JPS603060B2 - 有機化合物の製造方法 - Google Patents

有機化合物の製造方法

Info

Publication number: JPS603060B2
Authority: JP; Japan
Prior art keywords: formula; group; compound; formulas; tables
Prior art date: 1973-10-04
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

Application number

JP49114632A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5062979A (fr

Inventor

マツクホ−ルチヤ−ルス

ジ− シヨンソンハ−バ−ト

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn 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.)

1973-10-04

Filing date

1974-10-04

Publication date

1985-01-25

1974-10-04 Application filed by Upjohn Co filed Critical Upjohn Co

1975-05-29 Publication of JPS5062979A publication Critical patent/JPS5062979A/ja

1985-01-25 Publication of JPS603060B2 publication Critical patent/JPS603060B2/ja

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
150000002894 organic compounds Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 51
-1 amine cation Chemical class 0.000 claims description 23
OWCAKKIRPJUQFO-UHFFFAOYSA-N (2-methyl-2-nonyl-1,3-dioxolan-4-yl)methyl carbamate Chemical compound CCCCCCCCCC1(C)OCC(COC(N)=O)O1 OWCAKKIRPJUQFO-UHFFFAOYSA-N 0.000 claims description 11
229950001656 dioxamate Drugs 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
239000000126 substance Substances 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 9
239000002184 metal Substances 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
150000002431 hydrogen Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
125000002346 iodo group Chemical group I* 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
239000004071 soot Substances 0.000 claims 2
150000001768 cations Chemical class 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 description 27
239000002253 acid Substances 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
150000003839 salts Chemical class 0.000 description 14
239000003826 tablet Substances 0.000 description 13
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000000843 powder Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 12
239000002552 dosage form Substances 0.000 description 11
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
ZGBIXLDBKKUPQJ-UHFFFAOYSA-N 2-[[6-(oxaloamino)pyridin-2-yl]amino]-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=CC(NC(=O)C(O)=O)=N1 ZGBIXLDBKKUPQJ-UHFFFAOYSA-N 0.000 description 8
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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238000010561 standard procedure Methods 0.000 description 5
GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 4
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206010002198 Anaphylactic reaction Diseases 0.000 description 4
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206010020751 Hypersensitivity Diseases 0.000 description 4
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230000036783 anaphylactic response Effects 0.000 description 4
239000012736 aqueous medium Substances 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
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239000000463 material Substances 0.000 description 4
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239000003921 oil Substances 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
RBUSDTTZLFXFQJ-UHFFFAOYSA-N 2-[[6-(oxaloamino)pyridin-3-yl]amino]-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=C(NC(=O)C(O)=O)N=C1 RBUSDTTZLFXFQJ-UHFFFAOYSA-N 0.000 description 3
235000019739 Dicalciumphosphate Nutrition 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
208000026935 allergic disease Diseases 0.000 description 3
230000000172 allergic effect Effects 0.000 description 3
230000007815 allergy Effects 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
208000010668 atopic eczema Diseases 0.000 description 3
239000001506 calcium phosphate Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 3
229940038472 dicalcium phosphate Drugs 0.000 description 3
229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000003937 drug carrier Substances 0.000 description 3
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238000011049 filling Methods 0.000 description 3
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239000008101 lactose Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000006199 nebulizer Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000008024 pharmaceutical diluent Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
244000215068 Acacia senegal Species 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 2
RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
208000004262 Food Hypersensitivity Diseases 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
229920000084 Gum arabic Polymers 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000000205 acacia gum Substances 0.000 description 2
235000010489 acacia gum Nutrition 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
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150000001408 amides Chemical class 0.000 description 2
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239000000427 antigen Substances 0.000 description 2
102000036639 antigens Human genes 0.000 description 2
108091007433 antigens Proteins 0.000 description 2
238000003556 assay Methods 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000020932 food allergy Nutrition 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
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238000010438 heat treatment Methods 0.000 description 2
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150000002500 ions Chemical group 0.000 description 2
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235000012054 meals Nutrition 0.000 description 2
239000002609 medium Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
210000003928 nasal cavity Anatomy 0.000 description 2
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230000003000 nontoxic effect Effects 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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DRDCQJADRSJFFD-UHFFFAOYSA-N tris-hydroxymethyl-methyl-ammonium Chemical class OC[N+](C)(CO)CO DRDCQJADRSJFFD-UHFFFAOYSA-N 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
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MAKFMOSBBNKPMS-UHFFFAOYSA-N 2,3-dichloropyridine Chemical compound ClC1=CC=CN=C1Cl MAKFMOSBBNKPMS-UHFFFAOYSA-N 0.000 description 1
LIHUFKFFORDAGE-UHFFFAOYSA-N 2-[[2,6-dimethoxy-5-(oxaloamino)pyridin-3-yl]amino]-2-oxoacetic acid Chemical compound COC1=NC(OC)=C(NC(=O)C(O)=O)C=C1NC(=O)C(O)=O LIHUFKFFORDAGE-UHFFFAOYSA-N 0.000 description 1
229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 1
VYCKLWQJSVKFGP-UHFFFAOYSA-N 3,4-dinitropyridine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC([N+]([O-])=O)=C1[N+]([O-])=O VYCKLWQJSVKFGP-UHFFFAOYSA-N 0.000 description 1
ZBSBQLIPDYUJOJ-UHFFFAOYSA-N 4-methoxypyridine-2,6-diamine Chemical compound COC1=CC(N)=NC(N)=C1 ZBSBQLIPDYUJOJ-UHFFFAOYSA-N 0.000 description 1
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239000011149 active material Substances 0.000 description 1
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CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
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CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
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229910052791 calcium Inorganic materials 0.000 description 1
235000020226 cashew nut Nutrition 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
CCZOANFFMASREE-UHFFFAOYSA-N cyclohexane;sulfamic acid Chemical compound NS(O)(=O)=O.C1CCCCC1 CCZOANFFMASREE-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
229940099364 dichlorofluoromethane Drugs 0.000 description 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229960003699 evans blue Drugs 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
229960005015 local anesthetics Drugs 0.000 description 1
239000008176 lyophilized powder Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
229960002216 methylparaben Drugs 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000003595 mist Substances 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940092253 ovalbumin Drugs 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 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
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pulmonology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP49114632A 1973-10-04 1974-10-04 有機化合物の製造方法 Expired JPS603060B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US40367773A	1973-10-04	1973-10-04
US403677		1973-10-04

Publications (2)

Publication Number	Publication Date
JPS5062979A JPS5062979A (fr)	1975-05-29
JPS603060B2 true JPS603060B2 (ja)	1985-01-25

Family

ID=23596609

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP49114632A Expired JPS603060B2 (ja)	1973-10-04	1974-10-04	有機化合物の製造方法

Country Status (9)

Country	Link
JP (1)	JPS603060B2 (fr)
BE (1)	BE820723A (fr)
CA (1)	CA1041100A (fr)
CH (1)	CH605767A5 (fr)
DE (1)	DE2445002C2 (fr)
FR (1)	FR2247237B1 (fr)
GB (1)	GB1436304A (fr)
NL (1)	NL179110C (fr)
ZA (1)	ZA745754B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3132885A1 (de) *	1981-08-20	1983-03-03	Wella Ag	Mittel und verfahren zur faerbung von haaren
DE3229539A1 (de) *	1982-08-07	1984-02-09	Basf Ag, 6700 Ludwigshafen	Neue oxamidsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel
US5082467A (en) *	1990-02-08	1992-01-21	Kao Corporation	Dye composition for keratinous fibers
AU4189296A (en) *	1994-12-20	1996-07-10	Terumo Kabushiki Kaisha	Pyridylalkyl phenyl sulfone derivatives and medicinal preparation containing the same

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH531000A (de) *	1970-03-11	1972-11-30	Sandoz Ag	Verfahren zur Herstellung neuer Benzocycloheptathiophene
BE789822A (fr) *	1971-10-08	1973-04-06	Allen & Hanburys Ltd	Nouveaux composes heterocycliques

