JPH0660133B2 - 新規ホモプロパルギルアミン類 - Google Patents
新規ホモプロパルギルアミン類Info
- Publication number
- JPH0660133B2 JPH0660133B2 JP60263634A JP26363485A JPH0660133B2 JP H0660133 B2 JPH0660133 B2 JP H0660133B2 JP 60263634 A JP60263634 A JP 60263634A JP 26363485 A JP26363485 A JP 26363485A JP H0660133 B2 JPH0660133 B2 JP H0660133B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- phenyl
- halogen
- cycloalkyl
- 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 - Lifetime
Links
- 150000001412 amines Chemical class 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 45
- -1 Dialkylphenylsilyl Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 239000012458 free base Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229940121375 antifungal agent Drugs 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000003429 antifungal agent Substances 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 18
- 238000000034 method Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000000575 pesticide Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 241000233866 Fungi Species 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000000973 chemotherapeutic effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
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- PJEFKCZOMFPUIE-UHFFFAOYSA-N 3-(4-fluorophenyl)-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)C1=CC=C(F)C=C1 PJEFKCZOMFPUIE-UHFFFAOYSA-N 0.000 description 2
- UBKDWFWJSKMFQA-UHFFFAOYSA-N 5,5-dimethylhex-3-yn-1-ol Chemical compound CC(C)(C)C#CCCO UBKDWFWJSKMFQA-UHFFFAOYSA-N 0.000 description 2
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- 241000221535 Pucciniales Species 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000011717 all-trans-retinol Substances 0.000 description 2
- 235000019169 all-trans-retinol Nutrition 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
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- 239000000975 dye Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 2
- 229920000940 maneb Polymers 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ANJHBJOCVRLVCS-UHFFFAOYSA-N 1-(2h-chromen-4-yl)-n-methylmethanamine Chemical compound C1=CC=C2C(CNC)=CCOC2=C1 ANJHBJOCVRLVCS-UHFFFAOYSA-N 0.000 description 1
- AXLCDWYLYUOJAM-UHFFFAOYSA-N 1-fluoro-4-(2-methylbut-3-yn-2-yl)benzene Chemical compound C#CC(C)(C)C1=CC=C(F)C=C1 AXLCDWYLYUOJAM-UHFFFAOYSA-N 0.000 description 1
- PTMRDOLOEDPHLB-UHFFFAOYSA-N 2,3-dipentylphenol Chemical compound CCCCCC1=CC=CC(O)=C1CCCCC PTMRDOLOEDPHLB-UHFFFAOYSA-N 0.000 description 1
- UOEIWAZNZTXYSC-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)C1=CC=C(F)C=C1 UOEIWAZNZTXYSC-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 description 1
- BXZOITQTCSHLSH-UHFFFAOYSA-N 4-(chloromethyl)-2h-chromene Chemical compound C1=CC=C2C(CCl)=CCOC2=C1 BXZOITQTCSHLSH-UHFFFAOYSA-N 0.000 description 1
- CDIJOYCNNFLOAX-UHFFFAOYSA-N 4-(trichloromethylsulfanyl)isoindole-1,3-dione Chemical compound ClC(Cl)(Cl)SC1=CC=CC2=C1C(=O)NC2=O CDIJOYCNNFLOAX-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- DXOKCNCEDNMXGR-UHFFFAOYSA-N 5-ethyl-n-methyl-n-(naphthalen-1-ylmethyl)hept-5-en-3-yn-1-amine Chemical compound C1=CC=C2C(CN(C)CCC#CC(=CC)CC)=CC=CC2=C1 DXOKCNCEDNMXGR-UHFFFAOYSA-N 0.000 description 1
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- MJBPUQUGJNAPAZ-AWEZNQCLSA-N Butin Natural products C1([C@@H]2CC(=O)C3=CC=C(C=C3O2)O)=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-AWEZNQCLSA-N 0.000 description 1
