NO331272B1 - Syreaddisjonssalter av polysure basiske forbindelser samt fremgangsmate for fremstilling derav - Google Patents

Syreaddisjonssalter av polysure basiske forbindelser samt fremgangsmate for fremstilling derav Download PDF

Info

Publication number: NO331272B1
Authority: NO; Norway
Prior art keywords: acid; ylthio; ethyl; pyridyl; methyl
Prior art date: 2003-02-28

Application number

NO20054100A

Other languages

English (en)

Norwegian (no)

Other versions

NO20054100L (no

NO20054100D0 (no

Inventor

Kimiyuki Shibuya

Tadaaki Ohgiya

Takayuki Matsuda

Original Assignee

Kowa Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-02-28

Filing date

2005-09-02

Publication date

2011-11-14

2005-09-02 Application filed by Kowa Co filed Critical Kowa Co

2005-09-02 Publication of NO20054100D0 publication Critical patent/NO20054100D0/no

2005-09-22 Publication of NO20054100L publication Critical patent/NO20054100L/no

2011-11-14 Publication of NO331272B1 publication Critical patent/NO331272B1/no

Links

239000002253 acid Substances 0.000 title claims abstract description 107
150000003839 salts Chemical class 0.000 title claims abstract description 78
238000000034 method Methods 0.000 title claims abstract description 24
150000007514 bases Chemical class 0.000 title abstract description 19
238000002360 preparation method Methods 0.000 title description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 109
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 66
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 33
150000001875 compounds Chemical class 0.000 claims description 51
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 47
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 42
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
239000013078 crystal Substances 0.000 claims description 27
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 26
150000004885 piperazines Chemical class 0.000 claims description 25
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 24
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 20
VGGMTOYKEDKFLN-UHFFFAOYSA-N 2-[4-[2-(1h-benzimidazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]acetamide Chemical group CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2NC3=CC=CC=C3N=2)CC1 VGGMTOYKEDKFLN-UHFFFAOYSA-N 0.000 claims description 15
FIESYXUDBWMLRP-UHFFFAOYSA-N 2-[4-[2-(1h-benzimidazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]acetamide;hydrochloride Chemical group Cl.CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2NC3=CC=CC=C3N=2)CC1 FIESYXUDBWMLRP-UHFFFAOYSA-N 0.000 claims description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
-1 methylthio, trifluoroethoxy Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
DYXZQYKQRNTJHR-UHFFFAOYSA-N 2-[4-[2-(1,3-benzoxazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2-(2-methoxyethoxy)-6-methyl-4-(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide Chemical compound COCCOC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=CC=C3N=2)CC1 DYXZQYKQRNTJHR-UHFFFAOYSA-N 0.000 claims description 6
SZLMBHBRSADVAR-UHFFFAOYSA-N 2-[4-[2-[(5,6-difluoro-1h-benzimidazol-2-yl)sulfanyl]ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide Chemical compound FC(F)(F)COC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2NC3=CC(F)=C(F)C=C3N=2)CC1 SZLMBHBRSADVAR-UHFFFAOYSA-N 0.000 claims description 6
CMISTLFCNNXRRS-UHFFFAOYSA-N 2-[4-[2-[(5,6-difluoro-1h-benzimidazol-2-yl)sulfanyl]ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide;hydrochloride Chemical group Cl.FC(F)(F)COC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2NC3=CC(F)=C(F)C=C3N=2)CC1 CMISTLFCNNXRRS-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
ZPROUZXZOZJFTI-UHFFFAOYSA-N n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]-2-[4-[2-[[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]sulfanyl]ethyl]piperazin-1-yl]acetamide Chemical compound CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=C(C=C3N=2)C(F)(F)F)CC1 ZPROUZXZOZJFTI-UHFFFAOYSA-N 0.000 claims description 6
OATIVIRLRZWRAT-UHFFFAOYSA-N n-[6-methyl-2,4-bis(methylsulfanyl)pyridin-3-yl]-2-[4-[2-[[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]sulfanyl]ethyl]piperazin-1-yl]acetamide;hydrochloride Chemical compound Cl.CSC1=CC(C)=NC(SC)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=C(C=C3N=2)C(F)(F)F)CC1 OATIVIRLRZWRAT-UHFFFAOYSA-N 0.000 claims description 6
LIFBIPOMKGMSFM-UHFFFAOYSA-N 2-[4-[2-(1,3-benzothiazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2,6-dimethyl-4-(trifluoromethyl)pyridin-3-yl]acetamide Chemical compound CC1=NC(C)=CC(C(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2SC3=CC=CC=C3N=2)CC1 LIFBIPOMKGMSFM-UHFFFAOYSA-N 0.000 claims description 5
SRBPYSVRCCDDNI-UHFFFAOYSA-N 2-[4-[2-(1,3-benzothiazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2,6-dimethyl-4-(trifluoromethyl)pyridin-3-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.CC1=NC(C)=CC(C(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2SC3=CC=CC=C3N=2)CC1 SRBPYSVRCCDDNI-UHFFFAOYSA-N 0.000 claims description 5
ZXWDDGWHGFZRRF-UHFFFAOYSA-N 2-[4-[2-(1h-benzimidazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[6-methyl-2,4-bis(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide;dihydrochloride Chemical compound Cl.Cl.FC(F)(F)COC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2NC3=CC=CC=C3N=2)CC1 ZXWDDGWHGFZRRF-UHFFFAOYSA-N 0.000 claims description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
239000011976 maleic acid Substances 0.000 claims description 5
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 4
ODYLAJPEWLKGCS-UHFFFAOYSA-N 2-[4-[2-(1,3-benzoxazol-2-ylsulfanyl)ethyl]piperazin-1-yl]-n-[2-(2-methoxyethoxy)-6-methyl-4-(2,2,2-trifluoroethoxy)pyridin-3-yl]acetamide;hydrochloride Chemical compound Cl.COCCOC1=NC(C)=CC(OCC(F)(F)F)=C1NC(=O)CN1CCN(CCSC=2OC3=CC=CC=C3N=2)CC1 ODYLAJPEWLKGCS-UHFFFAOYSA-N 0.000 claims description 4
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
229910017604 nitric acid Inorganic materials 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 3
235000015165 citric acid Nutrition 0.000 claims description 3
235000011087 fumaric acid Nutrition 0.000 claims description 3
239000001630 malic acid Substances 0.000 claims description 3
235000011090 malic acid Nutrition 0.000 claims description 3
229940098779 methanesulfonic acid Drugs 0.000 claims description 3
239000011975 tartaric acid Substances 0.000 claims description 3
235000002906 tartaric acid Nutrition 0.000 claims description 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 2
TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims description 2
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 2
239000001263 FEMA 3042 Substances 0.000 claims description 2
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 2
235000021355 Stearic acid Nutrition 0.000 claims description 2
DSFVQIUBODXRLL-UHFFFAOYSA-N acetamide;dihydrochloride Chemical compound Cl.Cl.CC(N)=O DSFVQIUBODXRLL-UHFFFAOYSA-N 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
235000003704 aspartic acid Nutrition 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims description 2
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239000000174 gluconic acid Substances 0.000 claims description 2
235000012208 gluconic acid Nutrition 0.000 claims description 2
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239000004220 glutamic acid Substances 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
229940071870 hydroiodic acid Drugs 0.000 claims description 2
239000004310 lactic acid Substances 0.000 claims description 2
235000014655 lactic acid Nutrition 0.000 claims description 2
229960002510 mandelic acid Drugs 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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
- 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
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Diabetes (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)

NO20054100A 2003-02-28 2005-09-02 Syreaddisjonssalter av polysure basiske forbindelser samt fremgangsmate for fremstilling derav NO331272B1 (no)

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Application Number	Priority Date	Filing Date	Title
JP2003052700		2003-02-28
PCT/JP2004/002375 WO2004076441A1 (ja)	2003-02-28	2004-02-27	多酸性塩基化合物の酸付加塩の製造方法

Publications (3)

Publication Number	Publication Date
NO20054100D0 NO20054100D0 (no)	2005-09-02
NO20054100L NO20054100L (no)	2005-09-22
NO331272B1 true NO331272B1 (no)	2011-11-14

