DE2258411C3 - Verfahren zur Gewinnung von D-Penicillamin - Google Patents
Verfahren zur Gewinnung von D-PenicillaminInfo
- Publication number
- DE2258411C3 DE2258411C3 DE2258411A DE2258411A DE2258411C3 DE 2258411 C3 DE2258411 C3 DE 2258411C3 DE 2258411 A DE2258411 A DE 2258411A DE 2258411 A DE2258411 A DE 2258411A DE 2258411 C3 DE2258411 C3 DE 2258411C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- carboxylic acid
- norephedrine
- mol
- penicillamine
- 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
- 238000000034 method Methods 0.000 title claims description 14
- 229960001639 penicillamine Drugs 0.000 title claims description 6
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 title 1
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 claims description 10
- 229960000395 phenylpropanolamine Drugs 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- VVNCNSJFMMFHPL-GSVOUGTGSA-N L-penicillamine Chemical compound CC(C)(S)[C@H](N)C(O)=O VVNCNSJFMMFHPL-GSVOUGTGSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 230000007017 scission Effects 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- 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 2
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- -1 aliphatic sulfonic acids Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000566113 Branta sandvicensis Species 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- NARPMWPOFWHFDX-UHFFFAOYSA-N methanetrisulfonic acid Chemical compound OS(=O)(=O)C(S(O)(=O)=O)S(O)(=O)=O NARPMWPOFWHFDX-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- 229940081066 picolinic acid Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2258411A DE2258411C3 (de) | 1972-11-29 | 1972-11-29 | Verfahren zur Gewinnung von D-Penicillamin |
| HUDE811A HU168379B (enExample) | 1972-11-29 | 1973-03-14 | |
| ES418693A ES418693A2 (es) | 1972-11-29 | 1973-09-12 | Procedimiento para la recuperacion de d-penicilamina. |
| NO3693/73A NO138948C (no) | 1972-11-29 | 1973-09-20 | Fremgangsmaate til utvinning av d-penicillamin |
| DD173640A DD109215A6 (enExample) | 1972-11-29 | 1973-09-24 | |
| CH1372973A CH590182A5 (enExample) | 1972-11-29 | 1973-09-25 | |
| FI3151/73A FI56965C (fi) | 1972-11-29 | 1973-10-11 | Foerfarande foer framstaellning av d d-penicillamin |
| BE6044338A BE806378R (fr) | 1972-11-29 | 1973-10-22 | Procede pour l'obtention de d-penicillamine |
| AR250649A AR203731A1 (es) | 1972-11-29 | 1973-10-23 | Procedimiento para obtener d-penicilamina a partir de d,l--penicilamina |
| GB5061473A GB1413038A (en) | 1972-11-29 | 1973-10-31 | Process for obtaining d-penicillamine |
| ZA738498A ZA738498B (en) | 1972-11-29 | 1973-11-05 | Process for obtaining d-penicillamine |
| IL43567A IL43567A (en) | 1972-11-29 | 1973-11-05 | The preparation of d-penicillamine |
| IE1989/73A IE38489B1 (en) | 1972-11-29 | 1973-11-05 | Process for obtaining d-penicillamine |
| AT936073A AT325589B (de) | 1971-07-30 | 1973-11-07 | Verfahren zur gewinnung von d-penicillamin |
| AU62447/73A AU478937B2 (en) | 1973-11-13 | Process for obtaining d-penicillamine | |
| IT53884/73A IT1045950B (it) | 1972-11-29 | 1973-11-23 | Procedimento per l isolamento di o femicillammina |
| DK638973A DK146414C (da) | 1972-11-29 | 1973-11-27 | Fremgangsmaade til fremstilling af d-penicillamin |
| FR7342210A FR2207886B2 (enExample) | 1972-11-29 | 1973-11-27 | |
| JP13297873A JPS5512423B2 (enExample) | 1972-11-29 | 1973-11-27 | |
| RO7376809A RO71923A7 (ro) | 1972-11-29 | 1973-11-28 | Procedeu pentru prepararea d-penicilaminei |
| CS7300008188A CS183693B2 (en) | 1972-11-29 | 1973-11-28 | Method of obtaining d-penicilamine |
| SE7316110A SE382048B (sv) | 1972-11-29 | 1973-11-28 | Anvendning av 1-norefedrin for racematspaltning av d,l-penicillamin |
| SU1973450A SU535900A4 (ru) | 1972-11-29 | 1973-11-28 | Способ получени д-пеницилламина |
| BR9342/73A BR7309342D0 (pt) | 1972-11-29 | 1973-11-28 | Aperfeicoamento em processo de obtencao de acido d-b, b dimetilmercapto-a-amino propionico |
| CA186,936A CA1003853A (en) | 1972-11-29 | 1973-11-29 | Process for obtaining d-penicillamine |
| NL7316344.A NL163786C (nl) | 1972-11-29 | 1973-11-29 | Werkwijze voor het winnen van d-penicillamine uit dl-penicillamine. |
| US05/520,899 US3966752A (en) | 1971-07-30 | 1974-11-04 | Resolution of D,L-protected-penicillamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2258411A DE2258411C3 (de) | 1972-11-29 | 1972-11-29 | Verfahren zur Gewinnung von D-Penicillamin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2258411A1 DE2258411A1 (de) | 1974-06-06 |
| DE2258411B2 DE2258411B2 (de) | 1980-01-24 |
| DE2258411C3 true DE2258411C3 (de) | 1981-01-22 |
Family
ID=5863013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2258411A Expired DE2258411C3 (de) | 1971-07-30 | 1972-11-29 | Verfahren zur Gewinnung von D-Penicillamin |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5512423B2 (enExample) |
| AR (1) | AR203731A1 (enExample) |
| BE (1) | BE806378R (enExample) |
| BR (1) | BR7309342D0 (enExample) |
| CA (1) | CA1003853A (enExample) |
| CH (1) | CH590182A5 (enExample) |
| CS (1) | CS183693B2 (enExample) |
| DD (1) | DD109215A6 (enExample) |
| DE (1) | DE2258411C3 (enExample) |
| DK (1) | DK146414C (enExample) |
| ES (1) | ES418693A2 (enExample) |
| FI (1) | FI56965C (enExample) |
| FR (1) | FR2207886B2 (enExample) |
| GB (1) | GB1413038A (enExample) |
| HU (1) | HU168379B (enExample) |
| IE (1) | IE38489B1 (enExample) |
| IL (1) | IL43567A (enExample) |
| IT (1) | IT1045950B (enExample) |
| NL (1) | NL163786C (enExample) |
| NO (1) | NO138948C (enExample) |
| RO (1) | RO71923A7 (enExample) |
| SE (1) | SE382048B (enExample) |
| SU (1) | SU535900A4 (enExample) |
| ZA (1) | ZA738498B (enExample) |
-
1972
- 1972-11-29 DE DE2258411A patent/DE2258411C3/de not_active Expired
-
1973
- 1973-03-14 HU HUDE811A patent/HU168379B/hu unknown
- 1973-09-12 ES ES418693A patent/ES418693A2/es not_active Expired
- 1973-09-20 NO NO3693/73A patent/NO138948C/no unknown
- 1973-09-24 DD DD173640A patent/DD109215A6/xx unknown
- 1973-09-25 CH CH1372973A patent/CH590182A5/xx not_active IP Right Cessation
- 1973-10-11 FI FI3151/73A patent/FI56965C/fi active
- 1973-10-22 BE BE6044338A patent/BE806378R/xx not_active IP Right Cessation
- 1973-10-23 AR AR250649A patent/AR203731A1/es active
- 1973-10-31 GB GB5061473A patent/GB1413038A/en not_active Expired
- 1973-11-05 ZA ZA738498A patent/ZA738498B/xx unknown
- 1973-11-05 IL IL43567A patent/IL43567A/en unknown
- 1973-11-05 IE IE1989/73A patent/IE38489B1/xx unknown
- 1973-11-23 IT IT53884/73A patent/IT1045950B/it active
- 1973-11-27 DK DK638973A patent/DK146414C/da not_active IP Right Cessation
- 1973-11-27 JP JP13297873A patent/JPS5512423B2/ja not_active Expired
- 1973-11-27 FR FR7342210A patent/FR2207886B2/fr not_active Expired
- 1973-11-28 BR BR9342/73A patent/BR7309342D0/pt unknown
- 1973-11-28 RO RO7376809A patent/RO71923A7/ro unknown
- 1973-11-28 SE SE7316110A patent/SE382048B/xx unknown
- 1973-11-28 CS CS7300008188A patent/CS183693B2/cs unknown
- 1973-11-28 SU SU1973450A patent/SU535900A4/ru active
- 1973-11-29 CA CA186,936A patent/CA1003853A/en not_active Expired
- 1973-11-29 NL NL7316344.A patent/NL163786C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1045950B (it) | 1980-06-10 |
| AU6244773A (en) | 1975-05-15 |
| NO138948B (no) | 1978-09-04 |
| FI56965C (fi) | 1980-05-12 |
| CS183693B2 (en) | 1978-07-31 |
| NO138948C (no) | 1978-12-13 |
| IL43567A (en) | 1976-04-30 |
| DE2258411B2 (de) | 1980-01-24 |
| CH590182A5 (enExample) | 1977-07-29 |
| BE806378R (fr) | 1974-02-15 |
| AR203731A1 (es) | 1975-10-15 |
| FR2207886A2 (enExample) | 1974-06-21 |
| FI56965B (fi) | 1980-01-31 |
| FR2207886B2 (enExample) | 1978-01-06 |
| DK146414C (da) | 1984-03-12 |
| IE38489B1 (en) | 1978-03-29 |
| ES418693A2 (es) | 1977-11-01 |
| IE38489L (en) | 1974-05-29 |
| NL163786C (nl) | 1980-10-15 |
| SU535900A4 (ru) | 1976-11-15 |
| JPS5512423B2 (enExample) | 1980-04-02 |
| BR7309342D0 (pt) | 1974-08-29 |
| NL163786B (nl) | 1980-05-16 |
| ZA738498B (en) | 1974-10-30 |
| SE382048B (sv) | 1976-01-12 |
| JPS4982627A (enExample) | 1974-08-08 |
| DD109215A6 (enExample) | 1974-10-20 |
| DE2258411A1 (de) | 1974-06-06 |
| DK146414B (da) | 1983-10-03 |
| CA1003853A (en) | 1977-01-18 |
| HU168379B (enExample) | 1976-04-28 |
| GB1413038A (en) | 1975-11-05 |
| RO71923A7 (ro) | 1981-07-30 |
| NL7316344A (enExample) | 1974-05-31 |
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