DE2426653C3 - Derivate des 2-Amino-1,3-thiazins - Google Patents
Derivate des 2-Amino-1,3-thiazinsInfo
- Publication number
- DE2426653C3 DE2426653C3 DE2426653A DE2426653A DE2426653C3 DE 2426653 C3 DE2426653 C3 DE 2426653C3 DE 2426653 A DE2426653 A DE 2426653A DE 2426653 A DE2426653 A DE 2426653A DE 2426653 C3 DE2426653 C3 DE 2426653C3
- Authority
- DE
- Germany
- Prior art keywords
- thiazine
- amino
- phenyl
- methylphenyl
- weight
- 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
- QKFOHTNLZOIEHZ-UHFFFAOYSA-N 2h-1,3-thiazin-2-amine Chemical class NC1SC=CC=N1 QKFOHTNLZOIEHZ-UHFFFAOYSA-N 0.000 title claims 2
- MSTFRUQNYRRUKZ-UHFFFAOYSA-N 5,6-dihydro-2h-thiazine Chemical compound C1CC=CNS1 MSTFRUQNYRRUKZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- MFPPVWVNLMINHH-UHFFFAOYSA-N 4-phenyl-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2C=CC=CC=2)=N1 MFPPVWVNLMINHH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000004480 active ingredient Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 239000002904 solvent Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- -1 tert-butylamyl Chemical group 0.000 description 13
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
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- 238000001953 recrystallisation Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
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- NTOBJLRLELCCPJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2C=CC(Cl)=CC=2)=N1 NTOBJLRLELCCPJ-UHFFFAOYSA-N 0.000 description 3
- ULOUJZDTBMCSHG-UHFFFAOYSA-N 4-naphthalen-1-yl-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2C3=CC=CC=C3C=CC=2)=N1 ULOUJZDTBMCSHG-UHFFFAOYSA-N 0.000 description 3
- LZRSVSKSQCLAMV-UHFFFAOYSA-N 4-thiophen-2-yl-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2SC=CC=2)=N1 LZRSVSKSQCLAMV-UHFFFAOYSA-N 0.000 description 3
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- XGHYAFHQCSCJTD-UHFFFAOYSA-N n-methyl-4-(4-methylphenyl)-2h-1,3-thiazin-2-amine Chemical compound CNC1SC=CC(C=2C=CC(C)=CC=2)=N1 XGHYAFHQCSCJTD-UHFFFAOYSA-N 0.000 description 3
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- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 229960002447 thiram Drugs 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VAPHYEWCMFDPRS-UHFFFAOYSA-N 3,4-dihydro-2h-1,3-thiazin-2-ol Chemical compound OC1NCC=CS1 VAPHYEWCMFDPRS-UHFFFAOYSA-N 0.000 description 2
- YUXIFYIEACQTAL-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2h-1,3-thiazin-2-amine Chemical compound NC1SC=CC(C=2C(=CC(Cl)=CC=2)Cl)=N1 YUXIFYIEACQTAL-UHFFFAOYSA-N 0.000 description 2
- RRUUBVVPYHBZNU-UHFFFAOYSA-N 4-(4-methylphenyl)-2h-1,3-thiazin-2-amine Chemical compound C1=CC(C)=CC=C1C1=NC(N)SC=C1 RRUUBVVPYHBZNU-UHFFFAOYSA-N 0.000 description 2
- CLFJKYRVYLRSBF-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)-2h-1,3-thiazin-2-amine Chemical compound C1=CC(C(C)C)=CC=C1C1=NC(N)SC=C1 CLFJKYRVYLRSBF-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- 238000009835 boiling Methods 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
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- DQDQVXZKKNNTMD-UHFFFAOYSA-N 4-(4-methylphenyl)-n-phenyl-2h-1,3-thiazin-2-amine Chemical compound C1=CC(C)=CC=C1C(C=CS1)=NC1NC1=CC=CC=C1 DQDQVXZKKNNTMD-UHFFFAOYSA-N 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lubricants (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Artificial Filaments (AREA)
