342A (en) * | 1989-12-08 | 1993-04-20 | Ciba-Geigy Corporation | Saturated tetracyclic nitrogen heterocycles |
| DE4135551A1 (de) * | 1991-08-31 | 1993-03-04 | Schering Ag | Verwendung von antagonisten oder partiellen agonisten am 5-ht1a-rezeptor zur behandlung und praevention von kognitiven stoerungen |
| JP2607032B2 (ja) * | 1993-07-16 | 1997-05-07 | 大日本印刷株式会社 | 成形同時絵付転写フィルム及びその製造方法 |
| JP3756406B2 (ja) | 1998-07-14 | 2006-03-15 | 大日本印刷株式会社 | 化粧材 |
| EP2316643A1 (en) | 2009-10-27 | 2011-05-04 | Dai Nippon Printing Co., Ltd. | Decorative sheet and decorative material laminated with the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0252643A1 (en) * | 1986-07-01 | 1988-01-13 | BEECHAM - WUELFING GmbH & Co. KG | Pyrido[1,2-a]indole derivatives, process for their preparation and pharmaceutical compounds containing them |
| US4956278A (en) * | 1988-02-23 | 1990-09-11 | Louisiana State University | Anaplasma marginale antigen, antigen compositions, vaccine and process for the production of said antigen, antigen compositions and vaccine |
| JPH10786A (ja) * | 1996-06-14 | 1998-01-06 | Brother Ind Ltd | インクジェット記録装置 |
| JP3394157B2 (ja) * | 1997-06-13 | 2003-04-07 | 神鋼パンテツク株式会社 | 有機性廃液の処理方法及びその処理装置 |
-
1988
- 1988-04-20 US US07/183,802 patent/US4897399A/en not_active Expired - Fee Related
-
1989
- 1989-04-07 AU AU32559/89A patent/AU624129B2/en not_active Ceased
- 1989-04-11 AT AT89810282T patent/ATE86993T1/de not_active IP Right Cessation
- 1989-04-11 EP EP89810282A patent/EP0338989B1/en not_active Expired - Lifetime
- 1989-04-11 DE DE8989810282T patent/DE68905363T2/de not_active Expired - Fee Related
- 1989-04-11 ES ES198989810282T patent/ES2046528T3/es not_active Expired - Lifetime
- 1989-04-13 IL IL89942A patent/IL89942A/xx unknown
- 1989-04-17 FI FI891807A patent/FI91410C/fi not_active IP Right Cessation
- 1989-04-18 MX MX1569789A patent/MX15697A/es unknown
- 1989-04-18 PT PT90302A patent/PT90302B/pt not_active IP Right Cessation
- 1989-04-18 NZ NZ228779A patent/NZ228779A/en unknown
- 1989-04-18 DD DD89327729A patent/DD283823A5/de not_active IP Right Cessation
- 1989-04-19 NO NO891608A patent/NO168707C/no unknown
- 1989-04-19 YU YU00806/89A patent/YU80689A/xx unknown
- 1989-04-19 HU HU891913A patent/HU203889B/hu not_active IP Right Cessation
- 1989-04-19 JP JP1097671A patent/JPH0662620B2/ja not_active Expired - Lifetime
- 1989-04-19 IE IE891261A patent/IE891261L/xx unknown
- 1989-04-19 ZA ZA892861A patent/ZA892861B/xx unknown
- 1989-04-19 KR KR1019890005138A patent/KR900016204A/ko not_active Ceased
- 1989-04-19 DK DK189389A patent/DK189389A/da not_active Application Discontinuation
- 1989-04-20 PH PH38544A patent/PH26084A/en unknown
-
1993
- 1993-05-14 GR GR920402945T patent/GR3007850T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT90302B (pt) | 1994-09-30 |
| GR3007850T3 (OSRAM) | 1993-08-31 |
| DK189389D0 (da) | 1989-04-19 |
| HUT50176A (en) | 1989-12-28 |
| IL89942A (en) | 1993-07-08 |
| FI891807A0 (fi) | 1989-04-17 |
| FI91410B (fi) | 1994-03-15 |
| FI891807A7 (fi) | 1989-10-21 |
| ATE86993T1 (de) | 1993-04-15 |
| IE891261L (en) | 1989-10-20 |
| NO891608D0 (no) | 1989-04-19 |
| DE68905363T2 (de) | 1993-08-05 |
| NO891608L (no) | 1989-10-23 |
| YU80689A (en) | 1991-02-28 |
| EP0338989B1 (en) | 1993-03-17 |
| MX15697A (es) | 1993-12-01 |
| PT90302A (pt) | 1989-11-10 |
| NO168707C (no) | 1992-03-25 |
| IL89942A0 (en) | 1989-12-15 |
| ZA892861B (en) | 1989-12-27 |
| PH26084A (en) | 1992-02-06 |
| NZ228779A (en) | 1991-06-25 |
| AU624129B2 (en) | 1992-06-04 |
| JPH0662620B2 (ja) | 1994-08-17 |
| NO168707B (no) | 1991-12-16 |
| ES2046528T3 (es) | 1994-02-01 |
| KR900016204A (ko) | 1990-11-12 |
| JPH0242080A (ja) | 1990-02-13 |
| EP0338989A1 (en) | 1989-10-25 |
| DE68905363D1 (de) | 1993-04-22 |
| AU3255989A (en) | 1989-10-26 |
| DD283823A5 (de) | 1990-10-24 |
| DK189389A (da) | 1989-10-21 |
| HU203889B (en) | 1991-10-28 |
| US4897399A (en) | 1990-01-30 |
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Owner name: CIBA-GEIGY AG |