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- 230000036571 hydration Effects 0.000 description 1
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- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 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
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- NIWNQRYVOLRIML-UHFFFAOYSA-N n,5,5-trimethyl-n-(naphthalen-1-ylmethyl)hex-3-yn-1-amine Chemical compound C1=CC=C2C(CN(CCC#CC(C)(C)C)C)=CC=CC2=C1 NIWNQRYVOLRIML-UHFFFAOYSA-N 0.000 description 1
- MQRIUFVBEVFILS-UHFFFAOYSA-N n-methyl-1-naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CNC)=CC=CC2=C1 MQRIUFVBEVFILS-UHFFFAOYSA-N 0.000 description 1
- SXYAQHNETQONLK-UHFFFAOYSA-N n-methyl-n-(naphthalen-1-ylmethyl)but-3-yn-1-amine Chemical compound C1=CC=C2C(CN(CCC#C)C)=CC=CC2=C1 SXYAQHNETQONLK-UHFFFAOYSA-N 0.000 description 1
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/04—Nitrogen directly attached to aliphatic or cycloaliphatic carbon atoms
-
- 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
- A61K31/13—Amines
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- 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
- A61K31/695—Silicon compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3442529.2 | 1984-11-22 | ||
| DE19843442529 DE3442529A1 (de) | 1984-11-22 | 1984-11-22 | Neue homopropargylaminderivate, verfahren zu ihrer herstellung und ihre verwendung |
| DE19853528736 DE3528736A1 (de) | 1985-08-10 | 1985-08-10 | Neue homopropargylaminderivate, verfahren zu ihrer herstellung und ihre verwendung |
| DE3528736.5 | 1985-08-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61137843A JPS61137843A (ja) | 1986-06-25 |
| JPH0660133B2 true JPH0660133B2 (ja) | 1994-08-10 |
Family
ID=25826721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60263634A Expired - Lifetime JPH0660133B2 (ja) | 1984-11-22 | 1985-11-21 | 新規ホモプロパルギルアミン類 |
Country Status (16)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5334628A (en) * | 1984-06-09 | 1994-08-02 | Kaken Pharmaceutical Co., Ltd. | Amine derivatives, processes for preparing the same and fungicides containing the same |
| JPS6145A (ja) * | 1984-06-09 | 1986-01-06 | Kaken Pharmaceut Co Ltd | Ｎ‐（４‐ｔｅｒｔ‐ブチルベンジル）‐Ｎ‐メチル‐１‐ナフチルメチルアミンおよびそれを有効成分とする抗真菌剤 |
| US5030625A (en) * | 1984-11-22 | 1991-07-09 | Sandoz Ltd. | Anti-fungal homopropargylamine compounds |
| JPS63230610A (ja) * | 1987-03-19 | 1988-09-27 | Kaken Pharmaceut Co Ltd | 農園芸用殺菌剤 |
| EP0363326A3 (en) * | 1988-10-07 | 1991-10-09 | Sandoz Ag | Fungicidal amines |
| US5045551A (en) * | 1989-09-19 | 1991-09-03 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
| US6743940B2 (en) | 2000-12-15 | 2004-06-01 | Ciba Specialty Chemicals Corporation | 4-aminobut-2-ynecarboxylic acid derivatives |
| EP1215198A1 (en) * | 2000-12-15 | 2002-06-19 | Ciba SC Holding AG | 4-Aminobut-2-yne carboxylic acid derivatives and their use as antimicrobial agents |
| US20060078580A1 (en) | 2004-10-08 | 2006-04-13 | Mediquest Therapeutics, Inc. | Organo-gel formulations for therapeutic applications |
| US7740875B2 (en) * | 2004-10-08 | 2010-06-22 | Mediquest Therapeutics, Inc. | Organo-gel formulations for therapeutic applications |
| CN108084125B (zh) * | 2016-11-23 | 2020-08-18 | 华东理工大学 | 苯并杂环烷基胺类化合物及其用途 |