- Paper (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2426653A DE2426653C3 (de) | 1974-06-01 | 1974-06-01 | Derivate des 2-Amino-1,3-thiazins |
| GB1962675A GB1452448A (en) | 1974-06-01 | 1975-05-09 | Derivatives of 2-amino-1,3-thiazine |
| NO751760A NO751760L (enExample) | 1974-06-01 | 1975-05-16 | |
| IL47373A IL47373A (en) | 1974-06-01 | 1975-05-28 | Derivatives of 4-substituted 2-amino-6h-1,3-thiazine their preparation and fungicidal or bactericidal compositions containing them |
| US05/581,526 US4049807A (en) | 1974-06-01 | 1975-05-28 | 2-Amino-1,3-thiazines their use and preparation |
| JP50063556A JPS5913516B2 (ja) | 1974-06-01 | 1975-05-29 | 新規２−アミノ−１，３−チアジン類の製造方法 |
| SE7506150A SE7506150L (sv) | 1974-06-01 | 1975-05-29 | Nya derivat av 2-amino-1,3-tiazin till anvendning som fungicider och baktericider inom vextskydd |
| FI751581A FI751581A7 (enExample) | 1974-06-01 | 1975-05-29 | |
| BE156844A BE829654A (fr) | 1974-06-01 | 1975-05-29 | Nouveaux derives de la 2-amino-1,3-thiazine |
| FR7516899A FR2275466A1 (fr) | 1974-06-01 | 1975-05-30 | Nouveaux derives de la 2-amino-1,3-thiazine et leur utilisation comme antifongicides et bactericides pour la protection des plantes et des materiaux |
| LU72620A LU72620A1 (enExample) | 1974-06-01 | 1975-05-30 | |
| DK244775A DK244775A (da) | 1974-06-01 | 1975-05-30 | Derivater af 2-amino-1,3-thiazin, deres fremstilling og anvendelse |
| NL7506472.A NL163511C (nl) | 1974-06-01 | 1975-05-30 | Werkwijze voor het bereiden van 2-amino-1,3- -thiazinen, werkwijze voor het bereiden van tegen micro-organismen werkzame preparaten, alsmede werkwijze voor het beschermen van plantaardig, levenloos dierlijk en industrieel materiaal. |
| BR4366/75D BR7503410A (pt) | 1974-06-01 | 1975-05-30 | Processo para a preparacao de novos derivados da 2-amino-1,3-tiazina |
| IE1208/75A IE41151B1 (en) | 1974-06-01 | 1975-05-30 | New derivatives of 2-amino-1,3-thiazine |
| ES438044A ES438044A1 (es) | 1974-06-01 | 1975-05-30 | Procedimiento para preparar 2-amino-1, 3-tiazinas. |
| AT411875A AT344447B (de) | 1974-06-01 | 1975-05-30 | Mittel fuer den pflanzenschutz |
| CH700775A CH576968A5 (enExample) | 1974-06-01 | 1975-05-30 | |
| IT49840/75A IT1040613B (it) | 1974-06-01 | 1975-05-30 | Derivati di 2 ammino 1 3 tiazina e procedimento per la loro produzione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2426653A DE2426653C3 (de) | 1974-06-01 | 1974-06-01 | Derivate des 2-Amino-1,3-thiazins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2426653A1 DE2426653A1 (de) | 1975-12-04 |
| DE2426653B2 DE2426653B2 (de) | 1981-07-02 |
| DE2426653C3 true DE2426653C3 (de) | 1982-05-06 |
Family
ID=5917110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2426653A Expired DE2426653C3 (de) | 1974-06-01 | 1974-06-01 | Derivate des 2-Amino-1,3-thiazins |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4049807A (enExample) |
| JP (1) | JPS5913516B2 (enExample) |
| AT (1) | AT344447B (enExample) |
| BE (1) | BE829654A (enExample) |
| BR (1) | BR7503410A (enExample) |
| CH (1) | CH576968A5 (enExample) |
| DE (1) | DE2426653C3 (enExample) |
| DK (1) | DK244775A (enExample) |
| ES (1) | ES438044A1 (enExample) |
| FI (1) | FI751581A7 (enExample) |
| FR (1) | FR2275466A1 (enExample) |
| GB (1) | GB1452448A (enExample) |
| IE (1) | IE41151B1 (enExample) |
| IL (1) | IL47373A (enExample) |
| IT (1) | IT1040613B (enExample) |
| LU (1) | LU72620A1 (enExample) |
| NL (1) | NL163511C (enExample) |
| NO (1) | NO751760L (enExample) |
