JPS6011448A - アミノカルボン酸誘導体のｎ−アミノ化によるヒドラジノカルボン酸誘導体の製造法 - Google Patents

アミノカルボン酸誘導体のｎ−アミノ化によるヒドラジノカルボン酸誘導体の製造法

Info

Publication number: JPS6011448A
Authority: JP; Japan
Prior art keywords: acid; amino; dihydroxybenzyl; acid derivative; dimethoxybenzyl
Prior art date: 1982-08-09
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.): Pending

Application number

JP58144524A

Other languages

English (en)

Japanese (ja)

Inventor

エルンスト・シユミツト

ジ−クフリ−ト・アンドレ−

ジ−クフリ−ト・シユラム

フランク−ミヒヤエル・アルベルト

デイ−タ−・ロ−マン

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.)

Teva GmbH

Original Assignee

Arzneimittelwerk Dresden GmbH

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.)

1982-08-09

Filing date

1983-08-09

Publication date

1985-01-21

1983-08-09 Application filed by Arzneimittelwerk Dresden GmbH filed Critical Arzneimittelwerk Dresden GmbH

1985-01-21 Publication of JPS6011448A publication Critical patent/JPS6011448A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 12
238000005576 amination reaction Methods 0.000 title description 6
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title 1
OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
230000008569 process Effects 0.000 claims description 12
235000019260 propionic acid Nutrition 0.000 claims description 12
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
-1 boric acid compound Chemical class 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 11
239000000284 extract Substances 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 7
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
230000001681 protective effect Effects 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000003862 amino acid derivatives Chemical class 0.000 claims description 3
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
235000010338 boric acid Nutrition 0.000 claims description 3
229960002645 boric acid Drugs 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
238000000605 extraction Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
238000000926 separation method Methods 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
238000004821 distillation Methods 0.000 claims description 2
239000003444 phase transfer catalyst Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 3
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 2
239000003513 alkali Substances 0.000 claims 2
230000002051 biphasic effect Effects 0.000 claims 1
239000004327 boric acid Substances 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
238000010992 reflux Methods 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
239000011877 solvent mixture Substances 0.000 claims 1
239000000047 product Substances 0.000 description 24
238000002844 melting Methods 0.000 description 17
230000008018 melting Effects 0.000 description 16
239000000243 solution Substances 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000000354 decomposition reaction Methods 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
235000001014 amino acid Nutrition 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
150000004682 monohydrates Chemical class 0.000 description 5
239000002994 raw material Substances 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
150000001450 anions Chemical group 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000007789 gas Substances 0.000 description 4
DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FYWDUQCSMYWUHV-UHFFFAOYSA-N 3-chloro-5-hydroxypentan-2-one Chemical compound CC(=O)C(Cl)CCO FYWDUQCSMYWUHV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
CJCSPKMFHVPWAR-JTQLQIEISA-N alpha-methyl-L-dopa Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 CJCSPKMFHVPWAR-JTQLQIEISA-N 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
229910021538 borax Inorganic materials 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000005191 phase separation Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002243 precursor Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
239000004328 sodium tetraborate Substances 0.000 description 3
235000010339 sodium tetraborate Nutrition 0.000 description 3
PMQMQIALVIXUTQ-BYPYZUCNSA-N (2s)-2-hydrazinyl-3-methylbutanoic acid Chemical compound CC(C)[C@H](NN)C(O)=O PMQMQIALVIXUTQ-BYPYZUCNSA-N 0.000 description 2
UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000012634 fragment Substances 0.000 description 2
239000003292 glue Substances 0.000 description 2
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
230000002452 interceptive effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000013557 residual solvent Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
NELACHBDCVNKTB-UHFFFAOYSA-N 1-oxa-2-azaspiro[2.5]octane Chemical compound C1CCCCC21ON2 NELACHBDCVNKTB-UHFFFAOYSA-N 0.000 description 1
ABUFEAKDTQPJQZ-UHFFFAOYSA-N 2,2-diethylbutane-1,1,1-triol Chemical compound CCC(CC)(CC)C(O)(O)O ABUFEAKDTQPJQZ-UHFFFAOYSA-N 0.000 description 1
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
FZOOXGZQJUAYHH-UHFFFAOYSA-N 2-hydrazinyl-2-phenylacetic acid Chemical compound NNC(C(O)=O)C1=CC=CC=C1 FZOOXGZQJUAYHH-UHFFFAOYSA-N 0.000 description 1
KHZVLGLEHBZEPO-UHFFFAOYSA-N 2-hydrazinyl-3-phenylpropanoic acid Chemical compound NNC(C(O)=O)CC1=CC=CC=C1 KHZVLGLEHBZEPO-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
150000004008 N-nitroso compounds Chemical class 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
DMHWOVJCMTWFMF-UHFFFAOYSA-N O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] Chemical compound O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] DMHWOVJCMTWFMF-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
206010047571 Visual impairment Diseases 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001370 alpha-amino acid derivatives Chemical class 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940127088 antihypertensive drug Drugs 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
210000003323 beak Anatomy 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
230000008499 blood brain barrier function Effects 0.000 description 1
210000001218 blood-brain barrier Anatomy 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
BHFLUDRTVIDDOR-QMMMGPOBSA-N methyl (2s)-2-amino-2-phenylacetate Chemical compound COC(=O)[C@@H](N)C1=CC=CC=C1 BHFLUDRTVIDDOR-QMMMGPOBSA-N 0.000 description 1
VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
229940067157 phenylhydrazine Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
SDKPSXWGRWWLKR-UHFFFAOYSA-M sodium;9,10-dioxoanthracene-1-sulfonate Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)[O-] SDKPSXWGRWWLKR-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP58144524A 1982-08-09 1983-08-09 アミノカルボン酸誘導体のｎ−アミノ化によるヒドラジノカルボン酸誘導体の製造法 Pending JPS6011448A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DD82242333A DD230865B1 (de)	1982-08-09	1982-08-09	Verfahren zur herstellung von hydrazinocarbonsaeurederivaten durch n-aminierung von aminocarbonsaeurederivaten
DD07C/24233		1982-08-09