| CN106905165B (zh) * | 2017-03-14 | 2019-07-26 | 广东药科大学 | 一种抗真菌类药物及其中间体的合成和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1468761A (fr) * | 1965-08-05 | 1967-02-10 | Amines et esters carbamiques acétyléniques | |
| JPS5941966B2 (ja) * | 1975-10-21 | 1984-10-11 | 住友化学工業株式会社 | ガイチユウボウジヨソセイブツ オヨビ ソノセイゾウホウ |
| JPS5919549B2 (ja) * | 1976-01-01 | 1984-05-07 | 武田薬品工業株式会社 | 異節環状化合物 |
| DE2609280A1 (de) * | 1976-03-04 | 1977-09-15 | Schering Ag | Schaedlingsbekaempfungsmittel |
| DE2716943C2 (de) * | 1976-04-28 | 1986-08-14 | Sandoz-Patent-GmbH, 7850 Lörrach | N-(3-Phenyl-2-propenyl)-N-(1-naphthylmethyl)-amine, ihre Verwendung und Herstellung |
| DE19375084I2 (de) * | 1979-08-22 | 2000-11-16 | Novartis Ag | Propenylamine Verfahren zu ihrer Herstellung sie enthaltende pharmazeutische Zusammensetzungen und ihre Verwendung als Arzneimittel |
| DE3218176A1 (de) * | 1982-05-14 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Jodpropargylammoniumsalze, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3405332A1 (de) * | 1984-02-15 | 1985-08-22 | Sandoz-Patent-GmbH, 7850 Lörrach | Neue allylamine, verfahren zu ihrer herstellung und ihre verwendung |
| HU207282B (en) * | 1984-05-31 | 1993-03-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing phenyl-alkyl-amine derivatives and pharmaceutical compositions containing them |
-
1985
- 1985-11-13 EP EP85810537A patent/EP0191269B1/en not_active Expired - Lifetime
- 1985-11-13 DE DE8585810537T patent/DE3582060D1/de not_active Expired - Lifetime
- 1985-11-20 DK DK536085A patent/DK536085A/da not_active Application Discontinuation
- 1985-11-20 PT PT81526A patent/PT81526B/pt not_active IP Right Cessation
- 1985-11-20 AU AU50085/85A patent/AU590229B2/en not_active Ceased
- 1985-11-20 NZ NZ214259A patent/NZ214259A/xx unknown
- 1985-11-20 HU HU854428A patent/HU203073B/hu not_active IP Right Cessation
- 1985-11-20 US US06/799,807 patent/US4684661A/en not_active Expired - Fee Related
- 1985-11-20 IL IL77106A patent/IL77106A/xx not_active IP Right Cessation
- 1985-11-20 GR GR852800A patent/GR852800B/el unknown
- 1985-11-21 CN CN85109165A patent/CN1008816B/zh not_active Expired
- 1985-11-21 ES ES549152A patent/ES8705360A1/es not_active Expired
- 1985-11-21 IE IE292285A patent/IE58623B1/en not_active IP Right Cessation
- 1985-11-21 CA CA000495876A patent/CA1276027C/en not_active Expired - Lifetime
- 1985-11-21 JP JP60263634A patent/JPH0660133B2/ja not_active Expired - Lifetime
- 1985-11-22 BR BR8505876A patent/BR8505876A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1276027C (en) | 1990-11-06 |
| EP0191269A2 (en) | 1986-08-20 |
| DK536085A (da) | 1986-05-23 |
| US4684661A (en) | 1987-08-04 |
| IE58623B1 (en) | 1993-10-20 |
| EP0191269A3 (en) | 1987-08-05 |
| AU590229B2 (en) | 1989-11-02 |
| JPS61137843A (ja) | 1986-06-25 |
| PT81526B (pt) | 1988-03-03 |
| HUT39712A (en) | 1986-10-29 |
| ES549152A0 (es) | 1987-05-01 |
| DE3582060D1 (de) | 1991-04-11 |
| ES8705360A1 (es) | 1987-05-01 |
| CN85109165A (zh) | 1986-07-16 |
| GR852800B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-03-19 |
| IL77106A0 (en) | 1986-04-29 |
| BR8505876A (pt) | 1986-08-12 |
| EP0191269B1 (en) | 1991-03-06 |
| AU5008585A (en) | 1986-05-29 |
| IE852922L (en) | 1986-05-22 |
| DK536085D0 (da) | 1985-11-20 |
| PT81526A (en) | 1985-12-01 |
| CN1008816B (zh) | 1990-07-18 |
| IL77106A (en) | 1988-12-30 |
| NZ214259A (en) | 1989-10-27 |
| HU203073B (en) | 1991-05-28 |
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