1974
- 1974-08-20 CA CA207,416A patent/CA1041100A/fr not_active Expired
- 1974-08-28 GB GB3753374A patent/GB1436304A/en not_active Expired
- 1974-09-10 ZA ZA00745754A patent/ZA745754B/xx unknown
- 1974-09-20 DE DE2445002A patent/DE2445002C2/de not_active Expired
- 1974-09-23 CH CH1282474A patent/CH605767A5/xx not_active IP Right Cessation
- 1974-10-03 NL NLAANVRAGE7413053,A patent/NL179110C/xx not_active IP Right Cessation
- 1974-10-03 FR FR7433394A patent/FR2247237B1/fr not_active Expired
- 1974-10-04 JP JP49114632A patent/JPS603060B2/ja not_active Expired
- 1974-10-04 BE BE149229A patent/BE820723A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
NL179110B (nl)	1986-02-17
CH605767A5 (fr)	1978-10-13
CA1041100A (fr)	1978-10-24
DE2445002A1 (de)	1975-04-10
JPS5062979A (fr)	1975-05-29
NL179110C (nl)	1986-07-16
BE820723A (fr)	1975-04-04
DE2445002C2 (de)	1984-11-22
ZA745754B (en)	1975-10-29
NL7413053A (nl)	1975-04-08
GB1436304A (en)	1976-05-19
FR2247237B1 (fr)	1978-07-21
FR2247237A1 (fr)	1975-05-09

Publication	Publication Date	Title
US3993679A (en)	1976-11-23	Cyano phenylene dioxamic molecules
US2910488A (en)	1959-10-27	Aniline derivatives
JPS5831350B2 (ja)	1983-07-05	キナゾロン誘導体
US4128570A (en)	1978-12-05	Anti-allergic oxanil compounds
DE2509457A1 (de)	1975-09-18	Oxaminderivate, ein verfahren zu ihrer herstellung sowie arzneimittel
US4095028A (en)	1978-06-13	Substituted dioxamic acid esters
US4091011A (en)	1978-05-23	3-Cyano-oxanilic acid derivatives
US3852324A (en)	1974-12-03	N,n-(cyano-phenylene) dioxamic acids
CA1118781A (fr)	1982-02-23	Acides 2-benzothiazolyl-oxamiques et leurs esters
JPS603060B2 (ja)	1985-01-25	有機化合物の製造方法
JPS5829309B2 (ja)	1983-06-22	コウアレルギ−セイサンカンシキカゴウブツノセイゾウホウホウ
JPS59176276A (ja)	1984-10-05	（１ｈ−テトラゾ−ル−５−イル）−２（１ｈ）キノリノン類
US4159278A (en)	1979-06-26	Dioxamic acids and salts
CA1058208A (fr)	1979-07-10	Derives d'acide n,n'(phenylphenylene) dioxamique a proprietes pharmaceutiques
US4044148A (en)	1977-08-23	Compounds, compositions and methods of use
US4119783A (en)	1978-10-10	3'Lower alkylcarbonyl oxanilic acid esters
US3972911A (en)	1976-08-03	N,N'(Cyano-phenylene)dioxamic acids and esters
US4169153A (en)	1979-09-25	Anti-allergic oxanilates
US3496186A (en)	1970-02-17	2-aminomethyl benzofuran derivatives
DE2525250A1 (de)	1975-12-18	Oxaminsaeurederivate, verfahren zu deren herstellung sowie arzneimittel
US4038398A (en)	1977-07-26	Compounds, compositions and methods of use
US4186127A (en)	1980-01-29	N-Hetero substituted dioxamic acid compounds
US3953598A (en)	1976-04-27	Compounds, compositions and methods of use
FI60864B (fi)	1981-12-31	Foerfarande foer framstaellning av nya foer behandling av allergisjukdomar laempliga substituerade 2h-pyran-2,6(3h)-dionderivat
US4281151A (en)	1981-07-28	Phenylene dioxamate esters