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US (2)	US7750150B2 (de)
EP (1)	EP1598346B1 (de)
JP (2)	JP4594863B2 (de)
KR (1)	KR101106127B1 (de)
CN (2)	CN1753886B (de)
AT (1)	ATE554083T1 (de)
AU (1)	AU2004215523B2 (de)
BR (1)	BRPI0407908A (de)
CA (1)	CA2516822C (de)
DK (1)	DK1598346T3 (de)
EA (1)	EA009045B1 (de)
ES (1)	ES2384517T3 (de)
IL (1)	IL170093A (de)
IS (1)	IS7978A (de)
MX (1)	MXPA05009129A (de)
MY (1)	MY140618A (de)
NO (1)	NO331272B1 (de)
NZ (1)	NZ541716A (de)
PL (1)	PL378292A1 (de)
TW (2)	TWI374136B (de)
WO (1)	WO2004076441A1 (de)

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TWI324600B (en) *	2003-07-07	2010-05-11	Kowa Co	2,4-bis (trifluoroethoxy) pyridine compound and drug containing the compound
KR20060111898A (ko)	2003-08-29	2006-10-30	교와 가부시키가이샤	지질-풍부-플라크의 안정화 방법 및 파열 예방방법
TW200619204A (en) *	2004-12-10	2006-06-16	Kowa Co	Method for reduction, stabilization and prevention of rupture of lipid rich plaque
AU2006285915B2 (en)	2005-08-30	2011-02-24	Asahi Kasei Pharma Corporation	Sulfonamide compound
US8415372B2 (en) *	2007-02-27	2013-04-09	Asahi Kasei Pharma Corporation	Sulfonamide compound
CA2679263A1 (en)	2007-02-28	2008-09-04	Asahi Kasei Pharma Corporation	Sulfonamide compound
WO2009004792A1 (ja) *	2007-07-02	2009-01-08	Asahi Kasei Pharma Corporation	スルホンアミド化合物及びその結晶
US9273209B2 (en) *	2007-11-30	2016-03-01	Braggone Oy	Siloxane polymer compositions
CN102711762A (zh) *	2009-12-29	2012-10-03	兴和株式会社	口服用固体医药组合物
WO2011081118A1 (ja) *	2009-12-29	2011-07-07	興和株式会社	経口投与用医薬組成物
US20130066075A1 (en) *	2010-05-19	2013-03-14	Kowa Company, Ltd.	Prophylactic and/or therapeutic agent for non-alcoholic steatohepatitis
WO2016205141A1 (en) *	2015-06-17	2016-12-22	Gilead Sciences, Inc.	Co-crystals, salts and solid forms of tenofovir alafenamide
JPWO2018092765A1 (ja) *	2016-11-15	2019-10-17	学校法人同志社	経鼻投与用医薬組成物

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IL112152A (en) *	1994-12-26	2000-11-21	Identa Ltd	Process and test kit for cocaine detection
US6969711B2 (en) *	1997-05-26	2005-11-29	Kowa Company, Ltd.	Cyclic diamine compounds and medicine containing the same
HUP0002294A3 (en) *	1997-05-26	2001-10-29	Kowa Co	Cyclic diamine compounds and medicines containing the same
GB9826180D0 (en) *	1998-11-30	1999-01-20	Smithkline Beecham Plc	Novel process
US20060165605A1 (en) *	2001-12-28	2006-07-27	Ye-Mon Chen	Process to regenerate fcc spent catalyst
EP1571144A4 (de) *	2002-12-12	2007-08-01	Kowa Co	Hydroxyalkylierte cyclischediaminverbindung
TWI324600B (en) *	2003-07-07	2010-05-11	Kowa Co	2,4-bis (trifluoroethoxy) pyridine compound and drug containing the compound