| SE (1) | SE7506150L (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4210545A (en) * | 1979-03-30 | 1980-07-01 | Standard Oil Company (Indiana) | Oxidation resistant lubricant composition |
| US8173642B2 (en) | 2005-10-25 | 2012-05-08 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivatives |
| EP2151435A4 (en) | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| MX2009011498A (es) | 2007-04-24 | 2009-11-10 | Shionogi & Co | Derivados de aminodihidrotiazina sustituida con un grupo ciclico. |
| KR101324426B1 (ko) | 2008-06-13 | 2013-10-31 | 시오노기세야쿠 가부시키가이샤 | β 세크레타제 저해 작용을 갖는 황 함유 복소환 유도체 |
| RU2012129168A (ru) | 2009-12-11 | 2014-01-20 | Сионоги Энд Ко. Лтд. | Производные оксазина |
| JP5766198B2 (ja) | 2010-10-29 | 2015-08-19 | 塩野義製薬株式会社 | 縮合アミノジヒドロピリミジン誘導体 |
| CN103261199A (zh) | 2010-10-29 | 2013-08-21 | 盐野义制药株式会社 | 萘啶衍生物 |
| JPWO2012147763A1 (ja) | 2011-04-26 | 2014-07-28 | 塩野義製薬株式会社 | オキサジン誘導体およびそれを含有するｂａｃｅ１阻害剤 |
| JP2016501827A (ja) | 2012-10-24 | 2016-01-21 | 塩野義製薬株式会社 | Ｂａｃｅ１阻害作用を有するジヒドロオキサジンまたはオキサゼピン誘導体 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3228935A (en) * | 1966-01-11 | Novel z-phenylamino-xh-s,g-dihydro-i,j- thiazine derivatives | ||
| DE1159953B (de) * | 1960-07-23 | 1963-12-27 | Albert Ag Chem Werke | Verfahren zur Herstellung von 2-Imino-1, 2, 3, 6-tetrahydro-1, 3-thiazinderivaten |
-
1974
- 1974-06-01 DE DE2426653A patent/DE2426653C3/de not_active Expired
-
1975
- 1975-05-09 GB GB1962675A patent/GB1452448A/en not_active Expired
- 1975-05-16 NO NO751760A patent/NO751760L/no unknown
- 1975-05-28 IL IL47373A patent/IL47373A/en unknown
- 1975-05-28 US US05/581,526 patent/US4049807A/en not_active Expired - Lifetime
- 1975-05-29 SE SE7506150A patent/SE7506150L/xx unknown
- 1975-05-29 JP JP50063556A patent/JPS5913516B2/ja not_active Expired
- 1975-05-29 FI FI751581A patent/FI751581A7/fi not_active Application Discontinuation
- 1975-05-29 BE BE156844A patent/BE829654A/xx unknown
- 1975-05-30 NL NL7506472.A patent/NL163511C/xx not_active IP Right Cessation
- 1975-05-30 DK DK244775A patent/DK244775A/da unknown
- 1975-05-30 IT IT49840/75A patent/IT1040613B/it active
- 1975-05-30 CH CH700775A patent/CH576968A5/xx not_active IP Right Cessation
- 1975-05-30 IE IE1208/75A patent/IE41151B1/xx unknown
- 1975-05-30 LU LU72620A patent/LU72620A1/xx unknown
- 1975-05-30 BR BR4366/75D patent/BR7503410A/pt unknown
- 1975-05-30 FR FR7516899A patent/FR2275466A1/fr active Granted
- 1975-05-30 AT AT411875A patent/AT344447B/de not_active IP Right Cessation
- 1975-05-30 ES ES438044A patent/ES438044A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2426653A1 (de) | 1975-12-04 |
| ATA411875A (de) | 1977-11-15 |
| CH576968A5 (enExample) | 1976-06-30 |
| IE41151B1 (en) | 1979-10-24 |
| NL163511B (nl) | 1980-04-15 |
| NO751760L (enExample) | 1975-12-02 |
| DK244775A (da) | 1975-12-02 |
| GB1452448A (en) | 1976-10-13 |
| DE2426653B2 (de) | 1981-07-02 |
| NL7506472A (nl) | 1975-12-03 |
| JPS5913516B2 (ja) | 1984-03-30 |
| AT344447B (de) | 1978-07-25 |
| SE7506150L (sv) | 1975-12-02 |
| IL47373A0 (en) | 1975-07-28 |
| LU72620A1 (enExample) | 1976-03-17 |
| ES438044A1 (es) | 1977-01-16 |
| IE41151L (en) | 1975-12-01 |
| FR2275466A1 (fr) | 1976-01-16 |
| FR2275466B1 (enExample) | 1979-01-19 |
| NL163511C (nl) | 1980-09-15 |
| JPS511482A (en) | 1976-01-08 |
| IT1040613B (it) | 1979-12-20 |
| US4049807A (en) | 1977-09-20 |
| FI751581A7 (enExample) | 1975-12-02 |
| BR7503410A (pt) | 1976-05-25 |
| BE829654A (fr) | 1975-12-01 |
| IL47373A (en) | 1977-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |