FI60396C - Nytt foerfarande foer framstaellning av terapeutiskt vaerdefulla 4-(4-piperidyliden)-4h-benso(4,5)cyklohepta(1,2-b)tiofen-10(9h)-oner - Google Patents
Nytt foerfarande foer framstaellning av terapeutiskt vaerdefulla 4-(4-piperidyliden)-4h-benso(4,5)cyklohepta(1,2-b)tiofen-10(9h)-oner Download PDFInfo
- Publication number
- FI60396C FI60396C FI89/73A FI8973A FI60396C FI 60396 C FI60396 C FI 60396C FI 89/73 A FI89/73 A FI 89/73A FI 8973 A FI8973 A FI 8973A FI 60396 C FI60396 C FI 60396C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- benzo
- cyclohepta
- thiophen
- piperidylidene
- Prior art date
Links
- -1 4-PIPERIDYLIDENE Chemical class 0.000 title claims description 11
- 230000001225 therapeutic effect Effects 0.000 title 3
- 230000015572 biosynthetic process Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000003747 Grignard reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 238000003776 cleavage reaction Methods 0.000 claims description 5
- MWWHYPORGYMFIP-UHFFFAOYSA-N cyclohepta[b]thiophen-4-one Chemical compound O=C1C=CC=CC2=C1C=CS2 MWWHYPORGYMFIP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 230000007017 scission Effects 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003500 enol ether group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- IYSYPCSSDZBWHN-UHFFFAOYSA-N Nor-ketotifen Chemical class C1=2C=CSC=2C(=O)CC2=CC=CC=C2C1=C1CCNCC1 IYSYPCSSDZBWHN-UHFFFAOYSA-N 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000012433 hydrogen halide Substances 0.000 description 4
- 229910000039 hydrogen halide Inorganic materials 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000004452 microanalysis Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 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 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 3
- 231100000820 toxicity test Toxicity 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001558 histaminolytic effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- AVEDXUCTNRSAQE-UHFFFAOYSA-N 2,2,4,7-tetramethyl-1-(4-methylphenyl)sulfonylquinoline Chemical compound C12=CC(C)=CC=C2C(C)=CC(C)(C)N1S(=O)(=O)C1=CC=C(C)C=C1 AVEDXUCTNRSAQE-UHFFFAOYSA-N 0.000 description 1
- GSFNQBFZFXUTBN-UHFFFAOYSA-N 2-chlorothiophene Chemical compound ClC1=CC=CS1 GSFNQBFZFXUTBN-UHFFFAOYSA-N 0.000 description 1
- ZXEFXSDKZSGPAG-UHFFFAOYSA-N 2-pentoxythiophene Chemical compound CCCCCOC1=CC=CS1 ZXEFXSDKZSGPAG-UHFFFAOYSA-N 0.000 description 1
- ANLJOHNBBSNMIV-UHFFFAOYSA-N 2H-cyclohepta[b]thiophene 1-oxide Chemical compound C1=CC=CC=C2S(=O)CC=C21 ANLJOHNBBSNMIV-UHFFFAOYSA-N 0.000 description 1
- JWHDENUPJBYDPO-UHFFFAOYSA-N 2h-cyclohepta[e][1]benzothiole Chemical group C1=CC=CC=C2C3=CCSC3=CC=C21 JWHDENUPJBYDPO-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 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 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NFDRFHMSWHCOMK-UHFFFAOYSA-N O[S+]1C2=CC=CC=CC2=CC1 Chemical compound O[S+]1C2=CC=CC=CC2=CC1 NFDRFHMSWHCOMK-UHFFFAOYSA-N 0.000 description 1
- AKUFYPLYKXDVAG-UHFFFAOYSA-N O[S+]1C=CC=C1 Chemical compound O[S+]1C=CC=C1 AKUFYPLYKXDVAG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010040108 Serotonin syndrome Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 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
- 150000004820 halides Chemical class 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- RSDLTJVQMXAXCA-UHFFFAOYSA-N pentoxymethylbenzene Chemical compound CCCCCOCC1=CC=CC=C1 RSDLTJVQMXAXCA-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical 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)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH98572A CH568312A5 (enrdf_load_stackoverflow) | 1972-01-24 | 1972-01-24 | |
| CH98572 | 1972-01-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI60396B FI60396B (fi) | 1981-09-30 |
| FI60396C true FI60396C (fi) | 1982-01-11 |
Family
ID=4199789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI89/73A FI60396C (fi) | 1972-01-24 | 1973-01-12 | Nytt foerfarande foer framstaellning av terapeutiskt vaerdefulla 4-(4-piperidyliden)-4h-benso(4,5)cyklohepta(1,2-b)tiofen-10(9h)-oner |
Country Status (29)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2008349239B2 (en) * | 2008-01-30 | 2012-12-06 | Nippon Zoki Pharmaceutical Co., Ltd. | Piperidine derivative |
| KR101375680B1 (ko) * | 2008-08-01 | 2014-03-19 | 니폰 조키 세야쿠 가부시키가이샤 | 아미노프로필리덴 유도체 |
| JP5083989B2 (ja) * | 2008-11-20 | 2012-11-28 | 日本臓器製薬株式会社 | ピペリジン誘導体を含有する医薬 |
| CN104817532B (zh) * | 2015-03-04 | 2017-07-25 | 浙江工业大学 | 一种10‑甲氧基‑4H‑苯并[4,5]环庚三烯[1,2‑b]噻唑‑4‑酮的制备方法 |
-
1972
- 1972-01-24 CH CH98572A patent/CH568312A5/xx not_active IP Right Cessation
-
1973
- 1973-01-12 FI FI89/73A patent/FI60396C/fi active
- 1973-01-15 SE SE7300504A patent/SE395696B/xx unknown
- 1973-01-16 NO NO185/73A patent/NO136978C/no unknown
- 1973-01-19 FR FR7301856A patent/FR2169091B1/fr not_active Expired
- 1973-01-19 NL NLAANVRAGE7300797,A patent/NL178970C/xx not_active IP Right Cessation
- 1973-01-22 RO RO7300073573A patent/RO63566A/ro unknown
- 1973-01-22 LU LU66876A patent/LU66876A1/xx unknown
- 1973-01-22 DD DD168384A patent/DD104084A5/xx unknown
- 1973-01-22 AT AT47873*#A patent/AT334897B/de not_active IP Right Cessation
- 1973-01-22 GB GB311973A patent/GB1422443A/en not_active Expired
- 1973-01-22 DE DE2366394A patent/DE2366394C1/de not_active Expired
- 1973-01-22 PL PL1973160372A patent/PL83921B1/pl unknown
- 1973-01-22 IE IE90/73A patent/IE38148B1/xx unknown
- 1973-01-22 CA CA161,801A patent/CA1006523A/en not_active Expired
- 1973-01-22 HU HUSA2446A patent/HU164966B/hu unknown
- 1973-01-22 DE DE2302970A patent/DE2302970C3/de not_active Expired
- 1973-01-22 GB GB2921475A patent/GB1422444A/en not_active Expired
- 1973-01-22 KR KR7300110A patent/KR780000049B1/ko not_active Expired
- 1973-01-22 BE BE794370D patent/BE794370A/xx not_active IP Right Cessation
- 1973-01-22 ES ES410855A patent/ES410855A1/es not_active Expired
- 1973-01-23 AU AU51378/73A patent/AU477308B2/en not_active Expired
- 1973-01-23 CS CS7300000503A patent/CS183674B2/cs unknown
- 1973-01-23 JP JP922773A patent/JPS566997B2/ja not_active Expired
- 1973-01-23 ZA ZA730494A patent/ZA73494B/xx unknown
- 1973-01-23 IL IL41374A patent/IL41374A/en unknown
- 1973-01-23 SU SU1874878A patent/SU509237A3/ru active
- 1973-01-27 AR AR246230A patent/AR202094A1/es active
- 1973-04-22 YU YU178/73A patent/YU36173B/xx unknown
-
1978
- 1978-10-04 FR FR7828336A patent/FR2401153A1/fr active Granted
-
1980
- 1980-02-29 JP JP2420780A patent/JPS55129282A/ja active Granted
- 1980-09-25 HK HK534/80A patent/HK53480A/xx unknown
- 1980-12-29 DK DK555680A patent/DK154296C/da not_active IP Right Cessation
-
1990
- 1990-10-02 DK DK238090A patent/DK161324C/da not_active IP Right Cessation
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