2004
- 2004-02-25 MY MYPI20040608A patent/MY140618A/en unknown
- 2004-02-27 JP JP2005502951A patent/JP4594863B2/ja not_active Expired - Fee Related
- 2004-02-27 AT AT04715495T patent/ATE554083T1/de active
- 2004-02-27 AU AU2004215523A patent/AU2004215523B2/en not_active Ceased
- 2004-02-27 MX MXPA05009129A patent/MXPA05009129A/es active IP Right Grant
- 2004-02-27 EP EP04715495A patent/EP1598346B1/de not_active Expired - Lifetime
- 2004-02-27 PL PL378292A patent/PL378292A1/pl not_active IP Right Cessation
- 2004-02-27 ES ES04715495T patent/ES2384517T3/es not_active Expired - Lifetime
- 2004-02-27 CN CN2004800052621A patent/CN1753886B/zh not_active Expired - Fee Related
- 2004-02-27 EA EA200501379A patent/EA009045B1/ru not_active IP Right Cessation
- 2004-02-27 DK DK04715495.0T patent/DK1598346T3/da active
- 2004-02-27 CA CA2516822A patent/CA2516822C/en not_active Expired - Fee Related
- 2004-02-27 KR KR1020057015048A patent/KR101106127B1/ko not_active Expired - Fee Related
- 2004-02-27 NZ NZ541716A patent/NZ541716A/en not_active IP Right Cessation
- 2004-02-27 WO PCT/JP2004/002375 patent/WO2004076441A1/ja not_active Ceased
- 2004-02-27 BR BRPI0407908-6A patent/BRPI0407908A/pt not_active Application Discontinuation
- 2004-02-27 CN CN201210189482.0A patent/CN102702171B/zh not_active Expired - Fee Related
- 2004-02-27 US US10/545,200 patent/US7750150B2/en not_active Expired - Fee Related
- 2004-02-27 TW TW100135167A patent/TWI374136B/zh not_active IP Right Cessation
- 2004-02-27 TW TW093105174A patent/TWI355384B/zh not_active IP Right Cessation
2005
- 2005-08-04 IL IL170093A patent/IL170093A/en not_active IP Right Cessation
- 2005-08-12 IS IS7978A patent/IS7978A/is unknown
- 2005-09-02 NO NO20054100A patent/NO331272B1/no not_active IP Right Cessation
2010
- 2010-04-16 US US12/762,111 patent/US8518936B2/en not_active Expired - Fee Related
- 2010-07-15 JP JP2010160354A patent/JP5180998B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
TWI374136B (en)	2012-10-11
CN1753886B (zh)	2012-07-18
WO2004076441A1 (ja)	2004-09-10
US20060079688A1 (en)	2006-04-13
JP4594863B2 (ja)	2010-12-08
BRPI0407908A (pt)	2006-02-14
MXPA05009129A (es)	2005-10-20
NO20054100L (no)	2005-09-22
MY140618A (en)	2009-12-31
US8518936B2 (en)	2013-08-27
CN102702171B (zh)	2014-09-10
DK1598346T3 (da)	2012-05-29
AU2004215523A1 (en)	2004-09-10
TW201202218A (en)	2012-01-16
PL378292A1 (pl)	2006-03-20
CA2516822A1 (en)	2004-09-10
ES2384517T3 (es)	2012-07-06
KR101106127B1 (ko)	2012-01-20
CN102702171A (zh)	2012-10-03
AU2004215523B2 (en)	2009-07-16
TW200504052A (en)	2005-02-01
EP1598346A4 (de)	2007-08-15
EP1598346B1 (de)	2012-04-18
TWI355384B (en)	2012-01-01
NZ541716A (en)	2007-11-30
US20100234599A1 (en)	2010-09-16
ATE554083T1 (de)	2012-05-15
JPWO2004076441A1 (ja)	2006-06-01
CA2516822C (en)	2012-09-25
JP5180998B2 (ja)	2013-04-10
US7750150B2 (en)	2010-07-06
IS7978A (is)	2005-08-12
CN1753886A (zh)	2006-03-29
EA009045B1 (ru)	2007-10-26
EP1598346A1 (de)	2005-11-23
EA200501379A1 (ru)	2006-02-24
IL170093A (en)	2012-02-29
NO20054100D0 (no)	2005-09-02
KR20050105218A (ko)	2005-11-03
JP2010235635A (ja)	2010-10-21

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