Publications (1)

Publication Number	Publication Date
JPS6011448A true JPS6011448A (ja)	1985-01-21

Family

ID=5540516

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58144524A Pending JPS6011448A (ja)	1982-08-09	1983-08-09	アミノカルボン酸誘導体のｎ−アミノ化によるヒドラジノカルボン酸誘導体の製造法

Country Status (4)

Country	Link
JP (1)	JPS6011448A (de)
DD (1)	DD230865B1 (de)
HU (1)	HU188807B (de)
YU (1)	YU43527B (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7101912B2 (en)	2002-12-06	2006-09-05	Xenoport, Inc.	Carbidopa prodrugs and derivatives, and compositions and uses thereof
JP2019218356A (ja) *	2014-10-21	2019-12-26	アッヴィ・インコーポレイテッド	カルビドパおよびｌ−ドーパプロドラッグならびにそれらの使用方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU227283B1 (en) *	2005-10-12	2011-01-28	Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag	Process for the preparation of carbidopa
CN102702019B (zh) *	2012-06-16	2014-05-14	山东新华制药股份有限公司	卡比多巴的合成方法

1982
- 1982-08-09 DD DD82242333A patent/DD230865B1/de active IP Right Grant
- 1982-09-24 HU HU823089A patent/HU188807B/hu not_active IP Right Cessation
- 1982-09-28 YU YU2179/82A patent/YU43527B/xx unknown
1983
- 1983-08-09 JP JP58144524A patent/JPS6011448A/ja active Pending

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7101912B2 (en)	2002-12-06	2006-09-05	Xenoport, Inc.	Carbidopa prodrugs and derivatives, and compositions and uses thereof
JP2019218356A (ja) *	2014-10-21	2019-12-26	アッヴィ・インコーポレイテッド	カルビドパおよびｌ−ドーパプロドラッグならびにそれらの使用方法

Also Published As

Publication number	Publication date
DD230865A1 (de)	1985-12-11
DD230865B1 (de)	1987-05-20
HU188807B (en)	1986-05-28
YU43527B (en)	1989-08-31
YU217982A (en)	1985-03-20

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JPS6011448A - アミノカルボン酸誘導体のｎ−アミノ化によるヒドラジノカルボン酸誘導体の製造法 - Google Patents

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